JPH07165697A - Semiconductor compound and pest-controlling agent - Google Patents

Semiconductor compound and pest-controlling agent

Info

Publication number
JPH07165697A
JPH07165697A JP6240049A JP24004994A JPH07165697A JP H07165697 A JPH07165697 A JP H07165697A JP 6240049 A JP6240049 A JP 6240049A JP 24004994 A JP24004994 A JP 24004994A JP H07165697 A JPH07165697 A JP H07165697A
Authority
JP
Japan
Prior art keywords
hhho
group
ocf
ochf
oso
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
JP6240049A
Other languages
Japanese (ja)
Inventor
Shigeru Ishii
茂 石井
Kazuo Yagi
和生 八木
Osamu Otsu
督 大津
Akira Numata
昭 沼田
Tomoyuki Ogura
友幸 小倉
Toshiro Miyake
敏郎 三宅
Akihiko Fujita
明彦 藤田
Norihiko Mimori
紀彦 三森
Shinji Takii
新自 瀧井
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 JP6240049A priority Critical patent/JPH07165697A/en
Priority to AU20847/95A priority patent/AU2084795A/en
Priority to TW84103138A priority patent/TW299314B/zh
Priority to PCT/JP1995/000623 priority patent/WO1996010560A1/en
Priority to IL11322995A priority patent/IL113229A0/en
Publication of JPH07165697A publication Critical patent/JPH07165697A/en
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
    • C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
    • C07C281/14—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being further bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms

Abstract

PURPOSE:To obtain a new compound capable of effectively controlling insect pests of Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Isoptera, and Acarina and Anoplura and hardly having undesirable influence on mammal, fishes and beneficial insects. CONSTITUTION:A compound of formula I [W is 0 or S; X, Y and Z are Cl, Br, OH, cyano, etc.; R<1> to R<4> each is H, a 1-6C alkyl; (1) and (m) are each an integer of 0-5; (n) is an integer of 1-5], e.g. N(4-chlorophenyl)-4- chlorobenzamide-4trifluoromethoxysemicarbazone. For example, this compound is obtained by reacting a compound of formula II with phosphorus pentachloride without using a solvent to afford a compound of formula III, reacting the compound of formula III with a compound of formula IV in an inert solvent to give a compound of formula V and further reacting the compound of formula V with a compound of the formula R<2>L<1> (L<1> is a halogen or an alkylsulfonate) in the presence of a base in an inert solvent.

Description

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

【０００１】[0001]

【産業上の利用分野】本発明は新規なセミカルバゾン化
合物ならびに該化合物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 semicarbazone compound and a pest control agent containing the compound as an active ingredient.

【０００２】[0002]

【従来の技術】従来、ベンズアミドのセミカルバゾン化
合物に関してはヨーロピアン・ジャーナル・オブ・メデ
ィシナル・ケミストリー〔Ｅｕｒ．Ｊ．Ｍｅｄ．Ｃｈｅ
ｍ．，２６，２７３（１９９１）〕に４−ＲＣ6Ｈ4Ｃ＝
（ＮＨＣ6Ｈ4Ｒ′−４）ＮＮＨＣＷＮＨＲ″（ただしＲ
＝Ｈ，ＭｅＯ，Ｍｅ，Ｃｌ，ＮＯ2 ；Ｒ′＝Ｈ，Ｍｅ
Ｏ，Ｍｅ，Ｃｌ；Ｒ″＝Ｐｈ；Ｗ＝Ｏ，Ｓ）である化合
物が知られているが、Ｒ″は無置換のフェニルのみで、
置換フェニルは新規である。また、この文献には医薬と
しての活性は示されているが、有害生物に対する活性は
何ら開示されていない。2. Description of the Related Art Conventionally, regarding the semicarbazone compounds of benzamide, European Journal of Medicinal Chemistry [Eur. J. Med. Che
m. , 26 , 273 (1991)] 4-RC 6 H 4 C =
(NHC 6 H 4 R'-4) NNHCWNHR "(where R
= H, MeO, Me, Cl , NO 2; R '= H, Me
O, Me, Cl; R ″ = Ph; W = O, S) are known, but R ″ is only unsubstituted phenyl,
Substituted phenyl is new. Further, although this document shows activity as a medicine, it does not disclose any activity against pests.

【０００３】[0003]

【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 perturbing the ecosystem due to persistence. Therefore, the development of new insecticides with low toxicity and low residue is always expected.

【０００４】本発明者らはセミカルバゾン化合物につい
て鋭意研究を重ねた結果、新規なベンズアニドのセミカ
ルバゾン化合物が低薬量で優れた殺虫活性を示し、かつ
ホ乳動物、魚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。As a result of intensive studies on the semicarbazone compound, the present inventors have found that the novel benzanid semicarbazone compound exhibits excellent insecticidal activity at a low dose and has almost no adverse effect on mammals, fish and beneficial insects. The present invention has been completed by discovering that the compound is a very useful compound having no

【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２】 [Chemical 2]

【０００７】〔式中、Ｗは酸素原子またはイオウ原子を
示し、Ｘ、Ｙ、Ｚは各々独立してハロゲン原子、水酸
基、シアノ基、ニトロ基、ＳＣＮ基、トリメチルシリル
基、Ｒ9 、ＯＲ9、Ｓ（Ｏ）pＲ9基、ＯＳ（Ｏ）2Ｒ
9基、ＯＣ（Ｏ）Ｒ9基、Ｃ（Ｏ）Ｒ9基、ＣＯ2Ｒ9基、
Ｃ（Ｏ）Ｎ（Ｒ9）Ｒ10基、ＳＯ2Ｎ（Ｒ9）Ｒ10基、Ｎ
ＨＣ（Ｏ）Ｒ9基、Ｎ（Ｒ9）Ｒ10基、隣あった炭素原子
間で形成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ
2Ｏ−基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−
ＯＣＦ2ＣＦ2Ｏ−基または−ＯＣＦ2ＣＦ2−基を示し、
Ｒ1は水素原子、Ｒ5、Ｒ5によって置換されていてもよ
いＣ1〜Ｃ6アルキル基または（Ｒ5）qによって置換され
ていてもよいフェニル基を示し、Ｒ2、Ｒ3、Ｒ4は各々
独立して水素原子、Ｃ1〜Ｃ6アルキル基、Ｃ2〜Ｃ6アル
ケニル基、Ｃ2〜Ｃ6アルキニル基、Ｃ1〜Ｃ6ハロアルキ
ル基、Ｃ2〜Ｃ6アルコキシアルキル基、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、Ｃ
2〜Ｃ6ハロアルキルカルボニル基、Ｃ1〜Ｃ6アルキルチ
オ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｒ6ＯＣ（Ｏ）Ｎ
（Ｒ7）Ｓ−基、Ｒ7（Ｒ8）ＮＳ−基または（Ｒ5）qに
よって置換されていてもよいベンジル基を示し、Ｒ5は
ハロゲン原子、水酸基、シアノ基、ニトロ基、Ｃ1〜Ｃ6
アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコ
キシ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6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アルコキシカルボニル基、アミノ基またはジＣ
1〜Ｃ6アルキルアミノ基を示し、Ｒ6、Ｒ7、Ｒ8は各々
独立してＣ1〜Ｃ6アルキル基、（Ｒ5）qによって置換さ
れていてもよいフェニル基または（Ｒ5）qによって置換
されていてもよいベンジル基を示し、Ｒ9はＣ1〜Ｃ6ア
ルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルケニ
ル基、Ｃ2〜Ｃ6ハロアルケニル基、Ｃ2〜Ｃ6アルキニル
基、Ｃ2〜Ｃ6ハロアルキニル基、Ｃ3〜Ｃ6シクロアルキ
ル基、Ｃ3〜Ｃ6ハロシクロアルキル基、Ｃ4〜Ｃ7シクロ
アルキルアルキル基、Ｃ2〜Ｃ6アルコキシアルキル基、
Ｃ2〜Ｃ6アルキルチオアルキル基、Ｃ2〜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、
（Ｒ5）qによって置換されていてもよいフェニル基、
（Ｒ5）qによって置換されていてもよいベンジル基また
は（Ｒ5）rによって置換されていてもよいピリジル基を
示し、Ｒ10は水素原子またはＣ1〜Ｃ6アルキル基を示
し、ｋは０〜２の整数を示し、ｌは０〜５の整数（ただ
し、ｌが２〜５の場合Ｘは同一であっても異なっていて
もよい）を示し、ｍは０〜５の整数（ただし、ｍが２〜
５の場合Ｙは同一であっても異なっていてもよい）を示
し、ｎは１〜５の整数（ただし、ｎが２〜５の場合Ｚは
同一であっても異なっていてもよい）を示し、ｐは０〜
２の整数を示し、ｑは０〜５の整数（ただし、ｑが２〜
５の場合Ｒ5は同一であっても異なっていてもよい）を
示し、ｒは０〜４の整数（ただし、ｒが２〜４の場合Ｒ
5は同一であっても異なっていてもよい）を示す。〕で
表わされるセミカルバゾン化合物及び該化合物の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。[In the formula, W represents an oxygen atom or a sulfur atom, and X, Y, and Z are each independently a halogen atom, a hydroxyl group, a cyano group, a nitro group, an SCN group, a trimethylsilyl group, R 9 , OR 9 , S (O) p R 9 group, OS (O) 2 R
9 groups, OC (O) R 9 groups, C (O) R 9 groups, CO 2 R 9 groups,
C (O) N (R 9 ) R 10 group, SO 2 N (R 9 ) R 10 group, N
HC (O) R 9 group, N (R 9 ) R 10 group, -CH = CH-CH = CH- group formed between adjacent carbon atoms, -OCH
2 O- group, -OCH 2 CH 2 O- group, -OCF 2 O- group,-
OCF 2 CF 2 O- group or -OCF 2 CF 2 - represents a group,
R 1 represents a hydrogen atom, a C 1 -C 6 alkyl group optionally substituted by R 5 , R 5 or a phenyl group optionally substituted by (R 5 ) q , and R 2 , R 3 , R 4 are each independently a hydrogen 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 1 to C 6 haloalkyl group, a C 2 to C 6 alkoxyalkyl group, C 2 -C 6 alkylcarbonyl groups, C 2 -C 6 alkoxycarbonyl groups, C
2 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, R 6 OC (O) N
(R 7 ) S-group, R 7 (R 8 ) NS-group or a benzyl group which may be substituted by (R 5 ) q , wherein R 5 is a halogen atom, a hydroxyl group, a cyano group, a nitro group or C 1 ~ C 6
Alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 An alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group,
C 2 -C 6 alkoxycarbonyl group, an amino group or a di C
1 to C 6 alkylamino group is shown, and R 6 , R 7 and R 8 are each independently a C 1 to C 6 alkyl group, a phenyl group optionally substituted by (R 5 ) q or (R 5 ) represents a benzyl group optionally substituted by q , R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 4 -C 7 cycloalkylalkyl, C 2 -C 6 An alkoxyalkyl group,
C 2 -C 6 alkylthioalkyl group, C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 cyanoalkyl radical,
(R 5 ) a phenyl group optionally substituted by q ,
(R 5 ) represents a benzyl group optionally substituted by q or a pyridyl group optionally substituted by (R 5 ) r , R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, and k represents Represents an integer of 0 to 2, l represents an integer of 0 to 5 (provided that when 1 is 2 to 5, X may be the same or different), and m represents an integer of 0 to 5 (however. , M is 2
In the case of 5, Y may be the same or different, and n is an integer of 1 to 5 (provided that when n is 2 to 5, Z may be the same or different). , P is 0
2 indicates an integer of 2 and q is an integer of 0 to 5 (however, q is 2 to
In the case of 5, R 5 may be the same or different, and r is an integer of 0 to 4 (provided that r is 2 to 4 R
5 may be the same or different). ] It is related with the semicarbazone compound represented by these, and the pest control agent which contains 1 type (s) or 2 or more types of this compound as an active ingredient.

【０００８】本明細書において示した各置換基の例を以
下に示す。なお、各置換基のうち炭素鎖は、直鎖、分岐
鎖または環状の何れでもよい。以下、ｎ−はノルマル、
ｉ−はイソ、ｓｅｃ−はセカンダリー、ｔ−はターシャ
リー、ｃ−はシクロを意味する。Examples of each substituent shown in the present specification are shown below. The carbon chain of each substituent may be linear, branched or cyclic. Hereinafter, n- is normal,
i- means iso, sec- means secondary, t- means tertiary, and c- means cyclo.

【０００９】Ｃ1〜Ｃ6アルキル基としては、メチル基、
エチル基、ｎ−プロピル基、ｉ−プロピル基、ｃ−プロ
ピル基、ｎ−ブチル基、ｉ−ブチル基、ｓｅｃ−ブチル
基、ｔ−ブチル基、ｃ−ブチル基、ｎ−ペンチル基、ｃ
−ペンチル基、ｎ−ヘキシル基、ｃ−ヘキシル基等が挙
げられる。As the C 1 -C 6 alkyl group, a methyl group,
Ethyl group, n-propyl group, i-propyl group, c-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, c-butyl group, n-pentyl group, c
-Pentyl group, n-hexyl group, c-hexyl group and the like.

【００１０】Ｃ2〜Ｃ6アルケニル基としては、エテニル
基、２−プロペニル基、２−メチル−２−プロペニル
基、２−ブテニル基等が挙げられる。Examples of the C 2 -C 6 alkenyl group include ethenyl group, 2-propenyl group, 2-methyl-2-propenyl group and 2-butenyl group.

【００１１】Ｃ2〜Ｃ6アルキニル基としては、エチニル
基、２−プロピニル基、２−ブチニル基等が挙げられ
る。Examples of the C 2 -C 6 alkynyl group include ethynyl group, 2-propynyl group and 2-butynyl group.

【００１２】Ｃ2〜Ｃ6アルコキシアルキル基としては、
メトキシメチル基、エトキシメチル基、１−メトキシエ
チル基等が挙げられる。As the C 2 -C 6 alkoxyalkyl group,
Examples thereof include a methoxymethyl group, an ethoxymethyl group and a 1-methoxyethyl group.

【００１３】Ｃ2〜Ｃ6アルキルカルボニル基としては、
メチルカルボニル基、エチルカルボニル基、ｎ−プロピ
ルカルボニル基、ｉ−プロピルカルボニル基、ｃ−プロ
ピルカルボニル基、ｎ−ブチルカルボニル基、ｉ−ブチ
ルカルボニル基、ｓｅｃ−ブチルカルボニル基、ｔ−ブ
チルカルボニル基、ｃ−ブチルカルボニル基等が挙げら
れる。As the C 2 -C 6 alkylcarbonyl group,
Methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, c-propylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, sec-butylcarbonyl group, t-butylcarbonyl group, Examples thereof include c-butylcarbonyl group.

【００１４】Ｃ2〜Ｃ6アルコキシカルボニル基として
は、メトキシカルボニル基、エトキシカルボニル基、ｎ
−プロポキシカルボニル基、ｉ−プロポキシカルボニル
基、ｃ−プロポキシカルボニル基、ｎ−ブトキシカルボ
ニル基、ｉ−ブトキシカルボニル基、ｓｅｃ−ブトキシ
カルボニル基、ｔ−ブトキシカルボニル基、ｃ−ブトキ
シカルボニル基等が挙げられる。The C 2 -C 6 alkoxycarbonyl group includes methoxycarbonyl group, ethoxycarbonyl group, n
-Propoxycarbonyl group, i-propoxycarbonyl group, c-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, t-butoxycarbonyl group, c-butoxycarbonyl group and the like. .

【００１５】ハロゲン原子としては、フッ素原子、塩素
原子、臭素原子、ヨウ素原子が挙げられる。Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

【００１６】Ｗとしては酸素原子とイオウ原子が挙げら
れるが、好ましくは酸素原子が挙げられる。Examples of W include an oxygen atom and a sulfur atom, preferably an oxygen atom.

【００１７】Ｘ、Ｙ、Ｚとしては各々独立してハロゲン
原子、水酸基、シアノ基、ニトロ基、ＳＣＮ基、トリメ
チルシリル基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアル
キル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6ハロアルケニ
ル基、Ｃ2〜Ｃ6アルキニル基、Ｃ2〜Ｃ6ハロアルキニル
基、Ｃ3〜Ｃ6シクロアルキル基、Ｃ3〜Ｃ6ハロシクロア
ルキル基、Ｃ4〜Ｃ7シクロアルキルアルキル基、Ｃ2〜
Ｃ6アルコキシアルキル基、Ｃ2〜Ｃ6アルキルチオアル
キル基、Ｃ2〜Ｃ6アルコキシカルボニルアルキル基、Ｃ
2〜Ｃ6シアノアルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1
〜Ｃ6ハロアルコキシ基、Ｃ2〜Ｃ6アルケニルオキシ
基、Ｃ2〜Ｃ6ハロアルケニルオキシ基、Ｃ2〜Ｃ6アルキ
ニルオキシ基、Ｃ2〜Ｃ6ハロアルキニルオキシ基、Ｃ3
〜Ｃ6シクロアルキルオキシ基、Ｃ3〜Ｃ6ハロシクロア
ルキルオキシ基、Ｃ4〜Ｃ7シクロアルキルアルキルオキ
シ基、Ｃ2〜Ｃ6アルコキシアルキルオキシ基、Ｃ2〜Ｃ6
アルキルチオアルキルオキシ基、Ｃ3〜Ｃ6アルコキシカ
ルボニルアルキルオキシ基、Ｃ2〜Ｃ6シアノアルキルオ
キシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキ
ルチオ基、Ｃ2〜Ｃ6アルケニルチオ基、Ｃ2〜Ｃ6ハロア
ルケニルチオ基、Ｃ2〜Ｃ6アルキニルチオ基、Ｃ2〜Ｃ6
ハロアルキニルチオ基、Ｃ3〜Ｃ6シクロアルキルチオ
基、Ｃ3〜Ｃ6ハロシクロアルキルチオ基、Ｃ4〜Ｃ7シク
ロアルキルアルキルチオ基、Ｃ2〜Ｃ6アルコキシアルキ
ルチオ基、Ｃ2〜Ｃ6アルキルチオアルキルチオ基、Ｃ2
〜Ｃ6アルコキシカルボニルアルキルチオ基、Ｃ2〜Ｃ6
シアノアルキルチオ基、Ｃ1〜Ｃ6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、Ｃ2〜Ｃ6ア
ルケニルスルフィニル基、Ｃ2〜Ｃ6ハロアルケニルスル
フィニル基、Ｃ2〜Ｃ6アルキニルスルフィニル基、Ｃ2
〜Ｃ6ハロ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、Ｃ3〜Ｃ6ハロシクロアルキル
スルフィニル基、Ｃ4〜Ｃ7シクロアルキルアルキルスル
フィニル基、Ｃ2〜Ｃ6アルコキシアルキルスルフィニル
基、Ｃ2〜Ｃ6アルキルチオアルキルスルフィニル基、Ｃ
1〜Ｃ6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アルケニルスルホニル基、Ｃ2〜
Ｃ6ハロアルケニルスルホニル基、Ｃ2〜Ｃ6アルキニル
スルホニル基、Ｃ2〜Ｃ6ハロ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、Ｃ3〜Ｃ6ハロシ
クロアルキルスルホニル基、Ｃ4〜Ｃ7シクロアルキルア
ルキルスルホニル基、Ｃ2〜Ｃ6アルコキシアルキルスル
ホニル基、Ｃ2〜Ｃ6アルキルチオアルキルスルホニル
基、Ｃ2〜Ｃ6アルコキシカルボニルアルキルスルホニル
基、Ｃ2〜Ｃ6シアノアルキルスルホニル基、Ｃ1〜Ｃ6ア
ルキルスルホニルオキシ基、Ｃ1〜Ｃ6ハロアルキルスル
ホニルオキシ基、Ｃ3〜Ｃ6シクロアルキルスルホニルオ
キシ基、Ｃ3〜Ｃ6ハロシクロアルキルスルホニルオキシ
基、Ｃ2〜Ｃ6シアノアルキルスルホニルオキシ基、Ｃ2
〜Ｃ7アルキルカルボニルオキシ基、Ｃ2〜Ｃ7ハロアル
キルカルボニルオキシ基、Ｃ4〜Ｃ7シクロアルキルカル
ボニルオキシ基、Ｃ4〜Ｃ7ハロシクロアルキルカルボニ
ルオキシ基、Ｃ 3〜Ｃ7シアノアルキルカルボニルオキシ
基、Ｃ2〜Ｃ7アルキルカルボニル基、Ｃ 2〜Ｃ7ハロアル
キルカルボニル基、Ｃ4〜Ｃ7シクロアルキルカルボニル
基、Ｃ4〜Ｃ7ハロシクロアルキルカルボニル基、Ｃ3〜
Ｃ7シアノアルキルカルボニル基、Ｃ2〜Ｃ7アルコキシ
カルボニル基、Ｃ2〜Ｃ7ハロアルコキシカルボニル基、
Ｃ 4〜Ｃ7シクロアルキルオキシカルボニル基、Ｃ4〜Ｃ7
ハロシクロアルキルオキシカルボニル基、Ｃ3〜Ｃ7シア
ノアルキルオキシカルボニル基、モノＣ1〜Ｃ6アルキル
アミノカルボニル基、モノＣ1〜Ｃ6ハロアルキルアミノ
カルボニル基、ジＣ 1〜Ｃ6アルキルアミノカルボニル
基、ジＣ1〜Ｃ6ハロアルキルアミノカルボニル基、モノ
Ｃ1〜Ｃ6アルキルアミノスルホニル基、モノＣ1〜Ｃ6ハ
ロアルキルアミノスルホニル基、ジＣ1〜Ｃ6アルキルア
ミノスルホニル基、ジＣ1〜Ｃ6ハロアルキルアミノスル
ホニル基、アミノカルボニル基、アミノスルホニル基、
ホルミルアミノ基、Ｃ2〜Ｃ7アルキルカルボニルアミノ
基、Ｃ2〜Ｃ7ハロアルキルカルボニルアミノ基、アミノ
基、モノＣ1〜Ｃ6アルキルアミノ基、モノＣ1〜Ｃ6ハロ
アルキルアミノ基、ジＣ1〜Ｃ6アルキルアミノ基、ジＣ
1〜Ｃ6ハロアルキルアミノ基、隣あった炭素原子間で形
成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ2Ｏ−
基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−ＯＣ
Ｆ2ＣＦ2Ｏ−基、−ＯＣＦ2ＣＦ2−基、置換されていて
もよいフェニル基、置換されていてもよいフェノキシ
基、置換されていてもよいフェニルチオ基、置換されて
いてもよいフェニルスルフィニル基、置換されていても
よいフェニルスルホニル基、置換されていてもよいフェ
ニルスルホニルオキシ基、置換されていてもよいフェニ
ルカルボニルオキシ基、置換されていてもよいフェニル
カルボニル基、置換されていてもよいフェノキシカルボ
ニル基、置換されていてもよいフェニルアミノカルボニ
ル基、置換されていてもよいフェニルスルホニルアミノ
基、置換されていてもよいフェニルカルボニルアミノ
基、置換されていてもよいフェニルアミノ基、置換され
ていてもよいベンジル基、置換されていてもよいベンジ
ルオキシ基、置換されていてもよいベンジルチオ基、置
換されていてもよいベンジルスルフィニル基、置換され
ていてもよいベンジルスルホニル基、置換されていても
よいベンジルスルホニルオキシ基、置換されていてもよ
いベンジルカルボニルオキシ基、置換されていてもよい
ベンジルカルボニル基、置換されていてもよいベンジル
オキシカルボニル基、置換されていてもよいベンジルア
ミノカルボニル基、置換されていてもよいベンジルスル
ホニルアミノ基、置換されていてもよいベンジルカルボ
ニルアミノ基、置換されていてもよいベンジルアミノ
基、置換されていてもよいピリジル基、置換されていて
もよいピリジルオキシ基、置換されていてもよいピリジ
ルチオ基、置換されていてもよいピリジルスルフィニル
基、置換されていてもよいピリジルスルホニル基、置換
されていてもよいピリジルスルホニルオキシ基、置換さ
れていてもよいピリジルカルボニルオキシ基、置換され
ていてもよいピリジルカルボニル基、置換されていても
よいピリジルオキシカルボニル基、置換されていてもよ
いピリジルアミノカルボニル基、置換されていてもよい
ピリジルスルホニルアミノ基、置換されていてもよいピ
リジルカルボニルアミノ基または置換されていてもよい
ピリジルアミノ基（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、水酸基、シアノ基、ニトロ
基、Ｃ1〜Ｃ6アルキル基、Ｃ 1〜Ｃ6ハロアルキル基、Ｃ
1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチオ基、
Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキル
スルホニル基、Ｃ1〜Ｃ6アルコキシカルボニル基、アミ
ノ基またはジＣ1〜Ｃ6アルキルアミノ基が挙げられ
る。）が挙げられる。X, Y and Z are each independently halogen.
Atom, hydroxyl group, cyano group, nitro group, SCN group, trime
Cylsilyl group, C1~ C6Alkyl group, C1~ C6Halo al
Kill group, C2~ C6Alkenyl group, C2~ C6Halo archeni
Lu group, C2~ C6Alkynyl group, C2~ C6Haloalkynyl
Base, C3~ C6Cycloalkyl group, C3~ C6Halo cycloa
Rukiru group, CFour~ C7Cycloalkylalkyl group, C2~
C6Alkoxyalkyl group, C2~ C6Alkyl thioal
Kill group, C2~ C6Alkoxycarbonylalkyl group, C
2~ C6Cyanoalkyl group, C1~ C6Alkoxy group, C1
~ C6Haloalkoxy group, C2~ C6Alkenyloxy
Base, C2~ C6Haloalkenyloxy group, C2~ C6Archi
Nyloxy group, C2~ C6Haloalkynyloxy group, C3
~ C6Cycloalkyloxy group, C3~ C6Halo cycloa
Rualkyloxy group, CFour~ C7Cycloalkyl alkyl oki
Shi group, C2~ C6Alkoxyalkyloxy group, C2~ C6
Alkylthioalkyloxy group, C3~ C6Alkoxyca
Rubonylalkyloxy group, C2~ C6Cyanoalkyl
Xy group, C1~ C6Alkylthio group, C1~ C6Halo Archi
Ruthio group, C2~ C6Alkenylthio group, C2~ C6Haloa
Lucenylthio group, C2~ C6Alkynylthio group, C2~ C6
Haloalkynylthio group, C3~ C6Cycloalkylthio
Base, C3~ C6Halocycloalkylthio group, CFour~ C7Shiku
Roalkylalkylthio group, C2~ C6Alkoxy alk
Ruthio group, C2~ C6Alkylthio alkylthio group, C2
~ C6Alkoxycarbonylalkylthio group, C2~ C6
Cyanoalkylthio group, C1~ C6Alkylsulfinyl
Base, C1~ C6Haloalkylsulfinyl group, C2~ C6A
Lucenylsulfinyl group, C2~ C6Haloalkenyl sul
Finyl group, C2~ C6Alkynylsulfinyl group, C2
~ C6Haloalkynylsulfinyl group, C3~ C6Cyclo
Alkylsulfinyl group, C3~ C6Halocycloalkyl
Sulfinyl group, CFour~ C7Cycloalkyl alkyl sul
Finyl group, C2~ C6Alkoxyalkyl sulfinyl
Base, C2~ C6Alkylthioalkylsulfinyl group, C
1~ C6Alkylsulfonyl group, C1~ C6Haloalkyls
Ruphonyl group, C2~ C6Alkenylsulfonyl group, C2~
C6Haloalkenylsulfonyl group, C2~ C6Alkynyl
Sulfonyl group, C2~ C6A haloalkynylsulfonyl group,
C3~ C6Cycloalkylsulfonyl group, C3~ C6Haroshi
Chloroalkylsulfonyl group, CFour~ C7Cycloalkyl
Rukylsulphonyl group, C2~ C6Alkoxyalkyl sulphate
Honyl group, C2~ C6Alkylthioalkylsulfonyl
Base, C2~ C6Alkoxycarbonylalkylsulfonyl
Base, C2~ C6Cyanoalkylsulfonyl group, C1~ C6A
Rukylsulphonyloxy group, C1~ C6Haloalkyl sul
Honyloxy group, C3~ C6Cycloalkylsulfonyl
Xy group, C3~ C6Halocycloalkylsulfonyloxy
Base, C2~ C6Cyanoalkylsulfonyloxy group, C2
~ C7Alkylcarbonyloxy group, C2~ C7Halo al
Killcarbonyloxy group, CFour~ C7Cycloalkylcal
Bonyloxy group, CFour~ C7Halocycloalkylcarboni
Luoxy group, C 3~ C7Cyanoalkylcarbonyloxy
Base, C2~ C7Alkylcarbonyl group, C 2~ C7Halo al
Killcarbonyl group, CFour~ C7Cycloalkyl carbonyl
Base, CFour~ C7Halocycloalkylcarbonyl group, C3~
C7Cyanoalkylcarbonyl group, C2~ C7Alkoxy
Carbonyl group, C2~ C7A haloalkoxycarbonyl group,
C Four~ C7Cycloalkyloxycarbonyl group, CFour~ C7
Halocycloalkyloxycarbonyl group, C3~ C7Shea
Noalkyloxycarbonyl group, Mono C1~ C6Alkyl
Aminocarbonyl group, Mono C1~ C6Haloalkylamino
Carbonyl group, di-C 1~ C6Alkylaminocarbonyl
Group, di-C1~ C6Haloalkylaminocarbonyl group, mono
C1~ C6Alkylaminosulfonyl group, Mono C1~ C6Ha
Roalkylaminosulfonyl group, di-C1~ C6Alkyla
Minosulfonyl group, di-C1~ C6Haloalkylaminosul
Sulfonyl group, aminocarbonyl group, aminosulfonyl group,
Formylamino group, C2~ C7Alkylcarbonylamino
Base, C2~ C7Haloalkylcarbonylamino group, amino
Group, Mono C1~ C6Alkylamino group, Mono C1~ C6Halo
Alkylamino group, di-C1~ C6Alkylamino group, di-C
1~ C6Haloalkylamino group, formed between adjacent carbon atoms
Formed -CH = CH-CH = CH- group, -OCH2O-
Group, -OCH2CH2O-group, -OCF2O-group, -OC
F2CF2O-group, -OCF2CF2-Group, substituted
Optionally phenyl group, optionally substituted phenoxy
Group, optionally substituted phenylthio group, substituted
Phenylsulfinyl group which may be present, which may be substituted
Good phenylsulfonyl group, optionally substituted phenyl
Nylsulfonyloxy group, optionally substituted phenyl
Lucarbonyloxy group, optionally substituted phenyl
Carbonyl group, optionally substituted phenoxycarbo
Nyl group, optionally substituted phenylaminocarbonyl
Group, optionally substituted phenylsulfonylamino
Group, optionally substituted phenylcarbonylamino
Group, optionally substituted phenylamino group, substituted
Optionally substituted benzyl group, optionally substituted benzyl
Ruoxy group, optionally substituted benzylthio group,
Optionally substituted benzylsulfinyl group, substituted
Optionally substituted benzylsulfonyl group, optionally substituted
Good benzylsulfonyloxy group, optionally substituted
A benzylcarbonyloxy group, which may be substituted
Benzylcarbonyl group, optionally substituted benzyl
Oxycarbonyl group, optionally substituted benzyl group
Minocarbonyl group, optionally substituted benzylsul
Fonylamino group, optionally substituted benzylcarbo
Nylamino group, optionally substituted benzylamino
Group, optionally substituted pyridyl group, optionally substituted
Optionally pyridyloxy group, optionally substituted pyridi
Ruthio group, optionally substituted pyridylsulfinyl
Group, optionally substituted pyridylsulfonyl group, substituted
Optionally substituted pyridylsulfonyloxy group, substituted
Optionally substituted pyridylcarbonyloxy group, substituted
Optionally substituted pyridylcarbonyl group, optionally substituted
Good pyridyloxycarbonyl group, which may be substituted
A pyridylaminocarbonyl group, which may be substituted
Pyridylsulfonylamino group, optionally substituted
Lysylcarbonylamino group or optionally substituted
Pyridylamino group (provided that it may be substituted
As a halogen atom, hydroxyl group, cyano group, nitro
Base, C1~ C6Alkyl group, C 1~ C6Haloalkyl group, C
1~ C6Alkylthio group, C1~ C6A haloalkylthio group,
C1~ C6Alkylsulfonyl group, C1~ C6Haloalkyl
Sulfonyl group, C1~ C6Alkoxycarbonyl group, ami
Group or di-C1~ C6Alkylamino groups include
It ) Is mentioned.

【００１８】Ｘとして好ましくは、ハロゲン原子、Ｃ1
〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6
ハロアルコキシ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1
〜Ｃ6ハロアルキルスルホニルオキシ基が挙げられる。X is preferably a halogen atom or C 1
To C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6
Haloalkoxy group, C 1 to C 6 haloalkylthio group, C 1
To C 6 haloalkylsulfonyloxy groups.

【００１９】Ｙとして好ましくは、ハロゲン原子、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロア
ルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアルコ
キシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキ
ルチオ基、Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハ
ロアルキルスルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホ
ニルオキシ基、隣あった炭素原子間で形成する−ＯＣＦ
2Ｏ−基または−ＯＣＦ2ＣＦ2Ｏ−基が挙げられる。Y is preferably a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, the adjoining carbon atoms Formed between -OCF
2 O- group or -OCF 2 CF 2 O- group.

【００２０】Ｚとして好ましくは、ハロゲン原子、シア
ノ基、ニトロ基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6ハ
ロアルコキシ基、Ｃ1〜Ｃ6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、
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、Ｃ1〜Ｃ6ハロアルキルスルホニル基、
Ｃ1〜Ｃ6アルキルスルホニルオキシ基、Ｃ1〜Ｃ6ハロア
ルキルスルホニルオキシ基、隣あった炭素原子間で形成
する−ＯＣＦ2Ｏ−基、−ＯＣＦ2ＣＦ2Ｏ−基または−
ＯＣＦ2ＣＦ2−基が挙げられる。Z is preferably a halogen atom, a cyano group, a nitro group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 haloalkoxy group, a C 1 -C 6 alkylthio group or a C 1 -C 6 haloalkylthio group. A C 1 -C 6 alkylsulfinyl group,
A C 1 -C 6 haloalkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group,
C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 haloalkylsulfonyl group, next there was -OCF 2 O-group formed between carbon atoms, -OCF 2 CF 2 O- group or a -
OCF 2 CF 2 - group.

【００２１】Ｒ1としては、ハロゲン原子、水酸基、シ
アノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロ
アルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアル
コキシ基、Ｃ1〜Ｃ6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アルコキシカルボ
ニル基、アミノ基、ジＣ1〜Ｃ6アルキルアミノ基または
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、水酸基、シ
アノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロ
アルキル基、Ｃ 1〜Ｃ6アルコキシ基、Ｃ1〜Ｃ6ハロアル
コキシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ 1〜Ｃ6ハロアル
キルチオ基、Ｃ1〜Ｃ6アルキルスルホニル基、Ｃ2〜Ｃ6
アルコキシカルボニル基、アミノ基またはジＣ1〜Ｃ6ア
ルキルアミノ基が挙げられる）が挙げられる。R1Is a halogen atom, hydroxyl group,
Ano group, nitro group, C1~ C6Alkyl group, C1~ C6Halo
Alkyl group, C1~ C6Alkoxy group, C1~ C6Halo al
Coxy group, C1~ C6Alkylthio group, C1~ C6Halo al
Kirthio group, C1~ C6Alkylsulfonyl group, C1~ C6
Haloalkylsulfonyl group, C2~ C6Alkoxy carbo
Nyl group, amino group, di-C1~ C6Alkylamino group or
An optionally substituted phenyl group (provided that it is substituted
The substituents that may be present include halogen atoms, hydroxyl groups, and
Ano group, nitro group, C1~ C6Alkyl group, C1~ C6Halo
Alkyl group, C 1~ C6Alkoxy group, C1~ C6Halo al
Coxy group, C1~ C6Alkylthio group, C 1~ C6Halo al
Kirthio group, C1~ C6Alkylsulfonyl group, C2~ C6
Alkoxycarbonyl group, amino group or di-C1~ C6A
Includes a rualkylamino group).

【００２２】Ｒ1として好ましくは、水素原子またはＣ1
〜Ｃ6アルキル基が挙げられる。R 1 is preferably a hydrogen atom or C 1
To C 6 alkyl groups.

【００２３】Ｒ2、Ｒ3及びＲ4としては、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、Ｃ1〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルコ
キシアルキル基、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、Ｃ2〜Ｃ6ハロアルキル
カルボニル基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロ
アルキルチオ基、Ｃ2〜Ｃ12ジアルキルアミノチオ基、
Ｃ3〜Ｃ12（アルキル）アルコキシカルボニルアミノチ
オ基または置換されていてもよいベンジル基（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、
水酸基、シアノ基、ニトロ基、Ｃ1〜Ｃ6アルキル基、Ｃ
1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキシ基、Ｃ1〜
Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜
Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキルスルホニル
基、Ｃ2〜Ｃ6アルコキシカルボニル基、アミノ基または
ジＣ1〜Ｃ6アルキルアミノ基が挙げられる）が挙げられ
る。R 2 , R 3 and R 4 are a hydrogen atom, C 1
-C 6 alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, C 1 -C 6 haloalkyl group, C 2 -C 6 alkoxyalkyl group, C 2 -C 6 alkylcarbonyl group, C 2
To C 6 alkoxycarbonyl group, C 2 to C 6 haloalkylcarbonyl group, C 1 to C 6 alkylthio group, C 1 to C 6 haloalkylthio group, C 2 to C 12 dialkylaminothio group,
A C 3 -C 12 (alkyl) alkoxycarbonylaminothio group or an optionally substituted benzyl group (provided that
As the substituent which may be substituted, a halogen atom,
Hydroxyl group, cyano group, nitro group, C 1 -C 6 alkyl group, C
1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 ~
C 6 haloalkoxy group, C 1 to C 6 alkylthio group, C 1 to
C 6 haloalkylthio group, C 1 -C 6 alkylsulfonyl group, C 2 -C 6 alkoxycarbonyl group, amino group or di C 1 -C 6 alkylamino group).

【００２４】Ｒ2、Ｒ3及びＲ4として好ましくは、水素
原子またはＣ1〜Ｃ6アルキル基があげられる。R 2 , R 3 and R 4 are preferably a hydrogen atom or a C 1 -C 6 alkyl group.

【００２５】ｌは０〜２の整数が好ましい。L is preferably an integer of 0 to 2.

【００２６】ｍは０〜２の整数が好ましい。M is preferably an integer of 0-2.

【００２７】ｎは１〜３の整数が好ましい。N is preferably an integer of 1 to 3.

【００２８】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
（＋）体及び（−）体が含まれる。更に、立体配置異性
体が存在する場合には、シス体及びトランス体が含まれ
る。又、本発明化合物はＲ2が水素原子の時、下記に示
す互変異性体の存在が考えられるが、それらの構造も包
含する。Among the compounds included in the present invention, the compounds having an asymmetric carbon atom include the optically active compounds (+) and (−). Further, when there are configurational isomers, cis isomers and trans isomers are included. Further, when R 2 is a hydrogen atom, the compound of the present invention may have the following tautomers, and the structures thereof are also included.

【００２９】[0029]

【化３】 [Chemical 3]

【００３０】本発明に包含される化合物としては、具体
的には例えば、第１表の示す化合物が挙げられる。但
し、第１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。Specific examples of the compounds included in the present invention include the compounds shown in Table 1. However, the compounds in Table 1 are for exemplification, and the present invention is not limited to these.

【００３１】第１表のＱ１〜Ｑ７は次の式で表される基
である。Q1 to Q7 in Table 1 are groups represented by the following formula.

【００３２】[0032]

【化４】 [Chemical 4]

【００３３】第 １ 表Table 1

【００３４】[0034]

【化５】 [Chemical 5]

【００３５】[0035]

【表１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 2-F 0 H H H O 3-F 4-F 3-F 0 H H H O 3-F 4-F 4-F 0 H H H O 3-F 4-F 2-Cl 0 H H H O 3-F 4-F 3-Cl 0 H H H O 3-F 4-F 4-Cl 0 H H H O 3-F 4-F 3-Br 0 H H H O 3-F 4-F 4-Br 0 H H H O 3-F 4-F 4-I 0 H H H O 3-F 4-F 4-CH3 0 H H H O 3-F 4-F 4-CH2CH3 0 H H H O 3-F 4-F 4-CH(CH3)2 0 H H H O 3-F 4-F 4-CH2CH2CH2CH3 0 H H H O 3-F 4-F 4-C(CH3)3 0 H H H O 3-F 4-F 4-CH2CH=CH2 0 H H H O 3-F 4-F 4-C≡CH 0 H H H O 3-F 4-F 4-CH2Ｃ≡CH 0 H H H O 3-F 4-F 4-Q1 0 H H H O 3-F 4-F 4-Q2 0 H H H O 3-F 4-F 4-Q3 0 H H H O 3-F 4-F 4-Q4 0 H H H O 3-F 4-F 4-CHF2 0 H H H O 3-F 4-F 4-CH2Br ───────────────────────────────────[Table 1] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F 0 HHHO 3-F 4-F 3-F 0 HHHO 3-F 4-F 4-F 0 HHHO 3-F 4-F 2-Cl 0 HHHO 3-F 4-F 3-Cl 0 HHHO 3-F 4-F 4-Cl 0 HHHO 3-F 4-F 3-Br 0 HHHO 3-F 4-F 4-Br 0 HHHO 3-F 4-F 4-I 0 HHHO 3-F 4-F 4-CH 3 0 HHHO 3-F 4-F 4-CH 2 CH 3 0 HHHO 3-F 4-F 4-CH (CH 3 ) 20 HHHO 3-F 4-F 4-CH 2 CH 2 CH 2 CH 3 0 HHHO 3- F 4-F 4-C (CH 3 ) 3 0 HHHO 3-F 4-F 4-CH 2 CH = CH 2 0 HHHO 3-F 4-F 4-C ≡ CH 0 HHHO 3-F 4-F 4 -CH 2 C ≡ CH 0 HHHO 3-F 4-F 4-Q1 0 HHHO 3-F 4-F 4-Q2 0 HHHO 3-F 4-F 4-Q3 0 HHHO 3-F 4-F 4-Q4 0 HHHO 3-F 4-F 4-CHF 2 0 HHHO 3-F 4-F 4-CH 2 Br ────────────────────────── ──────────

【００３６】[0036]

【表２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 4-CH2Cl 0 H H H O 3-F 4-F 2-CF3 0 H H H O 3-F 4-F 3-CF3 0 H H H O 3-F 4-F 4-CF3 0 H H H O 3-F 4-F 4-CH2CH=CHCl 0 H H H O 3-F 4-F 4-CH=C(Cl)CF3 0 H H H O 3-F 4-F 4-CH2Ｃ≡CBr 0 H H H O 3-F 4-F 4-(Q4-1-Cl) 0 H H H O 3-F 4-F 4-CH2CN 0 H H H O 3-F 4-F 4-CH2CH(CH3)CN 0 H H H O 3-F 4-F 4-CH2OH 0 H H H O 3-F 4-F 4-CH2CO2H 0 H H H O 3-F 4-F 4-OCH3 0 H H H O 3-F 4-F 4-OCH2CH3 0 H H H O 3-F 4-F 4-OCH(CH3)2 0 H H H O 3-F 4-F 4-OC(CH3)3 0 H H H O 3-F 4-F 4-OCH2CH=CH2 0 H H H O 3-F 4-F 4-OCH2C≡CH 0 H H H O 3-F 4-F 4-O(Q4) 0 H H H O 3-F 4-F 4-OCHF2 0 H H H O 3-F 4-F 4-OCF2Br 0 H H H O 3-F 4-F 2-OCF3 0 H H H O 3-F 4-F 3-OCF3 ───────────────────────────────────[Table 2] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-CH 2 Cl 0 HHHO 3-F 4-F 2-CF 3 0 HHHO 3-F 4-F 3-CF 3 0 HHHO 3-F 4-F 4-CF 3 0 HHHO 3-F 4-F 4-CH 2 CH = CHCl 0 HHHO 3-F 4-F 4-CH = C (Cl) CF 3 0 HHHO 3-F 4-F 4-CH 2 C ≡ CBr 0 HHHO 3-F 4-F 4- (Q4-1-Cl ) 0 HHHO 3-F 4-F 4-CH 2 CN 0 HHHO 3-F 4-F 4-CH 2 CH (CH 3 ) CN 0 HHHO 3-F 4-F 4-CH 2 OH 0 HHHO 3-F 4-F 4-CH 2 CO 2 H 0 HHHO 3-F 4-F 4-OCH 3 0 HHHO 3-F 4-F 4-OCH 2 CH 3 0 HHHO 3-F 4-F 4-OCH (CH 3 ) 2 0 HHHO 3-F 4-F 4-OC (CH 3 ) 3 0 HHHO 3-F 4-F 4-OCH 2 CH = CH 2 0 HHHO 3-F 4-F 4-OCH 2 C ≡ CH 0 HHHO 3-F 4-F 4-O (Q4) 0 HHHO 3-F 4-F 4-OCHF 2 0 HHHO 3-F 4-F 4-OCF 2 Br 0 HHHO 3-F 4-F 2-OCF 3 0 HHHO 3-F 4-F 3-OCF 3 ────────────────────────────────────

【００３７】[0037]

【表３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 4-OCF3 0 H H H O 3-F 4-F 4-OCH2CF3 0 H H H O 3-F 4-F 4-OCF2CF3 0 H H H O 3-F 4-F 4-OCF2CHF2 0 H H H O 3-F 4-F 4-OCF2CHCl2 0 H H H O 3-F 4-F 4-OCF2CHFCl 0 H H H O 3-F 4-F 4-OCF2CHFBr 0 H H H O 3-F 4-F 4-0CF2CF2CF3 0 H H H O 3-F 4-F 4-OCH2CH=CHCl 0 H H H O 3-F 4-F 4-OCH2C≡CBr 0 H H H O 3-F 4-F 4-O(Q4-2,2-Cl2) 0 H H H O 3-F 4-F 4-SCH3 0 H H H O 3-F 4-F 4-SCH2CH=CH2 0 H H H O 3-F 4-F 4-SCH2C≡CH 0 H H H O 3-F 4-F 4-S(Q4) 0 H H H O 3-F 4-F 4-SCHF2 0 H H H O 3-F 4-F 4-SCF2Br 0 H H H O 3-F 4-F 4-SCF3 0 H H H O 3-F 4-F 4-SOCH3 0 H H H O 3-F 4-F 4-SOCH2CH=CH2 0 H H H O 3-F 4-F 4-S0CH2Ｃ≡CH 0 H H H O 3-F 4-F 4-S0(Q4) 0 H H H O 3-F 4-F 4-SOCF3 ───────────────────────────────────[Table 3] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-OCF 3 0 HHHO 3-F 4-F 4-OCH 2 CF 3 0 HHHO 3-F 4-F 4-OCF 2 CF 3 0 HHHO 3-F 4-F 4-OCF 2 CHF 2 0 HHHO 3-F 4-F 4 -OCF 2 CHCl 2 0 HHHO 3-F 4-F 4-OCF 2 CHFCl 0 HHHO 3-F 4-F 4-OCF 2 CHFBr 0 HHHO 3-F 4-F 4-0CF 2 CF 2 CF 3 0 HHHO 3 -F 4-F 4-OCH 2 CH = CHCl 0 HHHO 3-F 4-F 4-OCH 2 C ≡ CBr 0 HHHO 3-F 4-F 4-O (Q4-2,2-Cl 2 ) 0 HHHO 3-F 4-F 4-SCH 30 HHHO 3-F 4-F 4-SCH 2 CH = CH 20 HHHO 3-F 4-F 4-SCH 2 C ≡ CH 0 HHHO 3-F 4-F 4 -S (Q4) 0 HHHO 3-F 4-F 4-SCHF 2 0 HHHO 3-F 4-F 4-SCF 2 Br 0 HHHO 3-F 4-F 4-SCF 3 0 HHHO 3-F 4-F 4-SOCH 3 0 HHHO 3-F 4-F 4-SOCH 2 CH = CH 2 0 HHHO 3-F 4-F 4-S0CH 2 C ≡ CH 0 HHHO 3-F 4-F 4-S0 (Q4) 0 HHHO 3-F 4-F 4-SOCF 3 ────────────────────────────────────

【００３８】[0038]

【表４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 4-SO2CH3 0 H H H O 3-F 4-F 4-SO2CH2CH=CH2 0 H H H O 3-F 4-F 4-S02CH2C≡CH 0 H H H O 3-F 4-F 4-S02(Q4) 0 H H H O 3-F 4-F 4-SO2CF3 0 H H H O 3-F 4-F 4-CH2OCH3 0 H H H O 3-F 4-F 4-OCH2CH2OCH3 0 H H H O 3-F 4-F 4-CH2OCH2CF3 0 H H H O 3-F 4-F 4-OCF2CHFOCF3 0 H H H O 3-F 4-F 4-CH2SCH3 0 H H H O 3-F 4-F 4-OCH2CH2SCH3 0 H H H O 3-F 4-F 4-CH2CO2CH3 0 H H H O 3-F 4-F 4-CH2CO2CH2CF3 0 H H H O 3-F 4-F 4-CH2COCH3 0 H H H O 3-F 4-F 4-OCO2CH3 0 H H H O 3-F 4-F 4-OCOCH3 0 H H H O 3-F 4-F 4-COCH3 0 H H H O 3-F 4-F 4-COCH2CH=CH2 0 H H H O 3-F 4-F 4-C0CH2Ｃ≡CH 0 H H H O 3-F 4-F 4-CO(Q3) 0 H H H O 3-F 4-F 4-COCF3 0 H H H O 3-F 4-F 4-CO2CH2CH3 0 H H H O 3-F 4-F 4-CO2C(CH3)3 ───────────────────────────────────[Table 4] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-SO 2 CH 3 0 HHHO 3-F 4-F 4-SO 2 CH 2 CH = CH 2 0 HHHO 3-F 4-F 4-S0 2 CH 2 C ≡ CH 0 HHHO 3-F 4-F 4-S0 2 (Q4 ) 0 HHHO 3-F 4-F 4-SO 2 CF 3 0 HHHO 3-F 4-F 4-CH 2 OCH 3 0 HHHO 3-F 4-F 4-OCH 2 CH 2 OCH 3 0 HHHO 3-F 4-F 4-CH 2 OCH 2 CF 3 0 HHHO 3-F 4-F 4-OCF 2 CHFOCF 3 0 HHHO 3-F 4-F 4-CH 2 SCH 3 0 HHHO 3-F 4-F 4-OCH 2 CH 2 SCH 3 0 HHHO 3-F 4-F 4-CH 2 CO 2 CH 3 0 HHHO 3-F 4-F 4-CH 2 CO 2 CH 2 CF 3 0 HHHO 3-F 4-F 4-CH 2 COCH 3 0 HHHO 3-F 4-F 4-OCO 2 CH 3 0 HHHO 3-F 4-F 4-OCOCH 3 0 HHHO 3-F 4-F 4-COCH 3 0 HHHO 3-F 4-F 4 -COCH 2 CH = CH 2 0 HHHO 3-F 4-F 4-C0CH 2 C ≡ CH 0 HHHO 3-F 4-F 4-CO (Q3) 0 HHHO 3-F 4-F 4-COCF 3 0 HHHO 3-F 4-F 4- CO 2 CH 2 CH 3 0 HHHO 3-F 4-F 4-CO 2 C (CH 3) 3 ────────────────── ────────────────

【００３９】[0039]

【表５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 4-CO2CH2CF3 0 H H H O 3-F 4-F 4-OCH2CO2CH3 0 H H H O 3-F 4-F 4-NO2 0 H H H O 3-F 4-F 4-CN 0 H H H O 3-F 4-F 4-OH 0 H H H O 3-F 4-F 4-CO2H 0 H H H O 3-F 4-F 4-SCN 0 H H H O 3-F 4-F 4-OSO2CH3 0 H H H O 3-F 4-F 4-CSCH3 0 H H H O 3-F 4-F 4-NH2 0 H H H O 3-F 4-F 4-N(CH3)2 0 H H H O 3-F 4-F 4-N(CH3)CH2CH3 0 H H H O 3-F 4-F 4-N(CH3)CH2CH=CH2 0 H H H O 3-F 4-F 4-N(CH3)CH2Ｃ≡CH 0 H H H O 3-F 4-F 4-N(CH3)CH2C6H5 0 H H H O 3-F 4-F 4-CON(CH3)2 0 H H H O 3-F 4-F 4-0CON(CH3)2 0 H H H O 3-F 4-F 4-NHCOCH3 0 H H H O 3-F 4-F 4-NHCSCH3 0 H H H O 3-F 4-F 4-SO2N(CH3)2 0 H H H O 3-F 4-F 4-Si(CH3)3 0 H H H O 3-F 4-F 4-C6H5 0 H H H O 3-F 4-F 4-(C6H4-4-Cl) ───────────────────────────────────[Table 5] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-CO 2 CH 2 CF 3 0 HHHO 3-F 4-F 4-OCH 2 CO 2 CH 3 0 HHHO 3-F 4-F 4-NO 2 0 HHHO 3-F 4-F 4-CN 0 HHHO 3-F 4-F 4-OH 0 HHHO 3-F 4-F 4-CO 2 H 0 HHHO 3-F 4-F 4-SCN 0 HHHO 3-F 4-F 4-OSO 2 CH 3 0 HHHO 3-F 4-F 4 -CSCH 3 0 HHHO 3-F 4-F 4-NH 2 0 HHHO 3-F 4-F 4-N (CH 3 ) 20 HHHO 3-F 4-F 4-N (CH 3 ) CH 2 CH 3 0 HHHO 3-F 4-F 4-N (CH 3 ) CH 2 CH = CH 2 0 HHHO 3-F 4-F 4-N (CH 3 ) CH 2 C≡CH 0 HHHO 3-F 4-F 4 -N (CH 3) CH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CON (CH 3) 2 0 HHHO 3-F 4-F 4-0CON (CH 3) 2 0 HHHO 3-F 4 -F 4-NHCOCH 3 0 HHHO 3-F 4-F 4-NHCSCH 3 0 HHHO 3-F 4-F 4-SO 2 N (CH 3 ) 2 0 HHHO 3-F 4-F 4-Si (CH 3 ) 30 HHHO 3-F 4-F 4-C 6 H 5 0 HHHO 3-F 4-F 4- (C 6 H 4 -4-Cl) ─────────────── ──────────────── ────

【００４０】[0040]

【表６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 4-OC6H5 0 H H H O 3-F 4-F 4-O(C6H4-4-CF3) 0 H H H O 3-F 4-F 4-O(C6H4-4-OCF3) 0 H H H O 3-F 4-F 4-O(C6H3-2,4-F2) 0 H H H O 3-F 4-F 4-O(C6H3-3,5-Cl2) 0 H H H O 3-F 4-F 3-O(C6H4-4-CF3) 0 H H H O 3-F 4-F 4-S(C6H3-2-Cl-4-CF3) 0 H H H O 3-F 4-F 4-SO2C6H5 0 H H H O 3-F 4-F 4-NH(C6H3-2-Cl-4-CF3) 0 H H H O 3-F 4-F 4-N(CH2CH3)(C6H4-4-Cl) 0 H H H O 3-F 4-F 4-CH2C6H5 0 H H H O 3-F 4-F 4-CF2(C6H4-4-Br) 0 H H H O 3-F 4-F 4-COC6H5 0 H H H O 3-F 4-F 4-OCH2(C6H4-4-CF3) 0 H H H O 3-F 4-F 4-CH2OC6H5 0 H H H O 3-F 4-F 4-NHCH2C6H5 0 H H H O 3-F 4-F 4-CH2CH2C6H5 0 H H H O 3-F 4-F 4-CH=CH(C6H3-2,4-Cl2) 0 H H H O 3-F 4-F 4-N=NC6H5 0 H H H O 3-F 4-F 4-OCH2CH2C6H5 0 H H H O 3-F 4-F 4-NHCON(CH3)(C6H4-4-Cl) 0 H H H O 3-F 4-F 4-OCH2CH2OC6H5 0 H H H O 3-F 4-F 4-NHCSNHC6H5 ──────────────────────────────────[Table 6] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 4-OC 6 H 5 0 HHHO 3-F 4-F 4-O (C 6 H 4 -4-CF 3 ) 0 HHHO 3-F 4-F 4-O (C 6 H 4 -4-OCF 3 ) 0 HHHO 3-F 4-F 4-O (C 6 H 3 -2,4-F 2 ) 0 HHHO 3-F 4-F 4-O (C 6 H 3 -3,5-Cl 2 ) 0 HHHO 3-F 4- F 3-O (C 6 H 4 -4-CF 3 ) 0 HHHO 3-F 4-F 4-S (C 6 H 3 -2-Cl-4-CF 3 ) 0 HHHO 3-F 4-F 4 -SO 2 C 6 H 5 0 HHHO 3-F 4-F 4-NH (C 6 H 3 -2-Cl-4-CF 3) 0 HHHO 3-F 4-F 4-N (CH 2 CH 3) (C 6 H 4 -4-Cl) 0 HHHO 3-F 4-F 4-CH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CF 2 (C 6 H 4 -4-Br) 0 HHHO 3-F 4-F 4-COC 6 H 5 0 HHHO 3-F 4-F 4-OCH 2 (C 6 H 4 -4-CF 3 ) 0 HHHO 3-F 4-F 4-CH 2 OC 6 H 5 0 HHHO 3-F 4- F 4-NHCH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CH 2 CH 2 C 6 H 5 0 HHHO 3-F 4-F 4-CH = CH (C 6 H 3 -2,4-Cl 2 ) 0 HHHO 3-F 4-F 4-N = NC 6 H 5 0 HHHO 3-F 4-F 4-OCH 2 CH 2 C 6 H 5 0 HHHO 3-F 4-F 4-NHCON (CH 3 ) ( C 6 H 4 -4-Cl) 0 HHHO 3-F 4-F 4-OCH 2 CH 2 OC 6 H 5 0 HHHO 3-F 4-F 4-NHCSNHC 6 H 5 ────────── ─────────────────────────

【００４１】[0041]

【表７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 2,4-F2 0 H H H O 3-F 4-F 3,5-F2 0 H H H O 3-F 4-F 2,3-Cl2 0 H H H O 3-F 4-F 2,4-Cl2 0 H H H O 3-F 4-F 2,5-Cl2 0 H H H O 3-F 4-F 2,6-Cl2 0 H H H O 3-F 4-F 3,4-Cl2 0 H H H O 3-F 4-F 3,5-Cl2 0 H H H O 3-F 4-F 3,4-Br2 0 H H H O 3-F 4-F 2,4-I2 0 H H H O 3-F 4-F 2,4-(CH3)2 0 H H H O 3-F 4-F 3,4-(OCH3)2 0 H H H O 3-F 4-F 2-F-4-Cl 0 H H H O 3-F 4-F 2-F-4-Br 0 H H H O 3-F 4-F 2-F-4-OCH(CH3)2 0 H H H O 3-F 4-F 2-F-4-OCHF2 0 H H H O 3-F 4-F 2-F-4-OCF3 0 H H H O 3-F 4-F 2-F-4-OCF2CHF2 0 H H H O 3-F 4-F 2-F-4-OCF2CHFCl 0 H H H O 3-F 4-F 2-F-4-OCF2CHFCF3 0 H H H O 3-F 4-F 2-F-4-OCF2CHFOCF3 0 H H H O 3-F 4-F 2-F-4-SO2CF2CHFCl 0 H H H O 3-F 4-F 2-F-4-O(C6H4-4-Cl) ───────────────────────────────────[Table 7] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 2,4-F 20 HHHO 3-F 4-F 3,5-F 20 HHHO 3-F 4-F 2,3-Cl 20 HHHO 3-F 4-F 2,4-Cl 20 HHHO 3-F 4- F 2,5-Cl 2 0 HHHO 3-F 4-F 2,6-Cl 2 0 HHHO 3-F 4-F 3,4-Cl 2 0 HHHO 3-F 4-F 3,5-Cl 2 0 HHHO 3-F 4-F 3,4-Br 2 0 HHHO 3-F 4-F 2,4-I 2 0 HHHO 3-F 4-F 2,4- (CH 3 ) 2 0 HHHO 3-F 4 -F 3,4- (OCH 3 ) 20 HHHO 3-F 4-F 2-F-4-Cl 0 HHHO 3-F 4-F 2-F-4-Br 0 HHHO 3-F 4-F 2 -F-4-OCH (CH 3 ) 20 HHHO 3-F 4-F 2-F-4-OCHF 20 HHHO 3-F 4-F 2-F-4-OCF 3 0 HHHO 3-F 4- F 2-F-4-OCF 2 CHF 20 HHHO 3-F 4-F 2-F-4-OCF 2 CHFCl 0 HHHO 3-F 4-F 2-F-4-OCF 2 CHFCF 3 0 HHHO 3- F 4-F 2-F-4-OCF 2 CHFOCF 3 0 HHHO 3-F 4-F 2-F-4-SO 2 CF 2 CHFCl 0 HHHO 3-F 4-F 2-F-4-O (C 6 H 4 -4-Cl) ──────────────────────────────────

【００４２】[0042]

【表８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 2-F-4-O(Q5-3-Cl-5-CF3) 0 H H H O 3-F 4-F 3-F-4-O(Q5-3-Cl-5-CF3) 0 H H H O 3-F 4-F 2-Cl-4-CF3 0 H H H O 3-F 4-F 2-Cl-4-SCF2CHF2 0 H H H O 3-F 4-F 3-Cl-4-CF3 0 H H H O 3-F 4-F 3-F-4-OCF3 0 H H H O 3-F 4-F 3-Cl-4-OCF3 0 H H H O 3-F 4-F 3-Cl-4-OCHF2 0 H H H O 3-F 4-F 3-Cl-4-OCF2CHF2 0 H H H O 3-F 4-F 3-Cl-4-OCF2CHFOCF3 0 H H H O 3-F 4-F 3-Cl-4-SCHF2 0 H H H O 3-F 4-F 3-Cl-4-CO2CH3 0 H H H O 3-F 4-F 3-Cl-4-CO2CH(CH2F)2 0 H H H O 3-F 4-F 3-Cl-4-O(C6H4-4-CF3) 0 H H H O 3-F 4-F 3-Cl-4-O(Q5-5-CF3) 0 H H H O 3-F 4-F 3-Cl-4-NH(Q5-5-CF3) 0 H H H O 3-F 4-F 3-Br-4-OCF3 0 H H H O 3-F 4-F 3-CH3-4-OCF2CHF2 0 H H H O 3-F 4-F 3-CF3-4-Cl 0 H H H O 3-F 4-F 3-CF3-4-OCF2CHF2 0 H H H O 3-F 4-F 3-CF3-4-OCF2CHFBr 0 H H H O 3-F 4-F 3,4-(CF3)2 0 H H H O 3-F 4-F 3,4-(OCF3)2 ───────────────────────────────────[Table 8] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F-4 -O (Q5-3-Cl-5-CF 3 ) 0 HHHO 3-F 4-F 3-F-4-O (Q5-3-Cl-5-CF 3 ) 0 HHHO 3-F 4-F 2 -Cl-4-CF 3 0 HHHO 3-F 4-F 2-Cl-4-SCF 2 CHF 20 HHHO 3-F 4-F 3-Cl-4-CF 3 0 HHHO 3-F 4-F 3 -F-4-OCF 3 0 HHHO 3-F 4-F 3-Cl-4-OCF 3 0 HHHO 3-F 4-F 3-Cl-4-OCHF 2 0 HHHO 3-F 4-F 3-Cl -4-OCF 2 CHF 2 0 HHHO 3-F 4-F 3-Cl-4-OCF 2 CHFOCF 3 0 HHHO 3-F 4-F 3-Cl-4-SCHF 2 0 HHHO 3-F 4-F 3 -Cl-4-CO 2 CH 3 0 HHHO 3-F 4-F 3-Cl-4-CO 2 CH (CH 2 F) 2 0 HHHO 3-F 4-F 3-Cl-4-O (C 6 H 4 -4-CF 3 ) 0 HHHO 3-F 4-F 3-Cl-4-O (Q5-5-CF 3 ) 0 HHHO 3-F 4-F 3-Cl-4-NH (Q5-5 -CF 3 ) 0 HHHO 3-F 4-F 3-Br-4-OCF 3 0 HHHO 3-F 4-F 3-CH 3 -4-OCF 2 CHF 2 0 HHHO 3-F 4-F 3-CF 3 -4-Cl 0 HHHO 3-F 4-F 3-CF 3 -4-OCF 2 CHF 20 HHHO 3-F 4-F 3-CF 3 -4-OCF 2 CHFBr 0 HHHO 3-F 4-F 3,4- (CF 3 ) 20 HHHO 3-F 4- F 3,4- (OCF 3 ) 2 ────────────────────────────────────

【００４３】[0043]

【表９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 2,3-F2-4-OCF3 0 H H H O 3-F 4-F 2,5-F2-4-Cl 0 H H H O 3-F 4-F 2,5-F2-4-Br 0 H H H O 3-F 4-F 2,5-F2-4-OCF3 0 H H H O 3-F 4-F 3,5-F2-4-CF3 0 H H H O 3-F 4-F 2,5-Cl2-4-OCF2CHF2 0 H H H O 3-F 4-F 2,5-Cl2-4-O(Q5-3,5-Cl2) 0 H H H O 3-F 4-F 2,6-Cl2-4-CF3 0 H H H O 3-F 4-F 2,3,4-F3 0 H H H O 3-F 4-F 2,4,5-F3 0 H H H O 3-F 4-F 2,3,4-Cl3 0 H H H O 3-F 4-F 2,4,5-Cl3 0 H H H O 3-F 4-F 2,4,6-Cl3 0 H H H O 3-F 4-F 3,4,5-Cl3 0 H H H O 3-F 4-F 2-F-4,5-Cl2 0 H H H O 3-F 4-F 3,5-Cl2-4-O(Q5-5-CF3) 0 H H H O 3-F 4-F 3,5-Cl2-4-O(C6H4-4-CF3) 0 H H H O 3-F 4-F 3,5-Cl2-4-OCH2CH=CH2 0 H H H O 3-F 4-F 3,5-Cl2-4-OCF2CHF2 0 H H H O 3-F 4-F 3,5-Cl2-4-OCF2CHFOCF3 0 H H H O 3-F 4-F 3,5-Cl2-4-SCF2CHF2 0 H H H O 3-F 4-F 3,5-Cl2-4-N(CH3)CH2CH2CH3 0 H H H O 3-F 4-F 3,5-Cl2-4-N(CH3)CH2C6H5 ───────────────────────────────────[Table 9] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 2,3-F 2 -4-OCF 3 0 HHHO 3-F 4-F 2,5-F 2 -4-Cl 0 HHHO 3-F 4-F 2,5-F 2 -4-Br 0 HHHO 3-F 4-F 2,5-F 2 -4-OCF 3 0 HHHO 3-F 4-F 3,5-F 2 -4-CF 3 0 HHHO 3-F 4-F 2,5-Cl 2 -4-OCF 2 CHF 2 0 HHHO 3-F 4-F 2,5-Cl 2 -4-O (Q5-3,5-Cl 2 ) 0 HHHO 3-F 4-F 2,6-Cl 2 -4-CF 3 0 HHHO 3-F 4-F 2,3,4-F 3 0 HHHO 3-F 4-F 2,4,5-F 3 0 HHHO 3-F 4-F 2,3,4-Cl 3 0 HHHO 3- F 4-F 2,4,5-Cl 3 0 HHHO 3-F 4-F 2,4,6-Cl 3 0 HHHO 3-F 4-F 3,4,5-Cl 3 0 HHHO 3-F 4 -F 2-F-4,5-Cl 2 0 HHHO 3-F 4-F 3,5-Cl 2 -4-O (Q5-5-CF 3 ) 0 HHHO 3-F 4-F 3,5- Cl 2 -4-O (C 6 H 4 -4-CF 3 ) 0 HHHO 3-F 4-F 3,5-Cl 2 -4-OCH 2 CH = CH 2 0 HHHO 3-F 4-F 3, 5-Cl 2 -4-OCF 2 CHF 2 0 HHHO 3-F 4-F 3,5-Cl 2 -4-OCF 2 CHFOCF 3 0 HHHO 3-F 4-F 3,5-Cl 2 -4-SCF 2 CHF 2 0 HHHO 3-F 4-F 3,5-Cl 2 -4-N (CH 3 ) CH 2 CH 2 CH 3 0 HHHO 3-F 4-F 3,5-Cl 2 -4-N (CH 3 ) CH 2 C 6 H 5 ─────────────────────── ─────────────

【００４４】[0044]

【表１０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-F 2-F-3-CF3-5-Cl 0 H H H O 3-F 4-F 2-F-4-OCF3-5-Cl 0 H H H O 3-F 4-F 2-F-4-OCF2CHF2-5-Cl 0 H H H O 3-F 4-F 2-CF3-4,6-(NO2)2 0 H H H O 3-F 4-F 2,3,4,5-F4 0 H H H O 3-F 4-F 2,3,5,6-F4 0 H H H O 3-F 4-F 2,3,4,5-Cl4 0 H H H O 3-F 4-F 2,4-F2-3,5-Cl2 0 H H H O 3-F 4-F 2,6-F2-3,5-Cl2 0 H H H O 3-F 4-F 2,3,5-F3-4-OCF3 0 H H H O 3-F 4-F 2-F-3,5-Cl2-4-OCF2CHF2 0 H H H O 3-F 4-F 2,3,4,5,6-F5 0 H H H O 3-F 4-F 2,3,5,6-F4-4-CN 0 H H H O 3-F 4-F 2,4,6-F3-3,5-Cl2 0 H H H O 3-F 4-F 3-Cl-4-F 0 H H H O 3-F 4-F 4-OSO2CF3 0 H H H O 3-F 4-F 4-(Q1-2,2-Cl2) 0 H H H O 3-F 4-F 4-SO2CF2CF2CF3 0 H H H O 3-F 4-F 4-SOCF2CHF2 0 H H H O 3-F 4-F 4-SO2CHF2 0 H H H O 3-F 4-F 3-OCF2O-4 0 H H H O 3-F 4-F 3-OCH2O-4 0 H H H O 3-F 4-F 3-OCF2CF2O-4 ───────────────────────────────────[Table 10] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-F 2-F-3 -CF 3 -5-Cl 0 HHHO 3-F 4-F 2-F-4-OCF 3 -5-Cl 0 HHHO 3-F 4-F 2-F-4-OCF 2 CHF 2 -5-Cl 0 HHHO 3-F 4-F 2-CF 3 -4,6- (NO 2 ) 2 0 HHHO 3-F 4-F 2,3,4,5-F 4 0 HHHO 3-F 4-F 2,3 , 5,6-F 40 HHHO 3-F 4-F 2,3,4,5-Cl 4 0 HHHO 3-F 4-F 2,4-F 2 -3,5-Cl 2 0 HHHO 3- F 4-F 2,6-F 2 -3,5-Cl 2 0 HHHO 3-F 4-F 2,3,5-F 3 -4-OCF 3 0 HHHO 3-F 4-F 2-F- 3,5-Cl 2 -4-OCF 2 CHF 2 0 HHHO 3-F 4-F 2,3,4,5,6-F 5 0 HHHO 3-F 4-F 2,3,5,6-F 4 -4-CN 0 HHHO 3-F 4-F 2,4,6-F 3 -3,5-Cl 2 0 HHHO 3-F 4-F 3-Cl-4-F 0 HHHO 3-F 4- F 4-OSO 2 CF 3 0 HHHO 3-F 4-F 4- (Q1-2,2-Cl 2 ) 0 HHHO 3-F 4-F 4-SO 2 CF 2 CF 2 CF 3 0 HHHO 3-F 4-F 4-SOCF 2 CHF 20 HHHO 3-F 4-F 4-SO 2 CHF 20 HHHO 3-F 4-F 3-OCF 2 O-4 0 HHHO 3-F 4-F 3-OCH 2 O-4 0 HHHO 3-F 4-F 3-OCF 2 CF 2 O-4 ───── ─────────────────────────────

【００４５】[0045]

【表１１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-F 4-F 0 H H H O 3-CF3 4-F 3-Cl 0 H H H O 3-CF3 4-F 4-Cl 0 H H H O 3-CF3 4-F 4-Br 0 H H H O 3-CF3 4-F 4-I 0 H H H O 3-CF3 4-F 4-CH3 0 H H H O 3-CF3 4-F 4-C(CH3)3 0 H H H O 3-CF3 4-F 4-CHF2 0 H H H O 3-CF3 4-F 3-CF3 0 H H H O 3-CF3 4-F 4-CF3 0 H H H O 3-CF3 4-F 4-OCH3 0 H H H O 3-CF3 4-F 4-OCH2CH3 0 H H H O 3-CF3 4-F 4-OCHF2 0 H H H O 3-CF3 4-F 4-OCF2Br 0 H H H O 3-CF3 4-F 3-OCF3 0 H H H O 3-CF3 4-F 4-OCF3 0 H H H O 3-CF3 4-F 4-OCH2CF3 0 H H H O 3-CF3 4-F 4-OCF2CF3 0 H H H O 3-CF3 4-F 4-OCF2CHF2 0 H H H O 3-CF3 4-F 4-OCF2CHFCl 0 H H H O 3-CF3 4-F 4-0CF2CF2CF3 0 H H H O 3-CF3 4-F 4-SCH3 0 H H H O 3-CF3 4-F 4-SCHF2 ───────────────────────────────────[Table 11] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-F 4-F 0 HHHO 3-CF 3 4-F 3-Cl 0 HHHO 3-CF 3 4-F 4-Cl 0 HHHO 3-CF 3 4-F 4-Br 0 HHHO 3-CF 3 4-F 4-I 0 HHHO 3 -CF 3 4-F 4-CH 30 HHHO 3-CF 3 4-F 4-C (CH 3 ) 30 HHHO 3-CF 3 4-F 4-CHF 2 0 HHHO 3-CF 3 4-F 3 -CF 30 HHHO 3-CF 3 4-F 4-CF 30 HHHO 3-CF 3 4-F 4-OCH 30 HHHO 3-CF 3 4-F 4-OCH 2 CH 30 HHHO 3-CF 3 4-F 4-OCHF 2 0 HHHO 3-CF 3 4-F 4-OCF 2 Br 0 HHHO 3-CF 3 4-F 3-OCF 3 0 HHHO 3-CF 3 4-F 4-OCF 3 0 HHHO 3 -CF 3 4-F 4-OCH 2 CF 3 0 HHHO 3-CF 3 4-F 4-OCF 2 CF 3 0 HHHO 3-CF 3 4-F 4-OCF 2 CHF 20 HHHO 3-CF 3 4- F 4-OCF 2 CHFCl 0 HHHO 3-CF 3 4-F 4-0CF 2 CF 2 CF 3 0 HHHO 3-CF 3 4-F 4-SCH 3 0 HHHO 3-CF 3 4-F 4-SCHF 2 ─ ──────────────────────────────────

【００４６】[0046]

【表１２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-F 4-SCF2Br 0 H H H O 3-CF3 4-F 4-SCF3 0 H H H O 3-CF3 4-F 4-SOCH3 0 H H H O 3-CF3 4-F 4-SOCF3 0 H H H O 3-CF3 4-F 4-SO2CH3 0 H H H O 3-CF3 4-F 4-SO2CF3 0 H H H O 3-CF3 4-F 4-SO2CF2CHF2 0 H H H O 3-CF3 4-F 4-OCO2CH3 0 H H H O 3-CF3 4-F 4-OCF2CHFOCF3 0 H H H O 3-CF3 4-F 4-OCOCH3 0 H H H O 3-CF3 4-F 4-COCH3 0 H H H O 3-CF3 4-F 4-COCF3 0 H H H O 3-CF3 4-F 4-CO2CH2CH3 0 H H H O 3-CF3 4-F 4-CO2CH2CF3 0 H H H O 3-CF3 4-F 4-NO2 0 H H H O 3-CF3 4-F 4-CN 0 H H H O 3-CF3 4-F 4-OH 0 H H H O 3-CF3 4-F 4-CO2H 0 H H H O 3-CF3 4-F 4-OSO2CH3 0 H H H O 3-CF3 4-F 4-OSO2CF3 0 H H H O 3-CF3 4-F 4-N(CH3)2 0 H H H O 3-CF3 4-F 4-Si(CH3)3 0 H H H O 3-CF3 4-F 4-C6H5 ───────────────────────────────────[Table 12] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-F 4-SCF 2 Br 0 HHHO 3-CF 3 4-F 4-SCF 30 HHHO 3-CF 3 4-F 4-SOCH 30 HHHO 3-CF 3 4-F 4-SOCF 30 HHHO 3-CF 3 4-F 4 -SO 2 CH 3 0 HHHO 3-CF 3 4-F 4-SO 2 CF 3 0 HHHO 3-CF 3 4-F 4-SO 2 CF 2 CHF 20 HHHO 3-CF 3 4-F 4-OCO 2 CH 3 0 HHHO 3-CF 3 4-F 4-OCF 2 CHFOCF 3 0 HHHO 3-CF 3 4-F 4-OCOCH 3 0 HHHO 3-CF 3 4-F 4-COCH 3 0 HHHO 3-CF 3 4 -F 4-COCF 3 0 HHHO 3-CF 3 4-F 4-CO 2 CH 2 CH 3 0 HHHO 3-CF 3 4-F 4-CO 2 CH 2 CF 3 0 HHHO 3-CF 3 4-F 4 -NO 2 0 HHHO 3-CF 3 4-F 4-CN 0 HHHO 3-CF 3 4-F 4-OH 0 HHHO 3-CF 3 4-F 4-CO 2 H 0 HHHO 3-CF 3 4-F 4-OSO 2 CH 3 0 HHHO 3-CF 3 4-F 4-OSO 2 CF 3 0 HHHO 3-CF 3 4-F 4-N (CH 3 ) 2 0 HHHO 3-CF 3 4-F 4-Si (CH 3) 3 0 HHHO 3 -CF 3 4-F 4-C 6 H 5 ─────────────────────── ───────────

【００４７】[0047]

【表１３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-F 4-OC6H5 0 H H H O 3-CF3 4-F 4-O(C6H4-4-CF3) 0 H H H O 3-CF3 4-F 4-O(Q5-5-CF3) 0 H H H O 3-CF3 4-F 4-SO2C6H5 0 H H H O 3-CF3 4-F 4-CH2C6H5 0 H H H O 3-CF3 4-F 4-COC6H5 0 H H H O 3-CF3 4-F 2,4-F2 0 H H H O 3-CF3 4-F 3,4-Cl2 0 H H H O 3-CF3 4-F 3,4-Br2 0 H H H O 3-CF3 4-F 2-F-4-Cl 0 H H H O 3-CF3 4-F 2-F-4-OCF3 0 H H H O 3-CF3 4-F 2-F-4-OCF2CHF2 0 H H H O 3-CF3 4-F 3-Cl-4-CF3 0 H H H O 3-CF3 4-F 3-F-4-OCF3 0 H H H O 3-CF3 4-F 2-F-4-OCF2CHF2 0 H H H O 3-CF3 4-F 3-Cl-4-OCF2CHFOCF3 0 H H H O 3-CF3 4-F 3-Cl-4-SCHF2 0 H H H O 3-CF3 4-F 2,5-F2-4-OCF3 0 H H H O 3-CF3 4-F 2-F-4,5-Cl2 0 H H H O 3-CF3 4-F 3,5-Cl2-4-OCF2CHF2 0 H H H O 3-CF3 4-F 3,4,5-Cl3 0 H H H O 3-CF3 4-F 2-F-4-OCF2CHF2-5-Cl 0 H H H O 3-CF3 4-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 13] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-F 4-OC 6 H 5 0 HHHO 3-CF 3 4-F 4-O (C 6 H 4 -4-CF 3 ) 0 HHHO 3-CF 3 4-F 4-O (Q5-5-CF 3 ) 0 HHHO 3-CF 3 4-F 4-SO 2 C 6 H 5 0 HHHO 3-CF 3 4-F 4-CH 2 C 6 H 5 0 HHHO 3-CF 3 4-F 4-COC 6 H 5 0 HHHO 3-CF 3 4-F 2,4-F 20 HHHO 3-CF 3 4-F 3,4-Cl 2 0 HHHO 3-CF 3 4-F 3,4-Br 20 HHHO 3-CF 3 4-F 2- F-4-Cl 0 HHHO 3-CF 3 4-F 2-F-4-OCF 3 0 HHHO 3-CF 3 4-F 2-F-4-OCF 2 CHF 20 HHHO 3-CF 3 4-F 3-Cl-4-CF 3 0 HHHO 3-CF 3 4-F 3-F-4-OCF 3 0 HHHO 3-CF 3 4-F 2-F-4-OCF 2 CHF 2 0 HHHO 3-CF 3 4-F 3-Cl-4-OCF 2 CHFOCF 3 0 HHHO 3-CF 3 4-F 3-Cl-4-SCHF 20 HHHO 3-CF 3 4-F 2,5-F 2 -4-OCF 3 0 HHHO 3-CF 3 4-F 2-F-4,5-Cl 2 0 HHHO 3-CF 3 4-F 3,5-Cl 2 -4-OCF 2 CHF 2 0 HHHO 3-CF 3 4-F 3,4,5-Cl 3 0 HHHO 3-CF 3 4-F 2-F-4-OCF 2 CHF 2 -5-Cl 0 HHHO 3-CF 3 4-F 2,4-F 2 -3,5-Cl 2 ────────────────────────────────────

【００４８】[0048]

【表１４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl 4-F 4-Cl 0 H H H O 3-Cl 4-F 4-Br 0 H H H O 3-Cl 4-F 4-CF3 0 H H H O 3-Cl 4-F 4-OCH2CH3 0 H H H O 3-Cl 4-F 4-OCHF2 0 H H H O 3-Cl 4-F 4-OCF2Br 0 H H H O 3-Cl 4-F 4-OCF2CHF2 0 H H H O 3-Cl 4-F 4-OCF3 0 H H H O 3-Cl 4-F 4-SCHF2 0 H H H O 3-Cl 4-F 4-SCF2Br 0 H H H O 3-Cl 4-F 4-SCF3 0 H H H O 3-Cl 4-F 4-O(Q6-6-Cl) 0 H H H O 3-Cl 4-F 4-O(Q7) 0 H H H O 3-Cl 4-F 4-O(Q5-5-CF3) 0 H H H O 3-Cl 4-F 4-OCF2CHFOCF3 0 H H H O 3-Cl 4-F 4-COCF3 0 H H H O 3-Cl 4-F 4-CO2CH2CH3 0 H H H O 3-Cl 4-F 4-NO2 0 H H H O 3-Cl 4-F 4-CN 0 H H H O 3-Cl 4-F 4-OSO2CF3 0 H H H O 3-Cl 4-F 3,4-Cl2 0 H H H O 3-Cl 4-F 3-Cl-4-OCF2CHF2 0 H H H O 3-Cl 4-F 2,4-F2-3,5-Cl2 ───────────────────────────────────[Table 14] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl 4-F 4-Cl 0 HHHO 3-Cl 4-F 4-Br 0 HHHO 3-Cl 4-F 4-CF 3 0 HHHO 3-Cl 4-F 4-OCH 2 CH 3 0 HHHO 3-Cl 4-F 4-OCHF 20 HHHO 3 -Cl 4-F 4-OCF 2 Br 0 HHHO 3-Cl 4-F 4-OCF 2 CHF 2 0 HHHO 3-Cl 4-F 4-OCF 3 0 HHHO 3-Cl 4-F 4-SCHF 20 HHHO 3-Cl 4-F 4-SCF 2 Br 0 HHHO 3-Cl 4-F 4-SCF 3 0 HHHO 3-Cl 4-F 4-O (Q6-6-Cl) 0 HHHO 3-Cl 4-F 4 -O (Q7) 0 HHHO 3-Cl 4-F 4-O (Q5-5-CF 3 ) 0 HHHO 3-Cl 4-F 4-OCF 2 CHFOCF 3 0 HHHO 3-Cl 4-F 4-COCF 3 0 HHHO 3-Cl 4-F 4-CO 2 CH 2 CH 3 0 HHHO 3-Cl 4-F 4-NO 2 0 HHHO 3-Cl 4-F 4-CN 0 HHHO 3-Cl 4-F 4-OSO 2 CF 3 0 HHHO 3-Cl 4-F 3,4-Cl 2 0 HHHO 3-Cl 4-F 3-Cl-4-OCF 2 CHF 2 0 HHHO 3-Cl 4-F 2,4-F 2- 3,5-Cl 2 ────────────────────────────────────

【００４９】[0049]

【表１５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O H H 4-Cl 0 H H H O H H 4-Br 0 H H H O H H 4-CF3 0 H H H O H H 4-OCHF2 0 H H H O H H 4-OCF2Br 0 H H H O H H 4-OCF2CHF2 0 H H H O H H 4-OCF3 0 H H H O H H 4-SCF3 0 H H H O H H 4-OSO2CF3 0 H H H O H H 3,4-Cl2 0 H H H O H 4-F 4-Cl 0 H H H O H 4-F 4-Br 0 H H H O H 4-F 4-CF3 0 H H H O H 4-F 4-OCHF2 0 H H H O H 4-F 4-OCF2Br 0 H H H O H 4-F 4-OCF2CHF2 0 H H H O H 4-F 4-OCF3 0 H H H O H 4-F 4-SCF3 0 H H H O H 4-F 4-OSO2CF3 0 H H H O H 4-F 3,4-Cl2 0 H H H O H 4-CN 4-Cl 0 H H H O H 4-CN 4-Br 0 H H H O H 4-CN 4-CF3 ───────────────────────────────────[Table 15] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHOHH 4-Cl 0 HHHOHH 4-Br 0 HHHOHH 4 -CF 3 0 HHHOHH 4-OCHF 2 0 HHHOHH 4-OCF 2 Br 0 HHHOHH 4-OCF 2 CHF 2 0 HHHOHH 4-OCF 3 0 HHHOHH 4-SCF 3 0 HHHOHH 4-OSO 2 CF 3 0 HHHOHH 3,4- Cl 2 0 HHHOH 4-F 4-Cl 0 HHHOH 4-F 4-Br 0 HHHOH 4-F 4-CF 3 0 HHHOH 4-F 4-OCHF 2 0 HHHOH 4-F 4-OCF 2 Br 0 HHHOH 4- F 4-OCF 2 CHF 20 HHHOH 4-F 4-OCF 3 0 HHHOH 4-F 4-SCF 3 0 HHHOH 4-F 4-OSO 2 CF 3 0 HHHOH 4-F 3,4-Cl 2 0 HHHOH 4 -CN 4-Cl 0 HHHOH 4-CN 4-Br 0 HHHOH 4-CN 4-CF 3 ───────────────────────────── ───────

【００５０】[0050]

【表１６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O H 4-CN 4-OCHF2 0 H H H O H 4-CN 4-OCF2Br 0 H H H O H 4-CN 4-OCF2CHF2 0 H H H O H 4-CN 4-OCF3 0 H H H O H 4-CN 4-SCF3 0 H H H O H 4-CN 4-OSO2CF3 0 H H H O H 4-CN 3,4-Cl2 0 H H H O H 4-Cl 4-Cl 0 H H H O H 4-Cl 4-Br 0 H H H O H 4-Cl 4-CF3 0 H H H O H 4-Cl 4-OCHF2 0 H H H O H 4-Cl 4-OCF2Br 0 H H H O H 4-Cl 4-OCF2CHF2 0 H H H O H 4-Cl 4-OCF3 0 H H H O H 4-Cl 4-SCF3 0 H H H O H 4-Cl 4-OSO2CF3 0 H H H O H 4-Cl 3,4-Cl2 0 H H H O H 4-CF3 4-Cl 0 H H H O H 4-CF3 4-Br 0 H H H O H 4-CF3 4-CF3 0 H H H O H 4-CF3 4-OCHF2 0 H H H O H 4-CF3 4-OCF2Br 0 H H H O H 4-CF3 4-OCF2CHF2 ──────────────────────────────────[Table 16] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHOH 4-CN 4-OCHF 2 0 HHHOH 4- CN 4-OCF 2 Br 0 HHHOH 4-CN 4-OCF 2 CHF 2 0 HHHOH 4-CN 4-OCF 3 0 HHHOH 4-CN 4-SCF 3 0 HHHOH 4-CN 4-OSO 2 CF 3 0 HHHOH 4- CN 3,4-Cl 2 0 HHHOH 4-Cl 4-Cl 0 HHHOH 4-Cl 4-Br 0 HHHOH 4-Cl 4-CF 3 0 HHHOH 4-Cl 4-OCHF 2 0 HHHOH 4-Cl 4-OCF 2 Br 0 HHHOH 4-Cl 4-OCF 2 CHF 2 0 HHHOH 4-Cl 4-OCF 3 0 HHHOH 4-Cl 4-SCF 3 0 HHHOH 4-Cl 4-OSO 2 CF 3 0 HHHOH 4-Cl 3,4- Cl 2 0 HHHOH 4-CF 3 4-Cl 0 HHHOH 4-CF 3 4-Br 0 HHHOH 4-CF 3 4-CF 3 0 HHHOH 4-CF 3 4-OCHF 2 0 HHHOH 4-CF 3 4-OCF 2 Br 0 HHHOH 4-CF 3 4-OCF 2 CHF 2 ───────────────────────────────────

【００５１】[0051]

【表１７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O H 4-CF3 4-OCF3 0 H H H O H 4-CF3 4-SCF3 0 H H H O H 4-CF3 4-OSO2CF3 0 H H H O H 4-CF3 3,4-Cl2 0 H H H O H 4-OSO2CF3 4-Cl 0 H H H O H 4-OSO2CF3 4-Br 0 H H H O H 4-OSO2CF3 4-CF3 0 H H H O H 4-OSO2CF3 4-OCHF2 0 H H H O H 4-OSO2CF3 4-OCF2Br 0 H H H O 3-F 4-OSO2CF3 4-OCF2CHF2 0 H H H O 3-F 4-OSO2CF3 4-OCF3 0 H H H O 3-F 4-OSO2CF3 4-SCF3 0 H H H O 3-F 4-OSO2CF3 4-OSO2CF3 0 H H H O 3-F 4-OSO2CF3 3,4-Cl2 0 H H H O 3-F 4-Cl 4-Cl 0 H H H O 3-F 4-Cl 4-Br 0 H H H O 3-F 4-Cl 4-CF3 0 H H H O 3-F 4-Cl 4-OCHF2 0 H H H O 3-F 4-Cl 4-OCF2Br 0 H H H O 3-F 4-Cl 4-OCF2CHF2 0 H H H O 3-F 4-Cl 4-OCF3 0 H H H O 3-F 4-Cl 4-SCF3 0 H H H O 3-F 4-Cl 4-OSO2CF3 ───────────────────────────────────[Table 17] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHOH 4-CF 3 4-OCF 3 0 HHHOH 4 -CF 3 4-SCF 3 0 HHHOH 4-CF 3 4-OSO 2 CF 3 0 HHHOH 4-CF 3 3,4-Cl 2 0 HHHOH 4-OSO 2 CF 3 4-Cl 0 HHHOH 4-OSO 2 CF 3 4-Br 0 HHHOH 4-OSO 2 CF 3 4-CF 3 0 HHHOH 4-OSO 2 CF 3 4-OCHF 2 0 HHHOH 4-OSO 2 CF 3 4-OCF 2 Br 0 HHHO 3-F 4-OSO 2 CF 3 4-OCF 2 CHF 20 HHHO 3-F 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-F 4-OSO 2 CF 3 4-SCF 30 HHHO 3-F 4-OSO 2 CF 3 4- OSO 2 CF 3 0 HHHO 3-F 4-OSO 2 CF 3 3,4-Cl 2 0 HHHO 3-F 4-Cl 4-Cl 0 HHHO 3-F 4-Cl 4-Br 0 HHHO 3-F 4- Cl 4-CF 3 0 HHHO 3-F 4-Cl 4-OCHF 2 0 HHHO 3-F 4-Cl 4-OCF 2 Br 0 HHHO 3-F 4-Cl 4-OCF 2 CHF 20 HHHO 3-F 4 -Cl 4-OCF 3 0 HHHO 3-F 4-Cl 4-SCF 3 0 HHHO 3-F 4-Cl 4-OSO 2 CF 3 ─────────────────── ─────────────────

【００５２】[0052]

【表１８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-Cl 3,4-Cl2 0 H H H O 3-F 4-OCF3 4-Cl 0 H H H O 3-F 4-OCF3 4-Br 0 H H H O 3-F 4-OCF3 4-CF3 0 H H H O 3-F 4-OCF3 4-OCHF2 0 H H H O 3-F 4-OCF3 4-OCF2Br 0 H H H O 3-F 4-OCF3 4-OCF2CHF2 0 H H H O 3-F 4-OCF3 4-OCF3 0 H H H O 3-F 4-OCF3 4-SCF3 0 H H H O 3-F 4-OCF3 4-OSO2CF3 0 H H H O 3-F 4-OCF3 3,4-Cl2 0 H H H O 3-F 4-OCHF2 4-Cl 0 H H H O 3-F 4-OCHF2 4-Br 0 H H H O 3-F 4-OCHF2 4-CF3 0 H H H O 3-F 4-OCHF2 4-OCHF2 0 H H H O 3-F 4-OCHF2 4-OCF2Br 0 H H H O 3-F 4-OCHF2 4-OCF2CHF2 0 H H H O 3-F 4-OCHF2 4-OCF3 0 H H H O 3-F 4-OCHF2 4-SCF3 0 H H H O 3-F 4-OCHF2 4-OSO2CF3 0 H H H O 3-F 4-OCHF2 3,4-Cl2 0 H H H O 3-F 4-Br 4-Cl 0 H H H O 3-F 4-Br 4-Br ───────────────────────────────────[Table 18] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-Cl 3,4-Cl 2 0 HHHO 3-F 4-OCF 3 4-Cl 0 HHHO 3-F 4-OCF 3 4-Br 0 HHHO 3-F 4-OCF 3 4-CF 3 0 HHHO 3-F 4-OCF 3 4-OCHF 2 0 HHHO 3-F 4-OCF 3 4-OCF 2 Br 0 HHHO 3-F 4-OCF 3 4-OCF 2 CHF 2 0 HHHO 3-F 4-OCF 3 4-OCF 3 0 HHHO 3-F 4- OCF 3 4-SCF 3 0 HHHO 3-F 4-OCF 3 4-OSO 2 CF 3 0 HHHO 3-F 4-OCF 3 3,4-Cl 2 0 HHHO 3-F 4-OCHF 2 4-Cl 0 HHHO 3-F 4-OCHF 2 4-Br 0 HHHO 3-F 4-OCHF 2 4-CF 3 0 HHHO 3-F 4-OCHF 2 4-OCHF 20 HHHO 3-F 4-OCHF 2 4-OCF 2 Br 0 HHHO 3-F 4-OCHF 2 4-OCF 2 CHF 2 0 HHHO 3-F 4-OCHF 2 4-OCF 3 0 HHHO 3-F 4-OCHF 2 4-SCF 3 0 HHHO 3-F 4-OCHF 2 4-OSO 2 CF 3 0 HHHO 3-F 4-OCHF 2 3,4-Cl 2 0 HHHO 3-F 4-Br 4-Cl 0 HHHO 3-F 4-Br 4-Br ──────── ────────────────────────────

【００５３】[0053]

【表１９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 4-Br 4-CF3 0 H H H O 3-F 4-Br 4-OCHF2 0 H H H O 3-F 4-Br 4-OCF2Br 0 H H H O 3-F 4-Br 4-OCF2CHF2 0 H H H O 3-F 4-Br 4-OCF3 0 H H H O 3-F 4-Br 4-SCF3 0 H H H O 3-F 4-Br 4-OSO2CF3 0 H H H O 3-F 4-Br 3,4-Cl2 0 H H H O 3-Br 4-F 4-Cl 0 H H H O 3-Br 4-F 4-Br 0 H H H O 3-Br 4-F 4-CF3 0 H H H O 3-Br 4-F 4-OCHF2 0 H H H O 3-Br 4-F 4-OCF2Br 0 H H H O 3-Br 4-F 4-OCF2CHF2 0 H H H O 3-Br 4-F 4-OCF3 0 H H H O 3-Br 4-F 4-SCF3 0 H H H O 3-Br 4-F 4-OSO2CF3 0 H H H O 3-Br 4-F 3,4-Cl2 0 H H H O 3-OCHF2 4-F 4-Cl 0 H H H O 3-OCHF2 4-F 4-Br 0 H H H O 3-OCHF2 4-F 4-CF3 0 H H H O 3-OCHF2 4-F 4-OCHF2 0 H H H O 3-OCHF2 4-F 4-OCF2Br ───────────────────────────────────[Table 19] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 4-Br 4-CF 3 0 HHHO 3-F 4-Br 4-OCHF 20 HHHO 3-F 4-Br 4-OCF 2 Br 0 HHHO 3-F 4-Br 4-OCF 2 CHF 2 0 HHHO 3-F 4-Br 4-OCF 3 0 HHHO 3-F 4-Br 4-SCF 3 0 HHHO 3-F 4-Br 4-OSO 2 CF 3 0 HHHO 3-F 4-Br 3,4-Cl 2 0 HHHO 3-Br 4-F 4- Cl 0 HHHO 3-Br 4-F 4-Br 0 HHHO 3-Br 4-F 4-CF 3 0 HHHO 3-Br 4-F 4-OCHF 20 HHHO 3-Br 4-F 4-OCF 2 Br 0 HHHO 3-Br 4-F 4-OCF 2 CHF 2 0 HHHO 3-Br 4-F 4-OCF 3 0 HHHO 3-Br 4-F 4-SCF 3 0 HHHO 3-Br 4-F 4-OSO 2 CF 3 0 HHHO 3-Br 4-F 3,4-Cl 2 0 HHHO 3-OCHF 2 4-F 4-Cl 0 HHHO 3-OCHF 2 4-F 4-Br 0 HHHO 3-OCHF 2 4-F 4- CF 3 0 HHHO 3-OCHF 2 4-F 4-OCHF 20 HHHO 3-OCHF 2 4-F 4-OCF 2 Br ────────────────────── ──────────────

【００５４】[0054]

【表２０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-OCHF2 4-F 4-OCF2CHF2 0 H H H O 3-OCHF2 4-F 4-OCF3 0 H H H O 3-OCHF2 4-F 4-SCF3 0 H H H O 3-OCHF2 4-F 4-OSO2CF3 0 H H H O 3-OCHF2 4-F 3,4-Cl2 0 H H H O 3-OSO2CF3 4-F 4-Cl 0 H H H O 3-OSO2CF3 4-F 4-Br 0 H H H O 3-OSO2CF3 4-F 4-CF3 0 H H H O 3-OSO2CF3 4-F 4-OCHF2 0 H H H O 3-OSO2CF3 4-F 4-OCF2Br 0 H H H O 3-OSO2CF3 4-F 4-OCF2CHF2 0 H H H O 3-OSO2CF3 4-F 4-OCF3 0 H H H O 3-OSO2CF3 4-F 4-SCF3 0 H H H O 3-OSO2CF3 4-F 4-OSO2CF3 0 H H H O 3-OSO2CF3 4-F 3,4-Cl2 0 H H H O 3-OCF3 4-F 4-Cl 0 H H H O 3-OCF3 4-F 4-Br 0 H H H O 3-OCF3 4-F 4-CF3 0 H H H O 3-OCF3 4-F 4-OCHF2 0 H H H O 3-OCF3 4-F 4-OCF2Br 0 H H H O 3-OCF3 4-F 4-OCF2CHF2 0 H H H O 3-OCF3 4-F 4-OCF3 0 H H H O 3-OCF3 4-F 4-SCF3 ───────────────────────────────────[Table 20] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-OCHF 2 4-F 4-OCF 2 CHF 20 HHHO 3-OCHF 2 4-F 4-OCF 3 0 HHHO 3-OCHF 2 4-F 4-SCF 3 0 HHHO 3-OCHF 2 4-F 4-OSO 2 CF 3 0 HHHO 3-OCHF 2 4 -F 3,4-Cl 2 0 HHHO 3-OSO 2 CF 3 4-F 4-Cl 0 HHHO 3-OSO 2 CF 3 4-F 4-Br 0 HHHO 3-OSO 2 CF 3 4-F 4-CF 3 0 HHHO 3-OSO 2 CF 3 4-F 4-OCHF 2 0 HHHO 3-OSO 2 CF 3 4-F 4-OCF 2 Br 0 HHHO 3-OSO 2 CF 3 4-F 4-OCF 2 CHF 2 0 HHHO 3-OSO 2 CF 3 4-F 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-F 4-SCF 3 0 HHHO 3-OSO 2 CF 3 4-F 4-OSO 2 CF 3 0 HHHO 3- OSO 2 CF 3 4-F 3,4-Cl 2 0 HHHO 3-OCF 3 4-F 4-Cl 0 HHHO 3-OCF 3 4-F 4-Br 0 HHHO 3-OCF 3 4-F 4-CF 3 0 HHHO 3-OCF 3 4-F 4-OCHF 2 0 HHHO 3-OCF 3 4-F 4-OCF 2 Br 0 HHHO 3-OCF 3 4-F 4-OCF 2 CHF 2 0 HHHO 3-OCF 3 4- F 4-OCF 3 0 HHHO 3-OCF 3 4-F 4-SCF 3 ─────────────── ────────────────────

【００５５】[0055]

【表２１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-OCF3 4-F 4-OSO2CF3 0 H H H O 3-OCF3 4-F 3,4-Cl2 0 H H H O 3-Cl 4-CN 4-Cl 0 H H H O 3-Cl 4-CN 4-Br 0 H H H O 3-Cl 4-CN 4-CF3 0 H H H O 3-Cl 4-CN 4-OCHF2 0 H H H O 3-Cl 4-CN 4-OCF2Br 0 H H H O 3-Cl 4-CN 4-OCF2CHF2 0 H H H O 3-Cl 4-CN 4-OCF3 0 H H H O 3-Cl 4-CN 4-SCF3 0 H H H O 3-Cl 4-CN 4-OSO2CF3 0 H H H O 3-Cl 4-CN 3,4-Cl2 0 H H H O 3-CF3 4-CN 4-Cl 0 H H H O 3-CF3 4-CN 4-Br 0 H H H O 3-CF3 4-CN 4-CF3 0 H H H O 3-CF3 4-CN 4-OCHF2 0 H H H O 3-CF3 4-CN 4-OCF2Br 0 H H H O 3-CF3 4-CN 4-OCF2CHF2 0 H H H O 3-CF3 4-CN 4-OCF3 0 H H H O 3-CF3 4-CN 4-SCF3 0 H H H O 3-CF3 4-CN 4-OSO2CF3 0 H H H O 3-CF3 4-CN 3,4-Cl2 0 H H H O 3-OCF2CHF2 4-F 4-Cl ───────────────────────────────────[Table 21] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-OCF 3 4-F 4-OSO 2 CF 3 0 HHHO 3-OCF 3 4-F 3,4-Cl 2 0 HHHO 3-Cl 4-CN 4-Cl 0 HHHO 3-Cl 4-CN 4-Br 0 HHHO 3-Cl 4-CN 4-CF 3 0 HHHO 3-Cl 4-CN 4-OCHF 2 0 HHHO 3-Cl 4-CN 4-OCF 2 Br 0 HHHO 3-Cl 4-CN 4-OCF 2 CHF 2 0 HHHO 3-Cl 4-CN 4- OCF 3 0 HHHO 3-Cl 4-CN 4-SCF 3 0 HHHO 3-Cl 4-CN 4-OSO 2 CF 3 0 HHHO 3-Cl 4-CN 3,4-Cl 2 0 HHHO 3-CF 3 4- CN 4-Cl 0 HHHO 3-CF 3 4-CN 4-Br 0 HHHO 3-CF 3 4-CN 4-CF 3 0 HHHO 3-CF 3 4-CN 4-OCHF 2 0 HHHO 3-CF 3 4- CN 4-OCF 2 Br 0 HHHO 3-CF 3 4-CN 4-OCF 2 CHF 20 HHHO 3-CF 3 4-CN 4-OCF 3 0 HHHO 3-CF 3 4-CN 4-SCF 3 0 HHHO 3 -CF 3 4-CN 4-OSO 2 CF 3 0 HHHO 3-CF 3 4-CN 3,4-Cl 2 0 HHHO 3-OCF 2 CHF 2 4-F 4-Cl ────────── ──────────────────────────

【００５６】[0056]

【表２２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-OCF2CHF2 4-F 4-Br 0 H H H O 3-OCF2CHF2 4-F 4-CF3 0 H H H O 3-OCF2CHF2 4-F 4-OCHF2 0 H H H O 3-OCF2CHF2 4-F 4-OCF2Br 0 H H H O 3-OCF2CHF2 4-F 4-OCF2CHF2 0 H H H O 3-OCF2CHF2 4-F 4-OCF3 0 H H H O 3-OCF2CHF2 4-F 4-SCF3 0 H H H O 3-OCF2CHF2 4-F 4-OSO2CF3 0 H H H O 3-OCF2CHF2 4-F 3,4-Cl2 0 H H H O 4-F 4-F 4-Cl 0 H H H O 4-F 4-F 4-Br 0 H H H O 4-F 4-F 4-CF3 0 H H H O 4-F 4-F 4-OCHF2 0 H H H O 4-F 4-F 4-OCF2Br 0 H H H O 4-F 4-F 4-OCF2CHF2 0 H H H O 4-F 4-F 4-OCF3 0 H H H O 4-F 4-F 4-SCF3 0 H H H O 4-F 4-F 4-OSO2CF3 0 H H H O 4-F 4-F 3,4-Cl2 0 H H H O 3-CN 4-F 4-Cl 0 H H H O 3-CN 4-F 4-Br 0 H H H O 3-CN 4-F 4-CF3 0 H H H O 3-CN 4-F 4-OCHF2 ───────────────────────────────────[Table 22] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-OCF 2 CHF 2 4-F 4- Br 0 HHHO 3-OCF 2 CHF 2 4-F 4-CF 3 0 HHHO 3-OCF 2 CHF 2 4-F 4-OCHF 2 0 HHHO 3-OCF 2 CHF 2 4-F 4-OCF 2 Br 0 HHHO 3 -OCF 2 CHF 2 4-F 4-OCF 2 CHF 2 0 HHHO 3-OCF 2 CHF 2 4-F 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4-F 4-SCF 3 0 HHHO 3-OCF 2 CHF 2 4-F 4-OSO 2 CF 3 0 HHHO 3-OCF 2 CHF 2 4-F 3,4-Cl 2 0 HHHO 4-F 4-F 4-Cl 0 HHHO 4-F 4-F 4-Br 0 HHHO 4-F 4-F 4-CF 3 0 HHHO 4-F 4-F 4-OCHF 2 0 HHHO 4-F 4-F 4-OCF 2 Br 0 HHHO 4-F 4-F 4-OCF 2 CHF 20 HHHO 4-F 4-F 4-OCF 30 HHHO 4-F 4-F 4-SCF 30 HHHO 4-F 4-F 4-OSO 2 CF 3 0 HHHO 4-F 4-F 3,4 -Cl 2 0 HHHO 3-CN 4-F 4-Cl 0 HHHO 3-CN 4-F 4-Br 0 HHHO 3-CN 4-F 4-CF 3 0 HHHO 3-CN 4-F 4-OCHF 2 ─ ───────────────────────────────────

【００５７】[0057]

【表２３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CN 4-F 4-OCF2Br 0 H H H O 3-CN 4-F 4-OCF2CHF2 0 H H H O 3-CN 4-F 4-OCF3 0 H H H O 3-CN 4-F 4-SCF3 0 H H H O 3-CN 4-F 4-OSO2CF3 0 H H H O 3-CN 4-F 3,4-Cl2 0 H H H O 4-OCHF2 4-F 4-Cl 0 H H H O 4-OCHF2 4-F 4-Br 0 H H H O 4-OCHF2 4-F 4-CF3 0 H H H O 4-OCHF2 4-F 4-OCHF2 0 H H H O 4-OCHF2 4-F 4-OCF2Br 0 H H H O 4-OCHF2 4-F 4-OCF2CHF2 0 H H H O 4-OCHF2 4-F 4-OCF3 0 H H H O 4-OCHF2 4-F 4-SCF3 0 H H H O 4-OCHF2 4-F 4-OSO2CF3 0 H H H O 4-OCHF2 4-F 3,4-Cl2 0 H H H O 4-OCHF2 4-F 4-Cl 0 H H H O 3-F 2,4-F2 4-Br 0 H H H O 3-F 2,4-F2 4-CF3 0 H H H O 3-F 2,4-F2 4-OCHF2 0 H H H O 3-F 2,4-F2 4-OCF2Br 0 H H H O 3-F 2,4-F2 4-OCF2CHF2 0 H H H O 3-F 2,4-F2 4-OCF3 ───────────────────────────────────[Table 23] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CN 4-F 4-OCF 2 Br 0 HHHO 3-CN 4-F 4-OCF 2 CHF 2 0 HHHO 3-CN 4-F 4-OCF 3 0 HHHO 3-CN 4-F 4-SCF 3 0 HHHO 3-CN 4-F 4-OSO 2 CF 3 0 HHHO 3-CN 4-F 3,4-Cl 2 0 HHHO 4-OCHF 2 4-F 4-Cl 0 HHHO 4-OCHF 2 4-F 4-Br 0 HHHO 4-OCHF 2 4-F 4 -CF 3 0 HHHO 4-OCHF 2 4-F 4-OCHF 2 0 HHHO 4-OCHF 2 4-F 4-OCF 2 Br 0 HHHO 4-OCHF 2 4-F 4-OCF 2 CHF 2 0 HHHO 4-OCHF 2 4-F 4-OCF 30 HHHO 4-OCHF 2 4-F 4-SCF 3 0 HHHO 4-OCHF 2 4-F 4-OSO 2 CF 3 0 HHHO 4-OCHF 2 4-F 3,4-Cl 2 0 HHHO 4-OCHF 2 4-F 4-Cl 0 HHHO 3-F 2,4-F 2 4-Br 0 HHHO 3-F 2,4-F 2 4-CF 3 0 HHHO 3-F 2,4 -F 2 4-OCHF 20 HHHO 3-F 2,4-F 2 4-OCF 2 Br 0 HHHO 3-F 2,4-F 2 4-OCF 2 CHF 2 0 HHHO 3-F 2,4-F 2 4-OCF 3 ──────────────────────────────────

【００５８】[0058]

【表２４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 2,4-F2 4-SCF3 0 H H H O 3-F 2,4-F2 4-OSO2CF3 0 H H H O 3-F 2,4-F2 3,4-Cl2 0 H H H O 3-F 3,4-F2 4-Cl 0 H H H O 3-F 3,4-F2 4-Br 0 H H H O 3-F 3,4-F2 4-CF3 0 H H H O 3-F 3,4-F2 4-OCHF2 0 H H H O 3-F 3,4-F2 4-OCF2Br 0 H H H O 3-F 3,4-F2 4-OCF2CHF2 0 H H H O 3-F 3,4-F2 4-OCF3 0 H H H O 3-F 3,4-F2 4-SCF3 0 H H H O 3-F 3,4-F2 4-OSO2CF3 0 H H H O 3-F 3,4-F2 3,4-Cl2 0 H H H O 3,4-F2 4-F 4-Cl 0 H H H O 3,4-F2 4-F 4-Br 0 H H H O 3,4-F2 4-F 4-CF3 0 H H H O 3,4-F2 4-F 4-OCHF2 0 H H H O 3,4-F2 4-F 4-OCF2Br 0 H H H O 3,4-F2 4-F 4-OCF2CHF2 0 H H H O 3,4-F2 4-F 4-OCF3 0 H H H O 3,4-F2 4-F 4-SCF3 0 H H H O 3,4-F2 4-F 4-OSO2CF3 0 H H H O 3,4-F2 4-F 3,4-Cl2 ───────────────────────────────────[Table 24] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 2,4-F 2 4- SCF 3 0 HHHO 3-F 2,4-F 2 4-OSO 2 CF 3 0 HHHO 3-F 2,4-F 2 3,4-Cl 2 0 HHHO 3-F 3,4-F 2 4-Cl 0 HHHO 3-F 3,4-F 2 4-Br 0 HHHO 3-F 3,4-F 2 4-CF 3 0 HHHO 3-F 3,4-F 2 4-OCHF 2 0 HHHO 3-F 3 , 4-F 2 4-OCF 2 Br 0 HHHO 3-F 3,4-F 2 4-OCF 2 CHF 2 0 HHHO 3-F 3,4-F 2 4-OCF 3 0 HHHO 3-F 3,4 -F 2 4-SCF 3 0 HHHO 3-F 3,4-F 2 4-OSO 2 CF 3 0 HHHO 3-F 3,4-F 2 3,4-Cl 2 0 HHHO 3,4-F 2 4 -F 4-Cl 0 HHHO 3,4-F 2 4-F 4-Br 0 HHHO 3,4-F 2 4-F 4-CF 3 0 HHHO 3,4-F 2 4-F 4-OCHF 20 HHHO 3,4-F 2 4-F 4-OCF 2 Br 0 HHHO 3,4-F 2 4-F 4-OCF 2 CHF 2 0 HHHO 3,4-F 2 4-F 4-OCF 3 0 HHHO 3 , 4-F 2 4-F 4-SCF 3 0 HHHO 3,4-F 2 4-F 4-OSO 2 CF 3 0 HHHO 3,4-F 2 4-F 3,4-Cl 2 ──── ───────────────────────────── ─

【００５９】[0059]

【表２５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 H 4-Cl 0 H H H O 3-CF3 2-F 4-CF3 0 H H H O 3-CF3 3-F 4-OCF3 0 H H H O 3-CF3 2-Cl 4-Cl 0 H H H O 3-CF3 3-Cl 4-CF3 0 H H H O 3-CF3 4-Cl 4-OCF3 0 H H H O 3-CF3 3-Br 4-Cl 0 H H H O 3-CF3 4-Br 4-CF3 0 H H H O 3-CF3 3-I 4-OCF3 0 H H H O 3-CF3 4-I 4-Cl 0 H H H O 3-CF3 4-CH3 4-CF3 0 H H H O 3-CF3 4-CH2CH3 4-OCF3 0 H H H O 3-CF3 4-CH(CH3)2 4-Cl 0 H H H O 3-CF3 4-CH2CH2CH2CH3 4-CF3 0 H H H O 3-CF3 4-C(CH3)3 4-OCF3 0 H H H O 3-CF3 4-CH2CH=CH2 4-Cl 0 H H H O 3-CF3 4-Q1 4-CF3 0 H H H O 3-CF3 4-Q2 4-OCF3 0 H H H O 3-CF3 4-Q3 4-Cl 0 H H H O 3-CF3 4-Q4 4-CF3 0 H H H O 3-CF3 4-CHF2 4-OCF3 0 H H H O 3-CF3 4-CH2Br 4-Cl 0 H H H O 3-CF3 4-CH2Cl 4-CF3 ───────────────────────────────────[Table 25] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 H 4-Cl 0 HHHO 3 -CF 3 2-F 4-CF 30 HHHO 3-CF 3 3-F 4-OCF 30 HHHO 3-CF 3 2-Cl 4-Cl 0 HHHO 3-CF 3 3-Cl 4-CF 30 HHHO 3-CF 3 4-Cl 4-OCF 3 0 HHHO 3-CF 3 3-Br 4-Cl 0 HHHO 3-CF 3 4-Br 4-CF 3 0 HHHO 3-CF 3 3-I 4-OCF 3 0 HHHO 3-CF 3 4-I 4-Cl 0 HHHO 3-CF 3 4-CH 3 4-CF 3 0 HHHO 3-CF 3 4-CH 2 CH 3 4-OCF 3 0 HHHO 3-CF 3 4-CH (CH 3 ) 2 4-Cl 0 HHHO 3-CF 3 4-CH 2 CH 2 CH 2 CH 3 4-CF 3 0 HHHO 3-CF 3 4-C (CH 3 ) 3 4-OCF 3 0 HHHO 3- CF 3 4-CH 2 CH = CH 2 4-Cl 0 HHHO 3-CF 3 4-Q1 4-CF 3 0 HHHO 3-CF 3 4-Q2 4-OCF 3 0 HHHO 3-CF 3 4-Q3 4- Cl 0 HHHO 3-CF 3 4-Q4 4-CF 30 HHHO 3-CF 3 4-CHF 2 4-OCF 30 HHHO 3-CF 3 4-CH 2 Br 4-Cl 0 HHHO 3-CF 3 4- CH 2 Cl 4-CF 3 ──────────────────────────────── ──

【００６０】[0060]

【表２６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 2-CF3 4-Cl 0 H H H O 3-CF3 3-CF3 4-CF3 0 H H H O 3-CF3 4-CF3 4-OCF3 0 H H H O 3-CF3 4-CH=C(Cl)CF3 4-Cl 0 H H H O 3-CF3 4-(Q4-1-Cl) 4-CF3 0 H H H O 3-CF3 4-CH2CN 4-OCF3 0 H H H O 3-CF3 4-CH2OH 4-Cl 0 H H H O 3-CF3 4-CH2CO2H 4-CF3 0 H H H O 3-CF3 4-OCH3 4-OCF3 0 H H H O 3-CF3 4-OCH2CH3 4-Cl 0 H H H O 3-CF3 4-OCH(CH3)2 4-CF3 0 H H H O 3-CF3 4-OCH2CH2CH2CH3 4-OCF3 0 H H H O 3-CF3 4-OC(CH3)3 4-Cl 0 H H H O 3-CF3 4-O(Q4) 4-CF3 0 H H H O 3-CF3 4-OCHF2 4-OCF3 0 H H H O 3-CF3 4-OCF2Br 4-Cl 0 H H H O 3-CF3 2-OCF3 4-CF3 0 H H H O 3-CF3 3-OCF3 4-OCF3 0 H H H O 3-CF3 4-OCF3 4-Cl 0 H H H O 3-CF3 4-OCH2CF3 4-CF3 0 H H H O 3-CF3 4-OCF2CF3 4-OCF3 0 H H H O 3-CF3 4-OCF2CHF2 4-Cl 0 H H H O 3-CF3 4-OCF2CHFCl 4-CF3 ───────────────────────────────────[Table 26] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 2-CF 3 4-Cl 0 HHHO 3-CF 3 3-CF 3 4-CF 3 0 HHHO 3-CF 3 4-CF 3 4-OCF 3 0 HHHO 3-CF 3 4-CH = C (Cl) CF 3 4-Cl 0 HHHO 3 -CF 3 4- (Q4-1-Cl) 4-CF 3 0 HHHO 3-CF 3 4-CH 2 CN 4-OCF 3 0 HHHO 3-CF 3 4-CH 2 OH 4-Cl 0 HHHO 3-CF 3 4-CH 2 CO 2 H 4-CF 3 0 HHHO 3-CF 3 4-OCH 3 4-OCF 3 0 HHHO 3-CF 3 4-OCH 2 CH 3 4-Cl 0 HHHO 3-CF 3 4-OCH (CH 3 ) 2 4-CF 3 0 HHHO 3-CF 3 4-OCH 2 CH 2 CH 2 CH 3 4-OCF 3 0 HHHO 3-CF 3 4-OC (CH 3 ) 3 4-Cl 0 HHHO 3- CF 3 4-O (Q4) 4-CF 3 0 HHHO 3-CF 3 4-OCHF 2 4-OCF 30 HHHO 3-CF 3 4-OCF 2 Br 4-Cl 0 HHHO 3-CF 3 2-OCF 3 4-CF 3 HOH 3-CF 3 3-OCF 3 4-OCF 3 0 HHHO 3-CF 3 4-OCF 3 4-Cl 0 HHHO 3-CF 3 4-OCH 2 CF 3 4-CF 3 0 HHHO 3 -CF 3 4-OCF 2 CF 3 4-OCF 3 0 HHHO 3-CF 3 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-CF 3 4-OCF 2 CHFCl 4-CF 3 ─── ───────────────────────────────

【００６１】[0061]

【表２７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-OCF2CHFBr 4-Cl 0 H H H O 3-CF3 4-OCF2CF2CF3 4-CF3 0 H H H O 3-CF3 4-OCH2CH=CHCl 4-OCF3 0 H H H O 3-CF3 4-O(Q4-2,2-Cl2) 4-Cl 0 H H H O 3-CF3 4-SCH3 4-CF3 0 H H H O 3-CF3 4-SCHF2 4-OCF3 0 H H H O 3-CF3 4-SCF2Br 4-Cl 0 H H H O 3-CF3 4-SCF3 4-CF3 0 H H H O 3-CF3 4-SCF2CHF2 4-OCF3 0 H H H O 3-CF3 4-SOCH3 4-Cl 0 H H H O 3-CF3 4-SOCF3 4-CF3 0 H H H O 3-CF3 4-SOCF2CHF2 4-OCF3 0 H H H O 3-CF3 4-SO2CH3 4-Cl 0 H H H O 3-CF3 4-SO2CF3 4-CF3 0 H H H O 3-CF3 4-SO2CHF2 4-OCF3 0 H H H O 3-CF3 4-SO2CF2Br 4-Cl 0 H H H O 3-CF3 4-CH2OCH3 4-CF3 0 H H H O 3-CF3 4-OCF2CHFOCF3 4-OCF3 0 H H H O 3-CF3 4-CH2SCH3 4-Cl 0 H H H O 3-CF3 4-CH2COCH3 4-CF3 0 H H H O 3-CF3 4-CH2CO2CH3 4-OCF3 0 H H H O 3-CF3 4-OCO2CH3 4-Cl 0 H H H O 3-CF3 4-OCOCH3 4-CF3 ───────────────────────────────────[Table 27] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-OCF 2 CHFBr 4- Cl 0 HHHO 3-CF 3 4-OCF 2 CF 2 CF 3 4-CF 3 0 HHHO 3-CF 3 4-OCH 2 CH = CHCl 4-OCF 3 0 HHHO 3-CF 3 4-O (Q4-2, 2-Cl 2 ) 4-Cl 0 HHHO 3-CF 3 4-SCH 3 4-CF 3 0 HHHO 3-CF 3 4-SCHF 2 4-OCF 3 0 HHHO 3-CF 3 4-SCF 2 Br 4-Cl 0 HHHO 3-CF 3 4-SCF 3 4-CF 3 0 HHHO 3-CF 3 4-SCF 2 CHF 2 4-OCF 3 0 HHHO 3-CF 3 4-SOCH 3 4-Cl 0 HHHO 3-CF 3 4 -SOCF 3 4-CF 3 0 HHHO 3-CF 3 4-SOCF 2 CHF 2 4-OCF 3 0 HHHO 3-CF 3 4-SO 2 CH 3 4-Cl 0 HHHO 3-CF 3 4-SO 2 CF 3 4-CF 30 HHHO 3-CF 3 4-SO 2 CHF 2 4-OCF 30 HHHO 3-CF 3 4-SO 2 CF 2 Br 4-Cl 0 HHHO 3-CF 3 4-CH 2 OCH 3 4- CF 3 0 HHHO 3-CF 3 4-OCF 2 CHFOCF 3 4-OCF 3 0 HHHO 3-CF 3 4-CH 2 SCH 3 4-Cl 0 HHHO 3-CF 3 4-CH 2 COCH 3 4-CF 3 0 HHHO 3-CF 3 4-CH 2 CO 2 CH 3 4-OCF 3 0 HHHO 3-CF 3 4-OCO 2 CH 3 4-Cl 0 HH HO 3-CF 3 4-OCOCH 3 4-CF 3 ────────────────────────────────────

【００６２】[0062]

【表２８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-COCH3 4-Cl 0 H H H O 3-CF3 4-COCF3 4-CF3 0 H H H O 3-CF3 4-CO2CH2CH3 4-OCF3 0 H H H O 3-CF3 4-CO2C(CH3)3 4-Cl 0 H H H O 3-CF3 4-CO2CH2CF3 4-CF3 0 H H H O 3-CF3 4-OCH2CO2CH3 4-OCF3 0 H H H O 3-CF3 4-NO2 4-Cl 0 H H H O 3-CF3 4-OH 4-CF3 0 H H H O 3-CF3 4-CO2H 4-OCF3 0 H H H O 3-CF3 4-SCN 4-Cl 0 H H H O 3-CF3 4-OSO2CH3 4-CF3 0 H H H O 3-CF3 4-OSO2CF3 4-OCF3 0 H H H O 3-CF3 4-CSCH3 4-Cl 0 H H H O 3-CF3 4-NH2 4-CF3 0 H H H O 3-CF3 4-N(CH3)2 4-OCF3 0 H H H O 3-CF3 4-N(CH3)CH2CH=CH2 4-Cl 0 H H H O 3-CF3 4-CON(CH3)2 4-CF3 0 H H H O 3-CF3 4-OCON(CH3)2 4-OCF3 0 H H H O 3-CF3 4-NHCOCH3 4-Cl 0 H H H O 3-CF3 4-SO2N(CH3)2 4-CF3 0 H H H O 3-CF3 4-Si(CH3)3 4-OCF3 0 H H H O 3-CF3 4-C6H5 4-Cl 0 H H H O 3-CF3 4-(C6H4-4-Cl) 4-CF3 ───────────────────────────────────[Table 28] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-COCH 3 4-Cl 0 HHHO 3-CF 3 4-COCF 3 4-CF 3 0 HHHO 3-CF 3 4-CO 2 CH 2 CH 3 4-OCF 3 0 HHHO 3-CF 3 4-CO 2 C (CH 3 ) 3 4- Cl 0 HHHO 3-CF 3 4-CO 2 CH 2 CF 3 4-CF 3 0 HHHO 3-CF 3 4-OCH 2 CO 2 CH 3 4-OCF 3 0 HHHO 3-CF 3 4-NO 2 4-Cl 0 HHHO 3-CF 3 4-OH 4-CF 3 0 HHHO 3-CF 3 4-CO 2 H 4-OCF 3 0 HHHO 3-CF 3 4-SCN 4-Cl 0 HHHO 3-CF 3 4-OSO 2 CH 3 4-CF 3 0 HHHO 3-CF 3 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-CF 3 4-CSCH 3 4-Cl 0 HHHO 3-CF 3 4-NH 2 4-CF 3 0 HHHO 3-CF 3 4-N (CH 3 ) 2 4-OCF 3 0 HHHO 3-CF 3 4-N (CH 3 ) CH 2 CH = CH 2 4-Cl 0 HHHO 3-CF 3 4-CON (CH 3) 2 4-CF 3 0 HHHO 3-CF 3 4-OCON (CH 3) 2 4-OCF 3 0 HHHO 3-CF 3 4-NHCOCH 3 4-Cl 0 HHHO 3-CF 3 4-SO 2 N ( CH 3 ) 2 4-CF 3 0 HHHO 3-CF 3 4-Si (CH 3 ) 3 4-OCF 3 0 HHHO 3-CF 3 4-C 6 H 5 4-Cl 0 HHHO 3-CF 3 4 -(C 6 H 4 -4-Cl) 4-CF 3 ────────────────────────────────────

【００６３】[0063]

【表２９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 4-OC6H5 4-Cl 0 H H H O 3-CF3 4-O(C6H4-4-CF3) 4-CF3 0 H H H O 3-CF3 3-O(C6H4-4-CF3) 4-OCF3 0 H H H O 3-CF3 4-S(C6H4-4-CF3) 4-Cl 0 H H H O 3-CF3 4-SO2C6H5 4-CF3 0 H H H O 3-CF3 4-NH(C6H4-4-Cl) 4-OCF3 0 H H H O 3-CF3 4-CH2C6H5 4-Cl 0 H H H O 3-CF3 4-COC6H5 4-CF3 0 H H H O 3-CF3 4-OCH2(C6H4-4-CF3) 4-OCF3 0 H H H O 3-CF3 4-CH2OC6H5 4-Cl 0 H H H O 3-CF3 4-NHCH2C6H5 4-CF3 0 H H H O 3-CF3 4-CH2CH2C6H5 4-OCF3 0 H H H O 3-CF3 4-N=NC6H5 4-Cl 0 H H H O 3-CF3 4-CH=CHC6H5 4-CF3 0 H H H O 3-CF3 2-CH=CH-CH=CH-3 4-OCF3 0 H H H O 3-CF3 3-CH=CH-CH=CH-4 4-Cl 0 H H H O 3-CF3 3-OCH2O-4 4-CF3 0 H H H O 3-CF3 3-OCF2O-4 4-OCF3 0 H H H O 3-CF3 3-OCH2CH2O-4 4-Cl 0 H H H O 3-CF3 3-OCF2CF2O-4 4-CF3 0 H H H O 3-CF3 3-OCF2CF2-4 4-OCF3 0 H H H O 3-CF3 3-CF2CF2O-4 4-Cl 0 H H H O 3-CF3 4-NHSO2CH3 4-CF3 ───────────────────────────────────[Table 29] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 4-OC 6 H 5 4 -Cl 0 HHHO 3-CF 3 4-O (C 6 H 4 -4-CF 3 ) 4-CF 3 0 HHHO 3-CF 3 3-O (C 6 H 4 -4-CF 3 ) 4-OCF 3 0 HHHO 3-CF 3 4-S (C 6 H 4 -4-CF 3 ) 4-Cl 0 HHHO 3-CF 3 4-SO 2 C 6 H 5 4-CF 3 0 HHHO 3-CF 3 4-NH (C 6 H 4 -4-Cl) 4-OCF 3 0 HHHO 3-CF 3 4-CH 2 C 6 H 5 4-Cl 0 HHHO 3-CF 3 4-COC 6 H 5 4-CF 3 0 HHHO 3 -CF 3 4-OCH 2 (C 6 H 4 -4-CF 3 ) 4-OCF 3 0 HHHO 3-CF 3 4-CH 2 OC 6 H 5 4-Cl 0 HHHO 3-CF 3 4-NHCH 2 C 6 H 5 4-CF 30 HHHO 3-CF 3 4-CH 2 CH 2 C 6 H 5 4-OCF 30 HHHO 3-CF 3 4-N = NC 6 H 5 4-Cl 0 HHHO 3-CF 3 4-CH = CHC 6 H 5 4-CF 3 0 HHHO 3-CF 3 2-CH = CH-CH = CH-3 4-OCF 3 0 HHHO 3-CF 3 3-CH = CH-CH = CH-4 4-Cl 0 HHHO 3-CF 3 3-OCH 2 O-4 4-CF 3 0 HHHO 3-CF 3 3-OCF 2 O-4 4-OCF 3 0 HHHO 3-CF 3 3-OCH 2 CH 2 O -4 4-Cl 0 HHHO 3-CF 3 3-OCF 2 CF 2 O-4 4-C F 3 0 HHHO 3-CF 3 3-OCF 2 CF 2 -4 4-OCF 3 0 HHHO 3-CF 3 3-CF 2 CF 2 O-4 4-Cl 0 HHHO 3-CF 3 4-NHSO 2 CH 3 4-CF 3 ───────────────────────────────────

【００６４】[0064]

【表３０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 2,3-F2 4-Cl 0 H H H O 3-CF3 2,4-F2 4-CF3 0 H H H O 3-CF3 2,5-F2 4-OCF3 0 H H H O 3-CF3 2,6-F2 4-Cl 0 H H H O 3-CF3 3,4-F2 4-CF3 0 H H H O 3-CF3 3,5-F2 4-OCF3 0 H H H O 3-CF3 2,4-Cl2 4-Cl 0 H H H O 3-CF3 3,4-Cl2 4-CF3 0 H H H O 3-CF3 3,4-Br2 4-OCF3 0 H H H O 3-CF3 2,4-I2 4-Cl 0 H H H O 3-CF3 2,4-(CH3)2 4-CF3 0 H H H O 3-CF3 3,4-(OCH3)2 4-OCF3 0 H H H O 3-CF3 2-F-4-Cl 4-Cl 0 H H H O 3-CF3 2-F-4-Br 4-CF3 0 H H H O 3-CF3 2-F-4-CF3 4-OCF3 0 H H H O 3-CF3 2-F-4-OCHF2 4-Cl 0 H H H O 3-CF3 2-F-4-OSO2CF3 4-CF3 0 H H H O 3-CF3 2-F-4-O(C6H4-4-Cl) 4-OCF3 0 H H H O 3-CF3 2-F-4-O(Q5-5-CF3) 4-Cl 0 H H H O 3-CF3 3-Cl-4-CF3 4-CF3 0 H H H O 3-CF3 3-F-4-OCF3 4-OCF3 0 H H H O 3-CF3 3,4-(CF3)2 4-Cl 0 H H H O 3-CF3 3,4-(OCF3)2 4-CF3 ──────────────────────────────────[Table 30] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 2,3-F 2 4 -Cl 0 HHHO 3-CF 3 2,4-F 2 4-CF 3 0 HHHO 3-CF 3 2,5-F 2 4-OCF 3 0 HHHO 3-CF 3 2,6-F 2 4-Cl 0 HHHO 3-CF 3 3,4-F 2 4-CF 3 0 HHHO 3-CF 3 3,5-F 2 4-OCF 3 0 HHHO 3-CF 3 2,4-Cl 2 4-Cl 0 HHHO 3- CF 3 3,4-Cl 2 4-CF 3 0 HHHO 3-CF 3 3,4-Br 2 4-OCF 3 0 HHHO 3-CF 3 2,4-I 2 4-Cl 0 HHHO 3-CF 3 2 , 4- (CH 3 ) 2 4-CF 3 0 HHHO 3-CF 3 3,4- (OCH 3 ) 2 4-OCF 3 0 HHHO 3-CF 3 2-F-4-Cl 4-Cl 0 HHHO 3 -CF 3 2-F-4-Br 4-CF 3 0 HHHO 3-CF 3 2-F-4-CF 3 4-OCF 3 0 HHHO 3-CF 3 2-F-4-OCHF 2 4-Cl 0 HHHO 3-CF 3 2-F-4-OSO 2 CF 3 4-CF 3 0 HHHO 3-CF 3 2-F-4-O (C 6 H 4 -4-Cl) 4-OCF 3 0 HHHO 3- CF 3 2-F-4-O (Q5-5-CF 3 ) 4-Cl 0 HHHO 3-CF 3 3-Cl-4-CF 3 4-CF 3 0 HHHO 3-CF 3 3-F-4- OCF 3 4-OCF 3 0 HHHO 3-CF 3 3,4- (CF 3) 2 4-Cl 0 HHHO 3-CF 3 3,4- (OCF 3) 2 4-CF 3 ─ ────────────────────────────────

【００６５】[0065]

【表３１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-CF3 3-CN 4-Cl 0 H H H O 3-CF3 2-Cl-4-CN 4-CF3 0 H H H O 3-CF3 3-Cl-4-CN 4-OCF3 0 H H H O 3-CF3 2-CH3-4-CN 4-Cl 0 H H H O 3-CF3 3-CH3-4-CN 4-CF3 0 H H H O 3-CF3 3,4-(CN)2 4-OCF3 0 H H H O 3-CF3 2,5-F2-4-Cl 4-Cl 0 H H H O 3-CF3 3,5-F2-4-CF3 4-CF3 0 H H H O 3-CF3 2,3,4-F3 4-OCF3 0 H H H O 3-CF3 2,4,5-F3 4-Cl 0 H H H O 3-CF3 3,4,5-F3 4-CF3 0 H H H O 3-CF3 2,3,4-Cl3 4-OCF3 0 H H H O 3-CF3 2,4,5-Cl3 4-Cl 0 H H H O 3-CF3 2,4,6-Cl3 4-CF3 0 H H H O 3-CF3 2-F-4,5-Cl2 4-OCF3 0 H H H O 3-CF3 3-Cl-4-F 4-Cl 0 H H H O 3-CF3 2-F-4-OCHF2-5-Cl 4-CF3 0 H H H O 3-CF3 2,3,4,5-F4 4-OCF3 0 H H H O 3-CF3 2,3,5,6-F4 4-Cl 0 H H H O 3-CF3 2,4-F2-3,5-Cl2 4-CF3 0 H H H O 3-CF3 2,3,4,5,6-F5 4-OCF3 0 H H H O 3-CF3 2,3,5,6-F4-4-CN 4-Cl 0 H H H O 3-CF3 4-NHCONHCH3 4-CF3 ───────────────────────────────────[Table 31] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-CF 3 3-CN 4-Cl 0 HHHO 3-CF 3 2-Cl-4-CN 4-CF 3 0 HHHO 3-CF 3 3-Cl-4-CN 4-OCF 3 0 HHHO 3-CF 3 2-CH 3 -4-CN 4-Cl 0 HHHO 3-CF 3 3-CH 3 -4-CN 4-CF 3 0 HHHO 3-CF 3 3,4- (CN) 2 4-OCF 3 0 HHHO 3-CF 3 2,5-F 2 -4 -Cl 4-Cl 0 HHHO 3-CF 3 3,5-F 2 -4-CF 3 4-CF 3 0 HHHO 3-CF 3 2,3,4-F 3 4-OCF 3 0 HHHO 3-CF 3 2,4,5-F 3 4-Cl 0 HHHO 3-CF 3 3,4,5-F 3 4-CF 3 0 HHHO 3-CF 3 2,3,4-Cl 3 4-OCF 3 0 HHHO 3 -CF 3 2,4,5-Cl 3 4-Cl 0 HHHO 3-CF 3 2,4,6-Cl 3 4-CF 3 0 HHHO 3-CF 3 2-F-4,5-Cl 2 4- OCF 3 0 HHHO 3-CF 3 3-Cl-4-F 4-Cl 0 HHHO 3-CF 3 2-F-4-OCHF 2 -5-Cl 4-CF 3 0 HHHO 3-CF 3 2,3, 4,5-F 4 4-OCF 3 0 HHHO 3-CF 3 2,3,5,6-F 4 4-Cl 0 HHHO 3-CF 3 2,4-F 2 -3,5-Cl 2 4- CF 3 0 HHHO 3-CF 3 2,3,4,5,6-F 5 4-OCF 30 HHHO 3-CF 3 2,3,5,6-F 4 -4-CN 4-Cl 0 HHHO 3 -CF 3 4-NHCONH CH 3 4-CF 3 ────────────────────────────────────

【００６６】[0066]

【表３２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-F 3-F 4-Cl 0 H H H O 3-F 3-Cl 4-CF3 0 H H H O 3-F 3-Br 4-OCF3 0 H H H O 3-F 4-CN 4-Cl 0 H H H O 3-F 4-NO2 4-CF3 0 H H H O 3-F 4-CH3 4-OCF3 0 H H H O 3-F 4-CF3 4-Cl 0 H H H O 3-F 4-OCH2CH3 4-CF3 0 H H H O 3-F 4-OCHF2 4-OCF3 0 H H H O 3-F 4-OCH2CF3 4-Cl 0 H H H O 3-F 4-OCF2Br 4-CF3 0 H H H O 3-F 4-OCF2CHF2 4-OCF3 0 H H H O 3-F 4-OSO2CF3 4-Cl 0 H H H O 3-F 4-SCHF2 4-CF3 0 H H H O 3-F 4-SCF3 4-OCF3 0 H H H O 3-F 4-SCH3 4-Cl 0 H H H O 3-F 4-SOCH3 4-CF3 0 H H H O 3-F 4-SO2CH3 4-OCF3 0 H H H O 3-F 4-OSO2CH3 4-Cl 0 H H H O 3-F 4-NHCOCH3 4-CF3 0 H H H O 3-F 4-NHSO2CH3 4-OCF3 0 H H H O 3-F 2,4-Cl2 4-Cl 0 H H H O 3-F 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 32] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-F 3-F 4-Cl 0 HHHO 3-F 3-Cl 4-CF 30 HHHO 3-F 3-Br 4-OCF 30 HHHO 3-F 4-CN 4-Cl 0 HHHO 3-F 4-NO 2 4-CF 30 HHHO 3- F 4-CH 3 4-OCF 3 0 HHHO 3-F 4-CF 3 4-Cl 0 HHHO 3-F 4-OCH 2 CH 3 4-CF 3 0 HHHO 3-F 4-OCHF 2 4-OCF 3 0 HHHO 3-F 4-OCH 2 CF 3 4-Cl 0 HHHO 3-F 4-OCF 2 Br 4-CF 3 0 HHHO 3-F 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-F 4-OSO 2 CF 3 4-Cl 0 HHHO 3-F 4-SCHF 2 4-CF 3 0 HHHO 3-F 4-SCF 3 4-OCF 3 0 HHHO 3-F 4-SCH 3 4-Cl 0 HHHO 3-F 4 -SOCH 3 4-CF 3 0 HHHO 3-F 4-SO 2 CH 3 4-OCF 3 0 HHHO 3-F 4-OSO 2 CH 3 4-Cl 0 HHHO 3-F 4-NHCOCH 3 4-CF 3 0 HHHO 3-F 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3-F 2,4-Cl 2 4-Cl 0 HHHO 3-F 3-OCF 2 O-4 4-CF 3 ─────── ─────────────────────────────

【００６７】[0067]

【表３３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-OCHF2 3-F 4-Cl 0 H H H O 3-OCHF2 4-Cl 4-CF3 0 H H H O 3-OCHF2 4-Br 4-OCF3 0 H H H O 3-OCHF2 4-CN 4-Cl 0 H H H O 3-OCHF2 4-NO2 4-CF3 0 H H H O 3-OCHF2 4-CH3 4-OCF3 0 H H H O 3-OCHF2 4-CF3 4-Cl 0 H H H O 3-OCHF2 4-OCH2CH3 4-CF3 0 H H H O 3-OCHF2 4-OCHF2 4-OCF3 0 H H H O 3-OCHF2 4-OCH2CF3 4-Cl 0 H H H O 3-OCHF2 4-OCF2Br 4-CF3 0 H H H O 3-OCHF2 4-OCF2CHF2 4-OCF3 0 H H H O 3-OCHF2 4-OSO2CF3 4-Cl 0 H H H O 3-OCHF2 4-SCHF2 4-CF3 0 H H H O 3-OCHF2 4-SCF3 4-OCF3 0 H H H O 3-OCHF2 4-SCH3 4-Cl 0 H H H O 3-OCHF2 4-SOCH3 4-CF3 0 H H H O 3-OCHF2 4-SO2CH3 4-OCF3 0 H H H O 3-OCHF2 4-OSO2CH3 4-Cl 0 H H H O 3-OCHF2 4-NHCOCH3 4-CF3 0 H H H O 3-OCHF2 4-NHSO2CH3 4-OCF3 0 H H H O 3-OCHF2 2,4-Cl2 4-Cl 0 H H H O 3-OCHF2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 33] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-OCHF 2 3-F 4-Cl 0 HHHO 3-OCHF 2 4-Cl 4-CF 30 HHHO 3-OCHF 2 4-Br 4-OCF 30 HHHO 3-OCHF 2 4-CN 4-Cl 0 HHHO 3-OCHF 2 4-NO 2 4-CF 3 0 HHHO 3-OCHF 2 4-CH 3 4-OCF 3 0 HHHO 3-OCHF 2 4-CF 3 4-Cl 0 HHHO 3-OCHF 2 4-OCH 2 CH 3 4-CF 3 0 HHHO 3-OCHF 2 4-OCHF 2 4-OCF 30 HHHO 3-OCHF 2 4-OCH 2 CF 3 4-Cl 0 HHHO 3-OCHF 2 4-OCF 2 Br 4-CF 3 0 HHHO 3-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-OCHF 2 4-OSO 2 CF 3 4-Cl 0 HHHO 3-OCHF 2 4-SCHF 2 4-CF 3 0 HHHO 3-OCHF 2 4-SCF 3 4-OCF 3 0 HHHO 3 -OCHF 2 4-SCH 3 4-Cl 0 HHHO 3-OCHF 2 4-SOCH 3 4-CF 3 0 HHHO 3-OCHF 2 4-SO 2 CH 3 4-OCF 3 0 HHHO 3-OCHF 2 4-OSO 2 CH 3 4-Cl 0 HHHO 3 -OCHF 2 4-NHCOCH 3 4-CF 3 0 HHHO 3-OCHF 2 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3-OCHF 2 2,4-Cl 2 4-Cl 0 HHHO 3-OCHF 2 3- OCF 2 O-4 4-CF 3 ── ────────────────────────────────

【００６８】[0068]

【表３４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-OCHF2 3-F 4-Cl 0 H H H O 4-OCHF2 4-Cl 4-CF3 0 H H H O 4-OCHF2 4-Br 4-OCF3 0 H H H O 4-OCHF2 4-CN 4-Cl 0 H H H O 4-OCHF2 4-NO2 4-CF3 0 H H H O 4-OCHF2 4-CH3 4-OCF3 0 H H H O 4-OCHF2 4-CF3 4-Cl 0 H H H O 4-OCHF2 4-OCH2CH3 4-CF3 0 H H H O 4-OCHF2 4-OCHF2 4-OCF3 0 H H H O 4-OCHF2 4-OCH2CF3 4-Cl 0 H H H O 4-OCHF2 4-OCF2Br 4-CF3 0 H H H O 4-OCHF2 4-OCF2CHF2 4-OCF3 0 H H H O 4-OCHF2 4-OSO2CF3 4-Cl 0 H H H O 4-OCHF2 4-SCHF2 4-CF3 0 H H H O 4-OCHF2 4-SCF3 4-OCF3 0 H H H O 4-OCHF2 4-SCH3 4-Cl 0 H H H O 4-OCHF2 4-SOCH3 4-CF3 0 H H H O 4-OCHF2 4-SO2CH3 4-OCF3 0 H H H O 4-OCHF2 4-OSO2CH3 4-Cl 0 H H H O 4-OCHF2 4-NHCOCH3 4-CF3 0 H H H O 4-OCHF2 4-NHSO2CH3 4-OCF3 0 H H H O 4-OCHF2 2,4-Cl2 4-Cl 0 H H H O 4-OCHF2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 34] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-OCHF 2 3-F 4-Cl 0 HHHO 4-OCHF 2 4-Cl 4-CF 30 HHHO 4-OCHF 2 4-Br 4-OCF 30 HHHO 4-OCHF 2 4-CN 4-Cl 0 HHHO 4-OCHF 2 4-NO 2 4-CF 3 0 HHHO 4-OCHF 2 4-CH 3 4-OCF 3 0 HHHO 4-OCHF 2 4-CF 3 4-Cl 0 HHHO 4-OCHF 2 4-OCH 2 CH 3 4-CF 3 0 HHHO 4-OCHF 2 4-OCHF 2 4-OCF 30 HHHO 4-OCHF 2 4-OCH 2 CF 3 4-Cl 0 HHHO 4-OCHF 2 4-OCF 2 Br 4-CF 3 0 HHHO 4-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 4-OCHF 2 4-OSO 2 CF 3 4-Cl 0 HHHO 4-OCHF 2 4-SCHF 2 4-CF 3 0 HHHO 4-OCHF 2 4-SCF 3 4-OCF 3 0 HHHO 4 -OCHF 2 4-SCH 3 4-Cl 0 HHHO 4-OCHF 2 4-SOCH 3 4-CF 3 0 HHHO 4-OCHF 2 4-SO 2 CH 3 4-OCF 3 0 HHHO 4-OCHF 2 4-OSO 2 CH 3 4-Cl 0 HHHO 4-OCHF 2 4-NHCOCH 3 4-CF 3 0 HHHO 4-OCHF 2 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 4-OCHF 2 2,4-Cl 2 4-Cl 0 HHHO 4-OCHF 2 3- OCF 2 O-4 4-CF 3 ── ────────────────────────────────

【００６９】[0069]

【表３５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl H 4-Cl 0 H H H O 3-Cl 4-Cl 4-CF3 0 H H H O 3-Cl 4-Br 4-OCF3 0 H H H O 3-Cl 4-CN 4-Cl 0 H H H O 3-Cl 4-NO2 4-CF3 0 H H H O 3-Cl 4-CH3 4-OCF3 0 H H H O 3-Cl 4-CF3 4-Cl 0 H H H O 3-Cl 4-OCH2CH3 4-CF3 0 H H H O 3-Cl 4-OCHF2 4-OCF3 0 H H H O 3-Cl 4-OCH2CF3 4-Cl 0 H H H O 3-Cl 4-OCF2Br 4-CF3 0 H H H O 3-Cl 4-OCF2CHF2 4-OCF3 0 H H H O 3-Cl 4-OSO2CF3 4-Cl 0 H H H O 3-Cl 4-SCHF2 4-CF3 0 H H H O 3-Cl 4-SCF3 4-OCF3 0 H H H O 3-Cl 4-SCH3 4-Cl 0 H H H O 3-Cl 4-SOCH3 4-CF3 0 H H H O 3-Cl 4-SO2CH3 4-OCF3 0 H H H O 3-Cl 4-OSO2CH3 4-Cl 0 H H H O 3-Cl 4-NHCOCH3 4-CF3 0 H H H O 3-Cl 4-NHSO2CH3 4-OCF3 0 H H H O 3-Cl 2,4-Cl2 4-Cl 0 H H H O 3-Cl 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 35] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl H 4-Cl 0 HHHO 3- Cl 4-Cl 4-CF 30 HHHO 3-Cl 4-Br 4-OCF 30 HHHO 3-Cl 4-CN 4-Cl 0 HHHO 3-Cl 4-NO 2 4-CF 30 HHHO 3-Cl 4 -CH 3 4-OCF 3 0 HHHO 3-Cl 4-CF 3 4-Cl 0 HHHO 3-Cl 4-OCH 2 CH 3 4-CF 3 0 HHHO 3-Cl 4-OCHF 2 4-OCF 3 0 HHHO 3 -Cl 4-OCH 2 CF 3 4-Cl 0 HHHO 3-Cl 4-OCF 2 Br 4-CF 3 0 HHHO 3-Cl 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-Cl 4-OSO 2 CF 3 4-Cl 0 HHHO 3-Cl 4-SCHF 2 4-CF 3 0 HHHO 3-Cl 4-SCF 3 4-OCF 3 0 HHHO 3-Cl 4-SCH 3 4-Cl 0 HHHO 3-Cl 4-SOCH 3 4-CF 30 HHHO 3-Cl 4-SO 2 CH 3 4-OCF 3 0 HHHO 3-Cl 4-OSO 2 CH 3 4-Cl 0 HHHO 3-Cl 4-NHCOCH 3 4-CF 3 0 HHHO 3 -Cl 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3-Cl 2,4-Cl 2 4-Cl 0 HHHO 3-Cl 3-OCF 2 O-4 4-CF 3 ───────── ───────────────────────── ─

【００７０】[0070]

【表３６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Br H 4-Cl 0 H H H O 3-Br 4-Cl 4-CF3 0 H H H O 3-Br 4-Br 4-OCF3 0 H H H O 3-Br 4-CN 4-Cl 0 H H H O 3-Br 4-NO2 4-CF3 0 H H H O 3-Br 4-CH3 4-OCF3 0 H H H O 3-Br 4-CF3 4-Cl 0 H H H O 3-Br 4-OCH2CH3 4-CF3 0 H H H O 3-Br 4-OCHF2 4-OCF3 0 H H H O 3-Br 4-OCH2CF3 4-Cl 0 H H H O 3-Br 4-OCF2Br 4-CF3 0 H H H O 3-Br 4-OCF2CHF2 4-OCF3 0 H H H O 3-Br 4-OSO2CF3 4-Cl 0 H H H O 3-Br 4-SCHF2 4-CF3 0 H H H O 3-Br 4-SCF3 4-OCF3 0 H H H O 3-Br 4-SCH3 4-Cl 0 H H H O 3-Br 4-SOCH3 4-CF3 0 H H H O 3-Br 4-SO2CH3 4-OCF3 0 H H H O 3-Br 4-OSO2CH3 4-Cl 0 H H H O 3-Br 4-NHCOCH3 4-CF3 0 H H H O 3-Br 4-NHSO2CH3 4-OCF3 0 H H H O 3-Br 2,4-Cl2 4-Cl 0 H H H O 3-Br 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 36] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Br H 4-Cl 0 HHHO 3- Br 4-Cl 4-CF 3 0 HHHO 3-Br 4-Br 4-OCF 3 0 HHHO 3-Br 4-CN 4-Cl 0 HHHO 3-Br 4-NO 2 4-CF 3 0 HHHO 3-Br 4 -CH 3 4-OCF 3 0 HHHO 3-Br 4-CF 3 4-Cl 0 HHHO 3-Br 4-OCH 2 CH 3 4-CF 3 0 HHHO 3-Br 4-OCHF 2 4-OCF 3 0 HHHO 3 -Br 4-OCH 2 CF 3 4-Cl 0 HHHO 3-Br 4-OCF 2 Br 4-CF 3 0 HHHO 3-Br 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-Br 4-OSO 2 CF 3 4-Cl 0 HHHO 3-Br 4-SCHF 2 4-CF 3 0 HHHO 3-Br 4-SCF 3 4-OCF 3 0 HHHO 3-Br 4-SCH 3 4-Cl 0 HHHO 3-Br 4-SOCH 3 4-CF 3 0 HHHO 3-Br 4-SO 2 CH 3 4-OCF 3 0 HHHO 3-Br 4-OSO 2 CH 3 4-Cl 0 HHHO 3-Br 4-NHCOCH 3 4-CF 3 0 HHHO 3 -Br 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3-Br 2,4-Cl 2 4-Cl 0 HHHO 3-Br 3-OCF 2 O-4 4-CF 3 ───────── ───────────────────────── ─

【００７１】[0071]

【表３７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3,4-F2 H 4-Cl 0 H H H O 3,4-F2 4-Cl 4-CF3 0 H H H O 3,4-F2 4-Br 4-OCF3 0 H H H O 3,4-F2 4-CN 4-Cl 0 H H H O 3,4-F2 4-NO2 4-CF3 0 H H H O 3,4-F2 4-CH3 4-OCF3 0 H H H O 3,4-F2 4-CF3 4-Cl 0 H H H O 3,4-F2 4-OCH2CH3 4-CF3 0 H H H O 3,4-F2 4-OCHF2 4-OCF3 0 H H H O 3,4-F2 4-OCH2CF3 4-Cl 0 H H H O 3,4-F2 4-OCF2Br 4-CF3 0 H H H O 3,4-F2 4-OCF2CHF2 4-OCF3 0 H H H O 3,4-F2 4-OSO2CF3 4-Cl 0 H H H O 3,4-F2 4-SCHF2 4-CF3 0 H H H O 3,4-F2 4-SCF3 4-OCF3 0 H H H O 3,4-F2 4-SCH3 4-Cl 0 H H H O 3,4-F2 4-SOCH3 4-CF3 0 H H H O 3,4-F2 4-SO2CH3 4-OCF3 0 H H H O 3,4-F2 4-OSO2CH3 4-Cl 0 H H H O 3,4-F2 4-NHCOCH3 4-CF3 0 H H H O 3,4-F2 4-NHSO2CH3 4-OCF3 0 H H H O 3,4-F2 2,4-Cl2 4-Cl 0 H H H O 3,4-F2 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 37] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3,4-F 2 H 4-Cl 0 HHHO 3,4-F 2 4-Cl 4-CF 3 0 HHHO 3,4-F 2 4-Br 4-OCF 3 0 HHHO 3,4-F 2 4-CN 4-Cl 0 HHHO 3,4-F 2 4-NO 2 4-CF 30 HHHO 3,4-F 2 4-CH 3 4-OCF 30 HHHO 3,4-F 2 4-CF 3 4-Cl 0 HHHO 3,4-F 2 4- OCH 2 CH 3 4-CF 3 0 HHHO 3,4-F 2 4-OCHF 2 4-OCF 3 0 HHHO 3,4-F 2 4-OCH 2 CF 3 4-Cl 0 HHHO 3,4-F 2 4 -OCF 2 Br 4-CF 30 HHHO 3,4-F 2 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3,4-F 2 4-OSO 2 CF 3 4-Cl 0 HHHO 3,4-F 2 4-SCHF 2 4-CF 3 0 HHHO 3,4-F 2 4-SCF 3 4-OCF 3 0 HHHO 3,4-F 2 4-SCH 3 4-Cl 0 HHHO 3,4-F 2 4- SOCH 3 4-CF 3 0 HHHO 3,4-F 2 4-SO 2 CH 3 4-OCF 3 0 HHHO 3,4-F 2 4-OSO 2 CH 3 4-Cl 0 HHHO 3,4-F 2 4 -NHCOCH 3 4-CF 3 0 HHHO 3,4-F 2 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 3,4-F 2 2,4-Cl 2 4-Cl 0 HHHO 3,4-F 2 3-OCF 2 O-4 4 -CF 3 ────────── ────────────────────────

【００７２】[0072]

【表３８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-Cl 4-F 4-Cl 0 H H H O 4-Cl 4-Cl 4-CF3 0 H H H O 4-Cl 4-Br 4-OCF3 0 H H H O 4-Cl 4-CN 4-Cl 0 H H H O 4-Cl 4-NO2 4-CF3 0 H H H O 4-Cl 4-CH3 4-OCF3 0 H H H O 4-Cl 4-CF3 4-Cl 0 H H H O 4-Cl 4-OCH2CH3 4-CF3 0 H H H O 4-Cl 4-OCHF2 4-OCF3 0 H H H O 4-Cl 4-OCH2CF3 4-Cl 0 H H H O 4-Cl 4-OCF2Br 4-CF3 0 H H H O 4-Cl 4-OCF2CHF2 4-OCF3 0 H H H O 4-Cl 4-OSO2CF3 4-Cl 0 H H H O 4-Cl 4-SCHF2 4-CF3 0 H H H O 4-Cl 4-SCF3 4-OCF3 0 H H H O 4-Cl 4-SCH3 4-Cl 0 H H H O 4-Cl 4-SOCH3 4-CF3 0 H H H O 4-Cl 4-SO2CH3 4-OCF3 0 H H H O 4-Cl 4-OSO2CH3 4-Cl 0 H H H O 4-Cl 4-NHCOCH3 4-CF3 0 H H H O 4-Cl 4-NHSO2CH3 4-OCF3 0 H H H O 4-Cl 2,4-Cl2 4-Cl 0 H H H O 4-Cl 3-OCF2O-4 4-CF3 ───────────────────────────────────[Table 38] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-Cl 4-F 4-Cl 0 HHHO 4-Cl 4-Cl 4-CF 30 HHHO 4-Cl 4-Br 4-OCF 3 0 HHHO 4-Cl 4-CN 4-Cl 0 HHHO 4-Cl 4-NO 2 4-CF 30 HHHO 4- Cl 4-CH 3 4-OCF 3 0 HHHO 4-Cl 4-CF 3 4-Cl 0 HHHO 4-Cl 4-OCH 2 CH 3 4-CF 3 0 HHHO 4-Cl 4-OCHF 2 4-OCF 3 0 HHHO 4-Cl 4-OCH 2 CF 3 4-Cl 0 HHHO 4-Cl 4-OCF 2 Br 4-CF 3 0 HHHO 4-Cl 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 4-Cl 4-OSO 2 CF 3 4-Cl 0 HHHO 4-Cl 4-SCHF 2 4-CF 3 0 HHHO 4-Cl 4-SCF 3 4-OCF 3 0 HHHO 4-Cl 4-SCH 3 4-Cl 0 HHHO 4-Cl 4 -SOCH 3 4-CF 3 0 HHHO 4-Cl 4-SO 2 CH 3 4-OCF 3 0 HHHO 4-Cl 4-OSO 2 CH 3 4-Cl 0 HHHO 4-Cl 4-NHCOCH 3 4-CF 3 0 HHHO 4-Cl 4-NHSO 2 CH 3 4-OCF 3 0 HHHO 4-Cl 2,4-Cl 2 4-Cl 0 HHHO 4-Cl 3-OCF 2 O-4 4-CF 3 ─────── ──────────────────────────── ──

【００７３】[0073]

【表３９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 2-F 4-F 4-Cl 0 H H H O 2-Cl 4-F 4-CF3 0 H H H O 4-Cl 4-F 4-OCF3 0 H H H O 4-Br 4-F 4-Cl 0 H H H O 3-I 4-F 4-CF3 0 H H H O 4-I 4-F 4-OCF3 0 H H H O 3-CH3 4-F 4-Cl 0 H H H O 4-CH3 4-F 4-CF3 0 H H H O 4-CH2CH3 4-F 4-OCF3 0 H H H O 3-CH(CH3)2 4-F 4-Cl 0 H H H O 4-CH2CH2CH2CH3 4-F 4-CF3 0 H H H O 4-C(CH3)3 4-F 4-OCF3 0 H H H O 3-CH2CH=CH2 4-F 4-Cl 0 H H H O 4-Q1 4-F 4-CF3 0 H H H O 4-Q2 4-F 4-OCF3 0 H H H O 4-Q3 4-F 4-Cl 0 H H H O 4-Q4 4-F 4-CF3 0 H H H O 3-CHF2 4-F 4-OCF3 0 H H H O 4-CHF2 4-F 4-Cl 0 H H H O 3-CH2Br 4-F 4-CF3 0 H H H O 3-CH2Cl 4-F 4-OCF3 0 H H H O 2-CF3 4-F 4-Cl 0 H H H O 4-CF3 4-F 4-CF3 ───────────────────────────────────[Table 39] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 2-F 4-F 4-Cl 0 HHHO 2-Cl 4-F 4-CF 3 0 HHHO 4-Cl 4-F 4-OCF 3 0 HHHO 4-Br 4-F 4-Cl 0 HHHO 3-I 4-F 4-CF 3 0 HHHO 4-I 4-F 4-OCF 3 0 HHHO 3-CH 3 4-F 4-Cl 0 HHHO 4-CH 3 4-F 4-CF 3 0 HHHO 4-CH 2 CH 3 4-F 4-OCF 3 0 HHHO 3 -CH (CH 3 ) 2 4-F 4-Cl 0 HHHO 4-CH 2 CH 2 CH 2 CH 3 4-F 4-CF 3 0 HHHO 4-C (CH 3 ) 3 4-F 4-OCF 3 0 HHHO 3-CH 2 CH = CH 2 4-F 4-Cl 0 HHHO 4-Q1 4-F 4-CF 3 0 HHHO 4-Q2 4-F 4-OCF 3 0 HHHO 4-Q3 4-F 4-Cl 0 HHHO 4-Q4 4-F 4-CF 3 0 HHHO 3-CHF 2 4-F 4-OCF 3 0 HHHO 4-CHF 2 4-F 4-Cl 0 HHHO 3-CH 2 Br 4-F 4-CF 3 0 HHHO 3-CH 2 Cl 4-F 4-OCF 30 HHHO 2-CF 3 4-F 4-Cl 0 HHHO 4-CF 3 4-F 4-CF 3 ─────────── ─────────────────────────

【００７４】[0074]

【表４０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-CH2CN 4-F 4-Cl 0 H H H O 4-CH2OH 4-F 4-CF3 0 H H H O 4-CH2CO2H 4-F 4-OCF3 0 H H H O 3-OCH3 4-F 4-Cl 0 H H H O 4-OCH3 4-F 4-CF3 0 H H H O 3-OCH2CH3 4-F 4-OCF3 0 H H H O 4-OCH(CH3)2 4-F 4-Cl 0 H H H O 4-OC(CH3)3 4-F 4-CF3 0 H H H O 2-OCHF2 4-F 4-OCF3 0 H H H O 3-OCF2Br 4-F 4-Cl 0 H H H O 4-OCF2Br 4-F 4-CF3 0 H H H O 4-OCF3 4-F 4-OCF3 0 H H H O 3-OCH2CF3 4-F 4-Cl 0 H H H O 4-OCH2CF3 4-F 4-CF3 0 H H H O 3-OCF2CF3 4-F 4-OCF3 0 H H H O 4-OCF2CF3 4-F 4-Cl 0 H H H O 2-OCF2CHF2 4-F 4-CF3 0 H H H O 4-OCF2CHF2 4-F 4-OCF3 0 H H H O 3-OCF2CHFCl 4-F 4-Cl 0 H H H O 4-OCF2CHFBr 4-F 4-CF3 0 H H H O 3-OCF2CF2CF3 4-F 4-OCF3 0 H H H O 3-OCH2CH=CHCl 4-F 4-Cl 0 H H H O 3-O(Q1-2,2-Cl2) 4-F 4-CF3 ───────────────────────────────────[Table 40] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-CH 2 CN 4-F 4-Cl 0 HHHO 4-CH 2 OH 4-F 4-CF 3 0 HHHO 4-CH 2 CO 2 H 4-F 4-OCF 3 0 HHHO 3-OCH 3 4-F 4-Cl 0 HHHO 4-OCH 3 4- F 4-CF 3 0 HHHO 3-OCH 2 CH 3 4-F 4-OCF 3 0 HHHO 4-OCH (CH 3 ) 2 4-F 4-Cl 0 HHHO 4-OC (CH 3 ) 3 4-F 4 -CF 3 0 HHHO 2-OCHF 2 4-F 4-OCF 3 0 HHHO 3-OCF 2 Br 4-F 4-Cl 0 HHHO 4-OCF 2 Br 4-F 4-CF 3 0 HHHO 4-OCF 3 4 -F 4-OCF 3 0 HHHO 3-OCH 2 CF 3 4-F 4-Cl 0 HHHO 4-OCH 2 CF 3 4-F 4-CF 3 0 HHHO 3-OCF 2 CF 3 4-F 4-OCF 3 0 HHHO 4-OCF 2 CF 3 4-F 4-Cl 0 HHHO 2-OCF 2 CHF 2 4-F 4-CF 3 0 HHHO 4-OCF 2 CHF 2 4-F 4-OCF 3 0 HHHO 3-OCF 2 CHFCl 4-F 4-Cl 0 HHHO 4-OCF 2 CHFBr 4-F 4-CF 3 0 HHHO 3-OCF 2 CF 2 CF 3 4-F 4-OCF 3 0 HHHO 3-OCH 2 CH = CHCl 4-F 4-Cl 0 HHHO 3-O (Q1-2,2-Cl 2) 4-F 4-CF 3 ──────────────── ──────────────────

【００７５】[0075]

【表４１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-SCH3 4-F 4-Cl 0 H H H O 4-SCH3 4-F 4-CF3 0 H H H O 3-SCHF2 4-F 4-OCF3 0 H H H O 4-SCHF2 4-F 4-Cl 0 H H H O 3-SCF3 4-F 4-CF3 0 H H H O 4-SCF3 4-F 4-OCF3 0 H H H O 3-SOCH3 4-F 4-Cl 0 H H H O 4-SOCH3 4-F 4-CF3 0 H H H O 3-SO2CH3 4-F 4-OCF3 0 H H H O 4-SO2CH3 4-F 4-Cl 0 H H H O 3-SO2CHF2 4-F 4-CF3 0 H H H O 4-CH2OCH3 4-F 4-OCF3 0 H H H O 3-OCF2CHFOCF3 4-F 4-Cl 0 H H H O 4-OCF2CHFOCF3 4-F 4-CF3 0 H H H O 4-CH2COCH3 4-F 4-OCF3 0 H H H O 4-CH2CO2CH3 4-F 4-Cl 0 H H H O 4-OCO2CH3 4-F 4-CF3 0 H H H O 3-OCOCH3 4-F 4-OCF3 0 H H H O 4-COCH3 4-F 4-Cl 0 H H H O 4-COCF3 4-F 4-CF3 0 H H H O 4-CO2CH2CH3 4-F 4-OCF3 0 H H H O 4-CO2C(CH3)3 4-F 4-Cl 0 H H H O 3-CO2CH2CF3 4-F 4-CF3 ───────────────────────────────────[Table 41] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-SCH 3 4-F 4-Cl 0 HHHO 4-SCH 3 4-F 4-CF 3 0 HHHO 3-SCHF 2 4-F 4-OCF 3 0 HHHO 4-SCHF 2 4-F 4-Cl 0 HHHO 3-SCF 3 4-F 4-CF 3 0 HHHO 4-SCF 3 4-F 4-OCF 3 0 HHHO 3-SOCH 3 4-F 4-Cl 0 HHHO 4-SOCH 3 4-F 4-CF 3 0 HHHO 3-SO 2 CH 3 4-F 4 -OCF 3 0 HHHO 4-SO 2 CH 3 4-F 4-Cl 0 HHHO 3-SO 2 CHF 2 4-F 4-CF 3 0 HHHO 4-CH 2 OCH 3 4-F 4-OCF 3 0 HHHO 3 -OCF 2 CHFOCF 3 4-F 4-Cl 0 HHHO 4-OCF 2 CHFOCF 3 4-F 4-CF 3 0 HHHO 4-CH 2 COCH 3 4-F 4-OCF 3 0 HHHO 4-CH 2 CO 2 CH 3 4-F 4-Cl 0 HHHO 4-OCO 2 CH 3 4-F 4-CF 3 0 HHHO 3-OCOCH 3 4-F 4-OCF 3 0 HHHO 4-COCH 3 4-F 4-Cl 0 HHHO 4 -COCF 3 4-F 4-CF 3 0 HHHO 4-CO 2 CH 2 CH 3 4-F 4-OCF 3 0 HHHO 4-CO 2 C (CH 3 ) 3 4-F 4-Cl 0 HHHO 3-CO 2 CH 2 CF 3 4-F 4-CF 3 ───────────────────── ─────────────

【００７６】[0076]

【表４２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-NO2 4-F 4-Cl 0 H H H O 4-NO2 4-F 4-CF3 0 H H H O 3-CN 4-F 4-OCF3 0 H H H O 4-CN 4-F 4-Cl 0 H H H O 3-OH 4-F 4-CF3 0 H H H O 4-OH 4-F 4-OCF3 0 H H H O 4-SCN 4-F 4-Cl 0 H H H O 3-OSO2CH3 4-F 4-CF3 0 H H H O 4-OSO2CH3 4-F 4-OCF3 0 H H H O 3-OSO2CF3 4-F 4-Cl 0 H H H O 4-OSO2CF3 4-F 4-CF3 0 H H H O 4-CSCH3 4-F 4-OCF3 0 H H H O 4-NH2 4-F 4-Cl 0 H H H O 4-N(CH3)2 4-F 4-CF3 0 H H H O 4-CON(CH3)2 4-F 4-OCF3 0 H H H O 3-OCON(CH3)2 4-F 4-Cl 0 H H H O 4-NHCOCH3 4-F 4-CF3 0 H H H O 4-SO2N(CH3)2 4-F 4-OCF3 0 H H H O 4-Si(CH3)3 4-F 4-Cl 0 H H H O 4-C6H5 4-F 4-CF3 0 H H H O 3-OC6H5 4-F 4-OCF3 0 H H H O 4-OC6H5 4-F 4-Cl 0 H H H O 3-SC6H5 4-F 4-CF3 ───────────────────────────────────[Table 42] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-NO 2 4-F 4-Cl 0 HHHO 4-NO 2 4-F 4-CF 3 0 HHHO 3-CN 4-F 4-OCF 3 0 HHHO 4-CN 4-F 4-Cl 0 HHHO 3-OH 4-F 4-CF 3 0 HHHO 4 -OH 4-F 4-OCF 3 0 HHHO 4-SCN 4-F 4-Cl 0 HHHO 3-OSO 2 CH 3 4-F 4-CF 3 0 HHHO 4-OSO 2 CH 3 4-F 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-F 4-Cl 0 HHHO 4-OSO 2 CF 3 4-F 4-CF 3 0 HHHO 4-CSCH 3 4-F 4-OCF 3 0 HHHO 4-NH 2 4- F 4-Cl 0 HHHO 4-N (CH 3 ) 2 4-F 4-CF 3 0 HHHO 4-CON (CH 3 ) 2 4-F 4-OCF 3 0 HHHO 3-OCON (CH 3 ) 2 4- F 4-Cl 0 HHHO 4-NHCOCH 3 4-F 4-CF 3 0 HHHO 4-SO 2 N (CH 3 ) 2 4-F 4-OCF 3 0 HHHO 4-Si (CH 3 ) 3 4-F 4 -Cl 0 HHHO 4-C 6 H 5 4-F 4-CF 3 0 HHHO 3-OC 6 H 5 4-F 4-OCF 3 0 HHHO 4-OC 6 H 5 4-F 4-Cl 0 HHHO 3- SC 6 H 5 4-F 4-CF 3 ─────────────────────────────────── ─

【００７７】[0077]

【表４３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-SO2C6H5 4-F 4-Cl 0 H H H O 3-NHC6H5 4-F 4-CF3 0 H H H O 3-CH2C6H5 4-F 4-OCF3 0 H H H O 3-COC6H5 4-F 4-Cl 0 H H H O 3-NHSO2CH3 4-F 4-CF3 0 H H H O 2-CH=CH-CH=CH-3 4-F 4-OCF3 0 H H H O 3-CH=CH-CH=CH-4 4-F 4-Cl 0 H H H O 3-OCH2O-4 4-F 4-CF3 0 H H H O 3-OCF2O-4 4-F 4-OCF3 0 H H H O 3-OCH2CH2O-4 4-F 4-Cl 0 H H H O 3-OCF2CF2O-4 4-F 4-CF3 0 H H H O 2,3-F2 4-F 4-OCF3 0 H H H O 2,4-F2 4-F 4-Cl 0 H H H O 2,5-F2 4-F 4-CF3 0 H H H O 3,5-F2 4-F 4-OCF3 0 H H H O 3,4-Cl2 4-F 4-Cl 0 H H H O 3,5-Cl2 4-F 4-CF3 0 H H H O 3,4-Br2 4-F 4-OCF3 0 H H H O 3,5-I2 4-F 4-Cl 0 H H H O 2,4-(CH3)2 4-F 4-CF3 0 H H H O 3,4-(OCH3)2 4-F 4-OCF3 0 H H H O 3,4-(OCF3)2 4-F 4-Cl 0 H H H O 3,5-(OCHF2)2 4-F 4-CF3 ───────────────────────────────────[Table 43] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-SO 2 C 6 H 5 4-F 4-Cl 0 HHHO 3-NHC 6 H 5 4-F 4-CF 3 0 HHHO 3-CH 2 C 6 H 5 4-F 4-OCF 30 HHHO 3-COC 6 H 5 4-F 4-Cl 0 HHHO 3-NHSO 2 CH 3 4-F 4-CF 3 0 HHHO 2-CH = CH-CH = CH-3 4-F 4-OCF 3 0 HHHO 3-CH = CH-CH = CH-4 4-F 4-Cl 0 HHHO 3-OCH 2 O-4 4-F 4-CF 3 0 HHHO 3-OCF 2 O-4 4-F 4-OCF 3 0 HHHO 3-OCH 2 CH 2 O-4 4-F 4 -Cl 0 HHHO 3-OCF 2 CF 2 O-4 4-F 4-CF 3 0 HHHO 2,3-F 2 4-F 4-OCF 3 0 HHHO 2,4-F 2 4-F 4-Cl 0 HHHO 2,5-F 2 4-F 4-CF 3 0 HHHO 3,5-F 2 4-F 4-OCF 3 0 HHHO 3,4-Cl 2 4-F 4-Cl 0 HHHO 3,5-Cl 2 4-F 4-CF 30 HHHO 3,4-Br 2 4-F 4-OCF 30 HHHO 3,5-I 2 4-F 4-Cl 0 HHHO 2,4- (CH 3 ) 2 4- F 4-CF 3 0 HHHO 3,4- (OCH 3 ) 2 4-F 4-OCF 3 0 HHHO 3,4- (OCF 3 ) 2 4-F 4-Cl 0 HHHO 3,5- (OCHF 2 ) 2 4-F 4-CF 3 ────────────────── ────────────────

【００７８】[0078]

【表４４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3,4-(CF3)2 4-F 4-Cl 0 H H H O 3,5-(CF3)2 4-F 4-CF3 0 H H H O 2-F-4-Cl 4-F 4-OCF3 0 H H H O 3-F-5-Cl 4-F 4-Cl 0 H H H O 3-F-5-CF3 4-F 4-CF3 0 H H H O 3-F-5-OCHF2 4-F 4-OCF3 0 H H H O 3-Cl-5-CF3 4-F 4-Cl 0 H H H O 3-Cl-4-OCHF2 4-F 4-CF3 0 H H H O 3-Cl-4-CN 4-F 4-OCF3 0 H H H O 3-Cl-4-F 4-F 4-Cl 0 H H H O 3-Cl-5-OSO2CF3 4-F 4-CF3 0 H H H O 3-F-4-OSO2CF3 4-F 4-OCF3 0 H H H O 2,3,4-F3 4-F 4-Cl 0 H H H O 3,4,5-F3 4-F 4-CF3 0 H H H O 2,4,5-Cl3 4-F 4-OCF3 0 H H H O 2,4,6-Cl3 4-F 4-Cl 0 H H H O 2-F-4,5-Cl2 4-F 4-CF3 0 H H H O 3,5-Cl2-4-CF3 4-F 4-OCF3 0 H H H O 2,3,4,5-F4 4-F 4-Cl 0 H H H O 2,3,5,6-F4 4-F 4-CF3 0 H H H O 2,4-F2-3,5-Cl2 4-F 4-OCF3 0 H H H O 2,3,4,5,6-F5 4-F 4-Cl 0 H H H O 2,3,5,6-F4-4-CN 4-F 4-CF3 ───────────────────────────────────[Table 44] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3,4- (CF 3 ) 2 4- F 4-Cl 0 HHHO 3,5- (CF 3 ) 2 4-F 4-CF 3 0 HHHO 2-F-4-Cl 4-F 4-OCF 3 0 HHHO 3-F-5-Cl 4-F 4-Cl 0 HHHO 3-F-5-CF 3 4-F 4-CF 3 0 HHHO 3-F-5-OCHF 2 4-F 4-OCF 30 HHHO 3-Cl-5-CF 3 4-F 4-Cl 0 HHHO 3-Cl-4-OCHF 2 4-F 4-CF 3 0 HHHO 3-Cl-4-CN 4-F 4-OCF 3 0 HHHO 3-Cl-4-F 4-F 4- Cl 0 HHHO 3-Cl-5-OSO 2 CF 3 4-F 4-CF 3 0 HHHO 3-F-4-OSO 2 CF 3 4-F 4-OCF 3 0 HHHO 2,3,4-F 3 4 -F 4-Cl 0 HHHO 3,4,5-F 3 4-F 4-CF 3 0 HHHO 2,4,5-Cl 3 4-F 4-OCF 3 0 HHHO 2,4,6-Cl 3 4 -F 4-Cl 0 HHHO 2-F-4,5-Cl 2 4-F 4-CF 3 0 HHHO 3,5-Cl 2 -4-CF 3 4-F 4-OCF 3 0 HHHO 2,3, 4,5-F 4 4-F 4-Cl 0 HHHO 2,3,5,6-F 4 4-F 4-CF 3 0 HHHO 2,4-F 2 -3,5-Cl 2 4-F 4 -OCF 3 0 HHHO 2,3,4,5,6-F 5 4-F 4-Cl 0 HHHO 2,3,5,6-F 4 -4-CN 4-F 4-CF 3 ──── ────────── ────────────────────

【００７９】[0079]

【表４５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-F 4-Cl 4-Cl 0 H H H O 3-Cl 4-Cl 4-CF3 0 H H H O 4-Cl 4-Cl 4-OCF3 0 H H H O 3-Br 4-Cl 4-Cl 0 H H H O 3-CH3 4-Cl 4-CF3 0 H H H O 4-CF3 4-Cl 4-OCF3 0 H H H O 3-OCH3 4-Cl 4-Cl 0 H H H O 3-OCHF2 4-Cl 4-CF3 0 H H H O 4-OCHF2 4-Cl 4-OCF3 0 H H H O 3-OCF2Br 4-Cl 4-Cl 0 H H H O 3-OCF3 4-Cl 4-CF3 0 H H H O 3-OCH2CF3 4-Cl 4-OCF3 0 H H H O 3-OCF2CHF2 4-Cl 4-Cl 0 H H H O 3-SCHF2 4-Cl 4-CF3 0 H H H O 3-SCF3 4-Cl 4-OCF3 0 H H H O 3-NO2 4-Cl 4-Cl 0 H H H O 3-CN 4-Cl 4-CF3 0 H H H O 3-OSO2CH3 4-Cl 4-OCF3 0 H H H O 3-OSO2CF3 4-Cl 4-Cl 0 H H H O 4-OSO2CF3 4-Cl 4-CF3 0 H H H O 3,4-F2 4-Cl 4-OCF3 0 H H H O 3,5-F2 4-Cl 4-Cl 0 H H H O 3-Cl-4-F 4-Cl 4-CF3 ───────────────────────────────────[Table 45] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-F 4-Cl 4-Cl 0 HHHO 3-Cl 4-Cl 4-CF 30 HHHO 4-Cl 4-Cl 4-OCF 3 0 HHHO 3-Br 4-Cl 4-Cl 0 HHHO 3-CH 3 4-Cl 4-CF 30 HHHO 4- CF 3 4-Cl 4-OCF 3 0 HHHO 3-OCH 3 4-Cl 4-Cl 0 HHHO 3-OCHF 2 4-Cl 4-CF 3 0 HHHO 4-OCHF 2 4-Cl 4-OCF 3 0 HHHO 3 -OCF 2 Br 4-Cl 4-Cl 0 HHHO 3-OCF 3 4-Cl 4-CF 3 0 HHHO 3-OCH 2 CF 3 4-Cl 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4-Cl 4 -Cl 0 HHHO 3-SCHF 2 4-Cl 4-CF 3 0 HHHO 3-SCF 3 4-Cl 4-OCF 3 0 HHHO 3-NO 2 4-Cl 4-Cl 0 HHHO 3-CN 4-Cl 4- CF 3 0 HHHO 3-OSO 2 CH 3 4-Cl 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-Cl 4-Cl 0 HHHO 4-OSO 2 CF 3 4-Cl 4-CF 3 0 HHHO 3, 4-F 2 4-Cl 4-OCF 3 0 HHHO 3,5-F 2 4-Cl 4-Cl 0 HHHO 3-Cl-4-F 4-Cl 4-CF 3 ───────── ──────────────────────────

【００８０】[0080]

【表４６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-F 4-Br 4-Cl 0 H H H O 3-Cl 4-Br 4-CF3 0 H H H O 4-Cl 4-Br 4-OCF3 0 H H H O 3-Br 4-Br 4-Cl 0 H H H O 3-CH3 4-Br 4-CF3 0 H H H O 4-CF3 4-Br 4-OCF3 0 H H H O 3-OCH3 4-Br 4-Cl 0 H H H O 3-OCHF2 4-Br 4-CF3 0 H H H O 4-OCHF2 4-Br 4-OCF3 0 H H H O 3-OCF2Br 4-Br 4-Cl 0 H H H O 3-OCF3 4-Br 4-CF3 0 H H H O 3-OCH2CF3 4-Br 4-OCF3 0 H H H O 3-OCF2CHF2 4-Br 4-Cl 0 H H H O 3-SCHF2 4-Br 4-CF3 0 H H H O 3-SCF3 4-Br 4-OCF3 0 H H H O 3-NO2 4-Br 4-Cl 0 H H H O 3-CN 4-Br 4-CF3 0 H H H O 3-OSO2CH3 4-Br 4-OCF3 0 H H H O 3-OSO2CF3 4-Br 4-Cl 0 H H H O 4-OSO2CF3 4-Br 4-CF3 0 H H H O 3,4-F2 4-Br 4-OCF3 0 H H H O 3,5-F2 4-Br 4-Cl 0 H H H O 3-Cl-4-F 4-Br 4-CF3 ───────────────────────────────────[Table 46] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-F 4-Br 4-Cl 0 HHHO 3-Cl 4-Br 4-CF 30 HHHO 4-Cl 4-Br 4-OCF 3 0 HHHO 3-Br 4-Br 4-Cl 0 HHHO 3-CH 3 4-Br 4-CF 30 HHHO 4- CF 3 4-Br 4-OCF 3 0 HHHO 3-OCH 3 4-Br 4-Cl 0 HHHO 3-OCHF 2 4-Br 4-CF 3 0 HHHO 4-OCHF 2 4-Br 4-OCF 3 0 HHHO 3 -OCF 2 Br 4-Br 4-Cl 0 HHHO 3-OCF 3 4-Br 4-CF 3 0 HHHO 3-OCH 2 CF 3 4-Br 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4-Br 4 -Cl 0 HHHO 3-SCHF 2 4-Br 4-CF 3 0 HHHO 3-SCF 3 4-Br 4-OCF 3 0 HHHO 3-NO 2 4-Br 4-Cl 0 HHHO 3-CN 4-Br 4- CF 3 0 HHHO 3-OSO 2 CH 3 4-Br 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-Br 4-Cl 0 HHHO 4-OSO 2 CF 3 4-Br 4-CF 3 0 HHHO 3, 4-F 2 4-Br 4-OCF 3 0 HHHO 3,5-F 2 4-Br 4-Cl 0 HHHO 3-Cl-4-F 4-Br 4-CF 3 ───────── ──────────────────────────

【００８１】[0081]

【表４７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 4-F 4-CN 4-Cl 0 H H H O 2-Cl 4-CN 4-CF3 0 H H H O 4-Cl 4-CN 4-OCF3 0 H H H O 3-Br 4-CN 4-Cl 0 H H H O 3-CH3 4-CN 4-CF3 0 H H H O 4-CF3 4-CN 4-OCF3 0 H H H O 3-OCH3 4-CN 4-Cl 0 H H H O 3-OCHF2 4-CN 4-CF3 0 H H H O 4-OCHF2 4-CN 4-OCF3 0 H H H O 3-OCF2Br 4-CN 4-Cl 0 H H H O 3-OCF3 4-CN 4-CF3 0 H H H O 3-OCF3 4-CN 4-OCF3 0 H H H O 3-OCH2CF3 4-CN 4-OCF3 0 H H H O 3-OCF2CHF2 4-CN 4-Cl 0 H H H O 3-SCHF2 4-CN 4-CF3 0 H H H O 3-SCF3 4-CN 4-OCF3 0 H H H O 3-NO2 4-CN 4-Cl 0 H H H O 3-CN 4-CN 4-CF3 0 H H H O 3-OSO2CH3 4-CN 4-OCF3 0 H H H O 3-OSO2CF3 4-CN 4-Cl 0 H H H O 4-OSO2CF3 4-CN 4-CF3 0 H H H O 3,4-F2 4-CN 4-OCF3 0 H H H O 3,5-F2 4-CN 4-Cl ───────────────────────────────────[Table 47] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 4-F 4-CN 4-Cl 0 HHHO 2-Cl 4-CN 4-CF 30 HHHO 4-Cl 4-CN 4-OCF 3 0 HHHO 3-Br 4-CN 4-Cl 0 HHHO 3-CH 3 4-CN 4-CF 30 HHHO 4- CF 3 4-CN 4-OCF 3 0 HHHO 3-OCH 3 4-CN 4-Cl 0 HHHO 3-OCHF 2 4-CN 4-CF 3 0 HHHO 4-OCHF 2 4-CN 4-OCF 3 0 HHHO 3 -OCF 2 Br 4-CN 4-Cl 0 HHHO 3-OCF 3 4-CN 4-CF 3 0 HHHO 3-OCF 3 4-CN 4-OCF 3 0 HHHO 3-OCH 2 CF 3 4-CN 4-OCF 30 HHHO 3-OCF 2 CHF 2 4-CN 4-Cl 0 HHHO 3-SCHF 2 4-CN 4-CF 30 HHHO 3-SCF 3 4-CN 4-OCF 30 HHHO 3-NO 2 4-CN 4-Cl 0 HHHO 3-CN 4-CN 4-CF 3 0 HHHO 3-OSO 2 CH 3 4-CN 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-CN 4-Cl 0 HHHO 4-OSO 2 CF 3 4-CN 4-CF 30 HHHO 3,4-F 2 4-CN 4-OCF 30 HHHO 3,5-F 2 4-CN 4-Cl ──────────── ───────────────────────

【００８２】[0082]

【表４８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 4-CN 4-CF3 0 H H H O 4-F 4-OHCF2 4-Cl 0 H H H O 3-Cl 4-OHCF2 4-CF3 0 H H H O 4-Cl 4-OHCF2 4-OCF3 0 H H H O 3-Br 4-OHCF2 4-Cl 0 H H H O 3-CH3 4-OHCF2 4-CF3 0 H H H O 4-CF3 4-OHCF2 4-OCF3 0 H H H O 3-OCH3 4-OHCF2 4-Cl 0 H H H O 3-OCHF2 4-OHCF2 4-CF3 0 H H H O 4-OCHF2 4-OHCF2 4-OCF3 0 H H H O 3-OCF2Br 4-OHCF2 4-Cl 0 H H H O 3-OCF3 4-OHCF2 4-CF3 0 H H H O 3-OCH2CF3 4-OHCF2 4-OCF3 0 H H H O 3-OCF2CHF2 4-OHCF2 4-Cl 0 H H H O 3-SCHF2 4-OHCF2 4-CF3 0 H H H O 3-SCF3 4-OHCF2 4-OCF3 0 H H H O 3-NO2 4-OHCF2 4-Cl 0 H H H O 3-CN 4-OHCF2 4-CF3 0 H H H O 3-OSO2CH3 4-OHCF2 4-OCF3 0 H H H O 3-OSO2CF3 4-OHCF2 4-Cl 0 H H H O 4-OSO2CF3 4-OHCF2 4-CF3 0 H H H O 3,4-F2 4-OHCF2 4-OCF3 0 H H H O 3,5-F2 4-OHCF2 4-Cl ───────────────────────────────────[Table 48] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-CN 4 -CF 3 0 HHHO 4-F 4-OHCF 2 4-Cl 0 HHHO 3-Cl 4-OHCF 2 4-CF 3 0 HHHO 4-Cl 4-OHCF 2 4-OCF 3 0 HHHO 3-Br 4-OHCF 2 4-Cl 0 HHHO 3-CH 3 4-OHCF 2 4-CF 3 0 HHHO 4-CF 3 4-OHCF 2 4-OCF 3 0 HHHO 3-OCH 3 4-OHCF 2 4-Cl 0 HHHO 3-OCHF 2 4-OHCF 2 4-CF 3 0 HHHO 4-OCHF 2 4-OHCF 2 4-OCF 3 0 HHHO 3-OCF 2 Br 4-OHCF 2 4-Cl 0 HHHO 3-OCF 3 4-OHCF 2 4-CF 3 0 HHHO 3-OCH 2 CF 3 4-OHCF 2 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4-OHCF 2 4-Cl 0 HHHO 3-SCHF 2 4-OHCF 2 4-CF 3 0 HHHO 3-SCF 3 4-OHCF 2 4-OCF 3 0 HHHO 3-NO 2 4-OHCF 2 4-Cl 0 HHHO 3-CN 4-OHCF 2 4-CF 3 0 HHHO 3-OSO 2 CH 3 4-OHCF 2 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-OHCF 2 4-Cl 0 HHHO 4-OSO 2 CF 3 4-OHCF 2 4-CF 3 0 HHHO 3,4-F 2 4-OHCF 2 4-OCF 3 0 HHHO 3,5-F 2 4-OHCF 2 4-Cl ────────── ────────────────────────

【００８３】[0083]

【表４９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 4-OHCF2 4-CF3 0 H H H O 4-F 4-OSO2CF3 4-Cl 0 H H H O 3-Cl 4-OSO2CF3 4-CF3 0 H H H O 4-Cl 4-OSO2CF3 4-OCF3 0 H H H O 3-Br 4-OSO2CF3 4-Cl 0 H H H O 3-CH3 4-OSO2CF3 4-CF3 0 H H H O 4-CF3 4-OSO2CF3 4-OCF3 0 H H H O 3-OCH3 4-OSO2CF3 4-Cl 0 H H H O 3-OCHF2 4-OSO2CF3 4-CF3 0 H H H O 4-OCHF2 4-OSO2CF3 4-OCF3 0 H H H O 3-OCF2Br 4-OSO2CF3 4-Cl 0 H H H O 3-OCF3 4-OSO2CF3 4-CF3 0 H H H O 3-OCH2CF3 4-OSO2CF3 4-OCF3 0 H H H O 3-OCF2CHF2 4-OSO2CF3 4-Cl 0 H H H O 3-SCHF2 4-OSO2CF3 4-CF3 0 H H H O 3-SCF3 4-OSO2CF3 4-OCF3 0 H H H O 3-NO2 4-OSO2CF3 4-Cl 0 H H H O 3-CN 4-OSO2CF3 4-CF3 0 H H H O 3-OSO2CH3 4-OSO2CF3 4-OCF3 0 H H H O 3-OSO2CF3 4-OSO2CF3 4-Cl 0 H H H O 4-OSO2CF3 4-OSO2CF3 4-CF3 0 H H H O 3,4-F2 4-OSO2CF3 4-OCF3 0 H H H O 3,5-F2 4-OSO2CF3 4-Cl ───────────────────────────────────[Table 49] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OHCF 2 4-CF 3 0 HHHO 4-F 4-OSO 2 CF 3 4-Cl 0 HHHO 3-Cl 4-OSO 2 CF 3 4-CF 3 0 HHHO 4-Cl 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-Br 4-OSO 2 CF 3 4-Cl 0 HHHO 3-CH 3 4-OSO 2 CF 3 4-CF 3 0 HHHO 4-CF 3 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-OCH 3 4-OSO 2 CF 3 4-Cl 0 HHHO 3-OCHF 2 4-OSO 2 CF 3 4-CF 3 0 HHHO 4-OCHF 2 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-OCF 2 Br 4- OSO 2 CF 3 4-Cl 0 HHHO 3-OCF 3 4-OSO 2 CF 3 4-CF 3 0 HHHO 3-OCH 2 CF 3 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4 -OSO 2 CF 3 4-Cl 0 HHHO 3-SCHF 2 4-OSO 2 CF 3 4-CF 3 0 HHHO 3-SCF 3 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-NO 2 4-OSO 2 CF 3 4-Cl 0 HHHO 3-CN 4-OSO 2 CF 3 4-CF 3 0 HHHO 3-OSO 2 CH 3 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4-OSO 2 CF 3 4-Cl 0 HHHO 4-OSO 2 CF 3 4-OSO 2 CF 3 4-CF 3 0 HHHO 3 , 4-F 2 4-OSO 2 CF 3 4-OCF 3 0 HHHO 3,5-F 2 4-OSO 2 CF 3 4-Cl ─────────────────── ─────────────────

【００８４】[0084]

【表５０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 4-OSO2CF3 4-CF3 0 H H H O 4-F 4-OCF2CHF2 4-Cl 0 H H H O 3-Cl 4-OCF2CHF2 4-CF3 0 H H H O 4-Cl 4-OCF2CHF2 4-OCF3 0 H H H O 3-Br 4-OCF2CHF2 4-Cl 0 H H H O 3-CH3 4-OCF2CHF2 4-CF3 0 H H H O 4-CF3 4-OCF2CHF2 4-OCF3 0 H H H O 3-OCH3 4-OCF2CHF2 4-Cl 0 H H H O 3-OCHF2 4-OCF2CHF2 4-CF3 0 H H H O 4-OCHF2 4-OCF2CHF2 4-OCF3 0 H H H O 3-OCF2Br 4-OCF2CHF2 4-Cl 0 H H H O 3-OCF3 4-OCF2CHF2 4-CF3 0 H H H O 3-OCH2CF3 4-OCF2CHF2 4-OCF3 0 H H H O 3-OCF2CHF2 4-OCF2CHF2 4-Cl 0 H H H O 3-SCHF2 4-OCF2CHF2 4-CF3 0 H H H O 3-SCF3 4-OCF2CHF2 4-OCF3 0 H H H O 3-NO2 4-OCF2CHF2 4-Cl 0 H H H O 3-CN 4-OCF2CHF2 4-CF3 0 H H H O 3-OSO2CH3 4-OCF2CHF2 4-OCF3 0 H H H O 3-OSO2CF3 4-OCF2CHF2 4-Cl 0 H H H O 4-OSO2CF3 4-OCF2CHF2 4-CF3 0 H H H O 3,4-F2 4-OCF2CHF2 4-OCF3 0 H H H O 3,5-F2 4-OCF2CHF2 4-Cl ───────────────────────────────────[Table 50] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OSO 2 CF 3 4-CF 3 0 HHHO 4-F 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-Cl 4-OCF 2 CHF 2 4-CF 3 0 HHHO 4-Cl 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-Br 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-CH 3 4-OCF 2 CHF 2 4-CF 3 0 HHHO 4-CF 3 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3- OCH 3 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-OCHF 2 4-OCF 2 CHF 2 4-CF 3 0 HHHO 4-OCHF 2 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-OCF 2 Br 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-OCF 3 4-OCF 2 CHF 2 4-CF 3 0 HHHO 3-OCH 2 CF 3 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 4-OCF 2 CHF 2 4-Cl 0 HHHO 3-SCHF 2 4-OCF 2 CHF 2 4-CF 3 0 HHHO 3-SCF 3 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-NO 2 4- OCF 2 CHF 2 4-Cl 0 HHHO 3-CN 4-OCF 2 CHF 2 4-CF 3 0 HHHO 3-OSO 2 CH 3 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3-OSO 2 CF 3 4- OCF 2 CHF 2 4-Cl 0 HHHO 4-OSO 2 CF 3 4-OCF 2 CHF 2 4-CF 3 0 HHHO 3,4-F 2 4-OCF 2 CHF 2 4-OCF 3 0 HHHO 3,5-F 2 4-OCF 2 CHF 2 4-Cl ───────── ────────────────────────────

【００８５】[0085]

【表５１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 4-OCF2CHF2 4-CF3 0 H H H O 4-F 2,4-F2 4-Cl 0 H H H O 3-Cl 2,4-F2 4-CF3 0 H H H O 4-Cl 2,4-F2 4-OCF3 0 H H H O 3-Br 2,4-F2 4-Cl 0 H H H O 3-CH3 2,4-F2 4-CF3 0 H H H O 4-CF3 2,4-F2 4-OCF3 0 H H H O 3-OCH3 2,4-F2 4-Cl 0 H H H O 3-OCHF2 2,4-F2 4-CF3 0 H H H O 4-OCHF2 2,4-F2 4-OCF3 0 H H H O 3-OCF2Br 2,4-F2 4-Cl 0 H H H O 3-OCF3 2,4-F2 4-CF3 0 H H H O 3-OCH2CF3 2,4-F2 4-OCF3 0 H H H O 3-OCF2CHF2 2,4-F2 4-Cl 0 H H H O 3-SCHF2 2,4-F2 4-CF3 0 H H H O 3-SCF3 2,4-F2 4-OCF3 0 H H H O 3-NO2 2,4-F2 4-Cl 0 H H H O 3-CN 2,4-F2 4-CF3 0 H H H O 3-OSO2CH3 2,4-F2 4-OCF3 0 H H H O 3-OSO2CF3 2,4-F2 4-Cl 0 H H H O 4-OSO2CF3 2,4-F2 4-CF3 0 H H H O 3,4-F2 2,4-F2 4-OCF3 0 H H H O 3,5-F2 2,4-F2 4-Cl ───────────────────────────────────[Table 51] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 4-OCF 2 CHF 2 4-CF 3 0 HHHO 4-F 2,4-F 2 4-Cl 0 HHHO 3-Cl 2,4-F 2 4-CF 3 0 HHHO 4-Cl 2,4-F 2 4-OCF 3 0 HHHO 3-Br 2,4-F 2 4-Cl 0 HHHO 3-CH 3 2,4-F 2 4-CF 3 0 HHHO 4-CF 3 2,4-F 2 4-OCF 3 0 HHHO 3- OCH 3, 2,4-F 2 4-Cl 0 HHHO 3-OCHF 2 2,4-F 2 4-CF 3 0 HHHO 4-OCHF 2 2,4-F 2 4-OCF 3 0 HHHO 3-OCF 2 Br 2,4-F 2 4-Cl 0 HHHO 3-OCF 3 2,4-F 2 4-CF 3 0 HHHO 3-OCH 2 CF 3 2,4-F 2 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 2,4-F 2 4-Cl 0 HHHO 3-SCHF 2 2,4-F 2 4-CF 3 0 HHHO 3-SCF 3 2,4-F 2 4-OCF 3 0 HHHO 3-NO 2 2, 4-F 2 4-Cl 0 HHHO 3-CN 2,4-F 2 4-CF 3 0 HHHO 3-OSO 2 CH 3 2,4-F 2 4-OCF 3 0 HHHO 3-OSO 2 CF 3 2, 4-F 2 4-Cl 0 HHHO 4-OSO 2 CF 3 2,4-F 2 4-CF 3 0 HHHO 3,4-F 2 2,4-F 2 4-OCF 3 0 HHHO 3,5-F 2 2,4-F 2 4-Cl ────────────── ────────────────────

【００８６】[0086]

【表５２】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 2,4-F2 4-CF3 0 H H H O 4-F 3,4-F2 4-Cl 0 H H H O 3-Cl 3,4-F2 4-CF3 0 H H H O 4-Cl 3,4-F2 4-OCF3 0 H H H O 3-Br 3,4-F2 4-Cl 0 H H H O 3-CH3 3,4-F2 4-CF3 0 H H H O 4-CF3 3,4-F2 4-OCF3 0 H H H O 3-OCH3 3,4-F2 4-Cl 0 H H H O 3-OCHF2 3,4-F2 4-CF3 0 H H H O 4-OCHF2 3,4-F2 4-OCF3 0 H H H O 3-OCF2Br 3,4-F2 4-Cl 0 H H H O 3-OCF3 3,4-F2 4-CF3 0 H H H O 3-OCH2CF3 3,4-F2 4-OCF3 0 H H H O 3-OCF2CHF2 3,4-F2 4-Cl 0 H H H O 3-SCHF2 3,4-F2 4-CF3 0 H H H O 3-SCF3 3,4-F2 4-OCF3 0 H H H O 3-NO2 3,4-F2 4-Cl 0 H H H O 3-CN 3,4-F2 4-CF3 0 H H H O 3-OSO2CH3 3,4-F2 4-OCF3 0 H H H O 3-OSO2CF3 3,4-F2 4-Cl 0 H H H O 4-OSO2CF3 3,4-F2 4-CF3 0 H H H O 3,4-F2 3,4-F2 4-OCF3 0 H H H O 3,5-F2 3,4-F2 4-Cl ───────────────────────────────────[Table 52] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 2,4- F 2 4-CF 3 0 HHHO 4-F 3,4-F 2 4-Cl 0 HHHO 3-Cl 3,4-F 2 4-CF 3 0 HHHO 4-Cl 3,4-F 2 4-OCF 3 0 HHHO 3-Br 3,4-F 2 4-Cl 0 HHHO 3-CH 3 3,4-F 2 4-CF 3 0 HHHO 4-CF 3 3,4-F 2 4-OCF 3 0 HHHO 3- OCH 3 3,4-F 2 4-Cl 0 HHHO 3-OCHF 2 3,4-F 2 4-CF 3 0 HHHO 4-OCHF 2 3,4-F 2 4-OCF 3 0 HHHO 3-OCF 2 Br 3,4-F 2 4-Cl 0 HHHO 3-OCF 3 3,4-F 2 4-CF 3 0 HHHO 3-OCH 2 CF 3 3,4-F 2 4-OCF 3 0 HHHO 3-OCF 2 CHF 2 3,4-F 2 4-Cl 0 HHHO 3-SCHF 2 3,4-F 2 4-CF 3 0 HHHO 3-SCF 3 3,4-F 2 4-OCF 3 0 HHHO 3-NO 2 3, 4-F 2 4-Cl 0 HHHO 3-CN 3,4-F 2 4-CF 3 0 HHHO 3-OSO 2 CH 3 3,4-F 2 4-OCF 3 0 HHHO 3-OSO 2 CF 3 3, 4-F 2 4-Cl 0 HHHO 4-OSO 2 CF 3 3,4-F 2 4-CF 3 0 HHHO 3,4-F 2 3,4-F 2 4-OCF 3 0 HHHO 3,5-F 2 3,4-F 2 4-Cl ──────────────── ──────────────────

【００８７】[0087]

【表５３】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H O 3-Cl-4-F 3,4-F2 4-CF3 0 H H H S 3-F 4-F 4-Cl 0 H H H S 3-F 4-F 4-Br 0 H H H S 3-F 4-F 4-CF3 0 H H H S 3-F 4-F 4-OCF3 0 H H H S 3-F 4-F 4-OCHF2 0 H H H S 3-F 4-F 4-OCF2Br 0 H H H S 3-F 4-F 4-OCF2CHF2 0 H H H S 3-F 4-F 4-OSO2CF3 0 H H H S H 4-F 4-OCF3 0 H H H S 4-F 4-F 4-Cl 0 H H H S 3-Cl 4-F 4-CF3 0 H H H S 3-Br 4-F 4-OCF3 0 H H H S 3-CF3 4-F 4-Cl 0 H H H S 3-OCF3 4-F 4-CF3 0 H H H S 3-OCHF2 4-F 4-OCF3 0 H H H S 4-OCHF2 4-F 4-Cl 0 H H H S 3-F 4-Cl 4-CF3 0 H H H S 3-F 4-Br 4-OCF3 0 H H H S 3-F 4-CF3 4-Cl 0 H H H S 3-F 4-OSO2CF3 4-CF3 0 H H H S 3-F 4-CN 4-OCF3 0 H H H S 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 53] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHO 3-Cl-4-F 3,4- F 2 4-CF 3 0 HHHS 3-F 4-F 4-Cl 0 HHHS 3-F 4-F 4-Br 0 HHHS 3-F 4-F 4-CF 3 0 HHHS 3-F 4-F 4- OCF 3 0 HHHS 3-F 4-F 4-OCHF 2 0 HHHS 3-F 4-F 4-OCF 2 Br 0 HHHS 3-F 4-F 4-OCF 2 CHF 20 HHHS 3-F 4-F 4 -OSO 2 CF 3 0 HHHSH 4-F 4-OCF 3 0 HHHS 4-F 4-F 4-Cl 0 HHHS 3-Cl 4-F 4-CF 3 0 HHHS 3-Br 4-F 4-OCF 3 0 HHHS 3-CF 3 4-F 4-Cl 0 HHHS 3-OCF 3 4-F 4-CF 3 0 HHHS 3-OCHF 2 4-F 4-OCF 3 0 HHHS 4-OCHF 2 4-F 4-Cl 0 HHHS 3-F 4-Cl 4-CF 3 0 HHHS 3-F 4-Br 4-OCF 3 0 HHHS 3-F 4-CF 3 4-Cl 0 HHHS 3-F 4-OSO 2 CF 3 4-CF 3 0 HHHS 3-F 4-CN 4-OCF 3 0 HHHS 3-F 3,4-F 2 4-Cl ───────────────────────── ───────────

【００８８】[0088]

【表５４】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H H S 3-CF3 4-CN 4-CF3 0 H H CH3 O 3-F 4-F 4-Cl 0 H H CH3 O 3-F 4-F 4-Br 0 H H CH3 O 3-F 4-F 4-CF3 0 H H CH3 O 3-F 4-F 4-OCF3 0 H H CH3 O 3-F 4-F 4-OCHF2 0 H H CH3 O 3-F 4-F 4-OCF2Br 0 H H CH3 O 3-F 4-F 4-OCF2CHF2 0 H H CH3 O 3-F 4-F 4-OSO2CF3 0 H H CH3 O H 4-F 4-OCF3 0 H H CH3 S 4-F 4-F 4-Cl 0 H H CH3 O 3-Cl 4-F 4-CF3 0 H H CH3 O 3-Br 4-F 4-OCF3 0 H H CH3 O 3-CF3 4-F 4-Cl 0 H H CH3 O 3-OCF3 4-F 4-CF3 0 H H CH3 O 3-OCHF2 4-F 4-OCF3 0 H H CH3 O 4-OCHF2 4-F 4-Cl 0 H H CH3 S 3-F 4-Cl 4-CF3 0 H H CH3 O 3-F 4-Br 4-OCF3 0 H H CH3 O 3-F 4-CF3 4-Cl 0 H H CH3 O 3-F 4-OSO2CF3 4-CF3 0 H H CH3 O 3-F 4-CN 4-OCF3 0 H H CH3 O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 54] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HHHS 3-CF 3 4-CN 4-CF 3 0 HH CH 3 O 3-F 4-F 4-Cl 0 HH CH 3 O 3-F 4-F 4-Br 0 HH CH 3 O 3-F 4-F 4-CF 3 0 HH CH 3 O 3- F 4-F 4-OCF 3 0 HH CH 3 O 3-F 4-F 4-OCHF 20 HH CH 3 O 3-F 4-F 4-OCF 2 Br 0 HH CH 3 O 3-F 4-F 4-OCF 2 CHF 2 0 HH CH 3 O 3-F 4-F 4-OSO 2 CF 3 0 HH CH 3 OH 4-F 4-OCF 3 0 HH CH 3 S 4-F 4-F 4-Cl 0 HH CH 3 O 3-Cl 4-F 4-CF 3 0 HH CH 3 O 3-Br 4-F 4-OCF 3 0 HH CH 3 O 3-CF 3 4-F 4-Cl 0 HH CH 3 O 3 -OCF 3 4-F 4-CF 3 0 HH CH 3 O 3-OCHF 2 4-F 4-OCF 3 0 HH CH 3 O 4-OCHF 2 4-F 4-Cl 0 HH CH 3 S 3-F 4 -Cl 4-CF 3 0 HH CH 3 O 3-F 4-Br 4-OCF 3 0 HH CH 3 O 3-F 4-CF 3 4-Cl 0 HH CH 3 O 3-F 4-OSO 2 CF 3 4-CF 30 HH CH 3 O 3-F 4-CN 4-OCF 30 HH CH 3 O 3-F 3,4-F 2 4-Cl ────────────── ───────────── ────────

【００８９】[0089]

【表５５】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H CH3 O 3-CF3 4-CN 4-CF3 0 H CH3 H O 3-F 4-F 4-Cl 0 H CH3 H O 3-F 4-F 4-Br 0 H CH3 H O 3-F 4-F 4-CF3 0 H CH3 H O 3-F 4-F 4-OCF3 0 H CH3 H O 3-F 4-F 4-OCHF2 0 H CH3 H O 3-F 4-F 4-OCF2Br 0 H CH3 H O 3-F 4-F 4-OCF2CHF2 0 H CH3 H O 3-F 4-F 4-OSO2CF3 0 H CH3 H O H 4-F 4-OCF3 0 H CH3 H S 4-F 4-F 4-Cl 0 H CH3 H O 3-Cl 4-F 4-CF3 0 H CH3 H O 3-Br 4-F 4-OCF3 0 H CH3 H O 3-CF3 4-F 4-Cl 0 H CH3 H O 3-OCF3 4-F 4-CF3 0 H CH3 H O 3-OCHF2 4-F 4-OCF3 0 H CH3 H O 4-OCHF2 4-F 4-Cl 0 H CH3 H S 3-F 4-Cl 4-CF3 0 H CH3 H O 3-F 4-Br 4-OCF3 0 H CH3 H O 3-F 4-CF3 4-Cl 0 H CH3 H O 3-F 4-OSO2CF3 4-CF3 0 H CH3 H O 3-F 4-CN 4-OCF3 0 H CH3 H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 55] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HH CH 3 O 3-CF 3 4-CN 4 -CF 3 0 H CH 3 HO 3-F 4-F 4-Cl 0 H CH 3 HO 3-F 4-F 4-Br 0 H CH 3 HO 3-F 4-F 4-CF 3 0 H CH 3 HO 3-F 4-F 4-OCF 3 0 H CH 3 HO 3-F 4-F 4-OCHF 2 0 H CH 3 HO 3-F 4-F 4-OCF 2 Br 0 H CH 3 HO 3-F 4-F 4-OCF 2 CHF 20 H CH 3 HO 3-F 4-F 4-OSO 2 CF 3 0 H CH 3 HOH 4-F 4-OCF 3 0 H CH 3 HS 4-F 4-F 4 -Cl 0 H CH 3 HO 3-Cl 4-F 4-CF 3 0 H CH 3 HO 3-Br 4-F 4-OCF 3 0 H CH 3 HO 3-CF 3 4-F 4-Cl 0 H CH 3 HO 3-OCF 3 4-F 4-CF 3 0 H CH 3 HO 3-OCHF 2 4-F 4-OCF 3 0 H CH 3 HO 4-OCHF 2 4-F 4-Cl 0 H CH 3 HS 3 -F 4-Cl 4-CF 3 0 H CH 3 HO 3-F 4-Br 4-OCF 3 0 H CH 3 HO 3-F 4-CF 3 4-Cl 0 H CH 3 HO 3-F 4-OSO 2 CF 3 4-CF 3 0 H CH 3 HO 3-F 4-CN 4-OCF 3 0 H CH 3 HO 3-F 3,4-F 2 4-Cl ─────────── ───────────── ──────────

【００９０】[0090]

【表５６】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H CH3 H O 3-CF3 4-CN 4-CF3 0 CH3 H H O 3-F 4-F 4-Cl 0 CH3 H H O 3-F 4-F 4-Br 0 CH3 H H O 3-F 4-F 4-CF3 0 CH3 H H O 3-F 4-F 4-OCF3 0 CH3 H H O 3-F 4-F 4-OCHF2 0 CH3 H H O 3-F 4-F 4-OCF2Br 0 CH3 H H O 3-F 4-F 4-OCF2CHF2 0 CH3 H H O 3-F 4-F 4-OSO2CF3 0 CH3 H H O H 4-F 4-OCF3 0 CH3 H H S 4-F 4-F 4-Cl 0 CH3 H H O 3-Cl 4-F 4-CF3 0 CH3 H H O 3-Br 4-F 4-OCF3 0 CH3 H H O 3-CF3 4-F 4-Cl 0 CH3 H H O 3-OCF3 4-F 4-CF3 0 CH3 H H O 3-OCHF2 4-F 4-OCF3 0 CH3 H H O 4-OCHF2 4-F 4-Cl 0 CH3 H H S 3-F 4-Cl 4-CF3 0 CH3 H H O 3-F 4-Br 4-OCF3 0 CH3 H H O 3-F 4-CF3 4-Cl 0 CH3 H H O 3-F 4-OSO2CF3 4-CF3 0 CH3 H H O 3-F 4-CN 4-OCF3 0 CH3 H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 56] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 H CH 3 HO 3-CF 3 4-CN 4 -CF 3 0 CH 3 HHO 3-F 4-F 4-Cl 0 CH 3 HHO 3-F 4-F 4-Br 0 CH 3 HHO 3-F 4-F 4-CF 3 0 CH 3 HHO 3-F 4-F 4-OCF 30 CH 3 HHO 3-F 4-F 4-OCHF 20 CH 3 HHO 3-F 4-F 4-OCF 2 Br 0 CH 3 HHO 3-F 4-F 4-OCF 2 CHF 20 CH 3 HHO 3-F 4-F 4-OSO 2 CF 3 0 CH 3 HHOH 4-F 4-OCF 3 0 CH 3 HHS 4-F 4-F 4-Cl 0 CH 3 HHO 3-Cl 4 -F 4-CF 3 0 CH 3 HHO 3-Br 4-F 4-OCF 3 0 CH 3 HHO 3-CF 3 4-F 4-Cl 0 CH 3 HHO 3-OCF 3 4-F 4-CF 3 0 CH 3 HHO 3-OCHF 2 4-F 4-OCF 3 0 CH 3 HHO 4-OCHF 2 4-F 4-Cl 0 CH 3 HHS 3-F 4-Cl 4-CF 3 0 CH 3 HHO 3-F 4 -Br 4-OCF 3 0 CH 3 HHO 3-F 4-CF 3 4-Cl 0 CH 3 HHO 3-F 4-OSO 2 CF 3 4-CF 3 0 CH 3 HHO 3-F 4-CN 4-OCF 3 0 CH 3 HHO 3-F 3,4-F 2 4-Cl ───────────────────────────────── ───

【００９１】[0091]

【表５７】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 CH3 H H O 3-CF3 4-CN 4-CF3 0 H H CH2CH3 O 3-F 4-F 4-Cl 0 H H CH2CH2CH3 O 3-F 4-F 4-Br 0 H H CH2CH2CH2CH3 O 3-F 4-F 4-CF3 0 H H CH(CH3)2 O 3-F 4-F 4-OCF3 0 H H C(CH3)3 O 3-F 4-F 4-OCHF2 0 H H CH2CH=CH2 O 3-F 4-F 4-OCF2Br 0 H H CH2Ｃ≡CH O 3-F 4-F 4-OCF2CHF2 0 H H CH2OCH3 O 3-F 4-F 4-OSO2CF3 0 H H CH2OCH2CH3 O H 4-F 4-OCF3 0 H H CH2CH2OCH3 O 4-F 4-F 4-Cl 0 H H CHF2 O 3-Cl 4-F 4-CF3 0 H H CBrF2 O 3-Br 4-F 4-OCF3 0 H H CF3 O 3-CF3 4-F 4-Cl 0 H H COCH3 O 3-OCF3 4-F 4-CF3 0 H H COCF3 O 3-OCHF2 4-F 4-OCF3 0 H H CO2CH3 O 4-OCHF2 4-F 4-Cl 0 H H CH2C6H5 O 3-F 4-Cl 4-CF3 0 H H SC6H5 O 3-F 4-Br 4-OCF3 0 H H SCCl3 O 3-F 4-CF3 4-Cl 0 H H SCO2CH2CH3 O 3-F 4-OSO2CF3 4-CF3 0 H H S(C6H4-2-NO2) O 3-F 4-CN 4-OCF3 0 H H SN(CH2CH2CH2CH3)2 O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 57] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 CH 3 HHO 3-CF 3 4-CN 4- CF 3 0 HH CH 2 CH 3 O 3-F 4-F 4-Cl 0 HH CH 2 CH 2 CH 3 O 3-F 4-F 4-Br 0 HH CH 2 CH 2 CH 2 CH 3 O 3-F 4-F 4-CF 3 0 HH CH (CH 3 ) 2 O 3-F 4-F 4-OCF 30 HHC (CH 3 ) 3 O 3-F 4-F 4-OCHF 20 HH CH 2 CH = CH 2 O 3-F 4-F 4-OCF 2 Br 0 HH CH 2 C ≡ CH O 3-F 4-F 4-OCF 2 CHF 2 0 HH CH 2 OCH 3 O 3-F 4-F 4-OSO 2 CF 3 0 HH CH 2 OCH 2 CH 3 OH 4-F 4-OCF 3 0 HH CH 2 CH 2 OCH 3 O 4-F 4-F 4-Cl 0 HH CHF 2 O 3-Cl 4-F 4- CF 3 0 HH CBrF 2 O 3-Br 4-F 4-OCF 3 0 HH CF 3 O 3-CF 3 4-F 4-Cl 0 HH COCH 3 O 3-OCF 3 4-F 4-CF 3 0 HH COCF 3 O 3-OCHF 2 4-F 4-OCF 3 0 HH CO 2 CH 3 O 4-OCHF 2 4-F 4-Cl 0 HH CH 2 C 6 H 5 O 3-F 4-Cl 4-CF 3 0 HH SC 6 H 5 O 3-F 4-Br 4-OCF 3 0 HH SCCl 3 O 3-F 4-CF 3 4-Cl 0 HH SCO 2 CH 2 CH 3 O 3-F 4-OSO 2 CF 3 4-CF 3 0 HHS (C 6 H 4 -2-NO 2 ) O 3-F 4-CN 4-OCF 3 0 HH SN (CH 2 CH 2 CH 2 CH 3 ) 2 O 3-F 3,4-F 2 4-Cl ──── ───────────────────────────────

【００９２】[0092]

【表５８】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H H SN(CH3)CO2CH2CH3 O 3-CF3 4-CN 4-CF3 0 H CH2CH3 H O 3-F 4-F 4-Cl 0 H CH2CH2CH3 H O 3-F 4-F 4-Br 0 H CH2CH2CH2CH3 H O 3-F 4-F 4-CF3 0 H CH(CH3)2 H O 3-F 4-F 4-OCF3 0 H C(CH3)3 H O 3-F 4-F 4-OCHF2 0 H CH2CH=CH2 H O 3-F 4-F 4-OCF2Br 0 H CH2Ｃ≡CH H O 3-F 4-F 4-OCF2CHF2 0 H CH2OCH3 H O 3-F 4-F 4-OSO2CF3 0 H CH2OCH2CH3 H O H 4-F 4-OCF3 0 H CH2CH2OCH3 H O 4-F 4-F 4-Cl 0 H CHF2 H O 3-Cl 4-F 4-CF3 0 H CBrF2 H O 3-Br 4-F 4-OCF3 0 H CF3 H O 3-CF3 4-F 4-Cl 0 H COCH3 H O 3-OCF3 4-F 4-CF3 0 H COCF3 H O 3-OCHF2 4-F 4-OCF3 0 H CO2CH3 H O 4-OCHF2 4-F 4-Cl 0 H CH2C6H5 H O 3-F 4-Cl 4-CF3 0 H SC6H5 H O 3-F 4-Br 4-OCF3 0 H SCCl3 H O 3-F 4-CF3 4-Cl 0 H SCO2CH2CH3 H O 3-F 4-OSO2CF3 4-CF3 0 H S(C6H4-2-NO2) H O 3-F 4-CN 4-OCF3 0 H SN(CH2CH2CH2CH3)2 H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 58] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 HH SN (CH 3 ) CO 2 CH 2 CH 3 O 3-CF 3 4-CN 4-CF 3 0 H CH 2 CH 3 HO 3-F 4-F 4-Cl 0 H CH 2 CH 2 CH 3 HO 3-F 4- F 4-Br 0 H CH 2 CH 2 CH 2 CH 3 HO 3-F 4-F 4-CF 3 0 H CH (CH 3 ) 2 HO 3-F 4-F 4-OCF 3 0 HC (CH 3 ) 3 HO 3-F 4-F 4-OCHF 2 0 H CH 2 CH = CH 2 HO 3-F 4-F 4-OCF 2 Br 0 H CH 2 C ≡ CH HO 3-F 4-F 4-OCF 2 CHF 2 0 H CH 2 OCH 3 HO 3-F 4-F 4-OSO 2 CF 3 0 H CH 2 OCH 2 CH 3 HOH 4-F 4-OCF 3 0 H CH 2 CH 2 OCH 3 HO 4-F 4 -F 4-Cl 0 H CHF 2 HO 3-Cl 4-F 4-CF 3 0 H CBrF 2 HO 3-Br 4-F 4-OCF 3 0 H CF 3 HO 3-CF 3 4-F 4-Cl 0 H COCH 3 HO 3-OCF 3 4-F 4-CF 3 0 H COCF 3 HO 3-OCHF 2 4-F 4-OCF 3 0 H CO 2 CH 3 HO 4-OCHF 2 4-F 4-Cl 0 H CH 2 C 6 H 5 HO 3-F 4-Cl 4-CF 3 0 H SC 6 H 5 HO 3-F 4-Br 4-OCF 3 0 H SCCl 3 HO 3-F 4-CF 3 4-Cl 0 H SCO 2 CH 2 CH 3 HO 3-F 4-OSO 2 CF 3 4-CF 3 0 HS (C 6 H 4 -2-NO 2 ) HO 3-F 4-CN 4-OCF 3 0 H SN ( CH 2 CH 2 CH 2 CH 3 ) 2 HO 3-F 3,4-F 2 4-Cl ─────── ───────────────────────────

【００９３】[0093]

【表５９】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 H SN(CH3)CO2CH2CH3 H O 3-CF3 4-CN 4-CF3 0 CH2CH3 H H O 3-F 4-F 4-Cl 0 CH2CH2CH3 H H O 3-F 4-F 4-Br 0 CH2CH2CH2CH3 H H O 3-F 4-F 4-CF3 0 CH(CH3)2 H H O 3-F 4-F 4-OCF3 0 C(CH3)3 H H O 3-F 4-F 4-OCHF2 0 Q1 H H O 3-F 4-F 4-OCF2Br 0 Q4 H H O 3-F 4-F 4-OCF2CHF2 0 F H H O 3-F 4-F 4-OSO2CF3 0 Cl H H O H 4-F 4-OCF3 0 Br H H O 4-F 4-F 4-Cl 0 I H H O 3-Cl 4-F 4-CF3 0 OH H H O 3-Br 4-F 4-OCF3 0 CN H H O 3-CF3 4-F 4-Cl 0 NO2 H H O 3-OCF3 4-F 4-CF3 0 CH2F H H O 3-OCHF2 4-F 4-OCF3 0 CF3 H H O 4-OCHF2 4-F 4-Cl 0 OCH3 H H O 3-F 4-Cl 4-CF3 0 OCH2CH3 H H O 3-F 4-Br 4-OCF3 0 OCF3 H H O 3-F 4-CF3 4-Cl 0 SCH3 H H O 3-F 4-OSO2CF3 4-CF3 0 SCF3 H H O 3-F 4-CN 4-OCF3 0 SO2CH3 H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 59] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 H SN (CH 3 ) CO 2 CH 2 CH 3 HO 3-CF 3 4-CN 4-CF 3 0 CH 2 CH 3 HHO 3-F 4-F 4-Cl 0 CH 2 CH 2 CH 3 HHO 3-F 4-F 4-Br 0 CH 2 CH 2 CH 2 CH 3 HHO 3-F 4-F 4-CF 30 CH (CH 3 ) 2 HHO 3-F 4-F 4-OCF 3 0 C (CH 3 ) 3 HHO 3-F 4-F 4-OCHF 2 0 Q1 HHO 3-F 4-F 4-OCF 2 Br 0 Q4 HHO 3-F 4-F 4-OCF 2 CHF 2 0 FHHO 3-F 4-F 4-OSO 2 CF 3 0 Cl HHOH 4-F 4 -OCF 3 0 Br HHO 4-F 4-F 4-Cl 0 IHHO 3-Cl 4-F 4-CF 3 0 OH HHO 3-Br 4-F 4-OCF 3 0 CN HHO 3-CF 3 4-F 4-Cl 0 NO 2 HHO 3-OCF 3 4-F 4-CF 3 0 CH 2 FHHO 3-OCHF 2 4-F 4-OCF 3 0 CF 3 HHO 4-OCHF 2 4-F 4-Cl 0 OCH 3 HHO 3-F 4-Cl 4-CF 3 0 OCH 2 CH 3 HHO 3-F 4-Br 4-OCF 3 0 OCF 3 HHO 3-F 4-CF 3 4-Cl 0 SCH 3 HHO 3-F 4- OSO 2 CF 3 4-CF 30 SCF 3 HHO 3-F 4-CN 4-OCF 3 0 SO 2 CH 3 HHO 3-F 3,4-F 2 4-Cl ─────────── ── ──────────────────────

【００９４】[0094]

【表６０】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 SO2CF3 H H O 3-CF3 4-CN 4-CF3 0 OSO2CF3 H H O 3-F 4-F 4-Cl 0 CO2CH2CH3 H H O 3-F 4-F 4-Br 0 CO2CH3 H H O 3-F 4-F 4-CF3 0 CH2CO2CH3 H H O 3-F 4-F 4-OCF3 0 N(CH3)2 H H O 3-F 4-F 4-OCHF2 0 C6H5 H H O 3-F 4-F 4-OCF2Br 0 C6H4-4-F H H O 3-F 4-F 4-OCF2CHF2 0 C6H4-4-Cl H H O 3-F 4-F 4-OSO2CF3 0 C6H4-4-Br H H O H 4-F 4-OCF3 0 C6H4-4-CN H H O 4-F 4-F 4-Cl 0 C6H4-4-CF3 H H O 3-Cl 4-F 4-CF3 0 CH2C6H5 H H O 3-Br 4-F 4-OCF3 0 CH3 CH3 CH3 O 3-F 4-F 4-Cl 0 CH3 CH3 CH3 O 3-F 4-F 4-Br 0 CH3 CH3 CH3 O 3-F 4-F 4-CF3 0 CH3 CH3 CH3 O 3-F 4-F 4-OCF3 0 CH3 CH3 CH3 O 3-F 4-F 4-OCHF2 0 CH3 CH3 CH3 O 3-F 4-F 4-OCF2Br 0 CH3 CH3 CH3 O 3-F 4-F 4-OCF2CHF2 0 CH3 CH3 CH3 O 3-F 4-F 4-OSO2CF3 0 CH3 CH3 CH3 O H 4-F 4-OCF3 0 CH3 CH3 CH3 O 4-F 4-F 4-Cl ───────────────────────────────────[Table 60] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 SO 2 CF 3 HHO 3-CF 3 4-CN 4-CF 3 0 OSO 2 CF 3 HHO 3-F 4-F 4-Cl 0 CO 2 CH 2 CH 3 HHO 3-F 4-F 4-Br 0 CO 2 CH 3 HHO 3-F 4-F 4- CF 3 0 CH 2 CO 2 CH 3 HHO 3-F 4-F 4-OCF 3 0 N (CH 3 ) 2 HHO 3-F 4-F 4-OCHF 2 0 C 6 H 5 HHO 3-F 4-F 4-OCF 2 Br 0 C 6 H 4 -4-FHHO 3-F 4-F 4-OCF 2 CHF 2 0 C 6 H 4 -4-Cl HHO 3-F 4-F 4-OSO 2 CF 3 0 C 6 H 4 -4-Br HHOH 4-F 4-OCF 3 0 C 6 H 4 -4-CN HHO 4-F 4-F 4-Cl 0 C 6 H 4 -4-CF 3 HHO 3-Cl 4- F 4-CF 3 0 CH 2 C 6 H 5 HHO 3-Br 4-F 4-OCF 3 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-Cl 0 CH 3 CH 3 CH 3 O 3- F 4-F 4-Br 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-CF 3 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-OCF 3 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-OCHF 20 CH 3 CH 3 CH 3 O 3-F 4-F 4-OCF 2 Br 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-OCF 2 CHF 2 0 CH 3 CH 3 CH 3 O 3-F 4-F 4-OSO 2 CF 3 0 CH 3 CH 3 CH 3 OH 4-F 4-OCF 30 CH 3 CH 3 CH 3 O 4-F 4-F 4-Cl ──────────────────── ────────────────

【００９５】[0095]

【表６１】 ─────────────────────────────────── k R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 CH3 CH3 CH3 O 3-Cl 4-F 4-CF3 0 H CH2OCH3 CH3 O 3-F 4-F 4-Cl 0 H COCH3 CH3 O 3-F 4-F 4-Br 0 H CO2CH3 CH3 O 3-F 4-F 4-CF3 0 H CHF2 CH3 O 3-F 4-F 4-OCF3 0 H CH2C6H5 CH3 O 3-F 4-F 4-OCHF2 0 H SC6H5 CH3 O 3-F 4-F 4-OCF2Br 0 H CH3 CH2OCH3 O 3-F 4-F 4-OCF2CHF2 0 H CH3 COCH3 O 3-F 4-F 4-OSO2CF3 0 H CH3 CO2CH3 O H 4-F 4-OCF3 0 H CH3 CHF2 O 4-F 4-F 4-Cl 0 H CH3 CH2C6H5 O 3-Cl 4-F 4-CF3 0 H CH3 SC6H5 O 3-Br 4-F 4-OCF3 0 CH3 CH3 CH2OCH3 O 3-CF3 4-F 4-Cl 0 CH3 CH3 COCH3 O 3-OCF3 4-F 4-CF3 0 CH3 CH3 CO2CH3 O 3-OCHF2 4-F 4-OCF3 0 CH3 CH3 CHF2 O 4-OCHF2 4-F 4-Cl 0 CH3 CH3 CH2C6H5 O 3-F 4-Cl 4-CF3 0 C6H5 CH3 SC6H5 O 3-F 4-Br 4-OCF3 0 Br CH3 CH3 O 3-F 4-CF3 4-Cl 0 CN CH3 CH3 O 3-F 4-OSO2CF3 4-CF3 0 OH CH3 CH3 O 3-F 4-CN 4-OCF3 0 C6H5 CH3 CH3 O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 61] ─────────────────────────────────── k R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 CH 3 CH 3 CH 3 O 3-Cl 4- F 4-CF 3 0 H CH 2 OCH 3 CH 3 O 3-F 4-F 4-Cl 0 H COCH 3 CH 3 O 3-F 4-F 4-Br 0 H CO 2 CH 3 CH 3 O 3- F 4-F 4-CF 3 0 H CHF 2 CH 3 O 3-F 4-F 4-OCF 3 0 H CH 2 C 6 H 5 CH 3 O 3-F 4-F 4-OCHF 2 0 H SC 6 H 5 CH 3 O 3-F 4-F 4-OCF 2 Br 0 H CH 3 CH 2 OCH 3 O 3-F 4-F 4-OCF 2 CHF 20 H CH 3 COCH 3 O 3-F 4-F 4-OSO 2 CF 3 0 H CH 3 CO 2 CH 3 OH 4-F 4-OCF 3 0 H CH 3 CHF 2 O 4-F 4-F 4-Cl 0 H CH 3 CH 2 C 6 H 5 O 3 -Cl 4-F 4-CF 3 0 H CH 3 SC 6 H 5 O 3-Br 4-F 4-OCF 3 0 CH 3 CH 3 CH 2 OCH 3 O 3-CF 3 4-F 4-Cl 0 CH 3 CH 3 COCH 3 O 3-OCF 3 4-F 4-CF 3 0 CH 3 CH 3 CO 2 CH 3 O 3-OCHF 2 4-F 4-OCF 3 0 CH 3 CH 3 CHF 2 O 4-OCHF 2 4-F 4-Cl 0 CH 3 CH 3 CH 2 C 6 H 5 O 3-F 4-Cl 4-CF 3 0 C 6 H 5 CH 3 SC 6 H 5 O 3-F 4-Br 4-OCF 3 0 Br CH 3 CH 3 O 3-F 4-CF 3 4-Cl 0 CN CH 3 CH 3 O 3-F 4-OSO 2 CF 3 4-CF 3 0 OH CH 3 CH 3 O 3-F 4-CN 4-OCF 3 0 C 6 H 5 CH 3 CH 3 O 3-F 3,4-F 2 4-Cl ─────────────────────────────────── ─

【００９６】[0096]

【表６２】 ─────────────────────────────────── k R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 0 CH2C6H5 CH3 CH3 O 3-CF3 4-CN 4-CF3 1 H H H H O 3-F 4-F 4-Cl 1 H H H H O 3-F 4-F 4-Br 1 H H H H O 3-F 4-F 4-CF3 1 H H H H O 3-F 4-F 4-OCF3 1 H H H H O 3-F 4-F 4-OCHF2 1 H H H H O 3-F 4-F 4-OCF2Br 1 H H H H O 3-F 4-F 4-OCF2CHF2 1 H H H H O 3-F 4-F 4-OSO2CF3 1 H H H H O H 4-F 4-OCF3 1 H H H H O 4-F 4-F 4-Cl 1 H H H H O 3-Cl 4-F 4-CF3 1 H H H H O 3-Br 4-F 4-OCF3 1 H H H H O 3-CF3 4-F 4-Cl 1 H H H H O 3-OCF3 4-F 4-CF3 1 H H H H O 3-OCHF2 4-F 4-OCF3 1 H H H H O 4-OCHF2 4-F 4-Cl 1 H H H H O 3-F 4-Cl 4-CF3 1 H H H H O 3-F 4-Br 4-OCF3 1 H H H H O 3-F 4-CF3 4-Cl 1 H H H H O 3-F 4-OSO2CF3 4-CF3 1 H H H H O 3-F 4-CN 4-OCF3 1 H H H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 62] ─────────────────────────────────── k R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 0 CH 2 C 6 H 5 CH 3 CH 3 O 3-CF 3 4-CN 4-CF 3 1 HHHHO 3-F 4-F 4-Cl 1 HHHHO 3-F 4-F 4-Br 1 HHHHO 3-F 4-F 4-CF 3 1 HHHHO 3- F 4-F 4-OCF 3 1 HHHHO 3-F 4-F 4-OCHF 2 1 HHHHO 3-F 4-F 4-OCF 2 Br 1 HHHHO 3-F 4-F 4-OCF 2 CHF 2 1 HHHHO 3 -F 4-F 4-OSO 2 CF 3 1 HHHHOH 4-F 4-OCF 3 1 HHHHO 4-F 4-F 4-Cl 1 HHHHO 3-Cl 4-F 4-CF 3 1 HHHHO 3-Br 4- F 4-OCF 3 1 HHHHO 3-CF 3 4-F 4-Cl 1 HHHHO 3-OCF 3 4-F 4-CF 3 1 HHHHO 3-OCHF 2 4-F 4-OCF 3 1 HHHHO 4-OCHF 2 4 -F 4-Cl 1 HHHHO 3-F 4-Cl 4-CF 3 1 HHHHO 3-F 4-Br 4-OCF 3 1 HHHHO 3-F 4-CF 3 4-Cl 1 HHHHO 3-F 4-OSO 2 CF 3 4-CF 3 1 HHHHO 3-F 4-CN 4-OCF 3 1 HHHHO 3-F 3,4-F 2 4-Cl ─────────────────── ─────────────────

【００９７】[0097]

【表６３】 ─────────────────────────────────── k R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 1 H H H H O 3-CF3 4-CN 4-CF3 1 CH3 H H H O 3-F 4-F 4-Cl 1 CH3 H H H O 3-F 4-F 4-Br 1 CH3 H H H O 3-F 4-F 4-CF3 1 CH3 H H H O 3-F 4-F 4-OCF3 1 CH3 H H H O 3-F 4-F 4-OCHF2 1 CH3 H H H O 3-F 4-F 4-OCF2Br 1 CH3 H H H O 3-F 4-F 4-OCF2CHF2 1 CH3 H H H O 3-F 4-F 4-OSO2CF3 1 CH3 H H H O H 4-F 4-OCF3 1 CH3 H H H O 4-F 4-F 4-Cl 1 CH3 H H H O 3-Cl 4-F 4-CF3 1 CH3 H H H O 3-Br 4-F 4-OCF3 1 CH3 H H H O 3-CF3 4-F 4-Cl 1 CH3 H H H O 3-OCF3 4-F 4-CF3 1 CH3 H H H O 3-OCHF2 4-F 4-OCF3 1 CH3 H H H O 4-OCHF2 4-F 4-Cl 1 CH3 H H H O 3-F 4-Cl 4-CF3 1 CH3 H H H O 3-F 4-Br 4-OCF3 1 CH3 H H H O 3-F 4-CF3 4-Cl 1 CH3 H H H O 3-F 4-OSO2CF3 4-CF3 1 CH3 H H H O 3-F 4-CN 4-OCF3 1 CH3 H H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 63] ─────────────────────────────────── k R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 1 HHHHO 3-CF 3 4-CN 4- CF 3 1 CH 3 HHHO 3-F 4-F 4-Cl 1 CH 3 HHHO 3-F 4-F 4-Br 1 CH 3 HHHO 3-F 4-F 4-CF 3 1 CH 3 HHHO 3-F 4 -F 4-OCF 3 1 CH 3 HHHO 3-F 4-F 4-OCHF 2 1 CH 3 HHHO 3-F 4-F 4-OCF 2 Br 1 CH 3 HHHO 3-F 4-F 4-OCF 2 CHF 2 1 CH 3 HHHO 3-F 4-F 4-OSO 2 CF 3 1 CH 3 HHHOH 4-F 4-OCF 3 1 CH 3 HHHO 4-F 4-F 4-Cl 1 CH 3 HHHO 3-Cl 4- F 4-CF 3 1 CH 3 HHHO 3-Br 4-F 4-OCF 3 1 CH 3 HHHO 3-CF 3 4-F 4-Cl 1 CH 3 HHHO 3-OCF 3 4-F 4-CF 3 1 CH 3 HHHO 3-OCHF 2 4-F 4-OCF 3 1 CH 3 HHHO 4-OCHF 2 4-F 4-Cl 1 CH 3 HHHO 3-F 4-Cl 4-CF 3 1 CH 3 HHHO 3-F 4- Br 4-OCF 3 1 CH 3 HHHO 3-F 4-CF 3 4-Cl 1 CH 3 HHHO 3-F 4-OSO 2 CF 3 4-CF 3 1 CH 3 HHHO 3-F 4-CN 4-OCF 3 1 CH 3 HHHO 3-F 3,4 -F 2 4-Cl ──────────────────────── ──────────

【００９８】[0098]

【表６４】 ─────────────────────────────────── k R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 1 CH3 H H H O 3-CF3 4-CN 4-CF3 1 CH2CH3 H H H O 3-F 4-F 4-Cl 1 CH2CH2CH3 H H H O 3-F 4-F 4-Br 1 CH2CH2CH2CH3 H H H O 3-F 4-F 4-CF3 1 CH(CH3)2 H H H O 3-F 4-F 4-OCF3 1 C(CH3)3 H H H O 3-F 4-F 4-OCHF2 1 CH2CH=CH2 H H H O 3-F 4-F 4-OCF2Br 1 CH2Ｃ≡CH H H H O 3-F 4-F 4-OCF2CHF2 1 CH2OCH3 H H H O 3-F 4-F 4-OSO2CF3 1 CH2OCH2CH3 H H H O H 4-F 4-OCF3 1 CH2CH2OCH3 H H H O 4-F 4-F 4-Cl 1 CHF2 H H H O 3-Cl 4-F 4-CF3 1 CBrF2 H H H O 3-Br 4-F 4-OCF3 1 CF3 H H H O 3-CF3 4-F 4-Cl 1 COCH3 H H H O 3-OCF3 4-F 4-CF3 1 COCF3 H H H O 3-OCHF2 4-F 4-OCF3 1 CO2CH3 H H H O 4-OCHF2 4-F 4-Cl 1 CH2C6H5 H H H O 3-F 4-Cl 4-CF3 1 SC6H5 H H H O 3-F 4-Br 4-OCF3 1 SCCl3 H H H O 3-F 4-CF3 4-Cl 1 SCO2CH2CH3 H H H O 3-F 4-OSO2CF3 4-CF3 1 S(C6H4-2-NO2) H H H O 3-F 4-CN 4-OCF3 1 SN(CH2CH2CH2CH3)2 H H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 64] ─────────────────────────────────── k R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 1 CH 3 HHHO 3-CF 3 4-CN 4-CF 3 1 CH 2 CH 3 HHHO 3-F 4-F 4-Cl 1 CH 2 CH 2 CH 3 HHHO 3-F 4-F 4-Br 1 CH 2 CH 2 CH 2 CH 3 HHHO 3-F 4 -F 4-CF 3 1 CH (CH 3 ) 2 HHHO 3-F 4-F 4-OCF 3 1 C (CH 3 ) 3 HHHO 3-F 4-F 4-OCHF 2 1 CH 2 CH = CH 2 HHHO 3-F 4-F 4-OCF 2 Br 1 CH 2 C ≡ CH HHHO 3-F 4-F 4-OCF 2 CHF 2 1 CH 2 OCH 3 HHHO 3-F 4-F 4-OSO 2 CF 3 1 CH 2 OCH 2 CH 3 HHHOH 4-F 4-OCF 3 1 CH 2 CH 2 OCH 3 HHHO 4-F 4-F 4-Cl 1 CHF 2 HHHO 3-Cl 4-F 4-CF 3 1 CBrF 2 HHHO 3- Br 4-F 4-OCF 3 1 CF 3 HHHO 3-CF 3 4-F 4-Cl 1 COCH 3 HHHO 3-OCF 3 4-F 4-CF 3 1 COCF 3 HHHO 3-OCHF 2 4-F 4- OCF 3 1 CO 2 CH 3 HHHO 4-OCHF 2 4-F 4-Cl 1 CH 2 C 6 H 5 HHHO 3-F 4-Cl 4-CF 3 1 SC 6 H 5 HHHO 3-F 4-Br 4- OCF 3 1 SCCl 3 HHHO 3-F 4-CF 3 4-Cl 1 SCO 2 CH 2 CH 3 HHHO 3-F 4-OSO 2 CF 3 4-CF 3 1 S (C 6 H 4 -2-NO 2 ) HHHO 3-F 4-CN 4-OCF 3 1 SN (CH 2 CH 2 CH 2 CH 3 ) 2 HHHO 3-F 3,4-F 2 4-Cl ── ──────────────────────────────────

【００９９】[0099]

【表６５】 ─────────────────────────────────── k R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 1 SN(CH3)CO2CH2CH3 H H H O 3-CF3 4-CN 4-CF3 2 H H H H O 3-F 4-F 4-Cl 2 H H H H O 3-F 4-F 4-Br 2 H H H H O 3-F 4-F 4-CF3 2 H H H H O 3-F 4-F 4-OCF3 2 H H H H O 3-F 4-F 4-OCHF2 2 H H H H O 3-F 4-F 4-OCF2Br 2 H H H H O 3-F 4-F 4-OCF2CHF2 2 H H H H O 3-F 4-F 4-OSO2CF3 2 H H H H O H 4-F 4-OCF3 2 H H H H O 4-F 4-F 4-Cl 2 H H H H O 3-Cl 4-F 4-CF3 2 H H H H O 3-Br 4-F 4-OCF3 2 H H H H O 3-CF3 4-F 4-Cl 2 H H H H O 3-OCF3 4-F 4-CF3 2 H H H H O 3-OCHF2 4-F 4-OCF3 2 H H H H O 4-OCHF2 4-F 4-Cl 2 H H H H O 3-F 4-Cl 4-CF3 2 H H H H O 3-F 4-Br 4-OCF3 2 H H H H O 3-F 4-CF3 4-Cl 2 H H H H O 3-F 4-OSO2CF3 4-CF3 2 H H H H O 3-F 4-CN 4-OCF3 2 H H H H O 3-F 3,4-F2 4-Cl ───────────────────────────────────[Table 65] ─────────────────────────────────── k R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 1 SN (CH 3 ) CO 2 CH 2 CH 3 HHHO 3-CF 3 4-CN 4-CF 3 2 HHHHO 3-F 4-F 4-Cl 2 HHHHO 3-F 4-F 4-Br 2 HHHHO 3-F 4-F 4-CF 3 2 HHHHO 3 -F 4-F 4-OCF 3 2 HHHHO 3-F 4-F 4-OCHF 2 2 HHHHO 3-F 4-F 4-OCF 2 Br 2 HHHHO 3-F 4-F 4-OCF 2 CHF 2 2 HHHHO 3-F 4-F 4-OSO 2 CF 3 2 HHHHOH 4-F 4-OCF 3 2 HHHHO 4-F 4-F 4-Cl 2 HHHHO 3-Cl 4-F 4-CF 3 2 HHHHO 3-Br 4 -F 4-OCF 3 2 HHHHO 3-CF 3 4-F 4-Cl 2 HHHHO 3-OCF 3 4-F 4-CF 3 2 HHHHO 3-OCHF 2 4-F 4-OCF 3 2 HHHHO 4-OCHF 2 4-F 4-Cl 2 HHHHO 3-F 4-Cl 4-CF 3 2 HHHHO 3-F 4-Br 4-OCF 3 2 HHHHO 3-F 4-CF 3 4-Cl 2 HHHHO 3-F 4-OSO 2 CF 3 4-CF 3 2 HHHHO 3-F 4-CN 4-OCF 3 2 HHHHO 3-F 3,4-F 2 4-Cl ────────────────── ──────────────────

【０１００】[0100]

【表６６】 ─────────────────────────────────── k R1 R2 R3 R4 W Xl Ym Zn ─────────────────────────────────── 2 H H H H O 3-CF3 4-CN 4-CF3 ───────────────────────────────────[Table 66] ─────────────────────────────────── k R 1 R 2 R 3 R 4 WX l Y m Z n ─────────────────────────────────── 2 HHHHO 3-CF 3 4-CN 4- CF 3 ───────────────────────────────────

【０１０１】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穀害虫、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, mosquitosus alba, Echinochloea lucidum, Kobnomeiga, and Koga moth, spider mites, mandarin mites, kanzawa mites, etc.
Flea, sanitary pests such as lice, weevil, stag beetle, stored grain pests such as striped moth, house pests such as termites, livestock pests such as mites, fleas, lice, indoor dust mites such as mites, leopard mites, tick mites, Examples include molluscs such as slugs and snails. 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.

【０１０２】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セミカルバゾン誘導体であ
り、代表的な製造法を以下に具体的に説明する。Next, a method for producing the compound of the present invention will be described. The compound of the present invention is a novel semicarbazone derivative, and a typical production method will be specifically described below.

【０１０３】各方法（Ａ法〜Ｄ法）において、Ｗ、Ｘ、
Ｙ、Ｚ、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 、ｋ、ｌ、ｍ及びｎは
前記と同じ意味を示し、Ｌ1 は、塩素原子、臭素原子、
ヨウ素原子、アルキルスルホネート基またはアリールス
ルホネート基のような良好な脱離基を示す。In each method (method A to method D), W, X,
Y, Z, R 1 , R 2 , R 3 , R 4 , k, l, m and n have the same meanings as described above, L 1 is a chlorine atom, a bromine atom,
It shows a good leaving group such as an iodine atom, an alkyl sulfonate group or an aryl sulfonate group.

【０１０４】Ａ法Method A

【０１０５】[0105]

【化６】 [Chemical 6]

【０１０６】化合物［II］と五塩化リンとを不活性な溶
媒中または溶媒なしで反応させるか、または化合物［I
I］をトリフェニルホスフィン及び四塩化炭素と反応さ
せることにより化合物［III］が得られる。つづいて化
合物［III］と化合物［IV］を塩基の存在下または不存
在下、不活性な溶媒中で反応させることにより本発明化
合物［Ｖ］（化合物［Ｉ］においてＲ2 が水素原子）が
得られる。さらに本発明化合物［Ｖ］と化合物［VI］を
塩基の存在下、不活性ば溶媒中で反応させることにより
本発明化合物［Ｉ］を得ることができる。Compound [II] is reacted with phosphorus pentachloride in an inert solvent or without a solvent, or compound [I]
Compound [III] is obtained by reacting I] with triphenylphosphine and carbon tetrachloride. Then, the compound [III] and the compound [IV] are reacted in the presence or absence of a base in an inert solvent to give the compound [V] of the present invention (R 2 in the compound [I] is a hydrogen atom). can get. Furthermore, the compound [I] of the present invention can be obtained by reacting the compound [V] of the present invention with the compound [VI] in the presence of a base and in an inert solvent.

【０１０７】工程１において五塩化リンを用いる場合の
溶媒としてはベンゼン、トルエン等の芳香族炭化水素
類、四塩化炭素、１，１，２−トリクロロエタン等のハ
ロゲン化炭化水素類が挙げられる。一般的には無溶媒で
少し過剰の五塩化リン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を設
定できるが、６０℃から還流温度で行うのが好ましい。
トリフェニルホスフィン及び四塩化炭素を用いる場合は
当モルから少過剰のトリフェニルホスフィンと大過剰の
四塩化炭素を用いて、反応混合物の還流温度で行うのが
好ましい。Examples of the solvent when phosphorus pentachloride is used in step 1 include aromatic hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as carbon tetrachloride and 1,1,2-trichloroethane. Generally, it is preferred to use a slight excess of phosphorus pentachloride without solvent. The reaction temperature can be set to any temperature from 0 ° C to the reflux temperature of the reaction mixture, but is preferably 60 ° C to the reflux temperature.
When triphenylphosphine and carbon tetrachloride are used, it is preferable to use equimolar to small excess of triphenylphosphine and large excess of carbon tetrachloride at the reflux temperature of the reaction mixture.

【０１０８】工程２で用いられる塩基としては、ナトリ
ウムエトキシド、カリウムターシャリーブトキシドのよ
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、炭酸水素ナトリウム等のアルカリ
金属炭酸塩、水素化ナトリウム、水素化カリウム等のア
ルカリ金属水素化物、トリエチルアミン、ピリジン等の
有機塩基等が挙げられる。用いられる溶媒としては、反
応の進行を阻害しないものであれば良く、例えばメタノ
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、１，
２−ジメトキシエタン、テトラヒドロフラン、１，４−
ジオキサン等のエーテル類、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および水等が挙げら
れる。これらの不活性溶媒は単独で使用してもよく、ま
た、混合して使用することもできる。一般的には塩基と
して、トリエチルアミン、ピリジン等の有機塩基を用
い、溶媒としてベンゼン、トルエン等の芳香族炭化水素
類またはテトラヒドロフラン、ジエチルエーテル等のエ
ーテル類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
とができるが、０℃から５０℃までで行うのが好まし
い。As the base used in the step 2, alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, sodium hydroxide,
Alkali metal hydroxides such as potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as triethylamine and pyridine, etc. Can be mentioned. Any solvent may be used as long as it does not inhibit the progress of the reaction. For example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,
2-dimethoxyethane, tetrahydrofuran, 1,4-
Ethers such as dioxane, dichloromethane, 1,2-
Examples thereof include halogenated hydrocarbons such as dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an organic base such as triethylamine or pyridine as the base, and an aromatic hydrocarbon such as benzene or toluene or an ether such as tetrahydrofuran or diethyl ether as the solvent. The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 50 ° C.

【０１０９】工程３で用いられる塩基としては、ナトリ
ウムエトキシド、カリウムターシャリーブトキシドのよ
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、炭酸水素ナトリウム等のアルカリ
金属炭酸塩、水素化ナトリウム、水素化カリウム等のア
ルカリ金属水素化物、トリエチルアミン、ピリジン等の
有機塩基等が挙げられる。用いられる溶媒としては、反
応の進行を阻害しないものであれば良く、例えばメタノ
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、１，
２−ジメトキシエタン、テトラヒドロフラン、１，４−
ジオキサン等のエーテル類、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および水等が挙げら
れる。これらの不活性溶媒は単独で使用してもよく、ま
た、混合して使用することもできる。一般的にはテトラ
ヒドロフランやジメチルホルムアミド等の極性溶媒中
で、塩基として水素化ナトリウム、水素化カリウム、カ
リウムターシャリーブトキシドまたは水酸化カリウムを
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
が、０℃から９０℃までで行なうのが好ましい。As the base used in the step 3, alkali metal alkoxides such as sodium ethoxide and potassium tert-butoxide, sodium hydroxide,
Alkali metal hydroxides such as potassium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, organic bases such as triethylamine and pyridine, etc. Can be mentioned. Any solvent may be used as long as it does not inhibit the progress of the reaction. For example, lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether, 1,
2-dimethoxyethane, tetrahydrofuran, 1,4-
Ethers such as dioxane, dichloromethane, 1,2-
Examples thereof include halogenated hydrocarbons such as dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use sodium hydride, potassium hydride, potassium tert-butoxide or potassium hydroxide as a base in a polar solvent such as tetrahydrofuran or dimethylformamide. The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 90 ° C.

【０１１０】Ｂ法Method B

【０１１１】[0111]

【化７】 [Chemical 7]

【０１１２】出発原料の化合物［II］は化合物［VII］
と化合物［VIII］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得られる。本法で用いられる塩基と
しては炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリ
ウム等のアルカリ金属炭酸塩、水素化ナトリウム、水素
化カリウム等のアルカリ金属水素化物、トリエチルアミ
ン、ピリジン等の有機塩基等が挙げられる。用いられる
溶媒としては、反応の進行を阻害しないものであれば良
く、例えばベンゼン、トルエン等の芳香族炭化水素類、
ジエチルエーテル、１，２−ジメトキシエタン、テトラ
ヒドロフラン、１，４−ジオキサン等のエーテル類、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
シドおよび水等が挙げられる。これらの不活性溶媒は単
独で使用してもよく、また、混合して使用することもで
きる。一般的には塩基として、トリエチルアミン、ピリ
ジン等の有機塩基を用い、溶媒としてベンゼン、トルエ
ン等の芳香族炭化水素類またはテトラヒドロフラン、ジ
エチルエーテル等のエーテル類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が、０℃から５０℃ま
でで行うのが好ましい。Compound [II] as the starting material is compound [VII]
And compound [VIII] in the presence of a base in an inert solvent. Examples of the base used in this method include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium hydrogen carbonate, alkali metal hydrides such as sodium hydride and potassium hydride, and organic bases such as triethylamine and pyridine. The solvent used may be one that does not hinder the progress of the reaction, for example, aromatic hydrocarbons such as benzene and toluene,
Ethers such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 1,4-dioxane, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethyl Examples include sulfoxide and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an organic base such as triethylamine or pyridine as the base, and an aromatic hydrocarbon such as benzene or toluene or an ether such as tetrahydrofuran or diethyl ether as the solvent.
The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to 50 ° C.

【０１１３】Ｃ法Method C

【０１１４】[0114]

【化８】 [Chemical 8]

【０１１５】本法は、Ｒ3＝Ｒ4＝水素原子である場合の
出発原料（化合物［IV］のＲ3＝Ｒ4＝水素原子）の合成
法である。化合物［IX］と化合物［Ｘ］を触媒の存在下
または不存在下、不活性な溶媒中で反応させることによ
り化合物［XI］が得られる。本反応において用いられる
触媒としては、トリエチレンジアミン、ジアザビシクロ
ウンデセン等の有機塩基等が挙げられる。触媒の使用量
は化合物［Ｘ］に対して０．００１重量％から１０重量
％までの任意の量を設定できるが、０．１重量％から１
重量％が好ましい。溶媒としては反応の進行を阻害しな
いものであれば良く、例えば、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
ラン等のエーテル類、ジクロロメタン、クロロホルム等
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
チルスルホキシドおよび水等が挙げられる。これらの不
活性溶媒は単独で使用してもよく、また、混合して使用
することもできる。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
が、０℃から５０℃で行うのが好ましい。この反応にお
いて反応物質のモル比には特に制限はないが化合物［X
I］を収率よく得るためには、化合物［Ｘ］に対して化
合物［IX］を少し過剰に用いるのが好ましい。This method is a method for synthesizing a starting material (R 3 = R 4 = hydrogen atom of compound [IV]) when R 3 = R 4 = hydrogen atom. Compound [XI] is obtained by reacting compound [IX] with compound [X] in the presence or absence of a catalyst in an inert solvent. Examples of the catalyst used in this reaction include organic bases such as triethylenediamine and diazabicycloundecene. The amount of the catalyst used can be set to any amount from 0.001% by weight to 10% by weight with respect to the compound [X], but 0.1% by weight to 1% by weight.
Weight percent is preferred. Any solvent may be used as long as it does not inhibit the progress of the reaction, and examples thereof include aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and chloroform, and dimethylformamide. , Amides such as dimethylacetamide, acetonitrile, dimethylsulfoxide, water and the like. These inert solvents may be used alone or in a mixture. The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, but is preferably 0 ° C. to 50 ° C. In this reaction, the molar ratio of the reactants is not particularly limited, but the compound [X
In order to obtain I] in good yield, it is preferable to use the compound [IX] in a slight excess with respect to the compound [X].

【０１１６】Ｄ法Method D

【０１１７】[0117]

【化９】 [Chemical 9]

【０１１８】本法は、Ｃ法の別法で、Ｒ3＝Ｒ4＝水素原
子である場合の出発原料（化合物［IV］のＲ3＝Ｒ4＝水
素原子）の合成法である。化合物［XII］と化合物
［Ｘ］を触媒の存在下または不存在下、不活性な溶媒中
で反応させることにより化合物［XIII］が得られる。本
反応において用いられる触媒、溶媒及び温度等の反応条
件はＣ法と同じである。本法においては、当モルの化合
物［XII］と化合物［Ｘ］を用いて収率よく化合物［XII
I］を得ることができるのが特徴である。工程２におい
て、化合物［XIII］を酸の存在下、不活性な溶媒中で反
応させることにより、化合物［XI］を得ることができ
る。用いられる酸としては、塩酸、硫酸等の無機酸、パ
ラトルエンスルホン酸、トリフルオロ酢酸等の有機酸等
が挙げられる。溶媒としては、反応の進行を阻害しない
ものであれば良く、例えば、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等の
エーテル類、ジクロロメタン、四塩化炭素等のハロゲン
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、酢酸および水等が挙げられる。これらの不活性
溶媒は単独で使用してもよく、また、混合して使用する
こともできる。一般的には、メタノール、エタノール等
の低級アルコール中で過剰量の塩酸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が、０℃から反応
混合物の還流温度で行うのが好ましい。This method is an alternative to the method C and is a method for synthesizing a starting material (R 3 = R 4 = hydrogen atom of compound [IV]) when R 3 = R 4 = hydrogen atom. Compound [XIII] is obtained by reacting compound [XII] with compound [X] in the presence or absence of a catalyst in an inert solvent. The reaction conditions such as catalyst, solvent and temperature used in this reaction are the same as those in Method C. In this method, equimolar amounts of compound [XII] and compound [X] are used to yield compound [XII] in good yield.
The feature is that I] can be obtained. In step 2, compound [XIII] can be reacted in the presence of an acid in an inert solvent to give compound [XI]. Examples of the acid used include inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as paratoluenesulfonic acid and trifluoroacetic acid, and the like. Any solvent may be used as long as it does not hinder the progress of the reaction, and examples thereof include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, ethers such as diethyl ether and tetrahydrofuran, dichloromethane, and four. Examples thereof include halogenated hydrocarbons such as carbon chloride, amides such as dimethylformamide and dimethylacetamide, acetonitrile, dimethylsulfoxide, acetic acid and water. These inert solvents may be used alone or in a mixture. Generally, it is preferable to use an excess amount of hydrochloric acid in a lower alcohol such as methanol or ethanol. The reaction temperature can be set to any temperature from -60 ° C to the reflux temperature of the reaction mixture, but is preferably 0 ° C to the reflux temperature of the reaction mixture.

【０１１９】各方法において、各反応物質のモル比には
特に制限はないが、等モルまたはそれに近い比率で反応
を行なうのが有利である。In each method, the molar ratio of each reactant is not particularly limited, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close to it.

【０１２０】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。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.

【０１２１】本発明化合物を有害生物防除剤として施用
するにあたっては、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、ホワイトカーボン
等の固体担体あるいは水、アルコール類（イソプロパノ
ール、ブタノール、ベンジルアルコール、フルフリルア
ルコール等）、芳香族炭化水素類（トルエン、キシレン
等）、エーテル類（アニソール等）、ケトン類（シクロ
ヘキサノン、イソホロン等）、エステル類（酢酸ブチル
等）、酸アミド類（Ｎ−メチルピロリドン等）またはハ
ロゲン化炭化水素類（クロルベンゼン等）などの液体担
体と混用して適用することができ、所望により界面活性
剤、乳化剤、分散剤、浸透剤、展着剤、増粘剤、凍結防
止剤、固結防止剤、安定剤などを添加し、液剤、乳剤、
水和剤、ドライフロアブル剤、フロアブル剤、粉剤、粒
剤等任意の剤型にて実用に供することができる。When the compound of the present invention is applied as a pest control agent, generally, a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth, white carbon or water, alcohols (isopropanol, butanol, benzyl alcohol) is used. , Furfuryl alcohol etc.), aromatic hydrocarbons (toluene, xylene etc.), ethers (anisole etc.), ketones (cyclohexanone, isophorone etc.), esters (butyl acetate etc.), acid amides (N-methyl) (Pyrrolidone etc.) or halogenated hydrocarbons (chlorobenzene etc.) and the like can be mixed and applied, and if desired, a surfactant, an emulsifier, a dispersant, a penetrant, a spreading agent, a thickener, Antifreeze agents, anti-caking agents, stabilizers, etc. are added, and liquid agents, emulsions,
It can be put into practical use in any dosage form such as a wettable powder, a dry flowable agent, a flowable agent, a powder agent, and a granule.

【０１２２】また、本発明化合物は必要に応じて製剤時
または散布時に他種の除草剤、各種殺虫剤、殺ダニ剤、
殺線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土
壌改良剤などと混合施用しても良い。In addition, the compound of the present invention, if necessary, may be used as a herbicide of other species, various insecticides, acaricides at the time of formulation or spraying.
It may be mixed and applied with nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners and the like.

【０１２３】特に他の農薬あるいは植物ホルモンと混合
施用することにより、施用薬量の減少による低コスト
化、混合薬剤の相乗作用による殺虫スペクトラムの拡大
や、より高い有害生物防除効果が期待できる。この際、
同時に複数の公知農薬との組み合わせも可能である。本
発明化合物と混合使用する農薬の種類としては、例え
ば、ファーム・ケミカルズ・ハンドブック（Farm Chemi
cals Handbook）１９９３年版に記載されている化合物
などがある。Particularly, when mixed with other agricultural chemicals or plant hormones, it can be expected to reduce the cost by reducing the amount of the applied drug, to broaden the insecticidal spectrum due to the synergistic action of the mixed drugs, and to have a higher pest control effect. On this occasion,
It is also possible to combine a plurality of known pesticides at the same time. The types of pesticides used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm Chemi
cals Handbook) Compounds described in the 1993 edition.

【０１２４】本発明化合物の施用薬量は適用場面、施用
時期、施用方法、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（ha) 当たり０．００５
〜５０ｋｇ程度が適当である。The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crop, etc., but generally it is 0.005 per hectare (ha) as an active ingredient amount.
Approximately 50 kg is suitable.

【０１２５】次に具体的に本発明化合物を用いる場合の
製剤の配合例を示す。但し本発明の配合例は、これらの
みに限定されるものではない。なお、以下の配合例にお
いて「部」は重量部を意味する。[0125] Next, formulation examples of preparations using the compound of the present invention will be shown concretely. However, the compounding examples of the present invention are not limited to these. In the following formulation examples, "part" means part by weight.

【０１２６】〔水和剤〕 本発明化合物・・・・・・・ ５〜８０部 固体担体 ・・・・・・・１０〜８５部 界面活性剤 ・・・・・・・ １〜１０部 その他 ・・・・・・・ １〜５ 部 その他として、例えば固結防止剤などがあげられる。[Wettable powder] Compound of the present invention: 5 to 80 parts Solid carrier: 10 to 85 parts Surfactant: 1 to 10 parts ........ 1 to 5 parts Other examples include anti-caking agents.

【０１２７】〔乳 剤〕 本発明化合物・・・・・・・ １〜３０部 液体担体 ・・・・・・・３０〜９５部 界面活性剤 ・・・・・・・ ５〜１５部[Emulsion] Compound of the present invention: 1 to 30 parts Liquid carrier: 30 to 95 parts Surfactant: 5 to 15 parts

【０１２８】〔フロアブル剤〕 本発明化合物・・・・・・・ ５〜７０部 液体担体 ・・・・・・・１５〜６５部 界面活性剤 ・・・・・・・ ５〜１２部 その他 ・・・・・・・ ５〜３０部 その他として、例えば凍結防止剤、増粘剤等があげられ
る。[Flowable agent] Compound of the present invention: 5 to 70 parts Liquid carrier: 15 to 65 parts Surfactant: 5 to 12 parts Others: ..... 5 to 30 parts Other examples include antifreezing agents and thickeners.

【０１２９】〔粒状水和剤（ドライフロアブル剤）〕 本発明化合物・・・・・・・２０〜９０部 固体担体 ・・・・・・・１０〜６０部 界面活性剤 ・・・・・・・ １〜２０部[Granular wettable powder (dry flowable agent)] Compound of the present invention: 20 to 90 parts Solid carrier: 10 to 60 parts Surfactant:・ 1 to 20 copies

【０１３０】〔粒 剤〕 本発明化合物・・・・・・・0.1 〜１０部 固体担体 ・・・・・・・90〜99.99 部 その他 ・・・・・・・ １〜５ 部[Granule] Compound of the present invention: 0.1 to 10 parts Solid carrier: 90 to 99.99 parts Others: 1 to 5 parts

【０１３１】〔粉 剤〕 本発明化合物・・・・・・・0.01〜３０部 固体担体 ・・・・・・・67〜99.5 部 その他 ・・・・・・・ ０〜３ 部[Powder] Compound of the present invention: 0.01 to 30 parts Solid carrier: 67 to 99.5 parts Other :: 0 to 3 parts

【０１３２】[0132]

【実施例】【Example】

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 (Synthesis Examples, Formulation Examples, Test Examples) The present invention will be specifically described below with reference to Examples (Synthesis Examples, Formulation Examples, Test Examples).

【０１３３】〔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
とができるが、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 it can be produced or can be produced based on the synthetic examples shown below, the present invention is not limited to these compounds.

【０１３４】合成例１ Ｎ−（４−クロロフェニル）−４−クロロベンズアミド
−４−トリフルオロメトキシフェニルセミカルバゾン
（本発明化合物 Ｎｏ．１） Ｎ−（４−クロロフェニル）−４−クロロベンズアミド
１．０ｇ及び五塩化リン１．２ｇを徐々に加熱溶解し、
還流下で３時間撹拌した後、副生したオキシ塩化リンを
減圧下で留去した。残留物及びＮ−（４−トリフルオロ
メトキシフェニル）ヒドラジンカルボキサミド１．００
ｇをベンゼン２０ｍｌとテトラヒドロフラン２０ｍｌの
混合溶媒に溶解し、室温で撹拌下、トリエチルアミン
０．５０ｇを滴下し、さらに室温で３時間撹拌した。反
応混合物を氷水２００ｍｌ中に加えた後、酢酸エチル１
００ｍｌ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生成物
を２．０５ｇ得た。これを分取薄層クロマトグラフィー
で精製後、さらにイソプロピルエーテルから再結晶化し
て目的物を０．３８ｇ得た。1HNMR(CDCl3+DMSO d-6, TM
S, δ ppm): 6.50-7.65(12H, m), 8.08(1H,s), 8.41(1
H,s), 9.51(1H, s).Synthesis Example 1 N- (4-chlorophenyl) -4-chlorobenzamido-4-trifluoromethoxyphenylsemicarbazone
(Inventive Compound No. 1) 1.0 g of N- (4-chlorophenyl) -4-chlorobenzamide and 1.2 g of phosphorus pentachloride are gradually dissolved by heating,
After stirring under reflux for 3 hours, by-produced phosphorus oxychloride was distilled off under reduced pressure. Residue and N- (4-trifluoromethoxyphenyl) hydrazinecarboxamide 1.00
g was dissolved in a mixed solvent of 20 ml of benzene and 20 ml of tetrahydrofuran, 0.50 g of triethylamine was added dropwise with stirring at room temperature, and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was added to 200 ml of ice water, and ethyl acetate 1 was added.
00 ml was added for extraction. The organic layer was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.05 g of a crude product. This was purified by preparative thin layer chromatography and then recrystallized from isopropyl ether to obtain 0.38 g of the desired product. 1 HNMR (CDCl 3 + DMSO d-6, TM
S, δ ppm): 6.50-7.65 (12H, m), 8.08 (1H, s), 8.41 (1
H, s), 9.51 (1H, s).

【０１３５】参考例１ Ｎ−（４−クロロフェニル）−４−クロロベンズアミド ４−クロロアニリン３．３ｇとトリエチルアミン３．３
ｇをベンゼン５０ｍｌに溶解し、氷冷下で撹拌下、４−
クロロベンゾイルクロライド５．３ｇのベンゼン溶液２
０ｍｌを滴下した後、さらに室温で１時間撹拌した。反
応混合物を氷水２００ｍｌに加えた後、酢酸エチル２０
０ｍｌで抽出した。有機層を１規定塩酸、ついで飽和食
塩水で洗浄し、無水硫酸ナトリウムで乾燥後、減圧下で
溶媒を留去して、Ｎ−（４−クロロフェニル）−４−ク
ロロベンズアミドを６．３３ｇ得た。Reference Example 1 N- (4-chlorophenyl) -4-chlorobenzamide 3.3 g of 4-chloroaniline and 3.3 of triethylamine.
g was dissolved in 50 ml of benzene, and 4-
Chlorobenzoyl chloride 5.3 g benzene solution 2
After dropping 0 ml, the mixture was further stirred at room temperature for 1 hour. After adding the reaction mixture to 200 ml of ice water, ethyl acetate 20
Extracted with 0 ml. The organic layer was washed with 1N hydrochloric acid and then with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 6.33 g of N- (4-chlorophenyl) -4-chlorobenzamide. .

【０１３６】上記合成例に従って第２表に示す化合物を
合成した。The compounds shown in Table 2 were synthesized according to the above synthesis examples.

【０１３７】第 ２ 表Table 2

【０１３８】[0138]

【化１０】 [Chemical 10]

【０１３９】[0139]

【表６７】 ─────────────────────────────────── No. k R1 R2 R3 R4 W Xl Ym Zn 融点 ─────────────────────────────────── 1 0 H H H O 4-Cl 4-Cl 4-OCF3 206.5-208.0 2 1 H H H H O 4-Cl 4-Cl 4-OCF3 185.0-187.0 3 0 H H H O 3-Cl 4-F 4-OCF3 182.0-183.0 4 0 H H H O 3-Cl 4-CN 4-OCF3 198.0-200.0 5 0 H H H O 3-F 4-CN 4-OCF3 193.0-195.5 6 1 H H H H O 3-CF3 4-F 4-OCF3 166.0-167.0 7 0 H H H O 4-CF3 4-F 4-OCF3 183.0-185.5 8 1 H H H H O 3-CF3 4-F 4-OCF3 166.0-167.0 9 0 H H H O 3-CF3 4-CN 4-OCF3 210.0-212.5 10 0 H H H O 3-CF3 4-CF3 4-OCF3 162.0-163.0 11 0 H H H O 3-OCF3 4-CN 4-OCF3 199.5-202.5 ───────────────────────────────────[Table 67] ─────────────────────────────────── No. k R 1 R 2 R 3 R 4 WX l Y m Z n Melting point ─────────────────────────────────── 1 0 HHHO 4-Cl 4- Cl 4-OCF 3 206.5-208.0 2 1 HHHHO 4-Cl 4-Cl 4-OCF 3 185.0-187.0 3 0 HHHO 3-Cl 4-F 4-OCF 3 182.0-183.0 4 0 HHHO 3-Cl 4-CN 4 -OCF 3 198.0-200.0 5 0 HHHO 3-F 4-CN 4-OCF 3 193.0-195.5 6 1 HHHHO 3-CF 3 4-F 4-OCF 3 166.0-167.0 7 0 HHHO 4-CF 3 4-F 4 -OCF 3 183.0-185.5 8 1 HHHHO 3-CF 3 4-F 4-OCF 3 166.0-167.0 9 0 HHHO 3-CF 3 4-CN 4-OCF 3 210.0-212.5 10 0 HHHO 3-CF 3 4-CF 3 4-OCF 3 162.0-163.0 11 0 HHHO 3-OCF 3 4-CN 4-OCF 3 199.5-202.5 ────────────────────────── ──────────

【０１４０】〔製剤例〕次に、本発明化合物を有効成分
とする有害生物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, a formulation example of a pest controlling agent containing the compound of the present invention as an active ingredient is shown, but the present invention is not limited thereto. In the following formulation examples, "part" means part by weight.

【０１４１】〔製剤例１〕水和剤 本発明化合物 ・・・・・・・・・５０部 ジークライトＰＦＰ ・・・・・・・・・４３部 （カオリン系クレー：ジークライト工業（株）商品名） ソルポール 5050 ・・・・・・・・・ ２部 （アニオン性界面活性剤：東邦化学工業（株）商品名） ルノックス 1000 Ｃ ・・・・・・・・・ ３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（固結防止剤）・・・ ２部 （ホワイトカーボン：塩野義製薬（株）商品名） 以上を均一に混合粉砕して水和剤とする。[Formulation Example 1] Wettable powder Compound of the present invention: 50 parts Diklite PFP: 43 parts (Kaolin clay: Sikhlite Industry Co., Ltd.) Product name: Solpol 5050 ・ ・ ・ ・ ・ ・ ・ ・ 2 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) Lunox 1000 C ・ ・ ・ ・ ・ ・ 3 parts (Anionic interface Activator: Toho Chemical Industry Co., Ltd. product name) Carplex # 80 (anti-caking agent) ... 2 parts (white carbon: Shionogi Pharmaceutical Co., Ltd. product name) Use as an agent.

【０１４２】〔製剤例２〕乳 剤 本発明化合物 ・・・・・・・・・ ３部 キシレン ・・・・・・・・・７６部 イソホロン ・・・・・・・・・１５部 ソルポール3005Ｘ ・・・・・・・・・ ６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 2] Emulsion Compound of the present invention: 3 parts xylene: 76 parts Isophorone: 15 parts Solpol 3005X ..... 6 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above components are uniformly mixed to form an emulsion.

【０１４３】〔製剤例３〕フロアブル剤 本発明化合物 ・・・・・・・・・３５部 アグリゾールＳ−711 ・・・・・・・・・ ８部 （非イオン性界面活性剤：花王（株）商品名） ルノックス 1000 Ｃ ・・・・・・・・・ 0.5部 （アニオン性界面活性剤：東邦化学工業（株）商品名） １％ロドポール水 ・・・・・・・・・２０部 （増粘剤：ローン・プーラン社商品名） エチレングリコール（凍結防止剤）・・・・ ８部 水 ・・・・・・・・・28.5部 以上を均一に混合して、フロアブル剤とする。[Formulation Example 3] Flowable agent Compound of the present invention: 35 parts Agrisol S-711: 8 parts (Nonionic surfactant: Kao (stock) ) Brand name) Lunox 1000 C ・ ・ ・ ・ ・ ・ 0.5 parts (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) 1% Rhodopol water ・ ・ ・ ・ ・ ・ 20 parts ( Thickener: Trade name of Lorne Poulin Co., Ltd. Ethylene glycol (antifreeze) ... 8 parts Water ... 28.5 parts Mix the above uniformly to make a flowable agent.

【０１４４】〔製剤例４〕粒状水和剤（ドライフロアブ
ル剤） 本発明化合物 ・・・・・・・・・７５部 イソバンNo.1 ・・・・・・・・・１０部 （アニオン性界面活性剤：クラレイソプレンケミカル
（株）商品名） バニレックスＮ ・・・・・・・・・ ５部 （アニオン性界面活性剤：山陽国策パルプ（株）商品
名） カープレックス＃８０ ・・・・・・・・・１０部 （ホワイトカーボン：塩野義製薬（株）商品名） 以上を均一に混合微粉砕してドライフロアブル剤とす
る。[Formulation Example 4] Granular wettable powder (dry flowable agent) Compound of the present invention: 75 parts Isoban No. 1: 10 parts (anionic interface Activator: Trade name of Kuraray Isoprene Chemical Co., Ltd. Vanillex N ........ 5 parts (Anionic surfactant: Trade name of Sanyo Kokusaku Pulp Co., Ltd.) Carplex # 80 ... 10 parts (white carbon: trade name of Shionogi Seiyaku Co., Ltd.) The above components are uniformly mixed and pulverized to obtain a dry flowable agent.

【０１４５】〔製剤例５〕粒 剤 本発明化合物 ・・・・・・・・０．１部 ベントナイト ・・・・・・・５５．０部 タルク ・・・・・・・４４．９部 以上を均一に混合粉砕した後、少量の水を加えて攪拌混
合捏和し、押出式造粒機で造粒し、乾燥して粒剤にす
る。[Formulation Example 5] Granules Compound of the present invention: 0.1 part Bentonite: 55.0 parts Talc :: 44.9 parts After being uniformly mixed and pulverized, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion granulator, and dried to give granules.

【０１４６】〔製剤例６〕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 6 Powder Compound of the present invention: 3.0 parts Carplex # 80: 0.5 parts (White carbon: Shionogi & Co., Ltd. ) Product name) Clay ・ ・ ・ ・ ・ ・ 95 parts Diisopropyl phosphate ・ ・ ・ ・ ・ ・ ・ ・ 1.5 parts The above is uniformly mixed and pulverized to give a powder.

【０１４７】使用に際しては上記水和剤、乳剤、フロア
ブル剤、粒状水和剤は水で５０〜２００００倍に希釈し
て有効成分が１ヘクタール（ha) 当たり０．００５〜５
０ｋｇになるように散布する。In use, the wettable powder, emulsion, flowable powder and granular wettable powder are diluted 50 to 20000 times with water to prepare an active ingredient in an amount of 0.005 to 5 per hectare (ha).
Sprinkle so that it weighs 0 kg.

【０１４８】〔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 controlling agent will be specifically described in the following test examples.

【０１４９】試験例１ ハスモンヨ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濃度の薬液に調製し、この薬液中にカン
ランの葉を約10秒間浸漬し、風乾後シャーレに入れ、こ
の中にハスモンヨトウ２令幼虫をシャーレ当たり10頭を
放虫し、孔のあいた蓋をして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 Spodoptera litura A 5% emulsion of the compound of the present invention described in the specification (25% wettable powder depending on the compound was used as a test) was diluted with water containing a spreader to give 1000 ppm. Prepare a chemical solution of the concentration, immerse kanran leaves in this chemical solution for about 10 seconds, air-dry and put it in a petri dish, in which 10 second-infested larvae of Spodoptera litura are released per petri dish with a perforated lid. And stored in a constant temperature 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.

【０１５０】 死虫率（％）＝ (死虫数／放虫数）×１００Mortality rate (%) = (number of dead insects / number of released insects) × 100

【０１５１】その結果、以下の化合物が１００％の死虫
率を示した。 本発明化合物：Ｎｏ．３，４，５，６，９，１０，１
１．As a result, the following compounds showed 100% mortality. Inventive compound: No. 3, 4, 5, 6, 9, 10, 1
1.

【０１５２】試験例２ 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濃度の薬液に調製し、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 2 Insecticidal test against pearl oyster ladybird 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. Then, prepare a chemical solution with a concentration of 1000 ppm, soak the tomato leaves in this chemical solution for about 10 seconds, air-dry and place in a petri dish.
Ten of the insects were released, covered and placed in a thermostatic chamber at 25 ° C, and the mortality rate after 6 days was calculated from the following formula. The test is 2
It was done in a ward system.

【０１５３】 死虫率（％）＝ (死虫数／放虫数）×１００Mortality rate (%) = (number of dead insects / number of released insects) × 100

【０１５４】その結果、以下の化合物が１００％の死虫
率を示した。 本発明化合物：Ｎｏ．１，２，３，４，５，６，８，
９，１０，１１．As a result, the following compounds showed 100% mortality. Inventive compound: No. 1, 2, 3, 4, 5, 6, 8,
9, 10, 11.

【０１５５】[0155]

【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、かつホ乳
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 spider 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.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 317/38 7419−4Ｈ 317/44 7419−4Ｈ 323/31 7419−4Ｈ 323/62 7419−4Ｈ 337/08 7106−4Ｈ Ｃ０７Ｄ 317/46 319/18 319/20 (72)発明者 沼田 昭 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 小倉 友幸 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 三宅 敏郎 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 藤田 明彦 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 三森 紀彦 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 瀧井 新自 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. 6 Identification code Office reference number FI Technical display location C07C 317/38 7419-4H 317/44 7419-4H 323/31 7419-4H 323/62 7419-4H 337/08 7106-4H C07D 317/46 319/18 319/20 (72) Inventor Akira Numata 1 722 Tsuboi-cho, Funabashi City, Chiba Prefecture, Central Research Laboratory, Nissan Chemical Industries, Ltd. (72) Tomoyuki Ogura Funabashi, Chiba Prefecture 1 722, Tsuboi-cho, Tsuboi-shi, Nissan Central Chemical Research Institute (72) Inventor Toshiro Miyake 1470 Shiraoka, Shiraoka-cho, Minami Saitama-gun, Saitama Prefecture Bioscience Research Institute, Nissan Chemical Industries, Ltd. (72) Akihiko Fujita Minami-Saitama-gun, Saitama Prefecture 1470 Shiraoka, Shiraoka-cho Nissan Chemical Industry Co., Ltd., Institute of Biological Sciences (72) Inventor Norihiko Mimori 1470, Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Co., Ltd. Company Biological Sciences in the Institute (72) inventor Takii new self Saitama Prefecture Minami-Saitama District Shiraoka-cho Oaza Shiraoka 1470 Nissan Chemical Industry Co., Ltd. Biological Sciences in the Institute

Claims (4)

【特許請求の範囲】[Claims] 【請求項１】 一般式［Ｉ］ 【化１】 〔式中、Ｗは酸素原子またはイオウ原子を示し、 Ｘ、Ｙ、Ｚは各々独立してハロゲン原子、水酸基、シア
ノ基、ニトロ基、ＳＣＮ基、トリメチルシリル基、
Ｒ9 、ＯＲ9、Ｓ（Ｏ）pＲ9基、ＯＳ（Ｏ）2Ｒ9基、Ｏ
Ｃ（Ｏ）Ｒ9基、Ｃ（Ｏ）Ｒ9基、ＣＯ2Ｒ9基、Ｃ（Ｏ）
Ｎ（Ｒ9）Ｒ10基、ＳＯ2Ｎ（Ｒ9）Ｒ10基、ＮＨＣ
（Ｏ）Ｒ9基、Ｎ（Ｒ9）Ｒ10基、隣あった炭素原子間で
形成する−ＣＨ＝ＣＨ−ＣＨ＝ＣＨ−基、−ＯＣＨ2Ｏ
−基、−ＯＣＨ2ＣＨ2Ｏ−基、−ＯＣＦ2Ｏ−基、−Ｏ
ＣＦ2ＣＦ2Ｏ−基または−ＯＣＦ2ＣＦ2−基を示し、 Ｒ1は水素原子、Ｒ5、Ｒ5によって置換されていてもよ
いＣ1〜Ｃ6アルキル基または（Ｒ5）qによって置換され
ていてもよいフェニル基を示し、 Ｒ2、Ｒ3、Ｒ4は各々独立して水素原子、Ｃ1〜Ｃ6アル
キル基、Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6アルキニル
基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ2〜Ｃ6アルコキシアル
キル基、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、Ｃ2〜Ｃ6ハロアルキルカルボニル
基、Ｃ1〜Ｃ6アルキルチオ基、Ｃ1〜Ｃ6ハロアルキルチ
オ基、Ｒ6ＯＣ（Ｏ）Ｎ（Ｒ7）Ｓ−基、Ｒ7（Ｒ8）ＮＳ
−基または（Ｒ5）qによって置換されていてもよいベン
ジル基を示し、 Ｒ5はハロゲン原子、水酸基、シアノ基、ニトロ基、Ｃ1
〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6
アルコキシ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6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アルコキシカルボニル基、アミノ基また
はジＣ1〜Ｃ6アルキルアミノ基を示し、 Ｒ6、Ｒ7、Ｒ8は各々独立してＣ1〜Ｃ6アルキル基、
（Ｒ5）qによって置換されていてもよいフェニル基また
は（Ｒ5）qによって置換されていてもよいベンジル基を
示し、 Ｒ9はＣ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハロアルキル基、
Ｃ2〜Ｃ6アルケニル基、Ｃ2〜Ｃ6ハロアルケニル基、Ｃ
2〜Ｃ6アルキニル基、Ｃ2〜Ｃ6ハロアルキニル基、Ｃ3
〜Ｃ6シクロアルキル基、Ｃ3〜Ｃ6ハロシクロアルキル
基、Ｃ4〜Ｃ7シクロアルキルアルキル基、Ｃ2〜Ｃ6アル
コキシアルキル基、Ｃ2〜Ｃ6アルキルチオアルキル基、
Ｃ2〜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、（Ｒ5）qによって置換されていてもよ
いフェニル基、（Ｒ5）qによって置換されていてもよい
ベンジル基または（Ｒ5）rによって置換されていてもよ
いピリジル基を示し、 Ｒ10は水素原子またはＣ1〜Ｃ6アルキル基を示し、 ｋは０〜２の整数を示し、 ｌは０〜５の整数（ただし、ｌが２〜５の場合Ｘは同一
であっても異なっていてもよい）を示し、 ｍは０〜５の整数（ただし、ｍが２〜５の場合Ｙは同一
であっても異なっていてもよい）を示し、 ｎは１〜５の整数（ただし、ｎが２〜５の場合Ｚは同一
であっても異なっていてもよい）を示し、 ｐは０〜２の整数を示し、 ｑは０〜５の整数（ただし、ｑが２〜５の場合Ｒ5は同
一であっても異なっていてもよい）を示し、 ｒは０〜４の整数（ただし、ｒが２〜４の場合Ｒ5は同
一であっても異なっていてもよい）を示す。〕で表わさ
れるセミカルバゾン化合物。1. A compound represented by the general formula [I]: [In the formula, W represents an oxygen atom or a sulfur atom, and X, Y, and Z are each independently a halogen atom, a hydroxyl group, a cyano group, a nitro group, an SCN group, a trimethylsilyl group,
R 9 , OR 9 , S (O) p R 9 group, OS (O) 2 R 9 group, O
C (O) R 9 group, C (O) R 9 group, CO 2 R 9 group, C (O)
N (R 9 ) R 10 group, SO 2 N (R 9 ) R 10 group, NHC
(O) R 9 group, N (R 9 ) R 10 group, —CH═CH—CH═CH— group formed between adjacent carbon atoms, —OCH 2 O
- group, -OCH 2 CH 2 O- group, -OCF 2 O-groups, -O
CF 2 CF 2 O- group or -OCF 2 CF 2 - represents a group, R 1 represents the hydrogen atom, R 5, which may be substituted by R 5 C 1 ~C 6 alkyl group or (R 5) q Represents a phenyl group which may be substituted, and R 2 , R 3 and R 4 are each independently a hydrogen 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 1 -C 6 haloalkyl group, a C 2 -C 6 alkoxyalkyl group, a C 2 -C 6 alkylcarbonyl group, a C 2 -C 6 alkoxycarbonyl group, a C 2 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, R 6 OC (O) N (R 7) S- group, R 7 (R 8) NS
A group or a benzyl group which may be substituted by (R 5 ) q , wherein R 5 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, C 1
To C 6 alkyl group, C 1 to C 6 haloalkyl group, C 1 to C 6
Alkoxy groups, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 haloalkylthio group, C 1 -C 6
An alkylsulfonyl group, a C 1 -C 6 haloalkylsulfonyl group, a C 2 -C 6 alkoxycarbonyl group, an amino group or a di C 1 -C 6 alkylamino group, wherein R 6 , R 7 and R 8 are each independently A C 1 -C 6 alkyl group,
(R 5) a phenyl group or optionally substituted by q (R 5) shows a benzyl group which may be substituted by q, R 9 is C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group ,
C 2 -C 6 alkenyl groups, C 2 -C 6 haloalkenyl groups, C
2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group, C 3
To C 6 cycloalkyl group, C 3 to C 6 halocycloalkyl group, C 4 to C 7 cycloalkylalkyl group, C 2 to C 6 alkoxyalkyl group, C 2 to C 6 alkylthioalkyl group,
C 2 -C 6 alkoxycarbonyl group, C 2 -C 6 cyanoalkyl radical, (R 5) a phenyl group optionally substituted by q, (R 5) Good benzyl group or optionally substituted by q ( R 5 ) represents a pyridyl group optionally substituted by r , R 10 represents a hydrogen atom or a C 1 -C 6 alkyl group, k represents an integer of 0 to 2, and l represents an integer of 0 to 5 ( Provided that when 1 is 2 to 5, X may be the same or different, and m is an integer of 0 to 5 (provided that when m is 2 to 5, Y is the same or different). N is an integer of 1 to 5 (however, when n is 2 to 5, Z may be the same or different), and p is an integer of 0 to 2. , q is an integer of 0 to 5 (provided that when R 5 of q is 2 to 5 be different even in the same Indicates have), r denotes 0 to 4 integer (provided that when r is 2 to 4 R 5 may be different even in the same). ] The semicarbazone compound represented by these. 【請求項２】 Ｗが酸素原子を示し、 Ｘが、ハロゲン原子、Ｃ1〜Ｃ6アルキル基、Ｃ1〜Ｃ6ハ
ロアルキル基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6ハ
ロアルキルチオ基またはＣ1〜Ｃ6ハロアルキルスルホニ
ルオキシ基を示し、 Ｙが、ハロゲン原子、シアノ基、ニトロ基、Ｃ1〜Ｃ6ア
ルキル基、Ｃ1〜Ｃ6ハロアルキル基、Ｃ1〜Ｃ6アルコキ
シ基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6アルキルチ
オ基、Ｃ1〜Ｃ6ハロアルキルチオ基、Ｃ1〜Ｃ6アルキル
スルホニル基、Ｃ1〜Ｃ6ハロアルキルスルホニル基、Ｃ
1〜Ｃ6ハロアルキルスルホニルオキシ基、隣あった炭素
原子間で形成する−ＯＣＦ2Ｏ−基または−ＯＣＦ2ＣＦ
2Ｏ−基を示し、 Ｚが、ハロゲン原子、シアノ基、ニトロ基、Ｃ1〜Ｃ6ハ
ロアルキル基、Ｃ1〜Ｃ6ハロアルコキシ基、Ｃ1〜Ｃ6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、Ｃ1〜Ｃ6ハロアルキルスルフ
ィニル基、Ｃ 1〜Ｃ6アルキルスルホニル基、Ｃ1〜Ｃ6ハ
ロアルキルスルホニル基、Ｃ1〜Ｃ6アルキルスルホニル
オキシ基、Ｃ1〜Ｃ6ハロアルキルスルホニルオキシ基、
隣あった炭素原子間で形成する−ＯＣＦ2Ｏ−基、−Ｏ
ＣＦ2ＣＦ2Ｏ−基または−ＯＣＦ2ＣＦ2−基を示し、 Ｒ1、Ｒ2、Ｒ3、Ｒ4が各々独立して水素原子またはＣ1
〜Ｃ6アルキル基を示し、 ｌおよびｍが各々独立して０〜２の整数を示し、ｎが１
〜３の整数を示す請求項１記載のセミカルバゾン化合
物。2. W is an oxygen atom, X is a halogen atom, C1~ C6Alkyl group, C1~ C6Ha
Lower alkyl group, C1~ C6Haloalkoxy group, C1~ C6Ha
Low alkylthio group or C1~ C6Haloalkylsulfoni
Is a halogen atom, cyano group, nitro group, C1~ C6A
Rukiru group, C1~ C6Haloalkyl group, C1~ C6Arcoki
Shi group, C1~ C6Haloalkoxy group, C1~ C6Alkylchi
O group, C1~ C6Haloalkylthio group, C1~ C6Alkyl
Sulfonyl group, C1~ C6Haloalkylsulfonyl group, C
1~ C6Haloalkylsulfonyloxy group, adjacent carbon
-OCF formed between atoms2O-group or -OCF2CF
2Represents an O- group, Z represents a halogen atom, a cyano group, a nitro group, C1~ C6Ha
Lower alkyl group, C1~ C6Haloalkoxy group, C1~ C6A
Rukiruthio group, C1~ C6Haloalkylthio group, C1~ C6
Alkylsulfinyl group, C1~ C6Haloalkyl sulf
Inyl group, C 1~ C6Alkylsulfonyl group, C1~ C6Ha
Roalkylsulfonyl group, C1~ C6Alkylsulfonyl
Oxy group, C1~ C6A haloalkylsulfonyloxy group,
-OCF formed between adjacent carbon atoms2O-group, -O
CF2CF2O-group or -OCF2CF2Represents a group, R1, R2, R3, RFourAre each independently a hydrogen atom or C1
~ C6Represents an alkyl group, l and m each independently represent an integer of 0 to 2, and n is 1
The semicarbazone compound according to claim 1, which represents an integer of 3 to 3.
Stuff. 【請求項３】 請求項１記載のセミカルバゾン化合物の
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。3. A pest control agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 1. 【請求項４】 請求項２記載のセミカルバゾン化合物の
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。4. A pest control agent containing, as an active ingredient, one or more of the semicarbazone compounds according to claim 2.
JP6240049A 1993-10-04 1994-10-04 Semiconductor compound and pest-controlling agent Pending JPH07165697A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP6240049A JPH07165697A (en) 1993-10-04 1994-10-04 Semiconductor compound and pest-controlling agent
AU20847/95A AU2084795A (en) 1994-10-04 1995-03-31 Benzamide semicarbazone derivatives and their use as pesticides
TW84103138A TW299314B (en) 1994-10-04 1995-03-31
PCT/JP1995/000623 WO1996010560A1 (en) 1994-10-04 1995-03-31 Benzamide semicarbazone derivatives and their use as pesticides
IL11322995A IL113229A0 (en) 1994-10-04 1995-04-03 Semicarbazone derivatives and pesticides

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP5-248133 1993-10-04
JP24813393 1993-10-04
JP6240049A JPH07165697A (en) 1993-10-04 1994-10-04 Semiconductor compound and pest-controlling agent

Publications (1)

Publication Number Publication Date
JPH07165697A true JPH07165697A (en) 1995-06-27

Family

ID=17053722

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6240049A Pending JPH07165697A (en) 1993-10-04 1994-10-04 Semiconductor compound and pest-controlling agent

Country Status (5)

Country Link
JP (1) JPH07165697A (en)
AU (1) AU2084795A (en)
IL (1) IL113229A0 (en)
TW (1) TW299314B (en)
WO (1) WO1996010560A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003976A1 (en) * 1995-07-21 1997-02-06 Nissan Chemical Industries, Ltd. Semicarbazone derivatives and pesticides

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ514001A (en) 1999-03-12 2001-09-28 Basf Ag Synergistic insecticidal compositions
ATE312511T1 (en) 1999-03-12 2005-12-15 SYNERGISTIC INSECTICIDE COMPOSITIONS
US7906128B2 (en) * 2002-10-21 2011-03-15 Wyeth Llc Use of neuronal sodium channel antagonists for the control of ectoparasites in homeothermic animals
TWI350728B (en) 2004-10-08 2011-10-21 Wyeth Corp Amitraz compositions
TWI368505B (en) 2005-05-24 2012-07-21 Wyeth Corp Versatile high load concentrate compositions for control of ecto-parasites

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462456B1 (en) * 1990-06-16 1996-05-08 Nihon Nohyaku Co., Ltd. Hydrazinecarboxamide derivatives, a process for production thereof, and uses thereof
EP0553284A1 (en) * 1990-10-05 1993-08-04 E.I. Du Pont De Nemours And Company Semicarbazone arthropodicides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003976A1 (en) * 1995-07-21 1997-02-06 Nissan Chemical Industries, Ltd. Semicarbazone derivatives and pesticides

Also Published As

Publication number Publication date
WO1996010560A1 (en) 1996-04-11
AU2084795A (en) 1996-04-26
TW299314B (en) 1997-03-01
IL113229A0 (en) 1995-07-31

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