JPH07145137A - N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient - Google Patents

N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient

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Publication number
JPH07145137A
JPH07145137A JP29678093A JP29678093A JPH07145137A JP H07145137 A JPH07145137 A JP H07145137A JP 29678093 A JP29678093 A JP 29678093A JP 29678093 A JP29678093 A JP 29678093A JP H07145137 A JPH07145137 A JP H07145137A
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JP
Japan
Prior art keywords
group
compound
phenyl
alkyl
nmr data
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.)
Pending
Application number
JP29678093A
Other languages
Japanese (ja)
Inventor
Masaji Oda
雅次 織田
Manabu Katsurada
学 桂田
Takafumi Tomita
啓文 富田
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.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
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Filing date
Publication date
Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to JP29678093A priority Critical patent/JPH07145137A/en
Publication of JPH07145137A publication Critical patent/JPH07145137A/en
Pending legal-status Critical Current

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  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

PURPOSE:To obtain a new N-phenylcarbamate derivative having excellent control effect on pathogenic fungi of various kinds of plants, having long residual effects, excellent in permeability to plants and useful as a germicide for agriculture and horticulture. CONSTITUTION:A compound of formula I {R1 is H, a 1-4C alkyl, a 2-5C alkenyl, a 2-5C alkyl, a 4-7C cycloalkylalkyl, a 4-7C cycloalkoxyalkyl, a l-4C haloalkyl, a 2-4C alkoxyalkyl, a 2-4C alkylthmoalkyl or (CR<6>R<7>)mCOY [R<6> and R<7> are H, a 1-2C alkyl; Y is H, 1-2C alkyl, a 1-4C alkoxy or a 1-4C alkylamino; (m) is 0 or 1]; R<2> is a 1-4C alkyl; R<3> and R<4> are H, a 1-4C alkyl; R<5> is an aryl or a heteroaryl; X is H, a halogen, a 1-4C alkyl or a l-4C alkoxy; (n) is 1-5}, e.g. methyl N-[2-{alpha-methyl-4-(trifluoromethylbenzyloxy) iminomethyl}phenyl{9147/28}-carbamate. The compound is obtained by using a benzaldehyde derivative of formula III as a starting substance.

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は、新規なＮ−フェニルカ
ーバメート誘導体およびこれを有効成分とする農園芸用
殺菌剤に関する。TECHNICAL FIELD The present invention relates to a novel N-phenylcarbamate derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

【０００２】[0002]

【従来の技術および発明が解決しようとする課題】従
来、ある種のＮ−フェニルカーバメート誘導体が殺菌効
果等の生物活性を有することは知られている。しかしな
がら、これらの化合物は農園芸用殺菌剤として、必ずし
も十分なものとは言えないのが現状であった。2. Description of the Related Art Conventionally, it is known that certain N-phenylcarbamate derivatives have biological activity such as bactericidal effect. However, at present, these compounds are not always sufficient as agricultural and horticultural fungicides.

【０００３】[0003]

【課題を解決するための手段】本発明者らは、かかるＮ
−フェニルカーバメート誘導体に着目し、鋭意検討を重
ねた結果、ある特定の構造を有するＮ−フェニルカーバ
メート誘導体が優れた殺菌活性を有し、かつ植物に対し
て極めて優れた浸透性を有することを見いだし、本発明
を完成するに至った。The present inventors have found that such N
As a result of intensive investigations focusing on a -phenylcarbamate derivative, it was found that an N-phenylcarbamate derivative having a specific structure has an excellent bactericidal activity and an extremely excellent penetrability to plants. The present invention has been completed.

【０００４】すなわち、本発明の要旨は、下記一般式
（I）で表されるＮ−フェニルカーバメート誘導体およ
びこれを有効成分とする農園芸用殺菌剤に存する。That is, the gist of the present invention resides in an N-phenylcarbamate derivative represented by the following general formula (I) and an agricultural and horticultural fungicide containing the N-phenylcarbamate derivative as an active ingredient.

【化２】 （上記一般式中、Ｒ1は水素原子、Ｃ1〜Ｃ4のアルキル
基、Ｃ2〜Ｃ5のアルケニル基、Ｃ2〜Ｃ5のアルキニル
基、Ｃ4〜Ｃ7のシクロアルキルアルキル基、Ｃ4〜Ｃ7の
シクロアルコキシアルキル基、Ｃ1〜Ｃ4のハロアルキル
基、Ｃ2〜Ｃ4のアルコキシアルキル基、Ｃ2〜Ｃ4アルキ
ルチオアルキル基または−（ＣＲ6Ｒ7）mＣＯＹを表し
（ただし、Ｒ6およびＲ7はそれぞれ独立して水素原子ま
たはＣ1〜Ｃ2のアルキル基を表し、Ｙは水素原子、Ｃ1
〜Ｃ2のアルキル基、Ｃ1〜Ｃ4のアルコキシ基またはＣ1
〜Ｃ4のアルキルアミノ基を表し、ｍは０または１を表
す）、Ｒ2はＣ1〜Ｃ4のアルキル基を表し、Ｒ3およびＲ
4はそれぞれ独立して水素原子またはＣ1〜Ｃ4のアルキ
ル基を表し、Ｒ5は置換されていてもよいアリール基ま
たはヘテロアリール基を表し、Ｘは水素原子、ハロゲン
原子、Ｃ1〜Ｃ4のアルキル基またはＣ1〜Ｃ4のアルコキ
シ基を表し、ｎは１〜５の整数を表し、ｎが２以上のと
きＸはそれぞれ異なっていてもよい）[Chemical 2] (In the above general formula, R 1 is a hydrogen atom, a C 1 to C 4 alkyl group, a C 2 to C 5 alkenyl group, a C 2 to C 5 alkynyl group, a C 4 to C 7 cycloalkylalkyl group, C 4 -C 7 cycloalkyl alkoxyalkyl group, a haloalkyl group of C 1 -C 4, an alkoxyalkyl group of C 2 ~C 4, C 2 ~C 4 alkylthioalkyl group or - represents (CR 6 R 7) m COY (However, R 6 and R 7 each independently represent a hydrogen atom or a C 1 -C 2 alkyl group, Y is a hydrogen atom, C 1
To C 2 alkyl group, C 1 to C 4 alkoxy group or C 1
To C 4 alkylamino group, m represents 0 or 1), R 2 represents a C 1 to C 4 alkyl group, R 3 and R
4 each independently represents a hydrogen atom or a C 1 -C 4 alkyl group, R 5 represents an optionally substituted aryl group or heteroaryl group, X represents a hydrogen atom, a halogen atom, C 1 -C 4 represents an alkyl group of 4 or a C 1 to C 4 alkoxy group, n represents an integer of 1 to 5, and when n is 2 or more, X may be different from each other.

【０００５】以下、本発明を詳細に説明する。本発明の
Ｎ−フェニルカーバメート誘導体は、上記一般式（I）
で表される。上記一般式（I）において、Ｒ1は水素原
子；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−ブチル基などのＣ1
〜Ｃ4のアルキル基；ビニル基、プロピニル基、ブテニ
ル基などのＣ2〜Ｃ5のアルケニル基；プロペニル基、ブ
チニル基またはペンチニル基などのＣ2〜Ｃ5のアルキニ
ル基；シクロプロピルメチル、シクロブチルエチル基な
どのＣ4〜Ｃ7のシクロアルキルアルキル基；シクロプロ
ポキシメチルなどのＣ4〜Ｃ7のシクロアルコキシアルキ
ル基；トリフルオロメチル基、ジフルオロメチル基、ト
リクロロメチル基またはジクロロジフルオロエチル基な
どのＣ1〜Ｃ4のハロアルキル基；メトキシメチル基、エ
トキシメチル基、メトキシエチル基またはエトキシエチ
ル基などのＣ2〜Ｃ4のアルコキシアルキル基；エチルチ
オメチル基、メチルチオメチル基、エチルチオエチル基
などのＣ2〜Ｃ4のアルキルチオアルキル基；またはフォ
ルミル基、アセチル基、メトキシカルボニル基、エトキ
シカルボニル基、メチルカルバモイル基またはメトキシ
カルボニルメチル基などの一般式−（ＣＲ6Ｒ7）mＣＯ
Ｙで表される基（一般式中、Ｒ6およびＲ7はそれぞれ独
立して水素原子またはメチル基などのＣ1〜Ｃ2のアルキ
ル基を表し、Ｙは水素原子；メチル基、エチル基などの
Ｃ1〜Ｃ2のアルキル基；メトキシ基、エトキシ基などの
Ｃ1〜Ｃ4のアルコキシ基；またはメチルアミノ基、エチ
ルアミノ基などのＣ1〜Ｃ4のアルキルアミノ基を表し、
ｍは０または１を表す）を表す。Ｒ1の好ましい基とし
てはメチル基、エチル基、ｎ-プロピル基、ｉｓｏ−プ
ロピル基、プロペニル基、プロパルギル基、メトキシメ
チル基、エトキシメチル基などが挙げられる。The present invention will be described in detail below. The N-phenylcarbamate derivative of the present invention has the general formula (I) above.
It is represented by. In the above general formula (I), R 1 is a hydrogen atom; C 1 such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group
To C 4 alkyl group; C 2 to C 5 alkenyl group such as vinyl group, propynyl group, butenyl group; C 2 to C 5 alkynyl group such as propenyl group, butynyl group or pentynyl group; cyclopropylmethyl, cyclo C 4 -C 7 cycloalkyl group such as butyl ethyl group; cyclopropoxy C 4 -C 7 cycloalkoxy group such as methyl; trifluoromethyl group, difluoromethyl group, trichloromethyl group or dichlorodifluoromethane ethyl group, etc. haloalkyl group of C 1 -C 4; methoxymethyl group, ethoxymethyl group, an alkoxyalkyl group of C 2 -C 4, such as a methoxyethyl group or an ethoxyethyl group; ethylthiomethyl group, methylthiomethyl group, ethylthiomethyl ethyl alkylthioalkyl group of C 2 -C 4, such as; or formyl , An acetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a methylcarbamoyl group or a methoxycarbonylmethyl group- (CR 6 R 7 ) m CO
A group represented by Y (in the general formula, R 6 and R 7 each independently represent a hydrogen atom or a C 1 -C 2 alkyl group such as a methyl group, and Y is a hydrogen atom; a methyl group, an ethyl group, etc. A C 1 -C 2 alkyl group; a C 1 -C 4 alkoxy group such as a methoxy group or an ethoxy group; or a C 1 -C 4 alkylamino group such as a methylamino group or an ethylamino group,
m represents 0 or 1). Preferred examples of R 1 include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a propenyl group, a propargyl group, a methoxymethyl group and an ethoxymethyl group.

【０００６】Ｒ2はメチル基、エチル基、ｎ-プロピル
基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｓｅｃ−ブチ
ル基などのＣ1〜Ｃ4のアルキル基を表す。好ましくはＲ
2はメチル基である。Ｒ3およびＲ4はそれぞれ独立して
水素原子；またはメチル基、エチル基、ｎ-プロピル
基、ｉｓｏ−プロピル基、ｎ-ブチル基、ｓｅｃ−ブチ
ル基などのＣ1〜Ｃ4のアルキル基を表す。これらの中で
も、Ｒ3およびＲ4としては水素原子またはメチル基が好
ましい。R 2 represents a C 1 -C 4 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group and a sec-butyl group. Preferably R
2 is a methyl group. R 3 and R 4 are each independently a hydrogen atom; or a C 1 -C 4 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, or a sec-butyl group. Represent Among these, a hydrogen atom or a methyl group is preferable as R 3 and R 4 .

【０００７】Ｒ5はフェニル基、ナフチル基などの置換
されていてもよいアリール基；またはピリジル基、チア
ゾリル基などの適宜置換されていてもよいヘテロアリー
ル基を表す。上記アリール基およびヘテロアリール基は
シアノ基；ニトロ基；水素原子；フッ素原子、塩素原
子、臭素原子などのハロゲン原子；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−ブチル基などのＣ1〜Ｃ4のアルキル基；ト
リフルオロメチル基、ジフルオロメチル基、トリクロロ
メチル基またはジクロロジフルオロエチル基などのＣ1
〜Ｃ4のハロアルキル基；ハロゲン原子またはＣ3〜Ｃ6
のシクロアルキル基で置換されていてもよいメトキシ
基、エトキシ基、ｉｓｏ−プロポキシ基、ｎ−ブトキシ
基などのＣ1〜Ｃ6のアルコキシ基；またはメチルチオ
基、エチルチオ基、ｉｓｏ−プロピルチオ基、ｎ−ブチ
ルチオ基などのＣ1〜Ｃ6のアルキルチオ基などにより置
換されていてもよい。また隣接する二つの置換基が一緒
になってアリール基またはヘテロアリール基と縮合環を
形成してもよい。置換基の数は１〜５個、好ましくは１
〜２個である。複数個の置換基を有する場合同じでも異
なっていても良い。好ましい置換基としては、Ｃ1〜Ｃ4
アルキル基、ハロゲン原子、ハロゲン原子特に好ましく
はフッ素原子により置換されていてもよいＣ1〜Ｃ4アル
コキシ基、ハロゲン原子特に好ましくはフッ素原子によ
り置換されていてもよいＣ1〜Ｃ3アルキルスルフォニル
オキシ基またはトリフルオロメチル基である。R 5 represents an optionally substituted aryl group such as a phenyl group or a naphthyl group; or an optionally substituted heteroaryl group such as a pyridyl group or a thiazolyl group. The above aryl group and heteroaryl group include a cyano group; a nitro group; a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom; , C 1 -C 4 alkyl groups such as sec- butyl; such as trifluoromethyl group, difluoromethyl group, trichloromethyl group or dichlorodifluoromethane ethyl group C 1
To C 4 haloalkyl group; halogen atom or C 3 to C 6
A C 1 -C 6 alkoxy group such as a methoxy group, an ethoxy group, an iso-propoxy group and an n-butoxy group which may be substituted with a cycloalkyl group; or a methylthio group, an ethylthio group, an iso-propylthio group, n It may be substituted with a C 1 -C 6 alkylthio group such as -butylthio group. Also, two adjacent substituents may be combined with each other to form a condensed ring with an aryl group or a heteroaryl group. The number of substituents is 1 to 5, preferably 1.
~ 2 pieces. When having a plurality of substituents, they may be the same or different. Preferred substituents are C 1 to C 4
Alkyl group, halogen atom, halogen atom, particularly preferably C 1 -C 4 alkoxy group optionally substituted by fluorine atom, halogen atom, particularly preferably C 1 -C 3 alkylsulfonyloxy optionally substituted by fluorine atom. A group or a trifluoromethyl group.

【０００８】Ｘは水素原子；フッ素原子、塩素原子、臭
素原子などのハロゲン原子；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、ｓｅ
ｃ−ブチル基などのＣ1〜Ｃ4のアルキル基；メトキシ
基、エトキシ基、ｉｓｏ−プロポキシ基、ｎ−ブトキシ
基などのＣ1〜Ｃ4のアルコキシ基を表す。Ｘとしては、
水素原子が好ましい。ｎは１〜５の整数を、好ましくは
１〜３の整数を表す。本発明化合物は、いずれも新規化
合物であり、例えば下記の反応式に従って製造される。X is a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom; a methyl group, an ethyl group or n-
Propyl group, iso-propyl group, n-butyl group, se
A C 1 -C 4 alkyl group such as a c-butyl group; a C 1 -C 4 alkoxy group such as a methoxy group, an ethoxy group, an iso-propoxy group, and an n-butoxy group. As X,
A hydrogen atom is preferred. n represents an integer of 1 to 5, preferably an integer of 1 to 3. The compounds of the present invention are all novel compounds and are produced, for example, according to the following reaction formula.

【０００９】[0009]

【化３】 [Chemical 3]

【００１０】（上記式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、
Ｘ、およびｎは前記一般式（I）において定義したとお
りである。）上記一般式（I）の化合物は、上記一般式
（II）で表されるカーバメート誘導体と、相当するハラ
イド誘導体を塩基の存在下反応させることにより得られ
る。一般式（II）で表されるカーバメート誘導体は一般
式（III）で表されるベンズアルデヒド誘導体と、相当
するアルコキシアミン誘導体を反応させるか、あるいは
ベンズアルデヒド誘導体（III）にヒドロキシアミンを
反応させ、オキシム誘導体（IV）とした後、エーテル化
することにより製造される。(In the above formula, R 1 , R 2 , R 3 , R 4 , R 5 ,
X and n are as defined in the general formula (I). ) The compound of the general formula (I) can be obtained by reacting the carbamate derivative represented by the general formula (II) with a corresponding halide derivative in the presence of a base. The carbamate derivative represented by the general formula (II) can be obtained by reacting a benzaldehyde derivative represented by the general formula (III) with a corresponding alkoxyamine derivative or by reacting a benzaldehyde derivative (III) with a hydroxyamine. (IV) and then etherified.

【００１１】上記反応に用いられる塩基の例としては、
水素化ナトリウムなどのアルカリ金属水素化物；ナトリ
ウムメチラートなどのアルカリ金属アルコラート；炭酸
カリウムなどのアルカリ金属炭酸化物；水酸化カリウム
などのアルカリ金属水酸化物；Ｎ−メチルモルホリンや
トリエチルアミンなどの３級アミン；ピリジンやピコリ
ンのような芳香族塩基などが挙げられる。Examples of the base used in the above reaction include:
Alkali metal hydrides such as sodium hydride; Alkali metal alcoholates such as sodium methylate; Alkali metal carbonates such as potassium carbonate; Alkali metal hydroxides such as potassium hydroxide; Tertiary amines such as N-methylmorpholine and triethylamine. An aromatic base such as pyridine or picoline.

【００１２】かくして得られる本発明化合物は、いずれ
も新規であり、優れた殺菌活性を有している。特に各種
植物の病原菌に対して優れた防除効果を有することか
ら、農園芸用殺菌剤として有用である。例えば、稲のい
もち病（Pyricularia orizae）；稲の紋枯れ病（Rhizoc
tonia solani）；麦類のうどんこ病（Erysiphe gramini
s）；麦類の各種さび病（Puccinia recondita）；野
菜、果樹などの灰色かび病（Botrytis cinerea）；各種
作物の疫病（Phytophthora infestance）などに対して
高い活性を有するのみならず、残効性が長く、植物に対
する浸透性にも優れていることから、農園芸用殺菌剤と
して有用である。The compounds of the present invention thus obtained are all novel and have excellent bactericidal activity. Particularly, since it has an excellent control effect against pathogenic bacteria of various plants, it is useful as a fungicide for agriculture and horticulture. For example, rice blast (Pyricularia orizae); rice blight (Rhizoc)
tonia solani); powdery mildew of wheat (Erysiphe gramini)
s); Various rust diseases of wheat (Puccinia recondita); Gray mold disease of vegetables and fruit trees (Botrytis cinerea); Not only highly active against plague (Phytophthora infestance) of various crops, but also residual efficacy It is useful as a fungicide for agricultural and horticultural use because it has a long period of time and has excellent permeability to plants.

【００１３】本発明化合物を農園芸用殺菌剤として使用
するにあたっては、この化合物をそのまま使用してもよ
いが、有効性分の施用場面での分散を有効にするため、
常法に従い、補助剤を添加し、乳剤、水和剤、粉剤、粒
剤などの形で使用するのが好ましい。本発明の農園芸用
殺菌剤を施用するにあたり、乳剤の形で使用する場合に
は本発明化合物１０〜８０部、好ましくは１０〜７０
部、溶剤１０〜９０部、好ましくは２０〜８０部と界面
活性剤３〜２０部、好ましくは５〜１５部を適当な割合
に混合したものを原料とし、使用に際しては水で所定濃
度に希釈し、これを散布などの方法によって施用する。When the compound of the present invention is used as a fungicide for agricultural and horticultural use, the compound may be used as it is, but in order to effectively disperse the effective component in the application scene,
In accordance with a conventional method, it is preferable to add an auxiliary agent and use it in the form of emulsion, wettable powder, powder, granule and the like. When applying the agricultural or horticultural fungicide of the present invention, when used in the form of an emulsion, the compound of the present invention is contained in an amount of 10 to 80 parts, preferably 10 to 70 parts.
Part, solvent 10 to 90 parts, preferably 20 to 80 parts and a surfactant 3 to 20 parts, preferably 5 to 15 parts as a raw material, and when used, diluted to a predetermined concentration with water. Then, apply this by a method such as spraying.

【００１４】水和剤の形で使用する場合には本発明化合
物５〜８０部、好ましくは１０〜７０部および増量剤１
０〜９０部、好ましくは２０〜８０部と界面活性剤１〜
２０部、好ましくは３〜１５部を適当な割合に混合し、
該混合物を乳剤の場合と同様に水などで所定濃度に希釈
し使用する。When used in the form of a wettable powder, the compound of the present invention is 5 to 80 parts, preferably 10 to 70 parts and extender 1
0-90 parts, preferably 20-80 parts and surfactant 1-
20 parts, preferably 3 to 15 parts are mixed in a suitable ratio,
The mixture is diluted with water to a predetermined concentration and used in the same manner as the emulsion.

【００１５】粉剤の形で使用する場合には本発明化合物
０．１〜１０部、好ましくは１〜５部をカオリン、ベン
トナイト、タルクなどの増量剤９０〜９９.９部、好ま
しくは９５〜９９部とを均一に混合したものを使用す
る。本発明の農園芸用殺菌剤は、本有効成分の殺菌効果
を阻害することのない他の活性成分、例えば殺菌剤、殺
虫剤、殺ダニ剤などと混合して使用することもできる。
本発明の農園芸用殺菌剤は、茎葉散布および水面施用の
いずれも好適に適用できる。茎葉散布の場合は、通常乳
剤または水和剤の形で有効性分を１０〜１０００ｐｐｍ
含むように水で希釈し、これを１０アール当たり１０〜
５００リットル施用すればよい。When used in the form of powder, 0.1 to 10 parts, preferably 1 to 5 parts of the compound of the present invention is used as a bulking agent such as kaolin, bentonite and talc 90 to 99.9 parts, preferably 95 to 99. Use a mixture of parts and parts evenly. The fungicide for agricultural and horticultural use of the present invention can also be used as a mixture with other active ingredients that do not inhibit the fungicidal effect of the present active ingredient, for example, fungicides, insecticides, acaricides and the like.
The agricultural and horticultural fungicide of the present invention can be suitably applied to both foliar application and water surface application. In the case of foliage spray, the effective content is usually 10 to 1000 ppm in the form of emulsion or wettable powder.
Dilute with water to contain 10 to 10 are
Apply 500 liters.

【００１６】[0016]

【実施例】次に本発明の実施例を挙げてさらに具体的に
説明するが、本発明はその要旨を越えない限り、以下の
実施例に限定されるものではない。 合成例１ メチルＮ−［２−｛α−メチル−４−（トリフルオロメ
チルベンジルオキシ）イミノメチル｝フェニル］カーバ
メートの合成（表１中化合物Ｎｏ．１０）１−（４−ト
リフルオロメチルフェニル）エトキシアミン（４ｇ；１
８．２ｍｍｏｌ）、メチルＮ−（２−ホルミルフェニ
ル）カーバメート（３ｇ；１８．２ｍｍｏｌ）のメタノ
ール溶液５ｍｌを室温にて一夜放置した。反応液を減圧
濃縮後残渣をシリカゲルカラムクロマトグラフィー（Ｓ
ｉＯ2 ５０ｇ、ｎ−ヘキサン／酢酸エチル＝７／１）に
より精製して６．７ｇの標題化合物を得た（収率 ８
９．０％）。出発原料を変える以外は全く同様にして表
１中の化合物Ｎｏ．１，５，１９，２３，２６，２９お
よび３２を合成した。EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist. Synthesis Example 1 Synthesis of methyl N- [2- {α-methyl-4- (trifluoromethylbenzyloxy) iminomethyl} phenyl] carbamate (Compound No. 10 in Table 1) 1- (4-trifluoromethylphenyl) ethoxy Amine (4g; 1
5 ml of a methanol solution of methyl N- (2-formylphenyl) carbamate (3 g; 18.2 mmol) was left overnight at room temperature. After concentrating the reaction solution under reduced pressure, the residue is subjected to silica gel column chromatography (S
Purification by iO 2 50 g, n-hexane / ethyl acetate = 7/1) gave 6.7 g of the title compound (yield 8
9.0%). Compound No. 1 in Table 1 was prepared in exactly the same manner except that the starting materials were changed. 1, 5, 19, 23, 26, 29 and 32 were synthesized.

【００１７】合成例２ メチルＮ−メトキシメチル−Ｎ−［２−｛α−メチル−
４−（トリフルオロメチルベンジルオキシ）イミノメチ
ル｝フェニル］カーバメートの合成（表１中化合物Ｎ
ｏ．１１） メチル−Ｎ−［２−｛α−メチル−４−（トリフルオロ
メチルベンジルオキシ）イミノメチル｝フェニル］カー
バメート（０．６ｇ；１．７ｍｍｏｌ）のＤＭＦ溶液に
６０％ＮａＨ（０．０７ｇ；１．７５ｍｍｏｌ）を加え
２０分間撹拌した。次いでメトキシメチルクロライド
（０．１４ｇ；１．７５ｍｍｏｌ）を加え室温にて一夜
放置した。酢酸エチル、水を加え、有機層を抽出し、水
および飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥
した。溶媒を留去し残渣をシリカゲルカラムクロマトグ
ラフィー（ＳｉＯ2 ５０ｇ、ｎ−ヘキサン／酢酸エチル
＝６／１）により精製して、０．５９ｇの標題化合物を
得た（収率８８．０％）。出発原料を変える以外は全く
同様にして、表１中の化合物Ｎｏ．２〜４，６〜９，１
１〜１８，２０〜２２，２４，２５，２７，２８，３
０，３１および３３〜７３を合成した。以上、得られた
化合物を下記表１に示す。Synthesis Example 2 Methyl N-methoxymethyl-N- [2- {α-methyl-
Synthesis of 4- (trifluoromethylbenzyloxy) iminomethyl} phenyl] carbamate (Compound N in Table 1
o. 11) 60% NaH (0.07 g; 1) in a DMF solution of methyl-N- [2- {α-methyl-4- (trifluoromethylbenzyloxy) iminomethyl} phenyl] carbamate (0.6 g; 1.7 mmol). 0.75 mmol) was added and stirred for 20 minutes. Then, methoxymethyl chloride (0.14 g; 1.75 mmol) was added and the mixture was left at room temperature overnight. Ethyl acetate and water were added, the organic layer was extracted, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (SiO 2 50 g, n-hexane / ethyl acetate = 6/1) to obtain 0.59 g of the title compound (yield 88.0%). Compound No. 1 in Table 1 was prepared in exactly the same manner except that the starting materials were changed. 2-4, 6-9, 1
1-18, 20-22, 24, 25, 27, 28, 3
0,31 and 33-73 were synthesized. The compounds thus obtained are shown in Table 1 below.

【００１８】[0018]

【表１】表１ ─────────────────────────────────── 化合物Ｎｏ． Ｒ1 Ｒ2 Ｒ3 Ｒ4 Ｒ5 物性 ─────────────────────────────────── １ Ｈ ＣＨ3 Ｈ ＣＨ3 フェニル 粘稠性 ２ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 フェニル 粘稠性 ３ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 フェニル 粘稠性 ４ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ Ｃ2Ｈ5 フェニル 粘稠性 ５ Ｈ ＣＨ3 Ｈ ＣＨ3 3-CF3-フェニル 粘稠性 ６ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3-CF3-フェニル 粘稠性 ７ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 3-CF3-フェニル 粘稠性 ８ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 3-CF3-フェニル 粘稠性 ９ エトキシメチル ＣＨ3 Ｈ ＣＨ3 3-CF3-フェニル 粘稠性 １０ Ｈ ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １１ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １２ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １３ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １４ ＣＨ3 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １５ n-Ｃ3Ｈ7 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １６ iso-Ｃ3Ｈ7 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １７ フ゜ロヘ゜ニル ＣＨ3 Ｈ Ｃ2Ｈ5 4-CF3-フェニル 粘稠性 ───────────────────────────────────[Table 1] Table 1 ————————————————————————————— Compound No. R 1 R 2 R 3 R 4 R 5 Physical properties ──────────────────────────────────── 1 H CH 3 H CH 3 Phenyl Viscosity 2 CH 2 OCH 3 CH 3 H CH 3 Phenyl Viscosity 3 C 2 H 5 CH 3 H CH 3 Phenyl Viscosity 4 Fluorophenyl CH 3 H C 2 H 5 Phenyl Viscosity 5 H CH 3 H CH 3 3-CF 3 -Phenyl viscous 6 CH 2 OCH 3 CH 3 H CH 3 3-CF 3 -Phenyl viscous 7 C 2 H 5 CH 3 H CH 3 3-CF 3 -Phenyl viscous Consistency 8 Fluorogel CH 3 H CH 3 3-CF 3 -phenyl Viscosity 9 Ethoxymethyl CH 3 H CH 3 3-CF 3 -Phenyl Viscosity 10 H CH 3 H CH 3 4-CF 3 -Phenyl Viscosity sex 11 CH 2 OCH 3 CH 3 H CH 3 4-CF 3 - phenyl viscous 12 C 2 H 5 CH 3 H CH 3 4-CF 3 - phenyl viscous 13 prop Ruki Bu le C 3 H CH 3 4-CF 3 - phenyl viscous 14 CH 3 CH 3 H CH 3 4-CF 3 - phenyl viscous 15 n-C 3 H 7 CH 3 H CH 3 4-CF 3 - phenyl viscous Properties 16 iso-C 3 H 7 CH 3 H CH 3 4-CF 3 -Phenyl viscous 17 Fluorenyl CH 3 H C 2 H 5 4-CF 3 -Phenyl viscous ─────────── ─────────────────────────

【００１９】[0019]

【表２】 表１のつづき ─────────────────────────────────── 化合物Ｎｏ． Ｒ1 Ｒ2 Ｒ3 Ｒ4 Ｒ5 物性 ─────────────────────────────────── １８ CH2CO2CH3 ＣＨ3 Ｈ ＣＨ3 4-CF3-フェニル 粘稠性 １９ Ｈ ＣＨ3 Ｈ ＣＨ3 3-CH3-フェニル 粘稠性 ２０ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 3-CH3-フェニル 粘稠性 ２１ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 3-CH3-フェニル 粘稠性 ２２ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3-CH3-フェニル 粘稠性 ２３ Ｈ ＣＨ3 Ｈ ＣＨ3 3-OCF3-フェニル 粘稠性 ２４ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3-OCF3-フェニル 粘稠性 ２５ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 3-OCF3-フェニル 粘稠性 ２６ Ｈ ＣＨ3 Ｈ ＣＨ3 4-CH3-フェニル 粘稠性 ２７ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 4-CH3-フェニル 粘稠性 ２８ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 4-CH3-フェニル 粘稠性 ２９ Ｈ ＣＨ3 Ｈ ＣＨ3 3-Cl-フェニル 粘稠性 ３０ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3-Cl-フェニル 粘稠性 ３１ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 3-Cl-フェニル 粘稠性 ３２ Ｈ ＣＨ3 Ｈ Ｃ2Ｈ5 4-Cl-フェニル 粘稠性 ３３ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 4-Cl-フェニル 粘稠性 ３４ Ｃ2Ｈ5 ＣＨ3 Ｈ ＣＨ3 4-Cl-フェニル 粘稠性 ３５ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 2-CH3-フェニル 粘稠性 ３６ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 2-CH3-5-Cl-フェニル 粘稠性 ３７ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3-Cl-4-Cl-フェニル 粘稠性 ３８ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 2-Cl-5-Cl-フェニル 粘稠性 ３９ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 2-CH3-5-CH3-フェニル 粘稠性 ───────────────────────────────────[Table 2] Continuation of Table 1 ─────────────────────────────────── Compound No. R 1 R 2 R 3 R 4 R 5 Physical Properties ─────────────────────────────────── 18 CH 2 CO 2 CH 3 CH 3 H CH 3 4-CF 3 -phenyl viscous 19 H CH 3 H CH 3 3-CH 3 -phenyl viscous 20 C 2 H 5 CH 3 H CH 3 3-CH 3 -phenyl viscous Consistency 21 Prorogel CH 3 H CH 3 3-CH 3 -Phenyl Viscosity 22 CH 2 OCH 3 CH 3 H CH 3 3-CH 3 -Phenyl Consistency 23 H CH 3 H CH 3 3-OCF 3 -Phenyl Viscosity 24 CH 2 OCH 3 CH 3 H CH 3 3-OCF 3 -phenyl Viscosity 25 C 2 H 5 CH 3 H CH 3 3-OCF 3 -Phenyl Viscosity 26 H CH 3 H CH 3 4- CH 3 -Phenyl viscous 27 C 2 H 5 CH 3 H CH 3 4-CH 3 -Phenyl viscous 28 CH 2 OCH 3 CH 3 H CH 3 4-CH 3 -Phenyl viscous 29 H CH 3 H CH 3 3-Cl-phenyl Viscosity 30 CH 2 OCH 3 CH 3 H CH 3 3-Cl-phenyl viscous 31 C 2 H 5 CH 3 H CH 3 3-Cl-phenyl viscous 32 H CH 3 H C 2 H 5 4-Cl-phenyl viscous 33 CH 2 OCH 3 CH 3 H CH 3 4-Cl-phenyl viscous 34 C 2 H 5 CH 3 H CH 3 4-Cl-phenyl viscous 35 CH 2 OCH 3 CH 3 H CH 3 2-CH 3 -phenyl viscous 36 CH 2 OCH 3 CH 3 H CH 3 2-CH 3 -5-Cl-phenyl viscous 37 CH 2 OCH 3 CH 3 H CH 3 3-Cl-4-Cl-phenyl viscous Properties 38 CH 2 OCH 3 CH 3 H CH 3 2-Cl-5-Cl-phenyl Viscosity 39 CH 2 OCH 3 CH 3 H CH 3 2-CH 3 -CH 3 -Phenyl Viscosity ─── ────────────────────────────────

【００２０】[0020]

【表３】 表１のつづき ─────────────────────────────────── 化合物Ｎｏ． Ｒ1 Ｒ2 Ｒ3 Ｒ4 Ｒ5 物性 ─────────────────────────────────── ４０ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 6-CF3-ヒ゜リシ゛ン-2-イル 粘稠性 ４１ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 6-Cl-ヒ゜リシ゛ン-2-イル 粘稠性 ４２ Ｃ2Ｈ5 ＣＨ3 ＣＨ3 ＣＨ3 4-CH3-フェニル 粘稠性 ４３ CH2OCH3 ＣＨ3 ＣＨ3 ＣＨ3 4-CH3-フェニル 粘稠性 ４４ CH2OCH3 ＣＨ3 Ｈ Ｈ 4-CF3-フェニル 粘稠性 ４５ CH2OCH3 ＣＨ3 Ｈ Ｈ 4-CH3-フェニル 粘稠性 ４６ CH2OCH3 ＣＨ3 Ｈ Ｈ 3-CF3-フェニル 粘稠性 ４７ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-CH3-フェニル 粘稠性 ４８ CH2OCH3 ＣＨ3 Ｈ Ｈ 4-Cl-フェニル 粘稠性 ４９ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-Cl-フェニル 粘稠性 ５０ CH2SCH3 ＣＨ3 Ｈ ＣＨ3 4-Cl-フェニル 粘稠性 ５１ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 4-NO2-フェニル 粘稠性 ５２ CH2OCH3 ＣＨ3 Ｈ Ｈ 3,5-(CF3)2-フェニル 粘稠性 ５３ CH2OCH3 ＣＨ3 Ｈ Ｈ 3-(OCH3)-フェニル 粘稠性 ５４ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3,4-(OCH3)2-フェニル 粘稠性 ５５ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3,4-エチレンシ゛オキシフェニル 粘稠性 ５６ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 3,4-メチレンシ゛オキシフェニル 粘稠性 ５７ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ Ｈ 4-CN-フェニル 粘稠性 ５８ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ Ｈ 3-CN-フェニル 粘稠性 ５９ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OCH3)-フェニル 粘稠性 ６０ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OC2H5)-フェニル 粘稠性 ６１ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 3-(OC3H7)-フェニル 粘稠性 ───────────────────────────────────[Table 3] Continuation of Table 1 ─────────────────────────────────── Compound No. R 1 R 2 R 3 R 4 R 5 Physical Properties ─────────────────────────────────── 40 CH 2 OCH 3 CH 3 H CH 3 6-CF 3 -Peridin-2-yl Viscosity 41 CH 2 OCH 3 CH 3 H CH 3 6-Cl-Porigin-2-yl Viscosity 42 C 2 H 5 CH 3 CH 3 CH 3 4-CH 3 -Phenyl viscous 43 CH 2 OCH 3 CH 3 CH 3 CH 3 4-CH 3 -Phenyl viscous 44 CH 2 OCH 3 CH 3 H H 4-CF 3 -Phenyl viscous 45 CH 2 OCH 3 CH 3 H H 4-CH 3 -Phenyl viscous 46 CH 2 OCH 3 CH 3 H H 3-CF 3 -Phenyl viscous 47 Fluoroalkyl CH 3 H CH 3 4-CH 3 -Phenyl viscous Properties 48 CH 2 OCH 3 CH 3 H H 4-Cl-phenyl viscous 49 Fluoropropyl CH 3 H CH 3 4-Cl-phenyl viscous 50 CH 2 SCH 3 CH 3 H CH 3 4-Cl-phenyl viscous Properties 51 CH 2 OCH 3 CH 3 H C H 3 4-NO 2 -Phenyl viscous 52 CH 2 OCH 3 CH 3 H H 3,5- (CF 3 ) 2 -Phenyl viscous 53 CH 2 OCH 3 CH 3 H H 3- (OCH 3 )- Phenyl Viscosity 54 CH 2 OCH 3 CH 3 H CH 3 3,4- (OCH 3 ) 2 -Phenyl Viscosity 55 CH 2 OCH 3 CH 3 H CH 3 3,4-Ethylenedioxyphenyl Viscosity 56 CH 2 OCH 3 CH 3 H CH 3 3,4-Methylenedioxyphenyl Viscosity 57 Fluoro CH 3 H H 4-CN-Phenyl Viscosity 58 Fluoro CH 3 H H 3-CN-Phenyl Viscosity 59 Fluoro CH 3 H CH 3 4- (OCH 3 ) -Phenyl viscous 60 Fluoro CH 3 H CH 3 4- (OC 2 H 5 ) -Phenyl viscous 61 Fluoro CH 3 H CH 3 3- (OC 3 H 7 ) -Phenyl consistency ───────────────────────────────────

【００２１】[0021]

【表４】 表１のつづき ─────────────────────────────────── 化合物Ｎｏ． Ｒ1 Ｒ2 Ｒ3 Ｒ4 Ｒ5 物性 ─────────────────────────────────── ６２ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OC3H7-iso)-フェニル 粘稠性 ６３ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-C2H5-フェニル 粘稠性 ６４ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-t-C4H9-フェニル 粘稠性 ６５ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-フ゜ロハ゜ルキ゛ルオキシフェニル 粘稠性 ６６ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OCF3)-フェニル 粘稠性 ６７ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OCH2CF3)-フェニル 粘稠性 ６８ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OCH2CF2CF3)-フェニル 粘稠性 ６９ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-OSO2-フェニル 粘稠性 ７０ CH2OCH3 ＣＨ3 Ｈ ＣＨ3 4-OSO2-フェニル 粘稠性 ７１ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 3-(OCHF2)-フェニル 粘稠性 ７２ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-(OCHF2)-フェニル 粘稠性 ７３ フ゜ロハ゜ルキ゛ル ＣＨ3 Ｈ ＣＨ3 4-ナフチル 粘稠性 ───────────────────────────────────[Table 4] Continuation of Table 1 ─────────────────────────────────── Compound No. R 1 R 2 R 3 R 4 R 5 Physical Properties ─────────────────────────────────── 62 Fluoroalkyl CH 3 H CH 3 4- (OC 3 H 7 -iso) - phenyl viscous 63 prop Ruki Bu Le CH 3 H CH 3 4-C 2 H 5 - phenyl viscous 64 prop Ruki Bu Le CH 3 H CH 3 4-tC 4 H 9 - Phenyl Viscosity 65 FluoroCHyl CH 3 H CH 3 4-Propoxyl Oxyphenyl Viscosity 66 Fluorophilic CH 3 H CH 3 4- (OCF 3 ) -Phenyl Viscosity 67 Fluorophilic CH 3 H CH 3 4- (OCH 2 CF 3 ) -Phenyl viscous 68 Fluorophenyl CH 3 H CH 3 4- (OCH 2 CF 2 CF 3 ) -Phenyl viscous 69 Fluorophenyl CH 3 H CH 3 4-OSO 2 -Phenyl viscous 70 CH 2 OCH 3 CH 3 H CH 3 4-OSO 2 -phenyl viscous 71 Propoxyl CH 3 H CH 3 3- (OCHF 2 ) -Phenyl viscous 72 Propoxyl CH 3 H CH 3 4- (OCHF 2 ) -Phenyl viscous 73 Propoxyl CH 3 H CH 3 4-naphthyl viscous ─ ───────────────────────────────────

【００２２】得られた化合物のＮＭＲデーターは以下の
とおりである。 化合物No.5の1H-NMRデータ(CDCl3)；1.66(3H,d), 3.71
(3H,s), 5.36(1H,q), 7.02(1H,dd), 7.17(1H,d), 7.35
(1H,dd), 7.48(1H,dd), 7.58(1H,dd), 7.65(1H,s),8.19
(1H,s), 8.33(1H,d) 化合物No.6の1H-NMRデータ(CDCl3)；1.6(3H,d), 3.41(3
H), 3.6(3H), 4.6(1H),5.1(1H), 5.38(1H,q), 7.2-7.7
(8H), 8.18(1H,s) 化合物No.10の1H-NMRデータ(CDCl3)；1.64(3H,d), 3.69
(3H,s), 5.35(1H,q), 7.02(1H,dd), 7.18(1H,d), 7.33
(1H,dd), 7.51(2H,d), 7.62(2H,d), 8.19(1H,s),8.31(1
H,d), 9.85(1H,b)The NMR data of the obtained compound are as follows. 1H-NMR data (CDCl 3 ) of compound No. 5; 1.66 (3H, d), 3.71
(3H, s), 5.36 (1H, q), 7.02 (1H, dd), 7.17 (1H, d), 7.35
(1H, dd), 7.48 (1H, dd), 7.58 (1H, dd), 7.65 (1H, s), 8.19
(1H, s), 8.33 (1H, d) 1H-NMR data (CDCl 3 ) of compound No. 6; 1.6 (3H, d), 3.41 (3
H), 3.6 (3H), 4.6 (1H), 5.1 (1H), 5.38 (1H, q), 7.2-7.7
(8H), 8.18 (1H, s) Compound No. 10 1H-NMR data (CDCl 3 ); 1.64 (3H, d), 3.69
(3H, s), 5.35 (1H, q), 7.02 (1H, dd), 7.18 (1H, d), 7.33
(1H, dd), 7.51 (2H, d), 7.62 (2H, d), 8.19 (1H, s), 8.31 (1
H, d), 9.85 (1H, b)

【００２３】化合物No.11の1H-NMRデータ(CDCl3)；1.60
(3H,d), 3.40(3H), 3.55(3H), 4.45-4.65(1H), 5.0-5.2
(1H), 5.37(1H,q), 7.2-7.4(3H), 7.47(2H,d), 7.61(2
H,d), 7.65(1H,d), 8.18(1H,s) 化合物No.12の1H-NMRデータ(CDCl3)；1.08(3H,t), 1.60
(3H,d),3.5(1H), 3.56(3H), 3.75(1H), 5.38(1H,q), 7.
10(1H,d), 7.2-7.4)2H), 7.47(2H,d), 7.60(2H,d), 7.7
5(1H), 8.17(1H,s) 化合物No.13の1H-NMRデータ(CDCl3)；1.6(3H,d), 3.55
(3H), 4.1(1H), 4.5(1H),5.38(1H,q), 7.2-7.8(10H),
8.2(1H,s)1H-NMR data (CDCl 3 ) of compound No. 11; 1.60
(3H, d), 3.40 (3H), 3.55 (3H), 4.45-4.65 (1H), 5.0-5.2
(1H), 5.37 (1H, q), 7.2-7.4 (3H), 7.47 (2H, d), 7.61 (2
H, d), 7.65 (1H, d), 8.18 (1H, s) 1H-NMR data (CDCl 3 ) of compound No. 12; 1.08 (3H, t), 1.60
(3H, d), 3.5 (1H), 3.56 (3H), 3.75 (1H), 5.38 (1H, q), 7.
10 (1H, d), 7.2-7.4) 2H), 7.47 (2H, d), 7.60 (2H, d), 7.7
5 (1H), 8.17 (1H, s) 1H-NMR data (CDCl 3 ) of compound No. 13; 1.6 (3H, d), 3.55
(3H), 4.1 (1H), 4.5 (1H), 5.38 (1H, q), 7.2-7.8 (10H),
8.2 (1H, s)

【００２４】化合物No.14の1H-NMRデータ(CDCl3)；1.6
(3H,d), 3.1(3H), 3.6(3H), 5.38(1H,q), 7.15(1H), 7.
2-7.4(2H), 7.48(2H,d), 7.6(3H,d), 7.7(1H), 8.16(1
H,s) 化合物No.15の1H-NMRデータ(CDCl3)；0.85(3H), 1.5(2
H), 1.6(3H,d), 3.3(2H),3.55(3H), 5.4(1H), 7.1(1H),
7.2-7.4(2H), 7.48(2H,d), 7.6(2H,d), 7.7(1H), 8.18
(1H) 化合物No.16の1H-NMRデータ(CDCl3)；0.88(3H,d), 1.25
(3H,d), 1.60(3H,d), 3.57(3H), 4.5(1H), 5.4(1H), 7.
1(1H,d), 7.2-7.4(2H), 7.48(2H,d), 7.59(2H,d), 7.75
(1H), 8.19(1H,d) 化合物No.17の1H-NMRデータ(CDCl3)；1.60(3H,d), 3.57
(3H), 3.9(1H), 4.3(1H), 5.07(2H), 5.38(1H), 3.82(1
H), 7.11(1H,d), 7.2-7.4(2H), 7.48(2H,d), 7.61(2H,
d), 7.70(1H,d), 8.16(1H,s)1 H-NMR data (CDCl 3 ) of compound No. 14; 1.6
(3H, d), 3.1 (3H), 3.6 (3H), 5.38 (1H, q), 7.15 (1H), 7.
2-7.4 (2H), 7.48 (2H, d), 7.6 (3H, d), 7.7 (1H), 8.16 (1
H, s) 1H-NMR data (CDCl 3 ) of compound No. 15; 0.85 (3H), 1.5 (2
H), 1.6 (3H, d), 3.3 (2H), 3.55 (3H), 5.4 (1H), 7.1 (1H),
7.2-7.4 (2H), 7.48 (2H, d), 7.6 (2H, d), 7.7 (1H), 8.18
(1H) 1H-NMR data (CDCl 3 ) of compound No. 16; 0.88 (3H, d), 1.25
(3H, d), 1.60 (3H, d), 3.57 (3H), 4.5 (1H), 5.4 (1H), 7.
1 (1H, d), 7.2-7.4 (2H), 7.48 (2H, d), 7.59 (2H, d), 7.75
(1H), 8.19 (1H, d) 1H-NMR data (CDCl 3 ) of compound No. 17; 1.60 (3H, d), 3.57
(3H), 3.9 (1H), 4.3 (1H), 5.07 (2H), 5.38 (1H), 3.82 (1
H), 7.11 (1H, d), 7.2-7.4 (2H), 7.48 (2H, d), 7.61 (2H,
d), 7.70 (1H, d), 8.16 (1H, s)

【００２５】化合物No.18の1H-NMRデータ(CDCl3)；1.6
(3H,d), 3.58((3H), 3.7(3H), 4.2-4.6(2H), 5.4(1H),
7.2-7.7(8H), 8.3(1H) 化合物No.19の1H-NMRデータ(CDCl3)；1.65(3H,d), 2.37
(3H,s), 3.76(3H,s), 5.3(1H,q), 7.0-7.4(7H), 8.16(1
H,s), 8.3(1H,d), 10.1(1H,b) 化合物No.22の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.36
(3H,s), 3.42(3H), 3.6(3H), 4.6(1H), 5.2(1H), 5.3(1
H,q), 7.1-7.4(7H), 7.7(1H), 8.16(1H,s) 化合物No.23の1H-NMRデータ(CDCl3)；1.64(3H,d), 3.73
(3H,s), 5.32(1H,q), 7.0(1H, dd), 7.1-7.4(6H), 8.18
(1H,s), 8.3(1H,d), 9.9(1H,b)1H-NMR data (CDCl 3 ) of compound No. 18; 1.6
(3H, d), 3.58 ((3H), 3.7 (3H), 4.2-4.6 (2H), 5.4 (1H),
7.2-7.7 (8H), 8.3 (1H) 1H-NMR data (CDCl 3 ) of compound No. 19; 1.65 (3H, d), 2.37
(3H, s), 3.76 (3H, s), 5.3 (1H, q), 7.0-7.4 (7H), 8.16 (1
H, s), 8.3 (1H, d), 10.1 (1H, b) 1H-NMR data (CDCl 3 ) of compound No. 22; 1.59 (3H, d), 2.36
(3H, s), 3.42 (3H), 3.6 (3H), 4.6 (1H), 5.2 (1H), 5.3 (1
H, q), 7.1-7.4 (7H), 7.7 (1H), 8.16 (1H, s) 1H-NMR data (CDCl 3 ) of compound No.23; 1.64 (3H, d), 3.73
(3H, s), 5.32 (1H, q), 7.0 (1H, dd), 7.1-7.4 (6H), 8.18
(1H, s), 8.3 (1H, d), 9.9 (1H, b)

【００２６】化合物No.24の1H-NMRデータ(CDCl3)；1.59
(3H,d), 3.41(3H), 3.6(3H), 4.6(1H), 5.1(1H), 5.35
(1H,q), 7.1-7.4(7H), 7.7(1H), 8.17(1H,s) 化合物No.26の1H-NMRデータ(CDCl3)；1.65(3H,d), 2.35
(3H,s), 3.76(3H,s), 5.29(1H,q), 7.0(1H,dd), 7.1-7.
4(6H), 7.15(1H,s), 8.33(1H,d), 10.1(1H,b) 化合物No.27の1H-NMRデータ(CDCl3)；1.09(3H,t), 1.60
(3H,d), 2.34(3H,s), 3.5(1H), 3.57(3H), 75(1H), 5.3
3(1H,q), 7.05-7.2(3H), 7.2-7.4(4H), 7.78(1H,d), 8.
15(1H,s) 化合物No.28の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.34
(3H,s), 3.42(3H), 3.59(3H), 4.55(1H), 5.15(1H), 5.
3(1H,q), 7.1-7.4(7H), 7.7(1H), 8.14(1H,s)1H-NMR data (CDCl 3 ) of compound No. 24: 1.59
(3H, d), 3.41 (3H), 3.6 (3H), 4.6 (1H), 5.1 (1H), 5.35
(1H, q), 7.1-7.4 (7H), 7.7 (1H), 8.17 (1H, s) 1H-NMR data (CDCl 3 ) of compound No.26; 1.65 (3H, d), 2.35
(3H, s), 3.76 (3H, s), 5.29 (1H, q), 7.0 (1H, dd), 7.1-7.
4 (6H), 7.15 (1H, s), 8.33 (1H, d), 10.1 (1H, b) Compound No. 27 1H-NMR data (CDCl 3 ); 1.09 (3H, t), 1.60
(3H, d), 2.34 (3H, s), 3.5 (1H), 3.57 (3H), 75 (1H), 5.3
3 (1H, q), 7.05-7.2 (3H), 7.2-7.4 (4H), 7.78 (1H, d), 8.
15 (1H, s) Compound No. 28 1H-NMR data (CDCl 3 ); 1.59 (3H, d), 2.34
(3H, s), 3.42 (3H), 3.59 (3H), 4.55 (1H), 5.15 (1H), 5.
3 (1H, q), 7.1-7.4 (7H), 7.7 (1H), 8.14 (1H, s)

【００２７】化合物No.29の1H-NMRデータ(CDCl3)；1.63
(3H,d), 3.76(3H,s), 5.27(1H,q),7.01(1H,dd), 7.17(1
H,d), 7.2-7.4(5H), 8.17(1H,s), 8.32(1H,d) 化合物No.30の1H-NMRデータ(CDCl3)；4.45-4.7(1H), 5.
0-5.2(1H), 5.3(1H,q),7.2-7.4(7H), 7.7(1H,d), 8.16
(1H,s) 化合物No.33の1H-NMRデータ(CDCl3)；1.57(3H,d), 3.44
(3H,br), 3.60(3H,br),4.6(1H,br), 5.1(1H,br), 5.29
(1H,q), 7.19-7.4(7H,m), 7.7(1H,m), 8.15(1H,s)1 H-NMR data (CDCl 3 ) of compound No. 29; 1.63
(3H, d), 3.76 (3H, s), 5.27 (1H, q), 7.01 (1H, dd), 7.17 (1
H, d), 7.2-7.4 (5H), 8.17 (1H, s), 8.32 (1H, d) 1H-NMR data (CDCl 3 ) of compound No. 30; 4.45-4.7 (1H), 5.
0-5.2 (1H), 5.3 (1H, q), 7.2-7.4 (7H), 7.7 (1H, d), 8.16
(1H, s) 1H-NMR data (CDCl3) of compound No.33; 1.57 (3H, d), 3.44
(3H, br), 3.60 (3H, br), 4.6 (1H, br), 5.1 (1H, br), 5.29
(1H, q), 7.19-7.4 (7H, m), 7.7 (1H, m), 8.15 (1H, s)

【００２８】化合物No.44の1H-NMRデータ(CDCl3)；3.42
(3H,br), 3.60(3H,br), 4.63(1H,br),5.15(1H,br), 5.2
4(2H,s), 7.2-7.8(8H,m), 8.20(1H,s) 化合物No.45の1H-NMRデータ(CDCl3)；2.35(3H,s), 3.42
(3H,s), 3.6(3H,br), 4.6(1H,br), 5.15(2H,s), 5.18(1
H,br), 7.15-7.4(7H,m), 7.8(1H,d), 8.16(1H,s) 化合物No.46の1H-NMRデータ(CDCl3)；3.42(3H,br), 3.6
0(3H,br), 4.63(1H,br),5.1(1H,br), 5.21(2H,s), 7.2-
7.8(8H,m), 8.20(1H,s) 化合物No.47の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.2
(1H,br), 2.34(3H,s), 3.59(3H,br), 4.1(1H,br), 4.5
(1H,br), 5.30(1H,q), 7.15(2H,d), 7.2-7.4(5H,m), 7.
74(1H,m), 8.15(1H,s)1H-NMR data (CDCl3) of compound No.44; 3.42
(3H, br), 3.60 (3H, br), 4.63 (1H, br), 5.15 (1H, br), 5.2
4 (2H, s), 7.2-7.8 (8H, m), 8.20 (1H, s) 1H-NMR data (CDCl3) of compound No.45; 2.35 (3H, s), 3.42
(3H, s), 3.6 (3H, br), 4.6 (1H, br), 5.15 (2H, s), 5.18 (1
H, br), 7.15-7.4 (7H, m), 7.8 (1H, d), 8.16 (1H, s) 1H-NMR data (CDCl3) of compound No.46; 3.42 (3H, br), 3.6
0 (3H, br), 4.63 (1H, br), 5.1 (1H, br), 5.21 (2H, s), 7.2-
7.8 (8H, m), 8.20 (1H, s) 1H-NMR data (CDCl3) of compound No.47; 1.59 (3H, d), 2.2
(1H, br), 2.34 (3H, s), 3.59 (3H, br), 4.1 (1H, br), 4.5
(1H, br), 5.30 (1H, q), 7.15 (2H, d), 7.2-7.4 (5H, m), 7.
74 (1H, m), 8.15 (1H, s)

【００２９】化合物No.48の1H-NMRデータ(CDCl3)；3.42
(3H,br), 3.6(3H,br), 4.65(1H,br),5.13(1H,br), 5.15
(2H,s), 7.2-7.4(7H,m), 7.75(1H,d), 8.17(1H,s) 化合物No.49の1H-NMRデータ(CDCl3)；1.57(3H,d), 2.22
(1H,br), 3.58(3H,br),4.1(1H,br), 4.5(1H,br), 5.3(1
H,q), 7.25-7.4(7H,m), 7.7(1H,m), 8.17(1H,s 化合物No.50の1H-NMRデータ(CDCl3)；1.57(3H,d), 2.13
(3H,s), 3.57(3H,br), 4.4(1H,br), 4.95(1H,br), 5.3
(1H,q), 7.2-7.4(7H,m), 7.7(1H,m), 8.65(1H,s) 化合物No.52の1H-NMRデータ(CDCl3)；3.43(3H,br), 3.6
2(3H,br), 4.65(1H,br),5.1(1H,br), 5.28(2H,br), 7.2
-7.5(3H,m), 7.75(1H,d), 7.8-7.9(3H,m), 8.23(1H,s)1H-NMR data (CDCl3) of compound No. 48; 3.42
(3H, br), 3.6 (3H, br), 4.65 (1H, br), 5.13 (1H, br), 5.15
(2H, s), 7.2-7.4 (7H, m), 7.75 (1H, d), 8.17 (1H, s) 1H-NMR data (CDCl3) of compound No.49; 1.57 (3H, d), 2.22
(1H, br), 3.58 (3H, br), 4.1 (1H, br), 4.5 (1H, br), 5.3 (1
H, q), 7.25-7.4 (7H, m), 7.7 (1H, m), 8.17 (1H, s 1H-NMR data (CDCl3) of compound No.50; 1.57 (3H, d), 2.13
(3H, s), 3.57 (3H, br), 4.4 (1H, br), 4.95 (1H, br), 5.3
(1H, q), 7.2-7.4 (7H, m), 7.7 (1H, m), 8.65 (1H, s) 1H-NMR data (CDCl3) of compound No. 52; 3.43 (3H, br), 3.6
2 (3H, br), 4.65 (1H, br), 5.1 (1H, br), 5.28 (2H, br), 7.2
-7.5 (3H, m), 7.75 (1H, d), 7.8-7.9 (3H, m), 8.23 (1H, s)

【００３０】化合物No.53の1H-NMRデータ(CDCl3)；3.42
(3H,br), 3.61(3H,br), 3.82(3H,s),4.62(1H,br), 5.16
(1H,br), 5.17(2H,s), 6.85(1H,dd), 6.95(1H,d), 6.98
(1H,d), 7.2-7.4(4H,m), 7.8(1H,m), 8.18(1H,s) 化合物No.54の1H-NMRデータ(CDCl3)；1.61(3H,d), 3.42
(3H,br), 3.59(3H,br),3.87(3H,s), 3.91(3H,s), 4.55
(1H,br), 5.2(1H,br), 5.26(1H,q), 6.83(1H,d),6.92(1
H,s), 6.94(1H,d), 7.2-7.4(3H,m), 7.75(1H,m), 8.15
(1H,s) 化合物No.55の1H-NMRデータ(CDCl3)；1.56(3H,d), 3.42
(3H,br), 3.6(3H,br), 4.24(4H,s), 4.6(1H,br), 5.15
(1H,br), 5.22(1H,q), 6.8-6.9(3H,m), 7.2-7.4(3H,m),
7.75(1H,m), 8.13(1H,s)1H-NMR data (CDCl3) of compound No. 53; 3.42
(3H, br), 3.61 (3H, br), 3.82 (3H, s), 4.62 (1H, br), 5.16
(1H, br), 5.17 (2H, s), 6.85 (1H, dd), 6.95 (1H, d), 6.98
(1H, d), 7.2-7.4 (4H, m), 7.8 (1H, m), 8.18 (1H, s) 1H-NMR data (CDCl3) of compound No. 54; 1.61 (3H, d), 3.42
(3H, br), 3.59 (3H, br), 3.87 (3H, s), 3.91 (3H, s), 4.55
(1H, br), 5.2 (1H, br), 5.26 (1H, q), 6.83 (1H, d), 6.92 (1
H, s), 6.94 (1H, d), 7.2-7.4 (3H, m), 7.75 (1H, m), 8.15
(1H, s) 1H-NMR data (CDCl3) of compound No.55; 1.56 (3H, d), 3.42
(3H, br), 3.6 (3H, br), 4.24 (4H, s), 4.6 (1H, br), 5.15
(1H, br), 5.22 (1H, q), 6.8-6.9 (3H, m), 7.2-7.4 (3H, m),
7.75 (1H, m), 8.13 (1H, s)

【００３１】化合物No.56の1H-NMRデータ(CDCl3)；1.56
(3H,d), 3.42(3H,br), 3.6(3H,br), 4.6(1H,br), 5.2(1
H,br), 5.23(1H,q), 5.94(2H,s), 6.75-6.9(3H,m), 7.2
-7.4(3H,m), 7.7(1H,m), 8.13(1H,s) 化合物No.57の1H-NMRデータ(CDCl3)；2.3(1H,br), 3.6
(3H,br), 4.2(1H,br), 4.5(1H,br), 5.24(2H,s), 7.3-
7.8(7H,m), 8.24(1H,s) 化合物No.58の1H-NMRデータ(CDCl3)；2.22(1H,br), 3.6
(3H,br), 4.2(1H,br), 4.5(1H,br), 5.21(2H,s), 7.3-
7.8(7H,m), 8.23(1H,s) 化合物No.59の1H-NMRデータ(CDCl3)；1.60(3H,d), 2.2
(1H,br), 3.6(3H,br), 3.80(3H,s), 4.1(1H,br), 4.5(1
H,br), 5.3(1H,br), 6.89(2H,d), 7.3-7.4(5H,m),7.75
(1H,m), 8.15(1H,s)1H-NMR data (CDCl3) of compound No. 56; 1.56
(3H, d), 3.42 (3H, br), 3.6 (3H, br), 4.6 (1H, br), 5.2 (1
H, br), 5.23 (1H, q), 5.94 (2H, s), 6.75-6.9 (3H, m), 7.2
-7.4 (3H, m), 7.7 (1H, m), 8.13 (1H, s) 1H-NMR data (CDCl3) of compound No.57; 2.3 (1H, br), 3.6
(3H, br), 4.2 (1H, br), 4.5 (1H, br), 5.24 (2H, s), 7.3-
7.8 (7H, m), 8.24 (1H, s) 1H-NMR data (CDCl3) of compound No.58; 2.22 (1H, br), 3.6
(3H, br), 4.2 (1H, br), 4.5 (1H, br), 5.21 (2H, s), 7.3-
7.8 (7H, m), 8.23 (1H, s) Compound No.59 1H-NMR data (CDCl3); 1.60 (3H, d), 2.2
(1H, br), 3.6 (3H, br), 3.80 (3H, s), 4.1 (1H, br), 4.5 (1
H, br), 5.3 (1H, br), 6.89 (2H, d), 7.3-7.4 (5H, m), 7.75
(1H, m), 8.15 (1H, s)

【００３２】化合物No.60の1H-NMRデータ(CDCl3)；1.40
(3H,t), 1.59(3H,d), 2.2(1H,br), 3.6(3H,br), 4.02(2
H,q), 4.15(1H,br), 4.5(1H,br), 5.28(1H,q), 6.87(2
H,d), 7.3-7.4(5H,m), 7.75(1H,m), 8.15(1H,s) 化合物No.61の1H-NMRデータ(CDCl3)；1.02(3H,t), 1.58
(3H,d), 1.8(2H,m), 3.6(3H,br), 3.9(2H,t), 4.1(1H,b
r), 4.5(1H,br), 5.18(1H,q), 6.87(2H,d), 7.3-7.4(5
H,m), 7.75(1H,m), 8.16(1H,s) 化合物No.62の1H-NMRデータ(CDCl3)；1.32(6H,d), 1.59
(3H,d), 2.2(1H,m), 3.6(3H,br), 4.02(1H,br), 4.5(1
H,br), 4.55(1H,m), 5.28(1H,q), 6.86(2H,d), 7.2-7.4
(5H,m), 7.75(1H,m), 8.15(1H,s)1H-NMR data (CDCl3) of compound No. 60: 1.40
(3H, t), 1.59 (3H, d), 2.2 (1H, br), 3.6 (3H, br), 4.02 (2
H, q), 4.15 (1H, br), 4.5 (1H, br), 5.28 (1H, q), 6.87 (2
H, d), 7.3-7.4 (5H, m), 7.75 (1H, m), 8.15 (1H, s) 1H-NMR data (CDCl3) of compound No. 61; 1.02 (3H, t), 1.58
(3H, d), 1.8 (2H, m), 3.6 (3H, br), 3.9 (2H, t), 4.1 (1H, b
r), 4.5 (1H, br), 5.18 (1H, q), 6.87 (2H, d), 7.3-7.4 (5
H, m), 7.75 (1H, m), 8.16 (1H, s) 1H-NMR data (CDCl3) of compound No.62; 1.32 (6H, d), 1.59
(3H, d), 2.2 (1H, m), 3.6 (3H, br), 4.02 (1H, br), 4.5 (1
H, br), 4.55 (1H, m), 5.28 (1H, q), 6.86 (2H, d), 7.2-7.4
(5H, m), 7.75 (1H, m), 8.15 (1H, s)

【００３３】化合物No.63の1H-NMRデータ(CDCl3)；1.24
(3H,t), 1.60(3H,d), 2.20(1H,m), 2.63(1H,q), 3.58(3
H,s), 4.05(1H,m), 4.5(1H,m), 5.30(1H,q), 7.18(2H,
d), 7.28(2H,d), 7.2-7.4(3H,m), 7.75(1h,t), 8.18(1
H,s) 化合物No.64の1H-NMRデータ(CDCl3)；1.31(9H,s), 1.61
(3H,d), 2.18(1H,dd), 3.57(3H,s), 4.0(1H,m), 4.5(1
H,m), 5.32(1H,q), 7.2-7.4(7H,m), 7.74(1H,dd),8.16
(1H,s) 化合物No.65の1H-NMRデータ(CDCl3)；1.60(3H,d), 2.21
(1H,dd), 2.52(1H,dd),3.58(3H,s), 4.0(1H,m), 4.5(1
H,m), 4.68(2H,d), 5.30(1H,q), 6.96(2H,d), 7.3-7.4
(5H,m), 7.75(1H,dd), 8.16(1H,s)1 H-NMR data (CDCl3) of Compound No. 63; 1.24
(3H, t), 1.60 (3H, d), 2.20 (1H, m), 2.63 (1H, q), 3.58 (3
H, s), 4.05 (1H, m), 4.5 (1H, m), 5.30 (1H, q), 7.18 (2H,
d), 7.28 (2H, d), 7.2-7.4 (3H, m), 7.75 (1h, t), 8.18 (1
H, s) 1H-NMR data (CDCl3) of compound No. 64; 1.31 (9H, s), 1.61
(3H, d), 2.18 (1H, dd), 3.57 (3H, s), 4.0 (1H, m), 4.5 (1
H, m), 5.32 (1H, q), 7.2-7.4 (7H, m), 7.74 (1H, dd), 8.16
(1H, s) 1H-NMR data (CDCl3) of compound No.65; 1.60 (3H, d), 2.21
(1H, dd), 2.52 (1H, dd), 3.58 (3H, s), 4.0 (1H, m), 4.5 (1
H, m), 4.68 (2H, d), 5.30 (1H, q), 6.96 (2H, d), 7.3-7.4
(5H, m), 7.75 (1H, dd), 8.16 (1H, s)

【００３４】化合物No.66の1H-NMRデータ(CDCl3)；1.58
(3H,d), 2.2(1H,dd), 3.5(3H), 4.1(1H,m), 4.5(1H,m),
5.33(1H,q), 7.19(2H,d), 7.28-7.4(5H,m), 7.7(1H,d
d), 8.18(1H,s) 化合物No.67の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.2
(1H,dd), 3.59(3H), 4.1(1H,m), 4.5(1H,m), 5.36(1H,
q), 6.93(2H,d), 7.25-7.4(5H,m), 7.73(1H,t), 8.16(1
H,s) 化合物No.68の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.2
(1H,dd), 3.58(3H), 4.05(1H,m), 4.40(2H,t), 4.5(1H,
m), 5.3(1H,q), 6.93(2H,d), 7.25-7.4(5H,m), 7.72(1
H,t), 8.17(1H,s)1H-NMR data (CDCl3) of compound No. 66; 1.58
(3H, d), 2.2 (1H, dd), 3.5 (3H), 4.1 (1H, m), 4.5 (1H, m),
5.33 (1H, q), 7.19 (2H, d), 7.28-7.4 (5H, m), 7.7 (1H, d
d), 8.18 (1H, s) 1H-NMR data (CDCl3) of compound No.67; 1.59 (3H, d), 2.2
(1H, dd), 3.59 (3H), 4.1 (1H, m), 4.5 (1H, m), 5.36 (1H,
q), 6.93 (2H, d), 7.25-7.4 (5H, m), 7.73 (1H, t), 8.16 (1
H, s) 1H-NMR data (CDCl3) of compound No.68; 1.59 (3H, d), 2.2
(1H, dd), 3.58 (3H), 4.05 (1H, m), 4.40 (2H, t), 4.5 (1H,
m), 5.3 (1H, q), 6.93 (2H, d), 7.25-7.4 (5H, m), 7.72 (1
H, t), 8.17 (1H, s)

【００３５】化合物No.69の1H-NMRデータ(CDCl3)；1.59
(3H,d), 2.22(1H,d), 3.56(3H,br), 4.1(1H,br), 4.5(1
H,br), 5.35(1H,q), 7.24(2H,d), 7.25-7.4(3H,m), 7.4
5(2H,d), 7.7(1H,br), 8.19(1H,s) 化合物No.70の1H-NMRデータ(CDCl3)；1.59(3H,d), 3.40
(3H,brs), 3.58(3H,br),4.56(1H,brd), 5.1(1H,drd),
5.33(1H,q), 7.22(1H,d), 7.24(2H,d), 7.34(1H,dd),
7.38(1H,dd), 7.68(1H,d), 8.16(1H,s) 化合物No.71の1H-NMRデータ(CDCl3)；1.59(3H,d), 2.22
(1H,d), 3.58(3H,br), 4.1(1H,brt), 4.43(1H,brt), 5.
31(1H,q), 6.54(1H,t), 7.01(1H,dd), 7.12(1H,d), 7.2
0(1H,d), 7.3-7.4(4H,m), 7.7(1H,d), 8.18(1H,s)1H-NMR data (CDCl3) of Compound No. 69; 1.59
(3H, d), 2.22 (1H, d), 3.56 (3H, br), 4.1 (1H, br), 4.5 (1
H, br), 5.35 (1H, q), 7.24 (2H, d), 7.25-7.4 (3H, m), 7.4
5 (2H, d), 7.7 (1H, br), 8.19 (1H, s) 1H-NMR data (CDCl3) of compound No. 70; 1.59 (3H, d), 3.40
(3H, brs), 3.58 (3H, br), 4.56 (1H, brd), 5.1 (1H, drd),
5.33 (1H, q), 7.22 (1H, d), 7.24 (2H, d), 7.34 (1H, dd),
7.38 (1H, dd), 7.68 (1H, d), 8.16 (1H, s) 1H-NMR data (CDCl3) of compound No.71; 1.59 (3H, d), 2.22
(1H, d), 3.58 (3H, br), 4.1 (1H, brt), 4.43 (1H, brt), 5.
31 (1H, q), 6.54 (1H, t), 7.01 (1H, dd), 7.12 (1H, d), 7.2
0 (1H, d), 7.3-7.4 (4H, m), 7.7 (1H, d), 8.18 (1H, s)

【００３６】化合物No.72の1H-NMRデータ(CDCl3)；1.59
(3H,d), 2.22(1H,brd), 3.56(3H,br),4.1(1H,brt), 4.4
8(1H,brt), 5.32(1H,q), 6.49(1H,t), 7.10(2H,d), 7.3
-7.4(3H,m), 7.36(2H,d), 7.7(1H,d), 8.17(1H,s) 化合物No.73の1H-NMRデータ(CDCl3)；1.69(3H,d), 2.2
(1H,dd), 3.56(3H,s), 4.1(1H,dd), 4.3(1H,dd), 5.5(1
H,q), 7.25-7.4(3H,m), 7.45(2H,m), 7.52(1H,dd), 7.7
2(1H,m), 7.8-7.9(4H,m), 8.22(1H,s)1H-NMR data (CDCl3) of compound No. 72: 1.59
(3H, d), 2.22 (1H, brd), 3.56 (3H, br), 4.1 (1H, brt), 4.4
8 (1H, brt), 5.32 (1H, q), 6.49 (1H, t), 7.10 (2H, d), 7.3
-7.4 (3H, m), 7.36 (2H, d), 7.7 (1H, d), 8.17 (1H, s) 1H-NMR data (CDCl3) of Compound No. 73; 1.69 (3H, d), 2.2
(1H, dd), 3.56 (3H, s), 4.1 (1H, dd), 4.3 (1H, dd), 5.5 (1
H, q), 7.25-7.4 (3H, m), 7.45 (2H, m), 7.52 (1H, dd), 7.7
2 (1H, m), 7.8-7.9 (4H, m), 8.22 (1H, s)

【００３７】製剤例１ 表１記載の化合物Ｎｏ．２を２０部、硅藻土７５部、ア
ルキルベンゼンスルホン酸を主成分とする界面活性剤５
部を均一に粉砕混合して水和剤を得た。 製剤例２ 表１記載の化合物NO.３を３０部、”ソルポール”３０
０５Ｘ（東邦化学工業（株）社商標、非イオン系界面活
性剤と陰イオン界面活性剤との混合物）１５部、キシレ
ン２５部、ジメチルフォルムアミド３０部を混合溶解し
て乳剤を得たFormulation Example 1 Compound No. shown in Table 1 2 to 20 parts, diatomaceous earth 75 parts, and a surfactant 5 containing alkylbenzene sulfonic acid as a main component.
The parts were uniformly pulverized and mixed to obtain a wettable powder. Formulation Example 2 30 parts of compound No. 3 shown in Table 1, "Solpol" 30
An emulsion was obtained by mixing and dissolving 15 parts of 05X (trademark of Toho Chemical Industry Co., Ltd., a mixture of a nonionic surfactant and an anionic surfactant), 25 parts of xylene and 30 parts of dimethylformamide.

【００３８】次に、試験例を挙げることにより、本発明
化合物の農園芸用殺菌剤として有用性を明らかにする。 試験例１ 小麦うどんこ病防除効果試験 径６ｃｍのポットに育苗した１〜２葉期のコムギ（品
種：農林６１号）に製剤例１と同様にして調製した水和
剤を水で所定濃度に希釈して、１ポット当たり１０ｍｌ
の割合で茎葉散布した。薬液風乾後、コムギうどんこ病
菌（Erysiphe graminis）に罹病したコムギ葉から得た
胞子懸濁液を噴霧接種した後、温室内に７〜１０日間放
置した。評価は各葉の発病面積比率を査定し下記の式に
より防除価を算出した。結果を下記表２に示す。Next, the usefulness of the compound of the present invention as a fungicide for agricultural and horticultural use will be clarified by giving test examples. Test Example 1 Wheat powdery mildew control effect test A wettable powder prepared in the same manner as in Formulation Example 1 was added to water at a predetermined concentration in 1-2 leaf stage wheat (variety: Norin 61) grown in a pot with a diameter of 6 cm. Dilute to 10ml per pot
The foliage was sprayed at the ratio of. After air-drying with a chemical solution, a spore suspension obtained from wheat leaves infected with wheat powdery mildew (Erysiphe graminis) was spray-inoculated and then left in a greenhouse for 7 to 10 days. For evaluation, the diseased area ratio of each leaf was evaluated and the control value was calculated by the following formula. The results are shown in Table 2 below.

【数１】防除価（％）＝（（無処理区の平均発病面積比
率）−（処理区の平均発病面積比率））×１００／（無
処理区の平均発病面積比率）[Equation 1] Control value (%) = ((average diseased area ratio of untreated plot)-(average diseased area ratio of treated plot)) x 100 / (average diseased area ratio of untreated plot)

【００３９】[0039]

【表５】 表２ ───────────────────────────── 供試化合物Ｎｏ． 有効成分濃度（ｐｐｍ） 防除価（％） ───────────────────────────── ２ ２００ １００ ６ ２００ １００ １１ ２００ １００ １２ ２００ １００ １３ ２００ １００ １４ ２００ １００ １５ ２００ １００ ２２ ２００ １００ ２４ ２００ １００ ２７ ２００ １００ ２８ ２００ １００ ４４ ２００ １００ ４５ ２００ １００ ４６ ２００ １００ ４７ ２００ １００ ４８ ２００ １００ ４９ ２００ １００ ５０ ２００ １００ ５１ ２００ １００ ５２ ２００ １００ ５３ ２００ １００ ５４ ２００ １００ ─────────────────────────────[Table 5] Table 2 ───────────────────────────── Test compound No. Concentration of active ingredient (ppm) Control value (%) ───────────────────────────── 2 200 100 6 6 200 100 11 11 200 100 12 200 100 13 200 200 100 14 200 100 100 15 200 200 100 22 200 100 24 24 200 100 27 200 200 100 28 200 200 100 44 44 200 100 45 200 200 100 46 46 200 100 47 200 100 100 48 200 100 49 200 200 100 50 200 100 51 200 200 52 53 200 100 54 54 100 100 ──────────────────────────────

【００４０】[0040]

【表６】 表２のつづき ───────────────────────────── 供試化合物Ｎｏ． 有効成分濃度（ｐｐｍ） 防除価（％） ───────────────────────────── ５５ ２００ １００ ５６ ２００ １００ ５７ ２００ １００ ５８ ２００ １００ ５９ ２００ １００ ６０ ２００ １００ ６１ ２００ １００ ６２ ２００ １００ ６３ ２００ １００ ６４ ２００ １００ ６５ ２００ １００ ６６ ２００ １００ ６７ ２００ １００ ６８ ２００ １００ ６９ ２００ １００ ７０ ２００ １００ ７１ ２００ １００ ７２ ２００ １００ ７３ ２００ １００ ───────────────────────────── なお、供試化合物Ｎｏ．は表１の化合物Ｎｏ．に対応す
る。[Table 6] Continuation of Table 2 ───────────────────────────── Test compound No. Concentration of active ingredient (ppm) Control value (%) ───────────────────────────── 55 200 100 100 56 200 200 100 57 57 200 100 58 200 100 59 200 200 100 60 200 200 100 61 200 100 100 62 200 100 63 63 200 100 64 64 200 100 65 200 200 100 66 66 200 100 67 200 200 100 68 68 200 100 69 69 200 100 70 200 200 100 71 200 100 72 72 200 100 73 ──────────────────────────────────────────── — ────────────────────────── Note that the compound No. Is the compound No. of Table 1. Corresponding to.

【００４１】試験例２ 小麦赤さび病防除効果試験 径６ｃｍのポットに育苗した１〜２葉期のコムギ（品
種：農林６１号）に試験例１と同様にして調製した水和
剤を水で所定濃度に希釈して、１ポット当たり１０ｍｌ
の割合で茎葉散布した。薬液風乾後、コムギ赤さび病菌
（Puccinia recondita）に罹病したコムギ葉を摩砕して
得た胞子懸濁液を噴霧接種した後、２２℃の湿室に１５
時間保った後、温室内水槽上に７日間放置した。評価は
各葉の発病面積比率を査定し、下記の式により防除価を
算出した。得られた結果を下記表３に示す。Test Example 2 Wheat Fusarium Head Rust Control Effect Test A wettable powder prepared in the same manner as in Test Example 1 was prescribed with water in 1-2 leaf stage wheat (variety: Norin 61) grown in pots with a diameter of 6 cm. 10ml per pot, diluted to the concentration
The foliage was sprayed at the ratio of. After air-drying with a chemical solution, a spore suspension obtained by grinding wheat leaves infected with wheat leaf rust (Puccinia recondita) was spray-inoculated and then placed in a humid chamber at 22 ° C for 15 minutes.
After being kept for a time, it was left on a water tank in a greenhouse for 7 days. In the evaluation, the diseased area ratio of each leaf was evaluated, and the control value was calculated by the following formula. The results obtained are shown in Table 3 below.

【数２】防除価（％）＝（（無処理区の平均発病面積比
率）−（処理区の平均発病面積比率））×１００／（無
処理区の平均発病面積比率）[Formula 2] Control value (%) = ((average diseased area ratio of untreated plot)-(average diseased area ratio of treated plot)) x 100 / (average diseased area ratio of untreated plot)

【００４２】[0042]

【表７】 表３ ───────────────────────────── 供試化合物Ｎｏ． 有効成分濃度（ｐｐｍ） 防除価（％） ───────────────────────────── ２ ２００ １００ ６ ２００ １００ １１ ２００ １００ １２ ２００ １００ １３ ２００ １００ １４ ２００ １００ １５ ２００ １００ ２２ ２００ １００ ２４ ２００ １００ ２７ ２００ １００ ２８ ２００ １００ ４４ ２００ １００ ４５ ２００ １００ ４６ ２００ １００ ４７ ２００ １００ ４８ ２００ １００ ４９ ２００ １００ ５０ ２００ １００ ５１ ２００ １００ ５２ ２００ １００ ５３ ２００ １００ ５４ ２００ １００ ─────────────────────────────[Table 7] Table 3 ───────────────────────────── Test compound No. Concentration of active ingredient (ppm) Control value (%) ───────────────────────────── 2 200 100 6 6 200 100 11 11 200 100 12 200 100 13 200 200 100 14 200 100 100 15 200 200 100 22 200 100 24 24 200 100 27 200 200 100 28 200 200 100 44 44 200 100 45 200 200 100 46 46 200 100 47 200 100 100 48 200 100 49 200 200 100 50 200 100 51 200 200 52 53 200 100 54 54 100 100 ──────────────────────────────

【００４３】[0043]

【表８】 表３のつづき ───────────────────────────── 供試化合物Ｎｏ． 有効成分濃度（ｐｐｍ） 防除価（％） ───────────────────────────── ５５ ２００ １００ ５６ ２００ １００ ５７ ２００ １００ ５８ ２００ １００ ５９ ２００ １００ ６０ ２００ １００ ６１ ２００ １００ ６２ ２００ １００ ６３ ２００ １００ ６４ ２００ １００ ６５ ２００ １００ ６６ ２００ １００ ６７ ２００ １００ ６８ ２００ １００ ６９ ２００ １００ ７０ ２００ １００ ７１ ２００ １００ ７２ ２００ １００ ７３ ２００ １００ ───────────────────────────── なお、供試化合物Ｎｏ．は表１の化合物Ｎｏ．に対応す
る。[Table 8] Continuation of Table 3 ───────────────────────────── Test compound No. Concentration of active ingredient (ppm) Control value (%) ───────────────────────────── 55 200 100 100 56 200 200 100 57 57 200 100 58 200 100 59 200 200 100 60 200 200 100 61 200 100 100 62 200 100 63 63 200 100 64 64 200 100 65 200 200 100 66 66 200 100 67 200 200 100 68 68 200 100 69 69 200 100 70 200 200 100 71 200 100 72 72 200 100 73 ──────────────────────────────────────────── — ────────────────────────── Note that the compound No. Is the compound No. of Table 1. Corresponding to.

【００４４】[0044]

【発明の効果】かくしてえられる本発明化合物は、いず
れも新規化合物であり優れた殺菌活性を有している。特
に各種植物の病原菌に対して優れた防除効果を有すると
ともに、残効性が長く、植物に対する浸透性にも優れて
いることから、農園芸用殺菌剤として有用である。The compounds of the present invention thus obtained are all novel compounds and have excellent bactericidal activity. In particular, it has an excellent control effect against pathogenic bacteria of various plants, has a long residual effect, and has excellent penetrability to plants, and thus is useful as a fungicide for agricultural and horticultural use.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｄ 317/58 319/18 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display location C07D 317/58 319/18

Claims (2)

【特許請求の範囲】[Claims] 【請求項１】下記一般式（I）で表されるＮ−フェニル
カーバメート誘導体。 【化１】 （上記一般式中、Ｒ1は水素原子、Ｃ1〜Ｃ4のアルキル
基、Ｃ2〜Ｃ5のアルケニル基、Ｃ2〜Ｃ5のアルキニル
基、Ｃ4〜Ｃ7のシクロアルキルアルキル基、Ｃ4〜Ｃ7の
シクロアルコキシアルキル基、Ｃ1〜Ｃ4のハロアルキル
基、Ｃ2〜Ｃ4のアルコキシアルキル基、Ｃ2〜Ｃ4のアル
キルチオアルキル基または−（ＣＲ6Ｒ7） mＣＯＹを表
し（ただし、Ｒ6およびＲ7はそれぞれ独立して水素原子
またはＣ1〜Ｃ2のアルキル基を表し、Ｙは水素原子、Ｃ
1〜Ｃ2のアルキル基、Ｃ1〜Ｃ4のアルコキシ基またはＣ
1〜Ｃ4のアルキルアミノ基を表し、ｍは０または１を表
す）、Ｒ2はＣ1〜Ｃ4のアルキル基を表し、Ｒ3およびＲ
4はそれぞれ独立して水素原子またはＣ1〜Ｃ4のアルキ
ル基を表し、Ｒ5は置換されていてもよいアリール基ま
たはヘテロアリール基を表し、Ｘは水素原子、ハロゲン
原子、Ｃ1〜Ｃ4のアルキル基またはＣ1〜Ｃ4のアルコキ
シ基を表し、ｎは１〜５の整数を表し、ｎが２以上のと
きＸはそれぞれ異なっていてもよい）1. N-phenyl represented by the following general formula (I):
Carbamate derivative. [Chemical 1](In the above general formula, R1Is a hydrogen atom, C1~ CFourThe alkyl
Base, C2~ CFiveAlkenyl group of C2~ CFiveThe alkynyl
Base, CFour~ C7A cycloalkylalkyl group of CFour~ C7of
Cycloalkoxyalkyl group, C1~ CFourThe haloalkyl
Base, C2~ CFourAn alkoxyalkyl group of C2~ CFourThe al
Kirthioalkyl group or-(CR6R7) mShow COY
(However, R6And R7Are each independently a hydrogen atom
Or C1~ C2Represents an alkyl group, Y is a hydrogen atom, C
1~ C2Alkyl group of C1~ CFourAlkoxy group or C
1~ CFourRepresents an alkylamino group, and m represents 0 or 1.
), R2Is C1~ CFourRepresents an alkyl group of R,3And R
FourAre each independently a hydrogen atom or C1~ CFourThe archi
Represents a radical, RFiveIs an optionally substituted aryl group
Or a heteroaryl group, X is a hydrogen atom, halogen
Atom, C1~ CFourAlkyl group or C1~ CFourThe Archoki
Represents a Si group, n represents an integer of 1 to 5, and n is 2 or more.
X may be different) 【請求項２】請求項１記載のＮ−フェニルカーバメート
誘導体を有効成分とする農園芸用殺菌剤2. An agricultural and horticultural fungicide containing the N-phenylcarbamate derivative according to claim 1 as an active ingredient.
JP29678093A 1993-11-26 1993-11-26 N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient Pending JPH07145137A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP29678093A JPH07145137A (en) 1993-11-26 1993-11-26 N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP29678093A JPH07145137A (en) 1993-11-26 1993-11-26 N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient

Publications (1)

Publication Number Publication Date
JPH07145137A true JPH07145137A (en) 1995-06-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
JP29678093A Pending JPH07145137A (en) 1993-11-26 1993-11-26 N-phenylcarbamate derivative and germicide for agriculture and horticulture containing the same derivative as active ingredient

Country Status (1)

Country Link
JP (1) JPH07145137A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002114751A (en) * 2000-08-04 2002-04-16 Aventis Cropscience Sa Fungicidal derivative of phenyl(thio)urea or phenyl(thio) carbamate
EA035913B1 (en) * 2019-02-25 2020-08-31 Вагиф Самед Оглы Гасанов 1-OCTYL-2-(n-BROMOPHENOXY)ETHYL-N-o-TOLYL CARBAMATE EXHIBITING ANTIBACTERIAL AND FUNGICIDAL ACTIVITY

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002114751A (en) * 2000-08-04 2002-04-16 Aventis Cropscience Sa Fungicidal derivative of phenyl(thio)urea or phenyl(thio) carbamate
EA035913B1 (en) * 2019-02-25 2020-08-31 Вагиф Самед Оглы Гасанов 1-OCTYL-2-(n-BROMOPHENOXY)ETHYL-N-o-TOLYL CARBAMATE EXHIBITING ANTIBACTERIAL AND FUNGICIDAL ACTIVITY

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