JPH0543555A - Uracil derivative and pest control agent - Google Patents

Uracil derivative and pest control agent

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Publication number
JPH0543555A
JPH0543555A JP3202914A JP20291491A JPH0543555A JP H0543555 A JPH0543555 A JP H0543555A JP 3202914 A JP3202914 A JP 3202914A JP 20291491 A JP20291491 A JP 20291491A JP H0543555 A JPH0543555 A JP H0543555A
Authority
JP
Japan
Prior art keywords
group
och
alkyl
compound
alkoxy
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
JP3202914A
Other languages
Japanese (ja)
Inventor
Shigeru Ishii
茂 石井
Kazuhiko Akimoto
和彦 穐本
Kazuya Nakayama
和也 中山
Kazuo Yagi
和生 八木
Eiichi Oya
栄一 大屋
Toshiyuki Umehara
利之 梅原
Masaki Kudo
正毅 工藤
Yoichi Inoue
洋一 井上
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.)
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
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 Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP3202914A priority Critical patent/JPH0543555A/en
Publication of JPH0543555A publication Critical patent/JPH0543555A/en
Pending legal-status Critical Current

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  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

PURPOSE:A novel uracil derivative having an excellent insecticidal.acaricidal activity against agricultural chemical insect pests, spider mites, and substantially not affecting mammalians, fishes and useful insects. CONSTITUTION:A compound of formula I [R<1> is H, alkyl, alkenyl, phenyl, CN, NH2, etc.; R<2> is H, halogen, alkyl, OH, alkoxy, CN, NO2, etc.; Z<1>, Z<2> are O, S, NH; X is halogen, alkyl, alkoxy, alkylthio etc.; 1 is 0-5; A is CR<3>R<4>, CR<3>=CR<4>, O, S(O)n, NR11, group of formula II to V; R<3> to R<6> are H, CN, OH, phenyl, alkyl; R<11> is H, alkyl, benzyl, etc.; n is 0-2), etc.; B is group of formula IV (Y is halogen, alkyl, alkenyl, NO2, CN, OH, etc.; n is 0-5), naphthyl, furyl, etc.], e.g. 3-(4-chloro-alpha, alpha-dimethylbenzyl)-6-(2-chlorophenyl)-2, 4-(1H, 3H)- pyrimidinedione.

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、新規なウラシル誘導体
ならびに該誘導体を有効成分として含有する有害生物防
除剤に関するものである。TECHNICAL FIELD The present invention relates to a novel uracil derivative and a pest control agent containing the derivative as an active ingredient.

【０００２】[0002]

【従来の技術】従来、ウラシル化合物に関してはいくつ
かの特許および文献に記載がある。ドイツ特許公報ＤＥ
−２１４２３１７号公報には、１−メチル−３−ベンジ
ル−６−フェニル−２，４（１Ｈ，３Ｈ）−ピリミジン
ジオンが記載されている。また、ジャーナル・オブ・オ
ルガニック・ケミストリー(J. Org. Chem.) 、５５巻、
５１１７頁（１９９０）には、３−ベンジル−６−（２
−ビニル−４，５−ジメトキシフェニル）−２，４−
（１Ｈ，３Ｈ）−ピリミジンジオンおよび３−ベンジル
−６−（２−エチル−４，５−ジメトキシフェニル）−
２，４−（１Ｈ，３Ｈ）−ピリミジンジオンが記載され
ている。2. Description of the Related Art Conventionally, some patents and literatures have described uracil compounds. German patent publication DE
No. 2142317 describes 1-methyl-3-benzyl-6-phenyl-2,4 (1H, 3H) -pyrimidinedione. Also, Journal of Organic Chemistry (J. Org. Chem.), Volume 55,
5117 (1990), 3-benzyl-6- (2
-Vinyl-4,5-dimethoxyphenyl) -2,4-
(1H, 3H) -Pyrimidinedione and 3-benzyl-6- (2-ethyl-4,5-dimethoxyphenyl)-
2,4- (1H, 3H) -pyrimidinedione is described.

【０００３】しかし、上記文献にはこれらの化合物の殺
虫・殺ダニ活性は何ら示されていない。However, the insecticidal and acaricidal activity of these compounds is not shown in the above literature.

【０００４】[0004]

【発明が解決しようとする課題】殺虫剤の長年にわたる
使用により、近年、害虫が抵抗性を獲得し、従来の殺虫
剤による防除が困難になっている。また殺虫剤の一部は
毒性が高く、あるものは残留性により生態系を乱しつつ
ある。よって低毒性かつ低残留性の新規な殺虫剤の開発
が常に期待されている。Due to the long-term use of insecticides, pests have acquired resistance in recent years, making it difficult to control them with conventional insecticides. In addition, some insecticides are highly toxic and some are disturbing the ecosystem due to persistence. Therefore, development of new insecticides with low toxicity and low residue is always expected.

【０００５】[0005]

【課題を解決するための手段】本発明は一般式〔Ｉ〕The present invention has the general formula [I]

【０００６】[0006]

【化８】 [Chemical 8]

【０００７】《式中、R1は水素原子、C1〜C4アルキル
基、C2〜C4アルケニル基、C2〜C4アルキニル基、C1〜C4
ハロアルキル基、C2〜C4アルコキシアルキル基、ホルミ
ル基、C2〜C6アルキルカルボニル基、C2〜C6アルコキシ
カルボニル基、C3〜C6アルコキシカルボニルアルキル
基、C2〜C6シアノアルキル基、ベンジル基、フェニル
基、シアノ基、アミノ基、C3〜C6アルコキシカルボニル
カルボニル基、-SR10 基｛ただし、R10 はC2〜C6アルコ
キシカルボニル基、C1〜C6アルキルスルホニル基、-NR1
1R12基（ただし、R11 はC1〜C6アルキル基を示し、R12
はC1〜C6アルキル基、C2〜C6アルコキシカルボニル基、
C3〜C9アルコキシカルボニルアルキル基、C1〜C6アルキ
ルスルホニル基、C2〜C6アルキルカルボニル基、C3〜C9
ジアルキルアミノカルボニル基、C2〜C6ジアルキルアミ
ノスルホニル基ないし未置換または置換されていてもよ
いフェニル基を示す）、ないし未置換または置換されて
いてもよいフェニル基（ただし、置換されていてもよい
置換基としてはハロゲン原子、シアノ基、ニトロ基、C1
〜C4アルキル基、C1〜C4ハロアルキル基、C1〜C4アルコ
キシ基、C1〜C4ハロアルコキシ基、C1〜C4アルキルチオ
基、C1〜C4ハロアルキルチオ基、C2〜C6アルコキシカル
ボニル基、C2〜C6ハロアルコキシカルボニル基、C2〜C6
アルキルカルボニル基、C2〜C6ハロアルキルカルボニル
基、C1〜C4アルキルスルホニル基またはC1〜C4ハロアル
キルスルホニル基を示し、置換基が２個以上の場合は置
換基は同一であっても異なっていてもよい）を示
す。｝、アルカリ金属またはアルカリ土類金属を示し、
R2は水素原子、ハロゲン原子、C1〜C4アルキル基、C1〜
C4ハロアルキル基、C1〜C4ヒドロキシアルキル基、C2〜
C4アルコキシアルキル基、C2〜C4アルキルチオアルキル
基、チオール基、C1〜C4アルキルチオ基、C1〜C4アルキ
ルスルフィニル基、C1〜C4アルキルスルホニル基、C1〜
C4ハロアルキルチオ基、C1〜C4ハロアルキルスルフィニ
ル基、C1〜C4ハロアルキルスルホニル基、ヒドロキシ
基、C1〜C4アルコキシ基、C1〜C4ハロアルコキシ基、ホ
ルミル基、シアノ基、ニトロ基、アミド基またはチオシ
アネート基を示し、Z1、Z2は各々独立して酸素原子、イ
オウ原子またはイミノ基を示し、Ｘはハロゲン原子、C1
〜C4アルキル基、C1〜C4アルコキシ基、C1〜C4アルキル
チオ基、C1〜C4ハロアルキル基、C1〜C4ハロアルコキシ
基、C1〜C4ハロアルキルチオ基、アミノ基、シアノ基、
またはニトロ基を示し、ｌは０〜５の整数（ただし、２
〜５の場合はＸは同一であっても異なっていてもよい）
を示し、ＡはIn the formula, R 1 is a hydrogen atom, C 1 -C 4 alkyl group, C 2 -C 4 alkenyl group, C 2 -C 4 alkynyl group, C 1 -C 4
Haloalkyl groups, C 2 -C 4 alkoxyalkyl group, formyl group, C 2 -C 6 alkylcarbonyl group, C 2 -C 6 alkoxycarbonyl group, C 3 -C 6 alkoxycarbonylalkyl group, C 2 -C 6 cyanoalkyl group, a benzyl group, a phenyl group, a cyano group, an amino group, C 3 -C 6 alkoxycarbonyl group, -SR 10 group {However, R 10 is C 2 -C 6 alkoxycarbonyl group, C 1 -C 6 alkylsulfonyl Basis, -NR 1
1 R 12 group (provided that R 11 represents a C 1 -C 6 alkyl group, R 12
The C 1 -C 6 alkyl group, C 2 -C 6 alkoxycarbonyl group,
C 3 -C 9 alkoxycarbonylalkyl group, C 1 -C 6 alkylsulfonyl group, C 2 -C 6 alkylcarbonyl group, C 3 -C 9
Dialkylaminocarbonyl group, a C 2 -C 6 dialkylamino sulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (provided that substituted Good substituents include halogen atoms, cyano groups, nitro groups, C 1
-C 4 alkyl group, C 1 -C 4 haloalkyl groups, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy groups, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 haloalkoxycarbonyl groups, C 2 -C 6
An alkylcarbonyl group, a C 2 to C 6 haloalkylcarbonyl group, a C 1 to C 4 alkylsulfonyl group or a C 1 to C 4 haloalkylsulfonyl group, and when two or more substituents are present, the substituents may be the same. May be different). }, Indicating an alkali metal or an alkaline earth metal,
R 2 is a hydrogen atom, a halogen atom, a C 1 to C 4 alkyl group, C 1 to
C 4 haloalkyl group, C 1 -C 4 hydroxyalkyl group, C 2 ~
C 4 alkoxyalkyl group, C 2 -C 4 alkylthioalkyl group, a thiol group, C 1 -C 4 alkylthio group, C 1 -C 4 alkylsulfinyl group, C 1 -C 4 alkylsulfonyl group, C 1 ~
C 4 haloalkylthio group, C 1 -C 4 haloalkylsulfinyl group, C 1 -C 4 haloalkylsulfonyl group, hydroxy group, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy group, a formyl group, a cyano group, A nitro group, an amido group or a thiocyanate group, Z 1 and Z 2 each independently represent an oxygen atom, a sulfur atom or an imino group, and X represents a halogen atom, C 1
-C 4 alkyl group, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkyl groups, C 1 -C 4 haloalkoxy groups, C 1 -C 4 haloalkylthio group, an amino group , Cyano group,
Or represents a nitro group, and l is an integer of 0 to 5 (provided that 2
In the case of ~ 5, X may be the same or different)
And A is

【０００８】[0008]

【化９】 [Chemical 9]

【０００９】[0009]

【化１０】 [Chemical 10]

【００１０】[0010]

【化１１】 [Chemical 11]

【００１１】（ただし、R3〜R10 はそれぞれ独立して、
水素原子、シアノ基、水酸基、フェニル基またはC1〜C6
アルキル基を示し、R11 は水素原子、C1〜C6アルキル
基、C2〜C6アルケニル基、C2〜C6アルキニル基、C2〜C6
アルキルカルボニル基またはベンジル基を示し、ｎは０
〜２の整数を示す。）を示し、Ｂは(However, R 3 to R 10 are independently
Hydrogen atom, cyano group, hydroxyl group, phenyl group or C 1 to C 6
Represents an alkyl group, R 11 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 2 to C 6
Represents an alkylcarbonyl group or a benzyl group, n is 0
Indicates an integer of ˜2. ), B is

【００１２】[0012]

【化１２】 [Chemical formula 12]

【００１３】〔ただし、Ｙはハロゲン原子、C1〜C6アル
キル基、C2〜C6アルケニル基、C2〜C6アルキニル基、C3
〜C6シクロアルキル基、C1〜C6ハロアルキル基、C2〜C6
ハロアルケニル基、C2〜C6ハロアルキニル基、C3〜C6ハ
ロシクロアルキル基、C2〜C6シアノアルキル基、C1〜C6
ヒドロキシアルキル基、C2〜C6カルボキシアルキル基、
C1〜C6アルコキシ基、C2〜C6アルケニルオキシ基、C2〜
C6アルキニルオキシ基、C3〜C6シクロアルキルオキシ
基、C1〜C6ハロアルコキシ基、C2〜C6ハロアルケニルオ
キシ基、C2〜C6ハロアルキニルオキシ基、C3〜C6ハロシ
クロアルコキシ基、C4〜C7ハロシクロアルキルアルコキ
シ基、C1〜C6アルキルチオ基、C2〜C6アルケニルチオ
基、C2〜C6アルキニルチオ基、C3〜C6シクロアルキルチ
オ基、C1〜C6ハロアルキルチオ基、C1〜C6アルキルスル
フィニル基、C2〜C6アルケニルスルフィニル基、C2〜C6
アルキニルスルフィニル基、C3〜C6シクロアルキルスル
フィニル基、C1〜C6ハロアルキルスルフィニル基、C1〜
C6アルキルスルホニル基、C2〜C6アルケニルスルホニル
基、C2〜C6アルキニルスルホニル基、C3〜C6シクロアル
キルスルホニル基、C1〜C6ハロアルキルスルホニル基、
C2〜C6アルコキシアルキル基、C2〜C6アルコキシアルコ
キシ基、C2〜C6ハロアルコキシアルキル基、C2〜C6ハロ
アルコキシアルコキシ基、C2〜C6アルキルチオアルキル
基、C2〜C6アルキルチオアルコキシ基、C3〜C6アルコキ
シカルボニルアルキル基、C3〜C6アルキルカルボニルア
ルキル基、C2〜C6アルコキシカルボニルオキシ基、C2〜
C6アルキルカルボニルオキシ基、C2〜C6アルキルカルボ
ニル基、C3〜C6アルケニルカルボニル基、C3〜C6アルキ
ニルカルボニル基、C4〜C7シクロアルキルカルボニル
基、C2〜C6ハロアルキルカルボニル基、C2〜C6アルコキ
シカルボニル基、C2〜C6ハロアルコキシカルボニル基、
C3〜C6アルコキシカルボニルアルコキシ基、ニトロ基、
シアノ基、ヒドロキシ基、カルボキシル基、チオシアネ
ート基、イソチオシアネート基、C2〜C6チオシアネート
アルキル基、C1〜C6アルキルスルホニルオキシ基、C2〜
C6アルキルチオカルボニル基、メチレンジオキシ基、ハ
ロメチレンジオキシ基、エチレンジオキシ基、ハロエチ
レンジオキシ基、トリメチルシリル基または[Wherein Y is a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 3
To C 6 cycloalkyl group, C 1 to C 6 haloalkyl group, C 2 to C 6
Haloalkenyl group, C 2 -C 6 haloalkynyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 cyanoalkyl group, C 1 -C 6
Hydroxyalkyl group, C 2 -C 6 carboxyalkyl group,
C 1 -C 6 alkoxy group, C 2 -C 6 alkenyloxy group, C 2 ~
C 6 alkynyloxy group, C 3 -C 6 cycloalkyl group, C 1 -C 6 haloalkoxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6 haloalkynyl group, C 3 -C 6 halo cycloalkoxy group, C 4 -C 7 halocycloalkyl alkoxy group, C 1 -C 6 alkylthio group, C 2 -C 6 alkenylthio group, C 2 -C 6 alkynylthio, C 3 -C 6 cycloalkylthio group , C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfinyl group, C 2 -C 6 alkenylsulfinyl group, C 2 -C 6
Alkynylsulfinyl group, C 3 -C 6 cycloalkyl alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 ~
C 6 alkylsulfonyl group, C 2 -C 6 alkenylsulfonyl group, C 2 -C 6 alkynylsulfonyl group, C 3 -C 6 cycloalkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group,
C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkoxyalkoxy, C 2 -C 6 haloalkoxyalkyl group, C 2 -C 6 haloalkoxy alkoxy group, C 2 -C 6 alkylthioalkyl group, C 2 ~ C 6 alkylthioalkoxy group, C 3 -C 6 alkoxycarbonylalkyl group, C 3 -C 6 alkylcarbonyl group, C 2 -C 6 alkoxycarbonyloxy group, C 2 ~
C 6 alkylcarbonyloxy group, C 2 -C 6 alkylcarbonyl group, C 3 -C 6 alkenylcarbonyl group, C 3 -C 6 alkynyl group, C 4 -C 7 cycloalkylcarbonyl group, C 2 -C 6 haloalkyl carbonyl group, C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 haloalkoxycarbonyl groups,
C 3 -C 6 alkoxycarbonylalkoxy group, a nitro group,
Cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C 2 -C 6 thiocyanate alkyl group, C 1 -C 6 alkylsulfonyloxy group, C 2 ~
C 6 alkylthiocarbonyl group, methylenedioxy group, halomethylenedioxy group, ethylenedioxy group, haloethylenedioxy group, trimethylsilyl group or

【００１４】[0014]

【化１３】 [Chemical 13]

【００１５】｛ただし、Ｗは{However, W is

【００１６】[0016]

【化１４】 [Chemical 14]

【００１７】（ただし、R3、R4、R11 およびｎは前記と
同じ意味を示す）を示し、ｑは０または１の整数を示
し、Arは無置換または置換されていてもよいフェニル
基、ナフチル基、フリル基、チエニル基、ピロリル基、
ピラゾリル基、イミダゾリル基、チアゾリル基、イソチ
アゾリル基、オキサゾリル基、イソオキサゾリル基、オ
キサジアゾリル基、チアジアゾリル基、トリアゾリル
基、ピリジル基、ピリダジル基、ピリミジル基、ピラジ
ル基、キノリル基またはキノキザリル基（ただし、置換
されていてもよい置換基としてはハロゲン原子、シアノ
基、ニトロ基、C1〜C4アルキル基、C1〜C4ハロアルキル
基、C1〜C4アルコキシ基、C1〜C4ハロアルキコシ基、C1
〜C4アルキルチオ基、C1〜C4ハロアルキルチオ基、C1〜
C4アルキルスルホニル基、C1〜C4ハロアルキルスルホニ
ル基、C2〜C4アルコキシカルボニル基、カルボキシル
基、アミノ基、モノC1〜C4アルキルアミノ基、ジC1〜C4
アルキルアミノ基、フェニル基、ベンジル基、メチレン
ジオキシ基またはハロメチレンジオキシ基を示し、置換
基が２個以上の場合は置換基は同一であっても異なって
いてもよい）を示す。｝を示し、ｍは０〜５の整数（た
だし、２〜５の場合はＹは同一であっても異なっていて
もよい）を示す。〕または、未置換または置換されてい
てもよいナフチル基、フリル基、チエニル基、ピロリル
基、ピラゾリル基、イミダゾリル基、チアゾリル基、イ
ソチアゾリル基、オキサゾリル基、イソオキサゾリル
基、チアジアゾリル基、オキサジアゾリル基、トリアゾ
リル基、ピリジル基、ピリダジル基、ピリミジル基、ピ
ラジル基、キノリル基、キノキザリル基、ベンゾフリル
基、ベンゾチエニル基、インドリル基、ベンゾオキサゾ
リル基またはベンゾチアゾリル基（ただし、置換されて
いてもよい置換基としてはハロゲン原子、シアノ基、ニ
トロ基、C1〜C4アルキル基、C1〜C4ハロアルキル基、C1
〜C4アルコキシ基、C1〜C4ハロアルコキシ基、C1〜C4ア
ルキルチオ基、C1〜C4ハロアルキルチオ基、C1〜C4アル
キルスルホニル基、C1〜C4ハロアルキルスルホニル基、
C2〜C4アルコキシカルボニル基、カルボキシル基、アミ
ノ基、モノC1〜C4アルキルアミノ基、ジC1〜C4アルキル
アミノ基、フェニル基、フェノキシ基またはベンジル基
を示し、置換基が２個以上の場合は置換基は同一であっ
ても異なっていてもよい）を示し、また１−メチル−３
−ベンジル−６−フェニル−２，４（１Ｈ，３Ｈ）−ピ
リミジンジオン、３−ベンジル−６−（２−ビニル−
４，５−ジメトキシフェニル）−２，４−（１Ｈ，３
Ｈ）−ピリミジンジオンおよび３−ベンジル−６−（２
−エチル−４，５−ジメトキシフェニル）−２，４−
（１Ｈ，３Ｈ）−ピリミジンジオンは除く》で表わされ
るウラシル誘導体および該誘導体の１種または２種以上
を有効成分として含有する有害生物防除剤に関するもの
である。(Wherein R 3 , R 4 , R 11 and n have the same meanings as described above), q represents an integer of 0 or 1, and Ar represents an unsubstituted or optionally substituted phenyl group. , Naphthyl group, furyl group, thienyl group, pyrrolyl group,
Pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group or quinoxalyl group (however, substituted As the substituent which may be, a halogen atom, a cyano group, a nitro group, a C 1 to C 4 alkyl group, a C 1 to C 4 haloalkyl group, a C 1 to C 4 alkoxy group, a C 1 to C 4 haloalkoxy group, C 1
~ C 4 alkylthio group, C 1 ~ C 4 haloalkylthio group, C 1 ~
C 4 alkylsulfonyl group, C 1 to C 4 haloalkylsulfonyl group, C 2 to C 4 alkoxycarbonyl group, carboxyl group, amino group, mono C 1 to C 4 alkylamino group, di C 1 to C 4
It represents an alkylamino group, a phenyl group, a benzyl group, a methylenedioxy group or a halomethylenedioxy group, and when there are two or more substituents, the substituents may be the same or different. }, M is an integer of 0 to 5 (provided that in the case of 2 to 5, Y may be the same or different). ] Or an unsubstituted or optionally substituted naphthyl group, furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group , A pyridyl group, a pyridazyl group, a pyrimidyl group, a pyrazyl group, a quinolyl group, a quinoxalyl group, a benzofuryl group, a benzothienyl group, an indolyl group, a benzoxazolyl group or a benzothiazolyl group (however, as a substituent which may be substituted, halogen atom, a cyano group, a nitro group, C 1 -C 4 alkyl group, C 1 -C 4 haloalkyl groups, C 1
-C 4 alkoxy, C 1 -C 4 haloalkoxy groups, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 4 alkylsulfonyl group, C 1 -C 4 haloalkylsulfonyl group,
C 2 to C 4 alkoxycarbonyl group, carboxyl group, amino group, mono C 1 to C 4 alkylamino group, di C 1 to C 4 alkylamino group, phenyl group, phenoxy group or benzyl group, wherein the substituent is 2 In the case of one or more, the substituents may be the same or different), and 1-methyl-3
-Benzyl-6-phenyl-2,4 (1H, 3H) -pyrimidinedione, 3-benzyl-6- (2-vinyl-
4,5-dimethoxyphenyl) -2,4- (1H, 3
H) -pyrimidinedione and 3-benzyl-6- (2
-Ethyl-4,5-dimethoxyphenyl) -2,4-
The present invention relates to a uracil derivative represented by (excluding (1H, 3H) -pyrimidinedione) and a pest control agent containing one or more of the derivatives as an active ingredient.

【００１８】本発明において有害生物防除剤とは、特に
害虫防除剤を意味する。本発明化合物は極めて低い薬剤
濃度で各種の有害な害虫に対して効力を示す。その害虫
としては、例えば、ツマグロヨコバイ、トビイロウン
カ、モモアカアブラムシ、ニジュウヤホシテントウ、ハ
スモンヨトウ、コブノメイガ、コナガ等の農業害虫、ナ
ミハダニ、ミカンハダニ、カンザワハダニ等のハダニ
類、アカイエカ、イエバエ、チャバネゴキブリ、アリ、
ノミ、シラミ等の衛生害虫、コクゾウムシ、コクヌスト
モドキ、スジマダラメイガ等の貯殻害虫、シロアリのよ
うな家屋害虫、ダニ、ノミ、シラミ等の家畜害虫、コナ
ダニ、ヒョウヒダニ、ツメダニ等の屋内塵性ダニ、ナメ
クジ、カタツムリ等の軟体動物等が挙げられる。すなわ
ち、本発明化合物は直翅目、半翅目、鱗翅目、鞘翅目、
膜翅目、双翅目、シロアリ目およびダニ・シラミ類の害
虫を低濃度で有効に防除できる。一方、本発明化合物は
ホ乳類、魚類、甲殻類および益虫に対してはほとんど悪
影響がない極めて有用な化合物であることを見出し、本
発明を完成した。In the present invention, the pest control agent means especially a pest control agent. The compounds of the present invention are effective against various harmful pests at extremely low drug concentrations. Examples of the pest include agricultural pests such as green leafhoppers, brown planthoppers, green peach aphids, pearl moss, Codworm, mosquitoes, spider mites such as Nami mites, citrus mites, kanzawa mites, mosquitoes, house flies, mosquitoes, and cockroaches.
Sanitary pests such as fleas and lice, storage weevils such as weevil, stag beetle, stag beetle, house pests such as termites, livestock pests such as mites, fleas, lice, indoor dust mites such as mites, leopard mites, and tick mites , Slugs, snails and other mollusks. That is, the compound of the present invention, Orthoptera, hemiptera, Lepidoptera, Coleoptera,
It can effectively control pests of Hymenoptera, Diptera, Termites, and mites and lice at low concentrations. On the other hand, it was found that the compound of the present invention is a very useful compound having almost no adverse effect on mammals, fish, crustaceans and beneficial insects, and completed the present invention.

【００１９】次に本発明化合物の製造法について説明す
る。本発明化合物は新規なウラシル誘導体である。その
合成法としては例えばコンプレヘンシブ ヘテロサイク
リック ケミストリー(Comprehensive Heterocyclic C
hemistry) 、３巻、５７頁 (1984年）等に記載されてい
る合成法等を参考にウラシル骨格を合成することができ
る。上記の方法も含めて製造法を具体的に説明する。Next, a method for producing the compound of the present invention will be described. The compound of the present invention is a novel uracil derivative. The synthesis method is, for example, Comprehensive Heterocyclic C
The uracil skeleton can be synthesized with reference to the synthesis method described in Hemistry), vol. 3, p. 57 (1984) and the like. The manufacturing method including the above method will be specifically described.

【００２０】[0020]

【化１５】 [Chemical 15]

【００２１】[0021]

【化１６】 [Chemical 16]

【００２２】[0022]

【化１７】 [Chemical 17]

【００２３】[0023]

【化１８】 [Chemical 18]

【００２４】式中（Ａ法〜Ｉ法）においてR1、R2、
Xl 、Ａ、Ｂ、Z1およびZ2は前記と同じ意味を示し、R
12 およびR13 はそれぞれ独立をしてC1〜C6アルキル
基、ベンジル基またはフェニル基を示し、R14 はハロゲ
ン原子、ニトロ基またはチオシアネート基を示し、L1お
よびL2はそれぞれ独立してハロゲン原子、メタンスルホ
ネート基、ｐ−トルエンスルホネート基またはC1〜C4ア
ルキル硫酸基のような良好な脱離基を示す。また式〔I
〕、式〔VI〕、式〔VIII〕、式〔XVI〕、式〔XVII〕、
式〔XVIII〕および式〔XIX〕は本発明化合物である。In the formulas (method A to method I), R 1 , R 2 ,
X l , A, B, Z 1 and Z 2 have the same meanings as described above, and R
12 and R 13 each independently represent a C 1 to C 6 alkyl group, a benzyl group or a phenyl group, R 14 represents a halogen atom, a nitro group or a thiocyanate group, L 1 and L 2 are each independently It shows a good leaving group such as a halogen atom, a methane sulfonate group, a p-toluene sulfonate group or a C 1 -C 4 alkylsulfate group. In addition, the formula [I
], Formula [VI], formula [VIII], formula [XVI], formula [XVII],
Formula [XVIII] and formula [XIX] are the compounds of the present invention.

【００２５】Ａ法はR2が水素原子やC1〜C4アルキル基等
の合成に適する方法である。式〔II〕の出発物質は既知
の方法で合成することができる。工程１においては式
〔II〕の化合物と式〔III〕のイソ（チオ）シアネート
類または式〔IV〕の（チオ）カルバミン酸エステル類を
塩基の存在下、不活性な溶媒中で反応させることによ
り、中間体〔V〕を単離することなく、式〔VI〕の本発
明化合物を得ることができる。用いられる塩基としては
ナトリウムエトキシドのようなアルカリ金属アルコキシ
ド類、水酸化ナトリウム、水酸化カリウム等のアルカリ
金属水酸化物、炭酸ナトリウム、炭酸カリウム等のアル
カリ金属炭酸塩または水素化ナトリウム等が挙げられ
る。溶媒としてはメタノール、エタノール等の低級アル
コール類、ベンゼン、トルエン等の芳香族炭化水素類、
ジエチルエーテル、テトラヒドロフラン、1, 4−ジオキ
サン、1, 2−ジメトキシエタン、1, 2−ジエトキシエタ
ン等のエーテル類、ジクロロメタン、1, 2−ジクロロエ
タン等のハロゲン化炭化水素類、ジメチルホルムアミ
ド、ジメチルアセトアミド等のアミド類、アセトニトリ
ル、ジメチルスルホキシドまたはこれらの混合溶媒等が
挙げられる。一般的には式〔II〕のR12と同じアルコー
ル(R12OH)溶媒中で塩基としてナトリウムアルコキシド
(R12ONa)を用いるか、またはテトラヒドロフラン、ジメ
チルホルムアミドまたはジメチルスルホキシド溶媒中で
塩基として水素化ナトリウムを用いるのが好ましい。反
応温度は−60℃から反応混合物の還流温度までの任意の
温度を設定することができる。Method A is a method suitable for synthesizing R 2 as a hydrogen atom or a C 1 -C 4 alkyl group. The starting material of formula [II] can be synthesized by a known method. In step 1, a compound of formula [II] is reacted with an iso (thio) cyanate of formula [III] or a (thio) carbamic acid ester of formula [IV] in the presence of a base in an inert solvent. By this, the compound of the present invention of the formula [VI] can be obtained without isolating the intermediate [V]. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, or sodium hydride. .. As the solvent, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene,
Ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane and 1,2-diethoxyethane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, dimethylformamide, dimethylacetamide And amides thereof, acetonitrile, dimethyl sulfoxide, a mixed solvent thereof, and the like. Generally, sodium alkoxide is used as a base in the same alcohol (R 12 OH) solvent as R 12 of formula [II].
It is preferred to use (R 12 ONa) or to use sodium hydride as the base in a tetrahydrofuran, dimethylformamide or dimethylsulfoxide solvent. The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture.

【００２６】工程２においては式〔VI〕の化合物と式
〔VII〕の化合物を塩基の存在下、不活性な溶媒中で反
応させることにより、式〔VIII〕の本発明化合物を得る
ことができる。R1がC1〜C4アルキル基、C2〜C4アルケニ
ル基、C2〜C4アルキニル基またはC2〜C4アルコキシアル
キル基の場合には式〔VII〕のR1−L1としては各クロラ
イド、ブロマイド等のハライドを使用するのが好まし
い。またR1がC1〜C4アルキル基の場合にはジアルキル硫
酸(R1 2SO4)も適している。用いられる塩基としてはナト
リウムエトキシドのようなアルカリ金属アルコキシド
類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭
酸塩または水素化ナトリウムが好ましい。溶媒としては
水、エタノールのような低級アルコール類、1, 2−ジメ
トキシエタン、テトラヒドロフラン等のエーテル類、ジ
メチルホルムアミドまたはジメチルスルホキシドが好ま
しい。反応温度は０℃から反応混合物の還流温度までの
任意の温度を設定できるが、０℃〜30℃で行なうのが好
ましい。R1がホルミルの場合はR1−L1としてギ酸ハライ
ドを、C2〜C6のアルキルカルボニル基の場合はR1−L1と
してC2〜C6アルカン酸ハライドまたは無水物を、C2〜C6
アルコキシカルボニル基の場合はR1−L1としてC2〜C6ア
ルキルクロロホルメートまたはブロモホルメートを使用
するのが好ましい。用いられる塩基としては水素化ナト
リウムが好ましい。ただし、酸無水物を用いてC2〜C6ア
ルキルカルボニル基を導入する場合には塩基を使用する
ことなく反応を行なうことができる。溶媒としてはジメ
チルホルムアミドまたはジメチルスルホキシドが好まし
い。反応温度は０℃から反応混合物の還流温度までの任
意の温度を設定できるが、０℃から30℃で行うのが好ま
しい。In step 2, the compound of formula [VI] is reacted with the compound of formula [VII] in the presence of a base in an inert solvent to obtain the compound of the present invention of formula [VIII]. .. When R 1 is a C 1 to C 4 alkyl group, a C 2 to C 4 alkenyl group, a C 2 to C 4 alkynyl group or a C 2 to C 4 alkoxyalkyl group, as R 1 -L 1 of the formula [VII] It is preferable to use halides such as chloride and bromide. Further, when R 1 is a C 1 -C 4 alkyl groups are also suitable dialkyl sulfate (R 1 2 SO 4). The base used is preferably an alkali metal alkoxide such as sodium ethoxide, an alkali metal carbonate such as sodium carbonate or potassium carbonate, or sodium hydride. As the solvent, water, lower alcohols such as ethanol, ethers such as 1,2-dimethoxyethane and tetrahydrofuran, dimethylformamide or dimethylsulfoxide are preferable. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 30 ° C. When R 1 is formyl, a formic acid halide is used as R 1 -L 1 , and when it is a C 2 -C 6 alkylcarbonyl group, C 2 -C 6 alkanoic acid halide or anhydride is used as R 1 -L 1 , C 2 ~ C 6
For alkoxycarbonyl group are preferably used C 2 -C 6 alkyl chloroformate or bromo formate as R 1 -L 1. The base used is preferably sodium hydride. However, in the case of introducing a C 2 -C 6 alkylcarbonyl group with an acid anhydride can be carried out the reaction without using a base. The solvent is preferably dimethylformamide or dimethylsulfoxide. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out at 0 ° C to 30 ° C.

【００２７】式〔VI〕化合物でZ1がイオウ原子の場合に
アルキル化すると通常Ｎ−およびＳ−アルキル化生成物
の混合物が生成する。所望のＮ−C1〜C4アルキル−、Ｎ
−C2〜C4アルケニル−、Ｎ−C2〜C4アルキニル−または
Ｎ−C2〜C4アルコキシアルキル体はこのような混合物か
らカラムクロマトグラフィーのような常法により容易に
単離することができる。Alkylation of compounds of formula [VI] where Z 1 is a sulfur atom usually produces a mixture of N- and S-alkylated products. Desired N-C 1 ~C 4 alkyl -, N
-C 2 -C 4 alkenyl -, N-C 2 ~C 4 alkynyl -, or N-C 2 ~C 4 alkoxyalkyl body to conventional methods easily isolated by such as column chromatography from such a mixture You can

【００２８】Ｂ法はウラシル環形成前にR1として水素原
子以外の各種置換基を導入できることに特徴がある。工
程１において式〔IX〕の化合物と式〔X〕の各種アミン
を酸触媒の存在下で反応することにより式〔XI〕の化合
物を得ることができる。用いられる酸としては酢酸また
はトリフルオロ酢酸が好ましい。The method B is characterized in that various substituents other than a hydrogen atom can be introduced as R 1 before the formation of the uracil ring. The compound of formula [XI] can be obtained by reacting the compound of formula [IX] with various amines of formula [X] in step 1 in the presence of an acid catalyst. The acid used is preferably acetic acid or trifluoroacetic acid.

【００２９】工程２においては式〔XI〕の化合物と式
〔III〕のイソ（チオ）シアネート類、または式〔IV〕
の（チオ）カルバミン酸エステル類と塩基の存在下で反
応させることにより式〔XII〕の中間体を単離すること
なく式〔VIII〕の本発明化合物を得ることができる。こ
の工程で用いられる塩基、溶媒および反応温度等の条件
はＡ法の工程２とほぼ同じである。In step 2, a compound of formula [XI] and an iso (thio) cyanate of formula [III], or a compound of formula [IV]
The compound of the present invention of the formula [VIII] can be obtained by the reaction with the (thio) carbamic acid ester of the above in the presence of a base without isolation of the intermediate of the formula [XII]. Conditions such as a base, a solvent and a reaction temperature used in this step are almost the same as those in Step 2 of Method A.

【００３０】Ｃ法においては式〔XIII〕の３−Ｈ−ウラ
シル化合物と式〔XIV〕の化合物を塩基の存在下、不活
性な溶媒中で反応させることにより式〔I 〕の本発明化
合物を得ることができる。用いられる塩基としてはナト
リウムエトキシドのようなアルカリ金属アルコキシド
類、水酸化ナトリウム、水酸化カリウム等のアルカリ金
属水酸化物、炭酸ナトリウム、炭酸カリウム等のアルカ
リ金属炭酸塩または水素化ナトリウム等が挙げられる。
溶媒としてはメタノール、エタノール等の低級アルコー
ル類、ベンゼン、トルエン等の芳香族炭化水素類、ジエ
チルエーテル、テトラヒドロフラン、1, 4−ジオキサ
ン、1, 2−ジメトキシエタン、1, 2−ジエトキシエタン
等のエーテル類、ジクロロメタン、1, 2−ジクロロエタ
ン等のハロゲン化炭化水素類、ジメチルホルムアミド、
ジメチルアセトアミド等のアミド類、アセトニトリル、
ジメチルスルホキシドまたはこれらの混合溶媒等が挙げ
られる。式〔I〕においてＡがIn method C, the 3-H-uracil compound of formula [XIII] is reacted with the compound of formula [XIV] in the presence of a base in an inert solvent to give a compound of the present invention of formula [I]. Obtainable. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, or sodium hydride. ..
Examples of the solvent include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane and the like. Ethers, dichloromethane, halogenated hydrocarbons such as 1,2-dichloroethane, dimethylformamide,
Amides such as dimethylacetamide, acetonitrile,
Dimethyl sulfoxide or a mixed solvent thereof may be used. In formula [I], A is

【００３１】[0031]

【化１９】 [Chemical 19]

【００３２】でR11が水素原子の場合は式〔XIV〕の代わ
りにそれぞれ相当するイソシアネート（Ｂ−Ｎ＝Ｃ＝Ｏ
またはIn the case where R 11 is a hydrogen atom, the corresponding isocyanate (BN-C = O) is used instead of the formula [XIV].
Or

【００３３】[0033]

【化２０】 [Chemical 20]

【００３４】）またはイソチオシアネート（Ｂ−Ｎ＝Ｃ
＝Ｓまたは) Or isothiocyanate (BN--C)
= S or

【００３５】[0035]

【化２１】 [Chemical 21]

【００３６】）を用いるのが好ましい。用いられる塩
基、溶媒および反応温度等の条件は式〔XIV〕を用いる
ときとほぼ同じである。It is preferred to use The conditions such as the base, solvent and reaction temperature used are almost the same as those in the case of using the formula [XIV].

【００３７】Ｄ法はZ2がイミノ基である場合および、そ
れを経てZ2が酸素原子である本発明化合物の合成に適す
る方法である。式〔XV〕の出発原料は既知の方法で合成
することができる。式〔XV〕の化合物と式〔III〕また
は式〔IV〕の化合物を塩基の存在下、不活性な溶媒中で
反応させることにより、式〔XVI〕の本発明化合物を得
ることができる。反応に用いられる塩基、溶媒および反
応温度の条件はＡ法の工程１とほぼ同じである。次に式
〔XVI〕の化合物を酸性の条件下で加水分解することに
より式〔VI〕の本発明化合物を得ることができる。用い
られる酸としては塩酸、硫酸、硝酸等の鉱酸が好まし
く、さらにはそれらの希釈水溶液が好ましい。反応温度
は20℃から反応混合物の還流温度までの任意の温度が設
定できるが、還流温度で行なうのが好ましい。Method D is a method suitable for the case where Z 2 is an imino group and the synthesis of the compound of the present invention through which Z 2 is an oxygen atom. The starting material of the formula [XV] can be synthesized by a known method. The compound of the formula [XVI] can be obtained by reacting the compound of the formula [XV] with the compound of the formula [III] or the formula [IV] in the presence of a base in an inert solvent. The conditions of the base, solvent and reaction temperature used in the reaction are almost the same as those in Step 1 of Method A. Next, the compound of the formula [XVI] is hydrolyzed under acidic conditions to obtain the compound of the present invention of the formula [VI]. As the acid used, mineral acids such as hydrochloric acid, sulfuric acid and nitric acid are preferable, and further dilute aqueous solutions thereof are preferable. The reaction temperature can be set to any temperature from 20 ° C. to the reflux temperature of the reaction mixture, but it is preferably carried out at the reflux temperature.

【００３８】Ｅ法はZ2の酸素原子をイオウ原子に変換す
る方法である。式〔VIII〕の化合物と五硫化リンまたは
ローソン試薬を不活性な溶媒中で反応させることにより
式〔XVII〕の化合物を得ることができる。溶媒としては
テトラヒドロフラン、1,4-ジオキサン、1,2-ジメトキシ
エタン等のエーテル類、ベンゼン、トルエン等の芳香族
炭化水素類、ジメチルホルムアミド、ジメチルスルホキ
シド、ヘキサメチルホスホリックトリアミド等が挙げら
れる。反応温度は20℃から反応混合物の還流温度までの
任意の温度を設定することができるが、還流温度で行う
のが好ましい。Method E is a method of converting oxygen atoms of Z 2 into sulfur atoms. The compound of formula [XVII] can be obtained by reacting the compound of formula [VIII] with phosphorus pentasulfide or Lawesson's reagent in an inert solvent. Examples of the solvent include ethers such as tetrahydrofuran, 1,4-dioxane, and 1,2-dimethoxyethane, aromatic hydrocarbons such as benzene and toluene, dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, and the like. The reaction temperature can be set to any temperature from 20 ° C. to the reflux temperature of the reaction mixture, but it is preferably carried out at the reflux temperature.

【００３９】Ｆ法はR2が水素原子である式〔XVIII〕の
ウラシル誘導体の水素原子をハロゲン原子、ニトロ基ま
たはチオシアネート基に変換して式〔XIX〕の本発明化
合物を得る方法である。ハロゲン化剤としては、塩素化
は塩素、スルフリルクロリドまたはＮ−クロロスクシン
イミドを、臭素化は臭素、スルフリルブロミドまたはＮ
−ブロモスクシンイミドを、ヨウ素化はヨウ素または一
塩化ヨウ素を用いるのが好ましい。溶媒としては酢酸ま
たはジクロロメタン、四塩化炭素等のハロゲン化炭化水
素類を用いるのが好ましい。反応温度は０℃から反応混
合物の還流温度までの任意の温度が設定できるが20℃か
ら還流温度までの範囲で行なうのが好ましい。Method F is a method of converting the hydrogen atom of the uracil derivative of the formula [XVIII] in which R 2 is a hydrogen atom into a halogen atom, a nitro group or a thiocyanate group to obtain the compound of the present invention of the formula [XIX]. As the halogenating agent, chlorination is chlorine, sulfuryl chloride or N-chlorosuccinimide, and bromination is bromine, sulfuryl bromide or N-chlorosuccinimide.
It is preferable to use -bromosuccinimide and iodine or iodine monochloride for iodination. As the solvent, acetic acid or a halogenated hydrocarbon such as dichloromethane or carbon tetrachloride is preferably used. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but it is preferably carried out in the range from 20 ° C to the reflux temperature.

【００４０】ニトロ化剤としては硝酸、硝酸と硫酸の混
合物を用いるのが好ましい。溶媒としてはジクロロメタ
ン、1, 2−ジクロロエタン等のハロゲン化炭化水素類ま
たは酢酸が好ましいが、溶媒を用いなくてもよい。反応
温度は０℃から反応混合物の還流温度までの任意の温度
が設定できるが、０℃から50℃までが好ましい。チオシ
アネート化剤としては、アンモニウムチオシアネートと
臭素を用いてチオシアノゲンを発生させるのが好まし
い。溶媒としてはジクロロメタン、四塩化炭素等のハロ
ゲン化炭化水素類、1, 2−ジメトキシエタン、テトラヒ
ドロフラン等のエーテル類または酢酸を用いるのが好ま
しい。反応温度は０℃から50℃までの任意の温度が設定
できるが、０℃から30℃で行なうのが好ましい。As the nitrating agent, nitric acid or a mixture of nitric acid and sulfuric acid is preferably used. As the solvent, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane or acetic acid are preferable, but the solvent may not be used. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 50 ° C. As the thiocyanating agent, it is preferable to generate thiocyanogen using ammonium thiocyanate and bromine. As the solvent, it is preferable to use halogenated hydrocarbons such as dichloromethane and carbon tetrachloride, ethers such as 1,2-dimethoxyethane and tetrahydrofuran, or acetic acid. The reaction temperature can be set to any temperature from 0 ° C to 50 ° C, but is preferably 0 ° C to 30 ° C.

【００４１】各製造法（Ａ法〜Ｆ法）において、各反応
物質のモル比には特に制限はないが、等モル又はそれに
近い比率で反応を行なうのが有利である。本発明化合物
を精製する必要が生じた場合は、再結晶、カラムクロマ
トグラフィー、薄層クロマトグラフィー等の任意の精製
方法によって分離、精製することができる。In each production method (method A to method F), the molar ratio of each reaction substance is not particularly limited, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto. When the compound of the present invention needs to be purified, it can be separated and purified by any purification method such as recrystallization, column chromatography, thin layer chromatography and the like.

【００４２】尚、本発明に包含される化合物の中で不斉
炭素原子を有する化合物の場合には、光学活性な化合物
（＋）体および（−）体が含まれる。更に、立体配置異
性体が存在する場合には、シス体およびトランス体が含
まれる。本発明の包含される化合物としては、具体的に
は例えば、第１表および第２表の示す化合物が挙げられ
る。Among the compounds included in the present invention, the compounds having an asymmetric carbon atom include optically active compounds (+) and (−). Further, when the configurational isomers exist, cis isomers and trans isomers are included. Specific examples of the compounds included in the present invention include the compounds shown in Tables 1 and 2.

【００４３】但し、第１表および第２表の化合物は例示
のためのものであって、本発明はこれらのみに限定され
るものではない。第１表及び第２表のＱ１〜Ｑ６１はつ
ぎの式で表される基である。However, the compounds shown in Tables 1 and 2 are merely examples, and the present invention is not limited to these. Q1 to Q61 in Tables 1 and 2 are groups represented by the following formula.

【００４４】[0044]

【化２２】 [Chemical formula 22]

【００４５】[0045]

【化２３】 [Chemical formula 23]

【００４６】[0046]

【化２４】 [Chemical formula 24]

【００４７】[0047]

【化２５】 [Chemical 25]

【００４８】第 １ 表Table 1

【００４９】[0049]

【化２６】 [Chemical formula 26]

【００５０】[0050]

【表１】 ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-Cl 4-F O O CH3 H -CH2- 2-Cl 2-Cl O O CH3 H -CH2- 2-Cl 3-Cl O O CH3 H -CH2- 2-Cl 4-Cl O O CH3 H -CH2- 2-Cl 4-Br O O CH3 H -CH2- 2-Cl 4-I O O CH3 H -CH2- 2-Cl 4-CH3 O O CH3 H -CH2- 2-Cl 4-CH2CH2CH2CH3 O O CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2- 2-Cl 4-CH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-CH2Ｃ≡CH O O CH3 H -CH2- 2-Cl 4-Q51 O O CH3 H -CH2- 2-Cl 4-Q52 O O CH3 H -CH2- 2-Cl 4-Q53 O O CH3 H -CH2- 2-Cl 4-Q54 O O CH3 H -CH2- 2-Cl 4-CHF2 O O CH3 H -CH2- 2-Cl 4-CH2Cl O O CH3 H -CH2- 2-Cl 2-CF3 O O CH3 H -CH2- 2-Cl 3-CF3 O O CH3 H -CH2- 2-Cl 4-CF3 O O CH3 H -CH2- 2-Cl 4-CH=C(Cl)CF3 O O CH3 H -CH2- 2-Cl 4-CH2Ｃ≡CBr O O CH3 H -CH2- 2-Cl 4-(Q54-1-Cl) O O ───────────────────────────────────[Table 1] ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-FOO CH 3 H -CH 2 - 2-Cl 2- Cl OO CH 3 H -CH 2 - 2-Cl 3-Cl OO CH 3 H -CH 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 - 2-Cl 4 -Br OO CH 3 H -CH 2 - 2-Cl 4-IOO CH 3 H -CH 2 - 2-Cl 4-CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CH 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 C≡CH OO CH 3 H -CH 2 - 2-Cl 4-Q51 OO CH 3 H -CH 2 - 2-Cl 4-Q52 OO CH 3 H -CH 2 - 2-Cl 4-Q53 OO CH 3 H -CH 2 - 2- Cl 4-Q54 OO CH 3 H -CH 2 - 2-Cl 4-CHF 2 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 Cl OO CH 3 H -CH 2 - 2-Cl 2-CF 3 OO CH 3 H -CH 2 - 2-Cl 3-CF 3 OO CH 3 H -CH 2 - 2-Cl 4-CF 3 OO CH 3 H -CH 2 - 2-Cl 4-CH = C (Cl) CF 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 C≡CBr OO CH 3 H -CH 2 - 2-Cl 4- (Q54-1-Cl) OO ─ ───── ────────────────────────────

【００５１】[0051]

【表２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-Cl 4-CH2CN O O CH3 H -CH2- 2-Cl 4-CH2OH O O CH3 H -CH2- 2-Cl 4-CH2CO2H O O CH3 H -CH2- 2-Cl 4-OCH3 O O CH3 H -CH2- 2-Cl 4-OCH2CH3 O O CH3 H -CH2- 2-Cl 4-OCH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-OCH2C≡CH O O CH3 H -CH2- 2-Cl 4-O(Q53) O O CH3 H -CH2- 2-Cl 4-O(Q54) O O CH3 H -CH2- 2-Cl 4-CH(CH3)2 O O CH3 H -CH2- 2-Cl 4-OCHF2 O O CH3 H -CH2- 2-Cl 4-OCF2Br O O CH3 H -CH2- 2-Cl 2-OCF3 O O CH3 H -CH2- 2-Cl 3-OCF3 O O CH3 H -CH2- 2-Cl 4-OCF3 O O CH3 H -CH2- 2-Cl 4-OCH2CF3 O O CH3 H -CH2- 2-Cl 4-OCF2CHF2 O O CH3 H -CH2- 2-Cl 4-OCF2CHFCl O O CH3 H -CH2- 2-Cl 4-OCF2CHFCF3 O O CH3 H -CH2- 2-Cl 4-OCF2CF2CF3 O O CH3 H -CH2- 2-Cl 4-OCH2CH=CHCl O O CH3 H -CH2- 2-Cl 4-OCH2C≡CBr O O ───────────────────────────────────[Table 2] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-Cl 4-CH 2 CN OO CH 3 H -CH 2 - 2-Cl 4-CH 2 OH OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CO 2 HOO CH 3 H -CH 2 - 2-Cl 4 -OCH 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 C≡CH OO CH 3 H -CH 2 - 2-Cl 4-O (Q53) OO CH 3 H -CH 2 - 2-Cl 4-O (Q54) OO CH 3 H -CH 2 - 2 -Cl 4-CH (CH 3) 2 OO CH 3 H -CH 2 - 2-Cl 4-OCHF 2 OO CH 3 H -CH 2 - 2-Cl 4-OCF 2 Br OO CH 3 H -CH 2 - 2 -Cl 2-OCF 3 OO CH 3 H -CH 2 - 2-Cl 3-OCF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCF 2 CHF 2 OO CH 3 H -CH 2 - 2-Cl 4-OCF 2 CHFCl OO CH 3 H -CH 2 - 2-Cl 4-OCF 2 CHFCF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCF 2 CF 2 CF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH = CHCl OO CH 3 H -CH 2 - 2 -Cl 4-OCH 2 C≡CBr OO ─────────────────────────────── ────

【００５２】[0052]

【表３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-Cl 4-O(Q51-2,2-Cl2) O O CH3 H -CH2- 2-Cl 4-OCH2(Q51-2,2-Cl2) O O CH3 H -CH2- 2-Cl 4-SCH3 O O CH3 H -CH2- 2-Cl 4-SCH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-SCH2C≡CH O O CH3 H -CH2- 2-Cl 4-S(Q54) O O CH3 H -CH2- 2-Cl 4-SCHF2 O O CH3 H -CH2- 2-Cl 4-SCF3 O O CH3 H -CH2- 2-Cl 4-SCF2Cl O O CH3 H -CH2- 2-Cl 4-SOCH3 O O CH3 H -CH2- 2-Cl 4-SOCH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-SO(Q54) O O CH3 H -CH2- 2-Cl 4-SOCF3 O O CH3 H -CH2- 2-Cl 4-SO2CH3 O O CH3 H -CH2- 2-Cl 4-SO2CH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-SO2CH2C≡CH O O CH3 H -CH2- 2-Cl 4-SO2(Q54) O O CH3 H -CH2- 2-Cl 4-SO2CF3 O O CH3 H -CH2- 2-Cl 4-SO2CF2CHFCl O O CH3 H -CH2- 2-Cl 4-CH2OCH3 O O CH3 H -CH2- 2-Cl 4-OCH2CH2OCH3 O O CH3 H -CH2- 2-Cl 4-CH2OCH2CF3 O O ───────────────────────────────────[Table 3] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-Cl 4-O (Q51-2,2-Cl 2 ) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q51-2,2-Cl 2) OO CH 3 H -CH 2 - 2-Cl 4 -SCH 3 OO CH 3 H -CH 2 - 2-Cl 4-SCH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4-SCH 2 C≡CH OO CH 3 H -CH 2 - 2- Cl 4-S (Q54) OO CH 3 H -CH 2 - 2-Cl 4-SCHF 2 OO CH 3 H -CH 2 - 2-Cl 4-SCF 3 OO CH 3 H -CH 2 - 2-Cl 4- SCF 2 Cl OO CH 3 H -CH 2 - 2-Cl 4-SOCH 3 OO CH 3 H -CH 2 - 2-Cl 4-SOCH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4- SO (Q54) OO CH 3 H -CH 2 - 2-Cl 4-SOCF 3 OO CH 3 H -CH 2 - 2-Cl 4-SO 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-SO 2 CH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4-SO 2 CH 2 C≡CH OO CH 3 H -CH 2 - 2-Cl 4-SO 2 (Q54) OO CH 3 H - CH 2 - 2-Cl 4- SO 2 CF 3 OO CH 3 H -CH 2 - 2-Cl 4-SO 2 CF 2 CHFCl OO CH 3 H -CH 2 - 2-Cl 4-CH 2 OCH 3 OO C H 3 H -CH 2 - 2- Cl 4-OCH 2 CH 2 OCH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 OCH 2 CF 3 OO ──────────── ───────────────────────

【００５３】[0053]

【表４】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-OCF2CHFOCF3 O O CH3 H -CH2- 2-Cl 4-CH2SCH3 O O CH3 H -CH2- 2-Cl 4-OCH2CH2SCH3 O O CH3 H -CH2- 2-Cl 4-CH2CO2CH3 O O CH3 H -CH2- 2-Cl 4-CH2CO2CH2CF3 O O CH3 H -CH2- 2-Cl 4-CH2COCH3 O O CH3 H -CH2- 2-Cl 4-OCO2CH3 O O CH3 H -CH2- 2-Cl 4-OCOCH3 O O CH3 H -CH2- 2-Cl 4-COCH3 O O CH3 H -CH2- 2-Cl 4-COCH2CH=CH2 O O CH3 H -CH2- 2-Cl 4-CO(Q53) O O CH3 H -CH2- 2-Cl 4-COCF3 O O CH3 H -CH2- 2-Cl 4-CO2CH2CH3 O O CH3 H -CH2- 2-Cl 4-CO2C(CH3)3 O O CH3 H -CH2- 2-Cl 4-CO2CH2CF3 O O CH3 H -CH2- 2-Cl 4-OCH2CO2CH3 O O CH3 H -CH2- 2-Cl 4-NO2 O O CH3 H -CH2- 2-Cl 4-CN O O CH3 H -CH2- 2-Cl 4-OH O O CH3 H -CH2- 2-Cl 4-CO2H O O CH3 H -CH2- 2-Cl 4-SCN O O CH3 H -CH2- 2-Cl 4-NCS O O ───────────────────────────────────[Table 4] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-OCF 2 CHFOCF 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 SCH 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH 2 SCH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CO 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CO 2 CH 2 CF 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 COCH 3 OO CH 3 H -CH 2 - 2-Cl 4-OCO 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-OCOCH 3 OO CH 3 H -CH 2 - 2-Cl 4-COCH 3 OO CH 3 H -CH 2 - 2-Cl 4-COCH 2 CH = CH 2 OO CH 3 H -CH 2 - 2-Cl 4-CO (Q53) OO CH 3 H -CH 2 - 2-Cl 4-COCF 3 OO CH 3 H -CH 2 - 2- Cl 4-CO 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl 4-CO 2 CH 2 CF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CO 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-NO 2 OO CH 3 H -CH 2 - 2-Cl 4-CN OO CH 3 H -CH 2 - 2-Cl 4-OH OO CH 3 H -CH 2 - 2-Cl 4-CO 2 HOO C H 3 H -CH 2 - 2- Cl 4-SCN OO CH 3 H -CH 2 - 2-Cl 4-NCS OO ────────────────────── ─────────────

【００５４】[0054]

【表５】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-CH2SCN O O CH3 H -CH2- 2-Cl 4-OSO2CH3 O O CH3 H -CH2- 2-Cl 4-CSCH3 O O CH3 H -CH2- 2-Cl 4-NH2 O O CH3 H -CH2- 2-Cl 4-N(CH3)2 O O CH3 H -CH2- 2-Cl 4-N(CH3)CH2CH2CH3 O O CH3 H -CH2- 2-Cl 4-N(CH3)CH2CH=CHCl O O CH3 H -CH2- 2-Cl 4-N(CH3)CH2C6H5 O O CH3 H -CH2- 2-Cl 4-CON(CH3)2 O O CH3 H -CH2- 2-Cl 4-OCON(CH3)2 O O CH3 H -CH2- 2-Cl 4-NHCOCH3 O O CH3 H -CH2- 2-Cl 4-NHCO2CH2CH3 O O CH3 H -CH2- 2-Cl 4-SO2N(CH3)2 O O CH3 H -CH2- 2-Cl 4-NHCSCH3 O O CH3 H -CH2- 2-Cl 4-Si(CH3)3 O O CH3 H -CH2- 2-Cl 3-OCH2O-4 O O CH3 H -CH2- 2-Cl 3-OCF2O-4 O O CH3 H -CH2- 2-Cl 3-OCH2CH2O-4 O O CH3 H -CH2- 2-Cl 3-OCF2CF2O-4 O O CH3 H -CH2- 2-Cl 4-C6H5 O O CH3 H -CH2- 2-Cl 4-(C6H4-4-Cl) O O CH3 H -CH2- 2-Cl 4-OC6H5 O O ───────────────────────────────────[Table 5] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-CH 2 SCN OO CH 3 H -CH 2 - 2-Cl 4-OSO 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CSCH 3 OO CH 3 H -CH 2 - 2-Cl 4-NH 2 OO CH 3 H -CH 2 - 2-Cl 4-N (CH 3) 2 OO CH 3 H -CH 2 - 2-Cl 4-N (CH 3) CH 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4 -N (CH 3) CH 2 CH = CHCl OO CH 3 H -CH 2 - 2-Cl 4-N (CH 3) CH 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CON (CH 3) 2 OO CH 3 H -CH 2 - 2-Cl 4-OCON (CH 3) 2 OO CH 3 H -CH 2 - 2-Cl 4-NHCOCH 3 OO CH 3 H -CH 2 - 2-Cl 4 -NHCO 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-SO 2 N (CH 3) 2 OO CH 3 H -CH 2 - 2-Cl 4- NHCSCH 3 OO CH 3 H -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl 3-OCH 2 O-4 OO CH 3 H -CH 2 - 2-Cl 3-OCF 2 O-4 OO CH 3 H -CH 2 - 2-Cl 3-OCH 2 CH 2 O-4 OO CH 3 H -CH 2 - 2-Cl 3-OCF 2 CF 2 O-4 OO CH 3 H -CH 2 - 2-Cl 4-C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4- (C 6 H 4 -4-Cl) OO CH 3 H -CH 2 - 2-Cl 4 -OC 6 H 5 OO ────────────────────────────────────

【００５５】[0055]

【表６】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-O(C6H4-4-Cl) O O CH3 H -CH2- 2-Cl 4-O(C6H4-4-CF3) O O CH3 H -CH2- 2-Cl 4-O(C6H3-2,4-Cl2) O O CH3 H -CH2- 2-Cl 4-O(C6H3-2-Cl-4-CF3) O O CH3 H -CH2- 2-Cl 3-O(C6H3-2-Cl-4-CF3) O O CH3 H -CH2- 2-Cl 4-S(C6H3-2-Cl-4-CF3) O O CH3 H -CH2- 2-Cl 4-NH(C6H3-2-Cl-4-CF3) O O CH3 H -CH2- 2-Cl 4-OCH2CH2CH3 O O CH3 H -CH2- 2-Cl 4-CH2C6H5 O O CH3 H -CH2- 2-Cl 4-CF2(C6H4-4-Br) O O CH3 H -CH2- 2-Cl 4-COC6H5 O O CH3 H -CH2- 2-Cl 4-OCH2(C6H4-4-CF3) O O CH3 H -CH2- 2-Cl 4-CH2OC6H5 O O CH3 H -CH2- 2-Cl 4-NHCH2C6H5 O O CH3 H -CH2- 2-Cl 4-CH2CH2C6H5 O O CH3 H -CH2- 2-Cl 4-CH=CH(C6H4-4-Cl) O O CH3 H -CH2- 2-Cl 4-N=NC6H5 O O CH3 H -CH2- 2-Cl 4-OCH2CH2C6H5 O O CH3 H -CH2- 2-Cl 4-CH2OCH2CH2OCH2CH3 O O CH3 H -CH2- 2-Cl 4-NHCSNHC6H5 O O CH3 H -CH2- 2-Cl 4-CH2CH2CH3 O O CH3 H -CH2- 2-Cl 4-CH2CH2OCH2CH3 O O ───────────────────────────────────[Table 6] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-O (C 6 H 4 -4-Cl) OO CH 3 H -CH 2 - 2-Cl 4-O (C 6 H 4 -4-CF 3) OO CH 3 H -CH 2 - 2- Cl 4-O (C 6 H 3 -2,4-Cl 2) OO CH 3 H -CH 2 - 2-Cl 4-O (C 6 H 3 -2-Cl-4-CF 3) OO CH 3 H -CH 2 - 2-Cl 3- O (C 6 H 3 -2-Cl-4-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-S (C 6 H 3 -2-Cl-4 -CF 3) OO CH 3 H -CH 2 - 2-Cl 4-NH (C 6 H 3 -2-Cl-4-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CF 2 (C 6 H 4 -4-Br) OO CH 3 H -CH 2 - 2-Cl 4- COC 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (C 6 H 4 -4-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-CH 2 OC 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-NHCH 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CH 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CH = CH (C 6 H 4 -4-Cl) OO CH 3 H -CH 2 - 2-Cl 4-N = NC 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 OCH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-NHCSNHC 6 H 5 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 4-CH 2 CH 2 OCH 2 CH 3 OO ────────────────────────────────────

【００５６】[0056]

【表７】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-O(Q1-1-CH3) O O CH3 H -CH2- 2-Cl 4-O(Q2-1-CH3) O O CH3 H -CH2- 2-Cl 4-(Q3) O O CH3 H -CH2- 2-Cl 4-CH2(Q4) O O CH3 H -CH2- 2-Cl 4-(Q5) O O CH3 H -CH2- 2-Cl 4-C≡C(Q6) O O CH3 H -CH2- 2-Cl 4-CH2(Q7) O O CH3 H -CH2- 2-Cl 4-(Q8-3,5-(CF3)2) O O CH3 H -CH2- 2-Cl 4-(Q8-3-C6H5) O O CH3 H -CH2- 2-Cl 4-OCH2(Q9-1-CH3) O O CH3 H -CH2- 2-Cl 4-O(Q10-1-CH3) O O CH3 H -CH2- 2-Cl 4-(Q11-1-C6H5) O O CH3 H -CH2- 2-Cl 4-(Q12-1-CH3) O O CH3 H -CH2- 2-Cl 4-OCH2(Q13-1-CH3) O O CH3 H -CH2- 2-Cl 4-O(Q14-1-CH3) O O CH3 H -CH2- 2-Cl 4-(Q15) O O CH3 H -CH2- 2-Cl 4-O(Q16) O O CH3 H -CH2- 2-Cl 4-O(Q17-5-CH3) O O CH3 H -CH2- 2-Cl 4-O(Q18) O O CH3 H -CH2- 2-Cl 4-OCH2(Q19) O O CH3 H -CH2- 2-Cl 4-OCH2(Q20-4-Cl) O O CH3 H -CH2- 2-Cl 4-(Q21) O O ───────────────────────────────────[Table 7] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-O (Q1-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q2-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4- (Q3 ) OO CH 3 H -CH 2 - 2-Cl 4-CH 2 (Q4) OO CH 3 H -CH 2 - 2-Cl 4- (Q5) OO CH 3 H -CH 2 - 2-Cl 4-C≡ C (Q6) OO CH 3 H -CH 2 - 2-Cl 4-CH 2 (Q7) OO CH 3 H -CH 2 - 2-Cl 4- (Q8-3,5- (CF 3) 2) OO CH 3 H -CH 2 - 2-Cl 4- (Q8-3-C 6 H 5) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q9-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q10-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4- (Q11-1-C 6 H 5) OO CH 3 H -CH 2 - 2-Cl 4- (Q12-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q13-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q14- 1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4- (Q15) OO CH 3 H -CH 2 - 2-Cl 4-O (Q16) OO CH 3 H -CH 2 - 2-Cl 4 -O (Q17-5-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q18) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q19) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q20-4-Cl) OO CH 3 H -CH 2 - 2-Cl 4- (Q21) OO ───────────────────────────────────

【００５７】[0057]

【表８】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-OCH2(Q22) O O CH3 H -CH2- 2-Cl 4-(Q23) O O CH3 H -CH2- 2-Cl 4-OCH2(Q24) O O CH3 H -CH2- 2-Cl 4-O(Q25-3-CH3) O O CH3 H -CH2- 2-Cl 4-(Q26-1-CH3) O O CH3 H -CH2- 2-Cl 4-OCH2(Q27-1-CH3) O O CH3 H -CH2- 2-Cl 4-OCH2(Q28-1-CH3) O O CH3 H -CH2- 2-Cl 4-O(Q29-1-CH3) O O CH3 H -CH2- 2-Cl 4-NHCONH(Q30) O O CH3 H -CH2- 2-Cl 4-O(Q31) O O CH3 H -CH2- 2-Cl 4-OCH2(Q32) O O CH3 H -CH2- 2-Cl 4-OCH2(Q33) O O CH3 H -CH2- 2-Cl 4-O(Q34) O O CH3 H -CH2- 2-Cl 4-O(Q36) O O CH3 H -CH2- 2-Cl 4-OCH2(Q37-5-Cl) O O CH3 H -CH2- 2-Cl 3-O(Q38-3-Cl-5-CF3) O O CH3 H -CH2- 2-Cl 4-O(Q38-3,5-Cl2) O O CH3 H -CH2- 2-Cl 4-O(Q38-3-Cl-5-CF3) O O CH3 H -CH2- 2-Cl 4-NH(Q38-5-CF3) O O CH3 H -CH2- 2-Cl 4-(Q38-3-Cl-5-CF3) O O CH3 H -CH2- 2-Cl 4-O(Q39-5-Br) O O CH3 H -CH2- 2-Cl 4-O(Q40-2,6-Cl2) O O ───────────────────────────────────[Table 8] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-OCH 2 (Q22) OO CH 3 H -CH 2 - 2-Cl 4- (Q23) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q24) OO CH 3 H -CH 2 - 2-Cl 4-O ( Q25-3-CH 3) OO CH 3 H -CH 2 - 2-Cl 4- (Q26-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q27-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q28-1-CH 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q29-1 -CH 3) OO CH 3 H -CH 2 - 2-Cl 4-NHCONH (Q30) OO CH 3 H -CH 2 - 2-Cl 4-O (Q31) OO CH 3 H -CH 2 - 2-Cl 4 -OCH 2 (Q32) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q33) OO CH 3 H -CH 2 - 2-Cl 4-O (Q34) OO CH 3 H -CH 2 - 2 -Cl 4-O (Q36) OO CH 3 H -CH 2 - 2-Cl 4-OCH 2 (Q37-5-Cl) OO CH 3 H -CH 2 - 2-Cl 3-O (Q38-3-Cl -5-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q38-3,5-Cl 2) OO CH 3 H -CH 2 - 2-Cl 4-O (Q38-3-Cl -5-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-NH (Q38-5- CF 3) OO CH 3 H -CH 2 - 2-Cl 4- (Q38-3-Cl-5-CF 3) OO CH 3 H -CH 2 - 2-Cl 4-O (Q39-5-Br) OO CH 3 H -CH 2 - 2- Cl 4-O (Q40-2,6-Cl 2) OO ────────────────────────── ─────────

【００５８】[0058]

【表９】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 4-O(Q41-6-Cl) O O CH3 H -CH2- 2-Cl 4-O(Q42) O O CH3 H -CH2- 2-Cl 4-O(Q43-5-Cl) O O CH3 H -CH2- 2-Cl 4-O(Q44) O O CH3 H -CH2- 2-Cl 4-O(Q45-4-CF3-6-Cl) O O CH3 H -CH2- 2-Cl 4-O(Q46) O O CH3 H -CH2- 2-Cl 4-O(Q47) O O CH3 H -CH2- 2-Cl 4-O(Q47-4-Cl) O O CH3 H -CH2- 2-Cl 4-O(Q48) O O CH3 H -CH2- 2-Cl 4-O(Q49) O O CH3 H -CH2- 2-Cl 3-O(Q50-6-Cl) O O CH3 H -CH2- 2-Cl 3-O(Q50-6-CF3) O O CH3 H -CH2- 2-Cl 2,4-F2 O O CH3 H -CH2- 2-Cl 2,3-Cl2 O O CH3 H -CH2- 2-Cl 2,4-Cl2 O O CH3 H -CH2- 2-Cl 2,5-Cl2 O O CH3 H -CH2- 2-Cl 2,6-Cl2 O O CH3 H -CH2- 2-Cl 3,4-Cl2 O O CH3 H -CH2- 2-Cl 3,5-Cl2 O O CH3 H -CH2- 2-Cl 3,4-Br2 O O CH3 H -CH2- 2-Cl 3,4-I2 O O CH3 H -CH2- 2-Cl 2,4-(CH3)2 O O ───────────────────────────────────[Table 9] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 4-O (Q41-6-Cl ) OO CH 3 H -CH 2 - 2-Cl 4-O (Q42) OO CH 3 H -CH 2 - 2-Cl 4-O (Q43-5-Cl) OO CH 3 H -CH 2 - 2 -Cl 4-O (Q44) OO CH 3 H -CH 2 - 2-Cl 4-O (Q45-4-CF 3 -6-Cl) OO CH 3 H -CH 2 - 2-Cl 4-O ( Q46) OO CH 3 H -CH 2 - 2-Cl 4-O (Q47) OO CH 3 H -CH 2 - 2-Cl 4-O (Q47-4-Cl) OO CH 3 H -CH 2 - 2-Cl 4-O (Q48) OO CH 3 H -CH 2 - 2-Cl 4-O (Q49) OO CH 3 H -CH 2 - 2-Cl 3-O (Q50-6 -Cl) OO CH 3 H -CH 2 - 2-Cl 3-O (Q50-6-CF 3) OO CH 3 H -CH 2 - 2-Cl 2,4-F 2 OO CH 3 H -CH 2 - 2-Cl 2,3-Cl 2 OO CH 3 H -CH 2 - 2-Cl 2,4-Cl 2 OO CH 3 H -CH 2 - 2-Cl 2,5-Cl 2 OO CH 3 H -CH 2 - 2-Cl 2,6-Cl 2 OO CH 3 H -CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 - 2-Cl 3,5-Cl 2 OO CH 3 H -CH 2 - 2-Cl 3,4-Br 2 OO CH 3 H -CH 2 - 2-Cl 3,4-I 2 OO CH 3 H -CH 2 - 2-Cl 2,4- (CH 3 ) 2 OO ────────────────────────────────────

【００５９】[0059]

【表１０】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 3,4-(OCH3)2 O O CH3 H -CH2- 2-Cl 2-F-4-Cl O O CH3 H -CH2- 2-Cl 2-F-4-Br O O CH3 H -CH2- 2-Cl 2-F-4-OCF3 O O CH3 H -CH2- 2-Cl 2-F-4-OCF2CHF2 O O CH3 H -CH2- 2-Cl 3-F-4-Cl O O CH3 H -CH2- 2-Cl 2-Cl-4-CF3 O O CH3 H -CH2- 2-Cl 2-Cl-5-O(Q50-6-Cl) O O CH3 H -CH2- 2-Cl 3-Cl-4-Br O O CH3 H -CH2- 2-Cl 3-Cl-4-CF3 O O CH3 H -CH2- 2-Cl 3-Cl-4-OCF3 O O CH3 H -CH2- 2-Cl 3-Cl-4-OCF2CHF2 O O CH3 H -CH2- 2-Cl 3-Cl-4-O(C6H4-4-CF3) O O CH3 H -CH2- 2-Cl 3-CF3-4-Cl O O CH3 H -CH2- 2-Cl 3-CH3-4-Br O O CH3 H -CH2- 2-Cl 3-OCH3-4-CF3 O O CH3 H -CH2- 2-Cl 3-CF3-4-Br O O CH3 H -CH2- 2-Cl 3-Cl-4-I O O CH3 H -CH2- 2-Cl 3-Cl-4-F O O CH3 H -CH2- 2-Cl 3-Cl-4-CH3 O O CH3 H -CH2- 2-Cl 2,3,4-F3 O O CH3 H -CH2- 2-Cl 2,4,5-F3 O O ───────────────────────────────────[Table 10] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 3,4- (OCH 3) 2 OO CH 3 H -CH 2 - 2-Cl 2-F-4-Cl OO CH 3 H -CH 2 - 2-Cl 2-F-4-Br OO CH 3 H -CH 2 - 2-Cl 2 -F-4-OCF 3 OO CH 3 H -CH 2 - 2-Cl 2-F-4-OCF 2 CHF 2 OO CH 3 H -CH 2 - 2-Cl 3- F-4-Cl OO CH 3 H -CH 2 - 2-Cl 2-Cl-4-CF 3 OO CH 3 H -CH 2 - 2-Cl 2-Cl-5-O (Q50-6-Cl) OO CH 3 H -CH 2 - 2- Cl 3-Cl-4-Br OO CH 3 H -CH 2 - 2-Cl 3-Cl-4-CF 3 OO CH 3 H -CH 2 - 2-Cl 3-Cl -4-OCF 3 OO CH 3 H -CH 2 - 2-Cl 3-Cl-4-OCF 2 CHF 2 OO CH 3 H -CH 2 - 2-Cl 3-Cl-4-O (C 6 H 4 - 4-CF 3) OO CH 3 H -CH 2 - 2-Cl 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 2-Cl 3-CH 3 -4-Br OO CH 3 H -CH 2 - 2-Cl 3-OCH 3 -4-CF 3 OO CH 3 H -CH 2 - 2-Cl 3-CF 3 -4-Br OO CH 3 H -CH 2 - 2-Cl 3-Cl-4-IOO CH 3 H -CH 2 - 2- Cl 3-Cl-4-FOO CH 3 H -CH 2 - 2-Cl 3-Cl-4-CH 3 OO CH 3 H -CH 2 - 2 -Cl 2,3,4-F 3 OO CH 3 H -CH 2 - 2-Cl 2,4,5-F 3 OO ─────────── ────────────────────────

【００６０】[0060]

【表１１】 第 １ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl 2,5-F2-4-Cl O O CH3 H -CH2- 2-Cl 3,5-F2-4-CF3 O O CH3 H -CH2- 2-Cl 2,5-Cl2-4-OCF2CHF2 O O CH3 H -CH2- 2-Cl 2,6-Cl2-4-CF3 O O CH3 H -CH2- 2-Cl 2,4,5-Cl3 O O CH3 H -CH2- 2-Cl 3,4,5-Cl3 O O CH3 H -CH2- 2-Cl 4-OSO2C6H5 O O CH3 H -CH2- 2-Cl 3,5-Cl2-4-OCF2CHF2 O O CH3 H -CH2- 2-Cl 2-F-4,5-Cl2 O O CH3 H -CH2- 2-Cl 4-CF2CF3 O O CH3 H -CH2- 2-Cl 2,3,4,5-F4 O O CH3 H -CH2- 2-Cl 2,4-F2-3,5-Cl2 O O CH3 H -CH2- 2-Cl 2,6-F2-3,5-Cl2 O O CH3 H -CH2- 2-Cl 2,3,4,5,6-F5 O O CH3 H -CH2- 2-Cl 4-OCH2CH2CH2CH3 O O CH3 H -CH2- 2-Cl 3-F-4-CH3 O O CH3 H -CH2- 2-Cl 2-Br-4-OCF3 O O CH3 H -CH2- 2-Cl 4-(CH2)5CH3 O O CH3 H -CH2- 2-Cl 2-CH3-4-OCF3 O O CH3 H -CH2- 2-Cl 4-OCOC6H5 O O CH3 H -CH(CH3)- 2-Cl 3-F O O CH3 H -CH(CH3)- 2-Cl 4-F O O ──────────────────────────────────[Table 11] Table 1 (continued) ─────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2 -Cl 2,5-F 2 -4-Cl OO CH 3 H -CH 2 - 2-Cl 3,5-F 2 -4-CF 3 OO CH 3 H -CH 2 - 2-Cl 2,5-Cl 2 -4-OCF 2 CHF 2 OO CH 3 H -CH 2 - 2-Cl 2,6-Cl 2 -4-CF 3 OO CH 3 H -CH 2 - 2-Cl 2,4,5-Cl 3 OO CH 3 H -CH 2 - 2- Cl 3,4,5-Cl 3 OO CH 3 H -CH 2 - 2-Cl 4-OSO 2 C 6 H 5 OO CH 3 H -CH 2 - 2-Cl 3, 5-Cl 2 -4-OCF 2 CHF 2 OO CH 3 H -CH 2 - 2-Cl 2-F-4,5-Cl 2 OO CH 3 H -CH 2 - 2-Cl 4-CF 2 CF 3 OO CH 3 H -CH 2 - 2- Cl 2,3,4,5-F 4 OO CH 3 H -CH 2 - 2-Cl 2,4-F 2 -3,5-Cl 2 OO CH 3 H -CH 2 - 2-Cl 2,6-F 2 -3,5-Cl 2 OO CH 3 H -CH 2 - 2-Cl 2,3,4,5,6-F 5 OO CH 3 H -CH 2 - 2 -Cl 4-OCH 2 CH 2 CH 2 CH 3 OO CH 3 H -CH 2 - 2-Cl 3-F-4-CH 3 OO CH 3 H -CH 2 - 2-Cl 2-Br-4-OCF 3 OO CH 3 H -CH 2 - 2 -Cl 4- (CH 2) 5 CH 3 OO CH 3 H -CH 2 - 2-Cl 2-CH 3 -4-OCF 3 OO CH 3 H -CH 2 - 2-Cl 4-OCOC 6 H 5 OO CH 3 H -CH (CH 3) - 2-Cl 3-FOO CH 3 H -CH (CH 3) - 2-Cl 4-FOO ──────────────────────────────────

【００６１】[0061]

【表１２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)- 2-Cl 3-Cl O O CH3 H -CH(CH3)- 2-Cl 4-Cl O O CH3 H -CH(CH3)- 2-Cl 4-Br O O CH3 H -CH(CH3)- 2-Cl 4-I O O CH3 H -CH(CH3)- 2-Cl 4-CH2CH2CH2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)- 2-Cl 4-Q53 O O CH3 H -CH(CH3)- 2-Cl 4-Q54 O O CH3 H -CH(CH3)- 2-Cl 4-CF3 O O CH3 H -CH(CH3)- 2-Cl 4-OCH2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-O(Q54) O O CH3 H -CH(CH3)- 2-Cl 4-CH(CH3)2 O O CH3 H -CH(CH3)- 2-Cl 4-OCHF2 O O CH3 H -CH(CH3)- 2-Cl 4-OCF2Br O O CH3 H -CH(CH3)- 2-Cl 4-OCF3 O O CH3 H -CH(CH3)- 2-Cl 4-OCF2CHF2 O O CH3 H -CH(CH3)- 2-Cl 4-SCH3 O O CH3 H -CH(CH3)- 2-Cl 4-SCF3 O O CH3 H -CH(CH3)- 2-Cl 4-SO2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-CH2OCH3 O O CH3 H -CH(CH3)- 2-Cl 4-OCH2CH2OCH3 O O CH3 H -CH(CH3)- 2-Cl 4-COCH3 O O ──────────────────────────────────[Table 12] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 )- 2-Cl 3-Cl OO CH 3 H -CH (CH 3 )-2-Cl 4-Cl OO CH 3 H -CH (CH 3 )-2-Cl 4-Br OO CH 3 H -CH (CH 3 ) -2-Cl 4-IOO CH 3 H -CH (CH 3 )-2-Cl 4-CH 2 CH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-Q53 OO CH 3 H -CH (CH 3 )-2-Cl 4-Q54 OO CH 3 H -CH (CH 3 )-2-Cl 4-CF 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-OCH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-O (Q54) OO CH 3 H -CH (CH 3 )-2-Cl 4-CH (CH 3 ) 2 OO CH 3 H -CH (CH 3 )-2-Cl 4-OCHF 2 OO CH 3 H -CH (CH 3 )-2-Cl 4- OCF 2 Br OO CH 3 H -CH (CH 3 )-2-Cl 4-OCF 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-OCF 2 CHF 2 OO CH 3 H -CH (CH 3 )-2-Cl 4-SCH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-SCF 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-SO 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CH 2 OCH 3 O O CH 3 H -CH (CH 3 )-2-Cl 4-OCH 2 CH 2 OCH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-COCH 3 OO ────────── ─────────────────────────

【００６２】[0062]

【表１３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)- 2-Cl 4-CO2C(CH3)3 O O CH3 H -CH(CH3)- 2-Cl 4-CO2CH2CF3 O O CH3 H -CH(CH3)- 2-Cl 4-NO2 O O CH3 H -CH(CH3)- 2-Cl 4-CN O O CH3 H -CH(CH3)- 2-Cl 4-N(CH3)2 O O CH3 H -CH(CH3)- 2-Cl 4-Si(CH3)3 O O CH3 H -CH(CH3)- 2-Cl 3-OCH2O-4 O O CH3 H -CH(CH3)- 2-Cl 3-OCF2O-4 O O CH3 H -CH(CH3)- 2-Cl 4-C6H5 O O CH3 H -CH(CH3)- 2-Cl 4-(C6H4-4-Cl) O O CH3 H -CH(CH3)- 2-Cl 4-OC6H5 O O CH3 H -CH(CH3)- 2-Cl 4-O(C6H4-4-CF3) O O CH3 H -CH(CH3)- 2-Cl 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-CH2C6H5 O O CH3 H -CH(CH3)- 2-Cl 4-CH=CH(C6H4-4-Cl) O O CH3 H -CH(CH3)- 2-Cl 4-N=NC6H5 O O CH3 H -CH(CH3)- 2-Cl 4-CH2OCH2CH2OCH2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-CH2CH2CH3 O O CH3 H -CH(CH3)- 2-Cl 4-CH2CH2OCH2CH3 O O CH3 H -CH(CH3)- 2-Cl 2,4-Cl2 O O CH3 H -CH(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CH(CH3)- 2-Cl 3,5-Cl2 O O ──────────────────────────────────[Table 13] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 )- 2-Cl 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CO 2 CH 2 CF 3 OO CH 3 H -CH (CH 3 )-2-Cl 4 -NO 2 OO CH 3 H -CH (CH 3 )-2-Cl 4-CN OO CH 3 H -CH (CH 3 )-2-Cl 4-N (CH 3 ) 2 OO CH 3 H -CH (CH 3 )-2-Cl 4-Si (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2-Cl 3-OCH 2 O-4 OO CH 3 H -CH (CH 3 )-2-Cl 3 -OCF 2 O-4 OO CH 3 H -CH (CH 3 )-2-Cl 4-C 6 H 5 OO CH 3 H -CH (CH 3 )-2-Cl 4- (C 6 H 4 -4- Cl) OO CH 3 H -CH (CH 3 )-2-Cl 4-OC 6 H 5 OO CH 3 H -CH (CH 3 )-2-Cl 4-O (C 6 H 4 -4-CF 3 ) OO CH 3 H -CH (CH 3 )-2-Cl 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CH 2 C 6 H 5 OO CH 3 H -CH (CH 3 )-2-Cl 4-CH = CH (C 6 H 4 -4-Cl) OO CH 3 H -CH (CH 3 )-2-Cl 4-N = NC 6 H 5 OO CH 3 H- CH (CH 3 )-2-Cl 4-CH 2 OCH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH (CH 3 )-2 -Cl 2,4-Cl 2 OO CH 3 H -CH (CH 3 )-2-Cl 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-2-Cl 3,5-Cl 2 OO ─ ──────────────────────────────────

【００６３】[0063]

【表１４】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)- 2-Cl 3,4-Br2 O O CH3 H -CH(CH3)- 2-Cl 2-F-4-Cl O O CH3 H -CH(CH3)- 2-Cl 3-F-4-Cl O O CH3 H -CH(CH3)- 2-Cl 3-Cl-4-Br O O CH3 H -CH(CH3)- 2-Cl 3-Cl-4-CF3 O O CH3 H -CH(CH3)- 2-Cl 3-CF3-4-Cl O O CH3 H -CH(CH3)- 2-Cl 3-Cl-4-I O O CH3 H -CH(CH3)- 2-Cl 3-Cl-4-F O O CH3 H -CH(CH3)- 2-Cl 3-Cl-4-CH3 O O CH3 H -CH(CH3)- 2-Cl 2,5-F2-4-Cl O O CH3 H -CH(CH3)- 2-Cl 3,5-F2-4-CF3 O O CH3 H -CH(CH3)- 2-Cl 2,4,5-Cl3 O O CH3 H -CH(CH3)- 2-Cl 3,4,5-Cl3 O O CH3 H -CH(CH3)- 2-Cl 4-CF2CF3 O O CH3 H -CH(CH3)- 2-Cl 2,4-F2-3,5-Cl2 O O CH3 H -CH(CH3)- 2-Cl 2,3,4,5,6-F5 O O CH3 H -CH(CH3)- 2-Cl 4-OCH2CH2CH2CH3 O O CH3 H -CH(CH3)- 2-Cl 3-F-4-CH3 O O CH3 H -CH(CH3)- 2-Cl 4-(CH2)5CH3 O O CH3 H -CH(CH3)- 2-Cl 4-OCOC6H5 O O CH3 H -C(CH3)2- 2-Cl 4-CH(CH3)CH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-F O O ──────────────────────────────────[Table 14] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 )- 2-Cl 3,4-Br 2 OO CH 3 H -CH (CH 3 )-2-Cl 2-F-4-Cl OO CH 3 H -CH (CH 3 )-2-Cl 3-F-4- Cl OO CH 3 H -CH (CH 3 )-2-Cl 3-Cl-4-Br OO CH 3 H -CH (CH 3 )-2-Cl 3-Cl-4-CF 3 OO CH 3 H -CH (CH 3 )-2-Cl 3-CF 3 -4-Cl OO CH 3 H -CH (CH 3 )-2-Cl 3-Cl-4-IOO CH 3 H -CH (CH 3 )-2-Cl 3-Cl-4-FOO CH 3 H -CH (CH 3 )-2-Cl 3-Cl-4-CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 2,5-F 2 -4 -Cl OO CH 3 H -CH (CH 3 )-2-Cl 3,5-F 2 -4-CF 3 OO CH 3 H -CH (CH 3 )-2-Cl 2,4,5-Cl 3 OO CH 3 H -CH (CH 3 )-2-Cl 3,4,5-Cl 3 OO CH 3 H -CH (CH 3 )-2-Cl 4-CF 2 CF 3 OO CH 3 H -CH (CH 3 )-2-Cl 2,4-F 2 -3,5-Cl 2 OO CH 3 H -CH (CH 3 )-2-Cl 2,3,4,5,6-F 5 OO CH 3 H -CH (CH 3 )-2-Cl 4-OCH 2 CH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-Cl 3-F-4-CH 3 OO CH 3 H -CH (CH 3 ) -2-Cl 4- (CH 2) 5 CH 3 OO CH 3 H -CH (CH 3) - 2-Cl 4-OCOC 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH (CH 3 ) CH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-FOO ─────────────────────────── ───────

【００６４】[0064]

【表１５】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2- 2-Cl 3-Cl O O CH3 H -C(CH3)2- 2-Cl 4-Cl O O CH3 H -C(CH3)2- 2-Cl 4-Br O O CH3 H -C(CH3)2- 2-Cl 4-I O O CH3 H -C(CH3)2- 2-Cl 4-CH2CH2CH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-C(CH3)3 O O CH3 H -C(CH3)2- 2-Cl 4-Q53 O O CH3 H -C(CH3)2- 2-Cl 4-Q54 O O CH3 H -C(CH3)2- 2-Cl 4-CF3 O O CH3 H -C(CH3)2- 2-Cl 4-OCH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-O(Q54) O O CH3 H -C(CH3)2- 2-Cl 4-CH(CH3)2 O O CH3 H -C(CH3)2- 2-Cl 4-OCHF2 O O CH3 H -C(CH3)2- 2-Cl 4-OCF2Br O O CH3 H -C(CH3)2- 2-Cl 4-OCF3 O O CH3 H -C(CH3)2- 2-Cl 4-OCF2CHF2 O O CH3 H -C(CH3)2- 2-Cl 4-SCH3 O O CH3 H -C(CH3)2- 2-Cl 4-SCF3 O O CH3 H -C(CH3)2- 2-Cl 4-SO2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-CH2OCH3 O O CH3 H -C(CH3)2- 2-Cl 4-OCH2CH2OCH3 O O CH3 H -C(CH3)2- 2-Cl 4-COCH3 O O ──────────────────────────────────[Table 15] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 - 2-Cl 3-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 4-Br OO CH 3 H -C ( CH 3) 2 - 2-Cl 4-IOO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH 2 CH 2 CH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-Q53 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-Q54 OO CH 3 H -C (CH 3) 2 - 2- Cl 4-CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4 -O (Q54) OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH (CH 3) 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCHF 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCF 2 Br OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCF 3 OO CH 3 H -C (CH 3) 2 - 2- Cl 4-OCF 2 CHF 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-SCH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-SCF 3 OO CH 3 H - C (CH 3) 2 - 2 -Cl 4-SO 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH 2 OCH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCH 2 CH 2 OCH 3 OO CH 3 H -C ( CH 3) 2 - 2-Cl 4-COCH 3 OO ──────────────────────────────────

【００６５】[0065]

【表１６】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2- 2-Cl 4-CO2C(CH3)3 O O CH3 H -C(CH3)2- 2-Cl 4-CO2CH2CF3 O O CH3 H -C(CH3)2- 2-Cl 4-NO2 O O CH3 H -C(CH3)2- 2-Cl 4-CN O O CH3 H -C(CH3)2- 2-Cl 4-N(CH3)2 O O CH3 H -C(CH3)2- 2-Cl 4-Si(CH3)3 O O CH3 H -C(CH3)2- 2-Cl 3-OCH2O-4 O O CH3 H -C(CH3)2- 2-Cl 3-OCF2O-4 O O CH3 H -C(CH3)2- 2-Cl 4-C6H5 O O CH3 H -C(CH3)2- 2-Cl 4-(C6H4-4-Cl) O O CH3 H -C(CH3)2- 2-Cl 4-OC6H5 O O CH3 H -C(CH3)2- 2-Cl 4-O(C6H4-4-CF3) O O CH3 H -C(CH3)2- 2-Cl 4-OCH2CH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-CH2C6H5 O O CH3 H -C(CH3)2- 2-Cl 4-CH=CH(C6H4-4-Cl) O O CH3 H -C(CH3)2- 2-Cl 4-N=NC6H5 O O CH3 H -C(CH3)2- 2-Cl 4-CH2OCH2CH2OCH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-CH2CH2CH3 O O CH3 H -C(CH3)2- 2-Cl 4-CH2CH2OCH2CH3 O O CH3 H -C(CH3)2- 2-Cl 2,4-Cl2 O O CH3 H -C(CH3)2- 2-Cl 3,4-Cl2 O O CH3 H -C(CH3)2- 2-Cl 3,5-Cl2 O O ──────────────────────────────────[Table 16] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CO 2 CH 2 CF 3 OO CH 3 H -C (CH 3) 2 - 2 -Cl 4-NO 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CN OO CH 3 H -C (CH 3) 2 - 2-Cl 4-N (CH 3) 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-Si (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 3-OCH 2 O-4 OO CH 3 H -C (CH 3) 2 - 2-Cl 3 -OCF 2 O-4 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-C 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4- (C 6 H 4 -4- Cl) OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OC 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4- O (C 6 H 4 -4-CF 3 ) OO CH 3 H -C (CH 3 ) 2 -2-Cl 4-OCH 2 CH 2 CH 3 OO CH 3 H -C (CH 3 ) 2 -2-Cl 4-CH 2 C 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH = CH (C 6 H 4 -4-Cl) OO CH 3 H -C (CH 3) 2 - 2-Cl 4-N = NC 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH 2 OCH 2 CH 2 OCH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH 2 CH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 2,4-Cl 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 3,5-Cl 2 OO ─────────────────────────────── ───

【００６６】[0066]

【表１７】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2- 2-Cl 3,4-Br2 O O CH3 H -C(CH3)2- 2-Cl 2-F-4-Cl O O CH3 H -C(CH3)2- 2-Cl 3-F-4-Cl O O CH3 H -C(CH3)2- 2-Cl 3-Cl-4-Br O O CH3 H -C(CH3)2- 2-Cl 3-Cl-4-CF3 O O CH3 H -C(CH3)2- 2-Cl 3-CF3-4-Cl O O CH3 H -C(CH3)2- 2-Cl 3-Cl-4-I O O CH3 H -C(CH3)2- 2-Cl 3-Cl-4-F O O CH3 H -C(CH3)2- 2-Cl 3-Cl-4-CH3 O O CH3 H -C(CH3)2- 2-Cl 2,5-F2-4-Cl O O CH3 H -C(CH3)2- 2-Cl 3,5-F2-4-CF3 O O CH3 H -C(CH3)2- 2-Cl 2,4,5-Cl3 O O CH3 H -C(CH3)2- 2-Cl 3,4,5-Cl3 O O CH3 H -C(CH3)2- 2-Cl 4-CF2CF3 O O CH3 H -C(CH3)2- 2-Cl 2,4-F2-3,5-Cl2 O O CH3 H -C(CH3)2- 2-Cl 2,3,4,5,6-F5 O O CH3 H -C(CH3)2- 2-Cl 4-OCH2CH2CH2CH3 O O CH3 H -C(CH3)2- 2-Cl 3-F-4-CH3 O O CH3 H -C(CH3)2- 2-Cl 4-(CH2)5CH3 O O CH3 H -C(CH3)2- 2-Cl 4-OCOC6H5 O O CH3 H -CH2- 2-F 4-Cl O O CH3 H -CH2- 2-F 4-Br O O ──────────────────────────────────[Table 17] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 - 2-Cl 3,4-Br 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 2-F-4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 3-F -4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 3-Cl-4-Br OO CH 3 H -C (CH 3) 2 - 2-Cl 3-Cl-4-CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 3-CF 3 -4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 3-Cl-4-IOO CH 3 H -C ( CH 3) 2 - 2-Cl 3-Cl-4-FOO CH 3 H -C (CH 3) 2 - 2-Cl 3-Cl-4-CH 3 OO CH 3 H -C (CH 3) 2 - 2 -Cl 2,5-F 2 -4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl 3,5-F 2 -4-CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 2,4,5-Cl 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 3,4,5-Cl 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4 -CF 2 CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 2,4-F 2 -3,5-Cl 2 OO CH 3 H -C (CH 3) 2 - 2-Cl 2, 3,4,5,6-F 5 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCH 2 CH 2 CH 2 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 3 -F-4-CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4- (CH 2) 5 CH 3 OO CH 3 H -C (CH 3) 2 - 2-Cl 4-OCOC 6 H 5 OO CH 3 H -CH 2 - 2-F 4-Cl OO CH 3 H -CH 2 - 2-F 4-Br OO ─────────────────── ───────────────

【００６７】[0067]

【表１８】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-F 4-C(CH3)3 O O CH3 H -CH2- 2-F 4-Q54 O O CH3 H -CH2- 2-F 4-CF3 O O CH3 H -CH2- 2-F 4-CH(CH3)2 O O CH3 H -CH2- 2-F 4-OCHF2 O O CH3 H -CH2- 2-F 4-OCF2Br O O CH3 H -CH2- 2-F 4-OCF3 O O CH3 H -CH2- 2-F 4-OCH2CH2OCH3 O O CH3 H -CH2- 2-F 4-CO2C(CH3)3 O O CH3 H -CH2- 2-F 4-NO2 O O CH3 H -CH2- 2-F 4-Si(CH3)3 O O CH3 H -CH2- 2-F 4-C6H5 O O CH3 H -CH2- 2-F 4-(C6H4-4-Cl) O O CH3 H -CH2- 2-F 4-O(C6H4-4-CF3) O O CH3 H -CH2- 2-F 4-CH2CH2OCH2CH3 O O CH3 H -CH2- 2-F 3,4-Cl2 O O CH3 H -CH2- 2-F 3-Cl-4-Br O O CH3 H -CH2- 2-F 3-CF3-4-Cl O O CH3 H -CH2- 2-F 2,4,5-Cl3 O O CH3 H -CH2- 2-F 3,4,5-Cl3 O O CH3 H -CH2- 2,6-F2 4-Cl O O CH3 H -CH2- 2,6-F2 4-Br O O ──────────────────────────────────[Table 18] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-F 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-F 4-Q54 OO CH 3 H -CH 2 - 2-F 4-CF 3 OO CH 3 H -CH 2 - 2-F 4- CH (CH 3) 2 OO CH 3 H -CH 2 - 2-F 4-OCHF 2 OO CH 3 H -CH 2 - 2-F 4-OCF 2 Br OO CH 3 H -CH 2 - 2-F 4- OCF 3 OO CH 3 H -CH 2 - 2-F 4-OCH 2 CH 2 OCH 3 OO CH 3 H -CH 2 - 2-F 4-CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 2-F 4-NO 2 OO CH 3 H -CH 2 - 2-F 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 2-F 4-C 6 H 5 OO CH 3 H -CH 2 - 2-F 4- (C 6 H 4 -4-Cl) OO CH 3 H -CH 2 - 2-F 4-O (C 6 H 4 -4-CF 3) OO CH 3 H -CH 2 - 2 -F 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH 2 - 2-F 3,4-Cl 2 OO CH 3 H -CH 2 - 2-F 3-Cl-4-Br OO CH 3 H -CH 2 - 2-F 3 -CF 3 -4-Cl OO CH 3 H -CH 2 - 2-F 2,4,5-Cl 3 OO CH 3 H -CH 2 - 2-F 3,4, 5-Cl 3 OO CH 3 H -CH 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 -2,6-F 2 4-Br OO ───────────────────────────────────

【００６８】[0068]

【表１９】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2,6-F2 4-C(CH3)3 O O CH3 H -CH2- 2,6-F2 4-Q54 O O CH3 H -CH2- 2,6-F2 4-CF3 O O CH3 H -CH2- 2,6-F2 4-CH(CH3)2 O O CH3 H -CH2- 2,6-F2 4-OCHF2 O O CH3 H -CH2- 2,6-F2 4-OCF2Br O O CH3 H -CH2- 2,6-F2 4-OCF3 O O CH3 H -CH2- 2,6-F2 4-OCH2CH2OCH3 O O CH3 H -CH2- 2,6-F2 4-CO2C(CH3)3 O O CH3 H -CH2- 2,6-F2 4-NO2 O O CH3 H -CH2- 2,6-F2 4-Si(CH3)3 O O CH3 H -CH2- 2,6-F2 4-C6H5 O O CH3 H -CH2- 2,6-F2 4-(C6H4-4-Cl) O O CH3 H -CH2- 2,6-F2 4-O(C6H4-4-CF3) O O CH3 H -CH2- 2,6-F2 4-CH2CH2OCH2CH3 O O CH3 H -CH2- 2,6-F2 3,4-Cl2 O O CH3 H -CH2- 2,6-F2 3-Cl-4-Br O O CH3 H -CH2- 2,6-F2 3-CF3-4-Cl O O CH3 H -CH2- 2,6-F2 2,4,5-Cl3 O O CH3 H -CH2- 2,6-F2 3,4,5-Cl3 O O CH3 H -CH2- 4-F 4-Cl O O CH3 H -CH2- 4-F 4-Br O O ──────────────────────────────────[Table 19] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2,6 -F 2 4-C (CH 3 ) 3 OO CH 3 H -CH 2 - 2,6-F 2 4-Q54 OO CH 3 H -CH 2 - 2,6-F 2 4-CF 3 OO CH 3 H -CH 2 - 2,6-F 2 4 -CH (CH 3) 2 OO CH 3 H -CH 2 - 2,6-F 2 4-OCHF 2 OO CH 3 H -CH 2 - 2,6-F 2 4-OCF 2 Br OO CH 3 H -CH 2 - 2,6-F 2 4-OCF 3 OO CH 3 H -CH 2 - 2,6-F 2 4-OCH 2 CH 2 OCH 3 OO CH 3 H - CH 2 - 2,6-F 2 4 -CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 2,6-F 2 4-NO 2 OO CH 3 H -CH 2 - 2,6-F 2 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 2,6-F 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2,6-F 2 4- (C 6 H 4 -4-Cl) OO CH 3 H -CH 2 - 2,6-F 2 4-O (C 6 H 4 -4-CF 3) OO CH 3 H -CH 2 - 2,6-F 2 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH 2 - 2,6-F 2 3,4-Cl 2 OO CH 3 H -CH 2 - 2,6-F 2 3-Cl-4-Br OO CH 3 H -CH 2 - 2,6-F 2 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 2,6-F 2 2,4,5-C l 3 OO CH 3 H -CH 2 -2,6-F 2 3,4,5-Cl 3 OO CH 3 H -CH 2-4 -F 4-Cl OO CH 3 H -CH 2-4 -F 4 -Br OO ──────────────────────────────────

【００６９】[0069]

【表２０】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 4-F 4-C(CH3)3 O O CH3 H -CH2- 4-F 4-Q54 O O CH3 H -CH2- 4-F 4-CF3 O O CH3 H -CH2- 4-F 4-CH(CH3)2 O O CH3 H -CH2- 4-F 4-OCHF2 O O CH3 H -CH2- 4-F 4-OCF2Br O O CH3 H -CH2- 4-F 4-OCF3 O O CH3 H -CH2- 4-F 4-OCH2CH2OCH3 O O CH3 H -CH2- 4-F 4-CO2C(CH3)3 O O CH3 H -CH2- 4-F 4-NO2 O O CH3 H -CH2- 4-F 4-Si(CH3)3 O O CH3 H -CH2- 4-F 4-C6H5 O O CH3 H -CH2- 4-F 4-(C6H4-4-Cl) O O CH3 H -CH2- 4-F 4-O(C6H4-4-CF3) O O CH3 H -CH2- 4-F 4-CH2CH2OCH2CH3 O O CH3 H -CH2- 4-F 3,4-Cl2 O O CH3 H -CH2- 4-F 3-Cl-4-Br O O CH3 H -CH2- 4-F 3-CF3-4-Cl O O CH3 H -CH2- 4-F 2,4,5-Cl3 O O CH3 H -CH2- 4-F 3,4,5-Cl3 O O CH3 H -CH2- 4-Cl 4-Cl O O CH3 H -CH2- 4-Cl 4-Br O O ──────────────────────────────────[Table 20] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2-4 -F 4-C (CH 3 ) 3 OO CH 3 H -CH 2-4 -F 4-Q54 OO CH 3 H -CH 2-4 -F 4-CF 3 OO CH 3 H -CH 2-4 -F 4- CH (CH 3 ) 2 OO CH 3 H -CH 2-4 -F 4-OCHF 2 OO CH 3 H -CH 2-4 -F 4-OCF 2 Br OO CH 3 H -CH 2-4 -F 4- OCF 3 OO CH 3 H -CH 2-4 -F 4-OCH 2 CH 2 OCH 3 OO CH 3 H -CH 2-4 -F 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH 2- 4-F 4-NO 2 OO CH 3 H -CH 2-4 -F 4-Si (CH 3 ) 3 OO CH 3 H -CH 2-4 -F 4-C 6 H 5 OO CH 3 H -CH 2 -4-F 4- (C 6 H 4 -4-Cl) OO CH 3 H -CH 2-4 -F 4-O (C 6 H 4 -4-CF 3 ) OO CH 3 H -CH 2-4 -F 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH 2-4 -F 3,4-Cl 2 OO CH 3 H -CH 2-4 -F 3-Cl-4-Br OO CH 3 H -CH 2-4 -F 3-CF 3 -4-Cl OO CH 3 H -CH 2-4 -F 2,4,5-Cl 3 OO CH 3 H -CH 2-4 -F 3,4, 5-Cl 3 OO CH 3 H -CH 2-4 -Cl 4-Cl OO CH 3 H- CH 2-4 -Cl 4-Br OO ──────────────────────────────────

【００７０】[0070]

【表２１】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 4-Cl 4-C(CH3)3 O O CH3 H -CH2- 4-Cl 4-Q54 O O CH3 H -CH2- 4-Cl 4-CF3 O O CH3 H -CH2- 4-Cl 4-CH(CH3)2 O O CH3 H -CH2- 4-Cl 4-OCHF2 O O CH3 H -CH2- 4-Cl 4-OCF2Br O O CH3 H -CH2- 4-Cl 4-OCF3 O O CH3 H -CH2- 4-Cl 4-OCH2CH2OCH3 O O CH3 H -CH2- 4-Cl 4-CO2C(CH3)3 O O CH3 H -CH2- 4-Cl 4-NO2 O O CH3 H -CH2- 4-Cl 4-Si(CH3)3 O O CH3 H -CH2- 4-Cl 4-C6H5 O O CH3 H -CH2- 4-Cl 4-(C6H4-4-Cl) O O CH3 H -CH2- 4-Cl 4-O(C6H4-4-CF3) O O CH3 H -CH2- 4-Cl 4-CH2CH2OCH2CH3 O O CH3 H -CH2- 4-Cl 3,4-Cl2 O O CH3 H -CH2- 4-Cl 3-Cl-4-Br O O CH3 H -CH2- 4-Cl 3-CF3-4-Cl O O CH3 H -CH2- 4-Cl 2,4,5-Cl3 O O CH3 H -CH2- 4-Cl 3,4,5-Cl3 O O H H -CH2- 2-Cl 4-Cl O O H H -CH2- 2-Cl 4-Br O O ──────────────────────────────────[Table 21] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2-4 -Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2-4 -Cl 4-Q54 OO CH 3 H -CH 2-4 -Cl 4-CF 3 OO CH 3 H -CH 2-4 -Cl 4- CH (CH 3 ) 2 OO CH 3 H -CH 2-4 -Cl 4-OCHF 2 OO CH 3 H -CH 2-4 -Cl 4-OCF 2 Br OO CH 3 H -CH 2-4 -Cl 4- OCF 3 OO CH 3 H -CH 2-4 -Cl 4-OCH 2 CH 2 OCH 3 OO CH 3 H -CH 2-4 -Cl 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH 2- 4-Cl 4-NO 2 OO CH 3 H -CH 2-4 -Cl 4-Si (CH 3 ) 3 OO CH 3 H -CH 2-4 -Cl 4-C 6 H 5 OO CH 3 H -CH 2 -4-Cl 4- (C 6 H 4 -4-Cl) OO CH 3 H -CH 2-4 -Cl 4-O (C 6 H 4 -4-CF 3 ) OO CH 3 H -CH 2-4 -Cl 4-CH 2 CH 2 OCH 2 CH 3 OO CH 3 H -CH 2-4 -Cl 3,4-Cl 2 OO CH 3 H -CH 2-4 -Cl 3-Cl-4-Br OO CH 3 H -CH 2-4 -Cl 3-CF 3 -4-Cl OO CH 3 H -CH 2-4 -Cl 2,4,5-Cl 3 OO CH 3 H -CH 2-4 -Cl 3,4, 5-Cl 3 oOHH -CH 2 - 2-Cl 4 -Cl OOHH -CH 2 - 2-Cl 4-Br OO ──────────────────────────────────

【００７１】[0071]

【表２２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── H H -CH2- 2-Cl 4-C(CH3)3 O O H H -CH2- 2-Cl 4-Q54 O O H H -CH2- 2-Cl 4-CF3 O O H H -CH2- 2-Cl 4-CH(CH3)2 O O H H -CH2- 2-Cl 4-OCHF2 O O H H -CH2- 2-Cl 4-OCF2Br O O H H -CH2- 2-Cl 4-OCF3 O O H H -CH2- 2-Cl 4-OCH2CH2OCH3 O O H H -CH2- 2-Cl 4-CO2C(CH3)3 O O H H -CH2- 2-Cl 4-NO2 O O H H -CH2- 2-Cl 4-Si(CH3)3 O O H H -CH2- 2-Cl 4-C6H5 O O H H -CH2- 2-Cl 4-(C6H4-4-Cl) O O H H -CH2- 2-Cl 4-O(C6H4-4-CF3) O O H H -CH2- 2-Cl 4-CH2CH2OCH2CH3 O O H H -CH2- 2-Cl 3,4-Cl2 O O H H -CH2- 2-Cl 3-Cl-4-Br O O H H -CH2- 2-Cl 3-CF3-4-Cl O O H H -CH2- 2-Cl 2,4,5-Cl3 O O H H -CH2- 2-Cl 3,4,5-Cl3 O O CH3 H -CH2- 2-CF3 4-Cl O O CH3 H -CH2- 2-CF3 4-Br O O ──────────────────────────────────[Table 22] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── HH -CH 2 - 2-Cl 4- C (CH 3) 3 oOHH -CH 2 - 2-Cl 4-Q54 oOHH -CH 2 - 2-Cl 4-CF 3 oOHH -CH 2 - 2-Cl 4-CH (CH 3) 2 oOHH -CH 2 - 2-Cl 4-OCHF 2 oOHH -CH 2 - 2-Cl 4-OCF 2 Br oOHH -CH 2 - 2-Cl 4-OCF 3 oOHH -CH 2 - 2-Cl 4-OCH 2 CH 2 OCH 3 oOHH - CH 2 - 2-Cl 4- CO 2 C (CH 3) 3 oOHH -CH 2 - 2-Cl 4-NO 2 oOHH -CH 2 - 2-Cl 4-Si (CH 3) 3 oOHH -CH 2 - 2 -Cl 4-C 6 H 5 oOHH -CH 2 - 2-Cl 4- (C 6 H 4 -4-Cl) oOHH -CH 2 - 2-Cl 4-O (C 6 H 4 -4-CF 3) oOHH -CH 2 - 2-Cl 4 -CH 2 CH 2 OCH 2 CH 3 oOHH -CH 2 - 2-Cl 3,4-Cl 2 oOHH -CH 2 - 2-Cl 3-Cl-4-Br oOHH -CH 2 - 2-Cl 3-CF 3 -4-Cl oOHH -CH 2 - 2-Cl 2,4,5-Cl 3 oOHH -CH 2 - 2-Cl 3,4,5-Cl 3 OO CH 3 H - CH 2 - 2-CF 3 4 -Cl OO CH 3 H -CH 2 - 2-CF 3 4-Br OO ────────────────── ───────────────

【００７２】[0072]

【表２３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-CF3 4-C(CH3)3 O O CH3 H -CH2- 2-CF3 4-CF3 O O CH3 H -CH2- 2-CF3 4-CO2C(CH3)3 O O CH3 H -CH2- 2-CF3 4-Si(CH3)3 O O CH3 H -CH2- 2-CF3 4-C6H5 O O CH3 H -CH2- 2-CF3 3,4-Cl2 O O CH3 H -CH2- 2-CF3 3-Cl-4-Br O O CH3 H -CH2- 2-CF3 3-CF3-4-Cl O O CH3 H -CH2- 2-CF3 2,4,5-Cl3 O O CH3 H -CH2- 2-Br 4-Cl O O CH3 H -CH2- 2-Br 4-Br O O CH3 H -CH2- 2-Br 4-C(CH3)3 O O CH3 H -CH2- 2-Br 4-CF3 O O CH3 H -CH2- 2-Br 4-CO2C(CH3)3 O O CH3 H -CH2- 2-Br 4-Si(CH3)3 O O CH3 H -CH2- 2-Br 4-C6H5 O O CH3 H -CH2- 2-Br 3,4-Cl2 O O CH3 H -CH2- 2-Br 3-Cl-4-Br O O CH3 H -CH2- 2-Br 3-CF3-4-Cl O O CH3 H -CH2- 2-Br 2,4,5-Cl3 O O CH3 H -CH2- 4-Br 4-Cl O O CH3 H -CH2- 4-Br 4-Br O O ──────────────────────────────────[Table 23] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-CF 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-CF 3 4-CF 3 OO CH 3 H -CH 2 - 2-CF 3 4-CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 2-CF 3 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 2-CF 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-CF 3 3,4 -Cl 2 OO CH 3 H -CH 2 - 2-CF 3 3-Cl-4-Br OO CH 3 H -CH 2 - 2-CF 3 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 2-CF 3 2,4,5-Cl 3 OO CH 3 H -CH 2 - 2-Br 4-Cl OO CH 3 H -CH 2 - 2-Br 4-Br OO CH 3 H -CH 2 - 2- Br 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-Br 4-CF 3 OO CH 3 H -CH 2 - 2-Br 4-CO 2 C (CH 3) 3 OO CH 3 H - CH 2 - 2-Br 4- Si (CH 3) 3 OO CH 3 H -CH 2 - 2-Br 4-C 6 H 5 OO CH 3 H -CH 2 - 2-Br 3,4-Cl 2 OO CH 3 H -CH 2 - 2-Br 3-Cl-4-Br OO CH 3 H -CH 2 - 2-Br 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 2-Br 2,4, 5-Cl 3 OO CH 3 H -CH 2-4 -Br 4-Cl OO CH 3 H -CH 2-4 -Br 4-Br OO ───────────────────────────────────

【００７３】[0073]

【表２４】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 4-Br 4-C(CH3)3 O O CH3 H -CH2- 4-Br 4-CF3 O O CH3 H -CH2- 4-Br 4-CO2C(CH3)3 O O CH3 H -CH2- 4-Br 4-Si(CH3)3 O O CH3 H -CH2- 4-Br 4-C6H5 O O CH3 H -CH2- 4-Br 3,4-Cl2 O O CH3 H -CH2- 4-Br 3-Cl-4-Br O O CH3 H -CH2- 4-Br 3-CF3-4-Cl O O CH3 H -CH2- 4-Br 2,4,5-Cl3 O O CH3 H -CH2- 2-Cl-6-F 4-Cl O O CH3 H -CH2- 2-Cl-6-F 4-Br O O CH3 H -CH2- 2-Cl-6-F 4-C(CH3)3 O O CH3 H -CH2- 2-Cl-6-F 4-CF3 O O CH3 H -CH2- 2-Cl-6-F 4-CO2C(CH3)3 O O CH3 H -CH2- 2-Cl-6-F 4-Si(CH3)3 O O CH3 H -CH2- 2-Cl-6-F 4-C6H5 O O CH3 H -CH2- 2-Cl-6-F 3,4-Cl2 O O CH3 H -CH2- 2-Cl-6-F 3-Cl-4-Br O O CH3 H -CH2- 2-Cl-6-F 3-CF3-4-Cl O O CH3 H -CH2- 2-Cl-6-F 2,4,5-Cl3 O O CH3 H -CH2- 3,4-Cl2 4-Cl O O CH3 H -CH2- 3,4-Cl2 4-Br O O ──────────────────────────────────[Table 24] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2-4 -Br 4-C (CH 3 ) 3 OO CH 3 H -CH 2-4 -Br 4-CF 3 OO CH 3 H -CH 2-4 -Br 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH 2-4 -Br 4-Si (CH 3 ) 3 OO CH 3 H -CH 2-4 -Br 4-C 6 H 5 OO CH 3 H -CH 2-4 -Br 3,4-Cl 2 OO CH 3 H-CH 2-4 -Br 3-Cl-4-Br OO CH 3 H -CH 2-4 -Br 3-CF 3 -4-Cl OO CH 3 H -CH 2-4 -Br 2,4,5 -Cl 3 OO CH 3 H -CH 2 - 2-Cl-6-F 4-Cl OO CH 3 H -CH 2 - 2-Cl-6-F 4-Br OO CH 3 H -CH 2 - 2-Cl -6-F 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl-6-F 4-CF 3 OO CH 3 H -CH 2 - 2-Cl-6-F 4-CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl-6-F 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl-6-F 4-C 6 H 5 OO CH 3 H -CH 2 - 2 -Cl-6-F 3,4-Cl 2 OO CH 3 H -CH 2 - 2-Cl-6-F 3-Cl-4-Br OO CH 3 H -CH 2 - 2-Cl-6-F 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 2-Cl-6-F 2,4,5-Cl 3 OO CH 3 H -CH 2 - 3,4-Cl 2 4-Cl OO CH 3 H -CH 2 - 3,4-Cl 2 4-Br OO ────────────────── ────────────────

【００７４】[0074]

【表２５】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 3,4-Cl2 4-C(CH3)3 O O CH3 H -CH2- 3,4-Cl2 4-CF3 O O CH3 H -CH2- 3,4-Cl2 4-CO2C(CH3)3 O O CH3 H -CH2- 3,4-Cl2 4-Si(CH3)3 O O CH3 H -CH2- 3,4-Cl2 4-C6H5 O O CH3 H -CH2- 3,4-Cl2 3,4-Cl2 O O CH3 H -CH2- 3,4-Cl2 3-Cl-4-Br O O CH3 H -CH2- 3,4-Cl2 3-CF3-4-Cl O O CH3 H -CH2- 3,4-Cl2 2,4,5-Cl3 O O CH2CH3 H -CH2- 2-Cl 4-Cl O O CH2CH3 H -CH2- 2-Cl 4-Br O O CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH2CH3 H -CH2- 2-Cl 4-CF3 O O CH2CH3 H -CH2- 2-Cl 4-CO2C(CH3)3 O O CH2CH3 H -CH2- 2-Cl 4-Si(CH3)3 O O CH2CH3 H -CH2- 2-Cl 4-C6H5 O O CH2CH3 H -CH2- 2-Cl 3,4-Cl2 O O CH2CH3 H -CH2- 2-Cl 3-Cl-4-Br O O CH2CH3 H -CH2- 2-Cl 3-CF3-4-Cl O O CH2CH3 H -CH2- 2-Cl 2,4,5-Cl3 O O ──────────────────────────────────[Table 25] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 3,4 -Cl 2 4-C (CH 3 ) 3 OO CH 3 H -CH 2 - 3,4-Cl 2 4-CF 3 OO CH 3 H -CH 2 - 3,4-Cl 2 4-CO 2 C (CH 3) 3 OO CH 3 H -CH 2 - 3,4-Cl 2 4-Si (CH 3) 3 OO CH 3 H -CH 2 - 3,4-Cl 2 4-C 6 H 5 OO CH 3 H - CH 2 - 3,4-Cl 2 3,4 -Cl 2 OO CH 3 H -CH 2 - 3,4-Cl 2 3-Cl-4-Br OO CH 3 H -CH 2 - 3,4-Cl 2 3-CF 3 -4-Cl OO CH 3 H -CH 2 - 3,4-Cl 2 2,4,5-Cl 3 OO CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO CH 2 CH 3 H -CH 2 - 2-Cl 4-Br OO CH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 CH 3 H -CH 2 - 2-Cl 4-CF 3 OO CH 2 CH 3 H -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 2 CH 3 H -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 2 CH 3 H -CH 2 - 2-Cl 4- C 6 H 5 OO CH 2 CH 3 H -CH 2 - 2-Cl 3,4-Cl 2 OO CH 2 CH 3 H -CH 2 - 2-Cl 3-Cl-4 -Br OO CH 2 CH 3 H -CH 2 - 2-Cl 3-CF 3 -4-Cl OO CH 2 CH 3 H -CH 2 - 2-Cl 2,4,5-Cl 3 OO ──────────────────────────── ──────

【００７５】[0075]

【表２６】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH2CH=CH2 H -CH2- 2-Cl 4-Cl O O CH2CH=CH2 H -CH2- 2-Cl 4-Br O O CH2CH=CH2 H -CH2- 2-Cl 4-C(CH3)3 O O CH2CH=CH2 H -CH2- 2-Cl 4-CF3 O O CH2CH=CH2 H -CH2- 2-Cl 4-CO2C(CH3)3 O O CH2CH=CH2 H -CH2- 2-Cl 4-Si(CH3)3 O O CH2CH=CH2 H -CH2- 2-Cl 4-C6H5 O O CH2CH=CH2 H -CH2- 2-Cl 3,4-Cl2 O O CH2CH=CH2 H -CH2- 2-Cl 3-Cl-4-Br O O CH2CH=CH2 H -CH2- 2-Cl 3-CF3-4-Cl O O CH2CH=CH2 H -CH2- 2-Cl 2,4,5-Cl3 O O CH2OCH3 H -CH2- 2-Cl 4-Cl O O CH2OCH3 H -CH2- 2-Cl 4-Br O O CH2OCH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH2OCH3 H -CH2- 2-Cl 4-CF3 O O CH2OCH3 H -CH2- 2-Cl 4-CO2C(CH3)3 O O CH2OCH3 H -CH2- 2-Cl 4-Si(CH3)3 O O CH2OCH3 H -CH2- 2-Cl 4-C6H5 O O CH2OCH3 H -CH2- 2-Cl 3,4-Cl2 O O CH2OCH3 H -CH2- 2-Cl 3-Cl-4-Br O O CH2OCH3 H -CH2- 2-Cl 3-CF3-4-Cl O O CH2OCH3 H -CH2- 2-Cl 2,4,5-Cl3 O O ──────────────────────────────────[Table 26] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-Cl OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-Br OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-CF 3 OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4- Si (CH 3) 3 OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 4-C 6 H 5 OO CH 2 CH = CH 2 H -CH 2 - 2- Cl 3,4-Cl 2 OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 3-Cl-4-Br OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 3-CF 3 -4 -Cl OO CH 2 CH = CH 2 H -CH 2 - 2-Cl 2,4,5-Cl 3 OO CH 2 OCH 3 H -CH 2 - 2-Cl 4-Cl OO CH 2 OCH 3 H -CH 2 - 2-Cl 4-Br OO CH 2 OCH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 OCH 3 H -CH 2 - 2-Cl 4-CF 3 OO CH 2 OCH 3 H -CH 2 - 2-Cl 4 -CO 2 C (CH 3) 3 OO CH 2 OCH 3 H -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 2 OCH 3 H -CH 2 - 2 -Cl 4-C 6 H 5 O O CH 2 OCH 3 H -CH 2 - 2-Cl 3,4-Cl 2 OO CH 2 OCH 3 H -CH 2 - 2-Cl 3-Cl-4-Br OO CH 2 OCH 3 H -CH 2 - 2 -Cl 3-CF 3 -4-Cl OO CH 2 OCH 3 H -CH 2 - 2-Cl 2,4,5-Cl 3 OO ────────────────── ────────────────

【００７６】[0076]

【表２７】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH2C6H5 H -CH2- 2-Cl 4-Cl O O CH2C6H5 H -CH2- 2-Cl 4-Br O O CH2C6H5 H -CH2- 2-Cl 4-C(CH3)3 O O CH2C6H5 H -CH2- 2-Cl 4-CF3 O O CH2C6H5 H -CH2- 2-Cl 4-CO2C(CH3)3 O O CH2C6H5 H -CH2- 2-Cl 4-Si(CH3)3 O O CH2C6H5 H -CH2- 2-Cl 4-C6H5 O O CH2C6H5 H -CH2- 2-Cl 3,4-Cl2 O O CH2C6H5 H -CH2- 2-Cl 3-Cl-4-Br O O CH2C6H5 H -CH2- 2-Cl 3-CF3-4-Cl O O CH2C6H5 H -CH2- 2-Cl 2,4,5-Cl3 O O CH3 H -CH2- 2-Cl 4-Cl S O CH3 H -CH2- 2-Cl 4-Br S O CH3 H -CH2- 2-Cl 4-C(CH3)3 S O CH3 H -CH2- 2-Cl 4-CF3 S O CH3 H -CH2- 2-Cl 4-CO2C(CH3)3 S O CH3 H -CH2- 2-Cl 4-Si(CH3)3 S O CH3 H -CH2- 2-Cl 4-C6H5 S O CH3 H -CH2- 2-Cl 3,4-Cl2 S O CH3 H -CH2- 2-Cl 3-Cl-4-Br S O CH3 H -CH2- 2-Cl 3-CF3-4-Cl S O CH3 H -CH2- 2-Cl 2,4,5-Cl3 S O ──────────────────────────────────[Table 27] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-Cl OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-Br OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-CF 3 OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4- Si (CH 3) 3 OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-C 6 H 5 OO CH 2 C 6 H 5 H -CH 2 - 2- Cl 3,4-Cl 2 OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 3-Cl-4-Br OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 3-CF 3 -4 -Cl OO CH 2 C 6 H 5 H -CH 2 - 2-Cl 2,4,5-Cl 3 OO CH 3 H -CH 2 - 2-Cl 4-Cl SO CH 3 H -CH 2 - 2-Cl 4-Br SO CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 SO CH 3 H -CH 2 - 2-Cl 4-CF 3 SO CH 3 H -CH 2 - 2-Cl 4- CO 2 C (CH 3) 3 SO CH 3 H -CH 2 - 2-Cl 4-Si (CH 3) 3 SO CH 3 H -CH 2 - 2-Cl 4-C 6 H 5 SO CH 3 H -CH 2 - 2-Cl 3,4-Cl 2 SO CH 3 H - CH 2 - 2-Cl 3- Cl-4-Br SO CH 3 H -CH 2 - 2-Cl 3-CF 3 -4-Cl SO CH 3 H -CH 2 - 2-Cl 2,4,5-Cl 3 SO ──────────────────────────────────

【００７７】[0077]

【表２８】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-Cl 4-Cl O S CH3 H -CH2- 2-Cl 4-Br O S CH3 H -CH2- 2-Cl 4-C(CH3)3 O S CH3 H -CH2- 2-Cl 4-CF3 O S CH3 H -CH2- 2-Cl 4-CO2C(CH3)3 O S CH3 H -CH2- 2-Cl 4-Si(CH3)3 O S CH3 H -CH2- 2-Cl 4-C6H5 O S CH3 H -CH2- 2-Cl 3,4-Cl2 O S CH3 H -CH2- 2-Cl 3-Cl-4-Br O S CH3 H -CH2- 2-Cl 3-CF3-4-Cl O S CH3 H -CH2- 2-Cl 2,4,5-Cl3 O S CH3 Cl -CH2- 2-Cl 4-Cl O O CH3 Cl -CH2- 2-Cl 4-Br O O CH3 Cl -CH2- 2-Cl 4-C(CH3)3 O O CH3 Cl -CH2- 2-Cl 4-CF3 O O CH3 Cl -CH2- 2-Cl 4-CO2C(CH3)3 O O CH3 Cl -CH2- 2-Cl 4-Si(CH3)3 O O CH3 Cl -CH2- 2-Cl 4-C6H5 O O CH3 Cl -CH2- 2-Cl 3,4-Cl2 O O CH3 Cl -CH2- 2-Cl 3-Cl-4-Br O O CH3 Cl -CH2- 2-Cl 3-CF3-4-Cl O O CH3 Cl -CH2- 2-Cl 2,4,5-Cl3 O O ──────────────────────────────────[Table 28] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-Cl 4-Cl OS CH 3 H -CH 2 - 2-Cl 4-Br OS CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OS CH 3 H -CH 2 - 2-Cl 4-CF 3 OS CH 3 H -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OS CH 3 H -CH 2 - 2-Cl 4-Si (CH 3) 3 OS CH 3 H -CH 2 - 2 -Cl 4-C 6 H 5 OS CH 3 H -CH 2 - 2-Cl 3,4-Cl 2 OS CH 3 H -CH 2 - 2-Cl 3-Cl-4-Br OS CH 3 H -CH 2 - 2-Cl 3-CF 3 -4-Cl OS CH 3 H -CH 2 - 2-Cl 2,4,5-Cl 3 OS CH 3 Cl -CH 2 - 2-Cl 4-Cl OO CH 3 Cl - CH 2 - 2-Cl 4- Br OO CH 3 Cl -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 Cl -CH 2 - 2-Cl 4-CF 3 OO CH 3 Cl -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 3 Cl -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 3 Cl -CH 2 - 2-Cl 4-C 6 H 5 OO CH 3 Cl -CH 2 - 2 -Cl 3,4-Cl 2 OO CH 3 Cl -CH 2 - 2-Cl 3-Cl-4-Br OO CH 3 Cl -CH 2 - 2-Cl 3-CF 3 -4-Cl OO CH 3 Cl -CH 2 - 2 -Cl 2,4,5-Cl 3 OO ──────────────────────────────────

【００７８】[0078]

【表２９】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 Br -CH2- 2-Cl 4-Cl O O CH3 Br -CH2- 2-Cl 4-Br O O CH3 Br -CH2- 2-Cl 4-C(CH3)3 O O CH3 Br -CH2- 2-Cl 4-CF3 O O CH3 Br -CH2- 2-Cl 4-CO2C(CH3)3 O O CH3 Br -CH2- 2-Cl 4-Si(CH3)3 O O CH3 Br -CH2- 2-Cl 4-C6H5 O O CH3 Br -CH2- 2-Cl 3,4-Cl2 O O CH3 Br -CH2- 2-Cl 3-Cl-4-Br O O CH3 Br -CH2- 2-Cl 3-CF3-4-Cl O O CH3 Br -CH2- 2-Cl 2,4,5-Cl3 O O CH3 CH3 -CH2- 2-Cl 4-Cl O O CH3 CH3 -CH2- 2-Cl 4-Br O O CH3 CH3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH3 -CH2- 2-Cl 4-CF3 O O CH3 CH3 -CH2- 2-Cl 4-CO2C(CH3)3 O O CH3 CH3 -CH2- 2-Cl 4-Si(CH3)3 O O CH3 CH3 -CH2- 2-Cl 4-C6H5 O O CH3 CH3 -CH2- 2-Cl 3,4-Cl2 O O CH3 CH3 -CH2- 2-Cl 3-Cl-4-Br O O CH3 CH3 -CH2- 2-Cl 3-CF3-4-Cl O O CH3 CH3 -CH2- 2-Cl 2,4,5-Cl3 O O ──────────────────────────────────[Table 29] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 Br -CH 2 - 2-Cl 4-Cl OO CH 3 Br -CH 2 - 2-Cl 4-Br OO CH 3 Br -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 Br -CH 2 - 2-Cl 4-CF 3 OO CH 3 Br -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 3 Br -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 3 Br -CH 2 - 2 -Cl 4-C 6 H 5 OO CH 3 Br -CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 Br -CH 2 - 2-Cl 3-Cl-4-Br OO CH 3 Br -CH 2 - 2-Cl 3-CF 3 -4-Cl OO CH 3 Br -CH 2 - 2-Cl 2,4,5-Cl 3 OO CH 3 CH 3 -CH 2 - 2-Cl 4-Cl OO CH 3 CH 3 -CH 2 - 2-Cl 4 -Br OO CH 3 CH 3 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CH 3 -CH 2 - 2-Cl 4-CF 3 OO CH 3 CH 3 -CH 2 - 2-Cl 4-CO 2 C (CH 3) 3 OO CH 3 CH 3 -CH 2 - 2-Cl 4-Si (CH 3) 3 OO CH 3 CH 3 -CH 2 - 2- Cl 4-C 6 H 5 OO CH 3 CH 3 -CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 CH 3 -CH 2 - 2-Cl 3-Cl-4-Br OO CH 3 CH 3 - CH 2 - 2-Cl 3- CF 3 -4-Cl OO CH 3 CH 3 -CH 2 - 2-Cl 2,4,5-Cl 3 OO ─────────────────────── ───────────

【００７９】[0079]

【表３０】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)- 2-F 4-Cl O O CH3 H -CH(CH3)- 2-F 4-Br O O CH3 H -CH(CH3)- 2-F 4-C(CH3)3 O O CH3 H -CH(CH3)- 2-F 4-CF3 O O CH3 H -CH(CH3)- 2-F 4-CO2C(CH3)3 O O CH3 H -CH(CH3)- 2-F 4-Si(CH3)3 O O CH3 H -CH(CH3)- 2-F 4-C6H5 O O CH3 H -CH(CH3)- 2-F 3,4-Cl2 O O CH3 H -CH(CH3)- 2-F 3-Cl-4-Br O O CH3 H -CH(CH3)- 2-F 3-CF3-4-Cl O O CH3 H -CH(CH3)- 2-F 2,4,5-Cl3 O O CH3 H -CH(CH3)- 2,6-F2 4-Cl O O CH3 H -CH(CH3)- 2,6-F2 4-Br O O CH3 H -CH(CH3)- 2,6-F2 4-C(CH3)3 O O CH3 H -CH(CH3)- 2,6-F2 4-CF3 O O CH3 H -CH(CH3)- 2,6-F2 4-CO2C(CH3)3 O O CH3 H -CH(CH3)- 2,6-F2 4-Si(CH3)3 O O CH3 H -CH(CH3)- 2,6-F2 4-C6H5 O O CH3 H -CH(CH3)- 2,6-F2 3,4-Cl2 O O CH3 H -CH(CH3)- 2,6-F2 3-Cl-4-Br O O CH3 H -CH(CH3)- 2,6-F2 3-CF3-4-Cl O O CH3 H -CH(CH3)- 2,6-F2 2,4,5-Cl3 O O ──────────────────────────────────[Table 30] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 )- 2-F 4-Cl OO CH 3 H -CH (CH 3 )-2-F 4-Br OO CH 3 H -CH (CH 3 )-2-F 4-C (CH 3 ) 3 OO CH 3 H- CH (CH 3 )-2-F 4-CF 3 OO CH 3 H -CH (CH 3 )-2-F 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2- F 4-Si (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2-F 4-C 6 H 5 OO CH 3 H -CH (CH 3 )-2-F 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-2-F 3-Cl-4-Br OO CH 3 H -CH (CH 3 )-2-F 3-CF 3 -4-Cl OO CH 3 H -CH (CH 3 )-2-F 2,4,5-Cl 3 OO CH 3 H -CH (CH 3 )-2,6-F 2 4-Cl OO CH 3 H -CH (CH 3 )-2,6-F 2 4-Br OO CH 3 H -CH (CH 3 )-2,6-F 2 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2,6-F 2 4-CF 3 OO CH 3 H -CH (CH 3 )-2,6-F 2 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2,6-F 2 4-Si (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-2,6-F 2 4-C 6 H 5 OO CH 3 H -CH (CH 3 )-2,6-F 2 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-2,6-F 2 3-Cl-4-Br OO CH 3 H -CH (CH 3 )-2,6-F 2 3-CF 3 -4-Cl OO CH 3 H- CH (CH 3 )-2,6-F 2 2,4,5-Cl 3 OO ────────────────────────────── ─────

【００８０】[0080]

【表３１】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)- 4-Cl 4-Cl O O CH3 H -CH(CH3)- 4-Cl 4-Br O O CH3 H -CH(CH3)- 4-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)- 4-Cl 4-CF3 O O CH3 H -CH(CH3)- 4-Cl 4-CO2C(CH3)3 O O CH3 H -CH(CH3)- 4-Cl 4-Si(CH3)3 O O CH3 H -CH(CH3)- 4-Cl 4-C6H5 O O CH3 H -CH(CH3)- 4-Cl 3,4-Cl2 O O CH3 H -CH(CH3)- 4-Cl 3-Cl-4-Br O O CH3 H -CH(CH3)- 4-Cl 3-CF3-4-Cl O O CH3 H -CH(CH3)- 4-Cl 2,4,5-Cl3 O O CH3 H -CH(CH3)- 4-F 4-Cl O O CH3 H -CH(CH3)- 4-F 4-Br O O CH3 H -CH(CH3)- 4-F 4-C(CH3)3 O O CH3 H -CH(CH3)- 4-F 4-CF3 O O CH3 H -CH(CH3)- 4-F 4-CO2C(CH3)3 O O CH3 H -CH(CH3)- 4-F 4-Si(CH3)3 O O CH3 H -CH(CH3)- 4-F 4-C6H5 O O CH3 H -CH(CH3)- 4-F 3,4-Cl2 O O CH3 H -CH(CH3)- 4-F 3-Cl-4-Br O O CH3 H -CH(CH3)- 4-F 3-CF3-4-Cl O O CH3 H -CH(CH3)- 4-F 2,4,5-Cl3 O O ──────────────────────────────────[Table 31] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 )- 4-Cl 4-Cl OO CH 3 H -CH (CH 3 )-4-Cl 4-Br OO CH 3 H -CH (CH 3 )-4-Cl 4-C (CH 3 ) 3 OO CH 3 H- CH (CH 3 )-4-Cl 4-CF 3 OO CH 3 H -CH (CH 3 )-4-Cl 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-4- Cl 4-Si (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-4-Cl 4-C 6 H 5 OO CH 3 H -CH (CH 3 )-4-Cl 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-4-Cl 3-Cl-4-Br OO CH 3 H -CH (CH 3 )-4-Cl 3-CF 3 -4-Cl OO CH 3 H -CH (CH 3 )-4-Cl 2,4,5-Cl 3 OO CH 3 H -CH (CH 3 )-4-F 4-Cl OO CH 3 H -CH (CH 3 )-4-F 4-Br OO CH 3 H -CH (CH 3 )-4-F 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-4-F 4-CF 3 OO CH 3 H -CH (CH 3 ) -4 -F 4-CO 2 C (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-4-F 4-Si (CH 3 ) 3 OO CH 3 H -CH (CH 3 )-4-F 4- C 6 H 5 OO CH 3 H -CH (CH 3 )-4-F 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-4-F 3-Cl- 4-Br OO CH 3 H -CH (CH 3 )-4-F 3-CF 3 -4-Cl OO CH 3 H -CH (CH 3 )-4-F 2,4,5-Cl 3 OO ── ─────────────────────────────────

【００８１】[0081]

【表３２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2- 2-F 4-Cl O O CH3 H -C(CH3)2- 2-F 4-Br O O CH3 H -C(CH3)2- 2-F 4-C(CH3)3 O O CH3 H -C(CH3)2- 2-F 4-CF3 O O CH3 H -C(CH3)2- 2-F 4-CO2C(CH3)3 O O CH3 H -C(CH3)2- 2-F 4-Si(CH3)3 O O CH3 H -C(CH3)2- 2-F 4-C6H5 O O CH3 H -C(CH3)2- 2-F 3,4-Cl2 O O CH3 H -C(CH3)2- 2-F 3-Cl-4-Br O O CH3 H -C(CH3)2- 2-F 3-CF3-4-Cl O O CH3 H -C(CH3)2- 2-F 2,4,5-Cl3 O O CH3 H -C(CH3)2- 2,6-F2 4-Cl O O CH3 H -C(CH3)2- 2,6-F2 4-Br O O CH3 H -C(CH3)2- 2,6-F2 4-C(CH3)3 O O CH3 H -C(CH3)2- 2,6-F2 4-CF3 O O CH3 H -C(CH3)2- 2,6-F2 4-CO2C(CH3)3 O O CH3 H -C(CH3)2- 2,6-F2 4-Si(CH3)3 O O CH3 H -C(CH3)2- 2,6-F2 4-C6H5 O O CH3 H -C(CH3)2- 2,6-F2 3,4-Cl2 O O CH3 H -C(CH3)2- 2,6-F2 3-Cl-4-Br O O CH3 H -C(CH3)2- 2,6-F2 3-CF3-4-Cl O O CH3 H -C(CH3)2- 2,6-F2 2,4,5-Cl3 O O ──────────────────────────────────[Table 32] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 - 2-F 4-Cl OO CH 3 H -C (CH 3) 2 - 2-F 4-Br OO CH 3 H -C (CH 3) 2 - 2-F 4-C (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-F 4-CF 3 OO CH 3 H -C (CH 3) 2 - 2-F 4-CO 2 C (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-F 4 -Si (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2-F 4-C 6 H 5 OO CH 3 H -C (CH 3) 2 - 2- F 3,4-Cl 2 OO CH 3 H -C (CH 3) 2 - 2-F 3-Cl-4-Br OO CH 3 H -C (CH 3) 2 - 2-F 3-CF 3 -4 -Cl OO CH 3 H -C (CH 3) 2 - 2-F 2,4,5-Cl 3 OO CH 3 H -C (CH 3) 2 - 2,6-F 2 4-Cl OO CH 3 H -C (CH 3) 2 - 2,6 -F 2 4-Br OO CH 3 H -C (CH 3) 2 - 2,6-F 2 4-C (CH 3) 3 OO CH 3 H -C ( CH 3) 2 - 2,6-F 2 4-CF 3 OO CH 3 H -C (CH 3) 2 - 2,6-F 2 4-CO 2 C (CH 3) 3 OO CH 3 H -C ( CH 3) 2 - 2,6-F 2 4-Si (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 2,6-F 2 4-C 6 H 5 OO CH 3 H -C ( CH 3) 2 - 2,6-F 2 3,4-Cl 2 OO CH 3 H -C (CH 3) 2 - 2,6-F 2 3-Cl-4-Br OO CH 3 H -C (CH 3) 2 - 2,6-F 2 3-CF 3 -4-Cl OO CH 3 H -C (CH 3) 2 - 2,6-F 2 2,4,5-Cl 3 OO ───── ─────────────────────────────

【００８２】[0082]

【表３３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2- 4-Cl 4-Cl O O CH3 H -C(CH3)2- 4-Cl 4-Br O O CH3 H -C(CH3)2- 4-Cl 4-C(CH3)3 O O CH3 H -C(CH3)2- 4-Cl 4-CF3 O O CH3 H -C(CH3)2- 4-Cl 4-CO2C(CH3)3 O O CH3 H -C(CH3)2- 4-Cl 4-Si(CH3)3 O O CH3 H -C(CH3)2- 4-Cl 4-C6H5 O O CH3 H -C(CH3)2- 4-Cl 3,4-Cl2 O O CH3 H -C(CH3)2- 4-Cl 3-Cl-4-Br O O CH3 H -C(CH3)2- 4-Cl 3-CF3-4-Cl O O CH3 H -C(CH3)2- 4-Cl 2,4,5-Cl3 O O CH3 H -C(CH3)2- 4-F 4-Cl O O CH3 H -C(CH3)2- 4-F 4-Br O O CH3 H -C(CH3)2- 4-F 4-C(CH3)3 O O CH3 H -C(CH3)2- 4-F 4-CF3 O O CH3 H -C(CH3)2- 4-F 4-CO2C(CH3)3 O O CH3 H -C(CH3)2- 4-F 4-Si(CH3)3 O O CH3 H -C(CH3)2- 4-F 4-C6H5 O O CH3 H -C(CH3)2- 4-F 3,4-Cl2 O O CH3 H -C(CH3)2- 4-F 3-Cl-4-Br O O CH3 H -C(CH3)2- 4-F 3-CF3-4-Cl O O CH3 H -C(CH3)2- 4-F 2,4,5-Cl3 O O ──────────────────────────────────[Table 33] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 -4-Cl 4-Cl OO CH 3 H -C (CH 3 ) 2-4 -Cl 4-Br OO CH 3 H -C (CH 3 ) 2-4 -Cl 4-C (CH 3 ) 3 OO CH 3 H -C (CH 3 ) 2-4 -Cl 4-CF 3 OO CH 3 H -C (CH 3 ) 2-4 -Cl 4-CO 2 C (CH 3 ) 3 OO CH 3 H -C (CH 3) 2 - 4-Cl 4 -Si (CH 3) 3 OO CH 3 H -C (CH 3) 2 - 4-Cl 4-C 6 H 5 OO CH 3 H -C (CH 3) 2 - 4- Cl 3,4-Cl 2 OO CH 3 H -C (CH 3 ) 2-4 -Cl 3-Cl-4-Br OO CH 3 H -C (CH 3 ) 2-4 -Cl 3-CF 3 -4 -Cl OO CH 3 H -C (CH 3 ) 2-4 -Cl 2,4,5-Cl 3 OO CH 3 H -C (CH 3 ) 2-4 -F 4-Cl OO CH 3 H -C ( CH 3 ) 2-4 -F 4-Br OO CH 3 H -C (CH 3 ) 2-4 -F 4-C (CH 3 ) 3 OO CH 3 H -C (CH 3 ) 2-4 -F 4 -CF 3 OO CH 3 H -C (CH 3 ) 2-4 -F 4-CO 2 C (CH 3 ) 3 OO CH 3 H -C (CH 3 ) 2-4 -F 4-Si (CH 3 ) 3 OO CH 3 H -C (CH 3 ) 2-4 -F 4-C 6 H 5 OO CH 3 H -C (CH 3 ) 2-4 -F 3, 4-Cl 2 OO CH 3 H -C (CH 3 ) 2-4 -F 3-Cl-4-Br OO CH 3 H -C (CH 3 ) 2-4 -F 3-CF 3 -4-Cl OO CH 3 H -C (CH 3 ) 2-4 -F 2,4,5-Cl 3 OO ──────────────────────────── ───────

【００８３】[0083]

【表３４】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-CH3 4-Cl O O CH3 H -CH2- 2-CH3 4-Br O O CH3 H -CH2- 2-CH3 4-C(CH3)3 O O CH3 H -CH2- 2-CH3 4-C6H5 O O CH3 H -CH2- 2-CH3 3,4-Cl2 O O CH3 H -CH(CH3)- 2-CH3 4-Cl O O CH3 H -C(CH3)2- 2-CH3 4-Cl O O CH3 H -CH2- 2-OCH3 4-Cl O O CH3 H -CH2- 2-OCH3 4-Br O O CH3 H -CH2- 2-OCH3 4-C(CH3)3 O O CH3 H -CH2- 2-OCH3 4-C6H5 O O CH3 H -CH2- 2-OCH3 3,4-Cl2 O O CH3 H -CH(CH3)- 2-OCH3 4-Cl O O CH3 H -C(CH3)2- 2-OCH3 4-Cl O O CH3 H -CH2- 2,6-Cl2 4-Cl O O CH3 H -CH2- 2,6-Cl2 4-Br O O CH3 H -CH2- 2,6-Cl2 4-C(CH3)3 O O CH3 H -CH2- 2,6-Cl2 4-C6H5 O O CH3 H -CH2- 2,6-Cl2 3,4-Cl2 O O CH3 H -CH2- 2,6-Cl2 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2,6-Cl2 4-Cl O O CH3 H -C(CH3)2- 2,6-Cl2 4-Cl O O ──────────────────────────────────[Table 34] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-CH 3 4-Cl OO CH 3 H -CH 2 - 2-CH 3 4-Br OO CH 3 H -CH 2 - 2-CH 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-CH 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-CH 3 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-CH 3 4-Cl OO CH 3 H -C ( CH 3) 2 - 2-CH 3 4-Cl OO CH 3 H -CH 2 - 2-OCH 3 4-Cl OO CH 3 H -CH 2 - 2-OCH 3 4-Br OO CH 3 H -CH 2 - 2-OCH 3 4-C ( CH 3) 3 OO CH 3 H -CH 2 - 2-OCH 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-OCH 3 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-OCH 3 4-Cl OO CH 3 H -C (CH 3) 2 - 2-OCH 3 4-Cl OO CH 3 H -CH 2 - 2,6-Cl 2 4 -Cl OO CH 3 H -CH 2 - 2,6-Cl 2 4-Br OO CH 3 H -CH 2 - 2,6-Cl 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2 , 6-Cl 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2,6-Cl 2 3,4-Cl 2 OO CH 3 H -CH 2 - 2,6-Cl 2 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2,6-Cl 2 4-Cl OO CH 3 H -C (CH 3) 2 - 2,6-Cl 2 4-Cl OO ──────────────────────── ──────────

【００８４】[0084]

【表３５】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-I 4-Cl O O CH3 H -CH2- 2-I 4-Br O O CH3 H -CH2- 2-I 4-C(CH3)3 O O CH3 H -CH2- 2-I 4-C6H5 O O CH3 H -CH2- 2-I 3,4-Cl2 O O CH3 H -CH(CH3)- 2-I 4-Cl O O CH3 H -C(CH3)2- 2-I 4-Cl O O CH3 H -CH2- 2-CH(CH3)2 4-Cl O O CH3 H -CH2- 2-CH(CH3)2 4-Br O O CH3 H -CH2- 2-CH(CH3)2 4-C(CH3)3 O O CH3 H -CH2- 2-CH(CH3)2 4-C6H5 O O CH3 H -CH2- 2-CH(CH3)2 3,4-Cl2 O O CH3 H -CH(CH3)- 2-CH(CH3)2 4-Cl O O CH3 H -C(CH3)2- 2-CH(CH3)2 4-Cl O O CH3 H -CH2- 2-CN 4-Cl O O CH3 H -CH2- 2-CN 4-Br O O CH3 H -CH2- 2-CN 4-C(CH3)3 O O CH3 H -CH2- 2-CN 4-C6H5 O O CH3 H -CH2- 2-CN 3,4-Cl2 O O CH3 H -CH2- 2-CN 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2-CN 4-Cl O O CH3 H -C(CH3)2- 2-CN 4-Cl O O ──────────────────────────────────[Table 35] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-I 4-Cl OO CH 3 H -CH 2 - 2-I 4-Br OO CH 3 H -CH 2 - 2-I 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-I 4-C 6 H 5 OO CH 3 H -CH 2 - 2-I 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-I 4-Cl OO CH 3 H -C (CH 3) 2 - 2 -I 4-Cl OO CH 3 H -CH 2 - 2-CH (CH 3) 2 4-Cl OO CH 3 H -CH 2 - 2-CH (CH 3) 2 4-Br OO CH 3 H -CH 2 - 2-CH (CH 3) 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-CH (CH 3) 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2-CH (CH 3) 2 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-CH (CH 3) 2 4-Cl OO CH 3 H -C (CH 3) 2 - 2-CH (CH 3) 2 4-Cl OO CH 3 H -CH 2 - 2-CN 4-Cl OO CH 3 H -CH 2 - 2-CN 4-Br OO CH 3 H -CH 2 - 2-CN 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-CN 4-C 6 H 5 OO CH 3 H -CH 2 - 2-CN 3,4-Cl 2 OO CH 3 H -CH 2 - 2-CN 4- OCH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3 )-2-CN 4-Cl OO CH 3 H -C (CH 3 ) 2 - 2-CN 4-Cl OO ─────────────────────────────── ───

【００８５】[0085]

【表３６】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-NO2 4-Cl O O CH3 H -CH2- 2-NO2 4-Br O O CH3 H -CH2- 2-NO2 4-C(CH3)3 O O CH3 H -CH2- 2-NO2 4-C6H5 O O CH3 H -CH2- 2-NO2 3,4-Cl2 O O CH3 H -CH(CH3)- 2-NO2 4-Cl O O CH3 H -C(CH3)2- 2-NO2 4-Cl O O CH3 H -CH2- 2,4,6-F3 4-Cl O O CH3 H -CH2- 2,4,6-F3 4-Br O O CH3 H -CH2- 2,4,6-F3 4-C(CH3)3 O O CH3 H -CH2- 2,4,6-F3 4-C6H5 O O CH3 H -CH2- 2,4,6-F3 3,4-Cl2 O O CH3 H -CH(CH3)- 2,4,6-F3 4-Cl O O CH3 H -C(CH3)2- 2,4,6-F3 4-Cl O O CH3 H -CH2- 2-SCH3 4-Cl O O CH3 H -CH2- 2-SCH3 4-Br O O CH3 H -CH2- 2-SCH3 4-C(CH3)3 O O CH3 H -CH2- 2-SCH3 4-C6H5 O O CH3 H -CH2- 2-SCH3 3,4-Cl2 O O CH3 H -CH2- 2-SCH3 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2-SCH3 4-Cl O O CH3 H -C(CH3)2- 2-SCH3 4-Cl O O ──────────────────────────────────[Table 36] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-NO 2 4-Cl OO CH 3 H -CH 2 - 2-NO 2 4-Br OO CH 3 H -CH 2 - 2-NO 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-NO 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2-NO 2 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-NO 2 4-Cl OO CH 3 H -C ( CH 3) 2 - 2-NO 2 4-Cl OO CH 3 H -CH 2 - 2,4,6-F 3 4-Cl OO CH 3 H -CH 2 - 2,4,6-F 3 4-Br OO CH 3 H -CH 2 - 2,4,6 -F 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2,4,6-F 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2,4,6-F 3 3,4 -Cl 2 OO CH 3 H -CH (CH 3) - 2,4,6-F 3 4-Cl OO CH 3 H -C (CH 3) 2 - 2,4,6-F 3 4- Cl OO CH 3 H -CH 2 - 2-SCH 3 4-Cl OO CH 3 H -CH 2 - 2-SCH 3 4-Br OO CH 3 H -CH 2 - 2-SCH 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-SCH 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-SCH 3 3,4-Cl 2 OO CH 3 H -CH 2 - 2- SCH 3 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3) - 2-SCH 3 4-Cl OO CH 3 H -C (CH 3) 2 - 2-SCH 3 4-Cl OO ─────────────────────── ───────────

【００８６】[0086]

【表３７】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2-CH2Cl 4-Cl O O CH3 H -CH2- 2-CH2Cl 4-Br O O CH3 H -CH2- 2-CH2Cl 4-C(CH3)3 O O CH3 H -CH2- 2-CH2Cl 4-C6H5 O O CH3 H -CH2- 2-CH2Cl 3,4-Cl2 O O CH3 H -CH(CH3)- 2-CH2Cl 4-Cl O O CH3 H -C(CH3)2- 2-CH2Cl 4-Cl O O CH3 H -CH2- 2-OCF3 4-Cl O O CH3 H -CH2- 2-OCF3 4-Br O O CH3 H -CH2- 2-OCF3 4-C(CH3)3 O O CH3 H -CH2- 2-OCF3 4-C6H5 O O CH3 H -CH2- 2-OCF3 3,4-Cl2 O O CH3 H -CH(CH3)- 2-OCF3 4-Cl O O CH3 H -C(CH3)2- 2-OCF3 4-Cl O O CH3 H -CH2- 2-SCF3 4-Cl O O CH3 H -CH2- 2-SCF3 4-Br O O CH3 H -CH2- 2-SCF3 4-C(CH3)3 O O CH3 H -CH2- 2-SCF3 4-C6H5 O O CH3 H -CH2- 2-SCF3 3,4-Cl2 O O CH3 H -CH2- 2-SCF3 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2-SCF3 4-Cl O O CH3 H -C(CH3)2- 2-SCF3 4-Cl O O ──────────────────────────────────[Table 37] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2-CH 2 Cl 4-Cl OO CH 3 H -CH 2 - 2-CH 2 Cl 4-Br OO CH 3 H -CH 2 - 2-CH 2 Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-CH 2 Cl 4-C 6 H 5 OO CH 3 H -CH 2 - 2-CH 2 Cl 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-CH 2 Cl 4-Cl OO CH 3 H -C (CH 3) 2 - 2-CH 2 Cl 4-Cl OO CH 3 H -CH 2 - 2-OCF 3 4-Cl OO CH 3 H -CH 2 - 2-OCF 3 4-Br OO CH 3 H -CH 2 - 2- OCF 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-OCF 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-OCF 3 3 , 4-Cl 2 OO CH 3 H -CH (CH 3) - 2-OCF 3 4-Cl OO CH 3 H -C (CH 3) 2 - 2-OCF 3 4-Cl OO CH 3 H -CH 2 - 2-SCF 3 4-Cl OO CH 3 H -CH 2 - 2-SCF 3 4-Br OO CH 3 H -CH 2 - 2-SCF 3 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-SCF 3 4-C 6 H 5 OO CH 3 H -CH 2 - 2-SCF 3 3,4-Cl 2 OO CH 3 H -CH 2 - 2-SCF 3 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH ( CH 3) - 2-SCF 3 4-Cl OO CH 3 H -C (CH 3) 2 - 2-SCF 3 4-Cl OO ─────────────────── ───────────────

【００８７】[0087]

【表３８】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 2,4-F2 4-Cl O O CH3 H -CH2- 2,4-F2 4-Br O O CH3 H -CH2- 2,4-F2 4-C(CH3)3 O O CH3 H -CH2- 2,4-F2 4-C6H5 O O CH3 H -CH2- 2,4-F2 3,4-Cl2 O O CH3 H -CH(CH3)- 2,4-F2 4-Cl O O CH3 H -C(CH3)2- 2,4-F2 4-Cl O O CH3 H -CH2- 2-Cl-4-F 4-Cl O O CH3 H -CH2- 2-Cl-4-F 4-Br O O CH3 H -CH2- 2-Cl-4-F 4-C(CH3)3 O O CH3 H -CH2- 2-Cl-4-F 4-C6H5 O O CH3 H -CH2- 2-Cl-4-F 3,4-Cl2 O O CH3 H -CH(CH3)- 2-Cl-4-F 4-Cl O O CH3 H -C(CH3)2- 2-Cl-4-F 4-Cl O O CH3 H -CH2- 2,4-Cl2 4-Cl O O CH3 H -CH2- 2,4-Cl2 4-Br O O CH3 H -CH2- 2,4-Cl2 4-C(CH3)3 O O CH3 H -CH2- 2,4-Cl2 4-C6H5 O O CH3 H -CH2- 2,4-Cl2 3,4-Cl2 O O CH3 H -CH2- 2,4-Cl2 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2,4-Cl2 4-Cl O O CH3 H -C(CH3)2- 2,4-Cl2 4-Cl O O ──────────────────────────────────[Table 38] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 - 2,4 -F 2 4-Cl OO CH 3 H -CH 2 - 2,4-F 2 4-Br OO CH 3 H -CH 2 - 2,4-F 2 4-C (CH 3) 3 OO CH 3 H - CH 2 - 2,4-F 2 4 -C 6 H 5 OO CH 3 H -CH 2 - 2,4-F 2 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2,4- F 2 4-Cl OO CH 3 H -C (CH 3) 2 - 2,4-F 2 4-Cl OO CH 3 H -CH 2 - 2-Cl-4-F 4-Cl OO CH 3 H -CH 2 - 2-Cl-4- F 4-Br OO CH 3 H -CH 2 - 2-Cl-4-F 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2-Cl-4-F 4-C 6 H 5 OO CH 3 H -CH 2 - 2-Cl-4-F 3,4-Cl 2 OO CH 3 H -CH (CH 3) - 2-Cl-4-F 4-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl-4-F 4-Cl OO CH 3 H -CH 2 - 2,4-Cl 2 4-Cl OO CH 3 H -CH 2 - 2,4-Cl 2 4-Br OO CH 3 H -CH 2 - 2,4-Cl 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2,4-Cl 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2,4-Cl 2 3,4 -Cl 2 OO CH 3 H -CH 2 - 2,4-Cl 2 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH (C H 3) - 2,4-Cl 2 4-Cl OO CH 3 H -C (CH 3) 2 - 2,4-Cl 2 4-Cl OO ─────────────── ────────────────────

【００８８】[0088]

【表３９】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2- 4-C6H5 4-Cl O O CH3 H -CH2- 4-C6H5 4-Br O O CH3 H -CH2- 4-C6H5 4-C(CH3)3 O O CH3 H -CH2- 4-C6H5 4-C6H5 O O CH3 H -CH2- 4-C6H5 3,4-Cl2 O O CH3 H -CH(CH3)- 4-C6H5 4-Cl O O CH3 H -C(CH3)2- 4-C6H5 4-Cl O O CH3 H -CH2- 2,6-(OCH3)2 4-Cl O O CH3 H -CH2- 2,6-(OCH3)2 4-Br O O CH3 H -CH2- 2,6-(OCH3)2 4-C(CH3)3 O O CH3 H -CH2- 2,6-(OCH3)2 4-C6H5 O O CH3 H -CH2- 2,6-(OCH3)2 3,4-Cl2 O O CH3 H -CH(CH3)- 2,6-(OCH3)2 4-Cl O O CH3 H -C(CH3)2- 2,6-(OCH3)2 4-Cl O O CH3 H -CH2- 2,5-Cl2 4-Cl O O CH3 H -CH2- 2,5-Cl2 4-Br O O CH3 H -CH2- 2,5-Cl2 4-C(CH3)3 O O CH3 H -CH2- 2,5-Cl2 4-C6H5 O O CH3 H -CH2- 2,5-Cl2 3,4-Cl2 O O CH3 H -CH2- 2,5-Cl2 4-OCH2CH2CH3 O O CH3 H -CH(CH3)- 2,5-Cl2 4-Cl O O CH3 H -C(CH3)2- 2,5-Cl2 4-Cl O O ──────────────────────────────────[Table 39] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2-4 -C 6 H 5 4-Cl OO CH 3 H -CH 2-4 -C 6 H 5 4-Br OO CH 3 H -CH 2-4 -C 6 H 5 4-C (CH 3 ) 3 OO CH 3 H- CH 2-4 -C 6 H 5 4-C 6 H 5 OO CH 3 H -CH 2-4 -C 6 H 5 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-4-C 6 H 5 4-Cl OO CH 3 H -C (CH 3) 2 - 4-C 6 H 5 4-Cl OO CH 3 H -CH 2 - 2,6- (OCH 3) 2 4-Cl OO CH 3 H -CH 2 - 2,6- (OCH 3) 2 4-Br OO CH 3 H -CH 2 - 2,6- (OCH 3) 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2 , 6- (OCH 3 ) 2 4-C 6 H 5 OO CH 3 H -CH 2 -2,6- (OCH 3 ) 2 3,4-Cl 2 OO CH 3 H -CH (CH 3 )-2, 6- (OCH 3 ) 2 4-Cl OO CH 3 H -C (CH 3 ) 2 -2,6- (OCH 3 ) 2 4-Cl OO CH 3 H -CH 2 -2,5-Cl 2 4- Cl OO CH 3 H -CH 2 - 2,5-Cl 2 4-Br OO CH 3 H -CH 2 - 2,5-Cl 2 4-C (CH 3) 3 OO CH 3 H -CH 2 - 2, 5-Cl 2 4-C 6 H 5 OO CH 3 H -CH 2 - 2,5-Cl 2 3,4-Cl 2 OO C H 3 H -CH 2 - 2,5- Cl 2 4-OCH 2 CH 2 CH 3 OO CH 3 H -CH (CH 3) - 2,5-Cl 2 4-Cl OO CH 3 H -C (CH 3 ) 2 - 2,5-Cl 2 4 -Cl OO ──────────────────────────────────

【００８９】[0089]

【表４０】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 F -CH2- 2-Cl 4-Cl O O CH3 F -CH2- 2-Cl 4-C(CH3)3 O O CH3 F -CH(CH3)- 2-Cl 4-Cl O O CH3 F -C(CH3)2- 2-Cl 4-Cl O O CH3 I -CH2- 2-Cl 4-Cl O O CH3 I -CH2- 2-Cl 4-C(CH3)3 O O CH3 I -CH(CH3)- 2-Cl 4-Cl O O CH3 I -C(CH3)2- 2-Cl 4-Cl O O CH3 CH2CH3 -CH2- 2-Cl 4-Cl O O CH3 CH2CH3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH2CH3 -CH(CH3)- 2-Cl 4-Cl O O CH3 CH2CH3 -C(CH3)2- 2-Cl 4-Cl O O CH3 CH(CH3)2 -CH2- 2-Cl 4-Cl O O CH3 CH(CH3)2 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH(CH3)2 -CH(CH3)- 2-Cl 4-Cl O O CH3 CH(CH3)2 -C(CH3)2- 2-Cl 4-Cl O O CH3 CH2CH2CH3 -CH2- 2-Cl 4-Cl O O CH3 CH2CH2CH3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH2CH2CH3 -CH(CH3)- 2-Cl 4-Cl O O CH3 CH2CH2CH3 -C(CH3)2- 2-Cl 4-Cl O O CH3 C(CH3)3 -CH2- 2-Cl 4-Cl O O CH3 C(CH3)3 -CH2- 2-Cl 4-C(CH3)3 O O ──────────────────────────────────[Table 40] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 F -CH 2 - 2-Cl 4-Cl OO CH 3 F -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 F -CH (CH 3) - 2-Cl 4-Cl OO CH 3 F -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 I -CH 2 - 2-Cl 4-Cl OO CH 3 I -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 I -CH (CH 3) - 2-Cl 4-Cl OO CH 3 I -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 CH 2 CH 3 -CH 2 - 2-Cl 4-Cl OO CH 3 CH 2 CH 3 - CH 2 - 2-Cl 4- C (CH 3) 3 OO CH 3 CH 2 CH 3 -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CH 2 CH 3 -C (CH 3) 2 - 2 -Cl 4-Cl OO CH 3 CH (CH 3) 2 -CH 2 - 2-Cl 4-Cl OO CH 3 CH (CH 3) 2 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CH (CH 3) 2 -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CH (CH 3) 2 -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 CH 2 CH 2 CH 3 -CH 2 - 2-Cl 4-Cl OO CH 3 CH 2 CH 2 CH 3 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CH 2 CH 2 CH 3 -CH (CH 3 )-2-Cl 4-Cl OO CH 3 CH 2 CH 2 CH 3 -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 C (CH 3) 3 -CH 2 - 2-Cl 4-Cl OO CH 3 C (CH 3) 3 - CH 2 - 2-Cl 4- C (CH 3) 3 OO ──────────────────────────────────

【００９０】[0090]

【表４１】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 CF3 -CH2- 2-Cl 4-Cl O O CH3 CF3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CF3 -CH(CH3)- 2-Cl 4-Cl O O CH3 CF3 -C(CH3)2- 2-Cl 4-Cl O O CH3 NO2 -CH2- 2-Cl 4-Cl O O CH3 NO2 -CH2- 2-Cl 4-C(CH3)3 O O CH3 NO2 -CH(CH3)- 2-Cl 4-Cl O O CH3 NO2 -C(CH3)2- 2-Cl 4-Cl O O CH3 CH2OCH3 -CH2- 2-Cl 4-Cl O O CH3 CH2OCH3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH2OCH3 -CH(CH3)- 2-Cl 4-Cl O O CH3 CH2OCH3 -C(CH3)2- 2-Cl 4-Cl O O CH3 CH2SCH3 -CH2- 2-Cl 4-Cl O O CH3 CH2SCH3 -CH2- 2-Cl 4-C(CH3)3 O O CH3 CH2SCH3 -CH(CH3)- 2-Cl 4-Cl O O CH3 CH2SCH3 -C(CH3)2- 2-Cl 4-Cl O O CH3 CN -CH2- 2-Cl 4-Cl O O CH3 CN -CH2- 2-Cl 4-C(CH3)3 O O CH3 CN -CH(CH3)- 2-Cl 4-Cl O O CH3 CN -C(CH3)2- 2-Cl 4-Cl O O CH3 CH2Cl -CH2- 2-Cl 4-Cl O O CH3 CH2Cl -CH2- 2-Cl 4-C(CH3)3 O O ──────────────────────────────────[Table 41] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 CF 3 -CH 2 - 2- Cl 4-Cl OO CH 3 CF 3 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CF 3 -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CF 3 -C ( CH 3) 2 - 2-Cl 4-Cl OO CH 3 NO 2 -CH 2 - 2-Cl 4-Cl OO CH 3 NO 2 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 NO 2 -CH (CH 3) - 2 -Cl 4-Cl OO CH 3 NO 2 -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 CH 2 OCH 3 -CH 2 - 2-Cl 4-Cl OO CH 3 CH 2 OCH 3 -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CH 2 OCH 3 -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CH 2 OCH 3 - C (CH 3) 2 - 2 -Cl 4-Cl OO CH 3 CH 2 SCH 3 -CH 2 - 2-Cl 4-Cl OO CH 3 CH 2 SCH 3 -CH 2 - 2-Cl 4-C (CH 3 ) 3 OO CH 3 CH 2 SCH 3 -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CH 2 SCH 3 -C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 CN -CH 2 - 2-Cl 4-Cl OO CH 3 CN -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 CN -CH (CH 3) - 2-Cl 4-Cl OO CH 3 CN -C ( CH 3) 2 - 2-Cl 4 -Cl OO CH 3 CH 2 Cl -CH 2 - 2-Cl 4-Cl OO CH 3 CH 2 Cl -CH 2 - 2-Cl 4-C (CH 3) 3 OO ── ────────────────────────────────

【００９１】[0091]

【表４２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH2CH2CH3 H -CH2- 2-Cl 4-Cl O O CH2CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH2CH2CH3 H -CH(CH3)- 2-Cl 4-Cl O O CH2CH2CH3 H -C(CH3)2- 2-Cl 4-Cl O O CH(CH3)2 H -CH2- 2-Cl 4-Cl O O CH(CH3)2 H -CH2- 2-Cl 4-C(CH3)3 O O CH(CH3)2 H -CH(CH3)- 2-Cl 4-Cl O O CH(CH3)2 H -C(CH3)2- 2-Cl 4-Cl O O C(CH3)3 H -CH2- 2-Cl 4-Cl O O C(CH3)3 H -CH2- 2-Cl 4-C(CH3)3 O O C(CH3)3 H -CH(CH3)- 2-Cl 4-Cl O O C(CH3)3 H -C(CH3)2- 2-Cl 4-Cl O O CH2Ｃ≡CH H -CH2- 2-Cl 4-Cl O O CH2Ｃ≡CH H -CH2- 2-Cl 4-C(CH3)3 O O CH2Ｃ≡CH H -CH(CH3)- 2-Cl 4-Cl O O CH2Ｃ≡CH H -C(CH3)2- 2-Cl 4-Cl O O CHF2 H -CH2- 2-Cl 4-Cl O O CHF2 H -CH2- 2-Cl 4-C(CH3)3 O O CHF2 H -CH(CH3)- 2-Cl 4-Cl O O CHF2 H -C(CH3)2- 2-Cl 4-Cl O O CF2Br H -CH2- 2-Cl 4-Cl O O CF2Br H -CH2- 2-Cl 4-C(CH3)3 O O ──────────────────────────────────[Table 42] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO CH 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 CH 2 CH 3 H -CH (CH 3) - 2-Cl 4- Cl OO CH 2 CH 2 CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CH (CH 3) 2 H -CH 2 - 2-Cl 4-Cl OO CH (CH 3) 2 H - CH 2 - 2-Cl 4- C (CH 3) 3 OO CH (CH 3) 2 H -CH (CH 3) - 2-Cl 4-Cl OO CH (CH 3) 2 H -C (CH 3) 2 - 2-Cl 4-Cl OOC (CH 3) 3 H -CH 2 - 2-Cl 4-Cl OOC (CH 3) 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OOC (CH 3 ) 3 H -CH (CH 3) - 2-Cl 4-Cl OOC (CH 3) 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CH 2 C≡CH H -CH 2 - 2- Cl 4-Cl OO CH 2 C≡CH H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 C≡CH H -CH (CH 3) - 2-Cl 4-Cl OO CH 2 C ≡CH H -C (CH 3) 2 - 2-Cl 4-Cl OO CHF 2 H -CH 2 - 2-Cl 4-Cl OO CHF 2 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CHF 2 H -CH (CH 3 )- 2-Cl 4-Cl OO CHF 2 H -C (CH 3) 2 - 2-Cl 4-Cl OO CF 2 Br H -CH 2 - 2-Cl 4-Cl OO CF 2 Br H -CH 2 - 2- Cl 4-C (CH 3 ) 3 OO ───────────────────────────────────

【００９２】[0092]

【表４３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CF3 H -CH2- 2-Cl 4-Cl O O CF3 H -CH2- 2-Cl 4-C(CH3)3 O O CF3 H -CH(CH3)- 2-Cl 4-Cl O O CF3 H -C(CH3)2- 2-Cl 4-Cl O O CH2OCH2CH3 H -CH2- 2-Cl 4-Cl O O CH2OCH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH2OCH2CH3 H -CH(CH3)- 2-Cl 4-Cl O O CH2OCH2CH3 H -C(CH3)2- 2-Cl 4-Cl O O CHO H -CH2- 2-Cl 4-Cl O O CHO H -CH2- 2-Cl 4-C(CH3)3 O O CHO H -CH(CH3)- 2-Cl 4-Cl O O CHO H -C(CH3)2- 2-Cl 4-Cl O O COCH3 H -CH2- 2-Cl 4-Cl O O COCH3 H -CH2- 2-Cl 4-C(CH3)3 O O COCH3 H -CH(CH3)- 2-Cl 4-Cl O O COCH3 H -C(CH3)2- 2-Cl 4-Cl O O CO2CH2CH3 H -CH2- 2-Cl 4-Cl O O CO2CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CO2CH2CH3 H -CH(CH3)- 2-Cl 4-Cl O O CO2CH2CH3 H -C(CH3)2- 2-Cl 4-Cl O O COCO2CH3 H -CH2- 2-Cl 4-Cl O O COCO2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O ──────────────────────────────────[Table 43] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CF 3 H -CH 2 - 2-Cl 4-Cl OO CF 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CF 3 H -CH (CH 3) - 2-Cl 4-Cl OO CF 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CH 2 OCH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO CH 2 OCH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 2 OCH 2 CH 3 H -CH ( CH 3) - 2-Cl 4-Cl OO CH 2 OCH 2 CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CHO H -CH 2 - 2- Cl 4-Cl OO CHO H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CHO H -CH (CH 3) - 2-Cl 4-Cl OO CHO H -C (CH 3) 2 - 2 -Cl 4-Cl OO COCH 3 H -CH 2 - 2-Cl 4-Cl OO COCH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO COCH 3 H -CH (CH 3) - 2 -Cl 4-Cl OO COCH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO CO 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO CO 2 CH 2 CH 3 H - CH 2 - 2-Cl 4- C (CH 3) 3 OO CO 2 CH 2 CH 3 H -CH (CH 3) - 2-Cl 4-Cl OO CO 2 CH 2 CH 3 H -C (CH 3) 2 -2-Cl 4-Cl OO COCO 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO COCO 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO ───────── ─────────────────────────

【００９３】[0093]

【表４４】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── COCO2CH2CH3 H -CH2- 2-Cl 4-Cl O O COCO2CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O COCO2CH2CH3 H -CH(CH3)- 2-Cl 4-Cl O O COCO2CH2CH3 H -C(CH3)2- 2-Cl 4-Cl O O NH2 H -CH2- 2-Cl 4-Cl O O NH2 H -CH2- 2-Cl 4-C(CH3)3 O O NH2 H -CH(CH3)- 2-Cl 4-Cl O O NH2 H -C(CH3)2- 2-Cl 4-Cl O O CN H -CH2- 2-Cl 4-Cl O O CN H -CH2- 2-Cl 4-C(CH3)3 O O CN H -CH(CH3)- 2-Cl 4-Cl O O CN H -C(CH3)2- 2-Cl 4-Cl O O SC6H5 H -CH2- 2-Cl 4-Cl O O S(C6H4-2-CH3) H -CH2- 2-Cl 4-C(CH3)3 O O S(C6H4-3-CH3) H -CH(CH3)- 2-Cl 4-Cl O O S(C6H4-4-CH3) H -C(CH3)2- 2-Cl 4-Cl O O S(C6H4-4-Cl) H -CH2- 2-Cl 4-Cl O O S(C6H4-4-Br) H -CH2- 2-Cl 4-C(CH3)3 O O S(C6H4-2-CH(CH3)2) H -CH(CH3)- 2-Cl 4-Cl O O S(C6H4-2-NO2) H -C(CH3)2- 2-Cl 4-Cl O O S(C6H4-2-CO2CH3) H -CH2- 2-Cl 4-Cl O O S(C6H4-2,4-(NO2)2) H -CH2- 2-Cl 4-C(CH3)3 O O ──────────────────────────────────[Table 44] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── COCO 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO COCO 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO COCO 2 CH 2 CH 3 H -CH (CH 3) - 2-Cl 4- Cl OO COCO 2 CH 2 CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO NH 2 H -CH 2 - 2-Cl 4-Cl OO NH 2 H -CH 2 - 2-Cl 4- C (CH 3) 3 OO NH 2 H -CH (CH 3) - 2-Cl 4-Cl OO NH 2 H -C (CH 3) 2 - 2-Cl 4-Cl OO CN H -CH 2 - 2- Cl 4-Cl OO CN H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CN H -CH (CH 3) - 2-Cl 4-Cl OO CN H -C (CH 3) 2 - 2 -Cl 4-Cl OO SC 6 H 5 H -CH 2 - 2-Cl 4-Cl OOS (C 6 H 4 -2-CH 3) H -CH 2 - 2-Cl 4-C (CH 3) 3 OOS (C 6 H 4 -3-CH 3) H -CH (CH 3) - 2-Cl 4-Cl OOS (C 6 H 4 -4-CH 3) H -C (CH 3) 2 - 2-Cl 4 -Cl OOS (C 6 H 4 -4 -Cl) H -CH 2 - 2-Cl 4-Cl OOS (C 6 H 4 -4-Br) H -CH 2 - 2-Cl 4-C (CH 3) 3 OOS (C 6 H 4 -2-CH (CH 3 ) 2 ) H -CH (CH 3 ) - 2-Cl 4-Cl OOS (C 6 H 4 -2-NO 2) H -C (CH 3) 2 - 2-Cl 4-Cl OOS (C 6 H 4 -2-CO 2 CH 3) H -CH 2 - 2-Cl 4- Cl OOS (C 6 H 4 -2,4- (NO 2) 2) H -CH 2 - 2-Cl 4-C (CH 3) 3 OO ────── ────────────────────────────

【００９４】[0094]

【表４５】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── SCCl3 H -CH2- 2-Cl 4-Cl O O SCO2CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O SN(CH3)CH2CH2CH3 H -CH(CH3)- 2-Cl 4-Cl O O SN(CH2CH2CH2CH3)2 H -C(CH3)2- 2-Cl 4-Cl O O SN(CH3)CO2CH(CH3)2 H -CH2- 2-Cl 4-Cl O O SN(CH3)CO2CH2CH2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O SN(CH2CH3)CO2CH3 H -CH(CH3)- 2-Cl 4-Cl O O SN(CH(CH3)2)CO2CH3 H -C(CH3)2- 2-Cl 4-Cl O O SN(CH2CH2CH3)CO2CH3 H -CH2- 2-Cl 4-Cl O O SN(CH3)CH2CH2CO2CH3 H -CH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)- 2-Cl 4-Cl S S CH3 H -C(CH3)2- 2-Cl 4-Cl S S CH3 H -CH2- 2-Cl 4-Cl S S CH3 H -CH2- 2-Cl 4-C(CH3)3 S S CH3 H -CH(CH3)- 2-Cl 4-Cl NH O CH3 H -C(CH3)2- 2-Cl 4-Cl NH O CH3 H -CH2- 2-Cl 4-Cl NH O CH3 H -CH2- 2-Cl 4-C(CH3)3 NH O CH3 H -CH(CH3)- 2-Cl 4-Cl O NH CH3 H -C(CH3)2- 2-Cl 4-Cl O NH CH3 H -CH2- 2-Cl 4-Cl O NH CH3 H -CH2- 2-Cl 4-C(CH3)3 O NH ──────────────────────────────────[Table 45] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── SCCl 3 H -CH 2 - 2-Cl 4-Cl OO SCO 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO SN (CH 3) CH 2 CH 2 CH 3 H -CH (CH 3) - 2-Cl 4 -Cl OO SN (CH 2 CH 2 CH 2 CH 3) 2 H -C (CH 3) 2 - 2-Cl 4-Cl OO SN (CH 3) CO 2 CH (CH 3) 2 H -CH 2 - 2 -Cl 4-Cl OO SN (CH 3) CO 2 CH 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO SN (CH 2 CH 3) CO 2 CH 3 H -CH (CH 3) - 2-Cl 4-Cl OO SN (CH (CH 3) 2) CO 2 CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl OO SN (CH 2 CH 2 CH 3) CO 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO SN (CH 3) CH 2 CH 2 CO 2 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H - CH (CH 3) - 2- Cl 4-Cl SS CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl SS CH 3 H -CH 2 - 2-Cl 4-Cl SS CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 SS CH 3 H -CH (CH 3) - 2-Cl 4-Cl NH O CH 3 H -C (CH 3) 2 - 2-Cl 4-Cl NH O CH 3 H -CH 2 - 2 -C l 4-Cl NH O CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 NH O CH 3 H -CH (CH 3) - 2-Cl 4-Cl O NH CH 3 H -C ( CH 3) 2 - 2-Cl 4-Cl O NH CH 3 H -CH 2 - 2-Cl 4-Cl O NH CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 O NH ── ────────────────────────────────

【００９５】[0095]

【表４６】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH2CH3)- 2-Cl 4-Cl O O CH3 H -CH(CH2CH3)- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH2CH3)- 2-F 4-Cl O O CH3 H -CH(CH2CH3)- 2,6-F2 4-Cl O O CH3 H -CH(CH(CH3)2)- 2-Cl 4-Cl O O CH3 H -CH(CH(CH3)2)- 2-Cl 3,4-Cl2 O O CH3 H -CH(CH(CH3)2)- 2-F 4-Cl O O CH3 H -CH(CH(CH3)2)- 4-Cl 4-Cl O O CH3 H -CH(CH2CH2CH2CH3)- 2-Cl 4-Cl O O CH3 H -CH(CH2CH2CH2CH3)- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH2CH2CH2CH3)- 4-F 4-Cl O O CH3 H -CH(CH2CH2CH2CH3)- 2,6-F2 4-Cl O O CH3 H -C(CH3)(CH2CH3)- 2-Cl 4-Cl O O CH3 H -C(CH3)(CH2CH3)- 2-Cl 3,4-Cl2 O O CH3 H -C(CH3)(CH2CH3)- 4-F 4-Cl O O CH3 H -C(CH3)(CH2CH3)- 4-Cl 4-Cl O O CH3 H -CH2CH2- 2-Cl 4-Cl O O CH3 H -CH2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH2- 2-F 4-Cl O O CH3 H -CH2CH2- 2,6-F2 4-Cl O O CH3 H -CH(CH3)CH2- 2-Cl 4-Cl O O CH3 H -CH(CH3)CH2- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 46] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 2 CH 3 )-2-Cl 4-Cl OO CH 3 H -CH (CH 2 CH 3 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 2 CH 3 )-2-F 4- Cl OO CH 3 H -CH (CH 2 CH 3 )-2,6-F 2 4-Cl OO CH 3 H -CH (CH (CH 3 ) 2 )-2-Cl 4-Cl OO CH 3 H -CH (CH (CH 3 ) 2 )-2-Cl 3,4-Cl 2 OO CH 3 H -CH (CH (CH 3 ) 2 )-2-F 4-Cl OO CH 3 H -CH (CH (CH 3 ) 2 )-4-Cl 4-Cl OO CH 3 H -CH (CH 2 CH 2 CH 2 CH 3 )-2-Cl 4-Cl OO CH 3 H -CH (CH 2 CH 2 CH 2 CH 3 )- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 2 CH 2 CH 2 CH 3 )-4-F 4-Cl OO CH 3 H -CH (CH 2 CH 2 CH 2 CH 3 ) -2,6-F 2 4-Cl OO CH 3 H -C (CH 3 ) (CH 2 CH 3 )-2-Cl 4-Cl OO CH 3 H -C (CH 3 ) (CH 2 CH 3 )- 2-Cl 3,4-Cl 2 OO CH 3 H -C (CH 3 ) (CH 2 CH 3 )-4-F 4-Cl OO CH 3 H -C (CH 3 ) (CH 2 CH 3 )-4 -Cl 4-Cl OO CH 3 H -CH 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 CH 2 - 2-F 4-Cl OO CH 3 H -CH 2 CH 2 - 2,6-F 2 4 -Cl OO CH 3 H -CH (CH 3) CH 2 - 2-Cl 4-Cl OO CH 3 H -CH (CH 3) CH 2 - 2,6-F 2 4-Cl OO ────── ────────────────────────────

【００９６】[0096]

【表４７】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -C(CH3)2CH2- 2-Cl 4-Cl O O CH3 H -C(CH3)2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -C(CH3)2CH2- 2-F 4-Cl O O CH3 H -C(CH3)2CH2- 2,6-F2 4-Cl O O CH3 H -CH2CH(CH3)- 2-Cl 4-Cl O O CH3 H -CH2CH(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH(CH3)- 2-F 4-Cl O O CH3 H -CH2CH(CH3)- 4-Cl 4-Cl O O CH3 H -CH2C(CH3)2- 2-Cl 4-Cl O O CH3 H -CH2C(CH3)2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2C(CH3)2- 4-F 4-Cl O O CH3 H -CH2C(CH3)2- 2,6-F2 4-Cl O O CH3 H -CH2CH2CH2- 2-Cl 4-Cl O O CH3 H -CH2CH2CH2- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH2CH2- 4-F 4-Cl O O CH3 H -CH2CH2CH2- 4-Cl 4-Cl O O CH3 H -CH(CH3)CH2CH2- 2-Cl 4-Cl O O CH3 H -CH(CH3)CH2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)CH2CH2- 2-F 4-Cl O O CH3 H -CH(CH3)CH2CH2- 2,6-F2 4-Cl O O CH3 H -CH2CH(CH3)CH2- 2-Cl 4-Cl O O CH3 H -CH2CH(CH3)CH2- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 47] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -C (CH 3 ) 2 CH 2 - 2-Cl 4- Cl OO CH 3 H -C (CH 3) 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -C (CH 3) 2 CH 2 - 2- F 4-Cl OO CH 3 H -C (CH 3) 2 CH 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH (CH 3) - 2-Cl 4-Cl OO CH 3 H -CH 2 CH (CH 3 )-2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CH (CH 3 )-2-F 4-Cl OO CH 3 H -CH 2 CH (CH 3 )- 4-Cl 4-Cl OO CH 3 H -CH 2 C (CH 3) 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 C (CH 3) 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 C (CH 3) 2 - 4-F 4-Cl OO CH 3 H -CH 2 C (CH 3) 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 - 2- Cl 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CH 2 CH 2 - 4-F 4- Cl OO CH 3 H -CH 2 CH 2 CH 2 - 4-Cl 4-Cl OO CH 3 H -CH (CH 3) CH 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -CH (CH 3) CH 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH (CH 3) CH 2 CH 2 - 2-F 4-Cl OO CH 3 H -CH (CH 3) CH 2 CH 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH (CH 3) CH 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 CH (CH 3) CH 2 - 2,6-F 2 4-Cl OO ────────── ────────────────────────

【００９７】[0097]

【表４８】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2CH2C(CH3)2- 2-Cl 4-Cl O O CH3 H -CH2CH2C(CH3)2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH2C(CH3)2- 2-F 4-Cl O O CH3 H -CH2CH2C(CH3)2- 2,6-F2 4-Cl O O CH3 H -CH2CH2CH2CH2- 2-Cl 4-Cl O O CH3 H -CH2CH2CH2CH2- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH2CH2CH2- 2-F 4-Cl O O CH3 H -CH2CH2CH2CH2- 4-Cl 4-Cl O O CH3 H -CH=CH- 2-Cl 4-Cl O O CH3 H -CH=CH- 2-Cl 4-C(CH3)3 O O CH3 H -CH=CH- 4-F 4-Cl O O CH3 H -CH=CH- 2,6-F2 4-Cl O O CH3 H -C(CH3)=CH- 2-Cl 4-Cl O O CH3 H -C(CH3)=CH- 2-Cl 3,4-Cl2 O O CH3 H -C(CH3)=CH- 4-F 4-Cl O O CH3 H -C(CH3)=CH- 4-Cl 4-Cl O O CH3 H -CH2CH=CH- 2-Cl 4-Cl O O CH3 H -CH2CH=CH- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH=CH- 2-F 4-Cl O O CH3 H -CH2CH=CH- 2,6-F2 4-Cl O O CH3 H -CH2CH=CH- 2-Cl 4-Cl O S H H -CH2CH=CH- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 48] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 CH 2 C ( CH 3) 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 C (CH 3) 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 CH 2 C (CH 3) 2 - 2-F 4 -Cl OO CH 3 H -CH 2 CH 2 C (CH 3) 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 CH 2 - 2 -Cl 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CH 2 CH 2 CH 2 - 2-F 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 CH 2-4 -Cl 4-Cl OO CH 3 H -CH = CH- 2-Cl 4-Cl OO CH 3 H -CH = CH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH = CH- 4-F 4-Cl OO CH 3 H -CH = CH- 2,6-F 2 4-Cl OO CH 3 H -C (CH 3 ) = CH- 2 -Cl 4-Cl OO CH 3 H -C (CH 3 ) = CH- 2-Cl 3,4-Cl 2 OO CH 3 H -C (CH 3 ) = CH- 4-F 4-Cl OO CH 3 H -C (CH 3 ) = CH- 4-Cl 4-Cl OO CH 3 H -CH 2 CH = CH- 2-Cl 4-Cl OO CH 3 H -CH 2 CH = CH- 2-Cl 4-C ( CH 3 ) 3 OO CH 3 H -CH 2 CH = CH- 2-F 4-Cl OO C H 3 H -CH 2 CH = CH- 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH = CH- 2-Cl 4-Cl OSHH -CH 2 CH = CH- 2,6-F 2 4-Cl OO ──────────────────────────────────

【００９８】[0098]

【表４９】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(CH3)CH=CH- 2-Cl 4-Cl O O CH3 H -CH(CH3)CH=CH- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)CH=CH- 2-F 4-Cl O O CH3 H -CH(CH3)CH=CH- 2,6-F2 4-Cl O O CH3 H -CH2C(CH3)=CH- 2-Cl 4-Cl O O CH3 H -CH2C(CH3)=CH- 2-Cl 3,4-Cl2 O O CH3 H -CH2C(CH3)=CH- 2-F 4-Cl O O CH3 H -CH2C(CH3)=CH- 4-Cl 4-Cl O O CH2OCH3 H -CH2C(CH3)=CH- 2-Cl 4-Cl O O CH3 Br -CH2C(CH3)=CH- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH=C(CH3)- 4-F 4-Cl S O CH2CH3 H -CH2CH=C(CH3)- 2,6-F2 4-Cl O O CH3 H -CH2CH=C(CH3)- 2-Cl 4-Cl O O CH3 H -CH2CH=C(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH=C(CH3)- 4-F 4-Cl O O CH3 H -CH2CH=C(CH3)- 4-Cl 4-Cl O O CH3 H -CH2O- 2-Cl 4-Cl O O CH3 H -CH2O- 2-Cl 4-C(CH3)3 O O CH3 H -CH2O- 2-F 4-Cl O O CH3 H -CH2O- 2,6-F2 4-Cl O O CH3 H -CH(CH3)O- 2-Cl 4-Cl O O CH3 H -CH(CH3)O- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 49] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (CH 3 ) CH = CH- 2-Cl 4-Cl OO CH 3 H -CH (CH 3 ) CH = CH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 ) CH = CH- 2- F 4-Cl OO CH 3 H -CH (CH 3 ) CH = CH- 2,6-F 2 4-Cl OO CH 3 H -CH 2 C (CH 3 ) = CH- 2-Cl 4-Cl OO CH 3 H -CH 2 C (CH 3 ) = CH- 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 C (CH 3 ) = CH- 2-F 4-Cl OO CH 3 H -CH 2 C (CH 3 ) = CH- 4-Cl 4-Cl OO CH 2 OCH 3 H -CH 2 C (CH 3 ) = CH- 2-Cl 4-Cl OO CH 3 Br -CH 2 C (CH 3 ) = CH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CH = C (CH 3 )-4-F 4-Cl SO CH 2 CH 3 H -CH 2 CH = C (CH 3 ) -2,6-F 2 4-Cl OO CH 3 H -CH 2 CH = C (CH 3 )-2-Cl 4-Cl OO CH 3 H -CH 2 CH = C (CH 3 )-2-Cl 3 , 4-Cl 2 OO CH 3 H -CH 2 CH = C (CH 3 )-4-F 4-Cl OO CH 3 H -CH 2 CH = C (CH 3 )-4-Cl 4-Cl OO CH 3 H-CH 2 O- 2-Cl 4-Cl OO CH 3 H -CH 2 O- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -C H 2 O- 2-F 4-Cl OO CH 3 H -CH 2 O- 2,6-F 2 4-Cl OO CH 3 H -CH (CH 3 ) O- 2-Cl 4-Cl OO CH 3 H -CH (CH 3 ) O- 2,6-F 2 4-Cl OO ───────────────────────────────── ──

【００９９】[0099]

【表５０】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2S- 2-Cl 4-Cl O O CH3 H -CH2S- 2-Cl 4-C(CH3)3 O O CH3 H -CH2S- 2-F 4-Cl O O CH3 H -CH2S- 2,6-F2 4-Cl O O CH3 H -CH2SO- 2-Cl 4-Cl O O CH3 H -CH2SO- 2-Cl 3,4-Cl2 O O CH3 H -CH2SO- 2-F 4-Cl O O CH3 H -CH2SO- 4-Cl 4-Cl O O CH3 H -CH2SO2- 2-Cl 4-Cl O O CH3 H -CH2SO2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2SO2- 4-F 4-Cl O O CH3 H -CH2SO2- 2,6-F2 4-Cl O O CH3 H -CH2NH- 2-Cl 4-Cl O O CH3 H -CH2NH- 2-Cl 3,4-Cl2 O O CH3 H -CH2NH- 4-F 4-Cl O O CH3 H -CH2NH- 4-Cl 4-Cl O O CH3 H -CH(CH3)NH- 2-Cl 4-Cl O O CH3 H -CH(CH3)NH- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)NH- 2-F 4-Cl O O CH3 H -CH(CH3)NH- 2,6-F2 4-Cl O O CH3 H -CH2N(CH3)- 2-Cl 4-Cl O O CH3 H -CH2N(CH3)- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 50] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 S- 2- Cl 4-Cl OO CH 3 H -CH 2 S- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 S- 2-F 4-Cl OO CH 3 H -CH 2 S- 2, 6-F 2 4-Cl OO CH 3 H -CH 2 SO- 2-Cl 4-Cl OO CH 3 H -CH 2 SO- 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 SO- 2 -F 4-Cl OO CH 3 H -CH 2 SO- 4-Cl 4-Cl OO CH 3 H -CH 2 SO 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 SO 2 - 2-Cl 4 -C (CH 3) 3 OO CH 3 H -CH 2 SO 2 - 4-F 4-Cl OO CH 3 H -CH 2 SO 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 NH -2-Cl 4-Cl OO CH 3 H -CH 2 NH- 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 NH- 4-F 4-Cl OO CH 3 H -CH 2 NH-4 -Cl 4-Cl OO CH 3 H -CH (CH 3 ) NH- 2-Cl 4-Cl OO CH 3 H -CH (CH 3 ) NH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 ) NH- 2-F 4-Cl OO CH 3 H -CH (CH 3 ) NH- 2,6-F 2 4-Cl OO CH 3 H -CH 2 N (CH 3 )-2- Cl 4-Cl OO CH 3 H -CH 2 N (CH 3 )-2,6-F 2 4- Cl OO ──────────────────────────────────

【０１００】[0100]

【表５１】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2CH2O- 2-Cl 4-Cl O O CH3 H -CH2CH2O- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH2O- 2-F 4-Cl O O CH3 H -CH2CH2O- 2,6-F2 4-Cl O O CH3 H -CH2CH2O- 2-Cl 3,4-Cl2 O O CH3 Cl -CH2CH2O- 2-Cl 4-Cl O O H H -CH2CH2O- 2-F 4-Cl O O CH3 H -CH2CH2O- 4-Cl 4-Cl O S CH3 H -C(CH3)2CH2O- 2-Cl 4-Cl O O CH3 H -C(CH3)2CH2O- 2-Cl 4-C(CH3)3 O O CH3 H -C(CH3)2CH2O- 4-F 4-Cl O O CH3 H -C(CH3)2CH2O- 2,6-F2 4-Cl O O CH3 H -CH2CH2CH2O- 2-Cl 4-Cl O O CH3 H -CH2CH2CH2O- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH2CH2O- 4-F 4-Cl O O CH3 H -CH2CH2CH2O- 4-Cl 4-Cl O O CH3 H -CH2CH2S- 2-Cl 4-Cl O O CH3 H -CH2CH2S- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH2S- 2-F 4-Cl O O CH3 H -CH2CH2S- 2,6-F2 4-Cl O O H H -CH2CH2NH- 2-Cl 4-Cl O O CH3 I -CH2CH2NH- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 51] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 CH 2 O- 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 O- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CH 2 O- 2-F 4-Cl OO CH 3 H- CH 2 CH 2 O- 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH 2 O- 2-Cl 3,4-Cl 2 OO CH 3 Cl -CH 2 CH 2 O- 2-Cl 4 -Cl OOHH -CH 2 CH 2 O- 2-F 4-Cl OO CH 3 H -CH 2 CH 2 O- 4-Cl 4-Cl OS CH 3 H -C (CH 3 ) 2 CH 2 O- 2- Cl 4-Cl OO CH 3 H -C (CH 3 ) 2 CH 2 O- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -C (CH 3 ) 2 CH 2 O- 4-F 4- Cl OO CH 3 H -C (CH 3 ) 2 CH 2 O- 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 O- 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 O- 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CH 2 CH 2 O- 4-F 4-Cl OO CH 3 H -CH 2 CH 2 CH 2 O- 4- Cl 4-Cl OO CH 3 H -CH 2 CH 2 S- 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 S- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CH 2 S- 2-F 4-Cl OO CH 3 H -CH 2 CH 2 S- 2,6-F 2 4-Cl OOHH -CH 2 CH 2 NH- 2-Cl 4-Cl OO CH 3 I -CH 2 CH 2 NH- 2,6-F 2 4-Cl OO ─ ──────────────────────────────────

【０１０１】[0101]

【表５２】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2CH2NH- 2-Cl 4-Cl O O CH3 H -CH2CH2NH- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CH2NH- 2-F 4-Cl O O CH3 H -CH2CH2NH- 2,6-F2 4-Cl O O CH3 H -CH2CH2N(CH3)- 2-Cl 4-Cl O O CH3 H -CH2CH2N(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CH2CH2N(CH3)- 2-F 4-Cl O O CH3 H -CH2CH2N(CH3)- 4-Cl 4-Cl O O CH3 H -CH2OCH2- 2-Cl 4-Cl O O CH3 H -CH2OCH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2OCH2- 4-F 4-Cl O O CH3 H -CH2OCH2- 2,6-F2 4-Cl O O CH3 H -CH2SCH2- 2-Cl 4-Cl O O CH3 H -CH2SCH2- 2-Cl 3,4-Cl2 O O CH3 H -CH2SCH2- 4-F 4-Cl O O CH3 H -CH2SCH2- 4-Cl 4-Cl O O CH3 H -CH2CO- 2-Cl 4-Cl O O CH3 H -CH2CO- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CO- 2-F 4-Cl O O CH3 H -CH2CO- 2,6-F2 4-Cl O O CH3 H -CH(CH3)CO- 2-Cl 4-Cl O O CH3 H -CH(CH3)CO- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 52] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 CH 2 NH- 2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 NH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CH 2 NH- 2-F 4-Cl OO CH 3 H- CH 2 CH 2 NH- 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH 2 N (CH 3 )-2-Cl 4-Cl OO CH 3 H -CH 2 CH 2 N (CH 3 ) -2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CH 2 N (CH 3 )-2-F 4-Cl OO CH 3 H -CH 2 CH 2 N (CH 3 )-4-Cl 4 -Cl OO CH 3 H -CH 2 OCH 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 OCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 OCH 2 - 4 -F 4-Cl OO CH 3 H -CH 2 OCH 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 SCH 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 SCH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 SCH 2-4 -F 4-Cl OO CH 3 H -CH 2 SCH 2-4 -Cl 4-Cl OO CH 3 H -CH 2 CO- 2-Cl 4-Cl OO CH 3 H -CH 2 CO- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CO- 2-F 4-Cl OO CH 3 H -CH 2 CO- 2,6-F 2 4-Cl OO CH 3 H -CH (CH 3 ) CO- 2-Cl 4-Cl OO CH 3 H -CH (CH 3 ) CO-2,6-F 2 4-Cl OO ─────────── ────────────────────────

【０１０２】[0102]

【表５３】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2COCH2- 2-Cl 4-Cl O O CH3 H -CH2COCH2- 2-Cl 4-C(CH3)3 O O CH3 H -CH2COCH2- 2-F 4-Cl O O CH3 H -CH2COCH2- 2,6-F2 4-Cl O O CH3 H -CH2CO2- 2-Cl 4-Cl O O CH3 H -CH2CO2- 2-Cl 3,4-Cl2 O O CH3 H -CH2CO2- 2-F 4-Cl O O CH3 H -CH2CO2- 4-Cl 4-Cl O O CH3 H -CH(CH3)CO- 2-Cl 4-Cl O O CH3 H -CH(CH3)CO- 2-Cl 4-C(CH3)3 O O CH3 H -CH(CH3)CO- 4-F 4-Cl O O CH3 H -CH(CH3)CO- 2,6-F2 4-Cl O O CH3 H -CH2C(O)S- 2-Cl 4-Cl O O CH3 H -CH2C(O)S- 2-Cl 3,4-Cl2 O O CH3 H -CH2C(O)S- 4-F 4-Cl O O CH3 H -CH2C(O)S- 4-Cl 4-Cl O O CH3 H -CH2CONH- 2-Cl 4-Cl O O CH3 H -CH2CONH- 2-Cl 4-C(CH3)3 O O CH3 H -CH2CONH- 2-F 4-Cl O O CH3 H -CH2CONH- 2,6-F2 4-Cl O O CH3 H -CH2CH=N- 2-Cl 4-Cl O O CH3 H -CH2CH=N- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 53] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 COCH 2 - 2 -Cl 4-Cl OO CH 3 H -CH 2 COCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CH 2 COCH 2 - 2-F 4-Cl OO CH 3 H -CH 2 COCH 2 - 2,6-F 2 4- Cl OO CH 3 H -CH 2 CO 2 - 2-Cl 4-Cl OO CH 3 H -CH 2 CO 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 CO 2 - 2-F 4-Cl OO CH 3 H -CH 2 CO 2 - 4-Cl 4-Cl OO CH 3 H -CH (CH 3) CO- 2-Cl 4-Cl OO CH 3 H -CH (CH 3 ) CO- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (CH 3 ) CO- 4-F 4-Cl OO CH 3 H -CH (CH 3 ) CO-2 , 6-F 2 4-Cl OO CH 3 H -CH 2 C (O) S- 2-Cl 4-Cl OO CH 3 H -CH 2 C (O) S- 2-Cl 3,4-Cl 2 OO CH 3 H -CH 2 C (O) S- 4-F 4-Cl OO CH 3 H -CH 2 C (O) S- 4-Cl 4-Cl OO CH 3 H -CH 2 CONH- 2-Cl 4 -Cl OO CH 3 H -CH 2 CONH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 CONH- 2-F 4-Cl OO CH 3 H -CH 2 CONH- 2,6- F 2 4-Cl OO CH 3 H -CH 2 CH = N- 2-Cl 4 -Cl OO CH 3 H -CH 2 CH = N- 2,6-F 2 4-Cl OO ──────────────────────────── ───────

【０１０３】[0103]

【表５４】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH2C(CH3)=N- 2-Cl 4-Cl O O CH3 H -CH2C(CH3)=N- 2-Cl 4-C(CH3)3 O O CH3 H -CH2C(CH3)=N- 2-F 4-Cl O O CH3 H -CH2C(CH3)=N- 2,6-F2 4-Cl O O CH3 H -CO- 2-Cl 4-Cl O O CH3 H -CO- 2-Cl 3,4-Cl2 O O CH3 H -CO- 2-F 4-Cl O O CH3 H -CO- 4-Cl 4-Cl O O CH3 H -CO2- 2-Cl 4-Cl O O CH3 H -CO2- 2-Cl 4-C(CH3)3 O O CH3 H -CO2- 4-F 4-Cl O O CH3 H -CO2- 2,6-F2 4-Cl O O CH3 H -CO2CH2- 2-Cl 4-Cl O O CH3 H -CO2CH2- 2-Cl 3,4-Cl2 O O CH3 H -CO2CH2- 4-F 4-Cl O O CH3 H -CO2CH2- 4-Cl 4-Cl O O CH3 H -COCH2- 2-Cl 4-Cl O O CH3 H -COCH2- 2-Cl 4-C(CH3)3 O O CH3 H -COCH2- 2-F 4-Cl O O CH3 H -COCH2- 2,6-F2 4-Cl O O CH3 H -COCH(CH3)- 2-Cl 4-Cl O O CH3 H -COCH(CH3)- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 54] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH 2 C (CH 3 ) = N- 2-Cl 4-Cl OO CH 3 H -CH 2 C (CH 3 ) = N- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH 2 C (CH 3 ) = N -2-F 4-Cl OO CH 3 H -CH 2 C (CH 3 ) = N- 2,6-F 2 4-Cl OO CH 3 H -CO- 2-Cl 4-Cl OO CH 3 H -CO - 2-Cl 3,4-Cl 2 OO CH 3 H -CO- 2-F 4-Cl OO CH 3 H -CO- 4-Cl 4-Cl OO CH 3 H -CO 2 - 2-Cl 4-Cl OO CH 3 H -CO 2 - 2 -Cl 4-C (CH 3) 3 OO CH 3 H -CO 2 - 4-F 4-Cl OO CH 3 H -CO 2 - 2,6-F 2 4-Cl OO CH 3 H -CO 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -CO 2 CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -CO 2 CH 2 - 4-F 4- Cl OO CH 3 H -CO 2 CH 2 - 4-Cl 4-Cl OO CH 3 H -COCH 2 - 2-Cl 4-Cl OO CH 3 H -COCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -COCH 2 - 2 -F 4-Cl OO CH 3 H -COCH 2 - 2,6-F 2 4-Cl OO CH 3 H -COCH (CH 3) - 2-Cl 4-Cl OO CH 3 H -COCH (CH 3 )-2,6-F 2 4-Cl OO ── ─────────────────────────────────

【０１０４】[0104]

【表５５】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -COCH2CH2- 2-Cl 4-Cl O O CH3 H -COCH2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -COCH2CH2- 2-F 4-Cl O O CH3 H -COCH2CH2- 2,6-F2 4-Cl O O CH3 H -COCH2O- 2-Cl 4-Cl O O CH3 H -COCH2O- 2-Cl 3,4-Cl2 O O CH3 H -COCH2O- 2-F 4-Cl O O CH3 H -COCH2O- 4-Cl 4-Cl O O CH3 H -COCH=CH- 2-Cl 4-Cl O O CH3 H -COCH=CH- 2-Cl 4-C(CH3)3 O O CH3 H -COCH=CH- 4-F 4-Cl O O CH3 H -COCH=CH- 2,6-F2 4-Cl O O CH3 H -COCO2- 2-Cl 4-Cl O O CH3 H -COCO2- 2-Cl 3,4-Cl2 O O CH3 H -COCO2- 4-F 4-Cl O O CH3 H -COCO2- 4-Cl 4-Cl O O CH3 H -COCO2CH2- 2-Cl 4-Cl O O CH3 H -COCO2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -COCO2CH2- 2-F 4-Cl O O CH3 H -COCO2CH2- 2,6-F2 4-Cl O O H H -CONH- 2-Cl 4-Cl O O H H -CONH- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 55] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -COCH 2 CH 2 - 2 -Cl 4-Cl OO CH 3 H -COCH 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -COCH 2 CH 2 - 2-F 4-Cl OO CH 3 H -COCH 2 CH 2 - 2,6-F 2 4- Cl OO CH 3 H -COCH 2 O- 2-Cl 4-Cl OO CH 3 H -COCH 2 O- 2-Cl 3,4-Cl 2 OO CH 3 H -COCH 2 O- 2-F 4-Cl OO CH 3 H -COCH 2 O- 4-Cl 4-Cl OO CH 3 H -COCH = CH- 2-Cl 4-Cl OO CH 3 H -COCH = CH- 2- Cl 4-C (CH 3 ) 3 OO CH 3 H -COCH = CH- 4-F 4-Cl OO CH 3 H -COCH = CH- 2,6-F 2 4-Cl OO CH 3 H -COCO 2- 2-Cl 4-Cl OO CH 3 H -COCO 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -COCO 2 - 4-F 4-Cl OO CH 3 H -COCO 2 - 4-Cl 4- Cl OO CH 3 H -COCO 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -COCO 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -COCO 2 CH 2 - 2- F 4-Cl OO CH 3 H -COCO 2 CH 2 - 2,6-F 2 4-Cl oOHH -CONH- 2-Cl 4-Cl oOHH -CONH- 2,6-F 2 4-Cl OO ─────────────────────────────────

【０１０５】[0105]

【表５６】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CONH- 2-Cl 4-Cl O O CH3 H -CONH- 2-Cl 4-C(CH3)3 O O CH3 H -CONH- 2-F 4-Cl O O CH3 H -CONH- 2,6-F2 4-Cl O O CH3 H -CON(CH3)- 2-Cl 4-Cl O O CH3 H -CON(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CON(CH3)- 2-F 4-Cl O O CH3 H -CON(CH3)- 4-Cl 4-Cl O O CH3 H -CONHCH2- 2-Cl 4-Cl O O CH3 H -CONHCH2- 2-Cl 4-C(CH3)3 O O CH3 H -CONHCH2- 4-F 4-Cl O O CH3 H -CONHCH2- 2,6-F2 4-Cl O O CH3 H -CONHCH(CH3)- 2-Cl 4-Cl O O CH3 H -CONHCH(CH3)- 2-Cl 3,4-Cl2 O O CH3 H -CONHCH(CH3)- 4-F 4-Cl O O CH3 H -CONHCH(CH3)- 4-Cl 4-Cl O O CH3 H -CSNH- 2-Cl 4-Cl O O CH3 H -CSNH- 2-Cl 4-C(CH3)3 O O CH3 H -CSNH- 2-F 4-Cl O O CH3 H -CSNH- 2,6-F2 4-Cl O O CH3 H -CSNHCH2- 2-Cl 4-Cl O O CH3 H -CSNHCH2- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 56] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CONH- 2-Cl 4 -Cl OO CH 3 H -CONH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CONH- 2-F 4-Cl OO CH 3 H -CONH- 2,6-F 2 4-Cl OO CH 3 H -CON (CH 3 )-2-Cl 4-Cl OO CH 3 H -CON (CH 3 )-2-Cl 3,4-Cl 2 OO CH 3 H -CON (CH 3 )-2-F 4-Cl OO CH 3 H -CON (CH 3) - 4-Cl 4-Cl OO CH 3 H -CONHCH 2 - 2-Cl 4-Cl OO CH 3 H -CONHCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -CONHCH 2 - 4-F 4-Cl OO CH 3 H -CONHCH 2 - 2,6-F 2 4-Cl OO CH 3 H -CONHCH (CH 3) - 2-Cl 4- Cl OO CH 3 H -CONHCH (CH 3 )-2-Cl 3,4-Cl 2 OO CH 3 H -CONHCH (CH 3 )-4-F 4-Cl OO CH 3 H -CONHCH (CH 3 )-4 -Cl 4-Cl OO CH 3 H -CSNH- 2-Cl 4-Cl OO CH 3 H -CSNH- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CSNH- 2-F 4-Cl OO CH 3 H -CSNH- 2,6-F 2 4-Cl OO CH 3 H -CSNHCH 2 - 2-Cl 4-Cl OO CH 3 H -CSNHCH 2 - 2,6-F 2 4-Cl OO ── ─────────────────────────────────

【０１０６】[0106]

【表５７】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -O- 2-Cl 4-Cl O O CH3 H -O- 2-Cl 4-C(CH3)3 O O CH3 H -O- 2-F 4-Cl O O CH3 H -O- 2,6-F2 4-Cl O O CH3 H -S- 2-Cl 4-Cl O O CH3 H -S- 2-Cl 3,4-Cl2 O O CH3 H -S- 2-F 4-Cl O O CH3 H -S- 4-Cl 4-Cl O O CH3 H -SO- 2-Cl 4-Cl O O CH3 H -SO- 2-Cl 4-C(CH3)3 O O CH3 H -SO- 4-F 4-Cl O O CH3 H -SO- 2,6-F2 4-Cl O O CH3 H -SO2- 2-Cl 4-Cl O O CH3 H -SO2- 2-Cl 3,4-Cl2 O O CH3 H -SO2- 4-F 4-Cl O O CH3 H -SO2- 4-Cl 4-Cl O O CH3 H -NH- 2-Cl 4-Cl O O CH3 H -NH- 2-Cl 4-C(CH3)3 O O CH3 H -NH- 2-F 4-Cl O O CH3 H -NH- 2,6-F2 4-Cl O O CH3 H -N(CH2CH2CH2CH3)- 2-Cl 4-Cl O O CH3 H -N(CH2CH2CH2CH3)- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 57] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -O- 2-Cl 4 -Cl OO CH 3 H -O- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -O- 2-F 4-Cl OO CH 3 H -O- 2,6-F 2 4-Cl OO CH 3 H -S- 2-Cl 4-Cl OO CH 3 H -S- 2-Cl 3,4-Cl 2 OO CH 3 H -S- 2-F 4-Cl OO CH 3 H -S- 4- Cl 4-Cl OO CH 3 H -SO- 2-Cl 4-Cl OO CH 3 H -SO- 2-Cl 4-C (CH 3 ) 3 OO CH 3 H -SO- 4-F 4-Cl OO CH 3 H -SO- 2,6-F 2 4 -Cl OO CH 3 H -SO 2 - 2-Cl 4-Cl OO CH 3 H -SO 2 - 2-Cl 3,4-Cl 2 OO CH 3 H - SO 2-4 -F 4-Cl OO CH 3 H -SO 2-4 -Cl 4-Cl OO CH 3 H -NH- 2-Cl 4-Cl OO CH 3 H -NH- 2-Cl 4-C ( CH 3 ) 3 OO CH 3 H -NH- 2-F 4-Cl OO CH 3 H -NH- 2,6-F 2 4-Cl OO CH 3 H -N (CH 2 CH 2 CH 2 CH 3 )- 2-Cl 4-Cl OO CH 3 H -N (CH 2 CH 2 CH 2 CH 3 )-2,6-F 2 4-Cl OO ────────────────── ────────────── ──

【０１０７】[0107]

【表５８】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -N(CH3)- 2-Cl 4-Cl O O CH3 H -N(CH3)- 2-Cl 4-C(CH3)3 O O CH3 H -N(CH3)- 2-F 4-Cl O O CH3 H -N(CH3)- 2,6-F2 4-Cl O O CH3 H -N(CH2CH=CH2)- 2-Cl 4-Cl O O CH3 H -N(CH2CH=CH2)- 2-Cl 3,4-Cl2 O O CH3 H -N(CH2CH=CH2)- 2-F 4-Cl O O CH3 H -N(CH2CH=CH2)- 4-Cl 4-Cl O O CH3 H -N(CH2C6H5)- 2-Cl 4-Cl O O CH3 H -N(CH2C6H5)- 2-Cl 4-C(CH3)3 O O CH3 H -N(CH2C6H5)- 4-F 4-Cl O O CH3 H -N(CH2C6H5)- 2,6-F2 4-Cl O O CH3 H -N(COCH3)- 2-Cl 4-Cl O O CH3 H -N(COCH3)- 2-Cl 3,4-Cl2 O O CH3 H -N(COCH3)- 4-F 4-Cl O O CH3 H -N(COCH3)- 4-Cl 4-Cl O O CH3 H -OCH2- 2-Cl 4-Cl O O CH3 H -OCH2- 2-Cl 4-C(CH3)3 O O CH3 H -OCH2- 2-F 4-Cl O O CH3 H -OCH2- 2,6-F2 4-Cl O O CH3 H -OCH2CH2- 2-Cl 4-Cl O O CH3 H -OCH2CH2- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 58] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -N (CH 3 )- 2-Cl 4-Cl OO CH 3 H -N (CH 3 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -N (CH 3 )-2-F 4-Cl OO CH 3 H- N (CH 3 )-2,6-F 2 4-Cl OO CH 3 H -N (CH 2 CH = CH 2 )-2-Cl 4-Cl OO CH 3 H -N (CH 2 CH = CH 2 ) -2-Cl 3,4-Cl 2 OO CH 3 H -N (CH 2 CH = CH 2 )-2-F 4-Cl OO CH 3 H -N (CH 2 CH = CH 2 )-4-Cl 4 -Cl OO CH 3 H -N (CH 2 C 6 H 5 )-2-Cl 4-Cl OO CH 3 H -N (CH 2 C 6 H 5 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -N (CH 2 C 6 H 5 )-4-F 4-Cl OO CH 3 H -N (CH 2 C 6 H 5 )-2,6-F 2 4-Cl OO CH 3 H -N (COCH 3 )-2-Cl 4-Cl OO CH 3 H -N (COCH 3 )-2-Cl 3,4-Cl 2 OO CH 3 H -N (COCH 3 )-4-F 4-Cl OO CH 3 H -N (COCH 3) - 4-Cl 4-Cl OO CH 3 H -OCH 2 - 2-Cl 4-Cl OO CH 3 H -OCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -OCH 2 - 2-F 4-Cl OO CH 3 H -OCH 2 - 2,6-F 2 4-Cl OO CH 3 H -O CH 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -OCH 2 CH 2 - 2,6-F 2 4-Cl OO ─────────────────── ───────────────

【０１０８】[0108]

【表５９】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -SCH2- 2-Cl 4-Cl O O CH3 H -SCH2- 2-Cl 4-C(CH3)3 O O CH3 H -SCH2- 2-F 4-Cl O O CH3 H -SCH2- 2,6-F2 4-Cl O O CH3 H -SO2CH2- 2-Cl 4-Cl O O CH3 H -SO2CH2- 2-Cl 3,4-Cl2 O O CH3 H -SO2CH2- 2-F 4-Cl O O CH3 H -SO2CH2- 4-Cl 4-Cl O O CH3 H -SCH2CH2- 2-Cl 4-Cl O O CH3 H -SCH2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -SCH2CH2- 4-F 4-Cl O O CH3 H -SCH2CH2- 2,6-F2 4-Cl O O CH3 H -NHCH2- 2-Cl 4-Cl O O CH3 H -NHCH2- 2-Cl 3,4-Cl2 O O CH3 H -NHCH2- 4-F 4-Cl O O CH3 H -NHCH2- 4-Cl 4-Cl O O CH3 H -N(CH3)CH2- 2-Cl 4-Cl O O CH3 H -N(CH3)CH2- 2-Cl 4-C(CH3)3 O O CH3 H -N(CH3)CH2- 2-F 4-Cl O O CH3 H -N(CH3)CH2- 2,6-F2 4-Cl O O CH3 H -NHCH(CH3)- 2-Cl 4-Cl O O CH3 H -NHCH(CH3)- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 59] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -SCH 2 - 2-Cl 4-Cl OO CH 3 H -SCH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -SCH 2 - 2-F 4-Cl OO CH 3 H -SCH 2 - 2,6-F 2 4-Cl OO CH 3 H -SO 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -SO 2 CH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -SO 2 CH 2 - 2- F 4-Cl OO CH 3 H -SO 2 CH 2 - 4-Cl 4-Cl OO CH 3 H -SCH 2 CH 2 - 2-Cl 4-Cl OO CH 3 H -SCH 2 CH 2 - 2-Cl 4 -C (CH 3) 3 OO CH 3 H -SCH 2 CH 2 - 4-F 4-Cl OO CH 3 H -SCH 2 CH 2 - 2,6-F 2 4-Cl OO CH 3 H -NHCH 2 - 2-Cl 4-Cl OO CH 3 H -NHCH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -NHCH 2 - 4-F 4-Cl OO CH 3 H -NHCH 2 - 4-Cl 4- Cl OO CH 3 H -N (CH 3) CH 2 - 2-Cl 4-Cl OO CH 3 H -N (CH 3) CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -N (CH 3) CH 2 - 2 -F 4-Cl OO CH 3 H -N (CH 3) CH 2 - 2,6-F 2 4-Cl OO CH 3 H -NHCH (CH 3) - 2-Cl 4 -Cl OO CH 3 H -NHC H (CH 3 )-2,6-F 2 4-Cl OO ───────────────────────────────────

【０１０９】[0109]

【表６０】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -NHCH2CH2- 2-Cl 4-Cl O O CH3 H -NHCH2CH2- 2-Cl 4-C(CH3)3 O O CH3 H -NHCH2CH2- 2-F 4-Cl O O CH3 H -NHCH2CH2- 2,6-F2 4-Cl O O CH3 H -N=CH- 2-Cl 4-Cl O O CH3 H -N=CH- 2-Cl 3,4-Cl2 O O CH3 H -N=CH- 2-F 4-Cl O O CH3 H -N=CH- 4-Cl 4-Cl O O CH3 H -N=C(CH3)- 2-Cl 4-Cl O O CH3 H -N=C(CH3)- 2-Cl 4-C(CH3)3 O O CH3 H -N=C(CH3)- 4-F 4-Cl O O CH3 H -N=C(CH3)- 2,6-F2 4-Cl O O CH3 H -N=CHCH2- 2-Cl 4-Cl O O CH3 H -N=CHCH2- 2-Cl 3,4-Cl2 O O CH3 H -N=CHCH2- 4-F 4-Cl O O CH3 H -N=CHCH2- 4-Cl 4-Cl O O CH3 H -N=C(CH3)CH2- 2-Cl 4-Cl O O CH3 H -N=C(CH3)CH2- 2-Cl 4-C(CH3)3 O O CH3 H -N=C(CH3)CH2- 2-F 4-Cl O O CH3 H -N=C(CH3)CH2- 2,6-F2 4-Cl O O CH3 H -CH2CH(OH)- 2-Cl 4-Cl O O CH3 H -CH2CH(OH)- 2,6-F2 4-Cl O O ──────────────────────────────────[Table 60] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -NHCH 2 CH 2 - 2 -Cl 4-Cl OO CH 3 H -NHCH 2 CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -NHCH 2 CH 2 - 2-F 4-Cl OO CH 3 H -NHCH 2 CH 2 - 2,6-F 2 4- Cl OO CH 3 H -N = CH- 2-Cl 4-Cl OO CH 3 H -N = CH- 2-Cl 3,4-Cl 2 OO CH 3 H -N = CH- 2-F 4-Cl OO CH 3 H -N = CH- 4-Cl 4-Cl OO CH 3 H -N = C (CH 3 )-2-Cl 4-Cl OO CH 3 H -N = C (CH 3 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -N = C (CH 3 )-4-F 4-Cl OO CH 3 H -N = C (CH 3 )-2 , 6-F 2 4-Cl OO CH 3 H -N = CHCH 2 - 2-Cl 4-Cl OO CH 3 H -N = CHCH 2 - 2-Cl 3,4-Cl 2 OO CH 3 H -N = CHCH 2 - 4-F 4- Cl OO CH 3 H -N = CHCH 2 - 4-Cl 4-Cl OO CH 3 H -N = C (CH 3) CH 2 - 2-Cl 4-Cl OO CH 3 H -N = C (CH 3) CH 2 - 2-Cl 4-C (CH 3) 3 OO CH 3 H -N = C (CH 3) CH 2 - 2-F 4-Cl OO CH 3 H -N = C (CH 3) CH 2 - 2,6-F 2 4-Cl OO CH 3 H -CH 2 CH (OH) - 2-Cl 4-Cl OO CH 3 H -CH 2 CH (OH)-2,6-F 2 4-Cl OO ────────────────────────────── ─────

【０１１０】[0110]

【表６１】 第 １ 表 （ 続 ） ────────────────────────────────── R1 R2 A Xl Ym Z1 Z2 ────────────────────────────────── CH3 H -CH(C6H5)- 2-Cl 4-Cl O O CH3 H -CH(C6H5)- 2-Cl 4-C(CH3)3 O O CH3 H -CH(C6H5)- 2-F 4-Cl O O CH3 H -CH(C6H5)- 2,6-F2 4-Cl O O CH3 H -CH(CN)- 2-Cl 4-Cl O O CH3 H -CH(CN)- 2-Cl 3,4-Cl2 O O CH3 H -CH(CN)- 2-F 4-Cl O O CH3 H -CH(CN)- 4-Cl 4-Cl O O ──────────────────────────────────[Table 61] Table 1 (continued) ────────────────────────────────── R 1 R 2 AX l Y m Z 1 Z 2 ────────────────────────────────── CH 3 H -CH (C 6 H 5 )-2-Cl 4-Cl OO CH 3 H -CH (C 6 H 5 )-2-Cl 4-C (CH 3 ) 3 OO CH 3 H -CH (C 6 H 5 )-2-F 4- Cl OO CH 3 H -CH (C 6 H 5 )-2,6-F 2 4-Cl OO CH 3 H -CH (CN)-2-Cl 4-Cl OO CH 3 H -CH (CN)-2 -Cl 3,4-Cl 2 OO CH 3 H -CH (CN)-2-F 4-Cl OO CH 3 H -CH (CN)-4-Cl 4-Cl OO ────────── ─────────────────────────

【０１１１】第 ２ 表Table 2

【０１１２】[0112]

【化２７】 [Chemical 27]

【０１１３】[0113]

【表６２】 ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q1 O O CH3 H -CH2- 2-Cl Q2 O O CH3 H -CH2- 2-Cl Q3 O O CH3 H -CH2- 2-Cl Q4 O O CH3 H -CH2- 2-Cl Q5 O O CH3 H -CH2- 2-Cl Q6 O O CH3 H -CH2- 2-Cl Q7 O O CH3 H -CH2- 2-Cl Q8 O O CH3 H -CH2- 2-Cl Q9 O O CH3 H -CH2- 2-Cl Q10 O O CH3 H -CH2- 2-Cl Q11 O O CH3 H -CH2- 2-Cl Q12 O O CH3 H -CH2- 2-Cl Q13 O O CH3 H -CH2- 2-Cl Q14 O O CH3 H -CH2- 2-Cl Q15 O O CH3 H -CH2- 2-Cl Q16 O O CH3 H -CH2- 2-Cl Q17 O O CH3 H -CH2- 2-Cl Q18 O O CH3 H -CH2- 2-Cl Q19 O O CH3 H -CH2- 2-Cl Q20 O O CH3 H -CH2- 2-Cl Q21 O O CH3 H -CH2- 2-Cl Q22 O O CH3 H -CH2- 2-Cl Q23 O O ──────────────────────────────────[Table 62] ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─ ────────────────────────────────── CH 3 H -CH 2 - 2 -Cl Q1 OO CH 3 H - CH 2 - 2-Cl Q2 OO CH 3 H -CH 2 - 2-Cl Q3 OO CH 3 H -CH 2 - 2-Cl Q4 OO CH 3 H -CH 2 - 2-Cl Q5 OO CH 3 H -CH 2 - 2-Cl Q6 OO CH 3 H -CH 2 - 2-Cl Q7 OO CH 3 H -CH 2 - 2-Cl Q8 OO CH 3 H -CH 2 - 2-Cl Q9 OO CH 3 H -CH 2 - 2 -Cl Q10 OO CH 3 H -CH 2 - 2-Cl Q11 OO CH 3 H -CH 2 - 2-Cl Q12 OO CH 3 H -CH 2 - 2-Cl Q13 OO CH 3 H -CH 2 - 2-Cl Q14 OO CH 3 H -CH 2 - 2-Cl Q15 OO CH 3 H -CH 2 - 2-Cl Q16 OO CH 3 H -CH 2 - 2-Cl Q17 OO CH 3 H -CH 2 - 2-Cl Q18 OO CH 3 H -CH 2 - 2- Cl Q19 OO CH 3 H -CH 2 - 2-Cl Q20 OO CH 3 H -CH 2 - 2-Cl Q21 OO CH 3 H -CH 2 - 2-Cl Q22 OO CH 3 H -CH 2 - 2-Cl Q23 OO ──────────────────────────────────

【０１１４】[0114]

【表６３】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q24 O O CH3 H -CH2- 2-Cl Q25 O O CH3 H -CH2- 2-Cl Q26 O O CH3 H -CH2- 2-Cl Q27 O O CH3 H -CH2- 2-Cl Q28 O O CH3 H -CH2- 2-Cl Q29 O O CH3 H -CH2- 2-Cl Q30 O O CH3 H -CH2- 2-Cl Q31 O O CH3 H -CH2- 2-Cl Q32 O O CH3 H -CH2- 2-Cl Q33 O O CH3 H -CH2- 2-Cl Q34 O O CH3 H -CH2- 2-Cl Q35 O O CH3 H -CH2- 2-Cl Q36 O O CH3 H -CH2- 2-Cl Q37 O O CH3 H -CH2- 2-Cl Q38 O O CH3 H -CH2- 2-Cl Q39 O O CH3 H -CH2- 2-Cl Q40 O O CH3 H -CH2- 2-Cl Q41 O O CH3 H -CH2- 2-Cl Q42 O O CH3 H -CH2- 2-Cl Q43 O O CH3 H -CH2- 2-Cl Q44 O O CH3 H -CH2- 2-Cl Q45 O O ───────────────────────────────────[Table 63] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2-Cl Q24 OO CH 3 H -CH 2 - 2-Cl Q25 OO CH 3 H -CH 2 - 2-Cl Q26 OO CH 3 H -CH 2 - 2-Cl Q27 OO CH 3 H -CH 2 - 2-Cl Q28 OO CH 3 H -CH 2 - 2- Cl Q29 OO CH 3 H -CH 2 - 2-Cl Q30 OO CH 3 H -CH 2 - 2-Cl Q31 OO CH 3 H -CH 2 - 2-Cl Q32 OO CH 3 H -CH 2 - 2-Cl Q33 OO CH 3 H -CH 2 - 2-Cl Q34 OO CH 3 H -CH 2 - 2-Cl Q35 OO CH 3 H -CH 2 - 2-Cl Q36 OO CH 3 H - CH 2 - 2-Cl Q37 OO CH 3 H -CH 2 - 2-Cl Q38 OO CH 3 H -CH 2 - 2-Cl Q39 OO CH 3 H -CH 2 - 2-Cl Q40 OO CH 3 H -CH 2 - 2-Cl Q41 OO CH 3 H -CH 2 - 2-Cl Q42 OO CH 3 H -CH 2 - 2-Cl Q43 OO CH 3 H -CH 2 - 2-Cl Q44 OO CH 3 H -CH 2 - 2 -Cl Q45 OO ────────────────────────────────────

【０１１５】[0115]

【表６４】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q46 O O CH3 H -CH2- 2-Cl Q47 O O CH3 H -CH2- 2-Cl Q48 O O CH3 H -CH2- 2-Cl Q49 O O CH3 H -CH2- 2-Cl Q50 O O CH3 H -CH2- 2-Cl Q55 O O CH3 H -CH2- 2-Cl Q56 O O CH3 H -CH2- 2-Cl Q57 O O CH3 H -CH2- 2-Cl Q58 O O CH3 H -CH2- 2-Cl Q59 O O CH3 H -CH2- 2-Cl Q60 O O CH3 H -CH2- 2-Cl Q61 O O CH3 H -CH2- 2-Cl Q6-5-CF3 O O CH3 H -CH(CH3)- 2-Cl Q6-5-CF3 O O CH3 H -CH2- 2-Cl Q6-4-CH3-5-C6H5 O O CH3 H -C(CH3)2- 2-Cl Q6-4-CH3-5-C6H5 O O CH3 H -CH2- 2-Cl Q7-5-Cl O O CH3 H -CH(CH3)- 2-Cl Q7-5-Cl O O CH3 H -CH2- 2-Cl Q17-5-C6H5 O O CH3 H -C(CH3)2- 2-Cl Q17-5-C6H5 O O CH3 H -CH2- 2-Cl Q9-1-C6H5 O O CH3 H -CH(CH3)- 2-Cl Q9-1-C6H5 O O ───────────────────────────────────[Table 64] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2-Cl Q46 OO CH 3 H -CH 2 - 2-Cl Q47 OO CH 3 H -CH 2 - 2-Cl Q48 OO CH 3 H -CH 2 - 2-Cl Q49 OO CH 3 H -CH 2 - 2-Cl Q50 OO CH 3 H -CH 2 - 2- Cl Q55 OO CH 3 H -CH 2 - 2-Cl Q56 OO CH 3 H -CH 2 - 2-Cl Q57 OO CH 3 H -CH 2 - 2-Cl Q58 OO CH 3 H -CH 2 - 2-Cl Q59 OO CH 3 H -CH 2 - 2-Cl Q60 OO CH 3 H -CH 2 - 2-Cl Q61 OO CH 3 H -CH 2 - 2-Cl Q6-5-CF 3 OO CH 3 H -CH (CH 3 ) - 2-Cl Q6-5-CF 3 OO CH 3 H -CH 2 - 2-Cl Q6-4-CH 3 -5-C 6 H 5 OO CH 3 H -C (CH 3) 2 - 2- Cl Q6-4-CH 3 -5-C 6 H 5 OO CH 3 H -CH 2 - 2-Cl Q7-5-Cl OO CH 3 H -CH (CH 3) - 2 -Cl Q7-5-Cl OO CH 3 H -CH 2 - 2-Cl Q17-5-C 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl Q17-5-C 6 H 5 OO CH 3 H -CH 2 - 2- Cl Q9-1-C 6 H 5 OO CH 3 H -CH (CH 3) - 2-Cl Q9-1-C 6 H 5 OO ───── ─────────────────────────────

【０１１６】[0116]

【表６５】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q20-4-CF3 O O CH3 H -C(CH3)2- 2-Cl Q20-4-CF3 O O CH3 H -CH2- 2-Cl Q37-5-Cl O O CH3 H -CH(CH3)- 2-Cl Q37-5-Cl O O CH3 H -C(CH3)2- 2-Cl Q37-5-Cl O O CH3 H -CH2- 2,6-F2 Q37-5-Cl O O CH3 H -CH2- 2-Cl Q37-5-CH3 O O CH3 H -CH(CH3)- 2-Cl Q37-5-CH3 O O CH3 H -CH2- 2-Cl Q37-5-OCF3 O O CH3 H -C(CH3)2- 2-Cl Q37-5-OCF3 O O CH3 H -CH2- 2-Cl Q37-5-SCF3 O O CH3 H -CH(CH3)- 2-Cl Q37-5-SCF3 O O CH3 H -CH2- 2-Cl Q38-5-Cl O O CH3 H -CH(CH3)- 2-Cl Q38-5-Cl O O CH3 H -C(CH3)2- 2-Cl Q38-5-Cl O O CH3 H -CH2- 2,6-F2 Q38-5-Cl O O CH3 H -CH2- 2-Cl Q38-5-Br O O CH3 H -CH(CH3)- 2-Cl Q38-5-Br O O CH3 H -CH2- 2-Cl Q38-5-CF3 O O CH3 H -C(CH3)2- 2-Cl Q38-5-CF3 O O CH3 H -CH2- 2-Cl Q38-5-CO2CH3 O O CH3 H -CH(CH3)- 2-Cl Q38-5-CO2CH3 O O ───────────────────────────────────[Table 65] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2-Cl Q20-4-CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl Q20-4-CF 3 OO CH 3 H -CH 2 - 2-Cl Q37-5-Cl OO CH 3 H -CH ( CH 3) - 2-Cl Q37-5 -Cl OO CH 3 H -C (CH 3) 2 - 2-Cl Q37-5-Cl OO CH 3 H -CH 2 - 2,6-F 2 Q37-5- Cl OO CH 3 H -CH 2 - 2-Cl Q37-5-CH 3 OO CH 3 H -CH (CH 3) - 2-Cl Q37-5-CH 3 OO CH 3 H -CH 2 - 2-Cl Q37 -5-OCF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl Q37-5-OCF 3 OO CH 3 H -CH 2 - 2-Cl Q37-5-SCF 3 OO CH 3 H -CH ( CH 3) - 2-Cl Q37-5 -SCF 3 OO CH 3 H -CH 2 - 2-Cl Q38-5-Cl OO CH 3 H -CH (CH 3) - 2-Cl Q38-5-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl Q38-5-Cl OO CH 3 H -CH 2 - 2,6-F 2 Q38-5-Cl OO CH 3 H -CH 2 - 2-Cl Q38- 5-Br OO CH 3 H -CH (CH 3) - 2-Cl Q38-5-Br OO CH 3 H -CH 2 - 2-Cl Q38-5-CF 3 OO CH 3 H -C (CH 3) 2 -2-Cl Q38-5-CF 3 OO CH 3 H -CH 2 - 2-Cl Q38-5- CO 2 CH 3 OO CH 3 H -CH (CH 3) - 2-Cl Q38-5-CO 2 CH 3 OO ──────────── ───────────────────────

【０１１７】[0117]

【表６６】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q39-6-SCF3 O O CH3 H -C(CH3)2- 2-Cl Q39-6-SCF3 O O CH3 H -CH2- 2-Cl Q39-6-SCF3 S O CH3 H -CH(CH3)- 2-Cl Q39-6-SCF3 S O CH3 H -C(CH3)2- 2-Cl Q39-6-SO2CF3 O O CH3 H -CH2- 2,6-F2 Q39-6-SO2CF3 O O CH3 H -CH2- 2-Cl Q39-2,6-Cl2 O O CH3 H -CH(CH3)- 2-Cl Q39-2,6-Cl2 O O CH3 H -CH2- 2,6-F2 Q39-2,6-Cl2 O O CH3 H -C(CH3)2- 2-Cl Q39-2,6-Cl2 O O CH3 H -CH2- 2-Cl Q39-4,6-Cl2 O O CH3 H -CH(CH3)- 2-Cl Q39-4,6-Cl2 O O CH3 H -CH2- 2-Cl Q39-6-OC6H5 O O CH3 H -CH(CH3)- 2-Cl Q39-6-OC6H5 O O CH3 H -C(CH3)2- 2-Cl Q46-5-C6H5-6-CH3 O O CH3 H -CH2- 2,6-F2 Q46-5-C6H5-6-CH3 O O CH3 H -CH2- 2-Cl Q59-2-CF3 O O CH3 H -CH(CH3)- 2-Cl Q59-2-CF3 O O CH3 H -CH2- 2-Cl Q60-2-CF3 O O CH3 H -C(CH3)2- 2-Cl Q60-2-CF3 O O CH3 H -CH2- 2-Cl Q61-6-CF3 O O CH3 H -CH(CH3)- 2-Cl Q61-6-CF3 O O ───────────────────────────────────[Table 66] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2-Cl Q39-6-SCF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl Q39-6-SCF 3 OO CH 3 H -CH 2 - 2-Cl Q39-6-SCF 3 SO CH 3 H -CH (CH 3) - 2-Cl Q39-6-SCF 3 SO CH 3 H -C (CH 3) 2 - 2-Cl Q39-6-SO 2 CF 3 OO CH 3 H -CH 2 - 2,6-F 2 Q39-6-SO 2 CF 3 OO CH 3 H -CH 2 - 2-Cl Q39-2,6-Cl 2 OO CH 3 H -CH (CH 3) - 2-Cl Q39-2,6-Cl 2 OO CH 3 H -CH 2 - 2,6 -F 2 Q39-2,6-Cl 2 OO CH 3 H -C (CH 3) 2 - 2-Cl Q39-2,6-Cl 2 OO CH 3 H - CH 2 - 2-Cl Q39-4,6- Cl 2 OO CH 3 H -CH (CH 3) - 2-Cl Q39-4,6-Cl 2 OO CH 3 H -CH 2 - 2-Cl Q39-6 -OC 6 H 5 OO CH 3 H -CH (CH 3) - 2-Cl Q39-6-OC 6 H 5 OO CH 3 H -C (CH 3) 2 - 2-Cl Q46-5-C 6 H 5 -6-CH 3 OO CH 3 H -CH 2 - 2,6-F 2 Q46-5-C 6 H 5 -6-CH 3 OO CH 3 H -CH 2 - 2-Cl Q59-2-CF 3 OO CH 3 H -CH (CH 3 )-2-Cl Q59-2-CF 3 OO CH 3 H -CH 2 - 2-Cl Q60-2 -CF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl Q60-2-CF 3 OO CH 3 H -CH 2 - 2-Cl Q61-6- CF 3 OO CH 3 H -CH (CH 3 )-2-Cl Q61-6-CF 3 OO ──────────────────────────── ────────

【０１１８】[0118]

【表６７】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── CH3 H -CH2- 2-Cl Q61-6-Cl O O CH3 H -C(CH3)2- 2-Cl Q61-6-Cl O O CH3 H -CH2- 2-Cl Q61-6-OCF3 O O CH3 H -CH(CH3)- 2-Cl Q61-6-OCF3 O O CH3 H -C(CH3)2- 2-Cl Q61-6-OCF3 O O CH3 H -CH2- 2,6-F2 Q61-6-OCF3 O O CH3 H -CH2- 2-Cl Q61-6-OC6H5 O O CH3 H -CH(CH3)- 2-Cl Q61-6-OC6H5 O O CH3 H -CH2- 2-F Q39-6-Cl O O CH3 H -CH2- 2-Cl Q39-6-Cl O O CH3 H -CH2- 2,6-F2 Q39-6-Cl O O CH3 H -CH2- 4-F Q39-6-Cl O O CH3 H -CH2- 4-Cl Q39-6-Cl O O CH3 H -CH2- 2-Cl-6-F Q39-6-Cl O O CH3 H -CH2- 2-Br Q39-6-Cl O O CH3 H -CH2- 4-Br Q39-6-Cl O O CH3 H -CH2- 2-CF3 Q39-6-Cl O O CH3 H -CH2- 3,4-Cl2 Q39-6-Cl O O CH3 H -CH(CH3)- 2-Cl Q39-6-Cl O O CH3 H -C(CH3)2- 2-Cl Q39-6-Cl O O ───────────────────────────────────[Table 67] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── CH 3 H -CH 2 - 2-Cl Q61-6-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl Q61-6-Cl OO CH 3 H -CH 2 - 2-Cl Q61-6-OCF 3 OO CH 3 H -CH (CH 3) - 2-Cl Q61-6- OCF 3 OO CH 3 H -C (CH 3) 2 - 2-Cl Q61-6-OCF 3 OO CH 3 H -CH 2 - 2,6-F 2 Q61-6 -OCF 3 OO CH 3 H -CH 2 - 2-Cl Q61-6-OC 6 H 5 OO CH 3 H -CH (CH 3) - 2-Cl Q61-6-OC 6 H 5 OO CH 3 H -CH 2 - 2-F Q39-6-Cl OO CH 3 H -CH 2 - 2-Cl Q39-6-Cl OO CH 3 H -CH 2 - 2,6-F 2 Q39-6-Cl OO CH 3 H - CH 2 - 4-F Q39-6- Cl OO CH 3 H -CH 2 - 4-Cl Q39-6-Cl OO CH 3 H -CH 2 - 2-Cl-6-F Q39-6-Cl OO CH 3 H -CH 2 - 2-Br Q39-6 -Cl OO CH 3 H -CH 2 - 4-Br Q39-6-Cl OO CH 3 H -CH 2 - 2-CF 3 Q39-6-Cl OO CH 3 H -CH 2 - 3,4-Cl 2 Q39-6 -Cl OO CH 3 H -CH (CH 3) - 2-Cl Q39-6-Cl OO CH 3 H -C (CH 3) 2 - 2-Cl Q39 -6-Cl OO ────── ─────────────────────────────

【０１１９】[0119]

【表６８】 第 ２ 表 （ 続 ） ─────────────────────────────────── R1 R2 A Xl B Z1 Z2 ─────────────────────────────────── H H -CH2- 2-Cl Q39-6-Cl O O CH2CH3 H -CH2- 2-Cl Q39-6-Cl O O CH2CH=CH2 H -CH2- 2-Cl Q39-6-Cl O O CH2OCH3 H -CH2- 2-Cl Q39-6-Cl O O CH2C6H5 H -CH2- 2-Cl Q39-6-Cl O O NH2 H -CH2- 2-Cl Q39-6-Cl O O CH3 Cl -CH2- 2-Cl Q39-6-Cl O O CH3 Br -CH2- 2,6-F2 Q39-6-Cl O O CH3 I -CH2- 2-Cl Q39-6-Cl O O CH3 CH3 -CH2- 2-Cl Q39-6-Cl O O CH3 CH2CH3 -CH2- 2-F Q39-6-Cl O O CH3 CN -CH2- 2-Cl Q39-6-Cl O O CH3 NO2 -CH2- 2,6-F2 Q39-6-Cl O O CH3 H -CH2- 4-F Q39-6-Cl S O CH3 H -CH2- 4-Cl Q39-6-Cl O S CH3 H -CH2- 2-Cl-6-F Q39-6-Cl S S CH3 H -CH2- 2-Br Q39-6-Cl NH O CH3 H -CH2- 4-Br Q39-6-Cl O NH ────────────────────────────────── 本発明化合物を有害生物防除剤として使用するに当た
っては、一般には適当な担体、例えばクレー、タルク、
ベントナイト、珪藻土等の固体担体或いは水、メタノー
ル、エタノール等のアルコール類、ベンゼン、トルエ
ン、キシレン等の芳香族炭化水素類、塩素化炭化水素
類、エーテル類、ケトン類、酢酸エチル等のエステル
類、ジメチルホルムアミド等の酸アミド類の液体担体と
混用して適用することができ、所望により乳化剤、分散
剤、懸濁剤、浸透剤、展着剤、安定剤等を添加し、乳
剤、油剤、水和剤、粉剤、粒剤、フロアブル剤等任意の
剤型として実用に供することができる。[Table 68] Table 2 (continued) ─────────────────────────────────── R 1 R 2 AX l BZ 1 Z 2 ─────────────────────────────────── HH -CH 2 - 2-Cl Q39- 6-Cl OO CH 2 CH 3 H -CH 2 - 2-Cl Q39-6-Cl OO CH 2 CH = CH 2 H -CH 2 - 2-Cl Q39-6-Cl OO CH 2 OCH 3 H -CH 2 - 2-Cl Q39-6-Cl OO CH 2 C 6 H 5 H -CH 2 - 2-Cl Q39-6-Cl OO NH 2 H -CH 2 - 2-Cl Q39-6-Cl OO CH 3 Cl - CH 2 - 2-Cl Q39-6- Cl OO CH 3 Br -CH 2 - 2,6-F 2 Q39-6-Cl OO CH 3 I -CH 2 - 2-Cl Q39-6-Cl OO CH 3 CH 3 -CH 2 - 2-Cl Q39-6 -Cl OO CH 3 CH 2 CH 3 -CH 2 - 2-F Q39-6-Cl OO CH 3 CN -CH 2 - 2-Cl Q39-6-Cl OO CH 3 NO 2 -CH 2 - 2,6- F 2 Q39-6-Cl OO CH 3 H -CH 2 - 4-F Q39-6-Cl SO CH 3 H -CH 2 - 4-Cl Q39-6-Cl OS CH 3 H -CH 2 - 2 -Cl-6-F Q39-6-Cl SS CH 3 H -CH 2 - 2-Br Q39-6-Cl NH O CH 3 H -CH 2 - 4-Br Q39- 6-Cl 2 O NH ──────────────────────────────── ─ When compound of the present invention is used as pesticides are generally suitable for carriers, such as clay, talc,
Bentonite, solid carriers such as diatomaceous earth or water, alcohols such as methanol, ethanol, benzene, toluene, aromatic hydrocarbons such as xylene, chlorinated hydrocarbons, ethers, ketones, esters such as ethyl acetate, It can be applied by mixing with a liquid carrier of acid amides such as dimethylformamide. If desired, an emulsifier, a dispersant, a suspending agent, a penetrant, a spreading agent, a stabilizer, etc. are added, and an emulsion, an oil agent, a water agent are added. It can be put into practical use as an arbitrary dosage form such as a hydrating agent, a powder agent, a granule agent, and a flowable agent.

【０１２０】又、必要に応じて製剤時又は散布時に他種
の除草剤、各種殺虫剤、殺菌剤、植物生長調節剤、共力
剤等と混合施用してもよい。本発明化合物の施用薬量は
適用場面、施用時期、施用方法、対象病害虫、栽培作物
等により差異はあるが、一般には有効成分量としてヘク
タール当たり、0.005 〜50kg程度が適当である。Further, if necessary, it may be mixed with other kinds of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of formulation or spraying. The application dose of the compound of the present invention varies depending on the application scene, application time, application method, target pests, cultivated crops, etc., but in general, about 0.005 to 50 kg per hectare of the active ingredient is suitable.

【０１２１】次に、本発明の各種製剤の配合割合及び種
類を第３表に記載する。Next, Table 3 shows the compounding ratios and types of various preparations of the present invention.

【０１２２】第 ３ 表Table 3

【表６９】 ────────────────────────────────── 有効成分 担 体 界面活性剤 他の成分(補助剤) ────────────────────────────────── 乳 剤 1〜25 52〜95 3〜20 0〜20 油 剤 1〜30 57〜99 フロアブル剤 1〜70 10〜90 1〜20 0〜10 水 和 剤 1〜70 15〜93 3〜10 0〜5 粉 剤 0.01〜30 67〜99.5 0〜3 粒 剤 0.01〜30 67〜99.5 0〜8 ───────────────────────────────── 上記の表中の数値は、重量％を示す。[Table 69] ────────────────────────────────── Active ingredient Carrier Surfactant Other ingredients (auxiliary) Agent) ────────────────────────────────── Emulsion 1-25 52-95 3-20 0-20 Oil agent 1 to 30 57 to 99 Flowable agent 1 to 70 10 to 90 1 to 200 0 to 10 Hydrate agent 1 to 70 15 to 93 3 to 10 0 to 5 Powder agent 0.01 to 30 67 to 99.5 0 to 3 granule agent 0.01 to 30 67 to 99.5 0 to 8 ───────────────────────────────── The figures in the above table are Indicates weight percent.

【０１２３】施用に際しては、乳剤、油剤、フロアブル
剤及び水和剤では所定量の水で希釈して散布し、粉剤及
び粒剤は水で希釈することなく、そのまま直接散布す
る。Upon application, emulsions, oils, flowables and wettable powders are diluted with a predetermined amount of water and then sprayed, while powders and granules are directly sprayed without being diluted with water.

【０１２４】次に、上記の各製剤中の各成分の例を挙げ
る。乳剤 有効成分 ：本発明化合物 担 体 ：キシレン、ジメチルホルムアミド、メチ
ルナフタレン、シクロヘキサノン、ジクロロベンゼン、
イソホロン 界面活性剤 ：ソルポール2680、ソルポール3005X 、ソ
ルポール3353 その他の成分：ピペロニルブトキサイド、ベンゾトリア
ゾール油剤 有効成分 ：本発明化合物 担 体 ：キシレン、メチルセロソルブ、ケロシンフロアブル剤 有効成分 ：本発明化合物 担 体 ：水 界面活性剤 ：ルノックス1000C 、ソルポール3353、ソ
プロファーFL、ニッポール、アグリソールS-710 、リグ
ニンスルホン酸ソーダ その他の成分：ザンサンガム、ホルマリン、エチレング
リコール、プロピレングリコール水和剤 有効成分 ：本発明化合物 担 体 ：炭酸カルシウム、カオリナイト、ジーク
ライトＤ、ジークライトPFP 、珪藻土、タルク 界面活性剤 ：ソルポール5039、ルノックス1000C 、リ
グニンスルホン酸カルシウム、ドデシルベンゼンスルホ
ン酸ソーダ、ソルポール5050、ソルポール005D、ソルポ
ール5029-0 その他の成分：カープレックス＃80粉剤 有効成分 ：本発明化合物 担 体 ：炭酸カルシウム、カオリナイト、ジーク
ライトＤ、タルク その他の成分：ジイソプロピルホスフェート、カープレ
ックス＃80粒剤 (1) 有効成分 ：本発明化合物 担 体 ：炭酸カルシウム、カオリナイト、 ベン
トナイト、タルク その他の成分：リグニンスルホン酸カルシウム、ポリビ
ニールアルコール粒剤 (2) 〔ベイト剤〕 有効成分 ：本発明化合物 担 体 ：小麦粉、フスマ、コーン・グリット、ジ
ークライトＤ その他の成分：パラフィン、大豆油Next, examples of each component in each of the above-mentioned preparations will be given. Emulsion active ingredient: Compound of the present invention Carrier: Xylene, dimethylformamide, methylnaphthalene, cyclohexanone, dichlorobenzene,
Isophorone Surfactant: Sorpol 2680, Sorpol 3005X, Sorpol 3353 Other components: Piperonyl butoxide, benzotriazole oil Active ingredient: Compound of the present invention Carrier: Xylene, Methylcellosolve, Kerosene Flowable agent Active ingredient: Compound of the present invention Body: Water Surfactant: Lunox 1000C, Solpol 3353, Soprofer FL, Nipol, Aglycol S-710, Sodium lignin sulfonate Other ingredients: Zansan gum, formalin, ethylene glycol, propylene glycol wettable powder Active ingredient: Compound of the present invention Carrier: Calcium carbonate, kaolinite, Sieglite D, Sieglite PFP, diatomaceous earth, talc Surfactant: Solpol 5039, Lunox 1000C, calcium lignin sulfonate, sodium dodecylbenzene sulfonate, Solpol 5050 , Solpol 005D, Solpol 5029-0 Other ingredients: Carplex # 80 Powder Active ingredient: Compound of the present invention Carrier: Calcium carbonate, Kaolinite, Sikhlite D, Talc Other ingredients: Diisopropyl phosphate, Carplex # 80 granules (1) Active ingredient: compound of the present invention Carrier: calcium carbonate, kaolinite, bentonite, talc Other ingredients: calcium lignin sulfonate, polyvinyl alcohol granules (2) [bait agent] Active ingredient: compound of the present invention carrier : Flour, bran, corn grit, sieglite D Other ingredients: paraffin, soybean oil

【０１２５】[0125]

【実施例】実施例（合成例、製剤例、試験例） 以下、本発明について実施例（合成例、製剤例、試験
例）を挙げて具体的に詳述する。EXAMPLES Examples (Synthesis Examples, Formulation Examples, Test Examples) The present invention will be specifically described below with reference to Examples (Synthesis Examples, Formulation Examples, Test Examples).

【０１２６】〔合成例〕本発明に包含される化合物は、
以下に示した合成例に基づき製造したまたは製造するこ
とができたが、本発明はこれらの化合物にのみ限定され
るものではない。[Synthesis Example] The compounds included in the present invention are
Although prepared or could be prepared according to the synthetic examples shown below, the present invention is not limited to these compounds.

【０１２７】合成例１ ３−（４−クロロベンジル）−６−（２−クロロフェニ
ル）−２, ４（１Ｈ,３Ｈ）−ピリミジンジオン （本発明化合物 No. 1.8）水素化ナトリウム（純度55
％）0.30 gをジメチルホルムアミド20mLに加え、氷冷下
で撹拌しながら、エチル ３−アミノ−３−（２−クロ
ロフェニル）−２−プロペノエート1.58 gのジメチルホ
ルムアミド溶液５mLを滴下した。室温で15分間撹拌後、
エチル ４−クロロベンジルカーバメート1.50 gを加え
た。110 ℃で２時間撹拌後、減圧下で溶媒を留去した。
残留物を100 mLの水に溶解し、ジエチルエーテル100 mL
で洗浄後、水層を氷50 gと濃塩酸20mLの混合液中に加え
た。析出した結晶をろ過して集め、乾燥後、ジイソプロ
ピルエーテルで洗浄して、目的化合物を0.92 g得た。Synthesis Example 1 3- (4-chlorobenzyl) -6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (invention compound No. 1.8) sodium hydride (purity 55
%) 0.30 g was added to 20 mL of dimethylformamide, and 5 mL of a solution of ethyl 3-amino-3- (2-chlorophenyl) -2-propenoate (1.58 g) in dimethylformamide was added dropwise with stirring under ice cooling. After stirring for 15 minutes at room temperature,
1.50 g of ethyl 4-chlorobenzyl carbamate was added. After stirring at 110 ° C for 2 hours, the solvent was distilled off under reduced pressure.
Dissolve the residue in 100 mL of water and add 100 mL of diethyl ether.
After washing with, the aqueous layer was added to a mixed solution of 50 g of ice and 20 mL of concentrated hydrochloric acid. The precipitated crystals were collected by filtration, dried, and washed with diisopropyl ether to give the desired compound (0.92 g).

【０１２８】融点：170.0 − 172.5℃1 H-NMR(CDCl3 + CD3OD, TMS,δppm):4.09(1H, s), 4.98
(2H,s), 5.70(1H,s), 7.05〜7.50(8H, m).Melting point: 170.0-172.5 ° C. 1 H-NMR (CDCl 3 + CD 3 OD, TMS, δppm): 4.09 (1 H, s), 4.98
(2H, s), 5.70 (1H, s), 7.05 ~ 7.50 (8H, m).

【０１２９】合成例２ １−メチル−３−（４−クロロベンジル）−６−（２−
クロロフェニル）−２, ４（１Ｈ, ３Ｈ）−ピリミジン
ジオン （本発明化合物 No. 1.2)合成例１で合成した３−（４
−クロロベンジル）−６−（２−クロロフェニル）−
２, ４（１Ｈ, ３Ｈ）−ピリミジンジオン0.40 gおよび
炭酸カリウム0.16 gをジメチルホルムアミド10mLに加
え、室温で攪拌下、ヨウ化メチル0.20gを滴下した。室
温で12時間撹拌後、氷水100 mLに加え、酢酸エチル100
mLを加え抽出した。有機層を飽和食塩水で洗浄し、無水
硫酸ナトリウムで乾燥後、減圧下で溶媒留去して粗生成
物を0.42 g得た。この結晶をジイソプロピルエーテルと
イソプロピルアルコールの混合溶媒を用いて再結晶し、
目的化合物を0.35 g得た。Synthesis Example 2 1-Methyl-3- (4-chlorobenzyl) -6- (2-
Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.2) 3- (4 synthesized in Synthesis Example 1
-Chlorobenzyl) -6- (2-chlorophenyl)-
0.40 g of 2,4 (1H, 3H) -pyrimidinedione and 0.16 g of potassium carbonate were added to 10 mL of dimethylformamide, and 0.20 g of methyl iodide was added dropwise with stirring at room temperature. After stirring for 12 hours at room temperature, add to 100 mL of ice water and add ethyl acetate 100
Extracted by adding mL. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.42 g of a crude product. This crystal was recrystallized using a mixed solvent of diisopropyl ether and isopropyl alcohol,
0.35 g of the target compound was obtained.

【０１３０】融点：130.0 − 131.0℃1 H-NMR(CDCl3, TMS, δppm):3.10(3H, s), 5.17(2H,
s), 5.65(1H, s), 7.15〜7.60(8H, m).Melting point: 130.0-131.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.10 (3H, s), 5.17 (2H,
s), 5.65 (1H, s), 7.15 ~ 7.60 (8H, m).

【０１３１】合成例３ ３−（４−クロロ−α，α−ジメチルベンジル）−６−
（２−クロロフェニル）−２, ４（１Ｈ, ３Ｈ）−ピリ
ミジンジオン （本発明化合物 No. 1.16)水素化ナトリウム（純度55
％）0.40 gをジメチルホルムアミド20mLに加え、氷冷下
で撹拌しながら、エチル ３−アミノ−３−（２−クロ
ロフェニル）−２−プロペノエート2.00 gのジメチルホ
ルムアミド溶液５mLを滴下した。室温で15分間撹拌後、
再び氷冷下で撹拌しながら、４−クロロ−α，α−ジメ
チルベンジルイソシアネート1.80 gを滴下した。室温で
12時間撹拌後、減圧下で溶媒を留去した。残留物を100
mLの水に溶解し、ジエチルエーテル100 mLで洗浄後、水
層を氷50 gと濃塩酸20mLの混合液中に加えた。析出した
結晶をろ過して集め、乾燥後、ジイソプロピルエーテル
で洗浄して、目的化合物を1.10 g得た。Synthesis Example 3 3- (4-chloro-α, α-dimethylbenzyl) -6-
(2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.16) Sodium hydride (purity 55
%) 0.40 g was added to 20 mL of dimethylformamide, and 5 mL of a solution of 2.00 g of ethyl 3-amino-3- (2-chlorophenyl) -2-propenoate in dimethylformamide was added dropwise with stirring under ice-cooling. After stirring for 15 minutes at room temperature,
While stirring again under ice cooling, 1.80 g of 4-chloro-α, α-dimethylbenzyl isocyanate was added dropwise. At room temperature
After stirring for 12 hours, the solvent was distilled off under reduced pressure. 100 residues
After dissolving in mL of water and washing with 100 mL of diethyl ether, the aqueous layer was added to a mixed solution of 50 g of ice and 20 mL of concentrated hydrochloric acid. The precipitated crystals were collected by filtration, dried, and washed with diisopropyl ether to give the desired compound (1.10 g).

【０１３２】融点：200.0 − 201.0℃1 H-NMR(CDCl3 + DMSO d-6, TMS, δppm):1.89(6H, s),
4.35(1H, bs), 5.36(1H, s), 7.14(4H, s), 7.35(4H, b
s)Melting point: 200.0-201.0 ° C. 1 H-NMR (CDCl 3 + DMSO d-6, TMS, δ ppm): 1.89 (6 H, s),
4.35 (1H, bs), 5.36 (1H, s), 7.14 (4H, s), 7.35 (4H, b
s)

【０１３３】合成例４ １−メチル−３−（４−クロロ−α，α−ジメチルベン
ジル）−６−（２−クロロフェニル）−２, ４（１Ｈ,
３Ｈ）−ピリミジンジオン （本発明化合物 No. 1.21)合成例３で合成した３−（４
−クロロ−α，α−ジメチルベンジル）−６−（２−ク
ロロフェニル）−２,４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.50 g、ヨウ化メチル0.25 g及び炭酸カリウム0.22
gをジメチルホルムアミド20mLに加え、室温で12時間撹
拌した。減圧下で溶媒を留去後、酢酸エチル100 mLで抽
出した。有機層を水洗し、無水硫酸ナトリウムで乾燥
後、減圧下で溶媒を留去して目的化合物を0.49 g得た。Synthesis Example 4 1-Methyl-3- (4-chloro-α, α-dimethylbenzyl) -6- (2-chlorophenyl) -2,4 (1H,
3H) -pyrimidinedione (inventive compound No. 1.21) 3- (4) synthesized in Synthesis Example 3
-Chloro-α, α-dimethylbenzyl) -6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.50 g, methyl iodide 0.25 g and potassium carbonate 0.22
g was added to 20 mL of dimethylformamide, and the mixture was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with 100 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.49 g of the desired compound.

【０１３４】粘稠液体 1 H-NMR(CDCl3, TMS, δppm):1.98(6H,s), 2.95(3H,
s), 5.43(1H,s),7.14(4H,s), 7.20〜7.45(4H, m).Viscous liquid 1 H-NMR (CDCl 3 , TMS, δppm): 1.98 (6H, s), 2.95 (3H,
s), 5.43 (1H, s), 7.14 (4H, s), 7.20 ~ 7.45 (4H, m).

【０１３５】合成例５ １−メチル−３−（４−クロロベンジル−６−（４−フ
ルオロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジン
ジオン （本発明化合物 No. 1.14)合成例１に準じて合成した３
−（４−クロロベンジル）−６−（４−フルオロフェニ
ル）−２, ４（１Ｈ, ３Ｈ）−ピリミジンジオン0.30 g
とヨウ化メチル0.26 gおよび炭酸カリウム0.25 gをジメ
チルホルムアミド20mLに加え、室温で12時間撹拌した。
以下、合成例２に準じて行い目的化合物を0.31 g得た。Synthesis Example 5 1-Methyl-3- (4-chlorobenzyl-6- (4-fluorophenyl) -2,4 (1H, 3H) -pyrimidinedione (invention compound No. 1.14) Synthesis Example 1 3 synthesized according to
-(4-chlorobenzyl) -6- (4-fluorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.30 g
0.26 g of methyl iodide and 0.25 g of potassium carbonate were added to 20 mL of dimethylformamide, and the mixture was stirred at room temperature for 12 hours.
The following was performed according to Synthesis Example 2 to obtain 0.31 g of the desired compound.

【０１３６】融点：122.0 − 123.0℃ 1 H-NMR(CDCl3, TMS, δppm):3.20(3H,s), 5.14(2H,s),
5.70(1H,s), 7.00〜7.75(8H, m).Melting point: 122.0-123.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.20 (3H, s), 5.14 (2H, s),
5.70 (1H, s), 7.00 ~ 7.75 (8H, m).

【０１３７】合成例６ １−メチル−３−（４−クロロ−α−メチルベンジル）
−６−（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）
−ピリミジンジオン （本発明化合物 No. 1.49)合成例１に準じて合成した３
−（４−クロロ−α−メチルベンジル）−６−（２−ク
ロロフェニル）−２, ４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.25 gとヨウ化メチル0.20 gおよび炭酸カリウム0.
20 gをアセトニトリル20mLに加え、室温で12時間撹拌し
た。氷水100mL に加え、酢酸エチル100mL で抽出後、水
洗し、無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留
去して粗生成物を得た。これを展開溶媒としてクロロホ
ルムを用い、分取薄層クロマトグラフィーで精製して目
的化合物0.21 g得た。Synthesis Example 6 1-Methyl-3- (4-chloro-α-methylbenzyl)
-6- (2-chlorophenyl) -2,4 (1H, 3H)
-Pyrimidinedione (Compound No. 1.49 of the present invention) 3 synthesized according to Synthesis Example 1
0.25 g of-(4-chloro-α-methylbenzyl) -6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione, 0.20 g of methyl iodide and 0.2 g of potassium carbonate.
20 g was added to 20 mL of acetonitrile, and the mixture was stirred at room temperature for 12 hours. The mixture was added to 100 mL of ice water, extracted with 100 mL of ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was purified by preparative thin layer chromatography using chloroform as a developing solvent to obtain 0.21 g of the target compound.

【０１３８】粘稠液体 1 H-NMR(CDCl3, TMS, δppm):1.88(3H, d, J=7.0Hz),
2.04(3H, s), 5.61(1H, s), 6.28(1H, q, J=7.0Hz),7.0
0〜7.50(8H, m).Viscous liquid 1 H-NMR (CDCl 3 , TMS, δ ppm): 1.88 (3 H, d, J = 7.0 Hz),
2.04 (3H, s), 5.61 (1H, s), 6.28 (1H, q, J = 7.0Hz), 7.0
0 ~ 7.50 (8H, m).

【０１３９】合成例７ １−シアノメチル−３−（４−クロロベンジル）−６−
（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリ
ミジンジオン （本発明化合物 No. 1.75)合成例１で合成した３−（４
−クロロベンジル）−６−（２−クロロフェニル）−
２，４（１Ｈ, ３Ｈ）−ピリミジンジオン0.40 gをジメ
チルホルムアミド５mLに加え、氷冷下で撹拌しながら、
水素化ナトリウム( 純度55％）0.07gを添加した。室温
で30分間撹拌後、クロロアセトニトリル0.27gを滴下
し、90℃で２時間撹拌した。減圧下で溶媒を留去後、ジ
エチルエーテル100 mLで抽出した。有機層を水洗し、無
水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去して粗
結晶を得た。これをヘキサンで洗浄して目的化合物0.32
g得た。Synthesis Example 7 1-Cyanomethyl-3- (4-chlorobenzyl) -6-
(2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.75) 3- (4 synthesized in Synthesis Example 1
-Chlorobenzyl) -6- (2-chlorophenyl)-
2,4 (1H, 3H) -pyrimidinedione (0.40 g) was added to dimethylformamide (5 mL), and the mixture was stirred under ice-cooling.
0.07 g of sodium hydride (purity 55%) was added. After stirring at room temperature for 30 minutes, 0.27 g of chloroacetonitrile was added dropwise, and the mixture was stirred at 90 ° C for 2 hours. After distilling off the solvent under reduced pressure, the mixture was extracted with 100 mL of diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude crystals. This is washed with hexane to give the target compound 0.32
g got.

【０１４０】融点：240.0 − 241.0℃Melting point: 240.0-241.0 ° C.

【０１４１】合成例８ １−メチル−３−（４−クロロベンジル）−５−ブロモ
−６−（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）
−ピリミジンジオン （本発明化合物 No. 1.42)合成例１で合成した３−（４
−クロロベンジル）−６−（２−クロロフェニル）−
２，４（１Ｈ, ３Ｈ）−ピリミジンジオン1.5gを酢酸20
mLに加え、室温で撹拌しながら、臭素0.5 mLを滴下し
た。室温で２時間撹拌後、冷やした５％塩酸100 mLに加
え、析出した結晶をろ過して集めた。この結晶をジイソ
プロピルエーテルで洗浄後、乾燥して、３−（４−クロ
ロベンジル）−５−ブロモ−６−（２−クロロフェニ
ル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジオン1.3gを
得た。Synthesis Example 8 1-Methyl-3- (4-chlorobenzyl) -5-bromo-6- (2-chlorophenyl) -2,4 (1H, 3H)
-Pyrimidinedione (Compound of the present invention No. 1.42) 3- (4 synthesized in Synthesis Example 1
-Chlorobenzyl) -6- (2-chlorophenyl)-
1.5 g of 2,4 (1H, 3H) -pyrimidinedione was added to 20 g of acetic acid.
In addition to mL, 0.5 mL of bromine was added dropwise while stirring at room temperature. After stirring for 2 hours at room temperature, 100 mL of cooled 5% hydrochloric acid was added, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether and dried to give 1.3 g of 3- (4-chlorobenzyl) -5-bromo-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione. .

【０１４２】３−（４−クロロベンジル）−５−ブロモ
−６−（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）
−ピリミジンジオン0.7g、ヨウ化メチル0.34 gおよび炭
酸カリウム0.28 gをジメチルホルムアミド20mLに加え、
室温で１時間半撹拌した。減圧下で溶媒を留去後、酢酸
エチル100 mLで抽出した。有機層を水洗し、無水硫酸ナ
トリウムで乾燥後、減圧下で溶媒を留去して粗結晶を得
た。これをヘキサンで洗浄して目的を0.62 g得た。3- (4-chlorobenzyl) -5-bromo-6- (2-chlorophenyl) -2,4 (1H, 3H)
-0.7 g of pyrimidinedione, 0.34 g of methyl iodide and 0.28 g of potassium carbonate were added to 20 mL of dimethylformamide,
The mixture was stirred at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with 100 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude crystals. This was washed with hexane to obtain 0.62 g of the target.

【０１４３】融点：128.0 − 131.5℃1 H-NMR(CDCl3, TMS, δppm):3.14(3H, s), 5.21(2H,s),
7.10〜7.50(8H, m).Melting point: 128.0-131.5 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.14 (3H, s), 5.21 (2H, s),
7.10 ~ 7.50 (8H, m).

【０１４４】合成例９ ３−（４−クロロベンジル）−５−メチル−６−（２−
クロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジン
ジオン （本発明化合物 No. 1.61)水素化ナトリウム（純度55
％）0.30 gをジメチルホルムアミド20mLに加え、氷冷下
で撹拌しながら、エチル ３−アミノ−３−（２−クロ
ロフェニル）−２−メチル−２−プロペノエート1.65 g
のジメチルホルムアミド溶液５mLを滴下した。以下、合
成例１に準じて行い、目的化合物を0.85 g得た。Synthesis Example 9 3- (4-chlorobenzyl) -5-methyl-6- (2-
Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.61) Sodium hydride (purity 55
%) 0.30 g was added to 20 mL of dimethylformamide, and ethyl 3-amino-3- (2-chlorophenyl) -2-methyl-2-propenoate 1.65 g while stirring under ice cooling.
5 mL of the dimethylformamide solution of was added dropwise. The following procedure was performed according to Synthesis Example 1 to obtain 0.85 g of the desired compound.

【０１４５】融点：187.5 − 188.0℃1 H-NMR(CDCl3, TMS, δppm):1.76(3H, s), 5.01(2H,
s), 7.10〜7.60(8H, m).Melting point: 187.5-188.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 1.76 (3H, s), 5.01 (2H,
s), 7.10 ~ 7.60 (8H, m).

【０１４６】合成例１０ １−メチル−３−｛３−（４−クロロフェニル）−２−
プロペニル｝−６−（２−クロロフェニル）−２，４
（１Ｈ, ３Ｈ）−ピリミジンジオン （本発明化合物 No. 1.126）合成例２に準じて合成した
１−メチル−３−ベンジル−６−（２−クロロフェニ
ル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジオン14.2 g
をトルエン200 mLに加え、40℃で攪拌下、塩化アルミニ
ウム15.0 gを加えた。70〜80℃で３時間撹拌後、冷却
し、水500 mLを徐々に滴下した。析出した結晶をろ過し
て集め、ヘキサン200 mL及びジイソプロピルエーテル20
0 mLで洗浄後、乾燥して１−メチル−６−（２−クロロ
フェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジオン
を8.0 g 得た。Synthesis Example 10 1-Methyl-3- {3- (4-chlorophenyl) -2-
Propenyl} -6- (2-chlorophenyl) -2,4
(1H, 3H) -Pyrimidinedione (Compound of the present invention No. 1.126) 1-Methyl-3-benzyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidine synthesized according to Synthesis Example 2 Zion 14.2 g
Was added to 200 mL of toluene, and 15.0 g of aluminum chloride was added with stirring at 40 ° C. After stirring at 70 to 80 ° C. for 3 hours, the mixture was cooled and 500 mL of water was gradually added dropwise. The precipitated crystals were collected by filtration, and 200 mL of hexane and 20 ml of diisopropyl ether were collected.
After washing with 0 mL and drying, 8.0 g of 1-methyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione was obtained.

【０１４７】１−メチル−６−（２−クロロフェニル）
−２，４（１Ｈ,３Ｈ）−ピリミジンジオン0.50 g、４
−クロロシンナミルクロライド0.43 gおよび炭酸カリウ
ム0.58 gをジメチルホルムアミド20mLに加え、100 ℃で
３時間撹拌した。減圧下で溶媒を留去後、酢酸エチル10
0 mLを加えて抽出した。有機層を水洗し、無水硫酸ナト
リウムで乾燥後、減圧下で溶媒を留去して粗結晶を得
た。これをヘキサンで洗浄して目的を0.62 g得た。1-methyl-6- (2-chlorophenyl)
-2,4 (1H, 3H) -pyrimidinedione 0.50 g, 4
-0.43 g of chlorocinnamyl chloride and 0.58 g of potassium carbonate were added to 20 mL of dimethylformamide, and the mixture was stirred at 100 ° C for 3 hours. After distilling off the solvent under reduced pressure, ethyl acetate 10
Extraction was performed by adding 0 mL. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude crystals. This was washed with hexane to obtain 0.62 g of the target.

【０１４８】融点：166.0 − 169.0℃1 H-NMR(CDCl3, TMS, δppm):3.15(3H, m), 4.76(2H, d,
J=6Hz), 5.70(1H,s), 6.25〜6.90(2H,m), 7.15〜7.65
(4H, m).Melting point: 166.0-169.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.15 (3H, m), 4.76 (2H, d,
J = 6Hz), 5.70 (1H, s), 6.25 ~ 6.90 (2H, m), 7.15 ~ 7.65
(4H, m).

【０１４９】合成例１１ １−メチル−３−（４−クロロフェノキシエチル）−６
−（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピ
リミジンジオン （本発明化合物 No. 1.113）１−メチル−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.50 g、４−クロロフェノキシエチルブロマイド0.
63 gおよび炭酸カリウム0.46 gをジメチルホルムアミド
20mLに加え、室温で12時間撹拌した。減圧下で溶媒を留
去後、酢酸エチル100 mLで抽出した。有機層を水洗し、
無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去し
て、粗生成物を得た。これを展開溶媒としてベンゼンを
用い、分取薄層クロマトグラフィーで精製して目的化合
物を0.95g得た。Synthesis Example 11 1-Methyl-3- (4-chlorophenoxyethyl) -6
-(2-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.113) 1-methyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.50 g, 4-chlorophenoxyethyl bromide 0.
63 g and 0.46 g of potassium carbonate were added to dimethylformamide.
The mixture was added to 20 mL and stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with 100 mL of ethyl acetate. Wash the organic layer with water,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product. This was purified by preparative thin layer chromatography using benzene as a developing solvent to obtain 0.95 g of the desired compound.

【０１５０】融点：133.0 − 134.0℃1 H-NMR(CDCl3, TMS, δppm):3.13(3H, s), 4.20〜4.50
(4H,m), 5.67(1H, s), 6.80〜7.60(8H,m).Melting point: 133.0-134.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.13 (3H, s), 4.20 to 4.50
(4H, m), 5.67 (1H, s), 6.80 ~ 7.60 (8H, m).

【０１５１】合成例１２ １−メチル−３−ベンジルオキシメチル−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン （本発明化合物 No. 1.117）１−メチル−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.50 g、ベンジルクロロメチルエーテル0.33 gおよ
び炭酸カリウム0.58gをジメチルホルムアミド20mLに加
え、室温で12時間撹拌した。減圧下で溶媒を留去後、酢
酸エチル100 mLで抽出した。有機層を水洗し、無水硫酸
ナトリウムで乾燥後、減圧下で溶媒を留去して、粗生成
物を得た。これを展開溶媒としてベンゼンを用い、分取
薄層クロマトグラフィーで精製して目的化合物を0.68 g
得た。Synthesis Example 12 1-Methyl-3-benzyloxymethyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound of the present invention No. 1.117) 1-Methyl-6- ( 2-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (0.50 g), benzylchloromethyl ether (0.33 g) and potassium carbonate (0.58 g) were added to dimethylformamide (20 mL), and the mixture was stirred at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and the residue was extracted with 100 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product. Using benzene as a developing solvent, this was purified by preparative thin layer chromatography to give 0.68 g of the target compound.
Obtained.

【０１５２】粘稠液体1 H-NMR(CDCl3, TMS, δppm):3.10(3H, s), 4.78(2H,s),
5.58(2H, s),5.64(1H, s), 7.15〜7.65(9H,m).Viscous liquid 1 H-NMR (CDCl 3 , TMS, δppm): 3.10 (3H, s), 4.78 (2H, s),
5.58 (2H, s), 5.64 (1H, s), 7.15 ~ 7.65 (9H, m).

【０１５３】合成例１３ １−メチル−３−（４−クロロベンゾイル）−６−（２
−クロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジ
ンジオン （本発明化合物 No. 1.119）１−メチル−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.36 gおよび炭酸カリウム0.42 gをジメチルホルム
アミド20mLに加えて氷冷下で撹拌しながら、４−クロロ
ベンゾイルクロライド0.29 gを滴下した。70℃で３時間
撹拌後、減圧下で溶媒を留去し、酢酸エチル100 mLで抽
出した。有機層を水洗し、無水硫酸ナトリウムで乾燥
後、減圧下で溶媒を留去して、粗結晶を得た。これをヘ
キサンで洗浄して目的化合物を0.58 g得た。Synthesis Example 13 1-Methyl-3- (4-chlorobenzoyl) -6- (2
-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (invention compound No. 1.119) 1-methyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.36 g and carbonic acid 0.42 g of potassium was added to 20 mL of dimethylformamide, and 0.29 g of 4-chlorobenzoyl chloride was added dropwise while stirring under ice cooling. After stirring at 70 ° C. for 3 hours, the solvent was distilled off under reduced pressure, and the mixture was extracted with 100 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude crystals. This was washed with hexane to obtain 0.58 g of the desired compound.

【０１５４】融点： 78.0 − 81.0℃1 H-NMR(CDCl3, TMS, δppm):3.16(3H, s), 5.75(1H,s),
7.20〜8.00(8H,m).Melting point: 78.0-81.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.16 (3H, s), 5.75 (1H, s),
7.20 ~ 8.00 (8H, m).

【０１５５】合成例１４ １−メチル−３−（４−クロロフェナシル）−６−（２
−クロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジ
ンジオン （本発明化合物 No. 1.118）１−メチル−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.50 g、４−クロロフェナシルブロマイド0.49 gお
よび炭酸カリウム0.58 gをジメチルホルムアミド20mLに
加え、室温で12時間撹拌した。減圧下で溶媒を留去後、
酢酸エチル100 mLで抽出した。有機層を水洗し、無水硫
酸ナトリウムで乾燥後、減圧下で溶媒を留去して、粗結
晶を得た。これをジイソプロピルエーテルで洗浄して目
的化合物を0.50 g得た。Synthesis Example 14 1-Methyl-3- (4-chlorophenacyl) -6- (2
-Chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione (Compound No. 1.118) 1-methyl-6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.50 g, 4 -Chlorophenacyl bromide 0.49 g and potassium carbonate 0.58 g were added to dimethylformamide 20 mL, and it stirred at room temperature for 12 hours. After distilling off the solvent under reduced pressure,
It was extracted with 100 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give crude crystals. This was washed with diisopropyl ether to obtain 0.50 g of the desired compound.

【０１５６】融点：162.0 − 164.0℃1 H-NMR(CDCl3, TMS, δppm):3.16(3H, s), 5.43(2H,s),
5.75(1H,s) 7.25〜8.10(8H,m).Melting point: 162.0-164.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.16 (3H, s), 5.43 (2H, s),
5.75 (1H, s) 7.25 ~ 8.10 (8H, m).

【０１５７】合成例１５ ３−（４−ｔ−ブチルベンジル）−６−（２−クロロフ
ェニル）−（１Ｈ, ３Ｈ）−ピリミジン−２−チオン−
４−オン （本発明化合物 No. 1.101）水素化ナトリウム（純度55
％）0.25 gをジメチルホルムアミド10mLに加え、氷冷下
で撹拌下しながら、エチル ３−アミノ−３−（２−ク
ロロフェニル）−２−プロペノエート1.13 gのジメチル
ホルムアミド溶液５mLを滴下した。室温で15分間撹拌
後、再び氷冷下で撹拌しながら、４−ｔ−ブチルベンジ
ルイソチオシアネート1.03 gを添加した。110 ℃で１時
間撹拌後、減圧下で溶媒を留去した。水100 mLを加えて
溶解し、ジエチルエーテル100 mLで洗浄後、水層を氷50
gと濃塩酸20mLの混合液中に加えた。酢酸エチル100 mL
で抽出し、有機層を飽和食塩水で洗浄後、無水硫酸ナト
リウムで乾燥し、減圧下で溶媒を留去して粗生成物を得
た。これをジイソプロピルエーテルで洗浄して、目的化
合物を0.34 g得た。Synthesis Example 15 3- (4-t-butylbenzyl) -6- (2-chlorophenyl)-(1H, 3H) -pyrimidine-2-thione-
4-one (invention compound No. 1.101) sodium hydride (purity 55
%) 0.25 g was added to 10 mL of dimethylformamide, and 5 mL of a dimethylformamide solution of 1.13 g of ethyl 3-amino-3- (2-chlorophenyl) -2-propenoate was added dropwise with stirring under ice cooling. After stirring for 15 minutes at room temperature, 1.03 g of 4-t-butylbenzyl isothiocyanate was added with stirring again under ice cooling. After stirring at 110 ° C. for 1 hour, the solvent was distilled off under reduced pressure. Add 100 mL of water to dissolve and wash with 100 mL of diethyl ether.
g and 20 mL of concentrated hydrochloric acid were added to the mixture. 100 mL ethyl acetate
The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with diisopropyl ether to obtain 0.34 g of the desired compound.

【０１５８】融点：219.0 − 223.5℃1 H-NMR(CDCl3, TMS, δppm):1.30(9H, s), 5.52(2H,
s), 5.99(1H, s), 7.15〜7.50(8H, m), 9.80(1H, bs).Melting point: 219.0-223.5 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 1.30 (9H, s), 5.52 (2H,
s), 5.99 (1H, s), 7.15 ~ 7.50 (8H, m), 9.80 (1H, bs).

【０１５９】合成例１６ １−メチル−３−（４−クロロベンジル）−６−（２−
クロロフェニル）−（１Ｈ, ３Ｈ）−ピリミジン−２−
オン−４−チオン （本発明化合物 No. 1.103）合成例２で合成した１−メ
チル−３−（４−クロロベンジル）−６−（２−クロロ
フェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジオン
0.70 gおよびローソン試薬〔２，４−ビス（４−メトキ
シフェニル）−１，３−ジチア−２，４−ジホスフェタ
ン−２，４−ジスルフィド〕1.00 gを１，４−ジオキサ
ン20mLに加え、３時間還流下で撹拌した。減圧下で溶媒
を留去後、溶出液としてクロロホルムを用い、シリカゲ
ルカラムクロマトグラフィーで精製して粗生成物を0.65
g得た。これをジイソプロピルエーテルで再結晶して目
的化合物0.44 g得た。Synthesis Example 16 1-Methyl-3- (4-chlorobenzyl) -6- (2-
Chlorophenyl)-(1H, 3H) -pyrimidine-2-
On-4-thione (Compound of the present invention No. 1.103) 1-Methyl-3- (4-chlorobenzyl) -6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidine synthesized in Synthesis Example 2 Zeon
0.70 g and Lawson's reagent [2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide] 1.00 g were added to 1,4-dioxane 20 mL for 3 hours. Stir under reflux. After evaporating the solvent under reduced pressure, the residue was purified by silica gel column chromatography using chloroform as an eluent to give a crude product (0.65).
g got. This was recrystallized from diisopropyl ether to obtain 0.44 g of the desired compound.

【０１６０】融点：133.0 − 137.0℃1 H-NMR(CDCl3, TMS, δppm):3.10(3H, s), 5.70(2H,
s), 6.50(1H, s), 7.00〜7.60(8H, m).Melting point: 133.0-137.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.10 (3H, s), 5.70 (2H,
s), 6.50 (1H, s), 7.00 ~ 7.60 (8H, m).

【０１６１】合成例１７ １−メチル−３−（６−クロロ−３−ピリジルメチル）
−６−（２−クロロフェニル）−２，４（１Ｈ, ３Ｈ）
−ピリミジンジオン （本発明化合物 No. 2.1）合成例２に準じて合成した３
−（６−クロロ−３−ピリジルメチル）−６−（２−ク
ロロフェニル）−２，４（１Ｈ, ３Ｈ）−ピリミジンジ
オン0.50 g、ヨウ化メチル0.41 gおよび炭酸カリウム0.
29 gをジメチルホルムアミド20mLに加えて、室温で12時
間撹拌した。減圧下で、溶媒を留去後、酢酸エチル100
mLで抽出した。有機層を水洗し、無水硫酸ナトリウムで
乾燥後、減圧下で溶媒を留去して粗生成物を得た。これ
をジイソプロピルエーテルで洗浄して、目的化合物を0.
51 g得た。Synthesis Example 17 1-Methyl-3- (6-chloro-3-pyridylmethyl)
-6- (2-chlorophenyl) -2,4 (1H, 3H)
-Pyrimidinedione (inventive compound No. 2.1) 3 synthesized according to Synthesis Example 2
-(6-Chloro-3-pyridylmethyl) -6- (2-chlorophenyl) -2,4 (1H, 3H) -pyrimidinedione 0.50 g, methyl iodide 0.41 g and potassium carbonate 0.
29 g was added to 20 mL of dimethylformamide, and the mixture was stirred at room temperature for 12 hours. After distilling off the solvent under reduced pressure, ethyl acetate 100
Extracted with mL. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product. This was washed with diisopropyl ether to reduce the target compound to 0.
51 g was obtained.

【０１６２】融点：116.0 − 120.0℃1 H-NMR(CDCl3, TMS, δppm):3.09(3H, s), 5.12(2H,
s), 5.68(1H, s), 7.10〜8.70(7H, m).Melting point: 116.0-120.0 ° C. 1 H-NMR (CDCl 3 , TMS, δppm): 3.09 (3H, s), 5.12 (2H,
s), 5.68 (1H, s), 7.10 ~ 8.70 (7H, m).

【０１６３】上記合成例に従って第４表及び第５表に示
す化合物を合成したまたは合成することができた。第４
表及び第５表のＱ１〜Ｑ61は第１表及び第２表のＱ１〜
Ｑ61と同じ意味を示す。The compounds shown in Tables 4 and 5 were synthesized or could be synthesized according to the above synthesis examples. Fourth
Q1 to Q61 in Tables and Table 5 are Q1 to Q1 in Tables 1 and 2.
It has the same meaning as Q61.

【０１６４】第 ４ 表Table 4

【０１６５】[0165]

【化２８】 [Chemical 28]

【０１６６】[0166]

【表７０】 ────────────────────────────────── No. R1 R2 A Xl Ym Z1 Z2 融 点 (℃) ────────────────────────────────── 1.1 CH3 H -CH2- H 2-Cl O O 121.0-122.0 1.2 CH3 H -CH2- H 4-Cl O O 120.0-121.0 1.3 CH3 H -CH2- 2-Cl 2-Cl O O 170.0-171.0 1.4 CH3 H -CH2- 2-Cl 4-Cl O O 130.0-131.0 1.5 H H -CH2- H 2-Cl O O 256.0-259.0 1.6 H H -CH2- H 4-Cl O O 220.5-223.0 1.7 H H -CH2- 2-Cl 2-Cl O O 166.0-168.0 1.8 H H -CH2- 2-Cl 4-Cl O O 170.0-172.5 1.9 H H -CH2- 3-CF3 2-Cl O O 214.0-217.0 1.10 H H -CH2- 3-CF3 4-Cl O O 233.0-235.0 1.11 CH3 H -CH2- 3-CF3 2-Cl O O 182.0-184.0 1.12 CH3 H -CH2- 3-CF3 4-Cl O O 99.5-101.0 1.13 H H -CH2- 2-Cl 4-F O O 195.0-197.0 1.14 H H -CH2- 2-Cl 4-OCH3 O O 180.0-181.0 1.15 H H -CH2- 2-Cl 4-CH(CH3)2 O O 182.0-183.0 1.16 H H -C(CH3)2- 2-Cl 4-Cl O O 200.0-201.0 1.17 CH3 H -CH2- 2-Cl H O O 油状物 1.18 CH3 H -CH2- 2-Cl 4-F O O 油状物 1.19 CH3 H -CH2- 2-Cl 4-OCH3 O O 油状物 1.20 CH3 H -CH2- 2-Cl 4-CH(CH3)2 O 0 油状物 1.21 CH3 H -C(CH3)2- 2-Cl 4-Cl O O 油状物 1.22 CH2CH3 H -CH2- 2-Cl 4-Cl O O 111.0-112.0 1.23 CH2OCH3 H -CH2- 2-Cl 4-Cl O O 131.0-132.0 ──────────────────────────────────[Table 70] ────────────────────────────────── No. R 1 R 2 AX l Y m Z 1 Z 2 melting point (℃) ────────────────────────────────── 1.1 CH 3 H -CH 2 -H 2-Cl OO 121.0-122.0 1.2 CH 3 H -CH 2 - H 4-Cl OO 120.0-121.0 1.3 CH 3 H -CH 2 - 2-Cl 2-Cl OO 170.0-171.0 1.4 CH 3 H -CH 2 - 2 -Cl 4-Cl OO 130.0-131.0 1.5 HH -CH 2 - H 2-Cl OO 256.0-259.0 1.6 HH -CH 2 - H 4-Cl OO 220.5-223.0 1.7 HH -CH 2 - 2-Cl 2-Cl OO 166.0-168.0 1.8 HH -CH 2 - 2- Cl 4-Cl OO 170.0-172.5 1.9 HH -CH 2 - 3-CF 3 2-Cl OO 214.0-217.0 1.10 HH -CH 2 - 3-CF 3 4-Cl OO 233.0-235.0 1.11 CH 3 H -CH 2 - 3-CF 3 2-Cl OO 182.0-184.0 1.12 CH 3 H -CH 2 - 3-CF 3 4-Cl OO 99.5-101.0 1.13 HH -CH 2 - 2-Cl 4-FOO 195.0-197.0 1.14 HH -CH 2 - 2-Cl 4-OCH 3 OO 180.0-181.0 1.15 HH -CH 2 - 2-Cl 4-CH (CH 3) 2 OO 182.0-183.0 1.16 HH -C (CH 3) 2 - 2-Cl 4 -Cl OO 200.0-201.0 1.17 CH 3 H -CH 2 - 2-Cl HOO oil 1.18 CH 3 H -CH 2 - 2-Cl 4-FOO oil 1.19 CH 3 H -CH 2 - 2 -Cl 4-OCH 3 OO oil 1.20 CH 3 H -CH 2 - 2 -Cl 4-CH (CH 3) 2 O 0 oil object 1.21 CH 3 H -C (CH 3 ) 2 - 2-Cl 4-Cl OO oil 1.22 CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO 111.0-112.0 1.23 CH 2 OCH 3 H -CH 2 - 2-Cl 4-Cl OO 131.0-132.0 ──────────────────────────────────

【０１６７】[0167]

【表７１】 第 ４ 表 （ 続 ） ────────────────────────────────── No. R1 R2 A Xl Ym Z1 Z2 融 点 (℃) ────────────────────────────────── 1.24 CH2C6H5 H -CH2- 2-Cl 4-Cl O O 146.0-147.0 1.25 H H -CH2- 2-Cl 4-C(CH3)3 O O 213.0-214.0 1.26 H H -CH2- 2-Cl 4-CF3 O O 207.0-208.0 1.27 CH3 H -CH2- 2-Cl 4-C(CH3)3 O O 油状物 1.28 CH3 H -CH2- 2-Cl 4-CF3 O O 154.0-155.0 1.29 H H -CH2- 2-Cl 2,4-Cl2 O O 194.5-195.0 1.30 CH3 H -CH2- 2-F 4-Cl O O 油状物 1.31 CH3 H -CH2- 2-Br 4-Cl O O 111.0-112.0 1.32 CH3 H -CH2- 2-CF3 4-Cl O O 油状物 1.33 CH3 H -CH2- 2-CH3 4-Cl O O 102.0-105.0 1.34 CH3 H -CH2- 3-Cl 4-Cl O O 84.0- 88.0 1.35 CH3 H -CH2- 4-Cl 4-Cl O O 71.0- 75.0 1.36 CH3 H -CH2- 2,6-F2 4-Cl O O 123.0-124.0 1.37 CH3 H -CH2- 2-Cl-6-F 4-Cl O O 107.0-108.0 1.38 CH3 H -CH2- 2,6-Cl2 4-Cl O O 153.0-154.0 1.39 CH3 H -CH2- 2,4-Cl2 4-Cl O O 157.0-158.0 1.40 CH3 Cl -CH2- 2-Cl 4-Cl O O 104.5-107.5 1.41 CH3 Br -CH2- H 4-Cl O 0 171.0-173.5 1.42 CH3 Br -CH2- 2-Cl 4-Cl O O 128.0-131.5 1.43 CH3 Br -CH2- 3-Cl 4-Cl O O 194.0-198.0 1.44 CH3 Br -CH2- 4-Cl 4-Cl O O 油状物 1.45 CH3 I -CH2- H 4-Cl O O 190.0-192.0 ──────────────────────────────────[Table 71] Table 4 (continued) ─────────────────────────────────── No. R 1 R 2 AX l Y m Z 1 Z 2 Melting point (℃) ────────────────────────────────── 1.24 CH 2 C 6 H 5 H -CH 2 - 2-Cl 4-Cl OO 146.0-147.0 1.25 HH -CH 2 - 2-Cl 4-C (CH 3) 3 OO 213.0-214.0 1.26 HH -CH 2 - 2-Cl 4 -CF 3 OO 207.0-208.0 1.27 CH 3 H -CH 2 - 2-Cl 4-C (CH 3) 3 OO oil 1.28 CH 3 H -CH 2 - 2 -Cl 4-CF 3 OO 154.0-155.0 1.29 HH -CH 2 - 2-Cl 2,4- Cl 2 OO 194.5-195.0 1.30 CH 3 H -CH 2 - 2-F 4-Cl OO oil 1.31 CH 3 H -CH 2 - 2 -Br 4-Cl OO 111.0 -112.0 1.32 CH 3 H -CH 2 - 2-CF 3 4-Cl OO oil 1.33 CH 3 H -CH 2 - 2 -CH 3 4-Cl OO 102.0-105.0 1.34 CH 3 H -CH 2 - 3-Cl 4-Cl OO 84.0- 88.0 1.35 CH 3 H -CH 2 - 4-Cl 4-Cl OO 71.0- 75.0 1.36 CH 3 H -CH 2 - 2,6-F 2 4-Cl OO 123.0-124.0 1.37 CH 3 H -CH 2 - 2-Cl-6 -F 4-Cl OO 107.0-108.0 1.38 CH 3 H -CH 2 - 2,6-Cl 2 4-Cl OO 153.0-154.0 1.39 CH 3 H -CH 2 - 2,4-Cl 2 4 -Cl OO 157.0-158.0 1.40 CH 3 Cl -CH 2 - 2-Cl 4-Cl OO 104.5-107.5 1.41 CH 3 Br -CH 2 - H 4-Cl O 0 171.0 -173.5 1.42 CH 3 Br -CH 2 - 2-Cl 4-Cl OO 128.0-131.5 1.43 CH 3 Br -CH 2 - 3-Cl 4-Cl OO 194.0-198.0 1.44 CH 3 Br -CH 2 - 4-Cl 4 -Cl OO Oil 1.45 CH 3 I -CH 2 -H 4-Cl OO 190.0-192.0 ────────────────────────────── ─────

【０１６８】[0168]

【表７２】 第 ４ 表 （ 続 ） ────────────────────────────────── No. R1 R2 A Xl Y Z1 Z2 融 点 (℃) ────────────────────────────────── 1.46 CH3 I -CH2- 2-Cl 4-Cl O O 146.5-147.5 1.47 CH3 CH3 -CH2- 2-Cl 4-Cl O O 183.0-186.0 1.48 CH3 H -CH2- 2-Cl 2,4-Cl2 O O 152.0-153.0 1.49 CH3 H -CH(CH3)- 2-Cl 4-Cl O O 油状物 1.50 CH3 H -CH2CH2- 2-Cl 4-Cl O O 油状物 1.51 H H -CH2- 2-CF3 4-Cl O O 125.0-128.0 1.52 H Br -CH2- H 4-Cl O O 221.5-224.5 1.53 H Br -CH2- 3-Cl 4-Cl O O 217.0-221.0 1.54 H Br -CH2- 4-Cl 4-Cl O O 213.5-219.0 1.55 H I -CH2- H 4-Cl O O 225.0-227.5 1.56 H H -CH(CH3)- 2-Cl 4-Cl O O 208.0-212.0 1.57 H H -CH2CH2- 2-Cl 4-Cl O O 193.0-197.5 1.58 H Cl -CH2- 2-Cl 4-Cl O O 196.0-198.0 1.59 H Br -CH2- 2-Cl 4-Cl O O 226.5-227.5 1.60 H I -CH2- 2-Cl 4-Cl O O 233.0-235.0 1.61 H CH3 -CH2- 2-Cl 4-Cl O O 187.5-188.0 1.62 H H -CH2- 2-F 4-Cl O O 199.0-201.0 1.63 H H -CH2- 2-Br 4-Cl O 0 177.0-178.0 1.64 H H -CH2- 2-CH3 4-Cl O O 180.0-182.0 1.65 H H -CH2- 3-Cl 4-Cl O O 224.0-226.0 1.66 H H -CH2- 4-Cl 4-Cl O O 166.0-169.0 1.67 H H -CH2- 2,6-F2 4-Cl O O 168.0-169.0 ──────────────────────────────────[Table 72] Table 4 (continued) ─────────────────────────────────── No. R 1 R 2 AX l YZ 1 Z 2 Melting point (℃) ────────────────────────────────── 1.46 CH 3 I- CH 2 - 2-Cl 4- Cl OO 146.5-147.5 1.47 CH 3 CH 3 -CH 2 - 2-Cl 4-Cl OO 183.0-186.0 1.48 CH 3 H -CH 2 - 2-Cl 2,4-Cl 2 OO 152.0-153.0 1.49 CH 3 H -CH (CH 3) - 2-Cl 4-Cl OO oil 1.50 CH 3 H -CH 2 CH 2 - 2-Cl 4-Cl OO oil 1.51 HH -CH 2 - 2- CF 3 4-Cl OO 125.0-128.0 1.52 H Br -CH 2 - H 4-Cl OO 221.5-224.5 1.53 H Br -CH 2 - 3-Cl 4-Cl OO 217.0-221.0 1.54 H Br -CH 2 - 4- Cl 4-Cl OO 213.5-219.0 1.55 HI -CH 2 - H 4-Cl OO 225.0-227.5 1.56 HH -CH (CH 3) - 2-Cl 4-Cl OO 208.0-212.0 1.57 HH -CH 2 CH 2 - 2 -Cl 4-Cl OO 193.0-197.5 1.58 H Cl -CH 2 - 2-Cl 4-Cl OO 196.0-198.0 1.59 H Br -CH 2 - 2-Cl 4-Cl OO 226.5-227.5 1.60 HI -CH 2 - 2 -Cl 4-Cl OO 233.0-235.0 1.61 H CH 3 -CH 2 - 2-Cl 4-Cl OO 187.5-188.0 1.62 HH -CH 2 - 2-F 4- Cl OO 199.0-201.0 1.63 HH -CH 2 - 2-Br 4-Cl O 0 177.0-178.0 1.64 HH -CH 2 - 2-CH 3 4-Cl OO 180.0-182.0 1.65 HH -CH 2 - 3-Cl 4- Cl OO 224.0-226.0 1.66 HH -CH 2 - 4-Cl 4-Cl OO 166.0-169.0 1.67 HH -CH 2 - 2,6-F 2 4-Cl OO 168.0-169.0 ─ ──────────────────────────────────

【０１６９】[0169]

【表７３】 第 ４ 表 （ 続 ） ────────────────────────────────── No. R1 R2 A Xl Ym Z1 Z2 融 点 (℃) ────────────────────────────────── 1.68 H H -CH2- 2-Cl-6-F 4-Cl O O 169.0-171.0 1.69 H H -CH2- 2,6-Cl2 4-Cl O O 208.0-209.0 1.70 H H -CH2- 2,4-Cl2 4-Cl O O 221.0-222.0 1.71 CH3 H -CH2- 2-Cl 4-Br O O 149.0-150.0 1.72 CH3 H -CH2- 2-Cl 3,4-Cl2 O O 98.5-100.0 1.73 H H -CH2- 2-Cl 4-Br O O 188.5-191.0 1.74 H H -CH2- 2-Cl 3,4-Cl2 O O 219.5-221.5 1.75 CH2CN H -CH2- 2-Cl 4-Cl O O 143.0-145.5 1.76 CH2CO2C2H5 H -CH2- 2-Cl 4-Cl O O 油状物 1.77 CH2CH2CH3 H -CH2- 2-Cl 4-Cl O O 114.5-116.0 1.78 CH2CH=CH2 H -CH2- 2-Cl 4-Cl O O 油状物 1.79 CH2C≡CH H -CH2- 2-Cl 4-Cl O O 136.5-138.5 1.80 H H -CH2- 3,4-Cl2 4-Cl O O 260.0-262.0 1.81 CH3 H -CH2- 3,4-Cl2 4-Cl O O 油状物 1.82 H H -CH2- 4-Br 4-Cl O O 289.0-290.0 1.83 CH3 H -CH2- 4-Br 4-Cl O O 油状物 1.84 H H -CH2- 4-C6H5 4-Cl O O 280.0-282.0 1.85 CH3 H -CH2- 4-C6H5 4-Cl O 0 油状物 1.86 H H -CH2- 4-CF3 4-Cl O O 220.0-221.0 1.87 CH3 H -CH2- 4-CF3 4-Cl O O 油状物 1.88 S(C6H4-4-Cl) H -CH2- 2-Cl 4-Cl O O 135.5-139.0 1.89 H H -CH2- 4-CH3 4-Cl O O 271.0-272.0 ───────────────────────────────────[Table 73] Table 4 (continued) ────────────────────────────────── No. R 1 R 2 AX l Y m Z 1 Z 2 Melting point (℃) ────────────────────────────────── 1.68 HH- CH 2 - 2-Cl-6 -F 4-Cl OO 169.0-171.0 1.69 HH -CH 2 - 2,6-Cl 2 4-Cl OO 208.0-209.0 1.70 HH -CH 2 - 2,4-Cl 2 4- Cl OO 221.0-222.0 1.71 CH 3 H -CH 2 - 2-Cl 4-Br OO 149.0-150.0 1.72 CH 3 H -CH 2 - 2-Cl 3,4-Cl 2 OO 98.5-100.0 1.73 HH -CH 2 - 2-Cl 4-Br OO 188.5-191.0 1.74 HH -CH 2 - 2-Cl 3,4-Cl 2 OO 219.5-221.5 1.75 CH 2 CN H -CH 2 - 2-Cl 4-Cl OO 143.0-145.5 1.76 CH 2 CO 2 C 2 H 5 H -CH 2 - 2-Cl 4-Cl OO oil 1.77 CH 2 CH 2 CH 3 H -CH 2 - 2-Cl 4-Cl OO 114.5-116.0 1.78 CH 2 CH = CH 2 H -CH 2 - 2-Cl 4 -Cl OO oil 1.79 CH 2 C≡CH H -CH 2 - 2-Cl 4-Cl OO 136.5-138.5 1.80 HH -CH 2 - 3,4-Cl 2 4-Cl OO 260.0-262.0 1.81 CH 3 H -CH 2 - 3,4-Cl 2 4-Cl OO oil 1.82 HH -CH 2 - 4-Br 4-Cl OO 289.0-290.0 1.8 3 CH 3 H -CH 2-4 -Br 4-Cl OO Oil 1.84 HH -CH 2-4 -C 6 H 5 4-Cl OO 280.0-282.0 1.85 CH 3 H -CH 2-4 -C 6 H 5 4-Cl O 0 oil 1.86 HH -CH 2 - 4-CF 3 4-Cl OO 220.0-221.0 1.87 CH 3 H -CH 2 - 4-CF 3 4-Cl OO oil 1.88 S (C 6 H 4 - 4-Cl) H -CH 2 - 2-Cl 4-Cl OO 135.5-139.0 1.89 HH -CH 2 - 4-CH 3 4-Cl OO 271.0-272.0 ────────────── ─────────────────────

【０１７０】[0170]

【表７４】 第 ４ 表 （ 続 ） ─────────────────────────────────── No. R1 R2 A Xl Ym Z1 Z2 融 点 (℃) ─────────────────────────────────── 1.90 CH3 H -CH2- 4-CH3 4-Cl O O 138.0-140.0 1.91 H H -C(CH3)2 4-Cl 4-Cl O O 204.0-205.0 1.92 CH3 H -C(CH3)2 4-Cl 4-Cl O O 油状物 1.93 H H -C(CH3)2 4-Br 4-Cl O O 206.0-207.0 1.94 CH3 H -C(CH3)2 4-Br 4-Cl O O 油状物 1.95 H H -C(CH3)2 4-CH3 4-Cl O O 222.0-223.0 1.96 CH3 H -C(CH3)2 4-CH3 4-Cl O O 油状物 1.97 H H -C(CH3)2 4-F 4-Cl O O 216.0-217.0 1.98 CH3 H -C(CH3)2 4-F 4-Cl O O 94.0- 97.0 1.99 H H -C(CH3)2 4-CF3 4-Cl O O 155.0-158.0 1.100 CH3 H -C(CH3)2 4-CF3 4-Cl O O 油状物 1.101 H H -CH2- 2-Cl 4-C(CH3)3 S O 219.0-223.5 1.102 H H -CH2- 2-Cl 4-Cl O S 170.5-174.0 1.103 CH3 H -CH2- 2-Cl 4-Cl O S 133.0-137.0 1.104 H H -CH2- 2-Cl 4-OCH2CH2CH3 O O 170.0-172.0 1.105 CH3 H -CH2- 2-Cl 4-OCH2CH2CH3 O O 油状物 1.106 CHF2 H -CH2- 2-Cl 4-Cl O O 99.0-100.5 1.107 CH3 H -CH2- 2-Cl 4-CH=CHC6H5 O 0 78.0- 82.0 1.108 CH3 H -CH2- 2-Cl 4-C6H5 O O 143.0-144.0 1.109 CH3 H -CH2CH2O- 2-Cl 2,6-(CH3)2-4-O(C6H4-4-CH3) O O 油状物 1.110 H H -CH2- 4-F 4-Cl O O 249.0-251.0 1.111 CH3 H -CH2- 4-F 4-Cl O O 122.0-123.0 ───────────────────────────────────[Table 74] Table 4 (continued) ──────────────────────────────────── No. R 1 R 2 AX l Y m Z 1 Z 2 Melting point (℃) ─────────────────────────────────── 1.90 CH 3 H -CH 2-4 -CH 3 4-Cl OO 138.0-140.0 1.91 HH -C (CH 3 ) 2 4-Cl 4-Cl OO 204.0-205.0 1.92 CH 3 H -C (CH 3 ) 2 4- Cl 4-Cl OO oil 1.93 HH -C (CH 3 ) 2 4-Br 4-Cl OO 206.0-207.0 1.94 CH 3 H -C (CH 3 ) 2 4-Br 4-Cl OO oil 1.95 HH -C (CH 3) 2 4-CH 3 4-Cl OO 222.0-223.0 1.96 CH 3 H -C (CH 3) 2 4-CH 3 4-Cl OO oil 1.97 HH -C (CH 3) 2 4-F 4 -Cl OO 216.0-217.0 1.98 CH 3 H -C (CH 3 ) 2 4-F 4-Cl OO 94.0- 97.0 1.99 HH -C (CH 3 ) 2 4-CF 3 4-Cl OO 155.0-158.0 1.100 CH 3 H -C (CH 3) 2 4 -CF 3 4-Cl OO oil 1.101 HH -CH 2 - 2-Cl 4-C (CH 3) 3 SO 219.0-223.5 1.102 HH -CH 2 - 2-Cl 4- Cl OS 170.5-174.0 1.103 CH 3 H -CH 2 - 2-Cl 4-Cl OS 133.0-137.0 1.104 HH -CH 2 - 2-Cl 4-OCH 2 CH 2 CH 3 OO 170.0-172. 0 1.105 CH 3 H -CH 2 - 2-Cl 4-OCH 2 CH 2 CH 3 OO oil 1.106 CHF 2 H -CH 2 - 2 -Cl 4-Cl OO 99.0-100.5 1.107 CH 3 H -CH 2 - 2 -Cl 4-CH = CHC 6 H 5 O 0 78.0- 82.0 1.108 CH 3 H -CH 2 - 2-Cl 4-C 6 H 5 OO 143.0-144.0 1.109 CH 3 H -CH 2 CH 2 O- 2-Cl 2,6- (CH 3 ) 2 -4-O (C 6 H 4 -4-CH 3 ) OO Oil 1.110 HH -CH 2-4 -F 4-Cl OO 249.0-251.0 1.111 CH 3 H -CH 2 -4-F 4-Cl OO 122.0-123.0 ────────────────────────────────────

【０１７１】[0171]

【表７５】 第 ４ 表 （ 続 ） ────────────────────────────────── No. R1 R2 A Xl Ym Z1 Z2 融 点 (℃) ────────────────────────────────── 1.112 CH3 H -CH2- 2-Cl 4-CO2C(CH3)3 O O 56.0- 60.0 1.113 CH3 H -CH2CH2O- 2-Cl 4-Cl O O 133.0-134.0 1.114 CH3 H -CH2- 2-Cl 4-NO2 O O 127.0-129.0 1.115 CH3 H -CH2- 2-Cl 4-CH2Cl O O 97.0-102.0 1.116 CH3 H -CH2- 2-Cl 4-O(C6H3-2-Cl-4-CF3) O O 128.0-129.0 1.117 CH3 H -CH2OCH2- 2-Cl H O O 油状物 1.118 CH3 H -CH2CO- 2-Cl 4-Cl O O 162.0-164.0 1.119 CH3 H -CO- 2-Cl 4-Cl O O 78.0- 81.0 1.120 CH3 H -CH2- 2-Cl 4-(C6H4-4-Cl) O O 149.0-153.0 1.121 CH3 H -CH2- 2-Cl 4-CO2CH3 O O 120.0-122.0 1.122 CH3 H -CH2- 2-Cl 4-OCH2C≡CH O O 油状物 1.123 CH3 H -CH2- 2-Cl 4-CO2CH2CF3 O O 133.0-134.0 1.124 CH3 H -CH2- 2-Cl 4-CO(C6H3-3,4-Cl2) O O 143.0-148.0 1.125 CH3 H -CH2C(CH3)=CH- 2-Cl 4-C6H5 O O 142.0-144.0 1.126 CH3 H -CH2CH=CH- 2-Cl 4-Cl O O 166.0-169.0 1.127 H H -CH2- 2-CF3 2,4-Cl2 O O 179.0-181.0 1.128 H H -CH2- 2-CF3 4-CH3 O O 177.0-180.0 1.129 H H -CH2- 2-CF3 2-Cl O O 156.0-157.0 1.130 H H -CH2- 2-CF3 3-Cl O O 167.0-169.0 ──────────────────────────────────[Table 75] Table 4 (continued) ─────────────────────────────────── No. R 1 R 2 AX l Y m Z 1 Z 2 Melting point (℃) ────────────────────────────────── 1.112 CH 3 H -CH 2 - 2-Cl 4 -CO 2 C (CH 3) 3 OO 56.0- 60.0 1.113 CH 3 H -CH 2 CH 2 O- 2-Cl 4-Cl OO 133.0-134.0 1.114 CH 3 H -CH 2 - 2-Cl 4-NO 2 OO 127.0-129.0 1.115 CH 3 H -CH 2 - 2-Cl 4-CH 2 Cl OO 97.0-102.0 1.116 CH 3 H -CH 2 - 2-Cl 4-O (C 6 H 3 -2-Cl-4-CF 3) OO 128.0-129.0 1.117 CH 3 H -CH 2 OCH 2 - 2-Cl HOO oil 1.118 CH 3 H -CH 2 CO- 2 -Cl 4-Cl OO 162.0-164.0 1.119 CH 3 H -CO- 2-Cl 4-Cl OO 78.0- 81.0 1.120 CH 3 H -CH 2 - 2-Cl 4- (C 6 H 4 -4-Cl) OO 149.0-153.0 1.121 CH 3 H -CH 2 - 2-Cl 4-CO 2 CH 3 OO 120.0-122.0 1.122 CH 3 H -CH 2 - 2-Cl 4-OCH 2 C≡CH OO oil 1.123 CH 3 H -CH 2 - 2 -Cl 4-CO 2 CH 2 CF 3 OO 133.0-134.0 1.124 CH 3 H -CH 2 - 2-Cl 4-CO (C 6 H 3 -3,4-Cl 2) OO 143.0-148.0 1.125 CH 3 H -CH 2 C (CH 3 ) = CH- 2-Cl 4-C 6 H 5 OO 142.0-144.0 1.126 CH 3 H -CH 2 CH = CH- 2-Cl 4-Cl OO 166.0-169.0 1.127 HH -CH 2 - 2-CF 3 2,4- Cl 2 OO 179.0-181.0 1.128 HH -CH 2 - 2-CF 3 4-CH 3 OO 177.0-180.0 1.129 HH -CH 2 - 2-CF 3 2-Cl OO 156.0- 157.0 1.130 HH -CH 2 - 2- CF 3 3-Cl OO 167.0-169.0 ──────────────────────────────── ──

【０１７２】第 ５ 表Table 5

【０１７３】[0173]

【化２９】 [Chemical 29]

【０１７４】[0174]

【表７６】 ─────────────────────────────────── No. R1 R2 A Xl B Z1 Z2 融 点 (℃) ─────────────────────────────────── 2.1 H H -CH2- 2-Cl Q39-6-Cl O O 164.0-172.0 2.2 CH3 H -CH2- 2-Cl Q39-6-Cl O O 112.0-120.0 2.3 CH3 H -CH2- 2-Cl Q49 O O 58.0- 60.0 2.4 CH3 H -CH2- 2-Cl Q7 O O 油状物 2.5 CH3 H -CH2- 2-Cl Q6 O O 油状物 2.6 CH3 H -CH2- 2-Cl Q40 O O 177.0-178.0 ───────────────────────────────────[Table 76] ─────────────────────────────────── No. R 1 R 2 AX l BZ 1 Z 2 melting point (℃) ─────────────────────────────────── 2.1 HH -CH 2 - 2-Cl Q39-6-Cl OO 164.0-172.0 2.2 CH 3 H -CH 2 - 2-Cl Q39-6-Cl OO 112.0-120.0 2.3 CH 3 H -CH 2 - 2-Cl Q49 OO 58.0- 60.0 2.4 CH 3 H - CH 2 - 2-Cl Q7 OO oil 2.5 CH 3 H -CH 2 - 2 -Cl Q6 OO oil 2.6 CH 3 H -CH 2 - 2 -Cl Q40 OO 177.0-178.0 ───────── ───────────────────────────

【０１７５】〔製剤例〕次に、本発明化合物を有効成分
とする害虫防除剤の製剤例を示すが、本発明はこれらに
限定されるものではない。尚、以下の製剤例において、
「部」は重量部を意味する。[Formulation Example] Next, formulation examples of the pest control agent containing the compound of the present invention as an active ingredient will be shown, but the present invention is not limited thereto. In the following formulation examples,
"Parts" means parts by weight.

【０１７６】製剤例１ 乳 剤 本発明化合物 ・・・・・・・・・・ 5 部 キシレン ・・・・・・・・・・ 70 部 N,N −ジメチルホルムアミド・・・・・・・・・・ 20 部 ソルポール２６８０ ・・・・・・・・・・ 5 部 （非イオン性界面活性剤とアニオン性界面活性剤との混
合物：東邦化学工業 (株) 商品名） 以上を均一に混合して乳剤とする。 Formulation Example 1 Emulsion Compound of the present invention: 5 parts Xylene: 70 parts N, N-Dimethylformamide: ... 20 parts Solpol 2680 ... 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) To make an emulsion.

【０１７７】使用に際しては、上記乳剤を50〜20000 倍
に希釈して有効成分量がヘクタール当たり0.005 〜50kg
になるように散布する。In use, the above emulsion was diluted 50 to 20000 times to obtain an amount of active ingredient of 0.005 to 50 kg per hectare.
Sprinkle so that

【０１７８】製剤例２ 水和剤 本発明化合物 ・・・・・・・・・・ 25 部 ジークライトＰＦＰ ・・・・・・・・・・ 66 部 （カオリナイトとセリサイトの混合物：ジークライト工
業 (株) 商品名） ソルポール５０３９ ・・・・・・・・・・ 4 部 （アニオン性界面活性剤：東邦化学工業 (株) 商品名） カープレックス＃８０ ・・・・・・・・・・ 3 部 （ホワイトカーボン：塩野義製薬 (株) 商品名） リグニンスルホン酸カルシウム・・・・・・・・ 2 部 以上を均一に混合粉砕して水和剤とする。 Formulation Example 2 Wettable powder Compound of the present invention: 25 parts Dichlorite PFP: 66 parts (mixture of kaolinite and sericite: Sikhlite Kogyo Co., Ltd. product name: Solpol 5039 ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 4 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) Carplex # 80 ・ ・ ・ ・・ 3 parts (White carbon: trade name of Shionogi Pharmaceutical Co., Ltd.) Calcium lignin sulfonate ・ ・ ・ ・ ・ ・ 2 parts Mix evenly the above to make wettable powder.

【０１７９】使用に際しては、上記水和剤を50〜20000
倍に希釈して有効成分量がヘクタール当たり0.005 〜50
kgになるように散布する。When using, the above-mentioned wettable powder is added to 50 to 20000.
Diluted twice and the amount of active ingredient is 0.005 to 50 per hectare
Disperse to kg.

【０１８０】製剤例３ 油 剤 本発明化合物 ・・・・・・・・・・ 10 部 メチルセルソルブ ・・・・・・・・・・ 90 部 以上を均一に混合して油剤とする。使用に際しては、上
記油剤を有効成分量がヘクタール当たり0.005 〜50kgに
なるように散布する。 Formulation Example 3 Oil agent Compound of the present invention: 10 parts Methyl cellosolve: 90 parts The above ingredients are uniformly mixed to obtain an oil agent. At the time of use, the above oil agent is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

【０１８１】製剤例４ 粉 剤 本発明化合物 ・・・・・・・・・・3.0 部 カープレックス＃８０ ・・・・・・・・・・0.5 部 （ホワイトカーボン：塩野義製薬 (株) 商品名） クレー ・・・・・・・・・・ 95 部 リン酸ジイソプロピル ・・・・・・・・・・1.5 部 以上を均一に混合粉砕して粉剤とする。 Formulation Example 4 Powder Compound of the present invention: 3.0 parts Carplex # 80: 0.5 part (White carbon: Shionogi & Co., Ltd. product Name) Clay ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 95 parts Diisopropyl phosphate ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 1.5 parts The above is uniformly mixed and pulverized into a powder.

【０１８２】使用に際しては、上記粉剤を有効成分量が
ヘクタール当たり0.005 〜50kgになるように散布する。At the time of use, the above dust is sprinkled so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

【０１８３】製剤例５ 粒 剤 本発明化合物 ・・・・・・・・・・ 5 部 ベントナイト ・・・・・・・・・・ 54 部 タルク ・・・・・・・・・・ 40 部 リグニンスルホン酸カルシウム・・・・・・・・・・1 部 以上を均一に混合粉砕して少量の水を加えて攪拌混合
し、押出式造粒機で造粒し、乾燥して粒剤とする。 Formulation Example 5 granules Compound of the present invention ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 5 parts Bentonite ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 54 parts Talc ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 40 parts Lignin Calcium sulfonate: 1 part Evenly mix and crush the above, add a small amount of water, stir and mix, granulate with an extrusion granulator, and dry to obtain granules ..

【０１８４】使用に際しては、上記粒剤を有効成分量が
ヘクタール当たり0.005 〜50kgになるように散布する。In use, the above granules are sprinkled so that the amount of active ingredient is 0.005 to 50 kg per hectare.

【０１８５】製剤例６ フロアブル剤 本発明化合物 ・・・・・・・・・・ 35 部 ソルポール３３５３ ・・・・・・・・・・ 10 部 （非イオン性界面活性剤：東邦化学工業 (株) 商品名） ルノックス１０００Ｃ ・・・・・・・・ 0.5 部 （陰イオン界面活性剤：東邦化学工業 (株) 商品名） １％ザンサンガム水溶液 ・・・・・・・・・・ 20 部 （天然高分子） 水 ・・・・・・・・ 4.5 部 有効成分（本発明化合物）を除く上記の成分を均一に溶
解し、次いで本発明化合物を加えよく攪拌した後、サン
ドミルにて湿式粉砕してフロアブル剤を得る。 Formulation Example 6 Flowable agent Compound of the present invention 35 parts Solpol 3353 10 parts (Nonionic surfactant: Toho Chemical Industry Co., Ltd. ) Product name: Lunox 1000C ・ ・ ・ ・ ・ ・ 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) 1% xanthan gum aqueous solution ・ ・ ・ ・ ・ ・ ・ ・ ・ ・ 20 parts (natural Polymer) Water ... 4.5 parts The above components except the active ingredient (the compound of the present invention) are uniformly dissolved, the compound of the present invention is added, and the mixture is stirred well and wet-ground with a sand mill. Get a flowable agent.

【０１８６】使用に際しては、上記フロアブル剤を50〜
20000 倍に希釈して有効成分量がヘクタール当たり0.00
5 〜50kgになるように散布する。When using the above flowable agent,
Diluted 20000 times and the amount of active ingredient is 0.00 per hectare
Sprinkle so that it is 5 to 50 kg.

【０１８７】〔試験例〕次に、本発明化合物の有害生物
防除剤としての有用性について、以下の試験例において
具体的に説明する。[Test Example] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples.

【０１８８】試験例１ ニジュウヤホシテントウに対す
る殺虫試験 明細書に記載された本発明化合物の５％乳剤（化合物に
よっては25％水和剤を供試）を展着剤の入った水で希釈
して、1000ppm 濃度の薬液に調整しこの薬液中にトマト
の葉を約10秒間浸漬し、風乾後シャーレに入れ、この中
にニジュウヤホシテントウ２令幼虫をシャーレ当たり10
頭を放虫し、蓋をして25℃恒温室に収容し、６日間経過
後の死虫率を下記の計算式から求めた。尚、試験は２区
制で行なった。 Test Example 1 Insecticidal test against Cistanche Tubulosa 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent. And tomato leaves are soaked in this chemical solution for about 10 seconds, air-dried and placed in a petri dish, and 2 larvae of the Nostoc communis second larvae are placed in this dish for 10 pets per dish.
The head was released, the lid was put, and it was stored in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test was conducted in a two-division system.

【０１８９】 死虫率（％）＝ (死虫数／放虫数）×１００ その結果、以下の化合物が１００％の死虫率を示した。Mortality of mortality (%) = (number of mortality / number of mortality) × 100 As a result, the following compounds showed a mortality of 100%.

【０１９０】本発明化合物：1.16、1.17、1.18、1.20、
1.28、1.31、1.32、1.36、1.37、1.38、1.39、1.40、1.
41、1.42、1.44、1.48、1.49、1.61、1.71、1.72、1.7
8、1.82、1.87、2.2 。Compounds of the present invention: 1.16, 1.17, 1.18, 1.20,
1.28, 1.31, 1.32, 1.36, 1.37, 1.38, 1.39, 1.40, 1.
41, 1.42, 1.44, 1.48, 1.49, 1.61, 1.71, 1.72, 1.7
8, 1.82, 1.87, 2.2.

【０１９１】試験例２ ナミハダニに対する殺ダニ効力
試験 インゲンの葉をリーフパンチを用いて径3.0 cmの円形に
切り取り、径７cmのスチロールカップ上の湿った濾紙上
に置いた。これにナミハダニ幼虫を１葉当たり10頭接種
した。明細書に記載された本発明化合物の５％乳剤（化
合物によっては25％水和剤を供試）を展着剤の入った水
で希釈して、1000 ppm濃度の薬液に調整しこの薬液をス
チロールカップ当たり２mLずつ回転式散布塔を用いて散
布し、25℃の恒温室に収容し、96時間経過後の死虫率を
下記の計算式から求めた。尚、試験は２区制で行なっ
た。 Test Example 2 Acaricidal efficacy test against spider mites The leaf of green beans was cut into a circle with a diameter of 3.0 cm using a leaf punch and placed on a damp filter paper on a styrene cup having a diameter of 7 cm. Ten head mite larvae were inoculated to each leaf. A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was tested) was diluted with water containing a spreading agent to prepare a 1000 ppm concentration chemical solution, and this chemical solution was used. 2 mL per styrene cup was sprayed using a rotary spraying tower, stored in a thermostatic chamber at 25 ° C., and the mortality rate after 96 hours was calculated from the following formula. The test was conducted in a two-division system.

【０１９２】 死虫率（％）＝ (死虫数／放虫数）×１００ その結果、以下の化合物が１００％の死虫率を示した。Mortality of mortality (%) = (number of mortality / number of larvae) × 100 As a result, the following compounds showed a mortality of 100%.

【０１９３】本発明化合物：1.4 、1.11、1.12、1.18、
1.20、1.21、1.22、1.23、1.27、1.28、1.30、1.31、1.
32、1.35、1.36、1.37、1.49、1.56、1.72、1.76、1.7
8、1.81、1.83、1.87、1.91、1.98、1.105 、1.108 、
2.2 。Compounds of the Invention: 1.4, 1.11, 1.12, 1.18,
1.20, 1.21, 1.22, 1.23, 1.27, 1.28, 1.30, 1.31, 1.
32, 1.35, 1.36, 1.37, 1.49, 1.56, 1.72, 1.76, 1.7
8, 1.81, 1.83, 1.87, 1.91, 1.98, 1.105, 1.108,
2.2.

【０１９４】[0194]

【発明の効果】本発明化合物は多くの農業害虫、ハダニ
類に対して優れた殺虫・殺ダニ活性を有し、かつ哺乳
類、魚類及び益虫に対してはほとんど悪影響を及ぼさな
い。従って、本発明化合物は、有用な有害生物防除剤を
提供することができる。INDUSTRIAL APPLICABILITY The compound of the present invention has excellent insecticidal and acaricidal activity against many agricultural pests and mites, and has almost no adverse effect on mammals, fish and beneficial insects. Therefore, the compound of the present invention can provide a useful pest control agent.

フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｄ 403/06 8829−4Ｃ 403/12 8829−4Ｃ 405/06 8829−4Ｃ 405/12 8829−4Ｃ 409/06 8829−4Ｃ 409/12 8829−4Ｃ 413/06 8829−4Ｃ 413/12 8829−4Ｃ 417/06 9051−4Ｃ 417/12 9051−4Ｃ (72)発明者 八木 和生 千葉県船橋市坪井町722番地１ 日産化学 工業株式会社中央研究所内 (72)発明者 大屋 栄一 千葉県船橋市坪井町722番地１ 日産化学 工業株式会社中央研究所内 (72)発明者 梅原 利之 埼玉県南埼玉郡白岡町大字白岡1470 日産 化学工業株式会社生物科学研究所内 (72)発明者 工藤 正毅 埼玉県南埼玉郡白岡町大字白岡1470 日産 化学工業株式会社生物科学研究所内 (72)発明者 井上 洋一 埼玉県南埼玉郡白岡町大字白岡1470 日産 化学工業株式会社生物科学研究所内Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical display location C07D 403/06 8829-4C 403/12 8829-4C 405/06 8829-4C 405/12 8829-4C 409/06 8829-4C 409/12 8829-4C 413/06 8829-4C 413/12 8829-4C 417/06 9051-4C 417/12 9051-4C (72) Inventor Kazuo Yagi 722-1, Tsuboi-cho, Funabashi-shi, Chiba Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Eiichi Oya 1 722, Tsuboi-cho, Funabashi, Chiba Prefecture Nissan Chemical Industry Co., Ltd. Central Research Laboratory (72) Inventor Toshiyuki Umehara 1470 Shiraoka, Shiraoka-cho, Minami Saitama-gun, Saitama Nissan Chemical Industrial Co., Ltd., Institute of Biological Sciences (72) Inventor Masaki Kudo 1470, Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences (72) Inoue Yoichi 1470, Shiraoka, Shirooka-cho, Minami-Saitama-gun, Saitama 1470 Nissan Kagaku Industry Research Institute for Biological Sciences

Claims (2)

【特許請求の範囲】[Claims] 【請求項１】 一般式〔Ｉ〕 【化１】 《式中、R1は水素原子、C1〜C4アルキル基、C2〜C4アル
ケニル基、C2〜C4アルキニル基、C1〜C4ハロアルキル
基、C2〜C4アルコキシアルキル基、ホルミル基、C2〜C6
アルキルカルボニル基、C2〜C6アルコキシカルボニル
基、C3〜C6アルコキシカルボニルアルキル基、C2〜C6シ
アノアルキル基、ベンジル基、フェニル基、シアノ基、
アミノ基、C3〜C6アルコキシカルボニルカルボニル基、
-SR10 基｛ただし、R10 はC2〜C6アルコキシカルボニル
基、C1〜C6アルキルスルホニル基、-NR1 1R12基（ただ
し、R11 はC1〜C6アルキル基を示し、R12 はC1〜C6アル
キル基、C2〜C6アルコキシカルボニル基、C3〜C9アルコ
キシカルボニルアルキル基、C1〜C6アルキルスルホニル
基、C2〜C6アルキルカルボニル基、C3〜C9ジアルキルア
ミノカルボニル基、C2〜C6ジアルキルアミノスルホニル
基ないし未置換または置換されていてもよいフェニル基
を示す）、ないし未置換または置換されていてもよいフ
ェニル基（ただし、置換されていてもよい置換基として
はハロゲン原子、シアノ基、ニトロ基、C1〜C4アルキル
基、C1〜C4ハロアルキル基、C1〜C4アルコキシ基、C1〜
C4ハロアルコキシ基、C1〜C4アルキルチオ基、C1〜C4ハ
ロアルキルチオ基、C2〜C6アルコキシカルボニル基、C2
〜C6ハロアルコキシカルボニル基、C2〜C6アルキルカル
ボニル基、C2〜C6ハロアルキルカルボニル基、C1〜C4ア
ルキルスルホニル基またはC1〜C4ハロアルキルスルホニ
ル基を示し、置換基が２個以上の場合は置換基は同一で
あっても異なっていてもよい）を示す。｝、アルカリ金
属またはアルカリ土類金属を示し、 R2は水素原子、ハロゲン原子、C1〜C4アルキル基、C1〜
C4ハロアルキル基、C1〜C4ヒドロキシアルキル基、C2〜
C4アルコキシアルキル基、C2〜C4アルキルチオアルキル
基、チオール基、C1〜C4アルキルチオ基、C1〜C4アルキ
ルスルフィニル基、C1〜C4アルキルスルホニル基、C1〜
C4ハロアルキルチオ基、C1〜C4ハロアルキルスルフィニ
ル基、C1〜C4ハロアルキルスルホニル基、ヒドロキシ
基、C1〜C4アルコキシ基、C1〜C4ハロアルコキシ基、ホ
ルミル基、シアノ基、ニトロ基、アミド基またはチオシ
アネート基を示し、 Z1、Z2は各々独立して酸素原子、イオウ原子またはイミ
ノ基を示し、 Ｘはハロゲン原子、C1〜C4アルキル基、C1〜C4アルコキ
シ基、C1〜C4アルキルチオ基、C1〜C4ハロアルキル基、
C1〜C4ハロアルコキシ基、C1〜C4ハロアルキルチオ基、
アミノ基、シアノ基、またはニトロ基を示し、ｌは０〜
５の整数（ただし、２〜５の場合はＸは同一であっても
異なっていてもよい）を示し、 Ａは 【化２】 【化３】 【化４】 （ただし、R3〜R10 はそれぞれ独立して、水素原子、シ
アノ基、水酸基、フェニル基またはC1〜C6アルキル基を
示し、R11 は水素原子、C1〜C6アルキル基、C2〜C6アル
ケニル基、C2〜C6アルキニル基、C2〜C6アルキルカルボ
ニル基またはベンジル基を示し、ｎは０〜２の整数を示
す。）を示し、 Ｂは 【化５】 〔ただし、Ｙはハロゲン原子、C1〜C6アルキル基、C2〜
C6アルケニル基、C2〜C6アルキニル基、C3〜C6シクロア
ルキル基、C1〜C6ハロアルキル基、C2〜C6ハロアルケニ
ル基、C2〜C6ハロアルキニル基、C3〜C6ハロシクロアル
キル基、C2〜C6シアノアルキル基、C1〜C6ヒドロキシア
ルキル基、C2〜C6カルボキシアルキル基、C1〜C6アルコ
キシ基、C2〜C6アルケニルオキシ基、C2〜C6アルキニル
オキシ基、C3〜C6シクロアルキルオキシ基、C1〜C6ハロ
アルコキシ基、C2〜C6ハロアルケニルオキシ基、C2〜C6
ハロアルキニルオキシ基、C3〜C6ハロシクロアルコキシ
基、C4〜C7ハロシクロアルキルアルコキシ基、C1〜C6ア
ルキルチオ基、C2〜C6アルケニルチオ基、C2〜C6アルキ
ニルチオ基、C3〜C6シクロアルキルチオ基、C1〜C6ハロ
アルキルチオ基、C1〜C6アルキルスルフィニル基、C2〜
C6アルケニルスルフィニル基、C2〜C6アルキニルスルフ
ィニル基、C3〜C6シクロアルキルスルフィニル基、C1〜
C6ハロアルキルスルフィニル基、C1〜C6アルキルスルホ
ニル基、C2〜C6アルケニルスルホニル基、C2〜C6アルキ
ニルスルホニル基、C3〜C6シクロアルキルスルホニル
基、C1〜C6ハロアルキルスルホニル基、C2〜C6アルコキ
シアルキル基、C2〜C6アルコキシアルコキシ基、C2〜C6
ハロアルコキシアルキル基、C2〜C6ハロアルコキシアル
コキシ基、C2〜C6アルキルチオアルキル基、C2〜C6アル
キルチオアルコキシ基、C3〜C6アルコキシカルボニルア
ルキル基、C3〜C6アルキルカルボニルアルキル基、C2〜
C6アルコキシカルボニルオキシ基、C2〜C6アルキルカル
ボニルオキシ基、C2〜C6アルキルカルボニル基、C3〜C6
アルケニルカルボニル基、C3〜C6アルキニルカルボニル
基、C4〜C7シクロアルキルカルボニル基、C2〜C6ハロア
ルキルカルボニル基、C2〜C6アルコキシカルボニル基、
C2〜C6ハロアルコキシカルボニル基、C3〜C6アルコキシ
カルボニルアルコキシ基、ニトロ基、シアノ基、ヒドロ
キシ基、カルボキシル基、チオシアネート基、イソチオ
シアネート基、C2〜C6チオシアネートアルキル基、C1〜
C6アルキルスルホニルオキシ基、C2〜C6アルキルチオカ
ルボニル基、メチレンジオキシ基、ハロメチレンジオキ
シ基、エチレンジオキシ基、ハロエチレンジオキシ基、
トリメチルシリル基または 【化６】 ｛ただし、Ｗは 【化７】 （ただし、R3、R4、R11 およびｎは前記と同じ意味を示
す）を示し、 ｑは０または１の整数を示し、 Arは無置換または置換されていてもよいフェニル基、ナ
フチル基、フリル基、チエニル基、ピロリル基、ピラゾ
リル基、イミダゾリル基、チアゾリル基、イソチアゾリ
ル基、オキサゾリル基、イソオキサゾリル基、オキサジ
アゾリル基、チアジアゾリル基、トリアゾリル基、ピリ
ジル基、ピリダジル基、ピリミジル基、ピラジル基、キ
ノリル基またはキノキザリル基（ただし、置換されてい
てもよい置換基としてはハロゲン原子、シアノ基、ニト
ロ基、C1〜C4アルキル基、C1〜C4ハロアルキル基、C1〜
C4アルコキシ基、C1〜C4ハロアルキコシ基、C1〜C4アル
キルチオ基、C1〜C4ハロアルキルチオ基、C1〜C4アルキ
ルスルホニル基、C1〜C4ハロアルキルスルホニル基、C2
〜C4アルコキシカルボニル基、カルボキシル基、アミノ
基、モノC1〜C4アルキルアミノ基、ジC1〜C4アルキルア
ミノ基、フェニル基、ベンジル基、メチレンジオキシ基
またはハロメチレンジオキシ基を示し、置換基が２個以
上の場合は置換基は同一であっても異なっていてもよ
い）を示す。｝を示し、 ｍは０〜５の整数（ただし、２〜５の場合はＹは同一で
あっても異なっていてもよい）を示す。〕または、未置
換または置換されていてもよいナフチル基、フリル基、
チエニル基、ピロリル基、ピラゾリル基、イミダゾリル
基、チアゾリル基、イソチアゾリル基、オキサゾリル
基、イソオキサゾリル基、チアジアゾリル基、オキサジ
アゾリル基、トリアゾリル基、ピリジル基、ピリダジル
基、ピリミジル基、ピラジル基、キノリル基、キノキザ
リル基、ベンゾフリル基、ベンゾチエニル基、インドリ
ル基、ベンゾオキサゾリル基またはベンゾチアゾリル基
（ただし、置換されていてもよい置換基としてはハロゲ
ン原子、シアノ基、ニトロ基、C1〜C4アルキル基、C1〜
C4ハロアルキル基、C1〜C4アルコキシ基、C1〜C4ハロア
ルコキシ基、C1〜C4アルキルチオ基、C1〜C4ハロアルキ
ルチオ基、C1〜C4アルキルスルホニル基、C1〜C4ハロア
ルキルスルホニル基、C2〜C4アルコキシカルボニル基、
カルボキシル基、アミノ基、モノC1〜C4アルキルアミノ
基、ジC1〜C4アルキルアミノ基、フェニル基、フェノキ
シ基またはベンジル基を示し、置換基が２個以上の場合
は置換基は同一であっても異なっていてもよい）を示
し、 また１−メチル−３−ベンジル−６−フェニル−２，４
（１Ｈ，３Ｈ）−ピリミジンジオン、３−ベンジル−６
−（２−ビニル−４，５−ジメトキシフェニル）−２，
４−（１Ｈ，３Ｈ）−ピリミジンジオンおよび３−ベン
ジル−６−（２−エチル−４，５−ジメトキシフェニ
ル）−２，４−（１Ｈ，３Ｈ）−ピリミジンジオンは除
く》で表わされるウラシル誘導体。1. A compound represented by the general formula [I]: << In the formula, R 1 is a hydrogen atom, a C 1 to C 4 alkyl group, a C 2 to C 4 alkenyl group, a C 2 to C 4 alkynyl group, a C 1 to C 4 haloalkyl group, and a C 2 to C 4 alkoxyalkyl group. , Formyl group, C 2 -C 6
Alkylcarbonyl, C 2 -C 6 alkoxycarbonyl group, C 3 -C 6 alkoxycarbonylalkyl group, C 2 -C 6 cyanoalkyl group, a benzyl group, a phenyl group, a cyano group,
Amino group, C 3 -C 6 alkoxycarbonyl group,
-SR 10 group {However, R 10 is C 2 -C 6 alkoxycarbonyl group, C 1 -C 6 alkylsulfonyl group, -NR 1 1 R 12 group (wherein, R 11 represents a C 1 -C 6 alkyl group , R 12 is C 1 -C 6 alkyl groups, C 2 -C 6 alkoxycarbonyl groups, C 3 -C 9 alkoxycarbonylalkyl groups, C 1 -C 6 alkylsulfonyl groups, C 2 -C 6 alkylcarbonyl groups, C 3 to C 9 dialkylaminocarbonyl group, C 2 to C 6 dialkylaminosulfonyl group or an unsubstituted or optionally substituted phenyl group), or an unsubstituted or optionally substituted phenyl group (provided that it is substituted) As the optionally substituted substituent, a halogen atom, a cyano group, a nitro group, a C 1 to C 4 alkyl group, a C 1 to C 4 haloalkyl group, a C 1 to C 4 alkoxy group, and a C 1 to
C 4 haloalkoxy group, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 2 -C 6 alkoxycarbonyl group, C 2
To C 6 haloalkoxycarbonyl group, C 2 to C 6 alkylcarbonyl group, C 2 to C 6 haloalkylcarbonyl group, C 1 to C 4 alkylsulfonyl group or C 1 to C 4 haloalkylsulfonyl group, wherein the substituent is 2 In the case of more than one, the substituents may be the same or different). }, An alkali metal or an alkaline earth metal, and R 2 is a hydrogen atom, a halogen atom, a C 1 to C 4 alkyl group, or a C 1 to
C 4 haloalkyl group, C 1 -C 4 hydroxyalkyl group, C 2 ~
C 4 alkoxyalkyl group, C 2 -C 4 alkylthioalkyl group, a thiol group, C 1 -C 4 alkylthio group, C 1 -C 4 alkylsulfinyl group, C 1 -C 4 alkylsulfonyl group, C 1 ~
C 4 haloalkylthio group, C 1 -C 4 haloalkylsulfinyl group, C 1 -C 4 haloalkylsulfonyl group, hydroxy group, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy group, a formyl group, a cyano group, A nitro group, an amido group or a thiocyanate group, Z 1 and Z 2 each independently represent an oxygen atom, a sulfur atom or an imino group, and X represents a halogen atom, a C 1 -C 4 alkyl group, C 1 -C 4 alkoxy groups, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkyl group,
C 1 -C 4 haloalkoxy groups, C 1 -C 4 haloalkylthio group,
Represents an amino group, a cyano group, or a nitro group, and l is 0 to
Represents an integer of 5 (provided that in the case of 2 to 5, X may be the same or different), and A is [Chemical 3] [Chemical 4] (However, R 3 to R 10 are each independently a hydrogen atom, a cyano group, a hydroxyl group, a phenyl group or a C 1 to C 6 alkyl group, and R 11 is a hydrogen atom, a C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 2 to C 6 alkylcarbonyl group or benzyl group, and n is an integer of 0 to 2), and B is [However, Y is a halogen atom, C 1 to C 6 alkyl group, C 2 to
C 6 alkenyl group, C 2 -C 6 alkynyl group, C 3 -C 6 cycloalkyl group, C 1 -C 6 haloalkyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 haloalkynyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 cyanoalkyl group, C 1 -C 6 hydroxyalkyl group, C 2 -C 6 carboxyalkyl group, C 1 -C 6 alkoxy group, C 2 -C 6 alkenyloxy group, C 2 -C 6 alkynyloxy group, C 3 -C 6 cycloalkyl group, C 1 -C 6 haloalkoxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6
Haloalkynyloxy group, C 3 -C 6 halocycloalkyl alkoxy group, C 4 -C 7 halocycloalkyl alkoxy group, C 1 -C 6 alkylthio group, C 2 -C 6 alkenylthio group, C 2 -C 6 alkynylthio group, C 3 -C 6 cycloalkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfinyl group, C 2 ~
C 6 alkenylsulfinyl group, C 2 -C 6 alkynylsulfinyl group, C 3 -C 6 cycloalkyl alkylsulfinyl group, C 1 ~
C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 2 -C 6 alkenylsulfonyl group, C 2 -C 6 alkynylsulfonyl group, C 3 -C 6 cycloalkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkoxyalkoxy, C 2 -C 6
Haloalkoxyalkyl group, C 2 -C 6 haloalkoxy alkoxy group, C 2 -C 6 alkylthioalkyl group, C 2 -C 6 alkylthioalkoxy group, C 3 -C 6 alkoxycarbonylalkyl group, C 3 -C 6 alkylcarbonyl alkyl group, C 2 ~
C 6 alkoxycarbonyl group, C 2 -C 6 alkylcarbonyloxy group, C 2 -C 6 alkylcarbonyl group, C 3 -C 6
Alkenylcarbonyl group, C 3 -C 6 alkynyl group, C 4 -C 7 cycloalkylcarbonyl group, C 2 -C 6 haloalkylcarbonyl group, C 2 -C 6 alkoxycarbonyl group,
C 2 -C 6 haloalkoxycarbonyl groups, C 3 -C 6 alkoxycarbonylalkoxy group, nitro group, cyano group, hydroxy group, carboxyl group, thiocyanate group, isothiocyanate group, C 2 -C 6 thiocyanate alkyl group, C 1 ~
C 6 alkylsulfonyloxy group, C 2 -C 6 alkylthiocarbonyl group, methylenedioxy group, halo methylenedioxy group, ethylenedioxy group, halo ethylenedioxy group,
Trimethylsilyl group or {However, W is (Wherein R 3 , R 4 , R 11 and n have the same meanings as described above), q represents an integer of 0 or 1, and Ar represents an unsubstituted or optionally substituted phenyl group or naphthyl group. , Furyl group, thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl Group or quinoxalyl group (however, the optionally substituted substituent is a halogen atom, a cyano group, a nitro group, a C 1 to C 4 alkyl group, a C 1 to C 4 haloalkyl group, a C 1 to
C 4 alkoxy, C 1 -C 4 Haroarukikoshi group, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 4 alkylsulfonyl group, C 1 -C 4 haloalkylsulfonyl groups, C 2
To C 4 alkoxycarbonyl group, carboxyl group, amino group, mono C 1 to C 4 alkylamino group, di C 1 to C 4 alkylamino group, phenyl group, benzyl group, methylenedioxy group or halomethylenedioxy group. When two or more substituents are present, the substituents may be the same or different. }, And m represents an integer of 0 to 5 (provided that in the case of 2 to 5, Y may be the same or different). ] Or an unsubstituted or optionally substituted naphthyl group, a furyl group,
Thienyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, quinolyl group, quinoxalyl group , A benzofuryl group, a benzothienyl group, an indolyl group, a benzoxazolyl group or a benzothiazolyl group (however, the optionally substituted substituent is a halogen atom, a cyano group, a nitro group, a C 1 to C 4 alkyl group, C 1 ~
C 4 haloalkyl group, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy groups, C 1 -C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 4 alkylsulfonyl group, C 1 To C 4 haloalkylsulfonyl group, C 2 to C 4 alkoxycarbonyl group,
Indicates a carboxyl group, amino group, mono C 1 -C 4 alkylamino group, di C 1 -C 4 alkylamino group, phenyl group, phenoxy group or benzyl group. Or 1-methyl-3-benzyl-6-phenyl-2,4
(1H, 3H) -Pyrimidinedione, 3-benzyl-6
-(2-vinyl-4,5-dimethoxyphenyl) -2,
Uracil derivative represented by 4- (1H, 3H) -pyrimidinedione and 3-benzyl-6- (2-ethyl-4,5-dimethoxyphenyl) -2,4- (1H, 3H) -pyrimidinedione . 【請求項２】 請求項１記載のウラシル誘導体の１種ま
たは２種以上を有効成分として含有する有害生物防除
剤。2. A pest control agent containing one or more uracil derivatives according to claim 1 as active ingredients.
JP3202914A 1991-08-13 1991-08-13 Uracil derivative and pest control agent Pending JPH0543555A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP3202914A JPH0543555A (en) 1991-08-13 1991-08-13 Uracil derivative and pest control agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3202914A JPH0543555A (en) 1991-08-13 1991-08-13 Uracil derivative and pest control agent

Publications (1)

Publication Number Publication Date
JPH0543555A true JPH0543555A (en) 1993-02-23

Family

ID=16465263

Family Applications (1)

Application Number Title Priority Date Filing Date
JP3202914A Pending JPH0543555A (en) 1991-08-13 1991-08-13 Uracil derivative and pest control agent

Country Status (1)

Country Link
JP (1) JPH0543555A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998040362A1 (en) * 1997-03-10 1998-09-17 Bayer Aktiengesellschaft Substituted arylalkyluracils
JP2005154419A (en) * 2003-11-04 2005-06-16 Sumitomo Chemical Co Ltd 6-arylpyrimidinone compound and use of the same
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
WO2017090654A1 (en) * 2015-11-26 2017-06-01 住友化学株式会社 Pest control composition and use thereof
CN107074781A (en) * 2014-10-03 2017-08-18 住友化学株式会社 Pyrimidinone compound
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones
US10183949B2 (en) * 2014-08-29 2019-01-22 The University Of Tokyo Pyrimidinone derivative having autotaxin-inhibitory activity

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998040362A1 (en) * 1997-03-10 1998-09-17 Bayer Aktiengesellschaft Substituted arylalkyluracils
JP2005154419A (en) * 2003-11-04 2005-06-16 Sumitomo Chemical Co Ltd 6-arylpyrimidinone compound and use of the same
JP4661163B2 (en) * 2003-11-04 2011-03-30 住友化学株式会社 6-Arylpyrimidinone compounds and uses thereof
US9873673B2 (en) 2011-11-11 2018-01-23 Pfizer Inc. 2-thiopyrimidinones
US8841314B2 (en) 2011-11-11 2014-09-23 Pfizer Inc. 2-Thiopyrimidinones
US9399626B2 (en) 2011-11-11 2016-07-26 Pfizer Inc. 2-thiopyrimidinones
US8835449B2 (en) 2011-11-11 2014-09-16 Pfizer Inc. 2-thiopyrimidinones
US10183949B2 (en) * 2014-08-29 2019-01-22 The University Of Tokyo Pyrimidinone derivative having autotaxin-inhibitory activity
CN107074781A (en) * 2014-10-03 2017-08-18 住友化学株式会社 Pyrimidinone compound
EP3202762A4 (en) * 2014-10-03 2018-03-14 Sumitomo Chemical Company, Limited Pyrimidinone compound
CN107074781B (en) * 2014-10-03 2020-01-17 住友化学株式会社 Pyrimidinone compounds
US9771332B2 (en) 2015-05-05 2017-09-26 Pfizer Inc. 2-thiopyrimidinones
WO2017090654A1 (en) * 2015-11-26 2017-06-01 住友化学株式会社 Pest control composition and use thereof

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