TW200404764A - Novel haloalkylsulfonylaminobenzene derivatives and herbicide and process for using it - Google Patents

Novel haloalkylsulfonylaminobenzene derivatives and herbicide and process for using it Download PDF

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TW200404764A
TW200404764A TW92120316A TW92120316A TW200404764A TW 200404764 A TW200404764 A TW 200404764A TW 92120316 A TW92120316 A TW 92120316A TW 92120316 A TW92120316 A TW 92120316A TW 200404764 A TW200404764 A TW 200404764A
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halogenated
same
alkyl
different
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TW92120316A
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Chinese (zh)
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Tomokazu Hino
Takashi Shimaoka
Yuzo Miura
Koki Mametuka
Takahiro Kiyokawa
Sinji Murata
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Nihon Nohyaku Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The present invention provides the haloalkylsulfonyl-aminobenzene derivatives of formula (I) or its salt thereof, and herbicide, wherein the formula (I) is shown as: {wherein, R1 is halo(C1-C6)alkyl; R2 is H, (C1-C6)alkyl, (halo)(C1-C6)alkylcarbonyl, (substituted)phenlcarbonyl, (C1-C6)alkyloxycarbonyl, (substituted)phenyloxycarbonyl, (halo)(C1-C6)alkylsulfonyl, (substitued)phenylsulfonyl etc., Q is (substituted)heterocyclo which at least one of the constituted atoms is N and N links with A, A are substituted(C1-C6)alkylene, (substituted)(C2-C6)alkenyl or (C2-C6)alkynyl, G are O, S, N-R3, N-R4, N-R5R6, m is 0 or 1, X are 1-4 identical or different substitutents selected from the group consisting of H, halogen, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, cyclo(C3-C6)alkyl, (substituted)phenyl, (substituted)phenyloxy, (substituted)phenyl(C1-C6)alkylaminocarbonyl, OH, NH3, CN, NO2 etc., R3, R4, R5, R6 are H, alkylphenyl etc.}. The present invention comprises several advantages such as widespread application, effect continuity, excellent selection between crop and weed, especially is excellent to be used as herbicide on rice paddy.

Description

200404764 玖、發明說明： 【發明所屬之技術領域】 本發明係關於一種鹵烷磺醯苯胺衍生物或其鹽類、及 該化合物作爲有效成分之除草劑及其使用方法。 【先前技術】 從前，已知含有全氟烷磺醯胺基爲取代基之二苯*** 衍生物，係爲有用的除草劑或抗炎症劑（例如··參照專利 文獻1)，但於二苯***以外的骨架並未記載亦未暗示。 又，已知含有苯氧基、苯硫基、苯磺醯基等爲取代基之全 氟烷磺醯苯胺衍生物係爲有用的除草劑或抗炎症劑（例 如··參照專利文獻2)，含有三氟甲基磺醯胺基爲取代基 之脲衍生物係爲有用的除草劑（例如：參照專利文獻3)， 含有三氟甲基磺醯胺基之吡畊基爲有用的除草劑（例如： 參照專利文獻4)等中，並未記載或暗示本發明通式（1)所 表示的鹵烷磺醯苯胺衍生物，亦未記載關於含有本發明通 式（I)所表示的鹵烷磺醯苯胺衍生物在稻米及稻田雜草間 的選擇除草性。 又，在已知含有三氟甲基磺醯苯胺構造之雜環衍生物 係有用的除草劑（例如：參照專利文獻5)，三氟甲基磺醯 苯胺與雜環直接鍵結的骨架，並未記載或暗示關於本發明 通式（I)鹵烷磺醯苯胺與雜環係介於伸烷基等鍵結之骨架 化合物。在已知關於在第4位上含有2-嘧啶氧基之磺醯 苯肢衍生物及該化合物爲有效成分之除草劑（例如：參照 專利文獻6及7)，於稻米上沒有藥害及稻田適用性等記 200404764 載’與本發明通式（i)表不的鹵垸擴釀苯胺衍生物之骨架 係爲不同，亦沒有關於其骨架之特別記載或暗示。 再者’已知作爲除早劑有用在第2位置上含有嘻π定氧 基之磺醯苯胺衍生物（例如：參照專利文獻8、9及1 〇)， 含有第2位置之嘧啶基與第2位置之苯胺基鍵結的胺甲基 或亞胺基亞甲基之作爲除草劑有用的磺醯苯胺衍生物化合 物（例如：參照專利文獻1 1 )，在第2位置上具有嘧啶基、 進一步在第6位置上含有烷氧基烷基之三氟甲基磺醯苯胺 衍生物係爲對於哺乳動物毒性低且作爲稻田用除草劑有用 (參照專利文獻12)，在第2位置含有二甲氧基嘧啶基羥甲 基之二氟甲基磺醯苯胺衍生物係爲於稻米上含有選擇性之 除草劑（例如··參照專利文獻i 3 )，含有任一個二甲氧基嘧 啶基等係爲必須的構造特徵，但是並未記載或暗示關於本 發明通式（I)所表示的鹵烷磺醯苯胺衍生物，係鹵烷磺醯 苯胺基與雜環藉由烷基等鍵結之骨架化合物。又，作爲除 草劑之作用性亦爲不同。 【專利文獻1】 美國專利第3906024號說明書 【專利文獻2】 德國專利第2118190號說明書 【專利文獻3】 特開昭60-87254號公報 【專利文獻4】 美國專利第4345076號說明書 200404764 【專利文獻5】 歐洲專利第〇 〇 1 1 6 9 3號說明書 【專利文獻6】 特開平8 - 1 9 3 0 1 1號公報 【專利文獻7】 特開平8-29 1 1 46號公報 【專利文獻8】 國際公開第93/09099號小冊 【專利文獻9】 國際公開第96/41 799號小冊 【專利文獻1 0】 特開平2- 1 49567號公報 【專利文獻1 1】 特開平1卜60 5 62號公報 【專利文獻1 2】 特開2000-63360號公報 【專利文獻1 3】 特開2000-44546號公報 【發明內容】 【發明所欲解決之課題】 本發明者等對開發新穎除草劑，係爲對於含有磺醯苯 胺構造之衍生物合成與其生理活性重複銳意硏究的結果， 本發明通式（I)所表示的新穎鹵烷磺醯苯胺衍生物係爲文 獻中未曾記載的新規化合物，較先行技術中所揭示的化合 200404764 物具有顯著的除草效果，相對於含有磺醯脲系除草劑抵抗 性雜草等之難防除雜草之大多雜草種類，兼具廣泛適用 性、效果的持續性、優異的農作物-雜草間的選擇性等之 特性，因發現除草劑特別於作爲稻田除草劑爲有用’而完 成本發明者。 【解決課題之手段】 本發明關於含有鹵烷磺醯苯胺衍生物或其鹽類及其化 合物之除草劑及其使用方法，其包括通式（1):200404764 发明 Description of the invention: [Technical field to which the invention belongs] The present invention relates to a halosulfanilanilide derivative or a salt thereof, a herbicide using the compound as an active ingredient, and a method for using the same. [Prior art] In the past, diphenyl ether derivatives containing perfluoroalkanesulfonamide groups as substituents have been known to be useful herbicides or anti-inflammatory agents (for example, refer to Patent Document 1). A skeleton other than diethyl ether is neither described nor suggested. In addition, perfluoroalkanesulfonanilide derivatives containing substituents such as phenoxy, phenylthio, and benzenesulfonyl are known to be useful herbicides or anti-inflammatory agents (for example, see Patent Document 2), Urea derivatives containing a trifluoromethylsulfonamido group as a substituent are useful herbicides (for example, refer to Patent Document 3), and pyridoyl containing a trifluoromethylsulfonamido group is a useful herbicide ( For example, refer to Patent Document 4) etc., which does not describe or suggest the halosulfanilanilide derivative represented by the general formula (1) of the present invention, nor does it describe that the haloalkane represented by the general formula (I) of the present invention is contained. Selective herbicidal properties of sulfanilide derivatives among rice and paddy field weeds. In addition, a heterocyclic derivative containing a trifluoromethylsulfanilide structure is known to be a useful herbicide (for example, refer to Patent Document 5), a skeleton in which trifluoromethylsulfanilide is directly bonded to a heterocyclic ring, and There is no description or suggestion about a skeleton compound in which the halosulfonanilide and the heterocyclic system are bonded via an alkylene group, such as the general formula (I) of the present invention. It is known that the sulfenylbenzene derivative containing 2-pyrimidinyloxy group at the 4th position and the herbicide containing the compound as an active ingredient (for example, refer to Patent Documents 6 and 7) have no phytotoxicity or rice fields on rice. The applicability, etc., 200404764 is different from that of the halogenated aniline derivative aniline derivative represented by the general formula (i) of the present invention, and there is no special record or suggestion about its skeleton. Furthermore, it is known that it is useful as an early-elimination agent for a sulfoanilide derivative containing a pipidoxy group at the second position (for example, refer to Patent Documents 8, 9, and 10). An animethyl group or an imino methylene group bonded to an aniline group at a 2-position, and a sulfoanilide derivative compound useful as a herbicide (for example, refer to Patent Document 1 1), has a pyrimidinyl group at a second position, and further The trifluoromethylsulfanilide derivative containing an alkoxyalkyl group at the sixth position is low in toxicity to mammals and useful as a herbicide for rice fields (see Patent Document 12), and contains dimethoxy in the second position Difluoromethylsulfoanilide derivatives of pyrimidinyl hydroxymethyl are selective herbicides on rice (for example, see Patent Document i 3), and those containing any dimethoxypyrimidinyl group are Indispensable structural features, but there is no description or suggestion about the halosulfanilanilide derivative represented by the general formula (I) of the present invention, which is a skeleton compound in which the halosulfanilanilide group and a heterocyclic ring are bonded by an alkyl group or the like . In addition, the function as a herbicide is different. [Patent Document 1] US Patent No. 3906024 [Patent Document 2] German Patent No. 2118190 [Patent Document 3] Japanese Patent Laid-Open No. 60-87254 [Patent Document 4] US Patent No. 4345076 Specification 200404764 [Patent Document 5] European Patent No. 001 1 6 9 3 [Patent Document 6] Japanese Patent Application Laid-Open No. 8-1 9 3 0 1 [Patent Literature 7] Japanese Patent Application Laid-Open No. 8-29 1 1 46 [Patent Literature 8] ] International Publication No. 93/09099 [Patent Literature 9] International Publication No. 96/41 799 [Patent Literature 1 0] Japanese Patent Laid-Open No. 2- 1 49567 [Patent Literature 1 1] Japanese Patent Laid-Open No. 60 5 62 [Patent Document 1] JP 2000-63360 [Patent Document 1 3] JP 2000-44546 [Summary of the Invention] [Problems to be Solved by the Invention] The present inventors etc. The agent is a result of repeated deliberate research on the synthesis of a derivative containing a sulfoanilide structure and its physiological activity. The novel halosulfanilanilide derivative represented by the general formula (I) of the present invention is a new regulation not described in the literature. Compared with the compound 200404764 disclosed in the prior art, the compound has a significant herbicidal effect. Compared with most weed species that are difficult to control weeds, including sulfonylurea herbicide-resistant weeds, it has both broad applicability, The inventors have found that the herbicide is particularly useful as a paddy field herbicide because of its persistence of effects and excellent crop-weed selectivity. [Means for solving the problem] The present invention relates to a herbicide containing a halosulfanilanilide derivative or a salt thereof and a compound thereof, and a method for using the same, which includes the general formula (1):

R1_S〇2(R2、m g {式中，R1爲鹵化（C「C6)烷基’ R2爲氫原子、（CVC6)烷基、院氧基（C「C6)^ 基、（Ci-c6)烷基羰基、鹵化（CVC6)烷基鑛基、苯基鑛基、 含有1個以上之相同或不同均可以的選自γ(γ如後所述） 之取代基的苯基羰基、（Ci-CJ烷氧基羰基、苯氧基鑛基、 含有1個以上之相同或不同均可以的選自γ(γ如後所述） 之取代基的取代苯氧基羰基、（Ci-CJ燒基礦釀基、齒化 (Ci-CJ烷基磺醯基、苯基磺醯基或含有1個以上之相同 或不同均可以的選自γ(γ如後所述）之取代基的取代苯基 磺醯基， Q係爲構成原子至少1個爲氮原子，旦該氮原子與A 的鍵結部位爲可經取代之雜環’ ^ ^ A右'、、随白下列1個以上相同 A爲選自（CVC,)伸烷基、含有进自卜 200404764 或不同均可以的取代基之取代（C「C6)伸烷基、 嫌基··鹵素原子、經基、（Ci-C6)院氧基、（c^c^)院氧基 羰基或氰基，含有選自下列1個以上相同或不同均可以的 取代基之取代（C2-C6)伸細基或（CrC6)伸快基·瞻素原子、 經基、（(^-06)焼氧基、（Ci-C6)院氧基鑛基或氨基的， G爲氧原子、硫原子、N-R3(其中，R3爲氧原子、（CVC6) 院基、氰基、硝基、苯基（Cl·。6)院基、在環上含有1個 以上之相同或不同均可以的選自 Υ(γ如後所述）之取代基 的取代苯基（C^-C6)院基、本基或含有1個以上之相同或 不同均可以的選自Y(Y如後所述）之取代基的取代苯基）、 N-OR4(其中，R4爲氧原子、（CVC6)烷基、苯基（c「c6)^ 基或環上含有1個以上之相同或不同均可以的選自 γ(γ 如後所述）之取代基的取代苯基（C「C6)烷基）或N-NR5R6(其 中，R5及R6爲相同或不同均可以的氧原子、苯基或含J 個以上之相同或不同均可以的選自Y(Y如後所述）之取代 基的取代苯基），又，R5及R6同時爲（C3-C6)伸烷基）， m爲0或1之整數， X爲含選自相同或不同均可以的氧原子、鹵素原子、 (C1-C6)院基、（C2-C6)嫌基、（C2-C6)炔基、環（c3-c6)燒其 鹵化（cvc6)烷基、環鹵化（C3-C6)烷基、（Ci_c6)院氧基、 鹵化（C「c6)烷氧基、（c「c6)烷硫基、鹵化（Ci_c6：^硫基、 (c「c6)烷亞磺醯基、鹵化（CVC6)烷亞磺醯基' (C Γ 1 s)烷 磺醯基、（cvc0)烷磺醯基、鹵化（c「c6)烷磺醯基、苯基， 含有1個以上之相同或不同均可以的選自γ(γ如後所t -10- I ) 200404764 之取代基的取代苯基、苯氧基，含有1個以上之相同或不 同均可以的選自γ(γ如後所述）之取代基的取代苯氧基、 苯硫基’含有1個以上之相同或不同均可以的選自Υ(Υ 如後所述）之取代基的取代苯硫基、苯亞磺醯基，含有1 個以上之相同或不同均可以的選自γ(γ如後所述）之取代 基的苯亞磺醯基、苯磺醯基，含有1個以上之相同或不同 均可以的選自γ(γ如後所述）之取代基的苯磺醯基、（Ci-C6) 院基簾基、鹵化（(：1-0：6)烷基羰基、苯基羰基，含有1個 以上之相同或不同均可以的選自 γ(γ如後所述）之取代基 的苯基鑛基、（q-Cd烷氧基羰基、羧基、單（Ci-CJ烷胺 鑛基、相同或不同均可以的（Ci-c6)烷胺羰基、苯胺羰基、 環上含有1個以上之相同或不同均可以的選自γ(γ如後 所述）之取代基的取代苯胺羰基、苯基（Ci-c6)烷胺羰基； 在環上含有1個以上之相同或不同均可以的選自 Y(Y如 後所述）之取代基的取代苯基（Ci_c6)烷胺羰基、氧基、胺 基、氰基或硝基之1-4個取代基， γ爲含選自相同或不同均可以的鹵素原子、（Ci-C6)烷 基 ' (C2-C6)烯基、（c2-c6)炔基、環（c3-C6)烷基、鹵化（C「C6) ^ 環鹵化（C3-C6)院基、（CrC^)院氧基、鹵化d-C^) 丈完氧基、（cvc6)烷硫基、鹵化（(31-(：6)烷硫基、（(：146)烷 25擴酿基、鹵化（CVC6)烷亞磺醯基、（cvc6)烷磺醯基、 _化烷磺醯基、苯基，相同或不同均可以的鹵素 、（CVC,)烷基、（c2-c6)烯基、（c2-c6)炔基、環（c3-c6) 院基、鹵化（CrC,)烷基、環鹵化（C3-C6)烷基、（CVC6：^ -11- 200404764 氧基、鹵化（cvc6)院氧基、（cvC6)烷硫基、鹵化（CVC6) 院硫基、（eve,)院亞礦釀基、鹵化（Ci_c6)烷亞磺醯基、 (C「c6)烷磺醯基、鹵化烷磺醯基、（C^C6)烷基羰 基、鹵化（CVC6)院基鑛基、（cvC6)烷氧基羰基、羧基、 單（CVC6)烷胺羰基’含有相同或不同均可以的（Ci_C6)烷 胺羰基、羥基、胺基、氰基或硝基之i _ 5個取代基的取代 苯基、苯氧基；含選自相同或不同均可以的鹵素原子、 (CVC6)院基、（C2-C6)嫌基、（C2-C6)炔基、環（C3_C6)烷基、 鹵化（CVCJ烷基、環鹵化（c3-c6)烷基、（Ci_c6)烷氧基、 鹵化兀氧基、（CrCd院硫基、鹵化（c「c6)院硫基、 (Ci-Cd院亞磺醒基、鹵化（c「c6)烷亞磺醯基、（Ci-C6)烷 磺醯基、齒化（CVCs)烷磺醯基、（Ci-c6)烷基羰基、鹵化 (Ci-CJI兀基基、（CrCd烷氧基擬基、錢基、單（Ci_C6) 烷胺羰基，含選自相同或不同均可以的（Κ6)烷胺羰基、 羥基、胺基、氰基或硝基之1-5個取代基的取代苯氧基、 苯硫基；含選自相同或不同均可以的鹵素原子、（c「c 6) 烷基、（c2-c0)嫌基、（CVC6)炔基、環（CVC6)燒基、鹵化 (c「c6)烷基、環鹵化（(VC6)烷基、（CVC6)烷氧基、鹵化 (Ci C6)院氧基（C「c6)院硫基、鹵化（c「c6)院硫基、（c「c6) 烷亞磺醯基、鹵化（C1_( ^c6)烷亞磺醯基、（cvc6)烷磺醯基、R1_S〇2 (R2, mg {wherein, R1 is a halogenated (C "C6) alkyl 'R2 is a hydrogen atom, (CVC6) alkyl, oxy (C" C6) ^ group, (Ci-c6) alkane A carbonyl group, a halogenated (CVC6) alkyl group, a phenyl group, a phenylcarbonyl group containing one or more of the same or different substituents selected from γ (γ is described later), (Ci-CJ Alkoxycarbonyl group, phenoxy group, substituted phenoxycarbonyl group containing one or more of the same or different substituents selected from γ (γ is described later), (Ci-CJ calcined ores) (Ci-CJ alkylsulfonyl, phenylsulfonyl or substituted phenylsulfonyl containing one or more substituents selected from γ (γ as described below) which may be the same or different) Group, at least one of the Q atoms is a nitrogen atom, and once the bonding site between the nitrogen atom and A is a heterocyclic ring which can be substituted, ^ ^ A right, and one or more of the following A is selected from (CVC,) alkylene, substituted with a substituent that can be substituted from 200404764 or different (C "C6) alkylene, alkyl group, halogen atom, mesogen, (Ci-C6) oxy, (C ^ c ^) oxocarbonyl or cyano, Substituted from one or more of the following substituents which may be the same or different (C2-C6) slender group or (CrC6) squaryl group · Qinsu atom, meridian group, ((^ -06) fluorenyloxy group, (Ci-C6) oxo or amino, G is an oxygen atom, sulfur atom, N-R3 (where R3 is an oxygen atom, (CVC6) group, cyano, nitro, phenyl (Cl · . 6) a radical, a substituted phenyl (C ^ -C6) radical containing one or more of the same or different substituents selected from fluorene (γ as described below) on the ring, a radical or a radical containing One or more of the same or different substituted phenyl groups selected from the substituents of Y (Y is described later), N-OR4 (wherein R4 is an oxygen atom, (CVC6) alkyl group, phenyl group (c "C6) a substituted phenyl (C" C6) alkyl group containing at least one of the same or different substituents on γ group or ring, which may be the same or different, or N-NR5R6 (wherein R5 and R6 are the same or different oxygen atoms, phenyl groups, or substituted phenyl groups containing at least J of the same or different substituents selected from Y (Y is described later)), and R5 And R6 is (C3-C6) alkylene), m is 0 or 1 Integer, X is an oxygen atom, halogen atom, (C1-C6) group, (C2-C6) alkynyl group, (C2-C6) alkynyl group, ring (c3-c6) Its halogenated (cvc6) alkyl, cyclohalogenated (C3-C6) alkyl, (Ci_c6) alkyloxy, halogenated (C "c6) alkoxy, (c" c6) alkylthio, halogenated (Ci_c6: ^ sulfur (C "c6) alkylsulfinyl, halogenated (CVC6) alkylsulfinyl '(C Γ 1 s) alkylsulfinyl, (cvc0) alkylsulfinyl, halogenated (c" c6) alkylsulfonyl A fluorenyl group and a phenyl group containing one or more of the same or different substituents selected from the group consisting of γ (γ as described below t -10- I) 200404764 and substituted phenyl and phenoxy groups containing one or more of the same The substituted phenoxy group and the phenylthio group may be selected from the group consisting of γ (γ as described later) or different from each other and may be selected from the group consisting of Υ (Υ as described later). Substituted phenylthio and benzenesulfenyl groups, benzenesulfinyl and benzenesulfenyl groups containing one or more substituents selected from γ (γ as described below) which may be the same or different, One or more of the same or different materials may be selected from γ (γ As described below) benzenesulfonyl, (Ci-C6) radicals, halogenated ((: 1-0: 6) alkylcarbonyl, phenylcarbonyl, containing more than one of the same or different All may be selected from the group consisting of a phenyl mineral group, a (q-Cd alkoxycarbonyl group, a carboxyl group, a mono (Ci-CJ alkylamine group), or the same or different ones selected from γ (γ is described later) ( Ci-c6) alkylamine carbonyl, aniline carbonyl, substituted aniline carbonyl, phenyl (Ci-c6) alkane containing at least one of the same or different substituents selected from γ (γ as described below) on the ring Aminocarbonyl; substituted phenyl (Ci_c6) alkylamine carbonyl, oxy, amine, cyano, or substituted phenyl (Ci_c6) substituents containing one or more of the same or different substituents which may be on the ring 1-4 substituents of the nitro group, γ is a halogen atom, (Ci-C6) alkyl '(C2-C6) alkenyl, (c2-c6) alkynyl, ring ( c3-C6) alkyl, halogenated (C "C6) ^ ring halogenated (C3-C6) alkyl, (CrC ^) ethyloxy, halogenated dC ^) alkyloxy, (cvc6) alkylthio, halogenated ( (31-(: 6) Alkylthio, ((: 146) Alkane 25 Propylene, Halogenated ( CVC6) alkylsulfinyl, (cvc6) alkylsulfinyl, alkylsulfonyl, phenyl, halogen which is the same or different, (CVC,) alkyl, (c2-c6) alkenyl, ( c2-c6) alkynyl, cyclic (c3-c6) courtyard, halogenated (CrC,) alkyl, cyclohalogenated (C3-C6) alkyl, (CVC6: ^ -11-200404764 oxygen, halogenated (cvc6) courtyard Oxygen, (cvC6) alkylthio, halogenated (CVC6) thiol, (eve,) sulfinyl, halogenated (Ci_c6) alkylsulfinyl, (C "c6) alkylsulfonyl, halogenated alkyl Sulfonyl, (C ^ C6) alkylcarbonyl, halogenated (CVC6) alkynyl, (cvC6) alkoxycarbonyl, carboxyl, mono (CVC6) alkylamine carbonyl 'may contain the same or different (Ci_C6) Alkylamine carbonyl, hydroxyl, amine, cyano or nitro with i _ 5 substituted phenyl and phenoxy groups; containing halogen atoms selected from the same or different, (CVC6), and (C2 -C6) alkyl, (C2-C6) alkynyl, cyclic (C3-C6) alkyl, halogenated (CVCJ alkyl, cyclohalogenated (c3-c6) alkyl, (Ci_c6) alkoxy, halogenated pentyloxy, CrCd compound sulfur group, halogenated (c "c6) compound sulfur group, (Ci-Cd compound sulfinyl group, halogenated compound c "c6) Alkylsulfinyl, (Ci-C6) Alkylsulfonyl, CVCs Alkylsulfonyl, (Ci-c6) Alkylcarbonyl, Halogenated (Ci-CJI Carboxyl, (CrCd Alkoxyamido, pennyl, mono (Ci_C6) alkylamine carbonyl, containing 1-5 substituents selected from the same or different (K6) alkylamine carbonyl, hydroxyl, amine, cyano or nitro Substituted phenoxy, phenylthio; containing halogen atoms selected from the same or different, (c "c 6) alkyl, (c2-c0) alkynyl, (CVC6) alkynyl, and ring (CVC6) Alkyl, halogenated (c "c6) alkyl, cyclohalogenated ((VC6) alkyl, (CVC6) alkoxy, halogenated (Ci C6) alkyloxy (C" c6) alkyl sulfur, halogenated (c "c6) Sulfhydryl, (c "c6) alkylsulfinyl, halogenated (C1-C ^) alkylsulfinyl, (cvc6) alkylsulfinyl,

-12- 200404764 選自相同或不同均可以的鹵素原子、（Ci_C6)烷基、（c^c 燦基、（c2-c6)炔基、環（C3_C6)烷基、鹵化（Ci_c6：^_、 環齒化（c3-c6)烷基、（Ci-c6)烷氧基、鹵化（c「c6)烷氧基、 (Κ6)院硫基、鹵化（(^(^烷硫基、（Ci_c6)烷亞磺醯_、 鹵化（c^c,)烷亞磺醯基、（Ci_c6)烷磺醯基、鹵化（c ^ 6 ) 院擴基、（Cl-C6)烷基羰基、鹵化（Cl-C6)烷基羰基、（c^ C6)院氧基羰基、羧基、單（Ci-C6)烷胺羰基、相同或不同 均可以的（C1-C6)烷胺羰基、羥基、胺基、氰基或硝基之K5 個取代基的取代苯亞磺醯基、苯磺醯基；含選自相同或不 同均可以的鹵素原子、（Ci-c6)烷基、（C2-C6)烯基、（c^c^ 炔基、環（C3-C6)烷基、鹵化（c「c6)烷基、環鹵化（c3-c6：) 院基、（cvc6)烷氧基、鹵化（(31-(：6)烷氧基、（Cl-c6)烷硫 基、鹵化（cvc6)烷硫基、（Cl-C6)烷亞磺醯基、鹵化（Ci-cj 院亞磺醯基、（(：1<6)烷磺醯基、鹵化（Cl-C6)烷磺醯基、 (C「c6)烷基羰基、鹵化（Ci_c6)烷基羰基、（CVC6)烷氧基 _基、羧基、單（Cl-C6)烷胺羰基、相同或不同均可以的 (C^-C,)烷胺羰基、羥基、胺基、氰基或硝基之個取代 基的取代苯磺醯基、（(：1-(：6)烷基羰基、鹵化（Ci-C,)烷基 鑛基、苯基羰基；含選自相同或不同均可以的鹵素原子、 (c^-cj 烷基、（(Vc6)烯基、（C2_C6)炔基、環（c3-c6)烷基、 鹵化（CVC,)烷基、環鹵化（c3-c6)烷基、（cvc6)烷氧基、 鹵化（C^c,)烷氧基、（Cl-c6)烷硫基、鹵化（c「c6)烷硫基、 (c「c6)烷亞磺醯基、鹵化（Ci_c6)烷亞磺醯基、（CVC6：^ 磺醯基、鹵化（cvc6)烷磺醯基、（cvcd烷基羰基、鹵化 -13- 200404764 (cvc6)烷基羰基、（CVC6)烷氧基羰基、羧基、單（Ci_C6) 烷胺羰基、相同或不同均可以的㈧^。）烷胺羰基、羥基、· 胺基氰基或硝基之1 - 5個取代基的取代苯基羰基、（c i _-12- 200404764 is selected from the same or different halogen atoms, (Ci_C6) alkyl, (c ^ ccanyl, (c2-c6) alkynyl, cyclo (C3_C6) alkyl, halogenated (Ci_c6: ^ _, Cyclized (c3-c6) alkyl, (Ci-c6) alkoxy, halogenated (c "c6) alkoxy, (κ6) sulfanyl, halogenated ((^ (^ alkylthio, (Ci_c6) Alkyl sulfinyl group, (c ^ c,) alkylsulfinyl group, (Ci_c6) alkylsulfinyl group, halogenated (c ^ 6) alkyl group, (Cl-C6) alkyl carbonyl group, halogenated (Cl- C6) alkylcarbonyl, (c ^ C6) oxycarbonyl, carboxyl, mono (Ci-C6) alkylamine carbonyl, (C1-C6) alkylamine carbonyl, hydroxyl, amine, cyano Or substituted benzenesulfinyl, benzenesulfonyl groups of K5 substituents of nitro or nitro groups; containing halogen atoms selected from the same or different, (Ci-c6) alkyl, (C2-C6) alkenyl, ( c ^ c ^ alkynyl, cyclo (C3-C6) alkyl, halogenated (c "c6) alkyl, cyclohalogenated (c3-c6 :), alkyl, (cvc6) alkoxy, halogenated ((31- (: 6) Alkoxy, (Cl-c6) alkylthio, halogenated (cvc6) alkylthio, (Cl-C6) alkylsulfinyl sulfonyl, halogenated (Ci-cj sulfinyl sulfonyl, ((: 1 < 6) Alkylsulfonyl, halogenated (Cl-C6) alkylsulfonyl, (C "c6) alkylcarbonyl, halogenated (Ci_c6) alkylcarbonyl, (CVC6) alkoxy-yl, carboxyl, mono ( Cl-C6) alkylamine carbonyl, the same or different (C ^ -C,) alkylamine carbonyl, hydroxyl, amino, cyano or nitro substituted benzenesulfonyl, ((: 1 -(: 6) alkylcarbonyl, halogenated (Ci-C,) alkylmine, phenylcarbonyl; containing halogen atoms selected from the same or different, (c ^ -cj alkyl, ((Vc6) ene , (C2_C6) alkynyl, cyclo (c3-c6) alkyl, halogenated (CVC,) alkyl, cyclohalogenated (c3-c6) alkyl, (cvc6) alkoxy, halogenated (C ^ c,) alkane Oxygen, (Cl-c6) alkylthio, halogenated (c "c6) alkylthio, (c" c6) alkylsulfinyl, halogenated (Ci_c6) alkylsulfinyl, and (CVC6: ^ sulfonyl , Halogenated (cvc6) alkylsulfonyl, (cvcd alkylcarbonyl, halogenated-13-200404764 (cvc6) alkylcarbonyl, (CVC6) alkoxycarbonyl, carboxyl, mono (Ci_C6) alkylamine carbonyl, same or different ㈧ ^.) Alkylaminocarbonyl, hydroxyl, aminocyano or nitro substituted phenylcarbonyl with 1 to 5 substituents Base, (c i _

Cdk氧基羰基、羧基、單胺羰基、相同或不同 均可以的（C^c：6)烷胺羰基、苯胺羰基；含選自相同或不 同均可以的鹵素原子、（Ci_C6)烷基、（C^C6)烯基、（C2_C6) 炔基、環（cvc6)烷基、鹵化（Cl-C6)烷基、環鹵化（C3-C6) 院基、（cvc6)烷氧基、鹵化（Ci_c6：^氧基、（cvc6)烷硫 基、鹵化（C「c6)烷硫基、（CVC6)烷亞磺醯基、鹵化（c^Cd ® 烷亞磺醯基、（cvc6)烷磺醯基、鹵化（c「c6)烷磺醯基、 (CVC6)院基羰基、鹵化（Ci-c6)烷基羰基、（Ci-c6)烷氧基 羰基、羧基、單（Ci-CJ烷胺羰基、相同或不同均可以的 (CrCd烷胺羰基、羥基、胺基、氰基或硝基之1-5個取代 基的取代苯胺羰基、苯基（Ci-CJ烷胺羰基；在環上含有 選自相同或不同均可以的鹵素原子、（Ci-CJ烷基、（c2-c6) 烯基、（c2-c6)炔基、環（c3-c6)烷基、鹵化（Ci-c,)烷基、 φ 環鹵化（c3-c6)烷基、（CVCd烷氧基、鹵化（CVC6)烷氧基、 (CVC6)烷硫基、鹵化（c「c6)烷硫基、（Ci-C,)烷亞磺醯基、 鹵化（cvc6)烷亞磺醯基、（CVC6)烷磺醯基、鹵化（C「c6) 烷磺醯基、（CVC6)烷基羰基、鹵化（C「C6)烷基羰基、（cv c6)烷氧基羰基、羧基、單（C^-Cd烷胺羰基、相同或不同 均可以的（Ci-C,)烷胺羰基、羥基、胺基、氰基或硝基之卜5 個取代基、在環上具有至少1個所選擇之取代基之取代苯 基（Ci-C,)烷胺羰基；選自羥基、胺基、氰基或硝基之1-5 -14- 200404764 個取代基；又’ γ係與碳原子一起接鄰在苯環上，由選自 相同或不同均可以的氧原子、硫原子或氮原子（該氮原子 係爲由氫原子、（CVC6)烷基、（c2-c6)烯基、（c2-c6)炔基 或環（C3-C6)烷基所取代者）的i至2個雜原子介於（C1_CJ 伸烷基中而形成之5至6員環者}。 【實施方式】 關於本發明鹵烷磺醯苯胺衍生物之通式（I)及 14的疋我中’「鹵素原子」係爲氣原子、漠原子、蛾原子 或氟原子。「（q-C6)伸烷基」係爲亞甲基、伸乙基、亞丙 基、三亞甲基、二甲基亞甲基、四亞甲基、異亞丁基、二 甲基伸乙基、六亞甲基等之直鏈或支鏈狀0\-(：6的伸烷 基。「（C^-C^)嫌基」或「（(^-(^丨炔基」係爲同樣地直鏈或 支鏈狀之c「c6烯基或炔基。「（c^c,)烷基」係爲例如： 甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁 基、第三丁基、正戊基、新戊基、正己基等之直鏈或支鏈 狀〇\-(：6的烷基。「（Ci-CJ鹵烷基」係爲由相同或不同1 個以上的鹵原子中經取代的直鏈或支鏈狀之CrCs烷基， 例如：三氟甲基、二氟甲基、全氟甲基、全氟異丙基、氯 甲基、溴甲基、1-溴甲基、2,3-二溴丙基等。「（(：3-0：6)環 烷基」係爲環丙基、環丁基、環戊基、環己基、2 -甲基環 丙基、2-甲基環戊基等之〇：3-(：6脂環通式烷基。 「烷氧基」係爲’例如：甲氧基、乙氧基正 丙氧基、異丙氧基、正丁氧基、第二丁氧基、第三丁氧基、 正戊氧基、異戊氧基、新戊氧基、正己氧基等直鏈或支鏈 -15- 200404764 狀之c「c6烷氧基。「鹵化（c「c6)烷氧基」係爲由相同或 不同1個以上的鹵原子中經取代的直鏈或支鏈狀之Ci-Ce 烷基，例如··二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧 基等。「（C^-Cd烷氧基羰基」係爲，例如：甲氧基羰基、 乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰 基、第三丁氧基羰基等直鏈或支鏈狀之匚厂^烷氧基羰 基。「（Ci-CJ烷硫基」係爲，例如：甲硫基、乙硫基、正 丙硫基、異丙硫基、正丁硫基、第二丁硫基、第三丁硫基、 正戊硫基、異戊硫基、正己硫基等直鏈或支鏈狀之 烷硫基。「（Ci-CJ烷亞磺醯基」係爲，例如：甲亞磺醯基、 乙亞磺醯基、正丙亞磺醯基、異丙亞磺醯基、正丁亞磺醯 基、第二丁亞磺醯基、第三丁亞磺醯基、正戊亞磺醯基、 異戊亞磺醯基、正己亞磺醯基等直鏈或支鏈狀之（：「0：6烷 亞磺醯基。「（Ci-CJ烷磺醯基」係爲，例如：甲磺醯基、 乙磺醯基、正丙磺醯基、異丙磺醯基、正丁磺醯基、第二 丁磺醯基、第三丁磺醯基、正戊磺醯基、異戊磺醯基、正 己磺醯基等直鏈或支鏈狀之烷磺醯基。 Q的定義「構成原子的至少1個爲氮原子、且該氮原 子成爲與A鍵結部位之雜環」中，顯示與A的鍵結位置 爲氮原子，含有該氮原子之4-13員雜環，當該雜環爲4-8 員雜環時，更含有縮合苯環或4-7員雜環之縮合環。又’ 雜環的構成原子爲含有1或複數個氮原子以外之氧原子、 硫原子、磷原子等其他的雜原子。Q係爲，例如： -16- 200404764Cdk oxycarbonyl, carboxyl, monoamine carbonyl, the same or different (C ^ c: 6) alkylamine carbonyl, aniline carbonyl; containing halogen atoms selected from the same or different, (Ci_C6) alkyl, ( C ^ C6) alkenyl, (C2_C6) alkynyl, cyclo (cvc6) alkyl, halogenated (Cl-C6) alkyl, cyclohalogenated (C3-C6) alkyl, (cvc6) alkoxy, halogenated (Ci_c6: ^ Oxy, (cvc6) alkylthio, halogenated (C "c6) alkylthio, (CVC6) alkylsulfinylfluorenyl, halogenated (c ^ Cd ® alkylsulfinylfluorenyl, (cvc6) alkylsulfinylfluorenyl, Halogenated (c, c6) alkanesulfonyl, (CVC6) alkyl carbonyl, halogenated (Ci-c6) alkylcarbonyl, (Ci-c6) alkoxycarbonyl, carboxyl, mono (Ci-CJ alkylamine carbonyl, same Or different (CrCd alkylamine carbonyl, hydroxyl, amine, cyano or nitro substituted aniline carbonyl of 1-5 substituents, phenyl (Ci-CJ alkylamine carbonyl; Or different halogen atoms, (Ci-CJ alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, cyclic (c3-c6) alkyl, halogenated (Ci-c,) alkyl, φ ring halogenated (c3-c6) alkyl, (CVCd alkoxy, halogenated (CVC6) alkyl (CVC6) alkylthio, halogenated (c "c6) alkylthio, (Ci-C,) alkylsulfinyl, halogenated (cvc6) alkylsulfinyl, (CVC6) alkylsulfinyl, halogenated (C "c6) alkylsulfonyl, (CVC6) alkylcarbonyl, halogenated (C" C6) alkylcarbonyl, (cv c6) alkoxycarbonyl, carboxyl, mono (C ^ -Cd alkylamine carbonyl, same or Different (Ci-C,) alkylamine carbonyl, hydroxyl, amine, cyano or nitro groups with 5 substituents, substituted phenyl groups with at least 1 selected substituent on the ring (Ci-C ,) Alkylamine carbonyl; 1-5 -14-200404764 substituents selected from hydroxyl, amine, cyano or nitro; and 'γ is adjacent to the benzene ring together with carbon atoms, and is selected from the same or Oxygen, sulfur, or nitrogen atoms that can be different (the nitrogen atom is a hydrogen atom, (CVC6) alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, or ring (C3-C6) Those substituted by an alkyl group) having i to 2 heteroatoms between (C1_CJ alkylene group and a 5 to 6 membered ring)}. [Embodiment] The general formula ( I) and 14's "'halogen atom' is Atom, desert atom, moth atom or fluorine atom. "(Q-C6) alkylene" is methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene Linear or branched 0 \-(: 6 alkylene, such as isobutylene, dimethylethylene, hexamethylene, etc. "" (C ^ -C ^) anhydroxyl "or" (( ^-(^ 丨 alkynyl "refers to c" c6alkenyl or alkynyl, which is also straight or branched. "(C ^ c,) alkyl" is, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, A linear or branched chain of neopentyl, n-hexyl, etc. 0-(: 6. "(Ci-CJ haloalkyl" is a straight substituted by one or more halogen atoms which are the same or different Chain or branched CrCs alkyl, for example: trifluoromethyl, difluoromethyl, perfluoromethyl, perfluoroisopropyl, chloromethyl, bromomethyl, 1-bromomethyl, 2,3 -Dibromopropyl, etc. "((: 3-0: 6) cycloalkyl" is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclopropyl, 2-methyl Cyclopentyl and the like: 0: 3-(: 6 alicyclic alkyl groups. "Alkoxy" means' for example: methoxy, ethoxy n-propoxy, isopropoxy, n-butoxy Straight-chain or branched, such as second butoxy, third butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, etc.-15-200404764 c "c6 alkoxy. "Halogenated (c" c6) alkoxy "is a linear or branched Ci- substituted with one or more halogen atoms which are the same or different Ce alkyl, for example, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, etc. "(C ^ -Cd alkoxycarbonyl" is, for example, methoxy Alkylcarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, tertiary butoxycarbonyl, etc. linear or branched ^ alkoxycarbonyl groups. "Ci-CJ alkylthio" is, for example: methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, second butylthio, third butylthio, n-pentylthio Alkyl, isopentylthio, n-hexylthio, etc. straight-chain or branched alkylthio groups. "(Ci-CJ alkylsulfenylfluorenyl" is, for example: methylsulfinyl, ethylsulfinyl, N-propylsulfinyl sulfenyl, isopropylsulfinyl sulfinyl, n-butylsulfinyl sulfinyl, n-butylsulfinyl sulfinyl, third butylsulfinyl sulfinyl, n-pentylsulfinyl sulfinyl, isopentylsulfinyl Straight-chain or branched (such as n-hexylsulfinyl) ("0: 6 alkylsulfinylsulfonyl." (Ci-CJ alkylsulfinyl) "is, for example: methylsulfinyl, ethylsulfinyl , N-propanesulfenyl, isopropylsulfonyl, n-butylsulfonyl, second sulfonyl, Linear or branched alkylsulfonyl groups such as tributylsulfonyl, n-pentylsulfonyl, isopentylsulfonyl, n-hexanesulfonyl and the like. Definition of Q "At least one of the constituent atoms is a nitrogen atom, and This nitrogen atom becomes a heterocyclic ring at the bonding site with A. "It is shown that the bonding position with A is a nitrogen atom, a 4-13 member heterocyclic ring containing the nitrogen atom, and when the heterocyclic ring is a 4-8 member heterocyclic ring. It also contains a condensed benzene ring or a condensed ring of 4-7 membered heterocyclic ring. The constituent atoms of the heterocyclic ring include oxygen atoms, sulfur atoms, phosphorus atoms and other heteroatoms other than one or more nitrogen atoms. Q system For example: -16- 200404764

Q-6 Q-7 q，3 Q-9Q-6 Q-7 q, 3 Q-9

{式中，G1、G2爲相同或不同均可以的氧原子、 子、N-R3’（式中，R3’爲氫原子、（Ci-C6)烷基、氯基 基、苯基（Ci-C6)烷基、在環上含有1個以上之相同 硫壞 、硝 同均可以的選自Y’（Y’如後所述）之取代基的取代苯基 (eve：6)院基、苯基或含有1個以上之相同或不同均可以 的選自Υ’ （Y，如後所述）之取代基的取代苯基）、N-OR4’（式中’ R4’爲氫原子、（CVC6)烷基、苯基（CrC6)烷蔘 或在環上含有1個以上之相同或不同均可以的選自 (Y，如後所述）之取代基的取代苯基（Ci-C6)烷基）、N- NR5’R6’（式中，R5’及R6’爲相同或不同均可以的氫原孑、 苯基或含有1個以上之相同或不同均可以的選自Y，（γ’ -17- 200404764 如後所述）之取代基的取代苯基。又，R5’及R6’同時爲（C3-C6)伸烷基）或CR7R8(式中，r7’及R8’爲相同或不同均可以 的氣原子、（C^-Cs)院基、院氧基鑛基、氰基或硝 基）， J1爲氧原子、硫原子或N-R9(式中，R9爲氫原子、（CVC6) 烷基、苯基（Ci-CJ烷基、在環上含有1個以上之相同或 不同均可以的選自Y，（Y，如後所述）之取代基的取代苯基 (Ci-C：6)烷基、苯基，含有1個以上之相同或不同均可以 的選自Y’（Y’如後所述）之取代基的苯基、雜環基（雜環 基係與申請專利範圍第2項中所述相同）、含有1個以上 之相同或不同均可以的選自Y’（Y’如後所述）之取代基的 取代雜環基（雜環基係與上述相同）、雜環基（Ci-C6)院基（雜 環基係與上述相同）、在環上含有1個以上之相同或不同 均可以的選自Y，（Y，如後所述）之取代基的取代雜環基 (Ci-C6)院基（雜環基係與上述相同）、單（c「c6)院胺鑛基、 相同或不同均可以的（c^c,)烷胺羰基、苯胺羰基，或在 環上含有1個以上之相同或不同均可以的選自γ，（γ，如 後所述）之取代基的取代苯胺羰基）， J2及J3係爲相同或不同均可以的氧原子、硫原子Ν_ R9(式中’ R9與上述相同）、R^C_R11(式中R1。及Ril係爲 相同或不同均可以的氫原子、（CVC6)烷基、鹵化（CVC6) 院基、（cvc6)院氧基、鹵化（Cl-C6)烷氧基、（Ci_c6)院硫 基、鹵化（c「c6)烷硫基、（cvc6)烷亞磺醯基、鹵化（C「C6) 烷亞磺醯基、（CVC6)烷磺醯基、鹵化（C「C6)烷磺醯基、 200404764 苯基（Cl-C6)烷基、在環上含有丨個以上之相同或不同均 可以的選自Y’（Y’如後所述）之取代基的取代苯基（Ci_c6) ί元基、本基或a有1個以上之相同或不同均可以的選自γ， (Y，如後所述）之取代基的取代苯基）、c = 〇或c==s， J4及JM系爲相同或不同C-R12(式中，爲氫原子、 鹵素原子、（cvc6)烷基、鹵化（C「C6)烷基、（κ6)烷氧 基、鹵化（c i - C 6)烷氧基、（c i - c 6)烷硫基、鹵化（c「C 6)院 硫基、（CVC6)烷亞磺醯基、鹵化（Ci_c6)烷亞磺醯基、（c「 C6)院擴醯基、鹵化（Ci-C6)院磺醯基、苯基（c「c6)燒基、 在環上含有1個以上之相同或不同均可以的選自γ，（γ， 如後所述）之取代基的苯基（Ci-C：6)烷基、苯基，含有丨個 以上之相同或不同均可以的選自Y’（Y，如後所述）之取代 基的取代苯基或氰基）或氮原子， w爲氧原子、硫原子、N-R9(式中，R9與上述相同）或 RM-C-R^式中，R1G及RH與上述相同）， R9與上述相同， R13及R14係爲相同或不同均可以的氫原子、鹵素原 子、（c^c6)烷基、鹵化（CVC6)烷基、（CVC6)烷氧基、鹵 化（c「c6)烷氧基、（Cl-C6)烷硫基、鹵化（Ci-C,)烷硫基、 (c「c6)院亞磺醯基、鹵化（c^-Cs)院亞磺醯基、（c^-c^)院 磺醯基、鹵化（CVC6)烷磺醯基、苯基（C1-C6)烷基、在環 上含有1個以上之相同或不同均可以的選自γ’（γ’如後 所述）之取代基的取代苯基（(^-(：6)烷基、苯基，含有1個 以上之相同或不同均可以的選自Υ ’（ Υ ’如後所述）之取代 200404764 基的取代菜# 本基、雜環基（雜環基與上述相同）’含有1個以 上之相同或不同均可以的選自γ，（γ，如後所述）之取代基 · 的取代雜環基（雜環基與上述相同）、雜環基（Ci_C6M^基（雜 · 環基與上述相同），在環上含有1個以上之相同或不同均 “ 可以的選自Y’（Y，如後所述）之取代基的取代雜環基（Ci_ C6)院基（雜環基與上述相同）、單（C^c,)烷胺羰基、相同 或不同均可以的（Ci_c6)烷胺羰基、苯胺羰基，在環上含 有1個以上之相同或不同均可以的選自Y’（Y’如後所述） 之取代基的取代苯胺羰基或氰基， 鲁 R13及R16係爲相同或不同均可以的氫原子或（Ci-c6) 烷基， X’爲相同或不同均可以的氫原子、鹵素原子、（Κ6) 烷基、（c2-c6)烯基、（C2-C6)炔基、環（C3-C7)烷基、鹵化 (C「c6)烷基、環鹵化（c3-c7)烷基、（CVCJ烷氧基、鹵化 (。1-(：6)烷氧基、（(：146)烷硫基、鹵化（〇1-〇6)烷硫基、（(：1-0：6) 烷亞磺醯基、鹵化（c「c6)烷亞磺醯基、（cvc6)烷磺醯基、 0 鹵化（c^-c,)烷磺醯基、苯基、含有1個以上之相同或不 同均可以的選自Y，（ Y ’如後所述）之取代基的取代苯基、 苯氧基，含有1個以上之相同或不同均可以的選自γ’（γ’ 如後所述）之取代基的苯氧基、苯硫基，含有1個以上之 相同或不同均可以的選自γ ’（γ ’如後所述）之取代基之取 代苯硫基、苯亞磺醯基，含有1個以上之相同或不同均可 以的選自γ，（Υ，如後所述）之取代基的取代苯亞磺醯基、 苯磺醯基，含有1個以上之相同或不同均可以的選自γ -20- ZUU4U4/04 (Y， i D後所述）之取代基的取代苯磺醯基、（Ci-C6)烷基羰 國化（eve,)烷基羰基、苯基羰基，含有1個以上之 相同或不同均可以的選自γ，（γ，如後所述）之取代基的取 代本知醯基、d-G)烷氧基羰基、羧基、單（cvc6)烷胺 羯基、相同或不同均可以的（(：1<6)烷胺羰基、苯胺羰基， 在環上含有！個以上之相同或不同均可以的選自γ，（γ， 如後所述）之取代基的取代苯胺羰基、苯基（Ci_C6)烷胺羰 基，在環上含有1個以上之相同或不同均可以的選自Y’ (γ’如後所述）之取代基的取代苯基（c「c6)烷胺羰基、選 自羥基、胺基、氰基或硝基之1-4個取代基， Y’爲相同或不同均可以的氫原子、鹵素原子、（κ6) 烷基、（C2-C6)烯基、（c2-c6)炔基、環（c3-c6)烷基、鹵化 (CVC6)烷基、環鹵化（C3-C6)烷基、（CVC6)烷氧基、鹵化 (0：1-(：6)烷氧基、（〇1-〇6)烷硫基、鹵化（(：1-(：6)烷硫基、（(：1-(：6) 烷亞磺醯基、鹵化（c「c6)烷亞磺醯基、（G-Cd烷磺醯基、 鹵化（C「C6)院磺醯基、苯基、苯氧基、（C1-C6)焼基鑛基、 鹵化（Κό)焼基鑛基、苯基_基' (Cl-C6)院氧基_基' 殘基、單（CVCJ烷胺羰基、二（CVC,)烷胺羰基，選自苯 胺鑛基、經基、胺基、氰基或硝基之1-5個取代基}° 「雜環基」係爲，例如：吡啶基、吡啶氧化物基、 嘧D定基、社畊基、三哄基、呋喃基、四氫呋喃基、噻吩基、 四氨瞎吩基、四氫哌喃基、四氫硫代哌喃基、噚唑基、異 噚嗤基、曙二唑基、噻唑基、異噻唑基、噻二唑基、咪唑 基、二π坐基、啦哩基、嗎福啡基等。 -21- 200404764 本發明的鹵烷磺醯苯胺衍生物之鹽類係爲適用於農藥 使用之鹽類’例如：鋰鹽、鈉、鉀等鹼金屬鹽類，鈣、鎂 等鹼土族鹽類與鹽、鐵等重金屬之鹽類，與其鋁、鉛等其 他金屬鹽類等之無機金屬類之鹽類，與銨鹽等有機鹼之鹽 類等，形成水合物爲較佳。 本發明通式（I)所表示的鹵烷磺醯苯胺衍生物，其構 造式中含有1或多個不對稱碳原子或不對稱中心時、2種 以上光學異構體及非鏡像異構物存在時，本發明係爲包括 全部各種光學異構體及含有其任意比率之混合物者。又， 本發明通式（I)所表示的鹵烷磺醯苯胺衍生物，其構造式 中由碳-碳雙鍵鍵結或碳-氮雙鍵鍵結而來之2種幾何異構 物存在的情形下，本發明係爲包括全部各種幾何異構物及 含有其任意比率之混合物者。 本發明鹵烷磺醯苯胺衍生物之較佳態樣，作爲雜環之 Q中，較佳爲含有1-4個氮原子、0-1個氧原子及〇-1個 硫原子的5-6員雜環，更佳爲該5-6員雜環形成縮合環。 特佳爲Q-l、Q-2、Q-3等。Q上的取代基較佳爲苯基（CV C6)烷基、取代苯基（Ci-CJ烷基、苯基、取代苯基、吡啶 基及取代吡啶基等。R1爲鹵烷基，較佳爲氟甲基、更佳 爲三氟甲基或二氟甲基，其位置較佳爲第二位置。R2較 佳爲氫原子。G及G1較佳爲氧原子。Μ較佳爲0。 本發明之通式（I)鹵烷磺醯苯胺衍生物，係經由例如 下列圖通式之製造方法而製備。 -22- 200404764 製造方法1{In the formula, G1 and G2 are the same or different oxygen atoms, ions, and N-R3 '(wherein, R3' is a hydrogen atom, (Ci-C6) alkyl, chloro, and phenyl (Ci- C6) an alkyl group, a substituted phenyl group (eve: 6) containing a substituent selected from Y '(Y' as described later) containing one or more of the same sulfur group and nitrate group, and a benzene group Or a substituted phenyl group containing at least one of the same or different substituents selected from the group consisting of ， '(Y, as described later), N-OR4' (wherein 'R4' is a hydrogen atom, (CVC6 ) Alkyl, phenyl (CrC6) alkane, or substituted phenyl (Ci-C6) alkyl containing at least one of the same or different substituents selected from (Y, described later) on the ring ), N- NR5'R6 '(where R5' and R6 'are the same or different hydrogen atoms, phenyl, or one or more of the same or different may be selected from Y, (γ'- 17-200404764 as described below) substituted phenyl of the substituent. Also, R5 'and R6' are both (C3-C6) alkylene) or CR7R8 (wherein, r7 'and R8' are the same or different. Possible gas atom, (C ^ -Cs) hospital base, hospital oxygen Base, cyano, or nitro), J1 is an oxygen atom, a sulfur atom, or N-R9 (wherein R9 is a hydrogen atom, (CVC6) alkyl group, phenyl (Ci-CJ alkyl group, One or more of the same or different substituted phenyl (Ci-C: 6) alkyl and phenyl groups selected from the substituents of Y, (Y, as described later) may be one or more of the same or different All may be selected from the group consisting of a phenyl group, a heterocyclic group (the heterocyclic group is the same as described in item 2 of the scope of patent application), a substituent selected from Y '(Y' is described later), Different types of substituted heterocyclic groups (heterocyclic groups are the same as above) selected from Y '(Y' is described later), heterocyclic groups (Ci-C6), and heterocyclic groups (heterocyclic groups and The same as above), a substituted heterocyclic group (Ci-C6), a heterocyclic group (heterocyclic group system) selected from Y, (Y, as described later) which may contain one or more of the same or different in the ring Same as above), single (c "c6) amine amine group, the same or different (c ^ c,) alkylamine carbonyl, aniline carbonyl, or any one or more of the same or different ring From γ, ( , As described below) Substituted aniline carbonyl of the substituent), J2 and J3 are the same or different oxygen atom, sulfur atom N_R9 (where R9 is the same as above), R ^ C_R11 (where R1 And Ril is the same or different hydrogen atom, (CVC6) alkyl, halogenated (CVC6) courtyard, (cvc6) courtyard oxygen, halogenated (Cl-C6) alkoxy, (Ci_c6) courtyard thio , Halogenated (c "c6) alkylthio, (cvc6) alkylsulfinyl, halogenated (C" C6) alkylsulfinyl, (CVC6) alkylsulfinyl, halogenated (C "C6) alkylsulfinyl , 200404764 phenyl (Cl-C6) alkyl, substituted phenyl (Ci_c6) containing at least one of the same or different substituents selected from Y '(Y' as described below) on the ring Group, the main group or a may have one or more of the same or different and may be selected from the group consisting of γ, (Y, as described later) substituted phenyl), c = 〇 or c = = s, J4 and JM Is the same or different C-R12 (wherein it is a hydrogen atom, a halogen atom, a (cvc6) alkyl group, a halogenated (C6) alkyl group, a (κ6) alkoxy group, a halogenated (ci-C 6) alkoxy group (Ci-c 6) alkylthio, halogenated (c "C 6) sulfanyl, (CVC6) alkylsulfinyl, halogenated (Ci_c6) alkylsulfinyl, (c "C6) sulfanyl, halogenated (Ci-C6) sulfinyl, phenyl (c "C6) a phenyl group, a phenyl (Ci-C: 6) alkyl group, or a phenyl group which contains one or more of the same or different substituents on the ring and may be selected from γ, (γ, as described later) A substituted phenyl or cyano group containing at least one of the same or different substituents selected from Y ′ (Y, as described later) or a nitrogen atom, w is an oxygen atom, a sulfur atom, and N-R9 (Where R9 is the same as above) or RM-CR ^ where R1G and RH are the same as above), R9 is the same as above, and R13 and R14 are the same or different hydrogen atom, halogen atom, (c ^ c6) alkyl, halogenated (CVC6) alkyl, (CVC6) alkoxy, halogenated (c "c6) alkoxy, (Cl-C6) alkylthio, halogenated (Ci-C,) alkylthio, ( c "c6) sulfinylsulfenyl, halogenated (c ^ -Cs) sulfinylsulfinyl, (c ^ -c ^) sulfinylsulfonyl, halogenated (CVC6) alkylsulfonyl, phenyl (C1-C6) ) Alkyl group, which may contain one or more of the same or different in the ring, may be selected from γ '(γ' as described later) ) 'S substituted phenyl ((^-(: 6) alkyl, phenyl, containing one or more of the same or different may be selected from Υ' (Υ 'as described below) of the substitution of the 200404764 group Substituted vegetable # This group, heterocyclic group (heterocyclic group is the same as the above), a substituted heterocyclic group containing one or more of the same or different members selected from γ, (γ, as described later) (Heterocyclic group is the same as above), heterocyclic group (Ci_C6M ^ group (hetero and cyclic group is the same as above), contains one or more of the same or different on the ring, may be selected from Y '(Y, as follows The substituted heterocyclic group (Ci_C6) of the substituent (the heterocyclic group is the same as above), the mono (C ^ c,) alkylamine carbonyl group, the same or different (Ci_c6) alkylamine carbonyl group, Aniline carbonyl, which contains one or more of the same or different substituents selected from Y '(Y' as described later) on the ring, may be substituted aniline carbonyl or cyano. R13 and R16 are the same or different. Acceptable hydrogen atom or (Ci-c6) alkyl group, X 'is the same or different hydrogen atom, halogen atom, (Κ6) alkyl group, (c2 -c6) alkenyl, (C2-C6) alkynyl, cyclic (C3-C7) alkyl, halogenated (C "c6) alkyl, cyclohalogenated (c3-c7) alkyl, (CVCJ alkoxy, halogenated ( . 1-(: 6) alkoxy, ((: 146) alkylthio, halogenated (〇1-〇6) alkylthio, ((: 1-0: 6) alkylsulfinyl, halogenated (c " c6) alkylsulfinyl, (cvc6) alkylsulfinyl, 0 halogenated (c ^ -c,) alkylsulfinyl, phenyl, one or more of the same or different may be selected from Y, (Y Substituted phenyl and phenoxy groups of the substituents as described below), phenoxy groups and benzenes which contain one or more substituents which are the same or different and are selected from the group consisting of γ '(γ' will be described later) A thio group, which contains one or more of the same or different substituents selected from γ ′ (γ ′ as described later), a substituted phenylthio group and a phenylsulfinyl group, and contains one or more of the same or different Substituted benzenesulfenyl and benzenesulfenyl groups which are selected from γ, (i.e., as described later) and may be selected from γ -20- ZUU4U4 / 04 Substituted benzenesulfonyl, (Ci-C6) alkylcarbonyl (eve,) alkylcarbonyl, phenylcarbonyl, which are substituted by (Y, i D), contain more than one of the same or different Can be selected from γ, (γ, as described later) Substituted phosphonium groups, dG) alkoxycarbonyl groups, carboxyl groups, mono (cvc6) alkylamine fluorenyl groups, the same or different ((: 1 < 6) alkylamine carbonyl groups, aniline carbonyl groups, which are contained on the ring More than one of the same or different may be selected from γ, (γ, as described later) substituted aniline carbonyl, phenyl (Ci_C6) alkylamine carbonyl, and the ring contains one or more of the same or different Any of substituted phenyl (c "c6) alkylamine carbonyl groups selected from the substituents of Y '(γ' as described later), and 1-4 substituents selected from hydroxyl, amine, cyano, or nitro groups Y ′ is the same or different hydrogen atom, halogen atom, (κ6) alkyl, (C2-C6) alkenyl, (c2-c6) alkynyl, cyclo (c3-c6) alkyl, and halogenated (CVC6 ) Alkyl, cyclohalogenated (C3-C6) alkyl, (CVC6) alkoxy, halogenated (0: 1-(: 6) alkoxy, (〇1-〇6) alkylthio, halogenated ((: 1-(: 6) Alkylthio, ((: 1-(: 6) Alkylsulfinyl, Halogenated (c "c6) Alkylsulfinyl, Halo (G-Cd Alkylsulfinyl, Halo (C" C6) sulfonyl, phenyl, phenoxy, (C1-C6) fluorenyl ores, halogenated (Κό) 焼Mineral group, phenyl group ((Cl-C6) oxy group) residue, mono (CVCJ alkylamine carbonyl group, di (CVC,) alkylamine carbonyl group, selected from aniline group, warp group, amine group, 1-5 substituents of cyano or nitro} ° "Heterocyclyl" is, for example: pyridyl, pyridyl oxide, pyrimidyl, social group, trisyl, furanyl, tetrahydrofuranyl, Thienyl, tetraaminobenzoyl, tetrahydropiperanyl, tetrahydrothiopiperanyl, oxazolyl, isofluorenyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, imidazole Base, two π-base, laricyl, morphine and so on. -21- 200404764 The salts of the halosulfanilanilide derivatives of the present invention are salts suitable for use in pesticides. For example: lithium salts, sodium, potassium and other alkali metal salts, calcium and magnesium alkaline earth salts, and Salts of heavy metals such as salts and iron, salts of inorganic metals such as other metal salts such as aluminum and lead, and salts of organic bases such as ammonium salts, etc., are preferably hydrates. When the halosulfonylanilide derivative represented by the general formula (I) of the present invention contains one or more asymmetric carbon atoms or asymmetric centers in the structural formula, two or more optical isomers and non-image isomers When present, the present invention includes all optical isomers and mixtures containing any ratio thereof. In addition, the halosulfonylanilide derivative represented by the general formula (I) of the present invention has two geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in its structural formula. In the case of the present invention, the present invention includes all kinds of geometric isomers and mixtures containing any ratio thereof. In a preferred embodiment of the halosulfanilanilide derivative of the present invention, in the Q of the heterocyclic ring, it is preferably 5-6 containing 1-4 nitrogen atoms, 0-1 oxygen atoms, and 0-1 sulfur atoms. A membered heterocyclic ring, more preferably the 5-6 membered heterocyclic ring forms a condensed ring. Particularly preferred are Q-1, Q-2, Q-3 and so on. The substituent on Q is preferably a phenyl (CV C6) alkyl group, a substituted phenyl (Ci-CJ alkyl group, a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, etc.). R1 is a haloalkyl group, preferably Is fluoromethyl, more preferably trifluoromethyl or difluoromethyl, and its position is preferably the second position. R2 is preferably a hydrogen atom. G and G1 are preferably oxygen atoms. M is preferably 0. This The general formula (I) halosulfanilanilide derivative of the invention is prepared through, for example, a production method of the following general formula. -22- 200404764 Production method 1

(I-l) H?N-R3, H?N-OR4, 或 - (1-2) (式中，Ri、R2、R3、R4、R5、R6、A、Q、X 及 m 係 與前述相同。R2’爲（CVC6)烷基、（C^C,)烷基羰基、鹵化 (C^-C,)烷基羰基、含有選自1個以上相同或不同Y(Y如 上所述）之取代基的苯基羰基、（c^c 6)苯磺醯基、鹵化 (C「C6)苯磺醯基或含有選自1個以上Y(Y如上所述）之取 .代基的苯磺醯基， G，爲N-R3(式中，R3如上所述）、n_0r4(式中’ R4如 上所述）或n-nr5r6(式中，R5及R6如上所述）， L爲鹵素原子等之脫離基）。(Il) H? N-R3, H? N-OR4, or-(1-2) (wherein Ri, R2, R3, R4, R5, R6, A, Q, X and m are the same as described above. R2 'is (CVC6) alkyl, (C ^ C,) alkylcarbonyl, halogenated (C ^ -C,) alkylcarbonyl, and contains one or more substituents selected from the same or different Y (Y is as described above) Phenylcarbonyl, (c ^ c 6) benzenesulfonyl, halogenated (C "C6) benzenesulfonyl, or benzenesulfonyl containing one or more selected from Y (Y as described above). G is N-R3 (where R3 is as described above), n_0r4 (where R4 is as described above) or n-nr5r6 (where R5 and R6 are as described above), and L is a halogen atom or the like base).

通式（II)所表示的化合物之鹼存在下，視需要地使用 相關移動觸媒，於惰性溶劑存在下或不存在下與通式Q-H -23- 200404764 表示之雜環反應，可得通式（III)所表示之化合物，該化合 物可單獨分離或不單獨分離。在惰性溶劑存在下或不存在 下與還原劑等反應可得通式（IV)所表示之胺化合物，該化 合物可單獨分離或不單獨分離。在鹼存在下，惰性溶劑存 在或不存在下與RiSC^-LC式中，R1及 L於上述相同）或 (R402)20(式中，R1與上述相同）表示的鹵烷磺醯基衍生 物反應，而製備通式（1-1)表示的本發明化合物。再者， 單獨分離或不單獨分離通式（1-1)化合物、鹼存在下、於 惰性溶劑存在下或不存在下與通式 R2、L(式中，R2’及L 如上所述）化合物反應後，可製備通式（1-2)表示之本發明 化合物。再者，於在通式（1-1)或（1-2)化合物單獨分離或 不單獨分離、惰性溶劑存在或不存在下，與通式H2N-R3 (式 中，R3如上所述）表示之胺衍生物、H2N-OR4(式中，R4如 上所述）表示之氧化物衍生物或H2N-NR5R6(式中’ R5及R6 如上所述）表示之胼衍生物反應，而製造通式（卜3 )表不之 本發明化合物。 (1-1) 通式（II)—通式（ΙΠ) 起始物質之通式（II)化合物，例如：Chem· Soc·， 684( 1 942)，Indian J· Chem·，11，609( 1 973)，Beilsteins Handbuch der Organischen Chemie，7，290,寺 5己載的方式 或按照其爲標準而製造。Q-Η表示的雜環係爲例如·· 2，3_ 二氫-3Η-1，2,4-***基-3-酮衍生物，W098·38176號公報 記載的方法或按照其標準、四嗤基衍生物係如J·In the presence of a base of a compound represented by the general formula (II), a relevant mobile catalyst is used as needed, and the general formula QH -23-200404764 is reacted in the presence or absence of an inert solvent to obtain the general formula The compound represented by (III) may be isolated alone or not separately. The amine compound represented by the general formula (IV) can be obtained by reacting with a reducing agent or the like in the presence or absence of an inert solvent, and the compound can be isolated alone or not. In the presence of a base, the presence or absence of an inert solvent is the same as in the RiSC ^ -LC formula, where R1 and L are the same as above) or (R402) 20 (wherein R1 is the same as above) And react to prepare a compound of the present invention represented by the general formula (1-1). In addition, the compound of the general formula (1-1) is isolated with or without the compound of the general formula R2, L (where R2 'and L are as described above) in the presence of a base, in the presence or absence of an inert solvent, or not. After the reaction, the compound of the present invention represented by the general formula (1-2) can be prepared. Furthermore, it is represented by the general formula H2N-R3 (wherein R3 is as described above) in the presence of the compounds of the general formula (1-1) or (1-2) isolated or not isolated, the presence or absence of an inert solvent. An amine derivative, an oxide derivative represented by H2N-OR4 (where R4 is as described above) or a hydrazone derivative represented by H2N-NR5R6 (wherein R5 and R6 are as described above) are reacted to produce a general formula ( B) The compounds of the present invention are represented. (1-1) General formula (II)-general formula (II) The compound of general formula (II) as the starting material, for example: Chem · Soc ·, 684 (1 942), Indian J · Chem ·, 11,609 ( 1 973), Beilsteins Handbuch der Organischen Chemie, 7, 290, Temple 5 is manufactured in accordance with or in accordance with the standard. The heterocyclic system represented by Q-Η is, for example, 2,3_dihydro-3Η-1,2,4-triazolyl-3-one derivative, the method described in WO 9838176, or the standard thereof. Fluorenyl derivatives such as J ·

Heterocycl. Chem.，35(2)，405(1998)寺的 5己載方法或按 -24- 200404764Heterocycl. Chem., 35 (2), 405 (1998) Temple of the 5th method or press -24-200404764

照其標準而製造。其Q-H表示的雜環係按照國際特許公 開 WO9 1 -3470 號公報、J. Chem· Soc. Perkin Trans· 1，22, 2644(1973)、特開平 9-100271 號公幸艮、Liebigs Annalen der Chemie，675，1 80( 1 964)、J · Chem. Soc. (C)，747( 1 967)、 USP 5 7 2 8 8 3 4 號公報、J. Heterocycl. Chem·， 22, 409(1985)、特開昭 60-146879 號公報、特開平 6-306061 號公報、特開昭 63-41466 號公報、DokladyAkademii Nauk SSSR (Dokl. Akad. Nauk SSSR)，158，1 3 5 8 ( 1 964)、W098-11079 號公幸艮、Drug Research (Drug res·)，（1)，189(1968)， J.Heterocycl. Chem., 15(7)，1 2 3 1 ( 1 97 8)，J. Chem. Soc. Perkin Trans. 2， 1 670( 1 979)，J. Am. Chem. Soc·， 80, 3908(1958) 、 Journal fuer Praktische Chemie, 311， 477( 1 969)，Chemische Berichet，88，1 3 5 1 ( 1 95 5 )等記載方 法或按照其標準而製造。 在本反應使用的惰性溶劑中，以明顯地不會阻害本反 應者爲佳，例如：二***、四氫呋喃、二噚烷等鏈狀或環 狀醚類、苯、甲苯、二甲苯等芳香族烴類、二氯甲烷、三 氯甲烷、四氯化碳等鹵化烴類，氯苯、二氯苯等氯化芳香 族烴類，丙酮、甲基乙基酮等酮類，乙腈等腈類等，醋酸 乙酯等酯類，N，N-二甲基甲醯胺、N，N-二甲基乙醯胺等醯 胺類，二甲亞碾、1，3 -二甲基-2 -咪唑啉酮、水等惰性溶劑， 該惰性溶劑可單獨或2種以上混合使用。 本發明使用的鹼，例如··三乙胺、二異丙基乙胺、1，8 -二BY二環-[5·4·0]-7-十一烯、吡啶基等含氮有機鹼類，碳 -25- 200404764 酸鈉、碳酸鉀、碳酸氫鈉、氫氧化鈉、氫氧化鉀、氫化鈉、 金屬鈉等無機鹼類，醋酸鈉、醋酸鉀等有機鹼類，乙氧基 鈉、第三丁基鉀等醇化物。鹼的使用量由中和反應發生之 酸的量爲佳，過量使用亦可。 本發明中使用的相關移動觸媒係爲，例如：四正丁基 銨溴、苄基三乙基銨溴等四級銨鹽，18-環-6-醚等環狀醚。 相關移動觸媒的使用量相對於通式（III)化合物適宜選擇爲 0 · 0 1至0 · 5倍的範圍爲佳。 本發明中的莫耳反應，各反應劑以等莫耳使用爲佳， 各反應劑亦可過量使用。反應溫度係於-20 °C乃至使用惰 性溶劑的迴流溫度下進行。反應時間由於反應規模、反應 溫度而沒有一定，可於數分至48小時之範圍內適當選擇。 反應終了後，根據含有標的的物之反應系以習知方法 單獨分離標的物，視需要地以再結晶法、蒸餾法、矽膠管 柱層析法等純化而製造標的物。又，亦可不單獨分離本反 應終了後之標的物，以提供後續之反應。 (1-2) 通式（III)—通式（IV) 本反應所使用的惰性溶劑係爲，例如：甲醇、乙醇等 醇類，四氫呋喃、二噚烷等醚類，水等，惰性溶劑可單獨 或2種以上混合使用。再者，下列所示作爲還原劑使用的 酸性水溶液亦可使用惰性溶劑。 本反應所使用的遠原劑係例舉爲金屬·酸、金屬-鹽 等，其中金屬例如爲鐵、錫、鋅等，酸例如爲鹽酸、硫酸 等無機酸、醋酸等有機酸類、氯化錫等，鹽例如爲氯化銨 -26- 200404764 等。又，亦可使用其組合。 還原劑使用量相對於通式（III)化合物，係以金屬爲 卜10倍、酸及鹽爲0.05-10倍之範圍使用較佳。反應溫度 較佳爲0 -1 5 0 °c，反應時間由於反應規模、反應溫度等而 沒有一定，較佳爲數分至4 8小時之範圍。 又，還原反應在觸媒存在下，亦可進行接觸氫添加法， 其中觸媒例如爲鈀碳、鉑、阮來鎳等。 反應終了後，根據含有標的的物之反應系以習知方法 單獨分離標的物，視需要地以再結晶法、蒸餾法、矽膠管 柱層析法等純化而製造標的物。又，亦可不單獨分離本反 應終了後之標的物，以提供後續之反應。 (1-3) 通式（IV)—通式（V) 本發明所使用的惰性溶劑中，以不會阻害本發明的進 行爲佳，例如：二乙胺、四氫呋喃、二噚烷等鏈狀或環狀 醚類，苯、甲苯、二甲苯等芳香族烴類，二氯甲烷、三氯 甲烷、四氯化碳等鹵化烴類，氯苯、二氯苯等氯化芳香族 烴類’丙酮、甲基乙基酮等酮類，乙腈等腈類，醋酸乙酯 等酯類，N，N-二甲基甲醯胺、N，N-二甲基乙醯胺等醯胺類， 二甲亞®、1，3-二甲基-2-咪唑啉酮等惰性溶劑，該惰性溶 劑可單獨或2種以上混合使用。 本發明使用的鹼，例如：三乙胺、二異丙基乙胺、丨，8-一 〇Y 一環-[5·4·0]-7 -十·—烯、吡啶基等含氮有機鹼類，碳 酸鈉、碳酸鉀、碳酸氫鈉、氫氧化鈉、氫氧化鉀、氫化鈉、 金屬鈉等無機驗類，醋酸鈉、醋酸鉀等有機驗類，乙氧基 -27- 200404764 鈉、第三丁基鉀等醇化物。又，鹼的使用量由中和反應發 生之酸的量爲佳，過量使用亦可。 本發明中的莫耳反應，各反應劑以等莫耳使用爲佳， 各反應劑亦可過量使用。反應溫度係於-2 0 °C乃至使用惰 性溶劑的迴流溫度下進行。反應時間由於反應規模、反應 溫度而沒有一定，可於數分至48小時之範圍內適當選擇。 反應終了後’根據含有標的的物之反應系以習知方法 單獨分離標的物’視需要地以再結晶法、蒸餾法、矽膠管 柱層析法等純化而製造標的物。又，亦可不單獨分離本反 應終了後之標的物，以提供後續之反應。 (1-4) 通式（1-1)~> 通式（1-2) 本反應係按照（1-3)而進行。 反應終了後，根據含有標的的物之反應系以習知方法 單獨分離標的物，視需要地以再結晶法、蒸餾法、矽膠管 柱層析法等純化而製造標的物。又，亦可不單獨分離本反 應終了後之標的物，以提供後續之反應。 (1-5) 通式（1-1)或通式（1-2)—通式（1-3) 本發明視需要地於觸媒量酸存在下反應。 惰性觸媒中，以顯著地不阻害本反應進行者爲佳，例 如：甲醇、乙醇、正丙醇等醇類，二乙胺、四氫呋喃、二 噚烷等鏈狀或環狀醚類，苯、甲苯、二甲苯等芳香族烴類， 氯苯、二氯苯等氯化芳香族烴類，此等惰性溶劑可單獨或 2種以上混合使用。 本反應所使用的酸例如爲：甲酸、醋酸、丙酸等有機 -28- 200404764 酸類，鹽酸、硫酸等無機酸類。 本發明中的莫耳反應，各反應劑以等莫耳使用爲佳’ 各反應劑亦可過量使用。反應溫度係於-2 0 °C乃至使用情 性溶劑的迴流溫度下進行。反應時間由於反應規模、反應 溫度而沒有一定，可於數分至4 8小時之範圍內適當選擇。 反應終了後，根據含有標的的物之反應系以習知方法 單獨分離標的物，視需要地以再結晶法、蒸餾法、矽膠管 柱層析法等純化而製造標的物。 製造方法2Manufactured to its standards. The heterocyclic system represented by QH is in accordance with International Patent Publication No. WO 9 1-3470, J. Chem · Soc. Perkin Trans · 1, 22, 2644 (1973), Kokai Hei 9-100271, Liebigs Annalen der Chemie, 675, 1 80 (1 964), J. Chem. Soc. (C), 747 (1 967), USP 5 7 2 8 8 3 4, J. Heterocycl. Chem., 22, 409 (1985), JP 60-146879, JP 6-306061, JP 63-41466, DokladyAkademii Nauk SSSR (Dokl. Akad. Nauk SSSR), 158, 1 3 5 8 (1 964), W098 -11079 Gong Xinggen, Drug Research (Drug res ·), (1), 189 (1968), J. Heterocycl. Chem., 15 (7), 1 2 3 1 (1 97 8), J. Chem. Soc Perkin Trans. 2, 1 670 (1 979), J. Am. Chem. Soc ·, 80, 3908 (1958), Journal fuer Praktische Chemie, 311, 477 (1 969), Chemische Berichet, 88, 1 3 5 1 (1 95 5), etc., or manufactured according to the standard. Among the inert solvents used in this reaction, it is preferred that those who do not significantly obstruct the reaction, such as: diethyl ether, tetrahydrofuran, dioxane and other chain or cyclic ethers, benzene, toluene, xylene and other aromatic hydrocarbons Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, chlorinated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile, etc. Esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, and other amines, dimethyl arylene, 1,3-dimethyl-2 -imidazoline Inert solvents such as ketones and water can be used alone or as a mixture of two or more. The base used in the present invention is, for example, nitrogen-containing organic bases such as triethylamine, diisopropylethylamine, 1,8-diBYbicyclo- [5 · 4 · 0] -7-undecene, and pyridyl. Carbon-25-200404764 Sodium, potassium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, sodium hydride, sodium metal and other inorganic bases, organic bases such as sodium acetate and potassium acetate, sodium ethoxylate, Alcohols such as third butyl potassium. The amount of the base to be used is preferably the amount of the acid from which the neutralization reaction occurs, and an excessive amount may be used. Related mobile catalyst systems used in the present invention are, for example, quaternary ammonium salts such as tetra-n-butylammonium bromide and benzyltriethylammonium bromide, and cyclic ethers such as 18-cyclo-6-ether. The use amount of the relevant mobile catalyst is preferably selected from a range of 0 · 0 1 to 0 · 5 times relative to the compound of the general formula (III). In the Mohr reaction in the present invention, each of the reactants is preferably used in equal moles, and each of the reactants may be used in excess. The reaction temperature is between -20 ° C and the reflux temperature using an inert solvent. The reaction time is not constant due to the reaction scale and reaction temperature, and it can be appropriately selected within a range of several minutes to 48 hours. After completion of the reaction, the target is separated by conventional methods according to the reaction system containing the target, and if necessary, purified by recrystallization, distillation, silica gel column chromatography, or the like to produce the target. In addition, the target after the end of the reaction may not be separated separately to provide subsequent reactions. (1-2) General formula (III)-general formula (IV) The inert solvents used in this reaction are, for example, alcohols such as methanol and ethanol, ethers such as tetrahydrofuran and dioxane, and water. The inert solvent may be They can be used alone or in combination. The acidic aqueous solution used as the reducing agent shown below may also be an inert solvent. Examples of the telegenic agent used in this reaction are metals, acids, and metal-salts. Metals are, for example, iron, tin, and zinc, and acids are, for example, inorganic acids such as hydrochloric acid and sulfuric acid, organic acids such as acetic acid, and tin chloride. The salt is, for example, ammonium chloride-26-200404764. It is also possible to use a combination thereof. The amount of the reducing agent used is preferably 10 times the metal and 0.05-10 times the acid and salt relative to the compound of the general formula (III). The reaction temperature is preferably 0 to 150 ° C, and the reaction time is not necessarily limited due to the reaction scale, reaction temperature, etc., and is preferably in the range of several minutes to 48 hours. In addition, the reduction reaction may be performed by a contact hydrogen addition method in the presence of a catalyst, where the catalyst is, for example, palladium on carbon, platinum, or Raney nickel. After completion of the reaction, the target is separated by conventional methods according to the reaction system containing the target, and if necessary, purified by recrystallization, distillation, silica gel column chromatography, or the like to produce the target. In addition, the target after the end of the reaction may not be separated separately to provide subsequent reactions. (1-3) General formula (IV)-general formula (V) It is preferable that the inert solvent used in the present invention does not hinder the progress of the present invention, for example, diethylamine, tetrahydrofuran, dioxane and the like Or cyclic ethers, aromatic hydrocarbons such as benzene, toluene, xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc. Ketones such as methyl ethyl ketone, nitriles such as acetonitrile, esters such as ethyl acetate, amines such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl Sub-®, 1,3-dimethyl-2-imidazolinone, and other inert solvents. These inert solvents can be used alone or in combination of two or more. The base used in the present invention is, for example, nitrogen-containing organic bases such as triethylamine, diisopropylethylamine, 8-one-0Y monocyclic- [5 · 4 · 0] -7-decene, pyridyl Category, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, sodium hydride, sodium metal and other inorganic tests, sodium acetate, potassium acetate and other organic tests, ethoxy-27-200404764 sodium, Alcohols such as tributyl potassium. The amount of the base used is preferably the amount of the acid generated by the neutralization reaction, and an excessive amount may be used. In the Mohr reaction in the present invention, each of the reactants is preferably used in equal moles, and each of the reactants may be used in excess. The reaction is carried out at a temperature of -20 ° C or even a reflux temperature using an inert solvent. The reaction time is not constant due to the reaction scale and reaction temperature, and it can be appropriately selected within a range of several minutes to 48 hours. After completion of the reaction, 'the target is separated by conventional methods based on the reaction system containing the target', and the target is purified by recrystallization, distillation, silica gel column chromatography, etc., if necessary. In addition, the target after the end of the reaction may not be separated separately to provide subsequent reactions. (1-4) General formulae (1-1) to > General formula (1-2) This reaction is carried out in accordance with (1-3). After completion of the reaction, the target is separated by conventional methods according to the reaction system containing the target, and if necessary, purified by recrystallization, distillation, silica gel column chromatography, or the like to produce the target. In addition, the target after the end of the reaction may not be separated separately to provide subsequent reactions. (1-5) General formula (1-1) or general formula (1-2)-general formula (1-3) The present invention reacts in the presence of a catalyst amount of acid, if necessary. Among the inert catalysts, those that do not significantly hinder the progress of the reaction are preferred, for example: alcohols such as methanol, ethanol, n-propanol, chain or cyclic ethers such as diethylamine, tetrahydrofuran, dioxane, benzene, Aromatic hydrocarbons such as toluene and xylene, and chlorinated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene. These inert solvents can be used alone or in combination of two or more. The acids used in this reaction are, for example, organic -28-200404764 acids such as formic acid, acetic acid, and propionic acid, and inorganic acids such as hydrochloric acid and sulfuric acid. In the Mohr reaction in the present invention, it is preferred that the respective reactants are used in equal amounts. Each of the reactants may be used in excess. The reaction is carried out at a temperature of -2 ° C or even the reflux temperature of an organic solvent. The reaction time is not constant due to the reaction scale and reaction temperature, and it can be appropriately selected within a range of several minutes to 48 hours. After completion of the reaction, the target is separated by conventional methods according to the reaction system containing the target, and if necessary, purified by recrystallization, distillation, silica gel column chromatography, or the like to produce the target. Manufacturing method 2

R17 蠢I雜環R17 Heterocyclic

R1-S02(R2) (1-1) 或 (1-2) h2n-r3, h2n-0R4, H2N-NR5R6 kR1-S02 (R2) (1-1) or (1-2) h2n-r3, h2n-0R4, H2N-NR5R6 k

I 一 3) -29- 200404764 (式中，R1、R2、R2’、R3、r4、R5、r6、a、G，、L、 Q、X及m係如上所述。R17爲胺基、2 -羥乙胺基或肼基。） 起始物質如通式（V)表示之胺衍生物、2 —羥乙胺衍生 物或肼衍生物，係根據特開平8 - 1 5 1 3 6 4號、B u 11 · K 〇 r e a ηI-3) -29- 200404764 (wherein R1, R2, R2 ', R3, r4, R5, r6, a, G, L, Q, X and m are as described above. R17 is an amine group, 2 -Hydroxyethylamino or hydrazine.) Starting materials such as amine derivatives, 2-hydroxyethylamine derivatives, or hydrazine derivatives represented by general formula (V) are based on Japanese Patent Application Laid-Open No. 8-1 5 1 3 6 4 , B u 11 · K 〇rea η

Chem. Soc. 22(7)，761 〜764(200 1 )或 Synth. commun·，16(2)， 163〜167等記載之雜環合成法或按照化合物（ΙΠ)而製造， 該化合物可單獨分離或不單獨分離，與製造方法丨相同方 法而製造本發明化合物之通式（1-1)〜（1-3)。 起始物質係爲通式（V)表示之化合物，例如在jr.chem. Soc·，1800(1925)、J· Chem· Soc·，2348(1926)等記載之 製造方法或按照其標準而製造。 下列第1表至第13表係爲本發明通式（1〇表示之鹵院 磺醯苯胺衍生物之代表例，而不限制本發明者。再者，物 性係爲融點（°C)或折射率。 在下列表中，「Me」爲甲基，「Et」爲乙基，「Pr」爲 丙基，「Bu」爲丁基，「Pen」爲戊基，「Hex」爲己基，「Ph」 爲苯基，「Pyn」爲吡啶基，「Pym」爲嘧啶基，「Pyd」爲 畊嗒基，「Ac」爲乙醯基，「η-」爲正，「i-」爲異，「s-」 爲第二，「t-」爲第三，「c-」脂環通式烴基。 「取代位置」係爲鹵烷磺醯胺基的取代位置。 -30- 200404764 通式（I — 4 )Chem. Soc. 22 (7), 761 to 764 (200 1) or Synth. Commun ·, 16 (2), 163 to 167, etc., or produced according to the heterocyclic synthesis method, or according to compound (IΠ). The general formulae (1-1) to (1-3) of the compound of the present invention can be produced by the same method as the production method 丨 with or without isolation. The starting material is a compound represented by the general formula (V). For example, the production method described in jr.chem. Soc ·, 1800 (1925), J · Chem · Soc ·, 2348 (1926), or the like is produced according to the standard. . The following Tables 1 to 13 are representative examples of the halogenated sulfanilide derivatives represented by the general formula (10) of the present invention, without limiting the present inventors. Furthermore, the physical properties are melting point (° C) or In the table below, "Me" is methyl, "Et" is ethyl, "Pr" is propyl, "Bu" is butyl, "Pen" is pentyl, "Hex" is hexyl, and "Ph "Is phenyl," Pyn "is pyridyl," Pym "is pyrimidinyl," Pyd "is glutaryl," Ac "is ethynyl," η- "is positive, and" i- "is iso, "s-" is the second, "t-" is the third, and "c-" is a cycloaliphatic hydrocarbon group. "Substitution position" is the substitution position of the halosulfonamido group. -30- 200404764 General formula (I — 4)

第1表（m=〇 ' A=- ch2 -' Gl=0 、J4=N) No. 取代 位置 Rl R2 X J5 R9 物性 〔融點（°C)〕 1-1 2 cf3 H H CH Me 1-2 2 cf3 H H CH Et 87-88 1-3 2 cf3 H H CH n-Pr 1-4 2 cf3 H H CH i-Pr 1-5 2 cf3 H H CH c-Pr 1-6 2 cf3 H H CH n-Bu 1-7 2 cf3 H H CH t-Bu 1-8 2 cf3 H H CH -CH2-Ph 130-132 1-9 2 cf3 H H CH -CH,-(2-Cl-Ph) 1-10 2 cf3 H H CH -CH7-(3-Cl-Ph) Ml 2 cf3 H H CH -CH7-(4-Cl-Ph) 1-12 2 cf3 H H CH -CH2-(2,6-ClrPh) 1-13 2 cf3 H H CH -CHMe-Ph 1-14 2 cf3 H H CH -CHMe-(2-Cl-Ph) 1-15 2 cf3 H H CH -CHMe-(3-Cl-Ph) 1-16 2 cf3 H H CH -CHMe-(4-Cl-Ph) M7 2 cf3 H H CH -CHMe-(2,6-ClrPh) 1-18 2 cf3 H H CH -CMe9-Ph 1-19 2 cf3 H H CH -CMe7-(2-Cl-Ph) 1-20 2 cf3 H H CH -CMe，-(3-Cl-Ph) 1-21 2 cf3 H H CH -CMe?-(4-Cl-Ph) 1-22 2 cf3 H H CH -CMe2-(2,6-Cl7-Ph) 1-23 2 cf3 H H CH Ph 141-142 1-24 2 cf3 H H CH 2-F-Ph 1-25 2 cf3 H H CH 3-F-Ph 1-26 2 cf3 H H CH 4-F-Ph 1-27 2 cf3 H H CH 2-Cl-Ph 129-131 1-28 2 cf3 H H CH 3-Cl-Ph 133-135 1-29 2 cf3 H H CH 4-Cl-Ph 171.8 1-30 2 cf3 H H CH 2-Br-Ph 128-130 1-31 2 CF, H H CH 3-Br-PhTable 1 (m = 〇 'A =-ch2-' Gl = 0, J4 = N) No. Substitution position Rl R2 X J5 R9 Physical properties [melting point (° C)] 1-1 2 cf3 HH CH Me 1- 2 2 cf3 HH CH Et 87-88 1-3 2 cf3 HH CH n-Pr 1-4 2 cf3 HH CH i-Pr 1-5 2 cf3 HH CH c-Pr 1-6 2 cf3 HH CH n-Bu 1 -7 2 cf3 HH CH t-Bu 1-8 2 cf3 HH CH -CH2-Ph 130-132 1-9 2 cf3 HH CH -CH,-(2-Cl-Ph) 1-10 2 cf3 HH CH -CH7 -(3-Cl-Ph) Ml 2 cf3 HH CH -CH7- (4-Cl-Ph) 1-12 2 cf3 HH CH -CH2- (2,6-ClrPh) 1-13 2 cf3 HH CH -CHMe- Ph 1-14 2 cf3 HH CH -CHMe- (2-Cl-Ph) 1-15 2 cf3 HH CH -CHMe- (3-Cl-Ph) 1-16 2 cf3 HH CH -CHMe- (4-Cl- Ph) M7 2 cf3 HH CH -CHMe- (2,6-ClrPh) 1-18 2 cf3 HH CH -CMe9-Ph 1-19 2 cf3 HH CH -CMe7- (2-Cl-Ph) 1-20 2 cf3 HH CH -CMe,-(3-Cl-Ph) 1-21 2 cf3 HH CH -CMe?-(4-Cl-Ph) 1-22 2 cf3 HH CH -CMe2- (2,6-Cl7-Ph) 1-23 2 cf3 HH CH Ph 141-142 1-24 2 cf3 HH CH 2-F-Ph 1-25 2 cf3 HH CH 3-F-Ph 1-26 2 cf3 HH CH 4-F-Ph 1-27 2 cf3 HH CH 2-Cl-Ph 129-131 1-28 2 cf3 HH CH 3-Cl-Ph 133-135 1-29 2 cf3 HH CH 4- Cl-Ph 171.8 1-30 2 cf3 H H CH 2-Br-Ph 128-130 1-31 2 CF, H H CH 3-Br-Ph

200404764 第1表（續) No· 取代 位置 R1 R2 X J5 R9 物性 〔融點（°C)〕 1-32 2 cf3 H H CH 4-Br-Ph 145-147 1-33 2 cf3 H H CH 2-I-Ph 1-34 2 cf3 H H CH 3-I-Ph 1-35 2 cf3 H H CH 4-I-Ph 1-36 2 cf3 H H CH 2-Me-Ph 51-53 1-37 2 cf3 H H CH 3-Me-Ph 1-38 2 cf3 H H CH 4-Me-Ph 154-156 1-39 2 cf3 H H CH 2-Et-Ph 1-40 2 cf3 H H CH 2 - i-Pr-Ph 48-50 1-41 2 cf3 H H CH 2-OMe-Ph 140.6 1-42 2 cf3 H H CH 3-OMe-Ph 1-43 2 cf3 H H CH 4-OMe-Ph 176-178 1-44 2 cf3 H H CH 2-SMe-Ph 125.8 1-45 2 cf3 H H CH 3-SMe-Ph 1-46 2 cf3 H H CH 4-SMe-Ph 1-47 2 cf3 H H CH 2-SOMe-Ph 50-52 1-48 2 cf3 H H CH 3-SOMe-Ph 1-49 2 cf3 H H CH 4-SOMe-Ph 1-50 2 cf3 H H CH 2-SO?Me-Ph 165-167 1-51 2 cf3 H H CH 3-SO^Me-Ph 1-52 2 cf3 H H CH 4-SO;Me-Ph 1-53 2 cf3 H H CH 2-NCVPh 1-54 2 cf3 H H CH 3-NOrPh 1-55 2 cf3 H H CH 4-N07-Ph 1-56 2 cf3 H H CH 2-CN-Ph 1-57 2 cf3 H H CH 3>CN-Ph 1-58 2 cf3 H H CH 4-CN-Ph 1-59 2 cf3 H H CH 2-CF3-Ph 123-125 1-60 2 cf3 H H CH 3-CF3-Ph 1-61 2 cf3 H H CH 4-CF3-Ph 1-62 2 cf3 H H CH 2-OCF3-Ph 1-63 2 cf3 H H CH 3-OCF3-Ph 1-64 2 cf3 H H CH 4>OCF3-Ph 1-65 2 cf3 H H CH 2-SCF3-Ph 1-66 2 cf3 H H CH 3-SCF3-Ph 1-67 2 cf3 H H CH 4-SCF3-Ph 1-68 2 cf3 H H CH 2-SOCF3-Ph 1-69 2 cf3 H H CH 3-SOCF3-Ph 1-70 2 cf3 H H CH 4-SOCF3-Ph 1-71 2 cf3 H H CH 2-S07CF3-Ph 1-72 2 CF, H H CH 3-SO;CFrPh200404764 Table 1 (continued) No. Substitution position R1 R2 X J5 R9 Physical properties [melting point (° C)] 1-32 2 cf3 HH CH 4-Br-Ph 145-147 1-33 2 cf3 HH CH 2-I -Ph 1-34 2 cf3 HH CH 3-I-Ph 1-35 2 cf3 HH CH 4-I-Ph 1-36 2 cf3 HH CH 2-Me-Ph 51-53 1-37 2 cf3 HH CH 3- Me-Ph 1-38 2 cf3 HH CH 4-Me-Ph 154-156 1-39 2 cf3 HH CH 2-Et-Ph 1-40 2 cf3 HH CH 2-i-Pr-Ph 48-50 1-41 2 cf3 HH CH 2-OMe-Ph 140.6 1-42 2 cf3 HH CH 3-OMe-Ph 1-43 2 cf3 HH CH 4-OMe-Ph 176-178 1-44 2 cf3 HH CH 2-SMe-Ph 125.8 1-45 2 cf3 HH CH 3-SMe-Ph 1-46 2 cf3 HH CH 4-SMe-Ph 1-47 2 cf3 HH CH 2-SOMe-Ph 50-52 1-48 2 cf3 HH CH 3-SOMe- Ph 1-49 2 cf3 HH CH 4-SOMe-Ph 1-50 2 cf3 HH CH 2-SO? Me-Ph 165-167 1-51 2 cf3 HH CH 3-SO ^ Me-Ph 1-52 2 cf3 HH CH 4-SO; Me-Ph 1-53 2 cf3 HH CH 2-NCVPh 1-54 2 cf3 HH CH 3-NOrPh 1-55 2 cf3 HH CH 4-N07-Ph 1-56 2 cf3 HH CH 2-CN -Ph 1-57 2 cf3 HH CH 3 > CN-Ph 1-58 2 cf3 HH CH 4-CN-Ph 1-59 2 cf3 HH CH 2-CF3-Ph 123-125 1-60 2 cf3 HH CH 3- CF3-Ph 1-61 2 cf3 H H CH 4-CF3-Ph 1-62 2 cf3 HH CH 2-OCF3-Ph 1-63 2 cf3 HH CH 3-OCF3-Ph 1-64 2 cf3 HH CH 4 > OCF3-Ph 1-65 2 cf3 HH CH 2-SCF3-Ph 1-66 2 cf3 HH CH 3-SCF3-Ph 1-67 2 cf3 HH CH 4-SCF3-Ph 1-68 2 cf3 HH CH 2-SOCF3-Ph 1-69 2 cf3 HH CH 3- SOCF3-Ph 1-70 2 cf3 HH CH 4-SOCF3-Ph 1-71 2 cf3 HH CH 2-S07CF3-Ph 1-72 2 CF, HH CH 3-SO; CFrPh

-32- 200404764 第1表（續)-32- 200404764 Table 1 (Continued)

No. 取代 位置 R1 R2 X J5 R9 物性 〔融點ΓΟ〕 1-73 2 cf3 H H CH 4-S02CF3-Ph 1-74 2 cf3 H H CH 2-C09H-Ph 1-75 2 cf3 H H CH 3-CO?H-Ph 1-76 2 cf3 H H CH 4-CO，H-Ph 1-77 2 cf3 H H CH 2-C02Me-Ph 1-78 2 cf3 H H CH 3-C09Me-Ph 1-79 2 cf3 H H CH 4-C07Me-Ph 1-80 2 cf3 H H CH 2-Ph-]Ph 1-81 2 cf3 H H CH 4-PhO-Ph 44-46 1-82 2 cf3 H H CH 2,4-F2-Ph 1-83 2 cf3 H H CH 2,6-F，-Ph 1-84 2 cf3 H H CH 2,3-Cl2-Ph 140-142 1-85 2 cf3 H H CH 2,6-ClrPh 1-86 2 cf3 H H CH 2,6-Br9-Ph 1-87 2 cf3 H H CH 2,6-I2-Ph 1-88 2 cf3 H H CH 2-Me-3-Cl-Ph 136-137 1-89 2 cf3 H H CH 2-Me-4-Br-Ph 174-176 1-90 2 cf3 H H CH 3-Me-4-Br-Ph 136-138 1-91 2 cf3 H H CH 2,3-MerPh 66-68 1-92 2 cf3 H H CH 2,6-MerPh 193-195 1-93 2 cf3 H H CH 2,3-(CH2)4-Ph 127-128 1-94 2 cf3 H H CH 2,6-Evfh 126-128 1-95 2 cf3 H H CH 2-Me-4-OMe-Ph 154-15.6 1-96 2 cf3 H H CH 2,3-(OMe)2-Ph 1-97 2 cf3 H H CH 2,6-(OMe)?-Ph 1-98 2 cf3 H H CH 2,4-(CF3)，;Ph 1-99 2 cf3 H H CH 2,6-(CF3)2-Ph 1-100 2 cf3 H H CH 2,6-(OCF3VPh 1-101 2 cf3 H H CH 2-Cl-6-F-Ph 1-102 2 cf3 H H CH 2-Cl-6-Me-Ph 154-155 1-103 2 cf3 H H CH 2,3,4-ClrPh 166-168 1-104 2 cf3 H H CH 2,4,6-ClrPh 1-105 2 cf3 H H CH 2,6-Cl2-4-CF3-Ph 1-106 2 cf3 H H CH 2,6-Cl2-4-OCFrPh 1-107 2 cf3 H H CH 2,4,6-Me3-Ph 193-195 1-108 2 cf3 H H CH 2-Pyn 104-106 1-109 2 cf3 H H CH 3-Pyn 1-110 2 cf3 H H CH 4-Pyn 1-111 2 cf3 H H CH 6-Cl-2-Pyn 1-112 2 cf3 H H CH 5-CF3-2-Pyn 56-58 1-113 2 CF, H H CH 6-CF,-2-Pyn 200404764 第1表（續）No. Substitution position R1 R2 X J5 R9 Physical properties [melting point ΓΟ] 1-73 2 cf3 HH CH 4-S02CF3-Ph 1-74 2 cf3 HH CH 2-C09H-Ph 1-75 2 cf3 HH CH 3-CO? H-Ph 1-76 2 cf3 HH CH 4-CO, H-Ph 1-77 2 cf3 HH CH 2-C02Me-Ph 1-78 2 cf3 HH CH 3-C09Me-Ph 1-79 2 cf3 HH CH 4- C07Me-Ph 1-80 2 cf3 HH CH 2-Ph-] Ph 1-81 2 cf3 HH CH 4-PhO-Ph 44-46 1-82 2 cf3 HH CH 2,4-F2-Ph 1-83 2 cf3 HH CH 2,6-F, -Ph 1-84 2 cf3 HH CH 2,3-Cl2-Ph 140-142 1-85 2 cf3 HH CH 2,6-ClrPh 1-86 2 cf3 HH CH 2,6- Br9-Ph 1-87 2 cf3 HH CH 2,6-I2-Ph 1-88 2 cf3 HH CH 2-Me-3-Cl-Ph 136-137 1-89 2 cf3 HH CH 2-Me-4-Br -Ph 174-176 1-90 2 cf3 HH CH 3-Me-4-Br-Ph 136-138 1-91 2 cf3 HH CH 2,3-MerPh 66-68 1-92 2 cf3 HH CH 2,6- MerPh 193-195 1-93 2 cf3 HH CH 2,3- (CH2) 4-Ph 127-128 1-94 2 cf3 HH CH 2,6-Evfh 126-128 1-95 2 cf3 HH CH 2-Me- 4-OMe-Ph 154-15.6 1-96 2 cf3 HH CH 2,3- (OMe) 2-Ph 1-97 2 cf3 HH CH 2,6- (OMe)?-Ph 1-98 2 cf3 HH CH 2 , 4- (CF3) ,; Ph 1-99 2 cf3 HH CH 2,6- (CF3) 2-Ph 1-100 2 cf3 HH CH 2,6- (OCF3VPh 1-101 2 cf3 HH CH 2-Cl-6-F-Ph 1-102 2 cf3 HH CH 2-Cl-6-Me-Ph 154-155 1-103 2 cf3 HH CH 2,3,4- ClrPh 166-168 1-104 2 cf3 HH CH 2,4,6-ClrPh 1-105 2 cf3 HH CH 2,6-Cl2-4-CF3-Ph 1-106 2 cf3 HH CH 2,6-Cl2-4 -OCFrPh 1-107 2 cf3 HH CH 2,4,6-Me3-Ph 193-195 1-108 2 cf3 HH CH 2-Pyn 104-106 1-109 2 cf3 HH CH 3-Pyn 1-110 2 cf3 HH CH 4-Pyn 1-111 2 cf3 HH CH 6-Cl-2-Pyn 1-112 2 cf3 HH CH 5-CF3-2-Pyn 56-58 1-113 2 CF, HH CH 6-CF, -2- Pyn 200404764 Form 1 (Continued)

No. 取代位置 R1 R2No. Replacement position R1 R2

X J5 R9 物性〔融點（°C)、折射率〕 1-114 2 1-115 2 1-116 2 M17 2 1-118 2 1-119 2 1-120 2 1-121 2 1-122 2 1-123 2 1-124 2 1-125 2 1-126 2 1-127 2 1-128 2 1-129 2 1-130 2 1-131 2 1-132 2 1-133 2 1-134 2 1-135 2 1-136 2 1-137 2 1-138 2 1-139 2 1-140 2 1-141 2 M42 2 M43 2 1-144 2 M45 2 1-146 2 M47 2 1-148 2 1-149 2 M50 2 1-151 2 1-152 2 1-153 2 333333333 3 3 FFFFFFFFFFF cccccccccccX J5 R9 Physical properties [melting point (° C), refractive index] 1-114 2 1-115 2 1-116 2 M17 2 1-118 2 1-119 2 1-120 2 1-121 2 1-122 2 1 -123 2 1-124 2 1-125 2 1-126 2 1-127 2 1-128 2 1-129 2 1-130 2 1-131 2 1-132 2 1-133 2 1-134 2 1-135 2 1-136 2 1-137 2 1-138 2 1-139 2 1-140 2 1-141 2 M42 2 M43 2 1-144 2 M45 2 1-146 2 M47 2 1-148 2 1-149 2 M50 2 1-151 2 1-152 2 1-153 2 333333333 3 3 FFFFFFFFFFF ccccccccccc

Jx Jx ί Jx Tu Jx JX ΤΓ ΤΓ ΤΓ ΤΓΤΓΤΓΤΓίχτΓΤΓ- XT cf3 H cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 COMe cf3 COMe cf3 COMe cf3 COMe cf3 COMe cf3 COMe cf3 COMe cf3 COMe cf3 C02Me cf3 C02Me cf3 CO;Me cf3 C02Me cf3 CO，Me cf3 CO;Me cf3 CO^Me cf3 C02Me cf3 so?cf3 cf3 so，cf3 cf3 so2cf3 CF, so9cf, H CH 6-Cl-4-CF3-2-Pyn H CH 2-Pym H CH 4-Pym H CH 4,6-Me2-2-Pym H CH 4,6-(OMe)?-2-Pym H CH 3-Pyd — H CH 6-Cl-3-Pyd H CH -CO-NHMe H CH -CO-NHPh H CH -CO-NMePh 1.5202(28〇C) H CH -CO-N(i-Pr) (2,4-FrPh) 183.5-184.4 H CH -CO-N(i-Pr)2 H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-Cl，-Ph H CH 2,6-Me2-Ph H CH -CH7-Ph H CH -CMe2-Ph H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-Cl2-Ph H CH 2,6-Me?-Ph H CH -CH?-Ph H CH -CMe,-Ph H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-ClrPh H CH 2,6-Me2-Ph H CH -CHrPh ΙΪ H CH •CMe，-Ph H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-PhJx Jx ί Jx Tu Jx JX ΤΓ ΤΓ ΤΓ ΤΓΤΓΤΓΤΓίχτΓΤΓ- XT cf3 H cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 Me cf3 COMe cf3 com3 com3 come cf3 COMe cf3 com C02Me cf3 CO; Me cf3 C02Me cf3 CO, Me cf3 CO; Me cf3 CO ^ Me cf3 C02Me cf3 so? Cf3 cf3 so, cf3 cf3 so2cf3 CF, so9cf, H CH 6-Cl-4-CF3-2-Pyn H CH 2-Pym H CH 4-Pym H CH 4,6-Me2-2-Pym H CH 4,6- (OMe)?-2-Pym H CH 3-Pyd — H CH 6-Cl-3-Pyd H CH -CO-NHMe H CH -CO-NHPh H CH -CO-NMePh 1.5202 (28 ° C) H CH -CO-N (i-Pr) (2,4-FrPh) 183.5-184.4 H CH -CO-N ( i-Pr) 2 H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-Cl, -Ph H CH 2,6-Me2-Ph H CH -CH7-Ph H CH -CMe2-Ph H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-Cl2-Ph H CH 2,6-Me ? -Ph H CH -CH? -Ph H CH -CMe, -Ph H CH Ph H CH 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph H CH 2,6-ClrPh H CH 2,6-Me2-Ph H CH -CHrPh ΙΪ H CH • CMe, -Ph H CH Ph HC H 2-Cl-Ph H CH 3-Cl-Ph H CH 4-Cl-Ph

-34- 200404764 第1表（續） Ν。· R1 R2-34- 200404764 Table 1 (continued) Ν. R1 R2

X J5 R9 物性 〔融點（°C)、折射率〕X J5 R9 Physical properties [Melting point (° C), refractive index]

1-154 2 cf3 so7cf3 1-155 2 cf3 so2cf3 1-156 2 cf3 so2cf3 1-157 2 cf3 so，cf3 1-158 2 cf3 H 1-159 2 cf3 H 1-160 2 cf3 H 1-161 2 cf3 H 1-162 2 cf3 H 1-163 2 cf3 H 1-164 2 cf3 H 1-165 2 cf3 H 1-166 2 cf3 H 1-167 2 cf3 H 1-168 2 cf3 H 1-169 2 cf3 H 1-170 2 cf3 H 1-171 2 cf3 H 1-172 2 cf3 H 1-173 2 cf3 H 1-174 2 cf3 H 1-175 2 cf3 H 1-176 2 cf3 H 1-177 2 cf3 H 1-178 2 cf3 H 1-179 2 cf3 H 1-180 2 cf3 H 1-181 2 cf3 H 1-182 2 cf3 H 1-183 2 cf3 H 1-184 2 cf3 H 1-185 2 cf3 H 1-186 2 cf3 H 1-187 2 cf3 H 1-188 2 cf3 H 1-189 2 cf3 H 1-190 2 cf3 H 1-191 2 cf3 H 1-192 2 cf3 H 1-193 2 cf3 H 1-194 2 CF, H HHHH-c-c-c-cl-c-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-αΗΗΗΗΗΗΗΗΗΗΗΗΗ 444444444444555555555555 CH 2,6-Cl2-Ph CH 2,6-Me，-Ph CH -CH7-Ph CH -CMe，-Ph CH Ph CH 2-Cl-Ph CH 3-Cl-Ph CH 4-Cl-Ph CH 2-Me-Ph CH 2-CF3-Ph CH 2,6-Cl，-Ph CH 2,6-Me，-Ph 167-169 CH 2-Cl-6-F-Ph CH 2-Cl-6-Me-Ph CH -CH2-Ph CH -CMe2-Ph CH Ph CH 2-Cl-Ph CH 3-Cl-Ph CH 4-Cl-Ph CH 2-Me-Ph CH 2-CF3-Ph CH 2,6-Cl2-Ph CH 2,6-Me，-Ph 167-169 CH 2-Cl-6-F-Ph CH 2-Cl-6-Me-Ph CH -CH，-Ph CH -CMerPh C-Me Me C-Me Et 89.1 C-Me n-Pr C-Me i-Pr C-Me c-Pr C-Me n-Bu C-Me t-Bu C-Me c-Hex 52-54 C-Me -CH7-Ph 43-45 C-Me -CMe2-Ph C-Me Ph 1.5476(23〇C) C-Me 2-Cl-Ph 51-53 C-Me 3-Cl-Ph -35- 200404764 第1表（續) No. 取代 位置 R1 R2 X J5 R9 物性 〔融點（。〇〕 1-195 2 cf3 H H C-Me 4-Cl-Ph 1-196 2 cf3 H H C-Me 2-Me-Ph 1-197 2 cf3 H H C-Me 2-CF3-Ph 1-198 2 cf3 H H C-Me 2,6-Cl，-Ph 186-188 1-199 2 cf3 H H C-Me 2,6-Me?-Ph 191-193 1-200 2 cf3 H H C-Me 2-Cl-6-F-Ph 1-201 2 cf3 H H C-Me 2-Cl-6-Me-Ph 1-202 2 cf3 H H C-Me 2-Pyn 1-203 2 cf3 H H C-Me 3-Pyn 1-204 2 cf3 H H C-Me 4-Pyn 1-205 2 cf3 H H C-Me 6-Cl-2-Pyn 1-206 2 cf3 H H C-Me 5-CF3-2-Pyn 1-207 2 cf3 H H C-Me 6-CF3-2-Pyn 1-208 2 cf3 H H C-Me 6-Cl-4-CF3-2-Pyn 1-209 2 cf3 H H C-Me 2-Pym 1-210 2 cf3 H H C-Me 2-Pym 1-211 2 cf3 H H C-Me 4,6-Me2-2-Pym 1-212 2 cf3 H H C-Me 4,6-(OMe)7-2-Pym 1-213 2 cf3 H H C-Me 3-Pyd _ 1-214 2 cf3 H H C-Me 6-Cl-3-Pyd 1-215 2 cf3 H H c-cf3 Me 78.3-84.7 1-216 2 cf3 H H c-cf3 t-Bu 1-217 2 cf3 H H c-cf3 -CH,-Ph 1-218 2 cf3 H H c-cf3 -CMe 广 Ph 1-219 2 cf3 H H c-cf3 Ph 1-220 2 cf3 H H c-cf3 2-Cl-Ph 1-221 2 cf3 H H c-cf3 3-Cl-Ph 1-222 2 cf3 H H c-cf3 4-Cl-Ph 1-223 2 cf3 H H c-cf3 2-Me-Ph 1-224 2 cf3 H H c-cf3 2-CF3-Ph 1-225 2 cf3 H H c-cf3 2,6-Cl2-Ph 1-226 2 cf3 H H c-cf3 2,6-Me2-Ph 1-227 2 cf3 H H c-cf3 2-Cl-6-F-Ph 1-228 2 cf3 H H c-cf3 2-Cl-6-Me-Ph 1-229 2 cf3 H H C-Cl Me 1-230 2 cf3 H H C-Cl t-Bu 1-231 2 cf3 H H C-Cl -CH，-Ph 1-232 2 cf3 H H C-Cl -CMe,-Ph 1-233 2 cf3 H H C-Cl Ph 1-234 2 CF, H H C-Cl 2-Cl-Ph 200404764 第1表（續) No. 取代 位置 R1 R2 X J5 R9 物性 〔融點（°C)、折射率〕 1-235 2 cf3 H H C-Cl 3-Cl-Ph 1-236 2 cf3 H H C-Cl 4-Cl-Ph 1-237 2 cf3 H H C-Cl 2-Me-Ph 49-51 1-238 2 cf3 H H C-Cl 2-CF3-Ph 1-239 2 CF3 H H C-Cl 2,6-ClrPh 1-240 2 cf3 H H C-Cl 2,6-Me?-Ph 1-241 2 cf3 H H C-Cl 2-Cl-6-F-Ph 1-242 2 cf3 H H C-Cl 2-Cl-6-Me-Ph 1-243 2 cf3 H H C-Br Me 1-244 2 cf3 H H C-Br t-Bu 1-245 2 cf3 H H C-Br -CH，-Ph 45-48 1-246 2 cf3 H H C-Br -CMe7-Ph 1-247 2 cf3 H H C-Br Ph 1-248 2 cf3 H H C-Br 2-Cl-Ph 1-249 2 cf3 H H C-Br 3-Cl-Ph 1-250 2 cf3 H H C-Br 4-Cl-Ph 1-251 2 cf3 H H C-Br 2-Me-Ph 57-60 1-252 2 cf3 H H C-Br 2-CF3-Ph 1-253 2 cf3 H H C-Br 2,6-Cl2-Ph 1-254 2 cf3 H H C-Br 2,6-Me?-Ph 176-178 1-255 2 cf3 H H C-Br 2-Cl-6-F-Ph 1-256 2 cf3 H H C-Br 2-Cl-6-Me-Ph 1-257 2 cf3 H H C-OMe Ph NMR-1 1-258 2 cf3 H H C-OMe 2-Cl-Ph 48-50 1-259 2 cf3 H H C-OMe 3-Cl-Ph 1-260 2 cf3 H H C-OMe 4-Cl-Ph 1-261 2 cf3 H H C-OMe 2,6-ClrPh 1-262 2 cf3 H H C-OMe 2,6-Me,-Ph 1-263 2 cf3 H H C-OMe 2-Cl-6-F-Ph 1-264 2 cf3 H H C-OMe 2-Cl-6-Me-Ph 1-265 2 cf3 H H C-SMe Ph 1.5518(23°〇 1-266 2 cf3 H H C-SMe 2-Cl-Ph 58-60 1-267 2 cf3 H H C-SMe 3-Cl-Ph 1-268 2 cf3 H H C-SMe 4-Cl-Ph 121-123 1-269 2 cf3 H H C-SMe 2,6-ClrPh 1-270 2 cf3 H H C-SMe 2,6-Me，-Ph 1-271 2 cf3 H H C-SMe 2-Cl-6-F-Ph 1-272 2 cf3 H H C-SMe 2-Cl-6-Me-Ph 1-273 2 cf3 H H c-schf2 Ph 49-51 1-274 2 cf3 H H c-schf7 2-Cl-Ph 1-275 2 CF, H H C-SCHF? 3-Cl-Ph 200404764 第1表（續) No. 取代 位置 R1 R2 X J5 R9 物性 〔融點（°C)〕 1-276 2 cf3 H H c-schf2 4-Cl-Ph 1-277 2 cf3 H H C-SCHF, 256-Cl,-Ph 1-278 2 cf3 H H c-schf7 2,6-MerPh 1-279 2 cf3 H H C-SOMe Ph 69-71 1-280 2 cf3 H H C-SOMe 2-Cl-Ph 1-281 2 cf3 H H C-SOMe 3-Cl-Ph 1-282 2 cf3 H H C-SOMe 4-Cl-Ph 149-150 1-283 2 cf3 H H C-SOMe 2,6-Cl7-Ph 1-284 2 cf3 H H C-SOMe 2,6-Me?-Ph 1-285 2 cf3 H H C-S02Mc Ph 70-72 1-286 2 cf3 H H C-S02Me 2-Cl-Ph 154-156 1-287 2 cf3 H H C-S02Me 3-Cl-Ph 1-288 2 cf3 H H C-SO?Me 4-Cl-Ph 141-143 1-289 2 CF3 H H C-SO?Me 2,6-Cl?-Ph 1-290 2 cf3 H H C-S02Me 2,6-Me，-Ph 1-291 2 cf3 H H C-Ph Et 142-144 1-292 2 cf3 H H C-Ph Ph 159-160 1-293 2 cf3 H H C-Ph 2,6-Cl,-Ph 1-294 2 cf3 H H C-Ph 256-Me2-Ph 1-295 3 cf3 H H CH Me 1-296 3 cf3 H H CH t-Bu 1-297 3 cf3 H H CH -CH?-Ph 1-298 3 cf3 H H CH -CMe2-Ph 1-299 3 cf3 H H CH Ph 1-300 3 cf3 H H CH 2-Cl-Ph 1-301 3 cf3 H H CH 3-Cl-Ph 1-302 3 cf3 H H CH 4-Cl-Ph 1-303 3 cf3 H H CH 2-Me-Ph 1-304 3 cf3 H H CH 2-CF3-Ph 1-305 3 cf3 H H CH 2,6-ClrPh 1-306 3 cf3 H H CH 2,6-MerPh 1-307 3 cf3 H H CH 2-Cl-6-F-Ph 1-308 3 cf3 H H CH 2-Cl-6-Me-Ph 1-309 4 cf3 H H CH Me 1-310 4 cf3 H H CH t-Bu 1-311 4 cf3 H H CH -CH7-Ph 1-312 4 cf3 H H CH -CMe，-Ph 1-313 4 cf3 H H CH Ph 1-314 4 cf3 H H CH 2-Cl-Ph 1-315 4 cf3 H H CH 3-Cl-Ph 1-316 4 cf3 H H CH 4-Cl-Ph 200404764 第1表（續）1-154 2 cf3 so7cf3 1-155 2 cf3 so2cf3 1-156 2 cf3 so2cf3 1-157 2 cf3 so, cf3 1-158 2 cf3 H 1-159 2 cf3 H 1-160 2 cf3 H 1-161 2 cf3 H 1-162 2 cf3 H 1-163 2 cf3 H 1-164 2 cf3 H 1-165 2 cf3 H 1-166 2 cf3 H 1-167 2 cf3 H 1-168 2 cf3 H 1-169 2 cf3 H 1- 170 2 cf3 H 1-171 2 cf3 H 1-172 2 cf3 H 1-173 2 cf3 H 1-174 2 cf3 H 1-175 2 cf3 H 1-176 2 cf3 H 1-177 2 cf3 H 1-178 2 cf3 H 1-179 2 cf3 H 1-180 2 cf3 H 1-181 2 cf3 H 1-182 2 cf3 H 1-183 2 cf3 H 1-184 2 cf3 H 1-185 2 cf3 H 1-186 2 cf3 H 1-187 2 cf3 H 1-188 2 cf3 H 1-189 2 cf3 H 1-190 2 cf3 H 1-191 2 cf3 H 1-192 2 cf3 H 1-193 2 cf3 H 1-194 2 CF, H HHHH -ccc-cl-c-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-cl-αΗΗΗΗΗΗΗΗΗΗΗΗΗ 444444444444555555555555 CH 2,6- Cl2-Ph CH 2,6-Me, -Ph CH -CH7-Ph CH -CMe, -Ph CH Ph CH 2-Cl-Ph CH 3-Cl-Ph CH 4-Cl-Ph CH 2-Me-Ph CH 2-CF3-Ph CH 2,6-Cl, -Ph CH 2,6-Me, -Ph 167-169 CH 2-Cl-6-F-Ph CH 2-Cl-6-Me-Ph CH -CH2- Ph CH -CMe2-Ph CH Ph CH 2-Cl-Ph CH 3-Cl-Ph CH 4-Cl-Ph CH 2-Me-Ph CH 2-CF3-Ph CH 2,6-Cl2-Ph CH 2,6-Me, -Ph 167 -169 CH 2-Cl-6-F-Ph CH 2-Cl-6-Me-Ph CH -CH, -Ph CH -CMerPh C-Me Me C-Me Et 89.1 C-Me n-Pr C-Me i -Pr C-Me c-Pr C-Me n-Bu C-Me t-Bu C-Me c-Hex 52-54 C-Me -CH7-Ph 43-45 C-Me -CMe2-Ph C-Me Ph 1.5476 (23〇C) C-Me 2-Cl-Ph 51-53 C-Me 3-Cl-Ph -35- 200404764 Table 1 (continued) No. Substituted position R1 R2 X J5 R9 Properties [melting point (. 〇] 1-195 2 cf3 HH C-Me 4-Cl-Ph 1-196 2 cf3 HH C-Me 2-Me-Ph 1-197 2 cf3 HH C-Me 2-CF3-Ph 1-198 2 cf3 HH C-Me 2,6-Cl, -Ph 186-188 1-199 2 cf3 HH C-Me 2,6-Me? -Ph 191-193 1-200 2 cf3 HH C-Me 2-Cl-6-F -Ph 1-201 2 cf3 HH C-Me 2-Cl-6-Me-Ph 1-202 2 cf3 HH C-Me 2-Pyn 1-203 2 cf3 HH C-Me 3-Pyn 1-204 2 cf3 HH C-Me 4-Pyn 1-205 2 cf3 HH C-Me 6-Cl-2-Pyn 1-206 2 cf3 HH C-Me 5-CF3-2-Pyn 1-207 2 cf3 HH C-Me 6-CF3 -2-Pyn 1-208 2 cf3 HH C-Me 6-Cl-4-CF3-2-Pyn 1-209 2 cf3 HH C-Me 2-Pym 1-210 2 cf3 HH C-Me 2-Pym 1- 211 2 cf3 HH C-Me 4,6-Me2-2-Pym 1-212 2 cf3 HH C-Me 4,6- (OMe) 7-2-Pym 1-213 2 cf3 HH C-Me 3-Pyd _ 1-214 2 cf3 HH C-Me 6-Cl-3-Pyd 1-215 2 cf3 HH c-cf3 Me 78.3-84.7 1-216 2 cf3 HH c-cf3 t-Bu 1-217 2 cf3 HH c-cf3 -CH, -Ph 1-218 2 cf3 HH c-cf3 -CMe Guang Ph 1-219 2 cf3 HH c-cf3 Ph 1-220 2 cf3 HH c-cf3 2-Cl-Ph 1-221 2 cf3 HH c- cf3 3-Cl-Ph 1-222 2 cf3 HH c-cf3 4-Cl-Ph 1-223 2 cf3 HH c-cf3 2-Me-Ph 1-224 2 cf3 HH c-cf3 2- CF3-Ph 1-225 2 cf3 HH c-cf3 2,6-Cl2-Ph 1-226 2 cf3 HH c-cf3 2,6-Me2-Ph 1-227 2 cf3 HH c-cf3 2-Cl-6- F-Ph 1-228 2 cf3 HH c-cf3 2-Cl-6-Me-Ph 1-229 2 cf3 HH C-Cl Me 1-230 2 cf3 HH C-Cl t-Bu 1-231 2 cf3 HH C -Cl -CH, -Ph 1-232 2 cf3 HH C-Cl -CMe, -Ph 1-233 2 cf3 HH C-Cl Ph 1-234 2 CF, HH C-Cl 2-Cl-Ph 200404764 Table 1 (Continued) No. Substituted position R1 R2 X J5 R9 Physical properties [melting point (° C), refractive index] 1-235 2 cf3 HH C-Cl 3-Cl-Ph 1-236 2 cf3 HH C-Cl 4-Cl -Ph 1-237 2 cf3 HH C-Cl 2-Me-Ph 49-51 1-238 2 cf3 HH C-Cl 2-CF3-Ph 1-239 2 CF3 HH C-Cl 2,6-ClrPh 1-240 2 cf3 HH C-Cl 2,6-Me? -Ph 1-241 2 cf3 HH C-Cl 2-Cl-6-F-Ph 1-242 2 cf3 HH C-Cl 2-Cl-6-Me-Ph 1-243 2 cf3 HH C-Br Me 1-244 2 cf3 HH C-Br t-Bu 1-245 2 cf3 HH C-Br -CH, -Ph 45-48 1-246 2 cf3 HH C-Br -CMe7 -Ph 1-247 2 cf3 HH C-Br Ph 1-248 2 cf3 HH C-Br 2-Cl-Ph 1-249 2 cf3 HH C-Br 3-Cl-Ph 1-250 2 cf3 HH C-Br 4 -Cl-Ph 1-251 2 cf3 HH C-Br 2-Me-Ph 57-60 1-252 2 cf3 HH C-Br 2-CF3-P h 1-253 2 cf3 HH C-Br 2,6-Cl2-Ph 1-254 2 cf3 HH C-Br 2,6-Me? -Ph 176-178 1-255 2 cf3 HH C-Br 2-Cl- 6-F-Ph 1-256 2 cf3 HH C-Br 2-Cl-6-Me-Ph 1-257 2 cf3 HH C-OMe Ph NMR-1 1-258 2 cf3 HH C-OMe 2-Cl-Ph 48-50 1-259 2 cf3 HH C-OMe 3-Cl-Ph 1-260 2 cf3 HH C-OMe 4-Cl-Ph 1-261 2 cf3 HH C-OMe 2,6-ClrPh 1-262 2 cf3 HH C-OMe 2,6-Me, -Ph 1-263 2 cf3 HH C-OMe 2-Cl-6-F-Ph 1-264 2 cf3 HH C-OMe 2-Cl-6-Me-Ph 1- 265 2 cf3 HH C-SMe Ph 1.5518 (23 ° 〇1-266 2 cf3 HH C-SMe 2-Cl-Ph 58-60 1-267 2 cf3 HH C-SMe 3-Cl-Ph 1-268 2 cf3 HH C-SMe 4-Cl-Ph 121-123 1-269 2 cf3 HH C-SMe 2,6-ClrPh 1-270 2 cf3 HH C-SMe 2,6-Me, -Ph 1-271 2 cf3 HH C- SMe 2-Cl-6-F-Ph 1-272 2 cf3 HH C-SMe 2-Cl-6-Me-Ph 1-273 2 cf3 HH c-schf2 Ph 49-51 1-274 2 cf3 HH c-schf7 2-Cl-Ph 1-275 2 CF, HH C-SCHF? 3-Cl-Ph 200404764 Table 1 (continued) No. Substitution position R1 R2 X J5 R9 Physical properties [melting point (° C)] 1-276 2 cf3 HH c-schf2 4-Cl-Ph 1-277 2 cf3 HH C-SCHF, 256-Cl, -Ph 1-278 2 cf3 HH c-schf7 2,6-MerPh 1-279 2 cf3 HH C-SOMe Ph 69-71 1-280 2 cf3 HH C-SOMe 2-Cl-Ph 1-281 2 cf3 HH C-SOMe 3-Cl-Ph 1-282 2 cf3 HH C-SOMe 4-Cl-Ph 149-150 1-283 2 cf3 HH C-SOMe 2,6-Cl7-Ph 1-284 2 cf3 HH C-SOMe 2,6-Me? -Ph 1-285 2 cf3 HH C-S02Mc Ph 70-72 1-286 2 cf3 HH C-S02Me 2-Cl-Ph 154-156 1-287 2 cf3 HH C-S02Me 3-Cl-Ph 1-288 2 cf3 HH C-SO? Me 4-Cl-Ph 141-143 1-289 2 CF3 HH C-SO? Me 2,6-Cl? -Ph 1-290 2 cf3 HH C-S02Me 2,6-Me, -Ph 1-291 2 cf3 HH C-Ph Et 142-144 1-292 2 cf3 HH C-Ph Ph 159-160 1-293 2 cf3 HH C-Ph 2,6-Cl, -Ph 1-294 2 cf3 HH C-Ph 256-Me2 -Ph 1-295 3 cf3 HH CH Me 1-296 3 cf3 HH CH t-Bu 1-297 3 cf3 HH CH -CH? -Ph 1-298 3 cf3 HH CH -CMe2-Ph 1-299 3 cf3 HH CH Ph 1-300 3 cf3 HH CH 2-Cl-Ph 1-301 3 cf3 HH CH 3-Cl-Ph 1-302 3 cf3 HH CH 4-Cl-Ph 1-303 3 cf3 HH CH 2-Me-Ph 1 -304 3 cf3 HH CH 2-CF3-Ph 1-305 3 cf3 HH CH 2,6-ClrPh 1-306 3 cf3 HH CH 2,6-MerPh 1-307 3 cf3 HH CH 2-Cl-6-F- Ph 1-308 3 cf3 HH CH 2-Cl-6-Me-Ph 1-309 4 c f3 HH CH Me 1-310 4 cf3 HH CH t-Bu 1-311 4 cf3 HH CH -CH7-Ph 1-312 4 cf3 HH CH -CMe, -Ph 1-313 4 cf3 HH CH Ph 1-314 4 cf3 HH CH 2-Cl-Ph 1-315 4 cf3 HH CH 3-Cl-Ph 1-316 4 cf3 HH CH 4-Cl-Ph 200404764 Table 1 (continued)

No. Rl r2 x位置 J5 R9 物性〔融點（°C)、折射率〕 1-317 1-318 1-319 1-320 1-321 1-322 1-323 1-324 1-325 1-326 1-327 1-328 444444222222 3333333333 3 1» ffffffffffffcccccccccccc Η Η CH 2-Me-Ph Η Η CH 2-CF3-Ph Η Η CH 2,6-Cl7-Ph Η Η CH 2,6-Me7-Ph Η Η CH 2-Cl-6-F-Ph Η Η· CH 2-Cl-6-Me-Ph Η Η CH 4-(4-CF3-Ph)-Ph 136-138 Η Η CH 2-Me-4-(4-CF3-Ph)-Ph 65-67 Η 4-C1 CH 2-Pyn 46-48 Η Η C-Br 2,3-ClrPh 143-145 Η Η CH 2-(l-Me-n-C5Hn)-Ph 1.5226(28〇C) Η Η CH c-Hex 114-116 通式（I一 4)No. Rl r2 x position J5 R9 Physical properties [melting point (° C), refractive index] 1-317 1-318 1-319 1-320 1-321 1-322 1-323 1-324 1-325 1-326 1-327 1-328 444444222222 3333333333 3 1 »ffffffffffffcccccccccccc Η Η CH 2-Me-Ph Η Η CH 2-CF3-Ph Η Η CH 2,6-Cl7-Ph Η Η CH 2,6-Me7-Ph Η Η CH 2-Cl-6-F-Ph Η CHCH 2-Cl-6-Me-Ph Η Η CH 4- (4-CF3-Ph) -Ph 136-138 Η CH 2-Me-4- ( 4-CF3-Ph) -Ph 65-67 Η 4-C1 CH 2-Pyn 46-48 Η Η C-Br 2,3-ClrPh 143-145 Η Η CH 2- (l-Me-n-C5Hn)- Ph 1.5226 (28〇C) Η Η CH c-Hex 114-116 General formula (I-4)

(1-4) -39- 200404764 第2表（m=〇、A=- CH2 ^G^O、J5二N) No. 取代 位置 R1 R2 X J4 R9 物性 〔融點（°C)〕 2-1 2 cf3 H H CH Me 2-2 2 cf3 H H CH Et 2-3 2 cf3 H H CH n-Pr 2-4 2 cf3 H H CH i-Pr 2-5 2 cf3 H H CH c-Pr 2-6 2 cf3 H H CH n-Bu 2-7 2 cf3 H H CH t-Bu 2-8 2 cf3 H H CH -CH，-Ph 104.2 2-9 2 cf3 H H CH -CH7-(2-Cl-Ph) 49.8 2-10 2 cf3 H H CH -CH2-(3-Cl-Ph) 2-11 2 cf3 H H CH -CH，-(4-Cl-Ph) 2-12 2 CF3 H H CH -CHr(2,6-CVPh) 136.6-138.1 2-13 2 cf3 H H CH -CHMe-Ph 2-14 2 cf3 H H CH -CHMe-(2-Cl-Ph) 2-15 2 cf3 H H CH -CHMe-(3-Cl-Ph) 2-16 2 cf3 H H CH -CHMe-(4-Cl-Ph) 2-17 2 cf3 H H CH -CHMe-(2,6-Cl2-Ph) 2-18 2 cf3 H H CH -CMe，-Ph 2-19 2 cf3 H H CH -CMe?-(2-Cl-Ph) 2-20 2 cf3 H H CH -CMe,-(3-Cl-Ph) 2-21 2 cf3 H H CH -CMe2-(4-Cl-Ph) 2-22 2 cf3 H H CH -CMe,-(2,6-Cl?-Ph) 2-23 2 cf3 H H CH Ph ~ 94.2 2-24 2 cf3 H H CH 2-F-Ph 161.3 2-25 2 cf3 H H CH 3-F-Ph 2-26 2 cf3 H H CH 4-F-Ph 2-27 2 cf3 H H CH 2-Cl-Ph 187.9 2-28 2 cf3 H H CH 3-Cl-Ph 113.2-120.8 2-29 2 cf3 H H CH 4-Cl-Ph 175,6 2-30 2 cf3 H H CH 2-Br-Ph 118.3 2-31 2 cf3 H H CH 3-Br-Ph 2-32 2 cf3 H H CH 4-Br-Ph 2-33 2 cf3 H H CH 2-I-Ph 2-34 2 cf3 H H CH 3-I-Ph 2-35 2 cf3 H H CH 4-I-Ph 2-36 2 cf3 H H CH 2-Me-Ph 186.7 2-37 2 cf3 H H CH 3-Me-Ph 123.0-131.7 2-38 2 cf3 H H CH 4-Me-Ph 136.5-142.9 2-39 2 cf3 H H CH 2-Et-Ph 2-40 2 cf3 H H CH 2-i-Pr-Ph 2-41 2 cf3 H H CH 2-OMe-Ph 170 2-42 2 CF, H H CH 3-OMe-Ph 200404764 第2表（續)(1-4) -39- 200404764 Table 2 (m = 〇, A =-CH2 ^ G ^ O, J5 two N) No. Substitution position R1 R2 X J4 R9 Physical properties [melting point (° C)] 2- 1 2 cf3 HH CH Me 2-2 2 cf3 HH CH Et 2-3 2 cf3 HH CH n-Pr 2-4 2 cf3 HH CH i-Pr 2-5 2 cf3 HH CH c-Pr 2-6 2 cf3 HH CH n-Bu 2-7 2 cf3 HH CH t-Bu 2-8 2 cf3 HH CH -CH, -Ph 104.2 2-9 2 cf3 HH CH -CH7- (2-Cl-Ph) 49.8 2-10 2 cf3 HH CH -CH2- (3-Cl-Ph) 2-11 2 cf3 HH CH -CH,-(4-Cl-Ph) 2-12 2 CF3 HH CH -CHr (2,6-CVPh) 136.6-138.1 2 -13 2 cf3 HH CH -CHMe-Ph 2-14 2 cf3 HH CH -CHMe- (2-Cl-Ph) 2-15 2 cf3 HH CH -CHMe- (3-Cl-Ph) 2-16 2 cf3 HH CH -CHMe- (4-Cl-Ph) 2-17 2 cf3 HH CH -CHMe- (2,6-Cl2-Ph) 2-18 2 cf3 HH CH -CMe, -Ph 2-19 2 cf3 HH CH- CMe?-(2-Cl-Ph) 2-20 2 cf3 HH CH -CMe,-(3-Cl-Ph) 2-21 2 cf3 HH CH -CMe2- (4-Cl-Ph) 2-22 2 cf3 HH CH -CMe,-(2,6-Cl? -Ph) 2-23 2 cf3 HH CH Ph ~ 94.2 2-24 2 cf3 HH CH 2-F-Ph 161.3 2-25 2 cf3 HH CH 3-F- Ph 2-26 2 cf3 HH CH 4-F-Ph 2-27 2 cf3 HH CH 2-Cl-Ph 187.9 2-28 2 cf3 HH CH 3- Cl-Ph 113.2-120.8 2-29 2 cf3 HH CH 4-Cl-Ph 175,6 2-30 2 cf3 HH CH 2-Br-Ph 118.3 2-31 2 cf3 HH CH 3-Br-Ph 2-32 2 cf3 HH CH 4-Br-Ph 2-33 2 cf3 HH CH 2-I-Ph 2-34 2 cf3 HH CH 3-I-Ph 2-35 2 cf3 HH CH 4-I-Ph 2-36 2 cf3 HH CH 2-Me-Ph 186.7 2-37 2 cf3 HH CH 3-Me-Ph 123.0-131.7 2-38 2 cf3 HH CH 4-Me-Ph 136.5-142.9 2-39 2 cf3 HH CH 2-Et-Ph 2 -40 2 cf3 HH CH 2-i-Pr-Ph 2-41 2 cf3 HH CH 2-OMe-Ph 170 2-42 2 CF, HH CH 3-OMe-Ph 200404764 Table 2 (continued)

No. 取代 位置 R1 R2 X J4 R9 物性 〔融點（°C)〕 2-43 2 cf3 H H CH 4-OMe-Ph 145.9 2-44 2 cf3 H H CH 2-SMe-Ph 2-45 2 cf3 H H CH 2-SOMe-Ph 2-46 2 CF3 H H CH 2-SO，Me-Ph 2-47 2 cf3 H H CH 2-CN-Ph 2-48 2 cf3 H H CH 4-CN-Ph 2-49 2 cf3 H H CH 2-N02-Ph 2-50 2 cf3 H H CH 4-NCVPh 2-51 2 cf3 H H CH 2-CF3-Ph 179.3 2-52 2 cf3 H H CH 3-CF3-Ph 2-53 2 cf3 H H CH 4-CF3-Ph 2-54 2 cf3 H H CH 2-OCF3-Ph 2-55 2 cf3 H H CH 3-OCF3-Ph 2-56 2 cf3 H H CH 4-OCF3-Ph 2-57 2 cf3 H H CH 2-SCF3-Ph 2-58 2 cf3 H H CH 2-SOCF3-Ph 2-59 2 cf3 H H CH 2-SO,CF3-Ph 2-60 2 cf3 H H CH 2-CO,H-Ph 252.9-259.5 2-61 2 cf3 H H CH 2-COjMe-Ph 158.4-159.2 2-62 2 cf3 H H CH 2-Ph-Ph 2-63 2 cf3 H H CH 2,5-F?-Ph 161.6-162.1 2-64 2 cf3 H H CH 2,6-F;-Ph 169.1-169.6 2-65 2 cf3 H H CH 2,3-Cl?-Ph 206.6 2-66 2 cf3 H H CH 2,4-Cl,-Ph 177.5 2-67 2 cf3 H H CH 2,5-Cl，-Ph 126.8-129.2 2-68 2 cf3 H H CH 2,6-ClrPh 174.5-177.1 2-69 2 cf3 H H CH 3,4-Cl?-Ph 132.8-137.6 2-70 2 cf3 H H CH 2,4-F，-Ph 175.9 2-71 2 cf3 H H CH 2,6-Br7-Ph 204.0-205.6 2-72 2 cf3 H H CH 3-Cl-4-Me-Ph 146 2-73 2 cf3 H H CH 2,3-Me2-Ph 212.0-216.4 2-74 2 cf3 H H CH 2,4-MerPh 2-75 2 cf3 H H CH 3-Cl-4-Me-Ph 146.0 2-76 2 cf3 H H CH 2,6-Me，-Ph 163.7-165.3 2-77 2 cf3 H H CH 2,6-Et2-Ph 2-78 2 cf3 H H CH 2,6-(OMe)2-Ph 2-79 2 cf3 H H CH 2-Me-4-i-C3F7-Ph 91.1-120.6 2-80 2 cf3 H H CH 2,6-(CF3)9-Ph 2-81 2 cf3 H H CH 2-Cl-6-Me-Ph 158.3-163.1 2-82 2 cf3 H H CH 2,3,5,6-F4-Ph 157.2-160.2 2-83 2 CF, H H CH 2,3,4,5,6-F,-Ph 180.9-181.2No. Substitution position R1 R2 X J4 R9 Physical properties [melting point (° C)] 2-43 2 cf3 HH CH 4-OMe-Ph 145.9 2-44 2 cf3 HH CH 2-SMe-Ph 2-45 2 cf3 HH CH 2-SOMe-Ph 2-46 2 CF3 HH CH 2-SO, Me-Ph 2-47 2 cf3 HH CH 2-CN-Ph 2-48 2 cf3 HH CH 4-CN-Ph 2-49 2 cf3 HH CH 2-N02-Ph 2-50 2 cf3 HH CH 4-NCVPh 2-51 2 cf3 HH CH 2-CF3-Ph 179.3 2-52 2 cf3 HH CH 3-CF3-Ph 2-53 2 cf3 HH CH 4-CF3 -Ph 2-54 2 cf3 HH CH 2-OCF3-Ph 2-55 2 cf3 HH CH 3-OCF3-Ph 2-56 2 cf3 HH CH 4-OCF3-Ph 2-57 2 cf3 HH CH 2-SCF3-Ph 2-58 2 cf3 HH CH 2-SOCF3-Ph 2-59 2 cf3 HH CH 2-SO, CF3-Ph 2-60 2 cf3 HH CH 2-CO, H-Ph 252.9-259.5 2-61 2 cf3 HH CH 2-COjMe-Ph 158.4-159.2 2-62 2 cf3 HH CH 2-Ph-Ph 2-63 2 cf3 HH CH 2,5-F? -Ph 161.6-162.1 2-64 2 cf3 HH CH 2,6-F ; -Ph 169.1-169.6 2-65 2 cf3 HH CH 2,3-Cl? -Ph 206.6 2-66 2 cf3 HH CH 2,4-Cl, -Ph 177.5 2-67 2 cf3 HH CH 2,5-Cl , -Ph 126.8-129.2 2-68 2 cf3 HH CH 2,6-ClrPh 174.5-177.1 2-69 2 cf3 HH CH 3,4-Cl? -Ph 132.8-137.6 2-70 2 cf3 HH CH 2,4- F, -Ph 175. 9 2-71 2 cf3 HH CH 2,6-Br7-Ph 204.0-205.6 2-72 2 cf3 HH CH 3-Cl-4-Me-Ph 146 2-73 2 cf3 HH CH 2,3-Me2-Ph 212.0 -216.4 2-74 2 cf3 HH CH 2,4-MerPh 2-75 2 cf3 HH CH 3-Cl-4-Me-Ph 146.0 2-76 2 cf3 HH CH 2,6-Me, -Ph 163.7-165.3 2 -77 2 cf3 HH CH 2,6-Et2-Ph 2-78 2 cf3 HH CH 2,6- (OMe) 2-Ph 2-79 2 cf3 HH CH 2-Me-4-i-C3F7-Ph 91.1- 120.6 2-80 2 cf3 HH CH 2,6- (CF3) 9-Ph 2-81 2 cf3 HH CH 2-Cl-6-Me-Ph 158.3-163.1 2-82 2 cf3 HH CH 2,3,5, 6-F4-Ph 157.2-160.2 2-83 2 CF, HH CH 2,3,4,5,6-F, -Ph 180.9-181.2

-4 1- 200404764 第2表（續) No. 取代 位置 R1 R2 X J4 R9 物性 〔融點（°C)〕 2-84 2 cf3 H H CH 2,3,4-Cl3-Ph 2-85 2 cf3 H H CH 2,4,6-Cl3-Ph 171.1-171.2 2-86 2 cf3 H H CH 2,6-Cl?-4-CFrPh 124.2 2-87 2 cf3 H H CH 2,6-Cl7-4-OCF3-Ph 108.1 2-88 2 cf3 H H CH 2,6-Br;-4-F-Ph 170.5-173.2 2-89 2 cf3 H H CH 2-Pyn 2-90 2 cf3 H H CH 3-Pyn 2-91 2 cf3 H H CH 4-Pyn 2-92 2 cf3 H H CH 6-Cl-2-Pyn 64.9-68.6 2-93 2 cf3 H H CH 3,5-Cl2-2-Pyn 157.9-158.5 2-94 2 cf3 H H CH 6-Cl-4-CF3-2-Pyn 52.1-63.0 2-95 2 cf3 H H CH 2-Pym 2-96 2 cf3 H H CH 4-Pym 2-97 2 cf3 H H CH 4,6-Me2-2-Pym 2-98 2 cf3 H H CH 4,6-(OMe)2-2-Pym 226.3-226.6 2-99 2 cf3 H H CH 3-Pyd 2-100 2 cf3 H H CH 6-Cl-3-Pyd 2-101 2 cf3 H H CH -CO-NHMe 2-102 2 cf3 H H CH -CO-NHPh 2-103 2 cf3 H H CH -CO-NMePh 2-104 2 cf3 H H CH -CO-NEt(c-Hex) 2-105 2 cf3 H H CH -CO-N(i-Pr)2 2-106 2 cf3 Me H CH Ph 2-107 2 cf3 Me H CH 2-Cl-Ph 2-108 2 cf3 Me H CH 2,6-Cl2-Ph 2-109 2 cf3 Me H CH 2,6-Me?-Ph 2-110 2 cf3 Me H CH -CH2-Ph 2-111 2 cf3 Me H CH -CMe,-Ph 2-112 2 cf3 COMe H CH Ph 2-113 2 cf3 COMe H CH 2-Cl-Ph 2-114 2 cf3 COMe H CH 2,6-Cl2-Ph 2-115 2 cf3 COMe H CH 2,6-Me2-Ph 2-116 2 cf3 COMe H CH -CH7-Ph 2-117 2 cf3 COMe H CH -CMe9-Ph 2-118 2 cf3 C02Me H CH Ph 2-119 2 cf3 C02Me H CH 2-Cl-Ph 2-120 2 cf3 CO?Me H CH 2,6-Cl,-Ph 2-121 2 cf3 C02Me H CH 2,6-Me，-Ph 2-122 2 cf3 C02Me H CH -CH2-Ph 2-123 2 cf3 CO，Me H CH -CMe2-Ph 2-124 2 CF? SO^CF, H CH Ph 200404764 第2表（續) No. 取代 位置 R1 R2 X J4 R9 物性 〔融點（°C)〕 2-125 2 cf3 so?cf3 H CH 2-Cl-Ph 2-126 2 cf3 so2cf3 H CH 2,6-CU-Ph 2-127 2 cf3 so2cf3 H CH 2,6-Me7-Ph 2-128 2 cf3 so7cf3 H CH -CH,-Ph 2-129 2 cf3 so2cf3 H CH -CMe,-Ph 2-130 2 cf3 H 5-Me CH Ph 91.7-106.2 2-131 2 cf3 H 4-C1 CH Ph 2-132 2 cf3 H 4-C1 CH 2-Cl-Ph 2-133 2 CF3 H 4-C1 CH 2,6-Cl 厂 Ph 2-134 2 cf3 H 4-C1 CH 2-Cl-6-F-Ph 2-135 2 cf3 H 4-C1 CH 2,6-Me7-Ph 2-136 2 cf3 H 4-C1 CH 2-Cl-6-Me-Ph 2-137 2 cf3 H 4-C1 CH -CH，-Ph 2-138 2 cf3 H 4-C1 CH -CMe2-Ph 2-139 2 cf3 H 5-C1 CH Ph 2-140 2 cf3 H 5-C1 CH 2-Cl-Ph 2-141 2 cf3 H 5-C1 CH 2,6-Cl?-Ph 2-142 2 cf3 H 5-C1 CH 2-Cl-6-F-Ph 2-143 2 cf3 H 5-C1 CH 2,6-Me2-Ph 2-144 2 cf3 H 5-C1 CH 2-Cl-6-Me-Ph 2-145 2 cf3 H 5-C1 CH -CH?-Ph 2-146 2 cf3 H 5-C1 CH -CMe，-Ph 2-147 3 cf3 H H CH Me 2-148 3 cf3 H H CH -CH2-Ph 2-149 3 cf3 H H CH -CMe7-Ph 2-150 3 cf3 H H CH Ph 2-151 3 cf3 H H CH 2-Cl-Ph 2-152 3 cf3 H H CH 2-CF3-Ph 2-153 3 cf3 H H CH 2,6-Cl?-Ph 2-154 3 cf3 H H CH 256-Me7-Ph 2-155 4 cf3 H H CH Me 2-156 4 cf3 H H CH -CH2-Ph 2-157 4 cf3 H H CH -CMe2-Ph 2-158 4 cf3 H H CH Ph 2-159 4 cf3 H H CH 2-Cl-Ph 2-160 4 cf3 H H CH 2-CF3-Ph 2-161 4 cf3 H H CH 2,6-Cl2-Ph 2-162 4 cf3 H H CH 2,6-Me2-Ph 2-163 2 chf7 H H CH t-Bu 2-164 2 CHF, H H CH -CH,-Ph 200404764 第2表（續) No. 取代 位置 R1 R2 X J4 物性 〔融點（°C)、折射率〕 2-165 2 chf2 H H CH -CMe7-Ph 2-166 2 chf9 H H CH Ph 2-167 2 chf7 H H CH 2-Cl-Ph 188.1 2-168 2 chf9 H H CH 2-OMe-Ph 2-169 2 CHF, H H CH 2-CF3-Ph 176.7-182.1 2-170 2 chf2 H H CH 2-OCF3-Ph 2-171 2 CHF, H H CH 2,6-Cl2-Ph 2-172 2 CHF， H H CH 2,6-Me2-Ph 2-173 2 cf3 H H C-Me t-Bu 2-174 2 cf3 H H C-Me -CH,-Ph 2-175 2 cf3 H H C-Me -CMe2-Ph 2-176 2 cf3 H H C-Me Ph 180.6 2-177 2 cf3 H H C-Me 2-Cl-Ph L5532(24〇C) 2-178 2 cf3 H H C-Me 3-Cl-Ph 2-179 2 cf3 H H C-Me 4-Cl-Ph 2-180 2 cf3 H H C-Me 2-Me-Ph 2-181 2 cf3 H H C-Me 2-OMe-Ph 2-182 2 cf3 H H C-Me 2-CF3-Ph 2-183 2 cf3 H H C-Me 2-OCF3-Ph 2-184 2 cf3 H H C-Me 2,6-ClrPh 223.5 2-185 2 CF3 H H C-Me 2,4,6-Cl3-Ph 175.7 2-186 2 cf3 H H C-Me 2,6-Me，-Ph 161.5 2-187 2 cf3 H H C-Me 2-Cl-6-Me-Ph 2-188 2 cf3 H H C-Me 2-Pyn 2-189 2 cf3 H H C-Me 3-Pyn 2-190 2 cf3 H H C-Me 4-Pyn 2-191 2 cf3 H H C-Me 6-Cl2-Pyn 2-192 2 cf3 H H C-Me 6-CF3-2-Pyn 2-193 2 cf3 H H C-Me 6-Cl-4-CF3-2-Pyn 2-194 2 cf3 H H C-Me 2-Pym 2-195 2 cf3 H H C-Me 4-Pym 2-196 2 cf3 H H C-Me 4,6-Me2-2-Pym 2-197 2 cf3 H H C-Me 4,6-(OMe)?-2-Pym 2-198 2 cf3 H H C-Me 3-Pyd - 2-199 2 cf3 H H C-Me 6-Cl-3-Pyd 2-200 2 cf3 H H C-Me -CO-NHMe 2-201 2 cf3 H H C-Me -CO-NHPh 2-202 2 cf3 H H C-Me -CO-NMePh 2-203 2 cf3 H H C-Me -CO-NEt(c-Hex) 2-204 2 cf3 H H C-Me -CO-N(i-Pr), 2-205 2 CF? Et H C-Me Ph 124.3 200404764 第2表（續) No. 取代 位置 R1 R2 X J4 R9 物性 〔融點（°C)〕 2-206 2 cf3 H H c-cf3 t-Bu 2-207 2 cf3 H H c-cf3 -CH2-Ph 2-208 2 cf3 H H c-cf3 -CMe2-Ph 2-209 2 cf3 H H c-cf3 Ph 120.3 2-210 2 cf3 H H c-cf3 2-Cl-Ph 2-211 2 cf3 H H c-cf3 2-CF3-Ph 2-212 2 cf3 H H c-cf3 2-OCF3-Ph 2-213 2 cf3 H H c-cf3 256-Cl,-Ph 2-214 2 cf3 H H c-cf3 2-Cl-6-F-Ph 2-215 2 cf3 H H c-cf3 2,6-Me2-Ph 2-216 2 cf3 H H c-cf3 2-Cl-6-Me-Ph 2-217 2 CF3 H H C-OMe Me 2-218 2 cf3 H H C-OMe t-Bu 2-219 2 cf3 H H C-OMe -CH2-Ph 2-220 2 cf3 H H C-OMe -CMe2-Ph 2-221 2 cf3 H H C-OMe Ph 171.1 2-222 2 cf3 H H C-OMe 2-Cl-Ph 2-223 2 cf3 H H C-OMe 2-CF3-Ph 2-224 2 cf3 H H C-OMe 2-OCF3-Ph 2-225 2 cf3 H H C-OMe 2,6-ClrPh 2-226 2 cf3 H H C-OMe 2,6-Me9-Ph 2-227 2 cf3 H 5-Me C-OMe Ph 176.9-178.3 2-228 2 cf3 H H C-SMe Me 2-229 2 cf3 H H C-SMe t-Bu 2-230 2 cf3 H H C-SMe -CH2-Ph 2-231 2 cf3 H H C-SMe -CMe,-Ph 2-232 2 cf3 H H C-SMe Ph 2-233 2 CF3 H H C-SMe 2-Cl-Ph 2-234 2 cf3 H H C-SMe 2,6-Cl7-Ph 2-235 2 cf3 H H C-SMe 2,6-Me?-Ph 2-236 2 cf3 H H C-Cl -CH,-Ph 2-237 2 cf3 H H C-Cl -CMe?-Ph 2-238 2 cf3 H H C-Cl Ph 2-239 2 cf3 H H C-Cl 2-Cl-Ph 2-240 2 cf3 H H C-Cl 2,6-Cl2-Ph 2-241 2 cf3 H H C-Cl 2-Cl-6-F-Ph 2-242 2 cf3 H H C-Cl 2,6-Me,-Ph 2-243 2 cf3 H H C-Cl 2-Cl-6-Me-Ph 2-244 2 cf3 H H C-Me 4-Cl-2-F-5-i-Pr-Ph 59-61 2-245 2 cf3 H 3-C1 CH 2,4,6-Cl3-Ph 129.3-133.1 2-246 2 cf3 H 3,5-Cl， CH 2,4,6-ClrPh 106.4-124.2 2-247 2 cf3 CO-i-Pr H CH 2,6-Cl， 55.6-61.9 200404764 通式（I — 4 )-4 1- 200404764 Table 2 (continued) No. Replacement position R1 R2 X J4 R9 Physical properties [melting point (° C)] 2-84 2 cf3 HH CH 2,3,4-Cl3-Ph 2-85 2 cf3 HH CH 2,4,6-Cl3-Ph 171.1-171.2 2-86 2 cf3 HH CH 2,6-Cl? -4-CFrPh 124.2 2-87 2 cf3 HH CH 2,6-Cl7-4-OCF3-Ph 108.1 2-88 2 cf3 HH CH 2,6-Br; -4-F-Ph 170.5-173.2 2-89 2 cf3 HH CH 2-Pyn 2-90 2 cf3 HH CH 3-Pyn 2-91 2 cf3 HH CH 4-Pyn 2-92 2 cf3 HH CH 6-Cl-2-Pyn 64.9-68.6 2-93 2 cf3 HH CH 3,5-Cl2-2-Pyn 157.9-158.5 2-94 2 cf3 HH CH 6-Cl- 4-CF3-2-Pyn 52.1-63.0 2-95 2 cf3 HH CH 2-Pym 2-96 2 cf3 HH CH 4-Pym 2-97 2 cf3 HH CH 4,6-Me2-2-Pym 2-98 2 cf3 HH CH 4,6- (OMe) 2-2-Pym 226.3-226.6 2-99 2 cf3 HH CH 3-Pyd 2-100 2 cf3 HH CH 6-Cl-3-Pyd 2-101 2 cf3 HH CH- CO-NHMe 2-102 2 cf3 HH CH -CO-NHPh 2-103 2 cf3 HH CH -CO-NMePh 2-104 2 cf3 HH CH -CO-NEt (c-Hex) 2-105 2 cf3 HH CH -CO -N (i-Pr) 2 2-106 2 cf3 Me H CH Ph 2-107 2 cf3 Me H CH 2-Cl-Ph 2-108 2 cf3 Me H CH 2,6-Cl2-Ph 2-109 2 cf3 Me H CH 2,6-Me? -Ph 2-110 2 cf3 Me H CH -CH2-Ph 2-111 2 cf3 Me H CH -CMe, -Ph 2-112 2 cf3 COMe H CH Ph 2-113 2 cf3 COMe H CH 2-Cl-Ph 2-114 2 cf3 COMe H CH 2, 6-Cl2-Ph 2-115 2 cf3 COMe H CH 2,6-Me2-Ph 2-116 2 cf3 COMe H CH -CH7-Ph 2-117 2 cf3 COMe H CH -CMe9-Ph 2-118 2 cf3 C02Me H CH Ph 2-119 2 cf3 C02Me H CH 2-Cl-Ph 2-120 2 cf3 CO? Me H CH 2,6-Cl, -Ph 2-121 2 cf3 C02Me H CH 2,6-Me, -Ph 2-122 2 cf3 C02Me H CH -CH2-Ph 2-123 2 cf3 CO, Me H CH -CMe2-Ph 2-124 2 CF? SO ^ CF, H CH Ph 200404764 Table 2 (continued) No. Substitution position R1 R2 X J4 R9 Physical properties [melting point (° C)] 2-125 2 cf3 so? Cf3 H CH 2-Cl-Ph 2-126 2 cf3 so2cf3 H CH 2,6-CU-Ph 2-127 2 cf3 so2cf3 H CH 2,6-Me7-Ph 2-128 2 cf3 so7cf3 H CH -CH, -Ph 2-129 2 cf3 so2cf3 H CH -CMe, -Ph 2-130 2 cf3 H 5-Me CH Ph 91.7-106.2 2 -131 2 cf3 H 4-C1 CH Ph 2-132 2 cf3 H 4-C1 CH 2-Cl-Ph 2-133 2 CF3 H 4-C1 CH 2,6-Cl Factory Ph 2-134 2 cf3 H 4- C1 CH 2-Cl-6-F-Ph 2-135 2 cf3 H 4-C1 CH 2,6-Me7-Ph 2-136 2 cf3 H 4-C1 CH 2-Cl-6-Me-Ph 2-137 2 cf3 H 4-C1 CH -CH -Ph 2-138 2 cf3 H 4-C1 CH -CMe2-Ph 2-139 2 cf3 H 5-C1 CH Ph 2-140 2 cf3 H 5-C1 CH 2-Cl-Ph 2-141 2 cf3 H 5- C1 CH 2,6-Cl? -Ph 2-142 2 cf3 H 5-C1 CH 2-Cl-6-F-Ph 2-143 2 cf3 H 5-C1 CH 2,6-Me2-Ph 2-144 2 cf3 H 5-C1 CH 2-Cl-6-Me-Ph 2-145 2 cf3 H 5-C1 CH -CH? -Ph 2-146 2 cf3 H 5-C1 CH -CMe, -Ph 2-147 3 cf3 HH CH Me 2-148 3 cf3 HH CH -CH2-Ph 2-149 3 cf3 HH CH -CMe7-Ph 2-150 3 cf3 HH CH Ph 2-151 3 cf3 HH CH 2-Cl-Ph 2-152 3 cf3 HH CH 2-CF3-Ph 2-153 3 cf3 HH CH 2,6-Cl? -Ph 2-154 3 cf3 HH CH 256-Me7-Ph 2-155 4 cf3 HH CH Me 2-156 4 cf3 HH CH- CH2-Ph 2-157 4 cf3 HH CH -CMe2-Ph 2-158 4 cf3 HH CH Ph 2-159 4 cf3 HH CH 2-Cl-Ph 2-160 4 cf3 HH CH 2-CF3-Ph 2-161 4 cf3 HH CH 2,6-Cl2-Ph 2-162 4 cf3 HH CH 2,6-Me2-Ph 2-163 2 chf7 HH CH t-Bu 2-164 2 CHF, HH CH -CH, -Ph 200404764 2 Table (continued) No. Substitution position R1 R2 X J4 Physical properties [melting point (° C), refractive index] 2-165 2 chf2 HH CH -CMe7-Ph 2-166 2 chf9 HH CH Ph 2-167 2 chf7 HH CH 2-C l-Ph 188.1 2-168 2 chf9 HH CH 2-OMe-Ph 2-169 2 CHF, HH CH 2-CF3-Ph 176.7-182.1 2-170 2 chf2 HH CH 2-OCF3-Ph 2-171 2 CHF, HH CH 2,6-Cl2-Ph 2-172 2 CHF, HH CH 2,6-Me2-Ph 2-173 2 cf3 HH C-Me t-Bu 2-174 2 cf3 HH C-Me -CH, -Ph 2-175 2 cf3 HH C-Me -CMe2-Ph 2-176 2 cf3 HH C-Me Ph 180.6 2-177 2 cf3 HH C-Me 2-Cl-Ph L5532 (24〇C) 2-178 2 cf3 HH C-Me 3-Cl-Ph 2-179 2 cf3 HH C-Me 4-Cl-Ph 2-180 2 cf3 HH C-Me 2-Me-Ph 2-181 2 cf3 HH C-Me 2-OMe-Ph 2-182 2 cf3 HH C-Me 2-CF3-Ph 2-183 2 cf3 HH C-Me 2-OCF3-Ph 2-184 2 cf3 HH C-Me 2,6-ClrPh 223.5 2-185 2 CF3 HH C -Me 2,4,6-Cl3-Ph 175.7 2-186 2 cf3 HH C-Me 2,6-Me, -Ph 161.5 2-187 2 cf3 HH C-Me 2-Cl-6-Me-Ph 2- 188 2 cf3 HH C-Me 2-Pyn 2-189 2 cf3 HH C-Me 3-Pyn 2-190 2 cf3 HH C-Me 4-Pyn 2-191 2 cf3 HH C-Me 6-Cl2-Pyn 2- 192 2 cf3 HH C-Me 6-CF3-2-Pyn 2-193 2 cf3 HH C-Me 6-Cl-4-CF3-2-Pyn 2-194 2 cf3 HH C-Me 2-Pym 2-195 2 cf3 HH C-Me 4-Pym 2-196 2 cf3 HH C-Me 4,6-Me2-2-Pym 2-197 2 cf3 H H C-Me 4,6- (OMe)?-2-Pym 2-198 2 cf3 HH C-Me 3-Pyd-2-199 2 cf3 HH C-Me 6-Cl-3-Pyd 2-200 2 cf3 HH C-Me -CO-NHMe 2-201 2 cf3 HH C-Me -CO-NHPh 2-202 2 cf3 HH C-Me -CO-NMePh 2-203 2 cf3 HH C-Me -CO-NEt (c- Hex) 2-204 2 cf3 HH C-Me -CO-N (i-Pr), 2-205 2 CF? Et H C-Me Ph 124.3 200404764 Table 2 (continued) No. Replacement position R1 R2 X J4 R9 Physical Properties [Melting Point (° C)] 2-206 2 cf3 HH c-cf3 t-Bu 2-207 2 cf3 HH c-cf3 -CH2-Ph 2-208 2 cf3 HH c-cf3 -CMe2-Ph 2-209 2 cf3 HH c-cf3 Ph 120.3 2-210 2 cf3 HH c-cf3 2-Cl-Ph 2-211 2 cf3 HH c-cf3 2-CF3-Ph 2-212 2 cf3 HH c-cf3 2-OCF3-Ph 2-213 2 cf3 HH c-cf3 256-Cl, -Ph 2-214 2 cf3 HH c-cf3 2-Cl-6-F-Ph 2-215 2 cf3 HH c-cf3 2,6-Me2-Ph 2 -216 2 cf3 HH c-cf3 2-Cl-6-Me-Ph 2-217 2 CF3 HH C-OMe Me 2-218 2 cf3 HH C-OMe t-Bu 2-219 2 cf3 HH C-OMe -CH2 -Ph 2-220 2 cf3 HH C-OMe -CMe2-Ph 2-221 2 cf3 HH C-OMe Ph 171.1 2-222 2 cf3 HH C-OMe 2-Cl-Ph 2-223 2 cf3 HH C-OMe 2 -CF3-Ph 2-224 2 cf3 HH C-OMe 2-OCF3-Ph 2-225 2 cf3 HH C-OMe 2,6-ClrPh 2-226 2 cf3 HH C-OMe 2,6-Me9-Ph 2-227 2 cf3 H 5-Me C-OMe Ph 176.9-178.3 2-228 2 cf3 HH C-SMe Me 2-229 2 cf3 HH C-SMe t-Bu 2-230 2 cf3 HH C-SMe -CH2-Ph 2-231 2 cf3 HH C-SMe -CMe, -Ph 2-232 2 cf3 HH C-SMe Ph 2-233 2 CF3 HH C-SMe 2-Cl-Ph 2-234 2 cf3 HH C-SMe 2,6-Cl7-Ph 2-235 2 cf3 HH C-SMe 2,6-Me? -Ph 2-236 2 cf3 HH C-Cl -CH, -Ph 2-237 2 cf3 HH C-Cl -CMe? -Ph 2-238 2 cf3 HH C-Cl Ph 2-239 2 cf3 HH C-Cl 2 -Cl-Ph 2-240 2 cf3 HH C-Cl 2,6-Cl2-Ph 2-241 2 cf3 HH C-Cl 2-Cl-6-F-Ph 2-242 2 cf3 HH C-Cl 2,6 -Me, -Ph 2-243 2 cf3 HH C-Cl 2-Cl-6-Me-Ph 2-244 2 cf3 HH C-Me 4-Cl-2-F-5-i-Pr-Ph 59-61 2-245 2 cf3 H 3-C1 CH 2,4,6-Cl3-Ph 129.3-133.1 2-246 2 cf3 H 3,5-Cl, CH 2,4,6-ClrPh 106.4-124.2 2-247 2 cf3 CO-i-Pr H CH 2,6-Cl, 55.6-61.9 200404764 General formula (I — 4)

R1-S〇2(R2)NR1-S〇2 (R2) N

'H (H) (m=〇 CH2 - ^ G!=0 ' J4=J5=N)'H (H) (m = 〇 CH2-^ G! = 0' J4 = J5 = N)

No. R1 R2No. R1 R2

X R9 物性 〔融點（°C)、折射率〕 012 3456789 012345678901 -* 2 3 4 5 ό 7 οο 9 1 1 Ί_ 1 1 1 1 1_ 1 1 2 2 2 2 2 2 2 2 2 2 3 3 3 3 3 33 33 33333 3333333333333333333 KT2 i TJ T2 rl T2 τι τι τι η τι τι τι τι J1 ί τι- ί ττχ J1 ί Jx J1 ί ί ΤΗΧ J1 ί ττ JX ΤΓ- TL1 ΤΓ- ΤΓ- t t ΤΓ- ρ ΤΗ* -UA tx χκχ ρ ΤΓ- ΤΓ- Tr* ΤΓ- VMM ΤΗΧ ΤΓ- ΤΗΧ τκχ TF TF Trx ΧΗΧ ΤΗΧ ΤΓ* ττχ ΤΓ 3 Γ〇 Γ〇 Γ〇 Γ〇 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 ΊΙ F FF:FF FF FFFFF FFFFFFFFFFFFFFFFFFF CCCICICICCCCCCCCCCCCCCCCCCCCCCCCCC 2 2 2 22 22 22222 2222222222222222222 Η Me Η t-Bu 1.4979(27〇C) Η -CH2-Ph 1.5194(20〇C) Η -CH?-(2-Cl-Ph) 1.5475(22〇C) Η -CH2-(3-Cl-Ph) 97-98 Η -CH2-(4-Cl-Ph) 1.5499(23〇C) Η -CH2-(2,6-Cl2-Ph) Η -CHMe-Ph 1.5287(25〇C) Η -CHMe-(2-Cl-Ph) Η -CHMe-(3-Cl-Ph) Η -CHMe-(4-Cl-Ph) Η -CHMe-(2,6-ClrPh) Η -CMe7-Ph 1.5328(26〇C) Η -CMe,-(2-Cl-Ph) Η -CMe7-(3-Cl-Ph) Η -CMe2-(4-Cl-Ph) Η -CMe2-(256-Cl,-Ph) Η Ph 88-89 Η 2-F-Ph 1.5244(21°C) Η 3-F-Ph Η 4-F-Ph Η 2-Cl-Ph 105-107 Η 3-Cl-Ph 74-75 Η 4-Cl-Ph 127-128 Η 2-Br-Ph 45 Η 3-Br-Ph Η 4-Br-Ph Η 2-I-Ph Η 2-Me-Ph 1.5293(24〇C) Η 2-Et-Ph Η 2-i-Pr-PhX R9 Physical properties (melting point (° C), refractive index) 012 3456789 012345678901-* 2 3 4 5 ό 7 οο 9 1 1 Ί_ 1 1 1 1 1_ 1 1 2 2 2 2 2 2 2 2 2 2 3 3 3 3 3 33 33 33333 3333333333333333333 KT2 i TJ T2 rl T2 τι τι τι η τι τι τι τι J1 ί τι- ί ττχ J1 ί Jx J1 ί ί ΤΗΧ J1 ί ττ JX ΤΓ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Γ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ1 Τ- Τ- Τ- Τ- Τ1 Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ- Τ1 -UA tx χκχ ρ ΤΓ- ΤΓ- Tr * ΤΓ- VMM ΤΗΧ ΤΓ- ΤΗΧ τκχ TF TF Trx χΗΧ ΤΗΧ ΤΓ * ττχ ΤΓ 3 Γ〇Γ〇Γ〇Γ〇3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 ΊΙ F FF: FF FF FFFFF FFFFFFFFFFFFFFFFFFF CCCICICICCCCCCCCCCCCCCCCCCCCCCCCCCCC 2 2 2 22 22 22222 2222222222222222222 Η Me Η t-Bu 1.4979 (27〇C) Η -CH2-Ph 1.5194 (20〇C ) Η -CH?-(2-Cl-Ph) 1.5475 (22〇C) Η -CH2- (3-Cl-Ph) 97-98 Η -CH2- (4-Cl-Ph) 1.5499 (23〇C) Η -CH2- (2,6-Cl2-Ph) Η -CHMe-Ph 1.5287 (25 ° C) Η -CHMe- (2-Cl-Ph) Η -CHMe- (3-Cl-Ph) Η -CHMe- (4-Cl-Ph) Η -CHMe- (2,6-ClrPh) Η -CMe7-Ph 1.5328 (26〇C) Η -CMe,-(2-Cl-Ph) Η -CMe7- (3-Cl- Ph) Η -CMe2- (4-Cl-Ph) Η -CMe2- (256-Cl, -Ph) Η Ph 88-89 Η 2-F-Ph 1.5244 (21 ° C) Η 3-F-Ph Η 4-F- Ph Η 2-Cl-Ph 105-107 Η 3-Cl-Ph 74-75 Η 4-Cl-Ph 127-128 Η 2-Br-Ph 45 Η 3-Br-Ph Η 4-Br-Ph Η 2- I-Ph Η 2-Me-Ph 1.5293 (24〇C) Η 2-Et-Ph Η 2-i-Pr-Ph

-46- 200404764 第3表（續)-46- 200404764 Table 3 (Continued)

No. 取代 位置 R1 R2 X 9 物性 〔融點（°C)、折射率〕 3-32 2 cf3 H H 2-OMe-Ph 90-92 3-33 2 cf3 H H 2-SMe-Ph 3-34 2 cf3 H H 2-SOMe-Ph 3-35 2 cf3 H H 2-SO?Me-Ph 3-36 2 cf3 H H 2-NOrPh 155 3-37 2 cf3 H H 2-CN-Ph 1.5443(26〇C) 3-38 2 cf3 H H 2-CFrPh 95-97 3-39 2 cf3 H H 2-OCF3-Ph 3-40 2 cf3 H H 2-SCF3-Ph 3-41 2 cf3 H H 2-SOCF3-Ph 3-42 2 cf3 H H 2-SO，CF3-Ph 3-43 2 cf3 H H 2-C02Me-Ph 3-44 2 cf3 H H 2-Ph-Ph 3-45 2 cf3 H H 4-PhO-Ph 3-46 2 cf3 H H 2,6-F，-Ph 109-110 3-47 2 cf3 H H 2,4-Cl，-Ph 124 3-48 2 cf3 H H 2,6-Cl，-Ph 139-141 3-49 2 cf3 H H 3,4-Cl,-Ph 88-90 3-50 2 cf3 H H 3,5-Cl2-Ph 3-51 2 cf3 H H 2,6-Br2-Ph 3-52 2 cf3 H H 2,6-I，-Ph 3-53 2 cf3 H H 2,6-Me2-Ph 150-152 3-54 2 cf3 H H 2,6-EVPh 3-55 2 cf3 H H 2,6-(OMe)?-Ph 3-56 2 cf3 H H 2,4-(CF3)2;Ph 3-57 2 cf3 H H 2,6-(CF3)2-Ph 3-58 2 cf3 H H 2,6-(OCF3)，-Ph 3-59 2 cf3 H H 2,4,6-F3-Ph 3-60 2 cf3 H H 2,3,4-Cl3-Ph 3-61 2 cf3 H H 2,4,6-Cl3-Ph 147-149 3-62 2 cf3 H H 2?6-Cl2-4-CF3-Ph 3-63 2 cf3 H H 2,6-Cl7-4-OCF3-Ph 3-64 2 cf3 H H 2,436-Me3-Ph 3-65 2 cf3 H H 2-Pyn 3-66 2 cf3 H H 3-Pyn 3-67 2 cf3 H H 4-Pyn 3-68 2 cf3 H H 6-Cl-2-Pyn 3-69 2 cf3 H H 6-CF3-2-Pyn 3-70 2 cf3 H H 6-Cl-4-CF3-2-Pyn 3-71 2 cf3 H H 2-Pym 3-72 2 cf3 H H 4-Pym 3-73 2 CF, H H 4,6-Me?-2-PymNo. Substitute position R1 R2 X 9 Physical properties [melting point (° C), refractive index] 3-32 2 cf3 HH 2-OMe-Ph 90-92 3-33 2 cf3 HH 2-SMe-Ph 3-34 2 cf3 HH 2-SOMe-Ph 3-35 2 cf3 HH 2-SO? Me-Ph 3-36 2 cf3 HH 2-NOrPh 155 3-37 2 cf3 HH 2-CN-Ph 1.5443 (26〇C) 3-38 2 cf3 HH 2-CFrPh 95-97 3-39 2 cf3 HH 2-OCF3-Ph 3-40 2 cf3 HH 2-SCF3-Ph 3-41 2 cf3 HH 2-SOCF3-Ph 3-42 2 cf3 HH 2-SO , CF3-Ph 3-43 2 cf3 HH 2-C02Me-Ph 3-44 2 cf3 HH 2-Ph-Ph 3-45 2 cf3 HH 4-PhO-Ph 3-46 2 cf3 HH 2,6-F,- Ph 109-110 3-47 2 cf3 HH 2,4-Cl, -Ph 124 3-48 2 cf3 HH 2,6-Cl, -Ph 139-141 3-49 2 cf3 HH 3,4-Cl, -Ph 88-90 3-50 2 cf3 HH 3,5-Cl2-Ph 3-51 2 cf3 HH 2,6-Br2-Ph 3-52 2 cf3 HH 2,6-I, -Ph 3-53 2 cf3 HH 2 , 6-Me2-Ph 150-152 3-54 2 cf3 HH 2,6-EVPh 3-55 2 cf3 HH 2,6- (OMe)?-Ph 3-56 2 cf3 HH 2,4- (CF3) 2 ; Ph 3-57 2 cf3 HH 2,6- (CF3) 2-Ph 3-58 2 cf3 HH 2,6- (OCF3), -Ph 3-59 2 cf3 HH 2,4,6-F3-Ph 3 -60 2 cf3 HH 2,3,4-Cl3-Ph 3-61 2 cf3 HH 2,4,6-Cl3-Ph 147-149 3-62 2 cf3 HH 2? 6-Cl2- 4-CF3-Ph 3-63 2 cf3 HH 2,6-Cl7-4-OCF3-Ph 3-64 2 cf3 HH 2,436-Me3-Ph 3-65 2 cf3 HH 2-Pyn 3-66 2 cf3 HH 3- Pyn 3-67 2 cf3 HH 4-Pyn 3-68 2 cf3 HH 6-Cl-2-Pyn 3-69 2 cf3 HH 6-CF3-2-Pyn 3-70 2 cf3 HH 6-Cl-4-CF3- 2-Pyn 3-71 2 cf3 HH 2-Pym 3-72 2 cf3 HH 4-Pym 3-73 2 CF, HH 4,6-Me? -2-Pym

-4 7- 200404764 第3表（續) No. 取代 位置 R1 R2 X 物性 〔融點（°C)、折射率〕 3-74 2 cf3 H H 4,6-(OMe)2-2-Pym 3-75 2 cf3 H H 3-Pyd 3-76 2 cf3 H H 6-Cl-3-Pyd 3-77 2 cf3 H H -CO-NHMe 3-78 2 cf3 H H -CO-NHPh 3-79 2 cf3 H H -CO-NMePh 1.5302(25〇C) 3-80 2 cf3 H H -CO-NEt(c-Hex) 50 3-81 2 cf3 H H -CO-N(i-Pr)? 3-82 2 cf3 Me H Ph _ 3-83 2 cf3 Me H 2-Cl-Ph NMR-2 3-84 2 cf3 Me H 2-Me-Ph 3-85 2 cf3 Me H 2-CF3-Ph 3-86 2 cf3 Me H 2,6-Cl2-Ph 3-87 2 cf3 Me H 2,6-MerPh 3-88 2 cf3 Me H -CH2-Ph 3-89 2 cf3 Me H -CMe?-Ph 3-90 2 cf3 COMe H Ph 3-91 2 cf3 COMe H 2-Cl-Ph 3-92 2 cf3 COMe H 2,6-ClrPh 3-93 2 cf3 COMe H 2,6-Me2-Ph 3-94 2 cf3 COMe H -CH2-Ph 3-95 2 cf3 COMe H -CMe7-Ph 3-96 2 cf3 C02Me H Ph 3-97 2 cf3 C02Me H 2-Cl-Ph 3-98 2 cf3 C02Me H 2,6-Cl2-Ph 3-99 2 cf3 C02Me H 2,6-Me，-Ph 3-100 2 cf3 C02Me H -CH?-Ph 3-101 2 cf3 C02Me H -CMe2-Ph 3-102 2 cf3 so9cf3 H Ph 3-103 2 cf3 so7cf3 H 2-Cl-Ph 3-104 2 cf3 so2cf3 H 2,6-Cl2-Ph 3-105 2 cf3 so2cf3 H 2,6-Me?-Ph 3-106 2 cf3 so2cf3 H -CH2-Ph 3-107 2 cf3 so2cf3 H -CMe2-Ph 3-108 2 cf3 H 5-Me Ph 3-109 2 cf3 H 5-Me 2-Cl-Ph 3-110 2 cf3 H 5-Me 2,6-Cl,-Ph 3-111 2 cf3 H 5-Me 2,6-Me?-Ph 3-112 2 cf3 H 5-Me -CH,-Ph 3-113 2 cf3 H 5-Me -CMe,-Ph 3-114 2 cf3 H 4-C1 Ph 3-115 2 CF, H 4-C1 2-Cl-Ph-4 7- 200404764 Table 3 (continued) No. Substitution position R1 R2 X Physical properties [melting point (° C), refractive index] 3-74 2 cf3 HH 4,6- (OMe) 2-2-Pym 3- 75 2 cf3 HH 3-Pyd 3-76 2 cf3 HH 6-Cl-3-Pyd 3-77 2 cf3 HH -CO-NHMe 3-78 2 cf3 HH -CO-NHPh 3-79 2 cf3 HH -CO-NMePh 1.5302 (25〇C) 3-80 2 cf3 HH -CO-NEt (c-Hex) 50 3-81 2 cf3 HH -CO-N (i-Pr)? 3-82 2 cf3 Me H Ph _ 3-83 2 cf3 Me H 2-Cl-Ph NMR-2 3-84 2 cf3 Me H 2-Me-Ph 3-85 2 cf3 Me H 2-CF3-Ph 3-86 2 cf3 Me H 2,6-Cl2-Ph 3-87 2 cf3 Me H 2,6-MerPh 3-88 2 cf3 Me H -CH2-Ph 3-89 2 cf3 Me H -CMe? -Ph 3-90 2 cf3 COMe H Ph 3-91 2 cf3 COMe H 2-Cl-Ph 3-92 2 cf3 COMe H 2,6-ClrPh 3-93 2 cf3 COMe H 2,6-Me2-Ph 3-94 2 cf3 COMe H -CH2-Ph 3-95 2 cf3 COMe H- CMe7-Ph 3-96 2 cf3 C02Me H Ph 3-97 2 cf3 C02Me H 2-Cl-Ph 3-98 2 cf3 C02Me H 2,6-Cl2-Ph 3-99 2 cf3 C02Me H 2,6-Me, -Ph 3-100 2 cf3 C02Me H -CH? -Ph 3-101 2 cf3 C02Me H -CMe2-Ph 3-102 2 cf3 so9cf3 H Ph 3-103 2 cf3 so7cf3 H 2-Cl-Ph 3-104 2 cf3 so2cf3 H 2,6-Cl2-Ph 3- 105 2 cf3 so2cf3 H 2,6-Me? -Ph 3-106 2 cf3 so2cf3 H -CH2-Ph 3-107 2 cf3 so2cf3 H -CMe2-Ph 3-108 2 cf3 H 5-Me Ph 3-109 2 cf3 H 5-Me 2-Cl-Ph 3-110 2 cf3 H 5-Me 2,6-Cl, -Ph 3-111 2 cf3 H 5-Me 2,6-Me? -Ph 3-112 2 cf3 H 5 -Me -CH, -Ph 3-113 2 cf3 H 5-Me -CMe, -Ph 3-114 2 cf3 H 4-C1 Ph 3-115 2 CF, H 4-C1 2-Cl-Ph

-48- 200404764 第3表（續) No. 取代 位置 R1 R2 X R9 物性 〔融點（°C)、折射率〕 3-116 2 cf3 H 4-C1 2,6-Cl?-Ph 3-117 2 cf3 H 4-C1 2,6-Me,-Ph 3-118 2 cf3 H 4-C1 -CH7-Ph 3-119 2 cf3 H 4-C1 -CMe?-Ph 3-120 2 cf3 H 5-C1 Ph 3-121 2 cf3 H 5-C1 2-Cl-Ph 3-122 2 cf3 H 5-C1 2,6-Cl2-Ph 3-123 2 cf3 H 5-C1 2,6-Me,-Ph 3-124 2 cf3 H 5-C1 -CH?-Ph 3-125 2 cf3 H 5-C1 -CMe2-Ph 3-126 3 cf3 H H Me 3-127 3 cf3 H H t-Bu 3-128 3 cf3 H H -CH2-Ph 3-129 3 CF3 H H -CMe2-Ph 3-130 3 cf3 H H Ph 3-131 3 cf3 H H 2-Cl-Ph 3-132 3 cf3 H H 2,6-ClrPh 3-133 3 cf3 H H 2-Cl-6-Me-Ph 3-134 3 cf3 H H 256-Me7-Ph 3-135 4 cf3 H H Me 3-136 4 cf3 H H t-Bu 3-137 4 cf3 H H -CH7-Ph 3-138 4 cf3 H H -CMe,-Ph 3-139 4 cf3 H H Ph 3-140 4 cf3 H H 2-Cl-Ph 3-141 4 cf3 H H 2,6-CU-Ph 3-142 4 cf3 H H 2-Cl-6-Me-Ph 3-143 4 cf3 H H 2,6-Me 广 Ph 3-144 2 chf2 H H Me ~ 3-145 2 chf2 H H t-Bu 3-146 2 CHF? H H -CH?-Ph 3-147 2 chf2 H H -CMe2-Ph 3-148 2 CHF? H H Ph 3-149 2 chf2 H H 2-Cl-Ph 3-150 2 chf2 H H 2-CF3-Ph 3-151 2 chf2 H H 2-OCF3 - Ph 3-152 2 CHF, H H 2,6-CU-Ph 3-153 2 CHF, H H 2-Cl-6-F-Ph 3-154 2 CHF, H H 2-Cl-6-Me-Ph 3-155 2 chf2 H H 2,6-MerPh 3-156 2 cf3 H H c-Hex 107 3457 2 cf3 H H 4-SCF3-Ph 1.5214(25°〇 -49- 200404764 第3表（續）-48- 200404764 Table 3 (continued) No. Substitution position R1 R2 X R9 Physical properties [melting point (° C), refractive index] 3-116 2 cf3 H 4-C1 2,6-Cl? -Ph 3-117 2 cf3 H 4-C1 2,6-Me, -Ph 3-118 2 cf3 H 4-C1 -CH7-Ph 3-119 2 cf3 H 4-C1 -CMe? -Ph 3-120 2 cf3 H 5-C1 Ph 3-121 2 cf3 H 5-C1 2-Cl-Ph 3-122 2 cf3 H 5-C1 2,6-Cl2-Ph 3-123 2 cf3 H 5-C1 2,6-Me, -Ph 3- 124 2 cf3 H 5-C1 -CH? -Ph 3-125 2 cf3 H 5-C1 -CMe2-Ph 3-126 3 cf3 HH Me 3-127 3 cf3 HH t-Bu 3-128 3 cf3 HH -CH2- Ph 3-129 3 CF3 HH -CMe2-Ph 3-130 3 cf3 HH Ph 3-131 3 cf3 HH 2-Cl-Ph 3-132 3 cf3 HH 2,6-ClrPh 3-133 3 cf3 HH 2-Cl- 6-Me-Ph 3-134 3 cf3 HH 256-Me7-Ph 3-135 4 cf3 HH Me 3-136 4 cf3 HH t-Bu 3-137 4 cf3 HH -CH7-Ph 3-138 4 cf3 HH -CMe , -Ph 3-139 4 cf3 HH Ph 3-140 4 cf3 HH 2-Cl-Ph 3-141 4 cf3 HH 2,6-CU-Ph 3-142 4 cf3 HH 2-Cl-6-Me-Ph 3 -143 4 cf3 HH 2,6-Me Guang Ph 3-144 2 chf2 HH Me ~ 3-145 2 chf2 HH t-Bu 3-146 2 CHF? HH -CH? -Ph 3-147 2 chf2 HH -CMe2- Ph 3-148 2 CHF? HH Ph 3-149 2 chf2 HH 2-Cl-Ph 3-150 2 chf2 HH 2-CF3-Ph 3-151 2 chf2 HH 2-OCF3-Ph 3-152 2 CHF, HH 2,6-CU-Ph 3-153 2 CHF, HH 2-Cl-6-F-Ph 3-154 2 CHF, HH 2-Cl-6-Me-Ph 3-155 2 chf2 HH 2,6-MerPh 3-156 2 cf3 HH c-Hex 107 3457 2 cf3 HH 4-SCF3-Ph 1.5214 (25 ° 〇-49- 200404764 Table 3 (continued)

No. 取代位置 R1 R2No. Replacement position R1 R2

X R9 物性〔融點ΓΟ、折射率〕 3-158 3-159 3-160 3-161 3-162 3-163 3-164 3-165 3-166 3-167 3-168 3-169 3-170 3-171 3-172 3-173 3-174 3-175 3-176 3-177 3-178 3-179 3-180 3-181 3-182 3-183 3-184 3-185 KTJ1 TT_ ^TT-JX Jijl JITT-TT-Ti- Ti-TUJXJXTT-TT-Ti-Tl T1-TT-TT- thxja tt- jx ίτ^-ΑΤΓΡΤΓΡΤΓ*ΤΓΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΗΧΡΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓΤΓΤΓΤΓ 3 3 3 3 3333333333333333333333 3 i FF F fffffffffffffffffffffffffcccccccccccccccccccccccccccc 22222222222222222222 2 2222222 e T^TUTHAJlJlJXCMTT-TT-JlJliJlJlTlTlTlJlJXTlJiTT-JlJXJXTT-TT- τγτγτγτγτγτγ-^ο^τγττ*τγ-τγ-ρτγ-τγ-τγ-τγ-τηατγ-τγ-ρτ^-τγ-τγ-τγ-τγ-τγ-τγ- 5 4-OMe-Ph 130-131 2-NHrPh 1.5316(24〇C) 2-NHOH-Ph 1.5465(24〇C) 2-NHAc-Ph 1.5241(24〇C) 2,4-F2-Ph 112-113 2-Phthalimidyl-Ph 177-180 2-CF3-Ph 1.4936(28〇C) 2-CFrPh 1.5327(21°C) CH2CO-t-Bu 104-105 CH2COPh 1.5351(23〇C) CH2CO(254-ClrPh) 1.5494(28〇C) CONMe2 1.5099(25〇C) CHMeC02Me 1.4966(27〇C) CHMeCO?H 1.4989(25〇C) CHMeCONH(4-Cl-Ph) 90-95 CMer(3-i-Pr-Ph) 1.5129(28〇C) CH2(2,4-ClrPh) 49 CH2(2-Me-Ph) 106-107 CH2(3-Me-Ph) 1.5275(23〇C) CH?(4-Me-Ph) 1.5431(23〇C) CH2(2,4-Me2-Ph) 30 CH2(4-MeO-Ph) 1.5371(26〇C) CH?(4-CF30-Ph) 1.5077(25〇C) CH2(3-CF3S02NH-Ph) 161-162 i-Pr 1.4953(20〇C) CH(Et)2 59 (CH2)7-Me 1.4882(26〇C) CH(Me)-(CH7),-Me 1.4681(20〇C) -50- 200404764 通式（I — 4 )X R9 Physical properties [melting point Γ0, refractive index] 3-158 3-159 3-160 3-161 3-162 3-163 3-164 3-165 3-166 3-167 3-168 3-169 3-170 3-171 3-172 3-173 3-174 3-175 3-176 3-177 3-178 3-179 3-180 3-181 3-182 3-183 3-184 3-185 KTJ1 TT_ ^ TT- JX Jijl JITT-TT-Ti- Ti-TUJXJXTT-TT-Ti-Tl T1-TT-TT- thxja tt- jx ίτ ^ -ΑΤΓΡΤΓΡΤΓ * ΤΓΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΗΧΡΤΓ-ΤΓ-ΤΓ-ΤΓ-ΤΓ- τΓ-τΓ-τΓ-ΤΓΤΓΤΓΤΓ 3 3 3 3 3333333333333333333333 3 i FF F fffffffffffffffffffffffffcccccccccccccccccccccccccccc 22222222222222222222 2 2222222 e T ^ TUTHAJlJlJXCMTT-TT-JlJliJlJlTlTlTlJlJXTlJiTT-JlJXJXTT-TT- τγτγτγτγτγτγ- ^ ο ^ τγττ * τγ-τγ-ρτγ-τγ-τγ- τγ-τηατγ-τγ-ρτ ^ -τγ-τγ-τγ-τγ-τγ-τγ- 5 4-OMe-Ph 130-131 2-NHrPh 1.5316 (24〇C) 2-NHOH-Ph 1.5465 (24〇C) 2-NHAc-Ph 1.5241 (24〇C) 2,4-F2-Ph 112-113 2-Phthalimidyl-Ph 177-180 2-CF3-Ph 1.4936 (28〇C) 2-CFrPh 1.5327 (21 ° C) CH2CO -t-Bu 104-105 CH2COPh 1.5351 (23 ° C) CH2CO (254-ClrPh) 1.5494 (28 ° C) CONMe2 1.5099 (25 ° C) CHMeC02Me 1.4966 (27 ° C) CHMeCO? H 1.4989 (25 ° C) CHMeCONH (4-Cl-Ph) 90-95 CMer (3-i-Pr-Ph) 1.5129 (28 ° C) CH2 (2,4-ClrPh ) 49 CH2 (2-Me-Ph) 106-107 CH2 (3-Me-Ph) 1.5275 (23〇C) CH? (4-Me-Ph) 1.5431 (23〇C) CH2 (2,4-Me2- Ph) 30 CH2 (4-MeO-Ph) 1.5371 (26〇C) CH? (4-CF30-Ph) 1.5077 (25〇C) CH2 (3-CF3S02NH-Ph) 161-162 i-Pr 1.4953 (20〇 C) CH (Et) 2 59 (CH2) 7-Me 1.4882 (26〇C) CH (Me)-(CH7),-Me 1.4681 (20〇C) -50- 200404764 General formula (1-4)

第4表（m=0、A-CH^-G1 二0、J4=J5 = CH) No. 取代 位置 Rl R2 X R9 物性 〔融點（°C)〕 4-1 2 cf3 H H Me 4-2 2 cf3 H H t-Bu 4-3 2 cf3 H H -CH2-Ph 4-4 2 cf3 H H -CH?-(2-Cl-Ph) 4-5 2 cf3 H H -CH?-(2,6-Cl?-Ph) 4-6 2 cf3 H H -CHMe-Ph 4-7 2 cf3 H H -CHMe-(2-Cl-Ph) 4-8 2 cf3 H H -CHMe-(2,6-Cl2-Ph) 4-9 2 cf3 H H -CMe9-Ph 4-10 2 cf3 H H -CMe2-(2-Cl-Ph) 4-11 2 cf3 H H -CMe?-(2,6-Cl?-Ph) 4-12 2 cf3 H H Ph 4-13 2 cf3 H H 2-F-Ph 4-14 .2 cf3 H H 2-Cl-Ph 117.4 4-15 2 cf3 H H 3-Cl-Ph 4-16 2 cf3 H H 4-Cl-Ph 4-17 2 cf3 H H 2-Br-Ph 4-18 2 cf3 H H 2-I-Ph 4-19 2 cf3 H H 2-Me-Ph 4-20 2 cf3 H H 2-Et»Ph 4-21 2 cf3 H H 2-i-Pr-Ph 4-22 2 cf3 H H 2-OMe-Ph 4-23 2 cf3 H H 2-SMe-Ph 4-24 2 cf3 H H 2-SOMe-Ph 4-25 2 cf3 H H 2-SO?Me-Ph 4-26 2 cf3 H H 2-NCVPh 4-27 2 cf3 H H 2-CN-Ph 4-28 2 cf3 H H 2-CF3-Ph 4-29 2 cf3 H H 2-OCF3-Ph 4-30 2 cf3 H H 2-SCF3-Ph 4-31 2 CF, H H 2-SOCFrPhTable 4 (m = 0, A-CH ^ -G1, 0, J4 = J5 = CH) No. Substitution position Rl R2 X R9 Physical properties [melting point (° C)] 4-1 2 cf3 HH Me 4-2 2 cf3 HH t-Bu 4-3 2 cf3 HH -CH2-Ph 4-4 2 cf3 HH -CH?-(2-Cl-Ph) 4-5 2 cf3 HH -CH?-(2,6-Cl? -Ph) 4-6 2 cf3 HH -CHMe-Ph 4-7 2 cf3 HH -CHMe- (2-Cl-Ph) 4-8 2 cf3 HH -CHMe- (2,6-Cl2-Ph) 4-9 2 cf3 HH -CMe9-Ph 4-10 2 cf3 HH -CMe2- (2-Cl-Ph) 4-11 2 cf3 HH -CMe?-(2,6-Cl? -Ph) 4-12 2 cf3 HH Ph 4-13 2 cf3 HH 2-F-Ph 4-14 .2 cf3 HH 2-Cl-Ph 117.4 4-15 2 cf3 HH 3-Cl-Ph 4-16 2 cf3 HH 4-Cl-Ph 4-17 2 cf3 HH 2-Br-Ph 4-18 2 cf3 HH 2-I-Ph 4-19 2 cf3 HH 2-Me-Ph 4-20 2 cf3 HH 2-Et »Ph 4-21 2 cf3 HH 2-i- Pr-Ph 4-22 2 cf3 HH 2-OMe-Ph 4-23 2 cf3 HH 2-SMe-Ph 4-24 2 cf3 HH 2-SOMe-Ph 4-25 2 cf3 HH 2-SO? Me-Ph 4 -26 2 cf3 HH 2-NCVPh 4-27 2 cf3 HH 2-CN-Ph 4-28 2 cf3 HH 2-CF3-Ph 4-29 2 cf3 HH 2-OCF3-Ph 4-30 2 cf3 HH 2-SCF3 -Ph 4-31 2 CF, HH 2-SOCFrPh

-5 1- 200404764 第4表（續) No. 取代 位置 R1 R2 X R9 物性 〔融點（°C)〕 4-32 2 cf3 H H 2-SO，CFrPh 4-33 2 cf3 H H 2-CO?Me-Ph 4-34 2 cf3 H H 2-Ph-Ph 4-35 2 cf3 H H 4-PhO-Ph 4-36 2 cf3 H H 2,6-F?-Ph 4-37 2 cf3 H H 2,3-Cl7-Ph 4-38 2 cf3 H H 2,4-Cl9-Ph 4-39 2 cf3 H H 2,6-ClrPh 182.2 4-40 2 cf3 H H 2,6-Br2-Ph 4-41 2 cf3 H H 2,6-I9-Ph 4-42 2 cf3 H H 2,6-Me2-Ph 4-43 2 cf3 H H 2,6-EVPh 4-44 2 cf3 H H 2,6-(OMe)9-Ph 4-45 2 cf3 H H 2,6-(CF3)7-Ph 4-46 2 cf3 H H 2,6-(OCF3)7-Ph 4-47 2 cf3 H H 2,3,4-Cl3-Ph 4-48 2 cf3 H H 2,4,6-Cl3-Ph 4-49 2 cf3 H H 2,6-Cl7-4-CF3-Ph 4-50 2 cf3 H H 2,6-Clr4-OCFrPh 4-51 2 cf3 H H 2,4,6-Me,Ph 4-52 2 cf3 H H 2-Pyn 4-53 2 cf3 H H 3-Pyn 4-54 2 cf3 H H 4-Pyn 4-55 2 cf3 H H 6-Cl-2-Pyn 4-56 2 cf3 H H 6-CF3-2-Pyn 4-57 2 cf3 H H 6-Cl-4-CF3-2-Pyn 4-58 2 cf3 H H 2-Pym 4-59 2 cf3 H H 4-Pym 4-60 2 cf3 H H 4,6-Me2-2-Pym 4-61 2 cf3 H H 4,6-(OMe)7-2-Pym 4-62 2 cf3 H H -CO-NHMe 4-63 2 cf3 H H -CO-NHPh 4-64 2 cf3 H H -CO-NMePh 4-65 2 cf3 H H -CO-NEt(c-Hex) 4-66 2 CF, H H -CO-N(i-Pr)? 200404764-5 1- 200404764 Table 4 (continued) No. Substitution position R1 R2 X R9 Physical properties [melting point (° C)] 4-32 2 cf3 HH 2-SO, CFrPh 4-33 2 cf3 HH 2-CO? Me -Ph 4-34 2 cf3 HH 2-Ph-Ph 4-35 2 cf3 HH 4-PhO-Ph 4-36 2 cf3 HH 2,6-F? -Ph 4-37 2 cf3 HH 2,3-Cl7- Ph 4-38 2 cf3 HH 2,4-Cl9-Ph 4-39 2 cf3 HH 2,6-ClrPh 182.2 4-40 2 cf3 HH 2,6-Br2-Ph 4-41 2 cf3 HH 2,6-I9 -Ph 4-42 2 cf3 HH 2,6-Me2-Ph 4-43 2 cf3 HH 2,6-EVPh 4-44 2 cf3 HH 2,6- (OMe) 9-Ph 4-45 2 cf3 HH 2, 6- (CF3) 7-Ph 4-46 2 cf3 HH 2,6- (OCF3) 7-Ph 4-47 2 cf3 HH 2,3,4-Cl3-Ph 4-48 2 cf3 HH 2,4,6 -Cl3-Ph 4-49 2 cf3 HH 2,6-Cl7-4-CF3-Ph 4-50 2 cf3 HH 2,6-Clr4-OCFrPh 4-51 2 cf3 HH 2,4,6-Me, Ph 4 -52 2 cf3 HH 2-Pyn 4-53 2 cf3 HH 3-Pyn 4-54 2 cf3 HH 4-Pyn 4-55 2 cf3 HH 6-Cl-2-Pyn 4-56 2 cf3 HH 6-CF3-2 -Pyn 4-57 2 cf3 HH 6-Cl-4-CF3-2-Pyn 4-58 2 cf3 HH 2-Pym 4-59 2 cf3 HH 4-Pym 4-60 2 cf3 HH 4,6-Me2-2 -Pym 4-61 2 cf3 HH 4,6- (OMe) 7-2-Pym 4-62 2 cf3 HH -CO-NHMe 4-63 2 cf3 HH -CO-NHPh 4-64 2 cf3 H H -CO-NMePh 4-65 2 cf3 H H -CO-NEt (c-Hex) 4-66 2 CF, H H -CO-N (i-Pr)? 200404764

通式（I一 4)General formula (I-4)

R1-S02(R2)N U (I—4) 第5表（R1=cf3、 R2=H、 X=H :、J4=CH、J5=N ' Gl=0) No. 取代 位置 m G A R9 物性 〔融點（°c)〕 5-1 2 0 0 (ch2)2 Me 5-2 2 0 0 (ch2)2 t-Bu 5-3 2 0 0 (ch2)2 -CHrPh 5-4 2 0 0 (ch2)2 -CMe2-Ph 5-5 2 0 0 (ch2)2 Ph 5-6 2 0 0 (ch2)2 2-Cl-Ph 102-105 5-7 2 0 0 (ch2)2 2-Me-Ph 5-8 2 0 0 (ch2)2 2-OMe-Ph 5-9 2 0 〇 (ch2)2 2-CF3-Ph 5-10 2 0 o (ch2)2 2-OCF3-Ph 5-11 2 0 0 (ch2)2 2,6-Cl2-Ph 5-12 2 0 0 (ch2)2 2,6-Me2-Ph 5-13 2 0 0 (ch2)2 2-Pyn 5-14 2 0 0 (ch2)2 3-Pyn 5-15 2 0 0 (ch2)2 4-Pyn 5-16 2 0 0 (ch2)2 436-Me2-2-Pym 5-17 2 0 0 (ch2)2 4,6-(OMe)2~2-Pym 5-18 2 0 0 (ch2)2 3-Pyd 5-19 2 0 0 (ch2)2 -CO-NHMe 5-20 2 0 0 (ch2)2 -CO-NHPh 5-21 2 0 0 (ch2)2 -CO-NMePh 5-22 2 0 0 (ch2)2 -CO-NEt(c-Hex) 5-23 2 0 0 (ch2)2 -CO-N(i-Pr)2 5-24 2 0 0 CHMe Me -53- 200404764 第5表（續) No. 取代 位置 m G A R9 物性 5-25 2 0 0 CHMe t-Bu 5-26 2 0 〇 CHMe -CH2-Ph 5-27 2 0 0 CHMe -CMe2-Ph 5-28 2 0 0 CHMe Ph 5-29 2 0 〇 CHMe 2-Cl-Ph NMR-3 5-30 2 0 0 CHMe 2-Me-Ph 5-31 2 0 0 CHMe 2-OMe-Ph 5-32 2 0 0 CHMe 2-CF3-Ph 5-33 2 0 0 CHMe 2-OCF3-Ph 5-34 2 0 0 CHMe 2,6-Cl2-Ph 5-35 2 0 0 CHMe 2,6-Me2-Ph 5-36 2 0 〇 CHMe 2-Pyn 5-37 2 0 〇 CHMe 3-Pyn 5-38 2 0 0 CHMe 4-Pyn 5-39 2 0 0 CHMe 2-Pym 5-40 2 0 0 CHMe 4-Pym 5-41 2 0 0 CHMe 4,6-Mer2-Pym 5-42 2 0 〇 CHMe 4,6-(OMe)2-2-Pym 5-43 2 0 0 CHMe 3-Pyd 5-44 2 0 0 CHMe 6-Cl-3-Pyd 5-45 2 0 0 CH(OH)CH2 Me 5-46 2 0 0 CH(OH)CH2 t-Bu 5-47 2 0 0 CH(OH)CH2 -CHrPh 5-48 2 0 0 CH(OH)CH2 -CMe2-Ph 5-49 2 0 〇 CH(OH)CH2 Ph 5-50 2 0 0 CH(OH)CH2 2-Cl-Ph NMR-4 5-51 2 0 0 CH(OH)CH2 2,6-Cl2-Ph 5-52 2 0 0 CH(OH)CH2 2-Cl-6-F-Ph 5-53 2 0 0 CH(OH)CH2 2-Cl-6-Me-Ph 5-54 2 0 0 CH(OH)CH2 2,6-MerPh 5-55 2 0 0 CH(OH)CH2 2-Pym 5-56 2 0 0 CH(OH)CH2 4-Pym 5-57 2 0 0 CH(OH)CH2 4,6-Me2-2-Pym 5-58 2 0 0 CH(OH)CH2 4,6-(OMe)2-2-Pym 5-59 2 1 0 CH2 MeR1-S02 (R2) NU (I-4) Table 5 (R1 = cf3, R2 = H, X = H :, J4 = CH, J5 = N 'Gl = 0) No. Substitution position m GA R9 Physical properties [ Melting point (° c)] 5-1 2 0 0 (ch2) 2 Me 5-2 2 0 0 (ch2) 2 t-Bu 5-3 2 0 0 (ch2) 2 -CHrPh 5-4 2 0 0 ( ch2) 2 -CMe2-Ph 5-5 2 0 0 (ch2) 2 Ph 5-6 2 0 0 (ch2) 2 2-Cl-Ph 102-105 5-7 2 0 0 (ch2) 2 2-Me- Ph 5-8 2 0 0 (ch2) 2 2-OMe-Ph 5-9 2 0 〇 (ch2) 2 2-CF3-Ph 5-10 2 0 o (ch2) 2 2-OCF3-Ph 5-11 2 0 0 (ch2) 2 2,6-Cl2-Ph 5-12 2 0 0 (ch2) 2 2,6-Me2-Ph 5-13 2 0 0 (ch2) 2 2-Pyn 5-14 2 0 0 ( ch2) 2 3-Pyn 5-15 2 0 0 (ch2) 2 4-Pyn 5-16 2 0 0 (ch2) 2 436-Me2-2-Pym 5-17 2 0 0 (ch2) 2 4,6- (OMe) 2 ~ 2-Pym 5-18 2 0 0 (ch2) 2 3-Pyd 5-19 2 0 0 (ch2) 2 -CO-NHMe 5-20 2 0 0 (ch2) 2 -CO-NHPh 5 -21 2 0 0 (ch2) 2 -CO-NMePh 5-22 2 0 0 (ch2) 2 -CO-NEt (c-Hex) 5-23 2 0 0 (ch2) 2 -CO-N (i-Pr ) 2 5-24 2 0 0 CHMe Me -53- 200404764 Table 5 (continued) No. Substitution position m GA R9 Physical properties 5-25 2 0 0 CHMe t-Bu 5-26 2 0 〇CHMe -CH2-Ph 5 -27 2 0 0 CHMe -CMe2-Ph 5-28 2 0 0 CHMe Ph 5-29 2 0 〇CH Me 2-Cl-Ph NMR-3 5-30 2 0 0 CHMe 2-Me-Ph 5-31 2 0 0 CHMe 2-OMe-Ph 5-32 2 0 0 CHMe 2-CF3-Ph 5-33 2 0 0 CHMe 2-OCF3-Ph 5-34 2 0 0 CHMe 2,6-Cl2-Ph 5-35 2 0 0 CHMe 2,6-Me2-Ph 5-36 2 0 〇CHMe 2-Pyn 5-37 2 0 〇CHMe 3-Pyn 5-38 2 0 0 CHMe 4-Pyn 5-39 2 0 0 CHMe 2-Pym 5-40 2 0 0 CHMe 4-Pym 5-41 2 0 0 CHMe 4,6-Mer2-Pym 5 -42 2 0 〇CHMe 4,6- (OMe) 2-2-Pym 5-43 2 0 0 CHMe 3-Pyd 5-44 2 0 0 CHMe 6-Cl-3-Pyd 5-45 2 0 0 CH ( OH) CH2 Me 5-46 2 0 0 CH (OH) CH2 t-Bu 5-47 2 0 0 CH (OH) CH2 -CHrPh 5-48 2 0 0 CH (OH) CH2 -CMe2-Ph 5-49 2 0 〇CH (OH) CH2 Ph 5-50 2 0 0 CH (OH) CH2 2-Cl-Ph NMR-4 5-51 2 0 0 CH (OH) CH2 2,6-Cl2-Ph 5-52 2 0 0 CH (OH) CH2 2-Cl-6-F-Ph 5-53 2 0 0 CH (OH) CH2 2-Cl-6-Me-Ph 5-54 2 0 0 CH (OH) CH2 2,6- MerPh 5-55 2 0 0 CH (OH) CH2 2-Pym 5-56 2 0 0 CH (OH) CH2 4-Pym 5-57 2 0 0 CH (OH) CH2 4,6-Me2-2-Pym 5 -58 2 0 0 CH (OH) CH2 4,6- (OMe) 2-2-Pym 5-59 2 1 0 CH2 Me

-54- 200404764 第5表（續) No. 取代 位置 m G A R9 物性 5-60 2 1 0 ch2 t-Bu 5-61 2 1 〇 ch2 -CH2-Ph 5-62 2 1 0 ch2 -CMe2-Ph 5-63 2 1 0 ch2 Ph 5-64 2 1 0 ch2 2-Cl-Ph NMR-5 5-65 2 1 0 ch2 2-Me-Ph 5-66 2 1 0 ch2 2-OMe-Ph 5-67 2 1 0 ch2 2-CF3-Ph 5-68 2 1 0 ch2 2-OCF3-Ph 5-69 2 1 0 ch2 2,6-ClrPh 5-70 2 1 0 ch2 2-Cl-6-F~Ph 5-71 2 1 〇 ch2 2-Cl-6-Me-Ph 5-72 2 1 0 ch2 2,6-Me2-Ph 5-73 2 1 0 ch2 2-Pyn 5-74 2 1 0 ch2 3-Pyn 5-75 2 1 〇 ch2 4-Pyn 5-76 2 1 0 ch2 2-Pym 5-77 2 1 0 ch2 4-Pym 5-78 2 1 0 ch2 4,6-Me2-2-Pym 5-79 2 1 0 ch2 4?6-(OMe)r2-Pym 5-80 2 1 0 ch2 3-Pyd 5-81 2 1 0 ch2 -CO-NHMe 5-82 2 1 0 ch2 -CO-NHPh 5-83 2 1 〇 ch2 -CO-NH(2-Cl-Ph) 5-84 2 1 0 ch2 -CO-NMe2 5-85 2 1 0 ch2 -CO-NMePh 5-86 2 1 0 ch2 -CO-NEt(c-Hex) 5-87 2 1 0 ch2 -CO-N(i-Pr)2 5-88 2 1 N-OMe ch2 Me 5-89 2 1 N-OMe ch2 t-Bu 5-90 2 1 N-OMe ch2 -CH2-Ph 5-91 2 1 N-OMe ch2 -CMerPh-54- 200404764 Table 5 (continued) No. Substitution position m GA R9 Physical properties 5-60 2 1 0 ch2 t-Bu 5-61 2 1 〇ch2 -CH2-Ph 5-62 2 1 0 ch2 -CMe2-Ph 5-63 2 1 0 ch2 Ph 5-64 2 1 0 ch2 2-Cl-Ph NMR-5 5-65 2 1 0 ch2 2-Me-Ph 5-66 2 1 0 ch2 2-OMe-Ph 5-67 2 1 0 ch2 2-CF3-Ph 5-68 2 1 0 ch2 2-OCF3-Ph 5-69 2 1 0 ch2 2,6-ClrPh 5-70 2 1 0 ch2 2-Cl-6-F ~ Ph 5 -71 2 1 〇ch2 2-Cl-6-Me-Ph 5-72 2 1 0 ch2 2,6-Me2-Ph 5-73 2 1 0 ch2 2-Pyn 5-74 2 1 0 ch2 3-Pyn 5 -75 2 1 〇ch2 4-Pyn 5-76 2 1 0 ch2 2-Pym 5-77 2 1 0 ch2 4-Pym 5-78 2 1 0 ch2 4,6-Me2-2-Pym 5-79 2 1 0 ch2 4? 6- (OMe) r2-Pym 5-80 2 1 0 ch2 3-Pyd 5-81 2 1 0 ch2 -CO-NHMe 5-82 2 1 0 ch2 -CO-NHPh 5-83 2 1 〇 ch2 -CO-NH (2-Cl-Ph) 5-84 2 1 0 ch2 -CO-NMe2 5-85 2 1 0 ch2 -CO-NMePh 5-86 2 1 0 ch2 -CO-NEt (c-Hex) 5-87 2 1 0 ch2 -CO-N (i-Pr) 2 5-88 2 1 N-OMe ch2 Me 5-89 2 1 N-OMe ch2 t-Bu 5-90 2 1 N-OMe ch2 -CH2 -Ph 5-91 2 1 N-OMe ch2 -CMerPh

-55- 200404764-55- 200404764

第5表（續)Table 5 (continued)

No. 取代 位置 m G A R9 物性 5-92 2 1 N-OMe ch2 Ph 5-93 2 1 N-OMe ch2 2-Cl-Ph NMR-6 5-94 2 1 N-OMe ch2 2-Me-Ph 5-95 2 1 N-OMe ch2 2-OMe-Ph 5-96 2 1 N-OMe ch2 2-CF3-Ph 5-97 2 1 N-OMe ch2 2-OCF3-Ph 5-98 2 1 N-OMe ch2 2,6-Cl2-Ph 5-99 2 1 N-OMe ch2 2-Cl-6-F-Ph 5-100 2 1 N-OMe ch2 2-Cl-6-Me-Ph 5-101 2 1 N-OMe ch2 2,6-Me2-PhNo. Substitution position m GA R9 Physical properties 5-92 2 1 N-OMe ch2 Ph 5-93 2 1 N-OMe ch2 2-Cl-Ph NMR-6 5-94 2 1 N-OMe ch2 2-Me-Ph 5 -95 2 1 N-OMe ch2 2-OMe-Ph 5-96 2 1 N-OMe ch2 2-CF3-Ph 5-97 2 1 N-OMe ch2 2-OCF3-Ph 5-98 2 1 N-OMe ch2 2,6-Cl2-Ph 5-99 2 1 N-OMe ch2 2-Cl-6-F-Ph 5-100 2 1 N-OMe ch2 2-Cl-6-Me-Ph 5-101 2 1 N- OMe ch2 2,6-Me2-Ph

-56- 200404764 通式（I — 5)-56- 200404764 general formula (I — 5)

R1-S02(R2)NR1-S02 (R2) N

(1-5) 第6表（m=〇、A= - CH2 -、G【=0) N。·翌 R1 R2(1-5) Table 6 (m = 〇, A =-CH2-, G [= 0) N. · 翌 R1 R2

X J2 J3 R9 物性 〔融點（°C)〕 6-1 2 cf3 6-2 2 cf3 6-3 2 cf3 6-4 2 cf3 6-5 2 cf3 6-6 2 cf3 6-7 2 cf3 6-8 2 cf3 6-9 2 cf3 6-10 2 cf3 6-11 2 cf3 6-12 2 cf3 6-13 2 cf3 6-14 2 cf3 6-15 2 cf3 6-16 2 cf3 6-17 2 cf3 6-18 2 cf3 6-19 2 cf3 6-20 2 cf3 6-21 2 cf3 6-22 2 cf3 6-23 2 cf3 6-24 2 cf3 6-25 2 cf3 6-26 2 cf3 6-27 2 cf3 6-28 2 cf3 H H ch2 H H ch7 H H CH， H H CH， H H CH? H H CH， H H CH, H H CH， H H CH, H H CH? H H CH, H H CH， H H CH? H H ch7 H H ch7 H H CH, H H ch7 H H ch7 H H ch2 H H ch9 H H ch2 H H ch2 H H ch7 H H CH? H H CH, H H ch9 H H ch9 H H ch7 CH2 Me CH7 t-Bu CH; -CH7-Ph CH2 -CHMe-Ph CH2 -CMe?-Ph CH2 Ph CH9 2-F-Ph CH，2-Cl-Ph CH9 3-Cl-Ph CH, 4-Cl-Ph CHj 2-Me-Ph CH? 2-i-Pr-Ph CH7 2-OMe-Ph CH; 2-SMe-Ph CH7 2-SOMe-Ph CH; 2-S02Me-Ph CH? 2-CN-Ph CH; 2-NCVPh CH; 2-CF3:Ph CH2 2-OCF3-Ph CH2 2-SCF3-Ph CH? 2-SOCF3-Ph CH, 2-S02CF3-Ph CH? 2-CO?Me-Ph CH~ 2-Ph-Ph CH? 4-PhO-Ph CH，2,6-F2-Ph CH，2,6-Cl7-Ph .3.8.6 o 11 2 7 6 5 IX 11 11 125.8 146.2201.2 -57- 200404764 第6表（續) No. 取代 位置 R1 R2 X J2 J3 r9 物性 〔融點（°c)、折射率〕 6-29 2 cf3 H H CH, CH? 2,6-Me2-Ph 200.6 6-30 2 cf3 H H ch7 ch2 2?6-(CF3)2-Ph 6-31 2 cf3 H H ch2 CH2 236-(OCF3)2-Ph 6-32 2 cf3 H H ch2 CH? 2-Cl-6-Me-Ph 185.1 6-33 2 cf3 H H ch2 ch2 2,456-Cl3-Ph 144.3 6-34 2 cf3 H H CH? ch2 2,6-Cl7-4-CF3-Ph 6-35 2 cf3 H H CH? ch9 2,6-Cl2-4-OCF3-Ph 6-36 2 cf3 H H CH， CH? 2,3,4-Me3-Ph 6-37 2 CF3 H H ch7 ch2 2-Pyn 6-38 2 CF3 H H CH, ch2 3-Pyn 6-39 2 cf3 H H ch2 CH， 4-Pyn 6-40 2 cf3 H H ch9 CH， 6-Cl-2-Pyn 6-41 2 cf3 H H ch2 CH, 6-CF3-2-Pyn 6-42 2 cf3 H H ch2 ch2 6-Cl-4-CF3-2-Pyn 6-43 2 cf3 H H CH? ch7 2-Pym 6-44 2 cf3 H H ch2 ch2 4-Pym 6-45 2 cf3 H H ch7 CH7 4,6-Me?-2-Pym 6-46 2 cf3 H H ch2 CK2 4,6-(OMe)2-2-Pym 6-47 2 cf3 H H ch2 CH， 3-Pyd 6-48 2 cf3 H H ch7 CH, 6-Cl-3-Pyd 6-49 2 cf3 H H ch2 ch2 -CO-NHMe 6-50 2 cf3 H H CH? ch2 -CO-NHPh 6-51 2 cf3 H H ch7 ch7 -CO-NMePh 6-52 2 cf3 H H ch7 CH， -CO-NEt, 6-53 2 cf3 H H CH， CH, -CO-NEt(c-Hex) 6-54 2 cf3 H H ch2 CH, -CO-N(i-Pr)? 6-55 2 cf3 H H ch2 C=0 Me 6-56 2 cf3 H H CH, C=0 t-Bu 6-57 2 CF3 H H CH， C=0 -CH7-Ph 6-58 2 cf3 H H CH? C=0 -CHMe-Ph 6-59 2 cf3 H H ch2 C=0 -CMe2-Ph 6-60 2 cf3 H H ch2 C=0 Ph 1.5561(24〇C) 6-61 2 cf3 H H ch2 C=0 2-F-Ph 6-62 2 cf3 H H ch2 C=0 2-Cl-Ph 150.5-151.7 6-63 2 cf3 H H ch9 C=0 2-Br-Ph 6-64 2 cf3 H H ch9 C=0 2-I-Ph 6-65 2 cf3 H H CH? C=0 2-Me-Ph 6-66 2 cf3 H H CH， c=o 2-i-Pr-Ph 6-67 2 cf3 H H CH， c=o 2-OMe-Ph 6-68 2 cf3 H H CH? oo 2-SMe-Ph 6-69 2 CF, H H CH, c=o 2-SOMe-Ph 200404764 第6表（續) No. 取代 位置 R1 r2 X J2 J3 物性 〔融點（°c)、折射率〕 6-70 2 cf3 H H ch7 c=o 2-SO?Me-Ph 6-71 2 cf3 H H CH? c=o 2-CN-Ph 6-72 2 cf3 H H ch2 c=o 2-N02-Ph 6-73 2 cf3 H H ch2 c=o 2-CF3-Ph L5140(24〇C) 6-74 2 cf3 H H CH? c=o 2-OCF3-Ph 6-75 2 cf3 H H CH? c=o 2-SCF3-Ph 6-76 2 cf3 H H CH? c=o 2-SOCF3-Ph 6-77 2 cf3 H H CH? c=o 2-S02CFrPh 6-78 2 cf3 H H CH, c=o 2-CO?Me-Ph 6-79 2 cf3 H H ch7 c=o 2-Ph-Ph 6-80 2 cf3 H H CH? c=o 4-PhO-Ph 6-81 2 cf3 H H ch2 c=o 2,6-F2-Ph 6-82 2 cf3 H H CH， c=o 2,6-Cl2-Ph 196.7-198.0 6-83 2 cf3 H H CH， c=o 2,6-MerPh 172.9 6-84 2 cf3 H H ch2 oo 2,6-(CF3)2-Ph 6-85 2 cf3 H H ch2 c=o 2,6-(OCF3)2_Ph 6-86 2 cf3 H H ch7 c=o 2,3,4-Cl3-Ph 6-87 2 cf3 H H ch2 c=o 2,4,6-Cl3-Ph 6-88 2 cf3 H H CH? c=o 2,6-Cl?-4-CF3-Ph 6-89 2 cf3 H H CU2 c=o 2,6-Cl;-4-OCF3-Ph 6-90 2 cf3 H H ch2 c=o 253,4-Me3-Ph 6-91 2 cf3 H H CH? c=o 2-Pyn 6-92 2 cf3 H H ch2 c=o 3-Pyn 6-93 2 cf3 H H CH? c=o 4-Pyn 6-94 2 cf3 H H CH? oo 6-Cl-2-Pyn 6-95 2 cf3 H H CH? c=o 6-CF3-2-Pyn 6-96 2 cf3 H H ch7 c=o 6-Cl-4-CF3-2-Pyn 6-97 2 cf3 H H CH; c=o 2-Pym 6-98 2 cf3 H H CH， c=o 4-Pym 6-99 2 cf3 H H CH? c=o 4,6-Mer2-Pym 6-100 2 cf3 H H CH; c=o 4,6-(OMe)2-2-Pym 6-101 2 cf3 H H CH? c=o 3-Pyd — 6-102 2 cf3 H H ch7 c=o 6-Cl-3-Pyd 6-103 2 cf3 H H ch2 oo -CO-NHMe 6-104 2 cf3 H H ch7 c=o -CO-NHPh 6-105 2 cf3 H H ch2 c=o -CO-NMePh 6-106 2 cf3 H H ch2 c=o -CO-NEt(c-Hex) 6-107 2 cf3 H H ch2 c=o -CO-N(i-Pr)7 6-108 2 cf3 H H C=0 CH? Me 6-109 2 CF, H H C=0 CH， t-BuX J2 J3 R9 Physical properties [melting point (° C)] 6-1 2 cf3 6-2 2 cf3 6-3 2 cf3 6-4 2 cf3 6-5 2 cf3 6-6 2 cf3 6-7 2 cf3 6- 8 2 cf3 6-9 2 cf3 6-10 2 cf3 6-11 2 cf3 6-12 2 cf3 6-13 2 cf3 6-14 2 cf3 6-15 2 cf3 6-16 2 cf3 6-17 2 cf3 6- 18 2 cf3 6-19 2 cf3 6-20 2 cf3 6-21 2 cf3 6-22 2 cf3 6-23 2 cf3 6-24 2 cf3 6-25 2 cf3 6-26 2 cf3 6-27 2 cf3 6- 28 2 cf3 HH ch2 HH ch7 HH CH, HH CH, HH CH? HH CH, HH CH, HH CH, HH CH, HH CH? HH CH, HH CH, HH CH? HH ch7 HH ch7 HH CH, HH ch7 HH ch7 HH ch2 HH ch9 HH ch2 HH ch2 HH ch7 HH CH? HH CH, HH ch9 HH ch9 HH ch7 CH2 Me CH7 t-Bu CH; -CH7-Ph CH2 -CHMe-Ph CH2 -CMe? -Ph CH2 Ph CH9 2 -F-Ph CH, 2-Cl-Ph CH9 3-Cl-Ph CH, 4-Cl-Ph CHj 2-Me-Ph CH? 2-i-Pr-Ph CH7 2-OMe-Ph CH; 2-SMe -Ph CH7 2-SOMe-Ph CH; 2-S02Me-Ph CH? 2-CN-Ph CH; 2-NCVPh CH; 2-CF3: Ph CH2 2-OCF3-Ph CH2 2-SCF3-Ph CH? 2- SOCF3-Ph CH, 2-S02CF3-Ph CH? 2-CO? Me-Ph CH ~ 2-Ph-Ph CH? 4-PhO-Ph CH, 2,6-F2-Ph CH, 2,6-Cl7- Ph .3.8.6 o 11 2 7 6 5 IX 11 11 125.8 146.2201.2 -57- 200404764 Table 6 (continued) No. Substituted position R1 R2 X J2 J3 r9 Physical properties [melting point (° c), refractive index] 6-29 2 cf3 HH CH, CH? 2,6-Me2-Ph 200.6 6-30 2 cf3 HH ch7 ch2 2? 6- (CF3) 2-Ph 6-31 2 cf3 HH ch2 CH2 236- (OCF3) 2-Ph 6-32 2 cf3 HH ch2 CH ? 2-Cl-6-Me-Ph 185.1 6-33 2 cf3 HH ch2 ch2 2,456-Cl3-Ph 144.3 6-34 2 cf3 HH CH? Ch2 2,6-Cl7-4-CF3-Ph 6-35 2 cf3 HH CH? Ch9 2,6-Cl2-4-OCF3-Ph 6-36 2 cf3 HH CH, CH? 2,3,4-Me3-Ph 6-37 2 CF3 HH ch7 ch2 2-Pyn 6-38 2 CF3 HH CH, ch2 3-Pyn 6-39 2 cf3 HH ch2 CH, 4-Pyn 6-40 2 cf3 HH ch9 CH, 6-Cl-2-Pyn 6-41 2 cf3 HH ch2 CH, 6-CF3-2- Pyn 6-42 2 cf3 HH ch2 ch2 6-Cl-4-CF3-2-Pyn 6-43 2 cf3 HH CH? Ch7 2-Pym 6-44 2 cf3 HH ch2 ch2 4-Pym 6-45 2 cf3 HH ch7 CH7 4,6-Me? -2-Pym 6-46 2 cf3 HH ch2 CK2 4,6- (OMe) 2-2-Pym 6-47 2 cf3 HH ch2 CH, 3-Pyd 6-48 2 cf3 HH ch7 CH, 6-Cl-3-Pyd 6-49 2 cf3 HH ch2 ch2 -CO-NHMe 6-50 2 cf3 HH CH? Ch2 -CO-NHPh 6-51 2 cf3 HH ch7 ch7 -CO-NMePh 6-52 2cf3 HH ch7 CH, -CO-NEt, 6-53 2 cf3 HH CH, CH, -CO-NEt (c-Hex) 6-54 2 cf3 HH ch2 CH, -CO-N (i-Pr)? 6- 55 2 cf3 HH ch2 C = 0 Me 6-56 2 cf3 HH CH, C = 0 t-Bu 6-57 2 CF3 HH CH, C = 0 -CH7-Ph 6-58 2 cf3 HH CH? C = 0- CHMe-Ph 6-59 2 cf3 HH ch2 C = 0 -CMe2-Ph 6-60 2 cf3 HH ch2 C = 0 Ph 1.5561 (24〇C) 6-61 2 cf3 HH ch2 C = 0 2-F-Ph 6 -62 2 cf3 HH ch2 C = 0 2-Cl-Ph 150.5-151.7 6-63 2 cf3 HH ch9 C = 0 2-Br-Ph 6-64 2 cf3 HH ch9 C = 0 2-I-Ph 6-65 2 cf3 HH CH? C = 0 2-Me-Ph 6-66 2 cf3 HH CH, c = o 2-i-Pr-Ph 6-67 2 cf3 HH CH, c = o 2-OMe-Ph 6-68 2 cf3 HH CH? Oo 2-SMe-Ph 6-69 2 CF, HH CH, c = o 2-SOMe-Ph 200404764 Table 6 (continued) No. Substituted position R1 r2 X J2 J3 Properties [melting point (° c), refractive index) 6-70 2 cf3 HH ch7 c = o 2-SO? Me-Ph 6-71 2 cf3 HH CH? c = o 2-CN-Ph 6-72 2 cf3 HH ch2 c = o 2 -N02-Ph 6-73 2 cf3 HH ch2 c = o 2-CF3-Ph L5140 (24〇C) 6-74 2 cf3 HH CH? C = o 2-OCF3-Ph 6-75 2 cf3 HH CH? C = o 2-SCF3-Ph 6-76 2 cf3 HH CH? c = o 2-SOCF3-Ph 6-77 2 cf3 HH CH? c = o 2-S02CFrPh 6-78 2 cf3 HH CH, c = o 2-CO? Me-Ph 6-79 2 cf3 HH ch7 c = o 2-Ph-Ph 6-80 2 cf3 HH CH? c = o 4 -PhO-Ph 6-81 2 cf3 HH ch2 c = o 2,6-F2-Ph 6-82 2 cf3 HH CH, c = o 2,6-Cl2-Ph 196.7-198.0 6-83 2 cf3 HH CH, c = o 2,6-MerPh 172.9 6-84 2 cf3 HH ch2 oo 2,6- (CF3) 2-Ph 6-85 2 cf3 HH ch2 c = o 2,6- (OCF3) 2_Ph 6-86 2 cf3 HH ch7 c = o 2,3,4-Cl3-Ph 6-87 2 cf3 HH ch2 c = o 2,4,6-Cl3-Ph 6-88 2 cf3 HH CH? C = o 2,6-Cl? -4-CF3-Ph 6-89 2 cf3 HH CU2 c = o 2,6-Cl; -4-OCF3-Ph 6-90 2 cf3 HH ch2 c = o 253,4-Me3-Ph 6-91 2 cf3 HH CH? C = o 2-Pyn 6-92 2 cf3 HH ch2 c = o 3-Pyn 6-93 2 cf3 HH CH? C = o 4-Pyn 6-94 2 cf3 HH CH? Oo 6-Cl-2 -Pyn 6-95 2 cf3 HH CH? C = o 6-CF3-2-Pyn 6-96 2 cf3 HH ch7 c = o 6-Cl-4-CF3-2-Pyn 6-97 2 cf3 HH CH; c = o 2-Pym 6-98 2 cf3 HH CH, c = o 4-Pym 6-99 2 cf3 HH CH? c = o 4,6-Mer2-Pym 6-100 2 cf3 HH CH; c = o 4, 6- (OMe) 2-2-Pym 6-101 2 cf3 HH CH? C = o 3-Pyd — 6-102 2 cf3 HH ch7 c = o 6-Cl-3-Pyd 6-103 2 cf3 HH ch2 oo -CO-NHMe 6-104 2 cf3 HH ch7 c = o -CO-NHPh 6-105 2 cf3 HH ch2 c = o -CO-NMePh 6-106 2 cf3 HH ch2 c = o -CO-NEt (c-Hex) 6-107 2 cf3 HH ch2 c = o -CO-N (i-Pr) 7 6-108 2 cf3 HHC = 0 CH? Me 6-109 2 CF, HHC = 0 CH, t-Bu

-59- 200404764 第6表（續）-59- 200404764 Table 6 (Continued)

No. RlNo. Rl

RlRl

X J2 J3 R9 物性〔融點（°C)〕 6-110 6-111 6-112 6-113 6-114 6-115 6-116 6-117 6-118 6-119 6-120 6-121 6-122 6-123 6-124 6-125 6-126 6-127 6-128 6-129 6-130 6-131 6-132 6-133 6-134 6-135 6-136 6-137 6-138 6-139 6-140 6-141 6-142 6-143 6-144 6-145 6-146 6-147 6-148 6-149 6-150 6-151 3 3 3 3 3 3 33333333333333 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 31 fffffffffffffffffffffffffffff.f:f:f:f:f:f:f:f:f:f:f:f:f cccccccccccccccccccccccccccccccccccccccccc 222222222222222222222222222222222222222222 H c=o CH? -CH7-Ph H c=o ch2 -CHMe-Ph H C=0 CH, -CMe9-Ph H 〇〇 ch9 Ph H C=0 CH? 2-Cl-Ph H C=0 CH? 2-Me-Ph H C=0 ch2 2-OMe-Ph H 〇〇 CH, 2-SMe-Ph H C=0 ch9 2-SOMe-Ph H C=0 ch2 2-SO?Me-Ph H C=0 ch2 2-CN-Ph H c=o ch2 2-NOrPh H C=0 ch2 2-CF3-Ph H C=0 ch2 2-OCF3-Ph H c=o CH， 2-SCF3-Ph H c=o ch7 2-SOCF3-Ph H c=o CH， 2-S09CF3-Ph H c=o CH? 2-C07Me-Ph H oo CH， 2-Ph-]Ph H c=o ch2 2-PhO-Ph H c=o CH? 2,6-F2-Ph H c=o ch2 2,6-Cl，-Ph H CO ch2 2,6-MerPh H c=o CH? 2,3,4-ClrPh H c=o CH， 2,4,6-Cl3-Ph H c=o CH? 2,6-Cl，-4-CF3-Ph H c=o CH, 2,6-Cl2-4-OCF3-Ph H oo CH， 2,3,4-Me3-Ph H c=o ch7 2-Pyn H c=o CH， 3-Pyn H c=o ch2 4-Pyn H oo CH2 6-Cl-2-Pyn H oo CH， 6-CF3-2-Pyn H c=o ch2 6-Cl-4-CF3-2-Pyn H c=o CH2 2-Pym H oo ch2 4-Pym H oo CH2 4,6-Mer2-Pym H c=o ch2 4,6-(OMe)7-2-Pym H c=o CH? 3-Pyd " H c=o CH? 6-Cl-3-Pyd H oo ch2 -CO-NHMe H c=o CH， -CO-NHPh 96.9-115.3 -60- 200404764 第6表（續) No. 取代 位置 R1 R2 X J2 J3 R9 物性 6-152 2 cf3 H H C=0 ch2 -C0-NH-2-Cl-Ph 6-153 2 cf3 H H C=0 CH? -CO-NMePh 6-154 2 cf3 H H C=0 CH? -CO-NEt(c-Hex) 6-155 2 cf3 H H C=0 ch7 -C0-N(i-Pr)2 6-156 2 cf3 H H c=o C=0 Me 6-157 2 cf3 H H c=o c=o t-Bu 6-158 2 cf3 H H c=o c=o -CH2-Ph 6-159 2 cf3 H H c=o c=o -CHMe-Ph 6-160 2 cf3 H H oo c=o -CMe,-Ph 6-161 2 cf3 H H c=o c=o Ph 6-162 2 cf3 H H oo c=o 2-F-Ph 6-163 2 cf3 H H c=o c=o 2-Cl-Ph 6-164 2 cf3 H H c=o c=o 2-Me-Ph 6-165 2 cf3 H H c=o c=o 2-i-Pr-Ph 6-166 2 cf3 H H c=o c=o 2-OMe-Ph 6-167 2 cf3 H H oo c=o 2-SMe-Ph 6-168 2 cf3 H H c=o c=o 2-SOMe-Ph 6-169 2 cf3 H H c=o c=o 2-S02Me-Ph 6-170 2 cf3 H H c=o oo 2-CN-Ph 6-171 2 cf3 H H c=o C=0 2-N02-Ph 6-172 2 cf3 H H c=o c=o 2-CF3-Ph 6-173 2 cf3 H H c=o C=0 2-OCF3-Ph 6-174 2 cf3 H H c=o oo 2-SCF3-Ph 6-175 2 cf3 H H c=o oo 2-SOCF3-Ph 6-176 2 cf3 H H c=o c=o 2-SO,CF3-Ph 6-177 2 cf3 H H c=o c=o 2-CO;Me-Ph 6-178 2 cf3 H H oo c=o 2-Ph-Ph 6-179 2 cf3 H H c=o c=o 2-PhO-Ph 6-180 2 cf3 H H c=o C=0 2,6-F，-Ph 6-181 2 cf3 H H oo OO 2,6-d-Ph 6-182 2 cf3 H H c=o C=0 2,6-Br9-Ph 6-183 2 cf3 H H oo C=0 256-I9-Ph 6-184 2 cf3 H H oo C=0 2,6-Me?-Ph 6-185 2 cf3 H H oo C=0 2,6-(OMe)rPh 6-186 2 cf3 H H c=o C=0 2,6-(CF3)2-Ph 6-187 2 cf3 H H c=o C=0 2,6-(OCF3)7-Ph 6-188 2 cf3 H H oo C=0 2,3,4-ClrPii 6-189 2 cf3 H H CO C=0 2,4,6-Cl3-Ph 6-190 2 cf3 H H c=o OO 2,6-Cl2-4-CF3-Ph 6-191 2 cf3 H H oo C=0 2,6-Cl2-4-OCF3-Ph 6-192 2 cf3 H H oo C=0 2?3,4-Me3-Ph 6-193 2 cf3 H H c=o C=0 2-PynX J2 J3 R9 Physical properties [melting point (° C)] 6-110 6-111 6-112 6-113 6-114 6-115 6-116 6-117 6-118 6-119 6-120 6-121 6 -122 6-123 6-124 6-125 6-126 6-127 6-128 6-129 6-130 6-131 6-132 6-133 6-134 6-135 6-136 6-137 6-138 6-139 6-140 6-141 6-142 6-143 6-144 6-145 6-146 6-147 6-148 6-149 6-150 6-151 3 3 3 3 3 33333333333333 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 CH? -CH7-Ph H c = o ch2 -CHMe-Ph HC = 0 CH, -CMe9-Ph H 〇〇ch9 Ph HC = 0 CH? 2-Cl-Ph HC = 0 CH? 2-Me-Ph HC = 0 ch2 2-OMe-Ph H 〇〇CH, 2-SMe-Ph HC = 0 ch9 2-SOMe-Ph HC = 0 ch2 2-SO? Me-Ph HC = 0 ch2 2-CN-Ph H c = o ch2 2-NOrPh HC = 0 ch2 2-CF3-Ph HC = 0 ch2 2-OCF3-Ph H c = o CH, 2-SCF3-Ph H c = o ch7 2-SOCF3-Ph H c = o CH, 2-S09CF3-Ph H c = o CH? 2-C07Me-Ph H oo CH, 2-Ph-] Ph H c = o ch2 2-PhO-Ph H c = o CH? 2,6-F2-Ph H c = o ch2 2,6-Cl, -Ph H CO ch2 2,6-MerPh H c = o CH? 2,3,4-ClrPh H c = o CH, 2,4,6-Cl3-Ph H c = o CH? 2,6-Cl, -4-CF3-Ph H c = o CH, 2,6-Cl2-4-OCF3-Ph H oo CH, 2,3,4-Me3-Ph H c = o ch7 2-Pyn H c = o CH, 3-Pyn H c = o ch2 4-Pyn H oo CH2 6-Cl-2-Pyn H oo CH, 6-CF3-2-Pyn H c = o ch2 6-Cl-4-CF3-2-Pyn H c = o CH2 2-Pym H oo ch2 4-Pym H oo CH2 4,6-Mer2-Pym H c = o ch2 4,6- (OMe) 7-2-Pym H c = o CH? 3-Pyd " H c = o CH? 6-Cl-3-Pyd H oo ch2 -CO-NHMe H c = o CH, -CO-NHPh 96.9-115.3 -60- 200404764 Table 6 (continued) No. Substitution position R1 R2 X J2 J3 R9 Physical properties 6-152 2 cf3 HHC = 0 ch2 -C0-NH-2-Cl-Ph 6-153 2 cf3 HHC = 0 CH? -CO-NMePh 6-154 2 cf3 HHC = 0 CH? -CO-NEt (c-Hex) 6-155 2 cf3 HHC = 0 ch7 -C0-N (i-Pr ) 2 6-156 2 cf3 HH c = o C = 0 Me 6-157 2 cf3 HH c = oc = o t-Bu 6-158 2 cf3 HH c = oc = o -CH2-Ph 6-159 2 cf3 HH c = oc = o -CHMe-Ph 6-160 2 cf3 HH oo c = o -CMe, -Ph 6-161 2 cf3 HH c = oc = o Ph 6-162 2 cf3 HH oo c = o 2-F- Ph 6-163 2 cf3 HH c = oc = o 2-Cl-Ph 6-164 2 cf3 HH c = oc = o 2-Me-Ph 6-165 2 cf3 HH c = oc = o 2-i-Pr- Ph 6-166 2 cf3 HH c = oc = o 2-OMe-Ph 6-167 2 cf3 HH oo c = o 2-SMe-Ph 6-168 2 cf3 HH c = oc = o 2-SOMe-Ph 6-169 2 cf3 HH c = oc = o 2- S02Me-Ph 6-170 2 cf3 HH c = o oo 2-CN-Ph 6-171 2 cf3 HH c = o C = 0 2-N02-Ph 6-172 2 cf3 HH c = oc = o 2-CF3- Ph 6-173 2 cf3 HH c = o C = 0 2-OCF3-Ph 6-174 2 cf3 HH c = o oo 2-SCF3-Ph 6-175 2 cf3 HH c = o oo 2-SOCF3-Ph 6- 176 2 cf3 HH c = oc = o 2-SO, CF3-Ph 6-177 2 cf3 HH c = oc = o 2-CO; Me-Ph 6-178 2 cf3 HH oo c = o 2-Ph-Ph 6 -179 2 cf3 HH c = oc = o 2-PhO-Ph 6-180 2 cf3 HH c = o C = 0 2,6-F, -Ph 6-181 2 cf3 HH oo OO 2,6-d-Ph 6-182 2 cf3 HH c = o C = 0 2,6-Br9-Ph 6-183 2 cf3 HH oo C = 0 256-I9-Ph 6-184 2 cf3 HH oo C = 0 2,6-Me? -Ph 6-185 2 cf3 HH oo C = 0 2,6- (OMe) rPh 6-186 2 cf3 HH c = o C = 0 2,6- (CF3) 2-Ph 6-187 2 cf3 HH c = o C = 0 2,6- (OCF3) 7-Ph 6-188 2 cf3 HH oo C = 0 2,3,4-ClrPii 6-189 2 cf3 HH CO C = 0 2,4,6-Cl3-Ph 6-190 2 cf3 HH c = o OO 2,6-Cl2-4-CF3-Ph 6-191 2 cf3 HH oo C = 0 2,6-Cl2-4-OCF3-Ph 6-192 2 cf3 HH oo C = 0 2? 3,4-Me3-Ph 6-193 2 cf3 HH c = o C = 0 2-Pyn

-61- 200404764 第6表（續) No. 取代 位置 R1 R2 X J2 J3 R9 物性 6-194 2 cf3 H H C=0 C=0 3-Pyn 6-195 2 cf3 H H C=0 C=0 4-Pyn 6-196 2 cf3 H H CO C=0 6-Cl-2-Pyn 6-197 2 cf3 H H C=0 OO 6-CF3-2-Pyn 6-198 2 GF3 H H c=o C=0 6-Cl-4-CF3-2-Pyn 6-199 2 cf3 H H c=o C=0 2-Pym 6-200 2 cf3 H H c=o C=0 4-Pym 6-201 2 cf3 H , H c=o OO 4,6-Me2-2-Pym 6-202 2 cf3 H H c=o C=0 4,6-(OMe),-2-Pym 6-203 2 cf3 H H c=o C=0 3-Pyd 6-204 2 cf3 H H c=o C=0 6-Cl-3-Pyd 6-205 2 cf3 H H CO C=0 -CO-NHMe 6-206 2 cf3 H H c=o OO -CO-NHPh 6-207 2 cf3 H H c=o c=o -CO-NMePh 6-208 2 cf3 H H c=o C=0 -CO-NEt(c-Hex) 6-209 2 cf3 H H c=o C=0 -C0-N(i-Pr)2 6-210 2 cf3 H H ch2 NH Me 6-211 2 cf3 H H ch2 NH t-Bu 6-212 2 cf3 H H CH? NH -CH2-Ph 6-213 2 cf3 H H CH? NH -CHMe-Ph 6-214 2 cf3 H H ch7 NH -CMe9-Ph 6-215 2 cf3 H H CH， NH Ph 6-216 2 cf3 H H CH; NH 2-F-Ph 6-217 2 cf3 H H CH， NH 2-Cl-Ph 6-218 2 cf3 H H CH? NH 2-Me-Ph 6-219 2 cf3 H H ch2 NH 2-i-Pr-Ph 6-220 2 cf3 H H CH? NH 2-OMe-Ph 6-221 2 cf3 H H ch2 NH 2-SMe-Ph 6-222 2 cf3 H H CH， NH 2-SOMe-Ph 6-223 2 cf3 H H CH? NH 2-S02Me-Ph 6-224 2 cf3 H H ch2 NH 2-CN-Ph 6-225 2 cf3 H H ch7 NH 2-N07-Ph 6-226 2 cf3 H H ch7 NH 2-CF3-Ph 6-227 2 cf3 H H ch7 NH 2-OCF3-Ph 6-228 2 cf3 H H ch9 NH 2-SCF3-Ph 6-229 2 cf3 H H ch2 NH 2-SOCF3-Ph 6-230 2 cf3 H H ch7 NH 2-SO,CF3-Ph 6-231 2 cf3 H H CH， NH 2-C02Me-Ph 6-232 2 cf3 H H CH? NH 2-Ph-Ph 6-233 2 cf3 H H CH, NH 2-PhO-Ph 6-234 2 cf3 H H CH， NH 2,6-F2-Ph 6-235 2 CF, H H CH? NH 2,6-CU-Ph 200404764 第6表（續)-61- 200404764 Table 6 (continued) No. Substitution position R1 R2 X J2 J3 R9 Physical properties 6-194 2 cf3 HHC = 0 C = 0 3-Pyn 6-195 2 cf3 HHC = 0 C = 0 4-Pyn 6 -196 2 cf3 HH CO C = 0 6-Cl-2-Pyn 6-197 2 cf3 HHC = 0 OO 6-CF3-2-Pyn 6-198 2 GF3 HH c = o C = 0 6-Cl-4- CF3-2-Pyn 6-199 2 cf3 HH c = o C = 0 2-Pym 6-200 2 cf3 HH c = o C = 0 4-Pym 6-201 2 cf3 H, H c = o OO 4,6 -Me2-2-Pym 6-202 2 cf3 HH c = o C = 0 4,6- (OMe),-2-Pym 6-203 2 cf3 HH c = o C = 0 3-Pyd 6-204 2 cf3 HH c = o C = 0 6-Cl-3-Pyd 6-205 2 cf3 HH CO C = 0 -CO-NHMe 6-206 2 cf3 HH c = o OO -CO-NHPh 6-207 2 cf3 HH c = oc = o -CO-NMePh 6-208 2 cf3 HH c = o C = 0 -CO-NEt (c-Hex) 6-209 2 cf3 HH c = o C = 0 -C0-N (i-Pr) 2 6-210 2 cf3 HH ch2 NH Me 6-211 2 cf3 HH ch2 NH t-Bu 6-212 2 cf3 HH CH? NH -CH2-Ph 6-213 2 cf3 HH CH? NH -CHMe-Ph 6-214 2 cf3 HH ch7 NH -CMe9-Ph 6-215 2 cf3 HH CH, NH Ph 6-216 2 cf3 HH CH; NH 2-F-Ph 6-217 2 cf3 HH CH, NH 2-Cl-Ph 6-218 2 cf3 HH CH? NH 2-Me-Ph 6-219 2 cf3 HH ch2 NH 2-i-Pr-Ph 6-220 2 cf3 HH CH? NH 2-OMe-Ph 6-221 2 cf3 HH ch2 NH 2-SMe-Ph 6-222 2 cf3 HH CH, NH 2-SOMe-Ph 6-223 2 cf3 HH CH? NH 2-S02Me-Ph 6-224 2 cf3 HH ch2 NH 2-CN-Ph 6-225 2 cf3 HH ch7 NH 2-N07-Ph 6-226 2 cf3 HH ch7 NH 2-CF3-Ph 6-227 2 cf3 HH ch7 NH 2-OCF3-Ph 6 -228 2 cf3 HH ch9 NH 2-SCF3-Ph 6-229 2 cf3 HH ch2 NH 2-SOCF3-Ph 6-230 2 cf3 HH ch7 NH 2-SO, CF3-Ph 6-231 2 cf3 HH CH, NH 2 -C02Me-Ph 6-232 2 cf3 HH CH? NH 2-Ph-Ph 6-233 2 cf3 HH CH, NH 2-PhO-Ph 6-234 2 cf3 HH CH, NH 2,6-F2-Ph 6- 235 2 CF, HH CH? NH 2,6-CU-Ph 200404764 Table 6 (continued)

No. 取代 位置 R1 R2 X J2 J3 R9 物性 6-236 2 cf3 H H ch2 NH 2,6-Me2-Ph 6-237 2 cf3 H H ch2 NH 2,6-(OMe)?-Ph 6-238 2 cf3 H H ch2 NH 2,6-(CF3)7-Ph 6-239 2 cf3 H H CH? NH 2,3,4-Cl,Ph 6-240 2 cf3 H H ch7 NH 2,4,6-Cl3-Ph 6-241 2 cf3 H H ch7 NH 2,6-Cl?-4-CF3-Ph 6-242 2 cf3 H H ch2 NH 2,6-Cl;-4-OCF3-Ph 6-243 2 cf3 H H ch7 NH 2,3?4-Me3-Ph 6-244 2 cf3 H H ch7 NH 2-Pyn 6-245 2 cf3 H H ch7 NH 3-Pyn 6-246 2 cf3 H H ch7 NH 4-Pyn 6-247 2 cf3 H H CH， NH 6-Cl-2-Pyn 6-248 2 cf3 H H ch2 NH 6-CF3-2-Pyn 6-249 2 cf3 H H ch2 NH 6-Cl-4-CF3-2-Pyn 6-250 2 cf3 H H CH， NH 2-Pym 6-251 2 cf3 H H CH? NH 4-Pym 6-252 2 cf3 H H ch7 NH 4?6-Me?-2-Pym 6-253 2 cf3 H H ch9 NH 4,6-(OMe)?-2-Pym 6-254 2 cf3 H H ch2 NH 3-Pyd 6-255 2 cf3 H H ch7 NH 6-Cl-3-Pyd 6-256 2 cf3 H H ch7 NH -CO-NHMe 6-257 2 cf3 H H ch7 NH -CO-NHPh 6-258 2 cf3 H H ch2 NH -CO-NMePh 6-259 2 cf3 H H ch7 NH -CO-NEt, 6-260 2 cf3 H H ch2 NH -CO-NEt(c-Hex) 6-261 2 cf3 H H CH, NH -CO-N(i-Pr), 6-262 2 cf3 H H ch2 N-Me Me 6-263 2 cf3 H H ch9 N-Me t-Bu 6-264 2 cf3 H H ch7 N-Me -CH，-Ph 6-265 2 cf3 H H CH, N-Me -CHMe-Ph 6-266 2 cf3 H H ch7 N-Me -CMe2-Ph 6-267 2 cf3 H H ch9 N-Me Ph 6-268 2 cf3 H H CH? N-Me 2-F-Ph 6-269 2 cf3 H H CH， N-Me 2-Cl-Ph 6-270 2 cf3 H H CH， N-Me 2-Me-Ph 6-271 2 cf3 H H CH? N-Me 2-i-Pr-Ph 6-272 2 cf3 H H CH, N-Me 2-OMe-Ph 6-273 2 cf3 H H CH， N-Me 2-SMe-Ph 6-274 2 cf3 H H ch7 N-Me 2-SOMe-Ph 6-275 2 cf3 H H ch9 N-Me 2-S02Me-Ph 6-276 2 cf3 H H ch2 N-Me 2-CN-Ph 6-277 2 cf3 H H CH， N-Me 2-NCVPhNo. Substitution position R1 R2 X J2 J3 R9 Physical properties 6-236 2 cf3 HH ch2 NH 2,6-Me2-Ph 6-237 2 cf3 HH ch2 NH 2,6- (OMe)?-Ph 6-238 2 cf3 HH ch2 NH 2,6- (CF3) 7-Ph 6-239 2 cf3 HH CH? NH 2,3,4-Cl, Ph 6-240 2 cf3 HH ch7 NH 2,4,6-Cl3-Ph 6-241 2 cf3 HH ch7 NH 2,6-Cl? -4-CF3-Ph 6-242 2 cf3 HH ch2 NH 2,6-Cl; -4-OCF3-Ph 6-243 2 cf3 HH ch7 NH 2,3? 4 -Me3-Ph 6-244 2 cf3 HH ch7 NH 2-Pyn 6-245 2 cf3 HH ch7 NH 3-Pyn 6-246 2 cf3 HH ch7 NH 4-Pyn 6-247 2 cf3 HH CH, NH 6-Cl- 2-Pyn 6-248 2 cf3 HH ch2 NH 6-CF3-2-Pyn 6-249 2 cf3 HH ch2 NH 6-Cl-4-CF3-2-Pyn 6-250 2 cf3 HH CH, NH 2-Pym 6 -251 2 cf3 HH CH? NH 4-Pym 6-252 2 cf3 HH ch7 NH 4? 6-Me? -2-Pym 6-253 2 cf3 HH ch9 NH 4,6- (OMe)?-2-Pym 6 -254 2 cf3 HH ch2 NH 3-Pyd 6-255 2 cf3 HH ch7 NH 6-Cl-3-Pyd 6-256 2 cf3 HH ch7 NH -CO-NHMe 6-257 2 cf3 HH ch7 NH -CO-NHPh 6 -258 2 cf3 HH ch2 NH -CO-NMePh 6-259 2 cf3 HH ch7 NH -CO-NEt, 6-260 2 cf3 HH ch2 NH -CO-NEt (c-Hex) 6-261 2 cf3 HH CH, NH -CO-N (i-Pr), 6-262 2 cf3 HH ch2 N-Me Me 6-263 2 cf3 HH ch9 N-Me t-Bu 6-264 2 cf3 HH ch7 N-Me -CH, -Ph 6-265 2 cf3 HH CH, N-Me -CHMe-Ph 6-266 2 cf3 HH ch7 N-Me -CMe2-Ph 6-267 2 cf3 HH ch9 N-Me Ph 6-268 2 cf3 HH CH? N-Me 2-F-Ph 6-269 2 cf3 HH CH, N -Me 2-Cl-Ph 6-270 2 cf3 HH CH, N-Me 2-Me-Ph 6-271 2 cf3 HH CH? N-Me 2-i-Pr-Ph 6-272 2 cf3 HH CH, N -Me 2-OMe-Ph 6-273 2 cf3 HH CH, N-Me 2-SMe-Ph 6-274 2 cf3 HH ch7 N-Me 2-SOMe-Ph 6-275 2 cf3 HH ch9 N-Me 2- S02Me-Ph 6-276 2 cf3 HH ch2 N-Me 2-CN-Ph 6-277 2 cf3 HH CH, N-Me 2-NCVPh

-63- 200404764 第6表（續)-63- 200404764 Table 6 (Continued)

No. 取代 位置 R1 R2 X J2 J3 R9 物性 6-278 2 cf3 H H CH， N-Me 2-CF3-Ph 6-279 2 cf3 H H ca N-Me 2-OCF3-Ph 6-280 2 cf3 H H CH, N-Me 2-SCF3-Ph 6-281 2 cf3 H H ch2 N-Me 2-SOCFrPh 6-282 2 cf3 H H ch2 N-Me 2-S02CF3-Ph 6-283 2 cf3 H H ch7 N-Me 2 - CO，Me-Ph 6-284 2 cf3 H H CH， N-Me 2-Ph-Ph 6-285 2 cf3 H H ch7 N-Me 2-PhO-Ph 6-286 2 cf3 H H CH， N-Me 2,6-FrPh 6-287 2 cf3 H H CH? N-Me 2,6-Cl2-Ph 6-288 2 cf3 H H ch2 N-Me 2,6-Me?-Ph 6-289 2 cf3 H H CH? N-Me 2,6-(OMe)?-Ph 6-290 2 cf3 H H ch2 N-Me 2,6-(CF3)2-Ph 6-291 2 cf3 H H CH， N-Me 2,6-(OCF3),-Ph 6-292 2 cf3 H H CH? N-Me 2,354-Cl3-Ph 6-293 2 cf3 H H ch2 N-Me 2,4,6-Cl3-Ph 6-294 2 cf3 H H CH， N-Me 2,6-Cl2-4-CF3-Ph 6-295 2 cf3 H H CH; N-Me 256-Cl?-4-OCF3-Ph 6-296 2 cf3 H H CH， N-Me 2,3,4-Me3-Ph 6-297 2 cf3 H H ch2 N-Me 2-Pyn 6-298 2 cf3 H H ch2 N-Me 3-Pyn 6-299 2 cf3 H H CH? N-Me 4-Pyn 6-300 2 CF3 H H ch2 N-Me 6-Cl-2-Pyn 6-301 2 cf3 H H CH， N-Me 6-CF3-2-Pyn 6-302 2 cf3 H H ch2 N-Me 6-Cl-4-CF3-2-Pyn 6-303 2 cf3 H H ch2 N-Me 2-Pym 6-304 2 cf3 H H CH; N-Me 4-Pym 6-305 2 cf3 H H CH, N-Me 4,6-Me2-2-Pym 6-306 2 cf3 H H ch7 N-Me 4,6-(OMe)2-2-Pym 6-307 2 cf3 H H ch2 N-Me 3-Pyd ** 6-308 2 CF3 H H CH? N-Me 6-Cl-3-Pyd 6-309 2 cf3 H H CH, N-Me -CO-NHMe 6-310 2 cf3 H H ch2 N-Me -CO-NHPh 6-311 2 cf3 H H ch2 N-Me -CO-NMePh 6-312 2 cf3 H H ch7 N-Me -CO-NE^ 6-313 2 cf3 H H ch2 N-Me -CO-NEt(c-Hex) 6-314 2 cf3 H H ch2 N-Me -CO-N(i-Pr), 6-315 3 cf3 H H ch2 CH， Ph 6-316 3 CF, H H ch9 CH? 2-F-PhNo. Substitution position R1 R2 X J2 J3 R9 Physical properties 6-278 2 cf3 HH CH, N-Me 2-CF3-Ph 6-279 2 cf3 HH ca N-Me 2-OCF3-Ph 6-280 2 cf3 HH CH, N-Me 2-SCF3-Ph 6-281 2 cf3 HH ch2 N-Me 2-SOCFrPh 6-282 2 cf3 HH ch2 N-Me 2-S02CF3-Ph 6-283 2 cf3 HH ch7 N-Me 2-CO, Me-Ph 6-284 2 cf3 HH CH, N-Me 2-Ph-Ph 6-285 2 cf3 HH ch7 N-Me 2-PhO-Ph 6-286 2 cf3 HH CH, N-Me 2,6-FrPh 6-287 2 cf3 HH CH? N-Me 2,6-Cl2-Ph 6-288 2 cf3 HH ch2 N-Me 2,6-Me? -Ph 6-289 2 cf3 HH CH? N-Me 2,6 -(OMe)?-Ph 6-290 2 cf3 HH ch2 N-Me 2,6- (CF3) 2-Ph 6-291 2 cf3 HH CH, N-Me 2,6- (OCF3),-Ph 6- 292 2 cf3 HH CH? N-Me 2,354-Cl3-Ph 6-293 2 cf3 HH ch2 N-Me 2,4,6-Cl3-Ph 6-294 2 cf3 HH CH, N-Me 2,6-Cl2- 4-CF3-Ph 6-295 2 cf3 HH CH; N-Me 256-Cl? -4-OCF3-Ph 6-296 2 cf3 HH CH, N-Me 2,3,4-Me3-Ph 6-297 2 cf3 HH ch2 N-Me 2-Pyn 6-298 2 cf3 HH ch2 N-Me 3-Pyn 6-299 2 cf3 HH CH? N-Me 4-Pyn 6-300 2 CF3 HH ch2 N-Me 6-Cl- 2-Pyn 6-301 2 cf3 HH CH, N-Me 6-CF3-2-Pyn 6-302 2 cf3 HH ch2 N-Me 6-Cl-4-CF3-2-Pyn 6-303 2 cf3 HH ch2 N-Me 2-Pym 6-304 2 cf3 HH CH; N-Me 4-Pym 6-305 2 cf3 HH CH, N-Me 4 , 6-Me2-2-Pym 6-306 2 cf3 HH ch7 N-Me 4,6- (OMe) 2-2-Pym 6-307 2 cf3 HH ch2 N-Me 3-Pyd ** 6-308 2 CF3 HH CH? N-Me 6-Cl-3-Pyd 6-309 2 cf3 HH CH, N-Me -CO-NHMe 6-310 2 cf3 HH ch2 N-Me -CO-NHPh 6-311 2 cf3 HH ch2 N -Me -CO-NMePh 6-312 2 cf3 HH ch7 N-Me -CO-NE ^ 6-313 2 cf3 HH ch2 N-Me -CO-NEt (c-Hex) 6-314 2 cf3 HH ch2 N-Me -CO-N (i-Pr), 6-315 3 cf3 HH ch2 CH, Ph 6-316 3 CF, HH ch9 CH? 2-F-Ph

-64- 200404764 第6表（續）-64- 200404764 Table 6 (Continued)

No. 取代 位置No. Replaced Position

Rl R2Rl R2

X J2 J3 R9 物性 〔融點（°C)、折射率〕 6-317 3 cf3 H 6-318 3 cf3 H 6-319 3 cf3 H 6-320 3 cf3 H 6-321 3 cf3 H 6-322 3 cf3 H 6-323 3 cf3 H 6-324 3 cf3 H 6-325 3 cf3 H 6-326 3 cf3 H 6-327 4 cf3 H 6-328 4 cf3 H 6-329 4 cf3 H 6-330 4 cf3 H 6-331 4 cf3 H 6-332 4 cf3 H 6-333 4 cf3 H 6-334 4 cf3 H 6-335 4 cf3 H 6-336 4 cf3 H 6-337 4 cf3 H 6-338 4 cf3 H 6-339 2 cf3 H 6-340 2 cf3 H 6-341 2 cf3 H 6-342 2 cf3 i-Pr-CO 6-343 2 cf3 H 6-344 2 cf3 c-Pr-CO 6-345 2 cf3 i-Pr-CO 6-346 2 cf3 H 6-347 2 cf3 t-Bu-CO 6-348 2 cf3 Ph-CO 6-349 2 cf3 H 6-350 2 cf3 i-Pr-CO 6-351 2 cf3 i-Pr-CO 6-352 2 cf3 i-Pr-CO 6-353 2 cf3 H 6-354 2 cf3 i-Pr-CO 6-355 2 cf3 H 6-356 2 cf3 i-Pr-CO 6-357 2 CF, i-Pr-CO ίίίίίίίίίίίίίίίίίίίίίί^ίίίίί TT-TT-TUT1JXJXTT- τγτηχρτγτγτγτγτγτγτγτ^χτγ-τγ-τγτγ-τγ-τγρτγ-τ^χτηχτηα - tTr-Tr-THAt ΤΓΤΓΤΓΤΓΤ^ΧΤΓΤΓ ΤΓΤΓΡΤΓΤΓΤΓX J2 J3 R9 Physical properties [melting point (° C), refractive index] 6-317 3 cf3 H 6-318 3 cf3 H 6-319 3 cf3 H 6-320 3 cf3 H 6-321 3 cf3 H 6-322 3 cf3 H 6-323 3 cf3 H 6-324 3 cf3 H 6-325 3 cf3 H 6-326 3 cf3 H 6-327 4 cf3 H 6-328 4 cf3 H 6-329 4 cf3 H 6-330 4 cf3 H 6-331 4 cf3 H 6-332 4 cf3 H 6-333 4 cf3 H 6-334 4 cf3 H 6-335 4 cf3 H 6-336 4 cf3 H 6-337 4 cf3 H 6-338 4 cf3 H 6- 339 2 cf3 H 6-340 2 cf3 H 6-341 2 cf3 H 6-342 2 cf3 i-Pr-CO 6-343 2 cf3 H 6-344 2 cf3 c-Pr-CO 6-345 2 cf3 i-Pr -CO 6-346 2 cf3 H 6-347 2 cf3 t-Bu-CO 6-348 2 cf3 Ph-CO 6-349 2 cf3 H 6-350 2 cf3 i-Pr-CO 6-351 2 cf3 i-Pr -CO 6-352 2 cf3 i-Pr-CO 6-353 2 cf3 H 6-354 2 cf3 i-Pr-CO 6-355 2 cf3 H 6-356 2 cf3 i-Pr-CO 6-357 2 CF, i-Pr-CO ίίίίίίίίίίίίίίίίίίίίίί ^ ίίίίί TT-TT-TUT1JXJXTT- τγτηχρτγτγτγτγτγτγτγτ ^ χτγ-τγ-τγτγ-τγ-τγρτγ-τ ^ χτηχτηα - tTr-Tr-THAt ΤΓΤΓΤΓΤΓΤ ^ ΧΤΓΤΓ ΤΓΤΓΡΤΓΤΓΤΓ

Hr?- wi- HrV L 一 乙 L k k』vJT* vJT* WT- c-』込 k Q h k L L k HHHHHHHHHHHHHHHHHHHHHHHeHHHHHHHHicicHHHHHHH cccccccccccccccccccccccMeccccccccMeMeccccccc -Ή Ή 2-Cl-Ph 2.6- F?-Ph 2.6- Cl?-Ph 2.6- Me9-Ph 236-(CF3)7-Ph 2.3.4- Cl3-Ph 2.4.6- ClrPh 2.6- Cl7-4-CF3-Ph 2.6- Cl?-4-OCF3-Ph 2?3,4-Me3-PhHr?-Wi- HrV L One B L kk 『vJT * vJT * WT- c-』 込 k Q hk LL k HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHicicHHHHHHH cccccccccccccccccccccccMeccccPcc-Pcc-ccccPcc-ccccPcc-CccccPcc -Me9-Ph 236- (CF3) 7-Ph 2.3.4- Cl3-Ph 2.4.6- ClrPh 2.6- Cl7-4-CF3-Ph 2.6- Cl? -4-OCF3-Ph 2? 3,4-Me3 -Ph

Ph 2-F-Ph 2-Cl-Ph 2.6- F?-Ph 2.6- ClrPh 2.6- Me,-Ph 256-(CF3)7-Ph 2.3.4- Cl3-Ph 2.4.6- Cl3-Ph 2.6- Cl2-4-CF3-Ph 2.6- Clr4-OCF3-Ph 2.3.4- Me3-Ph 2-Cl-Ph 2.6- Cl2-Ph 4-Br-2,6-Me2-Ph 4-Br-2,6-Me2-Ph 4-Br-2-CF3-Ph 4-Br-2,6-Me2-Ph 2-C1-6 - Me-Ph 2.6- Cl广 Ph 4-Br-2:6-MerPh 4-Br-2,6-Me2-Ph 2.6- Cl2-Ph 2.6- Cl2-Ph 2.6- Cl2-Ph 2-Cl-Ph 4-Br-2-Me-Ph 4-Br-2-Me-Ph 4-Cl-2-Me-Ph 4-Cl-2-Me-Ph 2.6- Cl7-PhPh 2-F-Ph 2-Cl-Ph 2.6- F? -Ph 2.6- ClrPh 2.6- Me, -Ph 256- (CF3) 7-Ph 2.3.4- Cl3-Ph 2.4.6- Cl3-Ph 2.6- Cl2-4-CF3-Ph 2.6- Clr4-OCF3-Ph 2.3.4- Me3-Ph 2-Cl-Ph 2.6- Cl2-Ph 4-Br-2,6-Me2-Ph 4-Br-2,6- Me2-Ph 4-Br-2-CF3-Ph 4-Br-2,6-Me2-Ph 2-C1-6-Me-Ph 2.6- ClWh 4-Br-2: 6-MerPh 4-Br- 2,6-Me2-Ph 2.6- Cl2-Ph 2.6- Cl2-Ph 2.6- Cl2-Ph 2-Cl-Ph 4-Br-2-Me-Ph 4-Br-2-Me-Ph 4-Cl-2 -Me-Ph 4-Cl-2-Me-Ph 2.6- Cl7-Ph

NMR-8 180.3- 182.0 200.8 1.5249(2 l〇C) 175.3 1.5369(21〇C) 1.5241(22〇C) 166.8-167.7 # 150.5 57.3- 64.1 172.4- 173.3 51.7-66.8 1.5375(22〇C) 1.5367(22〇C) 158.1 1.5371(21〇C) 158.0-161.9 47.3- 60.0 1.5381(22〇C) -65- 200404764 第6表（續）NMR-8 180.3- 182.0 200.8 1.5249 (2 lOC) 175.3 1.5369 (21 ° C) 1.5241 (22 ° C) 166.8-167.7 # 150.5 57.3- 64.1 172.4- 173.3 51.7-66.8 1.5375 (22 ° C) 1.5367 (22 〇C) 158.1 1.5371 (21〇C) 158.0-161.9 47.3- 60.0 1.5381 (22〇C) -65- 200404764 Table 6 (continued)

No. 取代 位置 R1 R2 X J2 J3 R9 物丨生 〔融點（°C) 折射率〕 6-358 6-359 6-360 6-361 6-362 6-363 6-364 6-365 6-366 6-367 6-368 6-369 6-370 6-371 6-372 6-373 6-374 6-375 6-376 6-377 6-378 6-379 6-380 6-381 6-382 6-383 2222222 222 22 222222 2 2222222No. Substitute position R1 R2 X J2 J3 R9 〔Production〕 (melting point (° C) refractive index) 6-358 6-359 6-360 6-361 6-362 6-363 6-364 6-365 6-366 6-367 6-368 6-369 6-370 6-371 6-372 6-373 6-374 6-375 6-376 6-377 6-378 6-379 6-380 6-381 6-382 6- 383 2222222 222 22 222222 2 2222222

2 333333333333333333 3 3333『T _ 3 7. fffffff fff f f ffffff f FFFFilFFcccccccccccccccccc c CCCCCHCC2 333333333333333333 3 3333 『T _ 3 7. fffffff fff f f ffffff f FFFFilFFcccccccccccccccccc c CCCCCHCC

MHe MeOCH2 2,4,6-Me3-Ph-CO 2,6-Me7-Ph-CO Ph-CO i-BuO-CO n-BuO-CO MeO-CO EtO-CO PhO-CO n-Pr-CO n-Bu-CO i-Bu-CO 4-Cl-Ph-CO i-Pr Et-CO 4-Me-Ph-CO CH?=CH(CH?)?- CO 4-CF3-Ph-CO 2,4-F?-Ph-CO Ph-Ph-CO 2-Me-Ph-CO H H H 5-Cl-2-Me-Ph 167.5 2,6-Cl2-Ph 123-124 2,6-Cl2-Ph 1.5403(27〇C) 2,6-Cl?-Ph NMR-9 2,6-Cl;-Ph NMR-10 2,6-ClrPh 95-97 2,6-ClrPh 1.5232(21〇C) 2,6-ClrPh 1.5335(22〇C) 2,6-Cl2-Ph 126-128 2,6-ClrPh 1.5290(21°C) 2,6-ClrPh 1.5479(25〇C) 256-Cl2-Ph 1.5345(25〇C) 2,6-Cl2-Ph 1.5341(25〇C) 2,6-Cl^Ph 127.0-128.0 2,6-Cl2-Ph 134-138 2,6-Cl2-Ph 159-161 2,6-Cl2-Ph 1.5370(29〇C) 2,6-Cl2-Ph 118-121 2,6-Cl2-Ph 98-100 2?6-Cl?-Ph 141-145 2,6-Cl?-Ph 119-122 2,6-Cl，-Ph 125-128 2,6-Cl2-Ph 143-146 2,6-Cl，-Ph 176.5 Ph 132-134 Me 44-46 -66- 200404764 通式（I — 6)MHe MeOCH2 2,4,6-Me3-Ph-CO 2,6-Me7-Ph-CO Ph-CO i-BuO-CO n-BuO-CO MeO-CO EtO-CO PhO-CO n-Pr-CO n -Bu-CO i-Bu-CO 4-Cl-Ph-CO i-Pr Et-CO 4-Me-Ph-CO CH? = CH (CH?)?-CO 4-CF3-Ph-CO 2,4 -F? -Ph-CO Ph-Ph-CO 2-Me-Ph-CO HHH 5-Cl-2-Me-Ph 167.5 2,6-Cl2-Ph 123-124 2,6-Cl2-Ph 1.5403 (27 〇C) 2,6-Cl? -Ph NMR-9 2,6-Cl; -Ph NMR-10 2,6-ClrPh 95-97 2,6-ClrPh 1.5232 (21〇C) 2,6-ClrPh 1.5335 (22 ° C) 2,6-Cl2-Ph 126-128 2,6-ClrPh 1.5290 (21 ° C) 2,6-ClrPh 1.5479 (25 ° C) 256-Cl2-Ph 1.5345 (25 ° C) 2, 6-Cl2-Ph 1.5341 (25 ° C) 2,6-Cl ^ Ph 127.0-128.0 2,6-Cl2-Ph 134-138 2,6-Cl2-Ph 159-161 2,6-Cl2-Ph 1.5370 ( 29〇C) 2,6-Cl2-Ph 118-121 2,6-Cl2-Ph 98-100 2? 6-Cl? -Ph 141-145 2,6-Cl? -Ph 119-122 2,6- Cl, -Ph 125-128 2,6-Cl2-Ph 143-146 2,6-Cl, -Ph 176.5 Ph 132-134 Me 44-46 -66- 200404764 General formula (I-6)

第7表（R2=H 、R14=H、 m=〇 、A=_ CH2 -Ό^Ο) No. 取代 位置 Rl X J4 R13 物性 7-1 2 cf3 H CH Me 7-2 2 cf3 H CH t-Bu 7-3 2 cf3 H CH -CH2-Ph 7-4 2 cf3 H CH -CHMe-Ph 7-5 2 cf3 H CH -CMe,-Ph 7-6 2 cf3 H CH Ph 7-7 2 CF3 H CH 2-F-Ph 7-8 2 cf3 H CH 2-Cl-Ph 7-9 2 cf3 H CH 3-Cl-Ph 7-10 2 cf3 H CH 4-Cl-Ph 7-11 2 cf3 H CH 2-Br-Ph 7-12 2 cf3 H CH 2-I-Ph 7-13 2 cf3 H CH 2-Me-Ph 7-14 2 cf3 H CH 2-i-Pr-Ph 7-15 2 cf3 H CH 2-OMe-Ph 7-16 2 cf3 H CH 2-SMe-Ph 7-17 2 cf3 H CH 2-SOMe-Ph 7-18 2 cf3 H CH 2-SO?Me-Ph 7-19 2 cf3 H CH 2-CN-Ph 7-20 2 cf3 H CH 2-NO,-Ph 7-21 2 CF3 H CH 2-CF3-Ph 7-22 2 CF, H CH 2-OCF,-PhTable 7 (R2 = H, R14 = H, m = 〇, A = _ CH2 -Ό ^ Ο) No. Substitution position Rl X J4 R13 Physical properties 7-1 2 cf3 H CH Me 7-2 2 cf3 H CH t -Bu 7-3 2 cf3 H CH -CH2-Ph 7-4 2 cf3 H CH -CHMe-Ph 7-5 2 cf3 H CH -CMe, -Ph 7-6 2 cf3 H CH Ph 7-7 2 CF3 H CH 2-F-Ph 7-8 2 cf3 H CH 2-Cl-Ph 7-9 2 cf3 H CH 3-Cl-Ph 7-10 2 cf3 H CH 4-Cl-Ph 7-11 2 cf3 H CH 2 -Br-Ph 7-12 2 cf3 H CH 2-I-Ph 7-13 2 cf3 H CH 2-Me-Ph 7-14 2 cf3 H CH 2-i-Pr-Ph 7-15 2 cf3 H CH 2 -OMe-Ph 7-16 2 cf3 H CH 2-SMe-Ph 7-17 2 cf3 H CH 2-SOMe-Ph 7-18 2 cf3 H CH 2-SO? Me-Ph 7-19 2 cf3 H CH 2 -CN-Ph 7-20 2 cf3 H CH 2-NO, -Ph 7-21 2 CF3 H CH 2-CF3-Ph 7-22 2 CF, H CH 2-OCF, -Ph

-67- 200404764 第7表（續) No. 取代 位置 R1 X J4 R13 物丨生 〔融點（°C)〕 7-23 2 cf3 H CH 2-SCFrPh 7-24 2 cf3 H CH 2-SOCF3-Ph 7-25 2 cf3 H CH 2-SO?CF3-Ph 7-26 2 cf3 H CH 2-CO:Me-Ph 7-27 2 cf3 H CH 2-Ph-Ph 7-28 2 cf3 H CH 2-PhO-Ph 7-29 2 cf3 H CH 2,6-F,-Ph 7-30 2 cf3 H CH 2,6-Cl,-Ph 7-31 2 cf3 H CH 2,6-Me7-Ph 7-32 2 cf3 H CH 2?6-(OMe),-Ph 7-33 2 cf3 H CH 2,6-(CF3)2;Ph 7-34 2 cf3 H CH 2,6-(OCF3),-Ph 7-35 2 cf3 H CH 2,354-Cl3-Ph 7-36 2 cf3 H CH 2,4,6-Cl3-Ph 7-37 2 cf3 H CH 2,6-Cl7-4-CF3-Ph 7-38 2 cf3 H CH 2,6-Cl?-4-OCF3-Ph 7-39 2 cf3 H CH 2,3?4-Me3-Ph 7-40 2 cf3 H CH 2-Pyn 7-41 2 cf3 H CH 3-Pyn 7-42 2 cf3 H CH 4-Pyn 7-43 2 cf3 H CH 6-Cl-2-Pyn 7-44 2 CF3 H CH 6-CF3-2-Pyn 7-45 2 cf3 H CH 6-Cl-4-CF3-2-.Pyn 7-46 2 cf3 H CH 2-Pym 7-47 2 cf3 H CH 4-Pym 7-48 2 cf3 H CH 4,6-Me2-2-Pym 7-49 2 cf3 H CH 456-(OMe)9-2-Pym 7-50 2 cf3 H CH 3-Pyd 7-51 2 cf3 H CH -CO-NHMe 7-52 2 cf3 H CH -CO-NHPh 7-53 2 cf3 H CH -CO-NMePh 7-54 2 cf3 H CH -CO-NEt-(c-Hex) 7-55 2 cf3 H N Me 7-56 2 cf3 H N t-Bu 7-57 2 cf3 H N -CH,-Ph 7-58 2 cf3 H N -CHMe-Ph 7-59 2 cf3 H N -CMe?-Ph 7-60 2 cf3 H N Ph 123.8 7-61 2 cf3 H N 2-F-Ph 7-62 2 CF, H N 2-Cl-Ph-67- 200404764 Table 7 (continued) No. Substituted position R1 X J4 R13 Material [Melting point (° C)] 7-23 2 cf3 H CH 2-SCFrPh 7-24 2 cf3 H CH 2-SOCF3- Ph 7-25 2 cf3 H CH 2-SO? CF3-Ph 7-26 2 cf3 H CH 2-CO: Me-Ph 7-27 2 cf3 H CH 2-Ph-Ph 7-28 2 cf3 H CH 2- PhO-Ph 7-29 2 cf3 H CH 2,6-F, -Ph 7-30 2 cf3 H CH 2,6-Cl, -Ph 7-31 2 cf3 H CH 2,6-Me7-Ph 7-32 2 cf3 H CH 2? 6- (OMe),-Ph 7-33 2 cf3 H CH 2,6- (CF3) 2; Ph 7-34 2 cf3 H CH 2,6- (OCF3),-Ph 7- 35 2 cf3 H CH 2,354-Cl3-Ph 7-36 2 cf3 H CH 2,4,6-Cl3-Ph 7-37 2 cf3 H CH 2,6-Cl7-4-CF3-Ph 7-38 2 cf3 H CH 2,6-Cl? -4-OCF3-Ph 7-39 2 cf3 H CH 2,3? 4-Me3-Ph 7-40 2 cf3 H CH 2-Pyn 7-41 2 cf3 H CH 3-Pyn 7 -42 2 cf3 H CH 4-Pyn 7-43 2 cf3 H CH 6-Cl-2-Pyn 7-44 2 CF3 H CH 6-CF3-2-Pyn 7-45 2 cf3 H CH 6-Cl-4- CF3-2-.Pyn 7-46 2 cf3 H CH 2-Pym 7-47 2 cf3 H CH 4-Pym 7-48 2 cf3 H CH 4,6-Me2-2-Pym 7-49 2 cf3 H CH 456 -(OMe) 9-2-Pym 7-50 2 cf3 H CH 3-Pyd 7-51 2 cf3 H CH -CO-NHMe 7-52 2 cf3 H CH -CO-NHPh 7-53 2 cf3 H CH -CO -NMePh 7-54 2 cf3 H CH -CO-NEt- (c-Hex) 7-55 2 cf3 HN Me 7-56 2 cf3 HN t-Bu 7-57 2 cf3 HN -CH, -Ph 7-58 2 cf3 HN -CHMe- Ph 7-59 2 cf3 HN -CMe? -Ph 7-60 2 cf3 HN Ph 123.8 7-61 2 cf3 HN 2-F-Ph 7-62 2 CF, HN 2-Cl-Ph

-68- 200404764 第7表（續) No. 取代 位置 R1 X J4 R13 物性 7-63 2 cf3 H N 3-Cl-Ph 7-64 2 cf3 H N 4-Cl-Ph 7-65 2 cf3 H N 2-Me-Ph 7-66 2 cf3 H N 2-i-Pr-Ph 7-67 2 cf3 H N 2-OMe-Ph 7-68 2 cf3 H N 2-SMe-Ph 7-69 2 cf3 H N 2-SOMe-Ph 7-70 2 cf3 H N 2-SO?Me-Ph 7-71 2 cf3 H N 2-CN-Ph 7-72 2 cf3 H N 2-NO，-Ph 7-73 2 CF3 H N 2-CF3-Ph . 7-74 2 cf3 H N 2-OCF3-Ph 7-75 2 cf3 H N 2-SCF3-Ph 7-76 2 cf3 H N 2-SOCF3-Ph 7-77 2 cf3 H N 2-S02CF3-Ph 7-78 2 cf3 H N 2-C02Me-Ph 7-79 2 cf3 H N 2-Ph-Ph 7-80 2 cf3 H N 2-PhO-Ph 7-81 2 cf3 H N 2,6-FrPh 7-82 2 cf3 H N 2,6-CU-Ph 7-83 2 cf3 H N 2,6-Me9-Ph 7-84 2 cf3 H N 2,6-(OMe)?-Ph 7-85 2 cf3 H N 2,6-(CF3)2:Ph 7-86 2 cf3 H N 2,6-(OCF3)7-Ph 7-87 2 cf3 H N 2,3,4-Cl3-Ph 7-88 2 cf3 H N 2,4,6-Cl3-Ph 7-89 2 cf3 H N 2,6-Cl?-4-CF3-Ph 7-90 2 cf3 H N 2,6-C1^4-OCF3-Ph 7-91 2 cf3 H N 2,3?4-Me3-Ph 7-92 2 cf3 H N 2-Pyn 7-93 2 cf3 H N 3-Pyn 7-94 2 cf3 H N 4-Pyn 7-95 2 cf3 H N 6-Cl-2-Pyn 7-96 2 cf3 H N 6-CF3-2-Pyn 7-97 2 cf3 H N 6-Cl-4-CF3-2-Pyn 7-98 2 cf3 H N 2-Pym 7-99 2 cf3 H N 4-Pym 7-100 2 cf3 H N 4,6-Me2-2-Pym 7-101 2 cf3 H N 4,6«(OMe)2-2-Pym 7-102 2 CF, H N 3-Pyd - 200404764 第7表（續)-68- 200404764 Table 7 (continued) No. Substituted position R1 X J4 R13 Physical properties 7-63 2 cf3 HN 3-Cl-Ph 7-64 2 cf3 HN 4-Cl-Ph 7-65 2 cf3 HN 2-Me -Ph 7-66 2 cf3 HN 2-i-Pr-Ph 7-67 2 cf3 HN 2-OMe-Ph 7-68 2 cf3 HN 2-SMe-Ph 7-69 2 cf3 HN 2-SOMe-Ph 7- 70 2 cf3 HN 2-SO? Me-Ph 7-71 2 cf3 HN 2-CN-Ph 7-72 2 cf3 HN 2-NO, -Ph 7-73 2 CF3 HN 2-CF3-Ph. 7-74 2 cf3 HN 2-OCF3-Ph 7-75 2 cf3 HN 2-SCF3-Ph 7-76 2 cf3 HN 2-SOCF3-Ph 7-77 2 cf3 HN 2-S02CF3-Ph 7-78 2 cf3 HN 2-C02Me- Ph 7-79 2 cf3 HN 2-Ph-Ph 7-80 2 cf3 HN 2-PhO-Ph 7-81 2 cf3 HN 2,6-FrPh 7-82 2 cf3 HN 2,6-CU-Ph 7-83 2 cf3 HN 2,6-Me9-Ph 7-84 2 cf3 HN 2,6- (OMe)?-Ph 7-85 2 cf3 HN 2,6- (CF3) 2: Ph 7-86 2 cf3 HN 2, 6- (OCF3) 7-Ph 7-87 2 cf3 HN 2,3,4-Cl3-Ph 7-88 2 cf3 HN 2,4,6-Cl3-Ph 7-89 2 cf3 HN 2,6-Cl? -4-CF3-Ph 7-90 2 cf3 HN 2,6-C1 ^ 4-OCF3-Ph 7-91 2 cf3 HN 2,3? 4-Me3-Ph 7-92 2 cf3 HN 2-Pyn 7-93 2 cf3 HN 3-Pyn 7-94 2 cf3 HN 4-Pyn 7-95 2 cf3 HN 6-Cl-2-Pyn 7-96 2 cf3 HN 6-CF3 -2-Pyn 7-97 2 cf3 HN 6-Cl-4-CF3-2-Pyn 7-98 2 cf3 HN 2-Pym 7-99 2 cf3 HN 4-Pym 7-100 2 cf3 HN 4,6-Me2 -2-Pym 7-101 2 cf3 HN 4,6 «(OMe) 2-2-Pym 7-102 2 CF, HN 3-Pyd-200404764 Table 7 (continued)

No. 取代 位置 R1 X J4 R13 7-103 2 cf3 H N -CO-NHMe 7-104 2 cf3 H N -CO-NHPh 7-105 2 cf3 H N -CO-NMePh 7-106 2 cf3 H N -CO-NEt(c-Hex) 7-107 3 cf3 H N Me 7-108 3 cf3 H N t-Bu 7-109 3 cf3 H N -CH2-Ph 7]10 3 cf3 H N -CHMe-Ph 7-111 3 cf3 H N -CMe2-Ph 7-112 3 cf3 H N Ph 7-113 3 cf3 H N 2-F-Ph 7-114 3 cf3 H N 2-Cl-Ph 7-115 3 cf3 H N 3-Cl-Ph 7-116 3 cf3 H N 4-Cl-Ph 7-117 3 cf3 H N 2-Me-Ph 7-118 3 cf3 H N 2-i-Pr-Ph 7-119 3 cf3 H N 2-OMe-Ph 7-120 3 cf3 H N 2-SMe-Ph 7-121 3 cf3 H N 2-SOMe-Ph 7-122 3 cf3 H N 2-S02Me-Ph 7-123 3 cf3 H N 2-CN-Ph 7-124 3 cf3 H N 2-NO，-Ph 7-125 3 cf3 H N 2-CFrPh 7-126 3 cf3 H N 2-OCF3-Ph 7-127 3 cf3 H N 2-SCFrPh 7-128 3 cf3 H N 2-SOCF3-Ph 7-129 3 cf3 H N 2-S02CF3-Ph 7-130 3 cf3 H N 2-CO^Me-Ph 7-131 3 cf3 H N 2-Ph-Ph 7-132 3 cf3 H N 2-PhO-Ph 7-133 3 cf3 H N 4-PhO-Ph 7-134 3 cf3 H N 2,6-F2-Ph 7-135 3 cf3 H N 2,6-Cl2-Ph 7-136 3 cf3 H N 2,6-Me?-Ph 7-137 3 cf3 H N 2,6-(OMe)7-Ph 7-138 3 cf3 H N 2,6-(CF3)2-Ph 7-139 3 cf3 H N 2,6-(OCF3)2-Ph 7-140 3 cf3 H N 2,3,4-Cl3-Ph 7-141 3 cf3 H N 2,4,6-Cl3-Ph 7-142 3 cf3 H N 256-Cl?-4-CF3-Ph 7-143 3 CF, H N 2,6-CU-4-OCF,-Ph 物性 200404764 第7表（續）No. Substitution position R1 X J4 R13 7-103 2 cf3 HN -CO-NHMe 7-104 2 cf3 HN -CO-NHPh 7-105 2 cf3 HN -CO-NMePh 7-106 2 cf3 HN -CO-NEt (c -Hex) 7-107 3 cf3 HN Me 7-108 3 cf3 HN t-Bu 7-109 3 cf3 HN -CH2-Ph 7] 10 3 cf3 HN -CHMe-Ph 7-111 3 cf3 HN -CMe2-Ph 7 -112 3 cf3 HN Ph 7-113 3 cf3 HN 2-F-Ph 7-114 3 cf3 HN 2-Cl-Ph 7-115 3 cf3 HN 3-Cl-Ph 7-116 3 cf3 HN 4-Cl-Ph 7-117 3 cf3 HN 2-Me-Ph 7-118 3 cf3 HN 2-i-Pr-Ph 7-119 3 cf3 HN 2-OMe-Ph 7-120 3 cf3 HN 2-SMe-Ph 7-121 3 cf3 HN 2-SOMe-Ph 7-122 3 cf3 HN 2-S02Me-Ph 7-123 3 cf3 HN 2-CN-Ph 7-124 3 cf3 HN 2-NO, -Ph 7-125 3 cf3 HN 2-CFrPh 7-126 3 cf3 HN 2-OCF3-Ph 7-127 3 cf3 HN 2-SCFrPh 7-128 3 cf3 HN 2-SOCF3-Ph 7-129 3 cf3 HN 2-S02CF3-Ph 7-130 3 cf3 HN 2- CO ^ Me-Ph 7-131 3 cf3 HN 2-Ph-Ph 7-132 3 cf3 HN 2-PhO-Ph 7-133 3 cf3 HN 4-PhO-Ph 7-134 3 cf3 HN 2,6-F2- Ph 7-135 3 cf3 HN 2,6-Cl2-Ph 7-136 3 cf3 HN 2,6-Me? -Ph 7-137 3 cf3 HN 2,6- (OMe) 7-Ph 7-138 3 cf3 HN 2,6- (CF3) 2-Ph 7-139 3 cf3 HN 2,6- (OCF 3) 2-Ph 7-140 3 cf3 HN 2,3,4-Cl3-Ph 7-141 3 cf3 HN 2,4,6-Cl3-Ph 7-142 3 cf3 HN 256-Cl? -4-CF3- Ph 7-143 3 CF, HN 2,6-CU-4-OCF, -Ph Physical properties 200404764 Table 7 (continued)

No. Rl X J4 R13 物性 7-144 3 cf3 H N 2,3,4-Me3-Ph 7-145 3 cf3 H N 2-Pyn 7-146 3 cf3 H N 3-Pyn 7-147 3 cf3 H N 4-Pyn 7-148 3 cf3 H N 6-Cl<2-Pyn 7-149 3 cf3 H N 6-CF3-2-Pyn 7-150 3 cf3 H N 6-Cl-4-CF3-2-Pyn 7-151 3 cf3 H N 2-Pym 7-152 3 cf3 H N 4-Pym 7-153 3 cf3 H N 4,6-Me2-2-Pym 7-154 3 cf3 H N 4,6-(OMe)广 2-Pym 7-155 3 cf3 H N 3-Pyd " 7-156 3 cf3 H N -CO-NHMe 7-157 3 cf3 H N -CO-NHPh 7-158 3 cf3 H N -CO-NMePh 7-159 3 cf3 H N -CO-NEt(c-Hex) 7-160 4 cf3 H N Me 7-161 4 cf3 H N t-Bu 7-162 4 cf3 H N -CH2-Ph 7-163 4 cf3 H N -CHMe-Ph 7-164 4 cf3 H N -CMerPh 7-165 4 cf3 H N Ph 7-166 4 cf3 H N 2-F-Ph 7-167 4 cf3 H N 2-Cl-Ph 7-168 4 cf3 H N 3-Cl-Ph 7-169 4 cf3 H N 4-Cl-Ph 7-170 4 cf3 H N 2-Me-Ph 7-171 4 cf3 H N 2-i-Pr-Ph 7-172 4 cf3 H N 2-OMe-Ph 7-173 4 cf3 H N 2-SMe-Ph 7-174 4 cf3 H N 2-SOMe-Ph 7-175 4 cf3 H N 2-S02Me-Ph 7-176 4 cf3 H N 2-CN-Ph 7-177 4 cf3 H N 2-NO，-Ph 7-178 4 cf3 H N 2-CF3-Ph 7-179 4 cf3 H N 2-OCF3-Ph 7-180 4 cf3 H N 2-SCF3-Ph 7-181 4 cf3 H N 2-SOCF3-Ph 7-182 4 cf3 H N 2-S07CF3-Ph 7-183 4 cf3 H N 2-CO，Me-Ph 7-184 4 CF, H N 2-Ph-Ph 200404764 第7表（續）No. Rl X J4 R13 Physical properties 7-144 3 cf3 HN 2,3,4-Me3-Ph 7-145 3 cf3 HN 2-Pyn 7-146 3 cf3 HN 3-Pyn 7-147 3 cf3 HN 4-Pyn 7 -148 3 cf3 HN 6-Cl < 2-Pyn 7-149 3 cf3 HN 6-CF3-2-Pyn 7-150 3 cf3 HN 6-Cl-4-CF3-2-Pyn 7-151 3 cf3 HN 2- Pym 7-152 3 cf3 HN 4-Pym 7-153 3 cf3 HN 4,6-Me2-2-Pym 7-154 3 cf3 HN 4,6- (OMe) wide 2-Pym 7-155 3 cf3 HN 3- Pyd " 7-156 3 cf3 HN -CO-NHMe 7-157 3 cf3 HN -CO-NHPh 7-158 3 cf3 HN -CO-NMePh 7-159 3 cf3 HN -CO-NEt (c-Hex) 7- 160 4 cf3 HN Me 7-161 4 cf3 HN t-Bu 7-162 4 cf3 HN -CH2-Ph 7-163 4 cf3 HN -CHMe-Ph 7-164 4 cf3 HN -CMerPh 7-165 4 cf3 HN Ph 7 -166 4 cf3 HN 2-F-Ph 7-167 4 cf3 HN 2-Cl-Ph 7-168 4 cf3 HN 3-Cl-Ph 7-169 4 cf3 HN 4-Cl-Ph 7-170 4 cf3 HN 2 -Me-Ph 7-171 4 cf3 HN 2-i-Pr-Ph 7-172 4 cf3 HN 2-OMe-Ph 7-173 4 cf3 HN 2-SMe-Ph 7-174 4 cf3 HN 2-SOMe-Ph 7-175 4 cf3 HN 2-S02Me-Ph 7-176 4 cf3 HN 2-CN-Ph 7-177 4 cf3 HN 2-NO, -Ph 7-178 4 cf3 HN 2-CF3-Ph 7-179 4 cf3 HN 2-OCF3-Ph 7-180 4 cf3 HN 2-SCF3-Ph 7 -181 4 cf3 HN 2-SOCF3-Ph 7-182 4 cf3 HN 2-S07CF3-Ph 7-183 4 cf3 HN 2-CO, Me-Ph 7-184 4 CF, HN 2-Ph-Ph 200404764 Table 7 (Continued)

No. 取代 位置No. Replaced Position

X J4 R13 物性 〔融點rc)〕 7-185 7-186 7-187 7-188 7-189 7-190 7-191 7-192 7-193 7-194 7-195 7-196 7-197 7-198 7-199 7-200 7-201 7-202 7-203 7-204 7-205 7-206 7-207 7-208 7-209 7-210 7-211 7-212 7-213 7-214 7-215 7-216 7-217 7-218 7-219 7-220 7-221 7-222 7-223 7-224 7-225 4444444444444444444444 4 4444 22222222222222X J4 R13 Physical properties (melting point rc)] 7-185 7-186 7-187 7-188 7-189 7-190 7-191 7-192 7-193 7-194 7-195 7-196 7-197 7 -198 7-199 7-200 7-201 7-202 7-203 7-204 7-205 7-206 7-207 7-208 7-209 7-210 7-211 7-212 7-213 7-214 7-215 7-216 7-217 7-218 7-219 7-220 7-221 7-222 7-223 7-224 7-225 4444444444444444444444 4 4444 22222222222222

2 2 2 2 2 2 2 2 2 2 2 2 2 2 33333333333333333333333333 3 ΠΓ Γτ』Γτ」Γτ」Γτ ‘ Γτ , Γτ」fTI- Ητ」fT1·Fl· fffffffffffffffffffffffffffh[irihihih[irih[ih[ih[ih[ihih[ihihicccccccccccccccccccccccccccCHCHCHCHgCHCHCKCHCHCHCHCFCF KJX J1 J1 i i T1 J1 i Ji iiTliJlJATlTlrlJXTlTliTlTlTl Jx TUJXJ1JXJXJ1JXJ1JXJX J1 JA J1 F Tr* ΤΓ- ΤΓ- THX ΤΓ- Tr* ΤΓ- f ΤΓ* t ΤΓ- TP ΤΓ* ΤΓ- t t Tr* Tr- XKX ΤΓ- ΤΓ- TF ΤΓ- ΤΓ* t F PM Tr* ΤΓ- t F Lx t Lx ΤΓ ΤΓ- TUI ΤΓ ΤΓ N 2-PhO-Ph N 2?6-F9-Ph N 2,6-Cl?-Ph N 2,6-Me?-Ph N 2,6-(OMe)2-Ph N 2,6-(CF3)，-Ph N 2,6-(OCF3)，-Ph N 2,3,4-Cl3-Ph N 2,4,6-Cl3-Ph N 2,6-Cl，-4-CFrPh N 2,6-Cl,-4-OCF3-Ph N 2,3,4-Me3-Ph N 2-Pyn N 3-Pyn N 4-Pyn N 6-Cl-2-Pyn N 6-CF3-2-Pyn N 6-Cl-4-CF3-2-Pyn N 2-Pym N 4-Pym N 4,6-Me2-2-Pym N 4,6-(OMe)?-2-Pym N 3-Pyd ^ N -CO-NHMe N -CO-NHPh N -CO-NMePh N -CO-NEt(c-Hex) N Me N t-Bu N -CH?-Ph N -CHMe-Ph N -CMe?-Ph N Ph N 2-F-Ph N 2-Cl-Ph N 3-Cl-Ph N 4-Cl-Ph N 2-Me-Ph N 2-i-Pr-Ph N 2-OMe-Ph N 2-SMe-Ph2 2 2 2 2 2 2 2 2 2 2 2 2 2 33 333 333 333 333 333 333 333 333 [ihihicccccccccccccccccccccccccccCHCHCHCHgCHCHCKCHCHCHCHCFCF KJX J1 J1 ii T1 J1 i Ji iiTliJlJATlTlrlJXTlTliTlTlTl Jx TUJXJ1JXJXJ1JXJ1JXJX J1 JA J1 F Tr * ΤΓ- ΤΓ- THX ΤΓ- Tr * ΤΓ- f ΤΓ * t ΤΓ- TP ΤΓ * ΤΓ- tt Tr * Tr- XKX ΤΓ- ΤΓ -TF ΤΓ- ΤΓ * t F PM Tr * ΤΓ- t F Lx t Lx ΤΓ ΤΓ- TUI ΤΓ ΤΓ N 2-PhO-Ph N 2? 6-F9-Ph N 2,6-Cl? -Ph N 2, 6-Me? -Ph N 2,6- (OMe) 2-Ph N 2,6- (CF3), -Ph N 2,6- (OCF3), -Ph N 2,3,4-Cl3-Ph N 2,4,6-Cl3-Ph N 2,6-Cl, -4-CFrPh N 2,6-Cl, -4-OCF3-Ph N 2,3,4-Me3-Ph N 2-Pyn N 3- Pyn N 4-Pyn N 6-Cl-2-Pyn N 6-CF3-2-Pyn N 6-Cl-4-CF3-2-Pyn N 2-Pym N 4-Pym N 4,6-Me2-2- Pym N 4,6- (OMe)?-2-Pym N 3-Pyd ^ N -CO-NHMe N -CO-NHPh N -CO-NMePh N -CO-NEt (c-Hex) N Me N t-Bu N -CH? -Ph N -CHMe-Ph N -CMe? -Ph N Ph N 2-F-Ph N 2-Cl-Ph N 3-Cl-Ph N 4-Cl-Ph N 2-Me-Ph N 2-i-Pr-Ph N 2-OMe-Ph N 2-SMe-Ph

114.9 -72- 200404764 第7表（續)114.9 -72- 200404764 Table 7 (continued)

No. 取代 位置 R1 X J4 R13 物性 7-226 2 chf2 H N 2-SOMe-Ph 7-227 2 chf2 H N 2-S02Me-Ph 7-228 2 CHF? H N 2-CN-Ph 7-229 2 chf2 H N 2-NCVPh 7-230 2 chf2 H N . 2-CF3-Ph 7-231 2 chf9 H N 2-OCF3-Ph 7-232 2 CHF? H N 2-SCF3-Ph 7-233 2 chf2 H N 2-SOCF3-Ph 7-234 2 chf7 H N 2-S07CF3-Ph 7-235 2 chf2 H N 2-CO，Me-Ph 7-236 2 chf7 H N 2-Ph-Ph 7-237 2 chf2 H N 2-PhO-Ph 7-238 2 chf2 H N 2,6-F，-Ph 7-239 2 chf9 H N 2,6-Cl2-Ph 7-240 2 CHF, H N 2,6-Me?-Ph 7-241 2 CHF? H N 2,6-(OMe)?-Ph 7-242 2 CHF? H N 2,6-(CF3)2-Ph 7-243 2 CHF, H N 2,6-(OCF3)，-Ph 7-244 2 CHF? H N 2,3,4-Cl3-Pii 7-245 2 CHF; H N 2,4,6-Cl3-Ph 7-246 2 CHF? H N 2,6-Cl7-4-CF3-Ph 7-247 2 CHF; H N 2,6-Cl;-4-OCF3-Ph 7-248 2 chf2 H N 2,3,4-MerPh 7-249 2 chf2 H N 2-Pyn 7-250 2 chf2 H N 3-Pyn 7-251 2 chf2 H N 4-Pyn 7-252 2 chf2 H N 6-Cl-2-Pyn 7-253 2 CHF， H N 6-CF3-2-Pyn 7-254 2 chf2 H N 6-Cl-4-CF3-2-Pyn 7-255 2 chf2 H N 2-Pym 7-256 2 chf2 H N 4-Pym 7-257 2 chf2 H N 4,6-Me2-2-Pym 7-258 2 chf2 H N 4,6-(OMe)9-2-Pym 7-259 2 CHF， H N 3-Pyd ^ 7-260 2 chf2 H N -CO-NHMe 7-261 2 CHF, H N -CO-NHPh 7-262 2 CHF, H N -CO-NMePh 7-263 2 CHF, H N -CO-NEt(c-Hex)No. Substitution position R1 X J4 R13 Physical properties 7-226 2 chf2 HN 2-SOMe-Ph 7-227 2 chf2 HN 2-S02Me-Ph 7-228 2 CHF? HN 2-CN-Ph 7-229 2 chf2 HN 2 -NCVPh 7-230 2 chf2 HN. 2-CF3-Ph 7-231 2 chf9 HN 2-OCF3-Ph 7-232 2 CHF? HN 2-SCF3-Ph 7-233 2 chf2 HN 2-SOCF3-Ph 7- 234 2 chf7 HN 2-S07CF3-Ph 7-235 2 chf2 HN 2-CO, Me-Ph 7-236 2 chf7 HN 2-Ph-Ph 7-237 2 chf2 HN 2-PhO-Ph 7-238 2 chf2 HN 2,6-F, -Ph 7-239 2 chf9 HN 2,6-Cl2-Ph 7-240 2 CHF, HN 2,6-Me? -Ph 7-241 2 CHF? HN 2,6- (OMe) ? -Ph 7-242 2 CHF? HN 2,6- (CF3) 2-Ph 7-243 2 CHF, HN 2,6- (OCF3), -Ph 7-244 2 CHF? HN 2,3,4- Cl3-Pii 7-245 2 CHF; HN 2,4,6-Cl3-Ph 7-246 2 CHF? HN 2,6-Cl7-4-CF3-Ph 7-247 2 CHF; HN 2,6-Cl; -4-OCF3-Ph 7-248 2 chf2 HN 2,3,4-MerPh 7-249 2 chf2 HN 2-Pyn 7-250 2 chf2 HN 3-Pyn 7-251 2 chf2 HN 4-Pyn 7-252 2 chf2 HN 6-Cl-2-Pyn 7-253 2 CHF, HN 6-CF3-2-Pyn 7-254 2 chf2 HN 6-Cl-4-CF3-2-Pyn 7-255 2 chf2 HN 2-Pym 7 -256 2 chf2 HN 4-Pym 7-257 2 chf2 HN 4,6-Me2-2- Pym 7-258 2 chf2 HN 4,6- (OMe) 9-2-Pym 7-259 2 CHF, HN 3-Pyd ^ 7-260 2 chf2 HN -CO-NHMe 7-261 2 CHF, HN -CO- NHPh 7-262 2 CHF, HN -CO-NMePh 7-263 2 CHF, HN -CO-NEt (c-Hex)

-73- 200404764 通式（I — 7)-73- 200404764 general formula (I — 7)

(I - 7) 第8表（R1=cf3 、R2=H、 m=〇、Α=- ch2 -^ Gl=G2=0) No. 取代 位置 X J4 R13 R9 物性 8-1 2 Η CH Η Me 8-2 2 Η CH Η t-Bu 8-3 2 Η CH Η -CH,-Ph 8-4 2 Η CH Η -CHMe-Ph 8-5 2 Η CH Η -CMe?-Ph 8-6 2 Η CH Η Ph 8-7 2 Η CH Η 2-F-Ph 8-8 2 Η CH Η 2-Cl-Ph 8-9 2 Η CH Η 3-Cl-Ph 8-10 2 Η CH Η 4-Cl-Ph 8-11 2 Η CH Η 2-Me-Ph 8-12 2 Η CH Η 2-i-Pr-Ph 8-13 2 Η CH Η 2-OMe-Ph 8-14 2 Η CH Η 2-SMe-Ph 8-15 2 Η CH Η 2-SOMe-Ph 8-16 2 Η CH Η 2-SO,Me-Ph 8-17 2 Η CH Η 2-CN-Ph 8-18 2 Η CH Η 2-NCVPh 8-19 2 Η CH Η 2-CF3-Ph 8-20 2 Η CH Η 2-OCF3-Ph 8-21 2 Η CH Η 2-SCF3-Ph 8-22 2 Η CH Η 2-SOCF3-Ph 8-23 2 Η CH Η 2-SO,CF3-Ph 8-24 2 Η CH Η 2-CO?Me-Ph 8-25 2 Η CH Η 2-Ph-Ph 8-26 2 Η CH Η 2-PhO-Ph 8-27 2 Η CH Η 2,6-F2-Ph 8-28 2 Η CH Η 2,6-Cl2-Ph 8-29 2 Η CH Η 2,6-Me?-Ph 8-30 2 Η CH Η 2,4,6-Cl,-Ph -7 4- 200404764 第8表（續) No. 取代 位置 X J4 R13 R9 物性 〔融點（°C)〕 8-31 2 Η CH Η 2,6-Cl9-4-CF3-Ph 8-32 2 Η CH Η 2,6-Cl2-4-OCF3-Ph 8-33 2 Η CH Η 2,3,4-Me3-Ph 8-34 2 Η CH Η 2-Pyn 8-35 2 Η CH Η 3-Pyn 8-36 2 Η CH Η 4-Pyn 8-37 2 Η CH Η 6-Cl-2-Pyn 8-38 2 Η CH Η 6-CF3-2-Pyn 8-39 2 Η CH Η 6-Cl-4-CF3-2-Pyn 8-40 2 Η CH Η 2-Pym 8-41 2 Η CH Η 4-Pym 8-42 2 Η CH Η 4,6-Me?-2-Pym 8-43 2 Η CH Η 4,6-(OMe)9-2-Pym 8-44 2 Η CH Η 3-Pyd 8-45 2 Η CH Η -CO-NHMe 8-46 2 Η CH Η -CO-NHPh 8-47 2 Η CH Η -CO-NMePh 8-48 2 Η CH MHe -CO-NEt(c-Hex) 8-49 2 Η CH Me 8-50 2 Η CH Me t-Bu 8-51 2 Η CH Me -CH2-Ph 8-52 2 Η CH Me -CHMe-Ph 8-53 2 Η CH Me -CMe2-Ph 8-54 2 Η CH Me Ph 8-55 2 Η CH Me 2-F-Ph 8-56 2 Η CH Me 2-Cl-Ph 105-106 8-57 2 Η CH Me 3-Cl-Ph 8-58 2 Η CH Me 4-Cl-Ph 8-59 2 Η CH Me 2-Me-Ph 8-60 2 Η CH Me 2-i-Pr-Ph 8-61 2 Η CH Me 2-OMe-Ph 8-62 2 Η CH Me 2-SMe-Ph 8-63 2 Η CH Me 2-SOMe-Ph 8-64 2 Η CH Me 2-SO,Me-Ph 8-65 2 Η CH Me 2-CN-Ph 8-66 2 Η CH Me 2-NO，-Ph 8-67 2 Η CH Me 2-CF3-Ph 8-68 2 Η CH Me 2-OCF3-Ph 8-69 2 Η CH Me 2-SCF3-Ph 8-70 2 Η CH Me 2-SOCF3-Ph 8-71 2 Η CH Me 2-SO,CFrPh 200404764 第8表（續）(I-7) Table 8 (R1 = cf3, R2 = H, m = 〇, A =-ch2-^ Gl = G2 = 0) No. Substitution position X J4 R13 R9 Physical properties 8-1 2 Η CH Η Me 8-2 2 Η CH Η t-Bu 8-3 2 Η CH Η -CH, -Ph 8-4 2 Η CH Η -CHMe-Ph 8-5 2 Η CH Η -CMe? -Ph 8-6 2 Η CH Η Ph 8-7 2 Η CH Η 2-F-Ph 8-8 2 Η CH Η 2-Cl-Ph 8-9 2 Η CH Η 3-Cl-Ph 8-10 2 Η CH Η 4-Cl- Ph 8-11 2 Η CH Η 2-Me-Ph 8-12 2 Η CH Η 2-i-Pr-Ph 8-13 2 Η CH Η 2-OMe-Ph 8-14 2 Η CH Η 2-SMe- Ph 8-15 2 Η CH Η 2-SOMe-Ph 8-16 2 Η CH Η 2-SO, Me-Ph 8-17 2 Η CH Η 2-CN-Ph 8-18 2 Η CH Η 2-NCVPh 8 -19 2 Η CH Η 2-CF3-Ph 8-20 2 Η CH Η 2-OCF3-Ph 8-21 2 Η CH Η 2-SCF3-Ph 8-22 2 Η CH Η 2-SOCF3-Ph 8-23 2 Η CH Η 2-SO, CF3-Ph 8-24 2 Η CH Η 2-CO? Me-Ph 8-25 2 Η CH Η 2-Ph-Ph 8-26 2 Η CH Η 2-PhO-Ph 8 -27 2 Η CH Η 2,6-F2-Ph 8-28 2 Η CH Η 2,6-Cl2-Ph 8-29 2 Η CH Η 2,6-Me? -Ph 8-30 2 Η CH Η 2 , 4,6-Cl, -Ph -7 4- 200404764 Table 8 (continued) No. Substituted position X J4 R13 R9 Physical properties [melting point (° C)] 8-31 2 Η CH Η 2,6-Cl9-4-CF3-Ph 8-32 2 Η CH Η 2,6-Cl2-4-OCF3-Ph 8-33 2 Η CH Η 2,3,4-Me3-Ph 8-34 2 Η CH Η 2-Pyn 8-35 2 Η CH Η 3-Pyn 8-36 2 Η CH Η 4-Pyn 8-37 2 Η CH Η 6-Cl-2-Pyn 8-38 2 Η CH Η 6- CF3-2-Pyn 8-39 2 Η CH Η 6-Cl-4-CF3-2-Pyn 8-40 2 Η CH Η 2-Pym 8-41 2 Η CH Η 4-Pym 8-42 2 Η CH Η 4,6-Me? -2-Pym 8-43 2 ΗCH Η 4,6- (OMe) 9-2-Pym 8-44 2 ΗCH Η 3-Pyd 8-45 2 ΗCH Η -CO-NHMe 8-46 2 Η CH Η -CO-NHPh 8-47 2 Η CH Η -CO-NMePh 8-48 2 Η CH MHe -CO-NEt (c-Hex) 8-49 2 Η CH Me 8-50 2 Η CH Me t-Bu 8-51 2 Η CH Me -CH2-Ph 8-52 2 Η CH Me -CHMe-Ph 8-53 2 Η CH Me -CMe2-Ph 8-54 2 Η CH Me Ph 8-55 2 Η CH Me 2-F-Ph 8-56 2 Η CH Me 2-Cl-Ph 105-106 8-57 2 Η CH Me 3-Cl-Ph 8-58 2 Η CH Me 4-Cl-Ph 8-59 2 Η CH Me 2-Me-Ph 8-60 2 Η CH Me 2-i-Pr-Ph 8-61 2 Η CH Me 2-OMe-Ph 8-62 2 Η CH Me 2-SMe-Ph 8-63 2 Η CH Me 2-SOMe-Ph 8-64 2 Η CH Me 2-SO, Me-Ph 8-65 2 Η CH Me 2-CN-Ph 8-66 2 Η CH Me 2-NO, -Ph 8- 67 2 Η CH M e 2-CF3-Ph 8-68 2 Η CH Me 2-OCF3-Ph 8-69 2 Η CH Me 2-SCF3-Ph 8-70 2 Η CH Me 2-SOCF3-Ph 8-71 2 Η CH Me 2 -SO, CFrPh 200404764 Table 8 (continued)

No. X J4 R13 R9 物性 8-72 2 Η CH Me 2-C02Me-Ph 8-73 2 Η CH Me 2-Ph-Ph 8-74 2 Η CH Me 2-PhO-Ph 8-75 2 Η CH Me 2?6-F7-Ph 8-76 2 Η CH Me 2?6-Cl?-Ph 8-77 2 Η CH Me 2,6-Me2-Ph 8-78 2 Η CH Me 2,4,6-Cl3-Ph 8-79 2 Η CH Me 2,6-Cl2-4-CF3-Ph 8-80 2 Η CH Me 2,6-Cl9-4-OCF3-Ph 8-81 2 Η CH Me 2?3,4-Me3-Ph 8-82 2 Η CH Me 2-Pyn 8-83 2 Η CH Me 3-Pyn 8-84 2 Η CH Me 4-Pyn 8-85 2 Η CH Me 6-Cl-2-Pyn 8-86 2 Η CH Me 6-CF3-2-Pyn 8-87 2 Η CH Me 6-Cl-4-CF3-2-Pyn 8-88 2 Η CH Me 2-Pym 8-89 2 Η CH Me 4-Pym 8-90 2 Η CH Me 4,6-Me2-2-Pym 8-91 2 Η CH Me 4?6-(OMe)2-2-Pym 8-92 2 Η CH Me 3-Pyd 8-93 2 Η CH Me -CO-NHMe 8-94 2 Η CH Me -CO-NHPh 8-95 2 Η CH Me -CO-NMePh 8-96 2 Η CH Me -CO-NEt(c-Hex) 8-97 2 Η Ν Me Me 8-98 2 Η Ν Me t-Bu 8-99 2 Η Ν Me -CH?-Ph 8-100 2 Η Ν Me -CHMe-Ph 8-101 2 Η Ν Me -CMe7-Ph 8-102 2 Η Ν Me Ph 8-103 2 Η Ν Me 2-F-Ph 8-104 2 Η Ν Me 2-Cl-Ph 8-105 2 Η Ν Me 3-Cl-Ph 8-106 2 Η Ν Me 4-Cl-Ph 8-107 2 Η Ν Me 2-Me-Ph 8-108 2 Η Ν Me 2-i-Pr-Ph 8-109 2 Η Ν Me 2-OMe-Ph 8-110 2 Η Ν Me 2-SMe-Ph 8-111 2 Η Ν Me 2-SOMe-Ph 8-112 2 Η Ν Me 2-SO，Me-PhNo. X J4 R13 R9 Physical properties 8-72 2 Η CH Me 2-C02Me-Ph 8-73 2 Η CH Me 2-Ph-Ph 8-74 2 Η CH Me 2-PhO-Ph 8-75 2 Η CH Me 2? 6-F7-Ph 8-76 2 Η CH Me 2? 6-Cl? -Ph 8-77 2 Η CH Me 2,6-Me2-Ph 8-78 2 Η CH Me 2,4,6-Cl3 -Ph 8-79 2 Η CH Me 2,6-Cl2-4-CF3-Ph 8-80 2 ΗCH Me 2,6-Cl9-4-OCF3-Ph 8-81 2 ΗCH Me 2? 3,4 -Me3-Ph 8-82 2 Η CH Me 2-Pyn 8-83 2 Η CH Me 3-Pyn 8-84 2 Η CH Me 4-Pyn 8-85 2 Η CH Me 6-Cl-2-Pyn 8- 86 2 Η CH Me 6-CF3-2-Pyn 8-87 2 Η CH Me 6-Cl-4-CF3-2-Pyn 8-88 2 Η CH Me 2-Pym 8-89 2 Η CH Me 4-Pym 8-90 2 Η CH Me 4,6-Me2-2-Pym 8-91 2 Η CH Me 4? 6- (OMe) 2-2-Pym 8-92 2 Η CH Me 3-Pyd 8-93 2 Η CH Me -CO-NHMe 8-94 2 Η CH Me -CO-NHPh 8-95 2 Η CH Me -CO-NMePh 8-96 2 Η CH Me -CO-NEt (c-Hex) 8-97 2 Η Ν Me Me 8-98 2 Η Ν Me t-Bu 8-99 2 Η Ν Me -CH? -Ph 8-100 2 Η Ν Me -CHMe-Ph 8-101 2 Η Ν Me -CMe7-Ph 8-102 2 Η Ν Me Ph 8-103 2 Η Ν Me 2-F-Ph 8-104 2 Η Ν Me 2-Cl-Ph 8-105 2 Η Ν Me 3-Cl-Ph 8-106 2 Η Ν Me 4-Cl -Ph 8-107 2 Η Ν Me 2-Me-Ph 8-108 2 Η Ν Me 2-i-Pr-Ph 8-109 2 Η Ν Me 2-OMe-Ph 8-110 2 Η Ν Me 2-SMe-Ph 8-111 2 Η Ν Me 2-SOMe-Ph 8-112 2 Η Ν Me 2-SO, Me-Ph

-76- 200404764 第8表（續)-76- 200404764 Form 8 (Continued)

No. 取代 位置 X J4 R13 R9 8-113 2 Η Ν Me 2-CN-Ph 8-114 2 Η Ν Me 2-NOrPh 8-115 2 Η Ν Me 2-CFrPh 8-116 2 Η Ν Me 2-OCF3-Ph 8-117 2 Η Ν Me 2-SCF3-Ph 8-118 2 Η Ν Me 2-SOCF3-Ph 8-119 2 Η Ν Me 2-S02CF3-Ph 8-120 2 Η Ν Me 2-C02Me-Ph 8-121 2 Η Ν Me 2-Ph-Ph 8-122 2 Η Ν Me 2-PhO-Ph 8-123 2 Η Ν Me 2,6-F?-Ph 8-124 2 Η Ν Me 2,6-Cl，-Ph 8-125 2 Η Ν Me 2,6-Me2-Ph 8-126 2 Η Ν Me 2,4,6-Cl3-Ph 8-127 2 Η Ν Me 2,6-Cl2-4-CF3-Ph 8-128 2 Η Ν Me 2,6-Cl,-4-OCF3-Ph 8-129 2 Η Ν Me 2,3?4-Me3-Ph 8-130 2 Η Ν Me 2-Pyn 8-131 2 Η Ν Me 3-Pyn 8-132 2 Η Ν Me 4-Pyn 8-133 2 Η Ν Me 6-Cl-2-Pyn 8-134 2 Η Ν Me 6-CF3-2-Pyn 8-135 2 Η Ν Me 6-Cl-4-CF3-2-Pyn 8-136 2 Η Ν Me 2-Pym 8-137 2 Η Ν Me 4-Pym 8-138 2 Η Ν Me 4,6-Me2-2-Pym 8-139 2 Η Ν Me 4,6-(OMe)?-2-Pym 8-140 2 Η Ν Me 3-Pyd - 8-141 2 Η Ν Me -CO-NHMe 8-142 2 Η Ν Me -CO-NHPh 8-143 2 Η Ν Me -CO-NMePh 8-144 2 Η Ν Me -CO-NEt(c-Hex) 8-145 4 Η CH H Me 8-146 4 Η CH H t-Bu 8-147 4 Η CH H -CH,-Ph 8-148 4 Η CH H -CHMe-Ph 8-149 4 Η CH H - CMe，-Ph 8-150 4 Η CH H Ph 8-151 4 Η CH H 2-Cl-Ph 8-152 4 Η CH H 2-Me-Ph 8-153 4 Η CH H 3-Me-Ph 物性No. Substitution position X J4 R13 R9 8-113 2 Η Ν Me 2-CN-Ph 8-114 2 Η Ν Me 2-NOrPh 8-115 2 Η Ν Me 2-CFrPh 8-116 2 Η Ν Me 2-OCF3 -Ph 8-117 2 Η Ν Me 2-SCF3-Ph 8-118 2 Η Ν Me 2-SOCF3-Ph 8-119 2 Η Ν Me 2-S02CF3-Ph 8-120 2 Η Ν Me 2-C02Me-Ph 8-121 2 Η Ν Me 2-Ph-Ph 8-122 2 Η Ν Me 2-PhO-Ph 8-123 2 Η Ν Me 2,6-F? -Ph 8-124 2 Η Ν Me 2,6- Cl, -Ph 8-125 2 Η Ν Me 2,6-Me2-Ph 8-126 2 Η Ν Me 2,4,6-Cl3-Ph 8-127 2 Η Ν Me 2,6-Cl2-4-CF3 -Ph 8-128 2 Η Ν Me 2,6-Cl, -4-OCF3-Ph 8-129 2 Η Ν Me 2,3? 4-Me3-Ph 8-130 2 Η Ν Me 2-Pyn 8-131 2 Η Ν Me 3-Pyn 8-132 2 Η Ν Me 4-Pyn 8-133 2 Η Ν Me 6-Cl-2-Pyn 8-134 2 Η Ν Me 6-CF3-2-Pyn 8-135 2 Η Ν Me 6-Cl-4-CF3-2-Pyn 8-136 2 Η Ν Me 2-Pym 8-137 2 Η Ν Me 4-Pym 8-138 2 Η Ν Me 4,6-Me2-2-Pym 8 -139 2 Η Ν Me 4,6- (OMe)?-2-Pym 8-140 2 Η Ν Me 3-Pyd-8-141 2 Η Ν Me -CO-NHMe 8-142 2 Η Ν Me -CO- NHPh 8-143 2 Η Ν Me -CO-NMePh 8-144 2 Η Ν Me -CO-NEt (c-Hex) 8-145 4 Η CH H Me 8-146 4 Η CH H t-Bu 8-147 4CH H -CH, -Ph 8-148 4 Η CH H -CHMe-Ph 8-149 4 Η CH H-CMe, -Ph 8-150 4 Η CH H Ph 8-151 4 Η CH H 2-Cl-Ph 8-152 4 Η CH H 2-Me-Ph 8-153 4 Η CH H 3-Me-Ph Physical properties

-77- 200404764-77- 200404764

第8表（續)Table 8 (continued)

No. 取代 位置 X J4 R13 R9 物性 8-154 4 Η CH Η 4-Me-Ph 8-155 4 Η CH Η 2-OMe-Ph 8-156 4 Η CH Η 2-CN-Ph 8-157 4 Η CH Η 2-NCVPh 8-158 4 Η CH Η 2-CF3-Ph 8-159 4 Η CH Η 2-OCF3-Ph 8-160 4 Η CH Η 2-C02Me-Ph 8-161 4 Η CH Η 2-Ph-Ph 8-162 4 Η CH Η 2-PhO-Ph 8-163 4 Η CH Η 2,6-Cl2-Ph 8-164 4 Η CH Η 2,6-Me?-Ph 8-165 4 Η CH Η 2,4,6-drPh 8-166 4 Η CH Η 2,3,4-MerPh 8-167 4 Η CH Η 2-Pyn 8-168 4 Η CH Η 3-Pyn 8-169 4 Η CH Η 4-Pyn 8-170 4 Η CH Η 2-Pym 8-171 4 Η CH Η 4-Pym 8-172 4 Η CH Η 4,6-Me2-2-Pym 8-173 4 Η CH Η 4,6-(OMe)?-2-Pym 8-174 4 Η CH Η 3-Pyd " -78- 200404764 通式（I — 8)No. Substitution position X J4 R13 R9 Physical properties 8-154 4 Η CH Η 4-Me-Ph 8-155 4 Η CH Η 2-OMe-Ph 8-156 4 Η CH Η 2-CN-Ph 8-157 4 Η CH Η 2-NCVPh 8-158 4 Η CH Η 2-CF3-Ph 8-159 4 Η CH Η 2-OCF3-Ph 8-160 4 Η CH Η 2-C02Me-Ph 8-161 4 Η CH Η 2- Ph-Ph 8-162 4 Η CH Η 2-PhO-Ph 8-163 4 Η CH Η 2,6-Cl2-Ph 8-164 4 Η CH Η 2,6-Me? -Ph 8-165 4 Η CH Η 2,4,6-drPh 8-166 4 Η CH Η 2,3,4-MerPh 8-167 4 Η CH Η 2-Pyn 8-168 4 Η CH Η 3-Pyn 8-169 4 Η CH Η 4 -Pyn 8-170 4 ΗCH Η 2-Pym 8-171 4 ΗCH Η 4-Pym 8-172 4 ΗCH Η 4,6-Me2-2-Pym 8-173 4 ΗCH Η 4,6- ( OMe)?-2-Pym 8-174 4 Η CH Η 3-Pyd " -78- 200404764 General formula (I — 8)

R1-S02(R2)NR1-S02 (R2) N

Ά一 N N—R 2^\j4 人 G1人. 9 (1-8)Ά 一 N N—R 2 ^ \ j4 people G1 people. 9 (1-8)

R 13 第9表（R1=cf3 ' R2=H、 m=0、Α=- ch2 -、Gi=G2==0 ) No. 取代 位置 X J4 R13 R9 物性 9-1 2 Η CH Η Me 9-2 2 Η CH Η t-Bu 9-3 2 Η CH Η -CH2-Ph 9-4 2 Η CH Η -CHMe-Ph 9-5 2 Η CH Η -CMe?-Ph 9-6 2 Η CH Η Ph 9-7 2 Η CH Η 2-F-Ph 9-8 2 Η CH Η 2-Cl-Ph 9-9 2 Η CH Η 3-Cl-Ph 9-10 2 Η CH Η 4-Cl-Ph 9-11 2 Η CH Η 2-Me-Ph 9-12 2 Η CH Η 2-i-Pr-Ph 9-13 2 Η CH Η 2-OMe-Ph 9-14 2 Η CH Η 2-SMe-Ph 9-15 2 Η CH Η 2-SOMe-Ph 9-16 2 Η CH Η 2-SO.Me-Ph 9-17 2 Η CH Η 2-CN-Ph 9-18 2 Η CH Η 2-NO,-Ph 9-19 2 Η CH Η 2-CF3-Ph 9-20 2 Η CH Η 2-OCF3-Ph 9-21 2 Η CH Η 2-SCF3-Ph 9-22 2 Η CH Η 2-SOCF3-Ph 9-23 2 Η CH Η 2-S02CF3-Ph 9-24 2 Η CH Η 2-C02Me-Ph 9-25 2 Η CH Η 2-Ph-Ph 9-26 2 Η CH Η 2-PhO-Ph 9-27 2 Η CH Η 2,6-FrPh 9-28 2 Η CH Η 2,6-Cl，-Ph 9-29 2 Η CH Η 2,6-Me,-Ph •79- 200404764 第9表（續) No. 取代 位置 X J4 R13 R9 物性 〔融點（°C)〕 9-30 2 Η CH Η 2,4,6-Cl3-Ph 9-31 2 Η CH Η 2,6-Cl?-4-CF3-Ph 9-32 2 Η CH Η 2,6-Cl,-4-OCF3-Ph 9-33 2 Η CH Η 2?3,4-Me3-Ph 9-34 2 Η CH Η 2-Pyn 9-35 2 Η CH Η 3-Pyn 9-36 2 Η CH Η 4-Pyn 9-37 2 Η CH Η 6-Cl-2-Pyn 9-38 2 Η CH Η 6-CF3-2-Pyn 9-39 2 Η CH Η 6-Cl-4-CF3-2-Pyn 9-40 2 Η CH Η 2-Pym 9-41 2 Η CH Η 4-Pym 9-42 2 Η CH Η 4,6-Me2-2-Pym 9-43 2 Η CH Η 4,6-(OMe)2-2-Pym 9-44 2 Η CH Η 3-Pyd 9-45 2 Η CH Η -CO-NHMe 9-46 2 Η CH Η -CO-NHPh 9-47 2 Η CH Η -CO-NMePh 9-48 2 Η CH Η -CO-NEt(c-Hex) 9-49 2 Η CH Me Me 9-50 2 Η CH Me t-Bu 9-51 2 Η CH Me -CH?-Ph 9-52 2 Η CH Me Me -CHMe-Ph 9-53 2 Η CH -CMe?-Ph 9-54 2 Η CH Me Ph 9-55 2 Η CH Me Me 2-F-Ph 9-56 2 Η CH 2-Cl-Ph 166-167 9-57 2 Η CH Me 3-Cl-Ph 9-58 2 Η CH Me 4-Cl-Ph 9-59 2 Η CH Me 2-Me-Ph 9-60 2 Η CH Me 2-i-Pr-Ph 9-61 2 Η CH Me 2-OMe-Ph 9-62 2 Η CH Me 2-SMe-Ph 9-63 2 Η CH Me 2-SOMe-Ph 9-64 2 Η CH Me 2-SO,Me-Ph 9-65 2 Η CH Me 2-CN-Ph 9-66 2 Η CH Me 2-NO，-Ph 9-67 2 Η CH Me 2-CF3-Ph 9-68 2 Η CH Me 2-OCF,-Ph -80- 200404764 第9表（續)R 13 Table 9 (R1 = cf3 'R2 = H, m = 0, A =-ch2-, Gi = G2 == 0) No. Substitution position X J4 R13 R9 Physical properties 9-1 2 Η CH Η Me 9- 2 2 Η CH Η t-Bu 9-3 2 Η CH Η -CH2-Ph 9-4 2 Η CH Η -CHMe-Ph 9-5 2 Η CH Η -CMe? -Ph 9-6 2 Η CH Η Ph 9-7 2 Η CH Η 2-F-Ph 9-8 2 Η CH Η 2-Cl-Ph 9-9 2 Η CH Η 3-Cl-Ph 9-10 2 Η CH Η 4-Cl-Ph 9- 11 2 Η CH Η 2-Me-Ph 9-12 2 Η CH Η 2-i-Pr-Ph 9-13 2 Η CH Η 2-OMe-Ph 9-14 2 Η CH Η 2-SMe-Ph 9- 15 2 Η CH Η 2-SOMe-Ph 9-16 2 Η CH Η 2-SO.Me-Ph 9-17 2 Η CH Η 2-CN-Ph 9-18 2 Η CH Η 2-NO, -Ph 9 -19 2 Η CH Η 2-CF3-Ph 9-20 2 Η CH Η 2-OCF3-Ph 9-21 2 Η CH Η 2-SCF3-Ph 9-22 2 Η CH Η 2-SOCF3-Ph 9-23 2 Η CH Η 2-S02CF3-Ph 9-24 2 Η CH Η 2-C02Me-Ph 9-25 2 Η CH Η 2-Ph-Ph 9-26 2 Η CH Η 2-PhO-Ph 9-27 2 Η CH Η 2,6-FrPh 9-28 2 Η CH Η 2,6-Cl, -Ph 9-29 2 Η CH Η 2,6-Me, -Ph • 79- 200404764 Table 9 (continued) No. Replace Position X J4 R13 R9 Properties [melting point (° C)] 9-30 2 Η CH Η 2,4,6-Cl3-Ph 9-31 2 Η CH Η 2,6-Cl? -4-CF3-Ph 9-32 2 Η CH Η 2,6-Cl, -4-OCF3-Ph 9-33 2 Η CH Η 2? 3,4-Me3-Ph 9 -34 2 Η CH Η 2-Pyn 9-35 2 Η CH Η 3-Pyn 9-36 2 Η CH Η 4-Pyn 9-37 2 Η CH Η 6-Cl-2-Pyn 9-38 2 Η CH Η 6-CF3-2-Pyn 9-39 2 Η CH Η 6-Cl-4-CF3-2-Pyn 9-40 2 Η CH Η 2-Pym 9-41 2 Η CH Η 4-Pym 9-42 2 Η CH Η 4,6-Me2-2-Pym 9-43 2 Η CH Η 4,6- (OMe) 2-2-Pym 9-44 2 Η CH Η 3-Pyd 9-45 2 Η CH Η -CO- NHMe 9-46 2 Η CH Η -CO-NHPh 9-47 2 Η CH Η -CO-NMePh 9-48 2 Η CH Η -CO-NEt (c-Hex) 9-49 2 Η CH Me Me 9-50 2 Η CH Me t-Bu 9-51 2 Η CH Me -CH? -Ph 9-52 2 Η CH Me Me -CHMe-Ph 9-53 2 Η CH -CMe? -Ph 9-54 2 Η CH Me Ph 9-55 2 Η CH Me Me 2-F-Ph 9-56 2 Η CH 2-Cl-Ph 166-167 9-57 2 Η CH Me 3-Cl-Ph 9-58 2 Η CH Me 4-Cl- Ph 9-59 2 Η CH Me 2-Me-Ph 9-60 2 Η CH Me 2-i-Pr-Ph 9-61 2 Η CH Me 2-OMe-Ph 9-62 2 Η CH Me 2-SMe- Ph 9-63 2 Η CH Me 2-SOMe-Ph 9-64 2 Η CH Me 2-SO, Me-Ph 9-65 2 Η CH Me 2-CN-Ph 9-66 2 Η CH Me 2-NO, -Ph 9-67 2 Η CH Me 2-CF3-Ph 9-68 2 Η CH Me 2-OCF, -Ph -80- 200404764 Table 9 (continued)

No. 取代 位置 X J4 R13 R9 9-69 2 Η CH Me 2-SCF3-Ph 9-70 2 Η CH Me 2-S〇CF3-Ph 9-71 2 Η CH Me 2-SO?CF3-Ph 9-72 2 Η CH Me 2-CO?Me-Ph 9-73 2 Η CH Me 2-Ph-]Ph 9-74 2 Η CH Me 2-PhO-Ph 9-75 2 Η CH Me 2,6-F?-Ph 9-76 2 Η CH Me 2,6-CU-Ph 9-77 2 Η CH Me 2,6-Me?-Ph 9-78 2 Η CH Me 2,4,6-Cl3-Ph 9-79 2 Η CH Me 2,6-Cl,-4-CF3-Ph 9-80 2 Η CH Me 256-Cl7-4-OCF3-Ph 9-81 2 Η CH Me 2,3,4-Me3-Ph 9-82 2 Η CH Me 2-Pyn 9-83 2 Η CH Me 3-Pyn 9-84 2 Η CH Me 4-Pyn 9-85 2 Η CH Me 6-Cl-2-Pyn 9-86 2 Η CH Me 6-CF3-2-Pyn 9-87 2 Η CH Me 6-Cl-4-CF3-2-Pyn 9-88 2 Η CH Me 2-Pym 9-89 2 Η CH Me 4-Pym 9-90 2 Η CH Me 4,6-Me?-2-Pym 9-91 2 Η CH Me 4,6-(OMe),-2-Pym 9-92 2 Η CH Me 3-Pyd 9-93 2 Η CH Me -CO-NHMe 9-94 2 Η CH Me -CO-NHPh 9-95 2 Η CH Me -CO-NMePh 9-96 2 Η CH Me -CO-NEt(c-Hex) 9-97 2 Η Ν Me Me 9-98 2 Η Ν Me t-Bu 9-99 2 Η Ν Me -CH?-Ph 9-100 2 Η Ν Me -CHMe-Ph 9-101 2 Η Ν Me -CMe?-Ph 9-102 2 Η Ν Me Ph 9-103 2 Η Ν Me 2-F-Ph 9-104 2 Η Ν Me 2-Cl-Ph 9-105 2 Η Ν Me 3-Cl-Ph 9-106 2 Η Ν Me 4-Cl-Ph 9-107 2 Η Ν Me 2-Me-Ph 9-108 2 Η Ν Me 2-i-Pr-Ph 物性No. Substitution position X J4 R13 R9 9-69 2 Η CH Me 2-SCF3-Ph 9-70 2 Η CH Me 2-S〇CF3-Ph 9-71 2 Η CH Me 2-SO? CF3-Ph 9- 72 2 Η CH Me 2-CO? Me-Ph 9-73 2 Η CH Me 2-Ph-] Ph 9-74 2 Η CH Me 2-PhO-Ph 9-75 2 Η CH Me 2,6-F? -Ph 9-76 2 Η CH Me 2,6-CU-Ph 9-77 2 Η CH Me 2,6-Me? -Ph 9-78 2 Η CH Me 2,4,6-Cl3-Ph 9-79 2 Η CH Me 2,6-Cl, -4-CF3-Ph 9-80 2 Η CH Me 256-Cl7-4-OCF3-Ph 9-81 2 Η CH Me 2,3,4-Me3-Ph 9- 82 2 Η CH Me 2-Pyn 9-83 2 Η CH Me 3-Pyn 9-84 2 Η CH Me 4-Pyn 9-85 2 Η CH Me 6-Cl-2-Pyn 9-86 2 Η CH Me 6 -CF3-2-Pyn 9-87 2 Η CH Me 6-Cl-4-CF3-2-Pyn 9-88 2 Η CH Me 2-Pym 9-89 2 Η CH Me 4-Pym 9-90 2 Η CH Me 4,6-Me? -2-Pym 9-91 2 Η CH Me 4,6- (OMe),-2-Pym 9-92 2 Η CH Me 3-Pyd 9-93 2 Η CH Me -CO- NHMe 9-94 2 Η CH Me -CO-NHPh 9-95 2 Η CH Me -CO-NMePh 9-96 2 Η CH Me -CO-NEt (c-Hex) 9-97 2 Η Ν Me Me 9-98 2 Η Ν Me t-Bu 9-99 2 Η Ν Me -CH? -Ph 9-100 2 Η Ν Me -CHMe-Ph 9-101 2 Η Ν Me -CMe? -Ph 9-102 2 Η Ν Me Ph 9-103 2 Η Ν Me 2-F-Ph 9-104 2 Η Ν Me 2-C l-Ph 9-105 2 Η Ν Me 3-Cl-Ph 9-106 2 Η Ν Me 4-Cl-Ph 9-107 2 Η Ν Me 2-Me-Ph 9-108 2 Η Ν Me 2-i- Pr-Ph Properties

-81- 200404764 第9表（續)-81- 200404764 Table 9 (Continued)

No. 取代 位置 X J4 R13 R9 9-109 2 Η Ν Me 2-OMe-Ph 9-110 2 Η Ν Me 2-SMe-Ph 9-111 2 Η Ν Me 2-SOMe-Ph 9-112 2 Η Ν Me 2-SO,Me-Ph 9-113 2 Η Ν Me 2-CN-Ph 9-114 2 Η Ν Me 2-NCVPh 9-115 2 Η Ν Me 2-CF3-Ph 9-116 2 Η Ν Me 2-OCF3-Ph 9-117 2 Η Ν Me 2-SCF3-Ph 9-118 2 Η Ν Me 2-SOCF3-Ph 9-119 2 Η Ν Me 2-S07CF3-Ph 9-120 2 Η Ν Me 2-CO?Me-Ph 9-121 2 Η Ν Me 2-Ph-Ph 9-122 2 Η Ν Me 2-PhO-Ph 9-123 2 Η Ν Me 2,6-F，-Ph 9-124 2 Η Ν Me 2,6-Cl?-Ph 9-125 2 Η Ν Me 2,6-Me?-Ph 9-126 2 Η Ν Me 2,4,6-drPh 9-127 2 Η Ν Me 2,6-Cl7-4-CF3-Ph 9-128 2 Η Ν Me 2,6-Clr4-OCF3-Ph 9-129 2 Η Ν Me 2,3,4-Me3-Ph 9-130 2 Η Ν Me 2-Pyn 9-131 2 Η Ν Me 3-Pyn 9-132 2 Η Ν Me 4-Pyn 9-133 2 Η Ν Me 6-Cl-2-Pyn 9-134 2 Η Ν Me 6-CF3-2-Pyn 9-135 2 Η Ν Me 6-Cl-4-CF3-2-Pyn 9-136 2 Η Ν Me 2-Pym 9-137 2 Η Ν Me 4-Pym 9-138 2 Η Ν Me 4,6-Me2-2-Pym 9-139 2 Η Ν Me 4,6-(OMe)?-2-Pym 9-140 2 Η Ν Me 3-Pyd " 9-141 2 Η Ν Me -CO-NHMe 9-142 2 Η Ν Me -CO-NHPh 9-143 2 Η Ν Me -CO-NMePh 9-144 2 Η Ν Me -CO-NEt(c-Hex) 9-145 4 Η CH H Me 9-146 4 Η CH H t-Bu 9-147 4 Η CH H -CH?-Ph 9-148 4 Η CH H -CHMe-Ph 9-149 4 Η CH H -CMe,-Ph 物性No. Substitution position X J4 R13 R9 9-109 2 Η Ν Me 2-OMe-Ph 9-110 2 Η Ν Me 2-SMe-Ph 9-111 2 Η Ν Me 2-SOMe-Ph 9-112 2 Η Ν Me 2-SO, Me-Ph 9-113 2 Η Ν Me 2-CN-Ph 9-114 2 Η Ν Me 2-NCVPh 9-115 2 Η Ν Me 2-CF3-Ph 9-116 2 Η Ν Me 2 -OCF3-Ph 9-117 2 Η Ν Me 2-SCF3-Ph 9-118 2 Η Ν Me 2-SOCF3-Ph 9-119 2 Η Ν Me 2-S07CF3-Ph 9-120 2 Η Ν Me 2-CO ? Me-Ph 9-121 2 Η Ν Me 2-Ph-Ph 9-122 2 Η Ν Me 2-PhO-Ph 9-123 2 Η Ν Me 2,6-F, -Ph 9-124 2 Η Ν Me 2,6-Cl? -Ph 9-125 2 Η Ν Me 2,6-Me? -Ph 9-126 2 Η Ν Me 2,4,6-drPh 9-127 2 Η Ν Me 2,6-Cl7- 4-CF3-Ph 9-128 2 Η Ν Me 2,6-Clr4-OCF3-Ph 9-129 2 Η Ν Me 2,3,4-Me3-Ph 9-130 2 Η Ν Me 2-Pyn 9-131 2 Η Ν Me 3-Pyn 9-132 2 Η Ν Me 4-Pyn 9-133 2 Η Ν Me 6-Cl-2-Pyn 9-134 2 Η Ν Me 6-CF3-2-Pyn 9-135 2 Η Ν Me 6-Cl-4-CF3-2-Pyn 9-136 2 Η Ν Me 2-Pym 9-137 2 Η Ν Me 4-Pym 9-138 2 Η Ν Me 4,6-Me2-2-Pym 9 -139 2 Η Ν Me 4,6- (OMe)?-2-Pym 9-140 2 Η Ν Me 3-Pyd " 9-141 2 Η Ν Me -CO-NHMe 9-142 2 Η Ν Me -CO -NHPh 9-143 2 Η Ν Me -CO-NMePh 9-144 2 Η Ν Me -CO-NEt (c-Hex) 9-145 4 Η CH H Me 9-146 4 Η CH H t-Bu 9-147 4 Η CH H -CH? -Ph 9-148 4 Η CH H -CHMe-Ph 9-149 4 Η CH H -CMe, -Ph Physical properties

-82- 200404764-82- 200404764

第9表（續)Table 9 (continued)

No. 取代 位置 X J4 R13 R9 物性 9-150 4 Η CH Η Ph 9-151 4 Η CH Η 2-Cl-Ph 9-152 4 Η CH Η 2-Me-Ph 9-153 4 Η CH Η 2-OMe-Ph 9-154 4 Η CH Η 2-CN-Ph 9-155 4 Η CH Η 2-NCVPh 9-156 4 Η CH Η 2-CF3-Ph 9-157 4 Η CH Η 2-OCF3-Ph 9-158 4 Η CH Η 2-CO?Me-Ph 9-159 4 Η CH Η 2-Ph-Ph 9-160 4 Η CH Η 2-PhO-Ph 9-161 4 Η CH Η 2,6-CU-Ph 9-162 4 Η CH Η 2,6-Me?-Ph 9-163 4 Η CH Η 2,4,6-Cl3-Ph 9-164 4 Η CH Η 2,3,4-Me3-Ph 9-165 4 Η CH Η 2-Pyn 9-166 4 Η CH Η 3-Pyn 9-167 4 Η CH Η 4-Pyn 9-168 4 Η CH Η 2-Pym 9-169 4 Η CH Η 4-Pym 9-170 4 Η CH Η 4,6-Me2-2-Pym 9-171 4 Η CH Η 4?6-(OMe),-2-Pym 9-172 4 Η CH Η 3-Pyd —No. Substitution position X J4 R13 R9 Physical properties 9-150 4 Η CH Η Ph 9-151 4 Η CH Η 2-Cl-Ph 9-152 4 Η CH Η 2-Me-Ph 9-153 4 Η CH Η 2- OMe-Ph 9-154 4 Η CH Η 2-CN-Ph 9-155 4 Η CH Η 2-NCVPh 9-156 4 Η CH Η 2-CF3-Ph 9-157 4 Η CH Η 2-OCF3-Ph 9 -158 4 Η CH Η 2-CO? Me-Ph 9-159 4 Η CH Η 2-Ph-Ph 9-160 4 Η CH Η 2-PhO-Ph 9-161 4 Η CH Η 2,6-CU- Ph 9-162 4 Η CH Η 2,6-Me? -Ph 9-163 4 Η CH Η 2,4,6-Cl3-Ph 9-164 4 Η CH Η 2,3,4-Me3-Ph 9- 165 4 Η CH Η 2-Pyn 9-166 4 Η CH Η 3-Pyn 9-167 4 Η CH Η 4-Pyn 9-168 4 Η CH Η 2-Pym 9-169 4 Η CH Η 4-Pym 9- 170 4 Η CH Η 4,6-Me2-2-Pym 9-171 4 Η CH Η 4? 6- (OMe),-2-Pym 9-172 4 Η CH Η 3-Pyd —

-83- 200404764 通式（I — 9 )-83- 200404764 general formula (I — 9)

1313

R (1-9) 第 1 0表（m=〇、A=- CHsR (1-9) Table 10 (m = 〇, A =-CHs

No. 取代 位置 R1 R2 X J4 J5 R13 物性 〔融點（°C)、 折射率〕 10-1 2 cf3 H H CH CH Ph 251-252 10-2 2 cf3 H H N CH Ph NMR-7 10-3 2 cf3 H H N N Me 10-4 2 cf3 H H N N t-Bu 10-5 2 cf3 H H N N -CH?-Ph 10-6 2 cf3 H H N N -CHMe-Ph 10-7 2 cf3 H H N N -CMe?-Ph 10-8 2 cf3 H H N N Ph 119-120 10-9 2 cf3 H H N N 2-F-Ph 10-10 2 cf3 H H N N 3-F-Ph 10-11 2 cf3 H H N N 4-F-Ph 10-12 2 cf3 H H N N 2-Cl-Ph 1.5581(26〇C) 10-13 2 cf3 H H N N 3-Cl-Ph 1.5490(26〇C) 10-14 2 cf3 H H N N 4-Cl-Ph 1.5492(26〇C) 10-15 2 cf3 H H N N 2-Me-Ph 87-88 10-16 2 cf3 H H N N 3-Me-Ph 89-90 10-17 2 cf3 H H N N 4-Me-Ph 98-99 10-18 2 cf3 H H N N 2-OMe-Ph 124-125 10-19 2 cf3 H H N N 3-OMe-Ph 122-123 10-20 2 cf3 H H N N 4-OMe-Ph 100-101 10-21 2 cf3 H H N N 2-SMe-Ph 90-91 10-22 2 cf3 H H N N 3-SMe-Ph 10-23 2 cf3 H H N N 4-SMe-Ph 104-105 10-24 2 cf3 H H N N 2-SOMe-Ph 176-178 10-25 2 cf3 H H N N 3-SOMe-Ph 10-26 2 cf3 H H N N 4-SOMe-Ph 162-165 10-27 2 cf3 H H N N 2-CN-Ph 10-28 2 cf3 H H N N 2-NO,-Ph 111-112 10-29 2 cf3 H H N N 2-CF3-Ph 123-124 10-30 2 CF? H H N N 2-OCF,-Ph ❿ -84- 200404764 第1 0表（續) No. 取代 位置 R1 R2 X J4 J5 R13 物性 〔融點（°C)、 折射率〕 10-31 2 cf3 H H N N 2-SCF3-Ph 10-32 2 cf3 H H N N 2-SOCF3 - Ph 10-33 2 cf3 H H N N 2-S02CF3-Ph 10-34 2 cf3 H H N N 4-C02Et-Ph 1.5332(22°〇 10-35 2 cf3 H H N N 2?6-F,-Ph 132-134 10-36 2 cf3 H H N N 2,3-Ci-Ph 10-37 2 cf3 H H N N 2,4-CU-Ph 92-93 10-38 2 cf3 H H N N 2,5-Cl广 Ph 10-39 2 cf3 H H N N 2,6-Cl?-Ph 170-171 10-40 2 cf3 H H N N 2-Cl-6-F-Ph 150-151 10-41 2 cf3 H H N N 2,6-Me?-Ph 10-42 2 cf3 H H N N 2-Cl-6-Me-Ph 10-43 2 cf3 H H N N 2,4,6-ClrPh 10-44 2 cf3 H H N N 2,6-Cl厂 4-CF3-Ph 10-45 2 cf3 H H N N 2,6-Cl?-4-OCF3-Ph 10-46 2 cf3 H H N N 2,4,6-Me3-Ph 10-47 2 cf3 H H N N 2-Pyn 10-48 2 cf3 H H N N 3-Pyn 10-49 2 cf3 H H N N 4-Pyn 10-50 2 cf3 H H N N 6-Cl-2-Pyn 10-51 2 cf3 H H N N 6-CF3-2-Pyn 10-52 2 cf3 H H N N 6-Cl-4-CF3-2-Pyn 10-53 2 cf3 H H N N 2-Pym 10-54 2 cf3 H H N N 4-Pym 10-55 2 cf3 H H N N 4,6-Me，2-Pym 10-56 2 cf3 H H N N 456-(OMe),-2-Pym 10-57 2 cf3 H H N N 3-Pyd 10-58 2 cf3 H H N N -C02Et 1.4941(21°〇 10-59 2 cf3 H H N N -CO;H 142-143 10-60 2 cf3 H H N N -CO-NHMe 10-61 2 cf3 H H N N -CO-NHPh 10-62 2 cf3 H H N N -CO-NMePh 10-63 2 cf3 H H N N -CO-NE^ 10-64 2 cf3 H H N N -CO-NEt(c-Hex) 10-65 2 cf3 H H N N -CO-N(i-Pr), 10-66 2 cf3 H 5-Me N N Ph 10-67 2 cf3 H 5-Me N N 2-Cl-Ph 10-68 2 cf3 H 5-Me N N 2-Me-Ph 10-69 2 cf3 H 5-Me N N 2-CF3-Ph 10-70 2 cf3 H 5-Me N N 2,6-Cl,-Ph 10-71 2 CF? H 5-Me N N 2-Cl-6-Me-PhNo. Substitution position R1 R2 X J4 J5 R13 Physical properties [melting point (° C), refractive index] 10-1 2 cf3 HH CH CH Ph 251-252 10-2 2 cf3 HHN CH Ph NMR-7 10-3 2 cf3 HHNN Me 10-4 2 cf3 HHNN t-Bu 10-5 2 cf3 HHNN -CH? -Ph 10-6 2 cf3 HHNN -CHMe-Ph 10-7 2 cf3 HHNN -CMe? -Ph 10-8 2 cf3 HHNN Ph 119-120 10-9 2 cf3 HHNN 2-F-Ph 10-10 2 cf3 HHNN 3-F-Ph 10-11 2 cf3 HHNN 4-F-Ph 10-12 2 cf3 HHNN 2-Cl-Ph 1.5581 (26 〇C) 10-13 2 cf3 HHNN 3-Cl-Ph 1.5490 (26〇C) 10-14 2 cf3 HHNN 4-Cl-Ph 1.5492 (26〇C) 10-15 2 cf3 HHNN 2-Me-Ph 87- 88 10-16 2 cf3 HHNN 3-Me-Ph 89-90 10-17 2 cf3 HHNN 4-Me-Ph 98-99 10-18 2 cf3 HHNN 2-OMe-Ph 124-125 10-19 2 cf3 HHNN 3 -OMe-Ph 122-123 10-20 2 cf3 HHNN 4-OMe-Ph 100-101 10-21 2 cf3 HHNN 2-SMe-Ph 90-91 10-22 2 cf3 HHNN 3-SMe-Ph 10-23 2 cf3 HHNN 4-SMe-Ph 104-105 10-24 2 cf3 HHNN 2-SOMe-Ph 176-178 10-25 2 cf3 HHNN 3-SOMe-Ph 10-26 2 cf3 HHNN 4-SOMe-Ph 162-165 10 -27 2 cf3 HHNN 2-CN-Ph 10-28 2 cf3 HHNN 2-NO, -Ph 111-112 10-29 2 cf3 HHNN 2-CF3-Ph 123-124 10-30 2 CF? HHNN 2-OCF, -Ph ❿ -84- 200404764 Table 10 (continued) No. Substituted position R1 R2 X J4 J5 R13 Physical properties [melting point (° C), refractive index] 10-31 2 cf3 HHNN 2-SCF3-Ph 10-32 2 cf3 HHNN 2-SOCF3-Ph 10-33 2 cf3 HHNN 2-S02CF3-Ph 10-34 2 cf3 HHNN 4-C02Et-Ph 1.5332 (22 ° 〇10-35 2 cf3 HHNN 2? 6-F, -Ph 132-134 10-36 2 cf3 HHNN 2,3-Ci- Ph 10-37 2 cf3 HHNN 2,4-CU-Ph 92-93 10-38 2 cf3 HHNN 2,5-Cl Can Ph 10-39 2 cf3 HHNN 2,6-Cl? -Ph 170-171 10-40 2 cf3 HHNN 2-Cl-6-F-Ph 150-151 10-41 2 cf3 HHNN 2,6-Me? -Ph 10-42 2 cf3 HHNN 2-Cl-6-Me-Ph 10-43 2 cf3 HHNN 2,4,6-ClrPh 10-44 2 cf3 HHNN 2,6-Cl Factory 4-CF3-Ph 10-45 2 cf3 HHNN 2,6-Cl? -4-OCF3-Ph 10-46 2 cf3 HHNN 2, 4,6-Me3-Ph 10-47 2 cf3 HHNN 2-Pyn 10-48 2 cf3 HHNN 3-Pyn 10-49 2 cf3 HHNN 4-Pyn 10-50 2 cf3 HHNN 6-Cl-2-Pyn 10-51 2 cf3 HHNN 6-CF3-2-Pyn 10-52 2 cf3 HHNN 6-Cl-4-CF3-2-Pyn 10-53 2 cf3 HHNN 2-Pym 10-54 2 cf3 HHNN 4-Pym 10-55 2 cf3 HHNN 4,6-Me, 2-Pym 10-56 2 cf3 HHNN 456- (OMe),-2-Pym 10-57 2 cf3 HHNN 3-Pyd 10-58 2 cf3 HHNN -C02Et 1.4941 (21 ° 〇10-59 2 cf3 HHNN -CO; H 142-143 10-60 2 cf3 HHNN -CO-NHMe 10-61 2 cf3 HHNN -CO-NHPh 10-62 2 cf3 HHNN -CO-NMePh 10-63 2 cf3 HHNN -CO-NE ^ 10-64 2 cf3 HHNN -CO-NEt (c-Hex) 10-65 2 cf3 HHNN -CO-N (i-Pr ), 10-66 2 cf3 H 5-Me NN Ph 10-67 2 cf3 H 5-Me NN 2-Cl-Ph 10-68 2 cf3 H 5-Me NN 2-Me-Ph 10-69 2 cf3 H 5 -Me NN 2-CF3-Ph 10-70 2 cf3 H 5-Me NN 2,6-Cl, -Ph 10-71 2 CF? H 5-Me NN 2-Cl-6-Me-Ph

-85- 200404764 第1〇表（續）-85- 200404764 Table 10 (continued)

No. 取代位置 R2 X J4 J5 R1 物性 10-72 10-73 10-74 10-75 10-76 10-77 10-78 10-79 10-80 10-81 10-82 10-83 10-84 10-85 10-86 10-87 10-88 10-89 10-90 10-91 10-92 10-93 10-94 10-95 10-96 10-97 10-98 10-99 10-100 10-101 10-102 10-103 10-104 10-105 10-106 10-107 10-108 10-109 10-110 10-111 10-112 2 2 2 2 2 2 2 2 2 2 2 2 4444444442 2 2 333333333333333333333333333333333333333「T1 FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFX1JX CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCFCF Η 5-Me N N 2,6-Me9-Ph Η 5-Me N N -CH?-Ph Η 5-Me N N -CMe?-Ph Η 4-C1 N N Ph Η 4-C1 N N 2-Cl-Ph Η 4-C1 N N 2-Me-Ph Η 4-C1 N N 2-CFrPh Η 4-C1 N N 2,6-Cl?-Ph Η 4-C1 N N 2-Cl-6-Me-Ph Η 4-C1 N N 2,6-Me?-Ph Η 4-C1 N N -CH2-Ph Η 4-C1 N N -CMe,-Ph Η 5-C1 N N Ph Η 5-C1 N N 2-Cl-Ph Η 5-C1 N N 2-Me-Ph Η 5-C1 N N 2-CF3-Ph Η 5-C1 N N 2,6-Cl，-Ph Η 5-C1 N N 2-Cl-6-Me-Ph Η 5-C1 N N 256-Me9-Ph Η 5-C1 N N -CH2-Ph Η 5-C1 N N -CMe9-Ph Η H N N Me Η H N N t-Bu Η H N N -CH?-Ph Η H N N Ph Η H N N 2-Cl-Ph Η H N N 2-CF3-Ph Η H N N 2,6-Cl9-Ph Η H N N 2-Cl-6-Me-Ph Η H N N 2,6-Me9-Ph Η H N N Me ** Η H N N t-Bu Η H N N -CH,-Ph Η H N N Ph Η H N N 2-Cl-Ph Η H N N 2-CF3-Ph Η H N N 2,6-Cl?-Ph Η H N N 2-Cl-6-Me-Ph Η H N N 2,6-Me?-Ph Η H N N Me " Η H N N t-Bu -86- 200404764 第1 0表（續) No. 取代 位置 R1 R2 X J4 J5 R13 物性 〔融點（°C)〕 10-113 2 chf2 H H N N -CHrPh 10-114 2 chf7 H H N N -CMe?-Ph 10-115 2 CHF? H H N N Ph 10-116 2 CHF? H H N N 2-Cl-Ph 99-100 10-117 2 chf2 H H N N 2-Me-Ph 10-118 2 chf7 H H N N 2-OMe-Ph 10-119 2 chf9 H H N N 2-CF3-Ph 10-120 2 CHF? H H N N 2-OCF3-Ph 10-121 2 CHF, H H N N 2,6-Cl,Ph 10-122 2 CHF, H H N N 2-Cl-6-F-Ph 10-123 2 CHF， H H N N 2-Cl-6-Me-Ph 10-124 2 CHF? H H N N 2,6-Me，-PhNo. Substitution position R2 X J4 J5 R1 Physical properties 10-72 10-73 10-74 10-75 10-76 10-77 10-78 10-79 10-80 10-81 10-82 10-83 10-84 10 -85 10-86 10-87 10-88 10-89 10-90 10-91 10-92 10-93 10-94 10-95 10-96 10-97 10-98 10-99 10-100 10-101 10-102 10-103 10-104 10-105 10-106 10-107 10-108 10-109 10-110 10-111 10-112 2 2 2 2 2 2 2 2 2 2 2 2 4444444442 2 2 333333333333333333333333333333333333333 「 T1 FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF1FFXJCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCFCFC Η 5-Me NN 2,6-Me9-Ph Η 5-Me NN -CH? -Ph Η 5-Me NN -CMe? -Ph Η 4-C1 NN Ph Cl 4-Cl Ph Η 4-C1 NN 2-Me-Ph Η 4-C1 NN 2-CFrPh Η 4-C1 NN 2,6-Cl? -Ph Η 4-C1 NN 2-Cl-6-Me-Ph Η 4-C1 NN 2,6-Me? -Ph Η 4-C1 NN -CH2-Ph Η 4-C1 NN -CMe, -Ph Η 5-C1 NN Ph Η 5-C1 NN 2-Cl-Ph Η 5-C1 NN 2 -Me-Ph Η 5-C1 NN 2-CF3-Ph Η 5-C1 NN 2,6-Cl, -Ph Η 5-C1 NN 2-Cl-6-Me-Ph Η 5-C1 NN 256-Me9- Ph Η 5-C1 NN -CH2-Ph Η 5-C1 NN -CMe9-Ph Η HNN Me Η HNN t-Bu Η HNN -CH? -Ph Η HNN Ph Η HNN 2-Cl-Ph Η HNN 2-CF3-Ph Η HNN 2,6-Cl9-Ph Η HNN 2-Cl-6-Me-Ph Η HNN 2,6-Me9-Ph Η HNN Me ** Η HNN t- Bu Η HNN -CH, -Ph Η HNN Ph Η HNN 2-Cl-Ph Η HNN 2-CF3-Ph Η HNN 2,6-Cl? -Ph Η HNN 2-Cl-6-Me-Ph Η HNN 2, 6-Me? -Ph Η HNN Me " Η HNN t-Bu -86- 200404764 Table 10 (continued) No. Substituted position R1 R2 X J4 J5 R13 Physical properties [melting point (° C)] 10-113 2 chf2 HHNN -CHrPh 10-114 2 chf7 HHNN -CMe? -Ph 10-115 2 CHF? HHNN Ph 10-116 2 CHF? HHNN 2-Cl-Ph 99-100 10-117 2 chf2 HHNN 2-Me-Ph 10 -118 2 chf7 HHNN 2-OMe-Ph 10-119 2 chf9 HHNN 2-CF3-Ph 10-120 2 CHF? HHNN 2-OCF3-Ph 10-121 2 CHF, HHNN 2,6-Cl, Ph 10-122 2 CHF, HHNN 2-Cl-6-F-Ph 10-123 2 CHF, HHNN 2-Cl-6-Me-Ph 10-124 2 CHF? HHNN 2,6-Me, -Ph

-87- 13 200404764 通式（I — 10)-87- 13 200404764 general formula (I — 10)

R1-S02(R2)NR1-S02 (R2) N

R (I-10) 第 1 1表（m=〇、A=- CH2 -) No. 取代 位置 Rl R2 X J4 J5 R13 物性 〔融點（°C)〕 11-1 2 cf3 H H N N Me 11-2 2 cf3 H H N N t-Bu 11-3 2 cf3 H H N N -CHrPh 11-4 2 cf3 H H N N -CHMe-Ph 11-5 2 cf3 H H N N -CMe?-Ph 11-6 2 cf3 H H N N Ph 11-7 2 cf3 H H N N 2-Cl-Ph 141-142 11-8 2 cf3 H H N N 3-Cl-Ph 11-9 2 cf3 H H N N 4-Cl-Ph 11-10 2 cf3 H H N N 2-Me-Ph 11-11 2 cf3 H H N N 2-OMe-Ph 156-157 11-12 2 cf3 H H N N 2-SMe-Ph 11-13 2 cf3 H H N N 2-SOMe-Ph 11-14 2 cf3 H H N N 2-S02Me-Ph 11-15 2 cf3 H H N N 2-CN-Ph 11-16 2 cf3 H H N N 2-NOrPh 11-17 2 cf3 H H N N 2-CF3-Ph 11-18 2 cf3 H H N N 2-OCF3-Ph 11-19 2 cf3 H H N N 4-C02Et-Ph 11-20 2 cf3 H H N N 2-Ph-Ph 11-21 2 cf3 H H N N 2-PhO-Ph 11-22 2 cf3 H H N N 2,6-FrPh 11-23 2 cf3 H H N N 2,6-Cl2-Ph 163-164 11-24 2 cf3 H H N N 2-Cl-6-F-Ph 11-25 2 cf3 H H N N 2,6-Me2-Ph 11-26 2 cf3 H H N N 2-Cl-6-Me-Ph 11-27 2 cf3 H H N N 2,6-(OMe)7-Ph 11-28 2 cf3 H H N N 2,6-(CF3)2-Ph 11-29 2 cf3 H H N N 2,6-(OCF,),-PhR (I-10) Table 11 (m = 〇, A =-CH2-) No. Substitution position Rl R2 X J4 J5 R13 Physical properties [melting point (° C)] 11-1 2 cf3 HHNN Me 11-2 2 cf3 HHNN t-Bu 11-3 2 cf3 HHNN -CHrPh 11-4 2 cf3 HHNN -CHMe-Ph 11-5 2 cf3 HHNN -CMe? -Ph 11-6 2 cf3 HHNN Ph 11-7 2 cf3 HHNN 2- Cl-Ph 141-142 11-8 2 cf3 HHNN 3-Cl-Ph 11-9 2 cf3 HHNN 4-Cl-Ph 11-10 2 cf3 HHNN 2-Me-Ph 11-11 2 cf3 HHNN 2-OMe-Ph 156-157 11-12 2 cf3 HHNN 2-SMe-Ph 11-13 2 cf3 HHNN 2-SOMe-Ph 11-14 2 cf3 HHNN 2-S02Me-Ph 11-15 2 cf3 HHNN 2-CN-Ph 11-16 2 cf3 HHNN 2-NOrPh 11-17 2 cf3 HHNN 2-CF3-Ph 11-18 2 cf3 HHNN 2-OCF3-Ph 11-19 2 cf3 HHNN 4-C02Et-Ph 11-20 2 cf3 HHNN 2-Ph-Ph 11-21 2 cf3 HHNN 2-PhO-Ph 11-22 2 cf3 HHNN 2,6-FrPh 11-23 2 cf3 HHNN 2,6-Cl2-Ph 163-164 11-24 2 cf3 HHNN 2-Cl-6- F-Ph 11-25 2 cf3 HHNN 2,6-Me2-Ph 11-26 2 cf3 HHNN 2-Cl-6-Me-Ph 11-27 2 cf3 HHNN 2,6- (OMe) 7-Ph 11-28 2 cf3 HHNN 2,6- (CF3) 2-Ph 11-29 2 cf3 H H N N 2,6- (OCF,),-Ph

-88- 200404764 第 1 1表（m=〇、A=- CH2〇 M 取代 W No. _ „ R1 R** 位置-88- 200404764 Table 11 (m = 〇, A =-CH2〇 M replaces W No. _ „R1 R ** position

X J4 J5 R1 物性 11-30 11-31 11-32 11-33 11-34 11-35 11-36 11-37 11-38 11-39 11-40 11-41 11-42 11-43 11-44 11-45 11-46 11-47 11-48 11-49 2 33333333333333333333 ffffffffffffffffffffcccccccccccccccccccc JXJlJlJXJXJXJXJlTXJXTTAJlJlJlJlJXTliJlTl ΤΓ ΤΓ ΤΓ F F ΤΓ ΤΓ ΤΓ ΤΓΤΓΤΓΤΓΤΓ-ΤΓΤΓΤΓ-ΤΓΧΚΧΤΓ- ΤΓ H N N 2,4,6-Cl3-Ph H N N 2,6-Cl2-4-CF3-Ph H N N 2?6-Clr4-OCF3-Ph H N N 2,4,6-Me3-Ph H N N 2-Pyn H N N 3-Pyn H N N 4-Pyn H N N 2-Pym H N N 4-Pym H N N 4,6-Me2-2-Pym H N N 4,6-(OMe)2-2-Pym H N N 3-Pyd H N N -C02Et H N N -CO;H H N N -CO-NHMe H N N -CO-NHPh H N N -CO-NMe2 H N. N -CO-NMePh H N N -CO-NEt(c-Hex) H N N -CO-N(i-Pr)，X J4 J5 R1 Physical properties 11-30 11-31 11-32 11-33 11-34 11-35 11-36 11-37 11-38 11-39 11-40 11-41 11-42 11-43 11-44 11-45 11-46 11-47 11-48 11-49 2 33333333333333333333 ffffffffffffffffffffffcccccccccccccccccccc JXJlJlJlJXJXJXJXJXJlTXJXTTAJlJlJlJlJlJXTliJ6-Cl-T-Γ-TΓ-TΓ 4-CF3-Ph HNN 2? 6-Clr4-OCF3-Ph HNN 2,4,6-Me3-Ph HNN 2-Pyn HNN 3-Pyn HNN 4-Pyn HNN 2-Pym HNN 4-Pym HNN 4,6- Me2-2-Pym HNN 4,6- (OMe) 2-2-Pym HNN 3-Pyd HNN -C02Et HNN -CO; HHNN -CO-NHMe HNN -CO-NHPh HNN -CO-NMe2 H N. N -CO -NMePh HNN -CO-NEt (c-Hex) HNN -CO-N (i-Pr),

-89- 200404764 通式（i)-89- 200404764 general formula (i)

R1-S02(R2)NR1-S02 (R2) N

Ά一 Q ⑴ 第 1 2表（R1 二CF3、R2=H、m=0、A=- CH$Ά 一 Q ⑴ Table 12 (R1, CF3, R2 = H, m = 0, A =-CH $

No. 取代 位置 12-1 2 12-2 12-3 12-4 12-5 12-6 12-7 12-8 12-9 3 4 2 3 4 2 3 4 X Η Η Η Η Η Η Η Η ΗNo. Replacement position 12-1 2 12-2 12-3 12-4 12-5 12-6 12-7 12-8 12-9 3 4 2 3 4 2 3 4 X Η Η Η Η Η Η Η Η Η

Q 物性 〔融點rc)、折射率〕Q Physical properties (melting point rc), refractive index

1.5455(24°〇1.5455 (24 °.

& 一 Ν 172.1& Ν 172.1

115.4 -90- 200404764 通式（I — 1 1)115.4 -90- 200404764 general formula (I — 1 1)

GH^Et3 第1 3表GH ^ Et3 Table 1 3

No. J5 R9 物性 〔融點（°C)、折射率〕 13-1 C-SMe 2-Cl-Ph 101-103 13-2 CH 2-Cl-Ph 101-103 13-3 CH 2,6-MerPh 123-125 13-4 CH 2-Cl-6-Me-Ph 1.5488(26°〇 -9 1-No. J5 R9 Physical properties [melting point (° C), refractive index] 13-1 C-SMe 2-Cl-Ph 101-103 13-2 CH 2-Cl-Ph 101-103 13-3 CH 2,6- MerPh 123-125 13-4 CH 2-Cl-6-Me-Ph 1.5488 (26 ° 〇-9 1-

200404764 將第1表至第1 3表中的N M R數據記載於弟！· 4表。200404764 Record the N M R data in Tables 1 to 13 in your brother! · 4 tables.

第1 4表 NMR No. 化合物No· ----- lH-NMR(CDCl3/TMS, (5 ifippm) 1 1-257 10.82(lH，bs)，7.62-7.26(9H，m)，4.97(2H，s)，4.01(3H，s) 2 3-83 7.6-7.4(8H，m)，5.3(2H，q)，3.5(3H，s) 3 5-29 10.39(lH，s)，7.83(lH，s)，7.57-7.33(8H，m)，5.62(lH，q)，1.97(3H,d) 4 5-50 9.45(lH，s)，7.55(lH,s)，7.50-7.25(8H，m)，5.31(lH，dd)，4.60(lH，br)， 4.04(lH，dd), 3.95(lH，dd) 5 5-64 11.50(lH，s)，8.01(lH，dd)，7.86(lH，d)，7.72-7.70(2H，m)， 7.56-7.50(2H，m)，7.42-7.25(3H，m)，5.92(2H，s) 6 5-93 10.78(lH，s)，7.92(lH，dd)，7.68-7.65(2H，m)，7.50(lH，dd)， 7.43-7.25(5H，m)，5.01(2H，s)，4.19(3H，s) 7 10-2 9.3(lH，br)，8.21(lH，s)，8.01-7.99(2H，s)，7.62(lH，d)， 7.45-7.39(5H，m)，7.26(lH，dd)，5.34(2H，s) 8 6-339 9.5(lH，s)，7.50(lH，d)，7.44(lH，dd)，7.39-7.23(5H，m)，4.49(2H，s)， 3.85(2H，dd)，3.66(2H，dd) 9 6-361 7.57-6.92(10H，m)，4.58(2H，dd)，3.73(2H，m)，3.48(2H，m)，2.41(6H，s)， 10 6-362 9,07(lH，s)，8.35(lH，s),7.45-7.13(6H，m)，6.80(2H，s)，4.42(2H，s)， 3.56(4H,dd), 2.37(6H，s)，2.22(3H,s)Table 14 NMR No. Compound No. ----- lH-NMR (CDCl3 / TMS, (5 ifippm) 1 1-257 10.82 (lH, bs), 7.62-7.26 (9H, m), 4.97 (2H , S), 4.01 (3H, s) 2 3-83 7.6-7.4 (8H, m), 5.3 (2H, q), 3.5 (3H, s) 3 5-29 10.39 (lH, s), 7.83 (lH , S), 7.57-7.33 (8H, m), 5.62 (lH, q), 1.97 (3H, d) 4 5-50 9.45 (lH, s), 7.55 (lH, s), 7.50-7.25 (8H, m), 5.31 (lH, dd), 4.60 (lH, br), 4.04 (lH, dd), 3.95 (lH, dd) 5 5-64 11.50 (lH, s), 8.01 (lH, dd), 7.86 ( lH, d), 7.72-7.70 (2H, m), 7.56-7.50 (2H, m), 7.42-7.25 (3H, m), 5.92 (2H, s) 6 5-93 10.78 (lH, s), 7.92 (lH, dd), 7.68-7.65 (2H, m), 7.50 (lH, dd), 7.43-7.25 (5H, m), 5.01 (2H, s), 4.19 (3H, s) 7 10-2 9.3 ( lH, br), 8.21 (lH, s), 8.01-7.99 (2H, s), 7.62 (lH, d), 7.45-7.39 (5H, m), 7.26 (lH, dd), 5.34 (2H, s) 8 6-339 9.5 (lH, s), 7.50 (lH, d), 7.44 (lH, dd), 7.39-7.23 (5H, m), 4.49 (2H, s), 3.85 (2H, dd), 3.66 ( 2H, dd) 9 6-361 7.57-6.92 (10H, m), 4.58 (2H, dd), 3.73 (2H, m), 3.48 (2H, m), 2.41 (6H, s), 10 6-362 9 , 07 ( lH, s), 8.35 (lH, s), 7.45-7.13 (6H, m), 6.80 (2H, s), 4.42 (2H, s), 3.56 (4H, dd), 2.37 (6H, s), 2.22 (3H, s)

-92- 200404764 實例1 (1-1)· 2-(2-硝；基）-4 -苯基- 2,4 -二氫 __3H-1，2,4 -三哩 基-3-酮之合成 將 4 -苯基- 2,4-二氫- 3H-1，2,4-***基-3-酮（161 克，1〇 毫莫耳）與碳酸鉀（1.66克，12毫莫耳）懸浮於Ν，Ν-二甲基 甲醯胺（35毫升）中，隨後加入2 -硝；基氯（1.8〇克，ι〇·5 毫莫耳），在5 0 °C下加熱攪拌4小時。於室溫冷卻後，加 入冰水、將析出得結晶用醚洗淨’而得到2 - ( 2 -硝苄基）-4 -苯基- 2,4 -二氫- 3H-1，2,4 -三嗤基-3-酮（2.73克，92%回收 率）。 (1-2)· 2-(2-胺基苄基）-4 -苯基- 2,4 -二氫- 3H-1，2,4 -三 唑基-3-酮之合成 將2-(2-硝苄基）-4-苯基- 2,4-二氫- 3H-1，2,4-***基- 3-酮（2.6克，8·8毫莫耳）、氯化亞錫二水合物（7.93克，35 毫莫耳）添加至乙醇（30毫升）及濃鹽酸（30毫升）的混合溶 劑中’加熱迴流6小時。於室溫冷卻後，加入20%的氫 化;鈉水溶液使反應液爲鹼性，而萃取出氯仿。用水沖洗4 次氯仿層後，以飽和食鹽水沖洗i次，經無水硫酸鈉乾以 燥I留去溶劑。用己烷洗淨析出的結晶，而得到2_(2_胺基 苄基）-4-苯基- 2,4 -二氫- 3H-1，2，4-***基-3-酮（2.33 克，100 %回收率）。 (1-3)· 4-苯基- 2-(2-三氟甲烷磺醯胺苄基）-2,4-二氫- 311，2,4-***基-3-酮（化合物>1〇.1-23)之合成 將 2-(2-胺基苄基）-4-苯基- 2,4-二氫- 3H-1，2,4-***基 -93- 200404764 -3 -酮（0.30克’ 1.1豪莫耳）及三乙胺（〇M克，1.4毫莫耳） 溶解於氯仿（5毫升）後，把反應溶液冷卻至_丨〇 π。隨後將 用0.5毫升氯仿稀釋三氟甲烷磺酸無水物（0.39克，4毫 莫耳）之溶液滴下2分鐘。在相同溫度下攪拌2小時後’ 緩慢地將反應溫度上升至室溫且攪拌1 〇小時。反應終了 後’在減壓下館去氯仿，用矽膠管柱層析法純化殘渣，而 得到4 -苯基-2-(2 -三氟甲烷磺醯胺苄基）_2,4_二氫_3H_ 1，2,4-***基-3-酮（〇·36克，79%回收率）。融點爲141-142 X：。 實例2 (2-1)· 2-(2-氯苯基）-4-(2-硝苄基）-2,4-二氫-311- 1，2,4-***基-3-酮之合成 將 2-(2-氯苯基）-2,4-二氫- 3Η-1，2,4-***基-3-酮（1.00 克’ 5·1毫莫耳）及與碳酸鈉（〇·74克，5.4毫莫耳）於Ν.Ν-二甲醯基醯胺（25毫升）中溶解 '懸浮，且添加2_硝苄基 氯於5 0 °C下加熱攪拌2小時。於室溫下冷卻後加入冰水， 萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸乙酯層1次後， 以無水硫酸鈉乾燥餾出溶劑。用己烷-***（1 : 1)混合液洗 淨析出的結晶，而得到2 - ( 2 -氯苯基）_ 4 - ( 2 -硝苄基）-2，4 -二 氫-3H-1，2,4-***基-3-酮（1.37克，81.3%回收率）。融點 爲 8 5.5°C。 (2-2)· 4·· (2-胺基苄基）-2-(2-氯苯基）-2,4 -二氫-3H- 1，2,4-***基-3-酮之合成 200404764 用乙醇（30毫升）與水（1 5毫升）溶解1-(2-氯苯基）-2_ (2 -硝苄基）-2，4 -二氫-3 Η - 1，2，4 -***基-3 _ 酮（1 · 2 5 克，3 · 8 毫莫耳）、鐵粉末（1·〇6克、18.9毫莫耳）、氯化銨（0.10克， 1 . 9毫莫耳），加熱迴流2小時。於室溫下冷卻後吸引過量 的反應液，萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸乙酯 層1次後，以無水硫酸鈉乾燥餾出溶劑。用己烷-***（1 : 1 ) 混合液洗淨析出的結晶，而得到4 - ( 2 -胺基苄基）-2 - ( 2 -氯 苯基）-2,4-二氫-3Η-1，2,4-***基-3-酮（0.55 克，48.2% 回 收率）。融點爲1 6 8 · 6 t：。 (2-3). 2_(2_氯苯基）_4-(2_三氟甲烷磺醯胺基苄基）- 2.4- 二氫-3^1-1，2,4-***基-3-酮（化合物1^〇.2-27)之合成 用氯仿（20毫升）溶解4-(2 -胺基苄基）-2-(2 -氯苯基）- 2.4- 二氫-3H-1，2,4-***基-3-酮（0.50克，ΐ·7毫莫耳）及三 乙胺（〇 . 1 8克’ 1 · 8毫吴耳）後’於-1 0 °C下冷卻反應溶液。 且將三氟甲烷磺酸（0.47克，1.7毫莫耳）滴下20分鐘。在 相同溫度下攪拌2小時後加水，且再加入6N鹽酸以酸化 反應液，而萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸乙酯 層1次後，以無水硫酸鈉乾燥餾出溶劑。用砂膠管柱層析 法純化殘澄’而得到2 - ( 2 -氯苯基）-4 - ( 2 -三氟甲院擴醯胺 基苄基）-2,4-二氫-3H-1，2,4-***基-3-酮（0,38 克，51.7% 回收率）。融點爲1 8 7 · 9 °C。 實例3 (3-1)· 4-(2 -硝韦基）-1-(2 -三氟甲苯基）_5(4H) -四卩坐啉 -95- 200404764 酮之合成 用N，N -二甲基甲醯胺（2 5毫升）溶解、懸浮1 - ( 2 -三氟 甲苯基）-5(4H) -三嗤啉酮（2·5克，11毫莫耳）與碳酸鈉（2·2 克’ 1 6毫莫耳），且於5 0 °C下加入對甲苯磺酸2 -硝；基酯 (3 · 7克，1 2毫莫耳）加熱攪拌2小時。於室溫下冷卻後加 入冰水，萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸乙酯層 1次後，以無水硫酸鈉乾燥餾出溶劑。用己烷洗淨析出的 結晶，而得到4-(2-硝苄基）-1-(2-三氟甲苯基）-5(4H)-四唑 啉酮（3 · 8克，9 4 %回收率）。 (3-2). 4-(2-胺苄基）-1-(2-三氟甲苯基）-5(4H)-四唑啉 酮之合成 將 4-(2_硝苄基）-1-(2 -三氟甲苯基）-5(4H) -四唑啉酮 (2·〇克，5豪莫耳）、氯化亞錫二水合物（4·9克，22毫莫 耳）溶解於乙醇（20毫升）及濃鹽酸（20毫升）中，且加熱迴 流5小時。於室溫下冷卻後加入1 〇 %氫氧化鈉水溶液以 鹼化反應液，且萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸 乙酯層1次後，以無水硫酸鈉乾燥餾出溶劑。用己院洗淨 析出的結晶，而得到4 - ( 2 -胺苄基）-1 - (2 -三氟甲苯基）_ 5(4Η) -四卩坐啉酮（1.3克，70%回收率）。 (3-3)· 1-(2_三氟甲苯基）-4_(2 -三氟甲烷磺醯胺苄 基）-5(4以-四唑啉酮（化合物>1〇.3-38)之合成 將4-(2-胺；基）-1_( 2-三氟甲苯基）-5(4Η)-四唑啉酮 (0.50克，1.5毫莫耳）及咪唑（ο.%克，3·8毫莫耳）溶解於 氯仿（7毫升）後，於-1〇。(；下冷卻反應溶液。然後在20分 -96- 200404764 鐘內滴下三氟甲烷磺酸無水物（0.5 5克’ 1.9毫莫耳）°在 相同溫度下攪拌2小時候加入冰水，然後加入6 N鹽酸以 酸化反應液，且萃取出醋酸乙酯。用飽和食鹽水沖洗醋酸 乙酯層1次後，以無水硫酸鈉乾燥餾出溶劑。用矽膠管柱 層析法（己烷：醋酸乙酯=2:1)純化殘渣，而得到1-(2-三 氟甲苯基）-4-(2-三氟甲烷磺醯胺苄基）-5(4H)-四唑啉酮 (0.2克，2 9 %回收率）。熔點爲9 5 - 9 7 °C。 實例4 (4-1). 2-(2,6-二氯苯基）-4-[2-(N-異丙羰基-N-三氟 甲基磺醯胺苄基）卜2,4-二氫- 3H-1，2,4-***基-3-酮之合成 (化合物 Νο·2-247) 將2-(2,6 -二氯苯基）-4-(2 -三氟甲基磺醯胺苄基）-2,4-二氫-3H-1,2,4-***基-3-酮（0.30克，0.6毫莫耳）及三乙 胺（〇·〇7克，0·7毫莫耳）溶解於四氫呋喃（20毫升）中，加 入氯異丁醯（0.08克，0.7毫莫耳）於室溫下攪拌5小時。 將冰水注入反應液中，萃取出醋酸乙酯。用矽膠管柱層析 法[η -己烷-醋酸乙酯（1 : 1 )]純化殘渣，而得到2 2，6 -二氯 苯基）-4-[2-(Ν-異丙羰基三氟甲基磺醯胺苄基）卜2,4-二 氫-3Η-1，2,4-***基-3,酮（0.25克，72.7%回收率）。融點 爲 55.6-61.9°C。 (4-2). N-(2,6 — —'氣苯基）-Ν’- [2-(N-三氟甲基礦酸基 -N-苯基羰基）胺苄基]-2-咪唑啶酮 將N-(2,6-二氯苯基）-N，-(2-三氟甲基磺醯胺苄基）-2- 200404764 咪唑啶酮（0.30克，0.64毫莫耳）及三乙胺（〇.07克，〇.70 毫莫耳）溶解於四氫呋喃（15毫升）中’且添加苯甲醯氯（0·09 克，0 · 6 4毫莫耳）於室溫下攪拌7小時。然後，將水加入 以純化出醋酸乙酯。用飽和食鹽水沖洗醋酸乙醋層1次 後，以無水硫酸鈉乾燥餾出溶劑。用矽膠管柱層析法純化’ 而得到N-(2,6 —二氯苯基）_n，-[2-(N -三氟甲基磺醒基 苯基羰基）胺苄基卜2-咪唑啶酮（0.09克，24.6%回收率）。 熔點爲9 5 - 9 7 °C。-92- 200404764 Example 1 (1-1) · 2- (2-nitro; yl) -4-phenyl-2,4-dihydro__3H-1,2,4-trimile-3-one Synthesis of 4-phenyl-2,4-dihydro-3H-1,2,4-triazolyl-3-one (161 g, 10 mmol) with potassium carbonate (1.66 g, 12 mmol) ) Suspended in Ν, Ν-dimethylformamide (35 ml), followed by the addition of 2-nitrate; chloro (1.80 g, 0.5 mmol), heated and stirred at 50 ° C for 4 hour. After cooling at room temperature, ice-water was added, and the precipitated crystals were washed with ether to obtain 2- (2-nitrobenzyl) -4-phenyl-2,4-dihydro-3H-1,2,4. -Trimethyl-3-one (2.73 g, 92% recovery). (1-2) · Synthesis of 2- (2-aminobenzyl) -4-phenyl-2,4-dihydro-3H-1,2,4-triazolyl-3-one 2-nitrobenzyl) -4-phenyl-2,4-dihydro-3H-1,2,4-triazolyl-3-one (2.6 g, 8.8 mmol), stannous chloride The dihydrate (7.93 g, 35 mmol) was added to a mixed solvent of ethanol (30 ml) and concentrated hydrochloric acid (30 ml) and heated under reflux for 6 hours. After cooling at room temperature, 20% hydrogenation was added; the reaction solution was made alkaline with an aqueous sodium solution, and chloroform was extracted. The chloroform layer was washed 4 times with water, and then washed with saturated brine i times, and dried over anhydrous sodium sulfate to dry the solvent. The precipitated crystals were washed with hexane to obtain 2- (2-aminobenzyl) -4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one (2.33 G, 100% recovery). (1-3) 4-phenyl-2- (2-trifluoromethanesulfonamidobenzyl) -2,4-dihydro-311,2,4-triazolyl-3-one (compounds> 10.1-23) Synthesis of 2- (2-aminobenzyl) -4-phenyl-2,4-dihydro-3H-1,2,4-triazolyl-93-200404764-3 -Ketone (0.30 g '1.1 mol) and triethylamine (0 M g, 1.4 mmol) were dissolved in chloroform (5 ml), and the reaction solution was cooled to ∼0π. Subsequently, a solution of anhydrous trifluoromethanesulfonic acid (0.39 g, 4 mmol) diluted with 0.5 ml of chloroform was dropped for 2 minutes. After stirring at the same temperature for 2 hours', the reaction temperature was slowly raised to room temperature and stirred for 10 hours. After the reaction was completed, chloroform was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-phenyl-2- (2-trifluoromethanesulfonamidobenzyl) _2,4_dihydro_3H_ 1,2,4-triazolyl-3-one (0.36 g, 79% recovery). The melting point is 141-142 X :. Example 2 (2-1) · 2- (2-chlorophenyl) -4- (2-nitrobenzyl) -2,4-dihydro-311-1,2,4-triazolyl-3-one The synthesis of 2- (2-chlorophenyl) -2,4-dihydro-3,1,2,4-triazolyl-3-one (1.00 g '5.1 mmol) and sodium carbonate (.74 g, 5.4 mmol) was dissolved in N.N-dimethylfluorenamide (25 ml) and suspended, and 2-nitrobenzyl chloride was added and stirred with heating at 50 ° C for 2 hours. After cooling at room temperature, ice water was added, and ethyl acetate was extracted. After the ethyl acetate layer was washed once with saturated saline, the solvent was distilled off over anhydrous sodium sulfate. The precipitated crystals were washed with a hexane-ether (1: 1) mixture to obtain 2- (2-chlorophenyl) _4- (2-nitrobenzyl) -2,4-dihydro-3H-1. , 2,4-triazolyl-3-one (1.37 g, 81.3% recovery). The melting point is 8 5.5 ° C. (2-2) 4 ... (2-aminobenzyl) -2- (2-chlorophenyl) -2,4-dihydro-3H-1,2,4-triazolyl-3-one Synthesis of 200404764 Dissolve 1- (2-chlorophenyl) -2_ (2-nitrobenzyl) -2,4-dihydro-3 hydrazone -1,2 with ethanol (30 ml) and water (15 ml), 4-triazolyl-3_one (1.25 g, 3.8 mmol), iron powder (1.06 g, 18.9 mmol), ammonium chloride (0.10 g, 1.9 mmol) Mol), heat to reflux for 2 hours. After cooling at room temperature, the excess reaction liquid was attracted, and ethyl acetate was extracted. After the ethyl acetate layer was washed once with saturated saline, the solvent was distilled off over anhydrous sodium sulfate. The precipitated crystals were washed with a hexane-ether (1: 1) mixture to obtain 4-(2-aminobenzyl) -2-(2-chlorophenyl) -2,4-dihydro-3Η- 1,2,4-triazolyl-3-one (0.55 g, 48.2% recovery). The melting point is 1 6 8 · 6 t :. (2-3). 2_ (2_chlorophenyl) _4- (2_trifluoromethanesulfonamidobenzyl) -2.4-dihydro-3 ^ 1-1,2,4-triazolyl-3 -Synthesis of ketone (Compound 1 ^ 〇.2-27) Chloroform (20 ml) was used to dissolve 4- (2-aminobenzyl) -2- (2-chlorophenyl) -2.4-dihydro-3H-1 , 2,4-triazolyl-3-one (0.50 g, ΐ · 7 mmol) and triethylamine (0.18 g '1.8 mmol), at -10 ° C The reaction solution was cooled. And trifluoromethanesulfonic acid (0.47 g, 1.7 mmol) was dropped for 20 minutes. After stirring at the same temperature for 2 hours, water was added, and 6N hydrochloric acid was further added to acidify the reaction solution, and ethyl acetate was extracted. After the ethyl acetate layer was washed once with saturated saline, the solvent was distilled off over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography to obtain 2-(2 -chlorophenyl) -4-(2 -trifluoromethanesulfonylaminobenzyl) -2,4-dihydro-3H-1 , 2,4-triazolyl-3-one (0,38 g, 51.7% recovery). The melting point is 1 8 7 · 9 ° C. Example 3 (3-1) · 4- (2-Nitraweiyl) -1- (2-trifluorotolyl) _5 (4H) -tetraperoxoline-95- 200404764 Ketone N, N -di Methylformamide (2.5 ml) was dissolved and suspended in 1-(2 -trifluorotolyl) -5 (4H) -triazolinone (2.5 g, 11 mmol) and sodium carbonate (2 · 2 g '16 mmol), and p-toluenesulfonic acid 2-nitrate; base ester (3.7 g, 12 mmol) was stirred at 50 ° C for 2 hours. After cooling at room temperature, ice water was added and ethyl acetate was extracted. After the ethyl acetate layer was washed once with saturated saline, the solvent was distilled off over anhydrous sodium sulfate. The precipitated crystals were washed with hexane to obtain 4- (2-nitrobenzyl) -1- (2-trifluorotolyl) -5 (4H) -tetrazolinone (3.8 g, 94%). Recovery rate). (3-2). Synthesis of 4- (2-aminobenzyl) -1- (2-trifluorotolyl) -5 (4H) -tetrazolinone 4- (2-nitrobenzyl) -1 -(2-trifluorotolyl) -5 (4H) -tetrazolinone (2.0 g, 5 mol), stannous chloride dihydrate (4.9 g, 22 mmol) dissolved In ethanol (20 ml) and concentrated hydrochloric acid (20 ml), and heated under reflux for 5 hours. After cooling at room temperature, 10% aqueous sodium hydroxide solution was added to basify the reaction solution, and ethyl acetate was extracted. After the ethyl acetate layer was washed once with saturated saline, the solvent was distilled off over anhydrous sodium sulfate. The precipitated crystals were washed with the existing compound to obtain 4-(2 -aminobenzyl) -1-(2-trifluorotolyl) _ 5 (4Η) -tetrapyrazinone (1.3 g, 70% recovery rate). ). (3-3) 1- (2-trifluorotolyl) -4_ (2-trifluoromethanesulfonamidobenzyl) -5 (4 to -tetrazolinone (compounds> 10.3-38 ) Synthesis of 4- (2-amine; yl) -1_ (2-trifluorotolyl) -5 (4Η) -tetrazolinone (0.50 g, 1.5 mmol) and imidazole (ο.% G, (3.8 mmol) was dissolved in chloroform (7 ml), and then the reaction solution was cooled at -10. (;; then trifluoromethanesulfonic acid anhydrous (0.5 5 g) was dripped within 20 minutes -96-200404764 '1.9 millimolar) ° Stir at the same temperature for 2 hours, add ice water, then add 6 N hydrochloric acid to acidify the reaction solution, and extract the ethyl acetate. Rinse the ethyl acetate layer once with saturated brine, and dry with water The solvent was distilled off after drying over sodium sulfate. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain 1- (2-trifluorotolyl) -4- (2-trifluoromethane). Sulfabenzyl) -5 (4H) -tetrazolinone (0.2 g, 29% recovery). Melting point is 9 5-9 7 ° C. Example 4 (4-1). 2- (2, 6-dichlorophenyl) -4- [2- (N-isopropylcarbonyl-N-trifluoromethylsulfonamidobenzyl) b 2,4-dihydro-3H-1,2,4-triazole Synthesis of Benzyl-3-one Compound No. · 2-247) 2- (2,6-dichlorophenyl) -4- (2-trifluoromethylsulfonamidobenzyl) -2,4-dihydro-3H-1,2 , 4-triazolyl-3-one (0.30 g, 0.6 mmol) and triethylamine (0.07 g, 0.7 mmol) were dissolved in tetrahydrofuran (20 ml), and chloroisobutyl was added Rhenium (0.08 g, 0.7 mmol) was stirred at room temperature for 5 hours. Ice water was poured into the reaction solution, and ethyl acetate was extracted. Silica gel column chromatography [η-hexane-ethyl acetate (1 : 1)] The residue was purified to obtain 2 2,6-dichlorophenyl) -4- [2- (N-isopropylcarbonyltrifluoromethylsulfonamidobenzyl) b 2,4-dihydro-3Η -1,2,4-triazolyl-3, ketone (0.25 g, 72.7% recovery). Melting point is 55.6-61.9 ° C. (4-2). N- (2,6 —'Gasbenzene -N '-[2- (N-trifluoromethyl mineral acid-N-phenylcarbonyl) amine benzyl] -2-imidazolidinone N- (2,6-dichlorophenyl)- N,-(2-trifluoromethylsulfonamidobenzyl) -2-200404764 imidazolidone (0.30 g, 0.64 mmol) and triethylamine (0.07 g, 0.70 mmol) were dissolved In tetrahydrofuran (15 ml) and add benzamidine chloride (0.09 g, 0.64 mmol) After) was stirred for 7 hours at room temperature. Then, water was added to the purified ethyl acetate. Ethyl ester acetate layer was washed once with saturated brine, dried over anhydrous sodium sulfate and the solvent was distilled off. Purified by silica gel column chromatography 'to obtain N- (2,6-dichlorophenyl) _n,-[2- (N-trifluoromethylsulfonylphenylcarbonyl) amine benzylbenzene 2-imidazole Pyridone (0.09 g, 24.6% recovery). Melting point is 9 5-97 ° C.

本發明通式（I)係爲具有鹵烷磺醯苯胺衍生物或其鹽 類爲有效成分之除草劑，對例如：野稗（禾本科 1年生， 稻田害草）、鹼草（莎草科1年生草、稻田害草）、松葉藺（莎 草科多年生草、生長於濕地、水路、稻田，爲稻田的多年 生害草）、瓜皮草（野慈姑科，生長於稻田、濕地、水溝之 多年生害草）、野螢藺（莎草科多年生草，生長於稻田、師 弟、水溝）、看麥娘（禾本科二年生草，生長於稻田、低濕The general formula (I) of the present invention is a herbicide having a halosulfenilanilide derivative or a salt thereof as an active ingredient. For example, wild sedge (Gramineae 1-year-old, rice field pest), alkaline grass (Lyperiaceae) 1-year grass, rice field pests), pine leaf sedge (Perennial sedge family, growing in wetlands, waterways, paddy fields, perennial pests in rice fields), melon fur (Wild guidae, growing in rice fields, wetlands, water Gully perennial pests), wild firefly (cyperaceae perennial grass, growing in paddy field, younger brother, water ditch), see Mai Niang (Gramineous biennial grass, growing in rice field, low humidity

地）、燕麥草（禾本科二年生草，生長於平地、荒地、旱地卜 乂高（菊科多年生草，生長於山野、旱地）、馬唐（禾本科 年生早，旱地、樹園地的強害草）、羊蹄（蓼科多年生草 生長於旱地、道旁）、碎米莎草（莎草科丨年生草，旱地害 ^)、西風古（寬科i年生草，生長於空地 '道旁、旱地）、 蒼耳（菊科1年生草，旱地害草）、鳶尾（葵科丨年生草， 旱地害草）、白瑞香（茄科1年生草 婆納（玄參科1年生草，旱地害草） 生草，旱地、樹園地之害草）等稻田 旱地害草）、波斯婆 豬狹殃（茜草科二年 旱地、樹園地、濕 -98- 200404764 地等生長之1年生、二年生及多年生雜草，於除草方面係 爲有用的。特別是對雜草防除係爲有效的，相對於含有磺 醯脲系除草劑抵抗性雜草等難防除雜草之多數雜草種，具 有廣泛適用性、效果的持續性、廣泛稻田-水田雜草間選 擇性寬之水田用除草劑之優異性能。 本發明S式（I)係爲含有鹵烷磺醯苯胺衍生物或其鹽 類爲有效成分之除草劑，由其相對於發芽前及發芽後的雜 草顯示優異的除草效果，將有用的植物移植於預定地的預 先處理時、及有用的植物移植後（有用的植物包括即將從 樹園秧池中移植出來者）、從雜草的發生開始期到生育期 之處理而發現其生理活性的效果。然而本發明的除草劑關 於其態樣僅限於其使用，例如本發明除草劑係作爲水田用 除草劑使用，亦可作爲一般雜草的除草劑使用，如作爲收 割痕跡、休耕田地、田埂、農道、水渠、牧草造成地、墓 地、公園、道路、運動場、建築周圍空地、開墾地、線路 端、森林等一般雜草的驅除之目的使用。在這個時候，從 雜草發生開始期處理的話在經濟上最有效果，其非必要的 限制，亦可用防除生育期的雜草。 本發明通式（I)所表示的鹵烷磺醯苯胺衍生物或其鹽 類作爲除草劑使用時，於農藥製劑上的習知方法其作爲_ 般使用上都符合的良好形狀製劑而使用。換句話說，即本 發明通式（I)所表示的鹵烷磺醯苯胺衍生物或其鹽類係爲 適當的惰性載體，或其視需要地一起作爲輔助劑時，配合 適當比例溶解、分離、懸浮、混合、浸泡、吸附、適當的 -99- 200404764 劑形’例如懸浮劑、乳化懸浮劑、乳劑、水溶劑、水和劑、 粒劑、錠劑、巨型劑、包裝劑等製劑使用較佳。 本發明使用的惰性載體係爲固體或液體中任〜者均 可’由固體載體所得到的材料，例如：植物質粉末類（如 黃豆粉、穀物粉、木粉、樹皮粉、鋸粉 '蕃薯莖粉、核桃 穀粉、麥糠、纖維素粉末、植物萃取抽取物的殘渣等）、 粉碎合成樹脂等的合成聚合物、黏土類（如高嶺土、澎潤 土、酸性白土等）、滑石粉類（如滑石粉、葉臘石等）、二 氧化矽類{如矽藻土、矽砂、雲母、白碳黑（含水微粉矽素、 含水矽酸之合成高分散矽酸、包括由矽酸鈣爲主成分的製 品）}、活性炭、天然無機物質類（如玻璃粉末、輕石、燒 成矽藻土、石絨或沸石）燒成矽藻土、磚頭粉碎物、飛灰、 砂、塑膠載體等（如聚乙烯、聚丙烯、聚偏二氯乙烯等）、 碳酸鈣、磷酸鈣等無機礦物性粉末、硫胺、磷胺、硝胺尿 素、鹽胺等化學肥料、堆肥等。其可單獨或二種以上混合 物的類型使用。 體載體所得到之材料，其可選自括自體溶劑能、含有 溶劑能的輔助劑幫助之有效成分化合物分散所得者，例如 載體的代表例可爲下列單獨或二種以上混合物形通式使用 者，如··醇類（如甲醇、乙醇、異丙醇、丁醇、乙二醇等）、 酮類（如丙酮、甲基乙基酮、甲基異丁基酮、二異丁基酮、 環己酮等）、醚類（如***、二噚烷、溶纖劑、二丙醚、四 氫呋喃等）、脂肪族烴類（如煤油、礦物油等）、芳香族烴 類（如苯、甲苯、二甲苯、溶劑石腦油、烷基萘等）、鹵化 -100- 200404764 烴類（如二氯乙烷、氯仿、四氯化碳等）、酯類（如醋酸乙 酯、酞酸二異丁酯、酞酸二丁酯、酞酸二辛酯等）、醯胺 類（如二甲基甲醯胺、二乙基乙醯胺、二甲基乙醯胺）、腈 類（如乙腈等）、二甲亞碾等。 其次舉例其他代表的輔助劑，對應其使用輔助劑的目 的，可單獨或以二種以上的輔助劑合倂使用，或可完全不 使用輔助劑。有效成分化合物的乳化、分散、可融化及/ 或濕潤的目的而使用的界面活性劑可爲，例如：聚環氧乙 烷烷基醚、聚環氧乙烷烷芳基醚、聚環氧乙烷高級脂肪酸 酯、聚環氧乙院樹脂酸酯、聚環氧乙院山梨糖醇酐單月桂 酸酯、聚環氧乙烷山梨糖醇酐單油酸酯、烷芳基磺酸鹽、 萘磺酸縮合物、木質磺酸縮合物、高級醇硫酸酯等界面活 性劑。 再者’爲了有效成分化合物的分散安定化、黏著及/ 或鍵結的目的，其次係舉例所使用的輔助劑，可使用例如： 酪蛋白、明膠、澱粉、甲基纖維素、羥甲基纖維素、阿拉 伯樹脂、聚乙烯醇、松根油、糠油、膨潤土、木質磺酸鹽 #。爲了固體製品流動性的改良而使用的輔助劑，可使用 例如：臘、硬脂酸鹽、磷酸烷基酯等輔助劑。懸浮性製品 的去絮凝劑’可使用例如：萘磺酸縮合物、縮合隣酸鹽等 輔助劑。消泡劑可使用例如：矽油等輔助劑。 有效成分的配合比例可視需要地增減，並無特別地限 制’大槪爲下限0 · 0 0 1重量％〜上限9 0重量％。例如爲粉 劑或粒劑時的下限爲0.0 1重量％爲佳、較佳爲o.i重量 200404764 %，上限爲50重量％爲佳、較佳爲ι〇重量％。若爲乳劑、 水合劑或顆粒水合劑時的下限較佳爲〇 . 〇 1重量％、更佳 爲0.1重量％，上限較佳爲90重量％、更佳爲60重量％。 含有本發明通式（I)所表示的鹵烷磺醯苯胺衍生物或其鹽 類作爲有效成分之除草劑，不稀釋即可枯死各種雜草或者 抑制其生長、或用水適當地稀釋，或者以懸浮類型除草或 以對該雜草的生長抑制有效量、或當該雜草發生時或成長 發育不佳時適合使用於莖葉或土壤。 含有本發明通式（I)所表示的鹵烷磺醯苯胺衍生物或 其鹽類爲有效成分之除草劑的使用量，其係根據各種因 子’例如··對象雜草、作物的生長狀況、雜草的發生傾向、 天候、環境條件、劑型、施用方法、施用場所、使用時期 等而變動，有效成分化合物平均1公頃爲0.1克〜10公斤 的範圍爲佳，其係根據目的做適當的選擇。含有本發明通 式（I)所表示的鹵烷磺醯苯胺衍生物或其鹽類爲有效成分 之除草劑，進一步爲了擴大防除對象雜草、防除時期、或 減低藥量的目的，可混合其他除草劑使用。 以下係表示代表本發明的製劑例及試驗例，然本發明 不受其限制。而且，製劑例中份係爲重量份。 製劑例1 本發明化合物 10份 二甲苯 70份 N-甲基吡咯啶酮 10份 -102- 200404764 聚環氧乙烷壬苯基醚與 烷基苯磺酸鈣的混合物 將上述均勻混合溶解之乳劑。 1 〇份 製劑例2 本發明化合物 3份 灰色粉末 82份 砍藻土粉末 將上述均均混合粉碎之粉劑。 1 5份 製劑例3 本發明混合物 5份 膨潤土與灰土的混合粉末 90份 木質磺酸鈣 5份 將上述均勻混合、添加適量的水捏合、造粒、乾燥之 粒劑。 籲 製劑例4 本發明化合物 2 0份 高嶺土與合成高分散矽酸 75份 聚環氧乙烷壬苯基醚與 烷基苯磺酸鈣的混合物 5份 將上述均勻混合粉碎之水合劑。 -103- 200404764 試驗例1對發芽前水田雜草的除草效果試驗 在75平方公分的塑膠壺中塡充土壤（栽植土），撥種 水田雜草的野稗、野螢藺的種子，且於混合見風紅 (Lindernia pyxidaria All·)的種子之混合土壤75平方公分 覆土後’充水至水深5公分的狀態，在溫室內育成。隔天， 按照製劑例1〜4以本發明化合物（第1表至第1 3表所記載 的化合物）爲有效成分調製，用水稀釋藥劑所定之有效藥 量，於水面滴下處理。就溫室內育成、處理2 1天後除草 效果進行調查，與沒有處理做比較，從下列的基準來評估 除草效果。 除草效果（生長發育抑制程度）及藥害的判定基準。 4 ··· 9 0 %〜1 0 0 %的除草效果、藥害 3 ··· 70%〜89%的除草效果、藥害 2 ··· 4 0 %〜6 9 %的除草效果、藥害 1 ··· 1 %〜3 9 %的除草效果、藥害 0 · · · 0%的除草效果、藥害 結果如第1 5表所示。 再者，表中的「/」表示實驗未實施。 -104- 200404764 第1 5表 藥量(克/公頃）野稗 野螢藺 見風不工 1-2 1000 / 4 1-8 1000 / 4 1-23 1000 / 4 1-27 1000 ./ 4 1-28 1000 / 4 1-29 1000 / 4 1-30 1000 0 4 1-32 1000 / 4 1-36 1000 / 4 1-38 1000 / 4 1-40 1000 / 4 1-41 1000 / 4 1-43 1000 / 4 1-44 1000 / 4 1-47 1000 / 4 1-50 1000 / 4 1-59 1000 / 4 1-81 1000 / 4 1-84 1000 / 4 1-88 1000 / 4 1-89 1000 / 4 1-90 1000 / 4 1-91 1000 / 4 1-92 1000 / 4 1-93 1000 / 4 1-94 1000 / 4 1-95 1000 / 4 1-102 1000 / 4 1-103 1000 / 4 1-107 1000 / 4 1-108 1000 / 4 1-112 1000 / 4 1-123 1000 / 4 1-124 1000 / 4 1-165 1000 / 4 1-177 1000 / 4 1-183 1000 / 4 10444444444444444444444444444444/4440Ground), oat grass (Gramineous biennial grass, grows on flat land, wasteland, dry land) (Erythropoaceae perennial grass, grows in the wild, dry land), Matang (grassland early in the year, dry land, tree garden) ), Sheep's hoof (Perennial grass growing on dry land, roadside), Fragaria sedge (Cyperaceae 丨 annual grass, dry land damage ^), Xifenggu (wide family i-year grass, growing on open land 'roadside, dry land ), Cocklebur (1-year-old grass in Asteraceae, dry grass pests), Iris (Anemone 丨 annual grass, dry-land pests), Bai Ruixiang (1-year-old grass in Solanaceae Poona (Xuansheng Family 1-year grass, dry-land pests) ) Grass, dry land, plant garden pests) and other paddy field dry grass pests), Persian pig pigs narrow (Barnaceae two-year dry land, tree garden land, wet-98-200404764 land, etc. growing in biennial, biennial, and perennial hybrids Grass is useful for weed control. It is especially effective for weed control systems. Compared with most weed species that are difficult to control weeds such as sulfonylurea herbicide-resistant weeds, it has a wide applicability, Persistence of effect, wide paddy field-paddy field weed Excellent performance of wide-selective herbicides for paddy fields. The S formula (I) of the present invention is a herbicide containing a halosulfanilanilide derivative or a salt thereof as an active ingredient, compared with before and after germination. Weeds show excellent weed control effects, useful plants are transplanted in the pre-planned area, and useful plants are transplanted (useful plants include those who are about to be transplanted from tree garden seedling ponds), and weeds occur The physiological effect of the herbicide of the present invention is only limited to its use, for example, the herbicide of the present invention is used as a paddy field herbicide, and can also be used as a general weed. Herbicide use, such as for the removal of general weeds such as harvest marks, fallow fields, fields, agricultural roads, canals, pastures, graveyards, parks, roads, sports fields, open spaces around buildings, reclamations, line ends, forests, etc. At this time, treatment from the beginning of weed occurrence is the most economically effective, and its unnecessary restrictions can also be used to control the growth of weeds. When the halosulfanilanilide derivative represented by the general formula (I) of the present invention or a salt thereof is used as a herbicide, a conventional method for pesticide preparations is used as a well-formed preparation that conforms to general use. In other words, when the halosulfanilanilide derivative represented by the general formula (I) of the present invention or a salt thereof is a suitable inert carrier, or when used together as an adjuvant as necessary, it is dissolved in an appropriate proportion, Separation, suspension, mixing, soaking, adsorption, appropriate -99-200404764 dosage forms such as suspensions, emulsifying suspensions, emulsions, water solvents, water and agents, granules, lozenges, giants, packaging agents and other preparations Preferably, the inert carrier used in the present invention is any one of solid or liquid. The material obtained from the solid carrier is, for example, plant-based powders (such as soybean powder, cereal powder, wood powder, bark powder, sawn Powder, sweet potato stalk powder, walnut cereal powder, wheat bran, cellulose powder, residues of plant extracts, etc.), synthetic polymers such as crushed synthetic resins, clays (such as kaolin, pennite, acid white clay, etc. ), Talc (such as talc, pyrophyllite, etc.), silicon dioxide {such as diatomaceous earth, silica sand, mica, white carbon black (aqueous micronized silicon, hydrous silicic acid, highly dispersed silicic acid, Including products based on calcium silicate)}, activated carbon, natural inorganic substances (such as glass powder, pumice, fired diatomaceous earth, stone wool or zeolite) fired diatomaceous earth, crushed bricks, fly ash , Sand, plastic carrier (such as polyethylene, polypropylene, polyvinylidene chloride, etc.), inorganic mineral powders such as calcium carbonate, calcium phosphate, chemical fertilizers such as thiamine, phosphorus amine, nitrosamine urea, and salt amine, compost Wait. It can be used alone or as a mixture of two or more types. The material obtained from the bulk carrier can be selected from the dispersion of active ingredient compounds including autosolvent and solvent-containing adjuvants. For example, the representative examples of the carrier can be used alone or in the form of two or more mixtures. Such as alcohols (such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and diisobutyl ketone) , Cyclohexanone, etc.), ethers (such as diethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (such as kerosene, mineral oil, etc.), aromatic hydrocarbons (such as benzene, Toluene, xylene, solvent naphtha, alkyl naphthalene, etc.), halogenated -100-200404764 hydrocarbons (such as dichloroethane, chloroform, carbon tetrachloride, etc.), esters (such as ethyl acetate, phthalic acid di Isobutyl ester, dibutyl phthalate, dioctyl phthalate, etc.), amidines (such as dimethylformamide, diethylacetamide, dimethylacetamide), nitriles (such as acetonitrile Etc.), Dijia Yalian, etc. The other examples of auxiliary agents are given below. According to the purpose of using the auxiliary agents, they can be used alone or in combination of two or more auxiliary agents, or they can be used completely. The surfactant used for the purpose of emulsifying, dispersing, melting and / or moistening the active ingredient compound may be, for example, polyethylene oxide alkyl ether, polyethylene oxide aryl ether, polyethylene oxide Higher fatty acid esters, polyethylene oxide resin esters, polyethylene oxide sorbitan monolaurate, polyethylene oxide sorbitan monooleate, alkylaryl sulfonates, Surfactants such as naphthalenesulfonic acid condensate, lignosulfonic acid condensate, higher alcohol sulfate. Furthermore, for the purpose of stabilizing, adhering, and / or bonding of the active ingredient compounds, the auxiliary agents used in the following examples are used, for example, casein, gelatin, starch, methylcellulose, and hydroxymethyl fiber. Vegetarian, arabic resin, polyvinyl alcohol, pine root oil, bran oil, bentonite, lignosulfonate #. As the adjuvant used for improving the fluidity of a solid product, for example, an adjuvant such as wax, stearate, alkyl phosphate and the like can be used. As the deflocculant for the suspension product, an adjuvant such as a naphthalenesulfonic acid condensate, or a condensed o-acid salt can be used. As the defoaming agent, auxiliary agents such as silicone oil can be used. The blending ratio of the active ingredient may be increased or decreased as necessary, and there is no particular limitation on the 'large' being a lower limit of 0. 0 0 1% to an upper limit of 90% by weight. For example, in the case of powder or granules, the lower limit is preferably 0.01% by weight, preferably o.i. weight is 200404764%, and the upper limit is preferably 50% by weight, preferably ι0% by weight. In the case of an emulsion, a hydrating agent or a granular hydrating agent, the lower limit is preferably 0.01% by weight, more preferably 0.1% by weight, and the upper limit is preferably 90% by weight, and more preferably 60% by weight. A herbicide containing the halosulfenilanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient, which can die off various weeds or inhibit their growth without dilution, or appropriately dilute with water, or Suspension type weeding is suitable for use on stems, leaves, or soil when the weeds are growth-inhibiting effective amount, or when the weeds occur or the growth is poor. The amount of the herbicide containing the halosulfanilanilide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is based on various factors such as the target weed, the growth status of the crop, The occurrence tendency of weeds, weather, environmental conditions, dosage forms, application methods, application sites, use periods, etc. vary, and the effective ingredient compound is preferably in the range of 0.1 g to 10 kg per hectare, and it is appropriately selected according to the purpose. . Herbicides containing the halosulfenanilide derivatives represented by the general formula (I) of the present invention or salts thereof as an active ingredient, and may further be mixed for the purpose of expanding the target weed control, the control period, or reducing the amount of the herb. Herbicide use. The following are formulation examples and test examples representing the present invention, but the present invention is not limited thereto. The parts in the formulation examples are parts by weight. Formulation Example 1 10 parts of the compound of the present invention, xylene, 70 parts of N-methylpyrrolidone, 10 parts of -102- 200404764, a mixture of polyethylene oxide nonphenyl ether and calcium alkylbenzene sulfonate, and an emulsion prepared by uniformly mixing and dissolving the above . 10 parts Formulation Example 2 Compound of the present invention 3 parts Gray powder 82 parts Chlorella powder All of the above were mixed and pulverized. 15 parts Formulation example 3 5 parts of the mixture of the present invention 5 parts of mixed powder of bentonite and lime earth 90 parts of calcium lignosulfonate 5 parts The above were uniformly mixed, and an appropriate amount of water was kneaded, granulated, and dried granules. Formulation Example 4 20 parts of the compound of the present invention, kaolin clay and 75 parts of synthetic high-dispersion silicic acid, 5 parts of a mixture of polyethylene oxide nonphenyl ether and calcium alkylbenzenesulfonate, 5 parts. -103- 200404764 Test example 1 Test of weeding effect on paddy field weeds before germination. Fill a soil (planting soil) in a 75 cm square plastic pot, and plant seeds of wild paddy and wild firefly in the paddy field. The mixed soil of the seed of Winder Red (Lindernia pyxidaria All ·) was covered with 75 square centimeters of soil, and was' filled with water to a depth of 5 centimeters, and was grown in a greenhouse. The following day, according to Formulation Examples 1 to 4, the compound of the present invention (the compounds described in Tables 1 to 13) was prepared as an active ingredient, and the effective dose determined by the drug was diluted with water, and the solution was dropped on the water surface. The weeding effect after 21 days of incubation and treatment in the greenhouse was investigated, and compared with no treatment, the weeding effect was evaluated from the following criteria. Criteria for judging herbicidal effects (degree of growth and development inhibition) and phytotoxicity. 4 ... 90% ~ 100% herbicidal effect, phytotoxicity 3 ... 70% ~ 89% herbicidal effect, phytotoxicity 2 ... 40% ~ 69% herbicidal effect, phytotoxicity 1 ··· 1% ~ 39% of the herbicidal effects and pesticide damage 0 · · · 0% of the herbicidal effects and pesticide damage results are shown in Table 15. The "/" in the table indicates that the experiment was not performed. -104- 200404764 Table 1 5 Dosage (g / ha) Nori Noguchi seeing wind does not work 1-2 1000/4 1-8 1000/4 1-23 1000/4 1-27 1000 ./ 4 1 -28 1000/4 1-29 1000/4 1-30 1000 0 4 1-32 1000/4 1-36 1000/4 1-38 1000/4 1-40 1000/4 1-41 1000/4 1-43 1000/4 1-44 1000/4 1-47 1000/4 1-50 1000/4 1-59 1000/4 1-81 1000/4 1-84 1000/4 1-88 1000/4 1-89 1000 / 4 1-90 1000/4 1-91 1000/4 1-92 1000/4 1-93 1000/4 1-94 1000/4 1-95 1000/4 1-102 1000/4 1-103 1000/4 1 -107 1000/4 1-108 1000/4 1-112 1000/4 1-123 1000/4 1-124 1000/4 1-165 1000/4 1-177 1000/4 1-183 1000/4 10444444444444444444444444444444444/4440

-105- 200404764 第1 5表（續） 藥量(克/公頃)野稗 野螢藺 見風紅 1-189 1000 丨 1-190 1000 / 1-192 1000 4 1-193 1000 / 1-198 1000 / 1-199 1000 / 1-215 1000 4 1-237 1000 / 1-245 1000 / 1-251 1000 / 1-254 1000 / 1-257 1000 / 1-258 1000 / 1-265 1000 4 1-266 1000 / 1-268 1000 / 1-273 1000 / 1-279 1000 / 1-282 1000 / 1-285 1000 / 1-286 1000 / 1-288 1000 / 1-291 1000 / 1-292 1000 / 1-323 1000 / 1-324 1000 / 1-325 1000 / 1-326 1000 / 1-327 1000 / 1-328 1000 / 2-8 1000 / 2-9 1000 / 2-12 1000 / 2-23 1000 4 2-24 1000 / 2-27 1000 4 2-28 1000 3 2-29 1000 4 444444442444444444444/44024444/4444444 //444/444444444444444/44 3 444.4/4444444 -106- 200404764 第1 5表（續)-105- 200404764 Table 15 (continued) Dosage (g / ha) Nogino Nori Nogami see Fenghong 1-189 1000 丨 1-190 1000 / 1-192 1000 4 1-193 1000 / 1-198 1000 / 1-199 1000 / 1-215 1000 4 1-237 1000 / 1-245 1000 / 1-251 1000 / 1-254 1000 / 1-257 1000 / 1-258 1000 / 1-265 1000 4 1-266 1000 / 1-268 1000 / 1-273 1000 / 1-279 1000 / 1-282 1000 / 1-285 1000 / 1-286 1000 / 1-288 1000 / 1-291 1000 / 1-292 1000 / 1-323 1000 / 1-324 1000 / 1-325 1000 / 1-326 1000 / 1-327 1000 / 1-328 1000 / 2-8 1000 / 2-9 1000 / 2-12 1000 / 2-23 1000 4 2-24 1000 / 2-27 1000 4 2-28 1000 3 2-29 1000 4 444444442444444444444/44024444/4444444 // 444/444444444444444/44 3 444.4 / 4444444 -106- 200404764 Table 15 (continued)

藥量(克/公頃） 野稗 野螢藺 見風紅 2-30 1000 / 4 4 2-36 1000 / 4 4 2-37 1000 / 4 4 2-38 1000 / 4 4 2-41 1000 / 4 4 2-43 1000 / 4 4 2-51 1000 / 4 4 2-60 1000 / / / 2-61 1000 / 4 4 2-63 1000 / 4 / 2-64 1000 / 4 4 2-65 1000 / 4 4 2-66 1000 4 4 4 2-67 1000 / 4 4 2-68 1000 / 4 4 2-69 1000 / 1 4 2-70 1000 / 4 / 2-71 1000 / 4 4 2-72 1000 / 4 4 2-73 1000 / 4 4 2-76 1000 / 4 4 2-79 1000 / 2 4 2-81 1000 / 4 4 2-82 1000 / 4 7 2-83 1000 / 4 4 2-85 1000 / 4 4 2-86 1000 / 4 4 2-87 1000 / 4 4 2-88 1000 / 4 / 2-92 1000 / / / 2-93 1000 / 4 / 2-94 1000 / 4 4 2-98 1000 / 4 0 2-130 1000 1 4 4 2-167 1000 / 4 / 2-169 1000 0 4 4 2-176 1000 4 4 4 2-177 1000 / 4 4 -107- 200404764 第1 5表（續） 藥量(克/公頃）野稗 野螢藺 紅 風 見 2-184 1000 / 2-185 1000 / 2-186 1000 / 2-205 1000 / 2-209 1000 4 2-221 1000 4 2-227 1000 2 2-244 1000 / 2-245 1000 / 2-246 1000 / 2-247 1000 / 3-2 1000 / 3-3 1000 / 3-4 1000 / 3-5 1000 / 3-6 1000 / 3-8 1000 / 3-13 1000 / 3-18 1000 / 3-19 1000 / 3-22 1000 4 3-23 1000 / 3-24 1000 / 3-25 1000 / 3-29 1000 / 3-32 1000 / 3-36 1000 / 3-37 1000 / 3-38 1000 / 3-46 1000 / 3-47 1000 / 3-48 1000 / 3-49 1000 / 3-53 1000 / 3-61 1000 / 3-79 1000 / 3-80 1000 / 3-83 1000 / 444/4444144444444444444444444444/4/34/ 444/44/444444444444444444444444444444 -108- 200404764 第1 5表（續） 藥量(克/公頃）野稗 野螢藺 見風紅 3-156 1000 / 3-157 1000 / 3-158 1000 / 3-159 1000 / 3-160 1000 / 3-161 1000 / 3-162 1000 / 3-163 1000 / 3-164 1000 / 3-165 1000 / 3-166 1000 / 3-167 1000 / 3-168 1000 / 3-169 1000 / 3-170 1000 / 3-171 1000 / 3-172 1000 / 3-173 1000 / 3-174 1000 / 3-175 1000 / 3-176 1000 / 3-177 1000 / 3-178 1000 / 3-179 1000 / 3-180 1000 / 3-181 1000 / 3-182 1000 / 3-183 1000 / 3-184 1000 / 3-185 1000 / 4-14 1000 4 4-39 1000 / 5-6 1000 / 5-29 1000 / 5-50 1000 / 5-64 1000 / 5-93 1000 / 6-8 1000 / 4/4444444 .—-42/4^—-/04344442244414444434/4 4/4//4444244/40/04444444444444444124/4Dosage (g / ha) Nori Noguchi seeing red 2-30 1000/4 4 2-36 1000/4 4 2-37 1000/4 4 2-38 1000/4 4 2-41 1000/4 4 2-43 1000/4 4 2-51 1000/4 4 2-60 1000 // // 2-61 1000/4 4 2-63 1000/4 / 2-64 1000/4 4 2-65 1000/4 4 2 -66 1000 4 4 4 2-67 1000/4 4 2-68 1000/4 4 2-69 1000/1 4 2-70 1000/4 / 2-71 1000/4 4 2-72 1000/4 4 2- 73 1000/4 4 2-76 1000/4 4 2-79 1000/2 4 2-81 1000/4 4 2-82 1000/4 7 2-83 1000/4 4 2-85 1000/4 4 2-86 1000/4 4 2-87 1000/4 4 2-88 1000/4 / 2-92 1000 / / / 2-93 1000/4 / 2-94 1000/4 4 2-98 1000/4 0 2-130 1000 1 4 4 2-167 1000/4 / 2-169 1000 0 4 4 2-176 1000 4 4 4 2-177 1000/4 4 -107- 200404764 Table 15 (continued) Dose (g / ha) Field Takino Hotaru Red Wind See 2-184 1000 / 2-185 1000 / 2-186 1000 / 2-205 1000 / 2-209 1000 4 2-221 1000 4 2-227 1000 2 2-244 1000 / 2-245 1000 / 2-246 1000 / 2-247 1000 / 3-2 1000 / 3-3 1000 / 3-4 1000 / 3-5 1000 / 3-6 1000 / 3-8 1000 / 3-13 1000 / 3-18 1000 / 3-19 1000 / 3-22 1000 4 3-23 1000 / 3-24 1000 / 3-25 1000 / 3-29 1000 / 3-32 1000 / 3-36 1000 / 3-37 1000 / 3-38 1000 / 3-46 1000 / 3-47 1000 / 3-48 1000 / 3-49 1000 / 3-53 1000 / 3-61 1000 / 3-79 1000 / 3-80 1000 / 3-83 1000/444/4444144444444444444444444444444/4/34 / 444/44/444444444444444444444444444444444 -108- 200404764 Table 15 (Continued) / 3-157 1000 / 3-158 1000 / 3-159 1000 / 3-160 1000 / 3-161 1000 / 3-162 1000 / 3-163 1000 / 3-164 1000 / 3-165 1000 / 3-166 1000 / 3-167 1000 / 3-168 1000 / 3-169 1000 / 3-170 1000 / 3-171 1000 / 3-172 1000 / 3-173 1000 / 3-174 1000 / 3-175 1000 / 3-176 1000 / 3-177 1000 / 3-178 1000 / 3-179 1000 / 3-180 1000 / 3-181 1000 / 3-182 1000 / 3-183 1000 / 3-184 1000 / 3-185 1000 / 4-14 1000 4 4-39 1000 / 5-6 1000 / 5-29 1000 / 5-50 1000 / 5-64 1000 / 5-93 1000 / 6-8 1000 / 4/4444444 .--- 42/4 ^ --- / 04344442244414 444434/4 4/4 // 4444244/40/04444444444444444444124/4

-109- 200404764 第1 5表（續） 藥量(克/公頃）野稗 野螢藺 見風紅 6-9 1000 / 6-10 1000 / 6-19 1000 / 6-27 1000 / 6-28 1000 / 6-29 1000 / 6-32 1000 / 6-33 1000 / 6-60 1000 4 6 - 62 1000 / 6-73 1000 / 6-82 1000 / 6-83 1000 / 6-113 1000 4 6-339 1000 / 6-340 1000 / 6-341 1000 / 6-342 1000 / 6-343 1000 / 6-344 1000 / 6-345 1000 / 6-346 1000 / 6-347 1000 / 6-348 1000 / 6-349 1000 / 6-350 1000 / 6-351 1000 / 6-352 1000 / 6-353 1000 / 6-354 1000 / 6-355 1000 / 6-356 1000 / 6-357 1000 / 6-358 1000 / 6-359 1000 / 6-360 1000 / 6-361 1000 / 6-362 1000 / 4444444444444444444444/4444444444444// 4444444444444444444444/4444444444444//-109- 200404764 Table 15 (continued) Dosage (g / ha) Nori Noguchi sees red 6-9 1000 / 6-10 1000 / 6-19 1000 / 6-27 1000 / 6-28 1000 / 6-29 1000 / 6-32 1000 / 6-33 1000 / 6-60 1000 4 6-62 1000 / 6-73 1000 / 6-82 1000 / 6-83 1000 / 6-113 1000 4 6-339 1000 / 6-340 1000 / 6-341 1000 / 6-342 1000 / 6-343 1000 / 6-344 1000 / 6-345 1000 / 6-346 1000 / 6-347 1000 / 6-348 1000 / 6-349 1000 / 6-350 1000 / 6-351 1000 / 6-352 1000 / 6-353 1000 / 6-354 1000 / 6-355 1000 / 6-356 1000 / 6-357 1000 / 6-358 1000 / 6-359 1000 / 6-360 1000 / 6-361 1000 / 6-362 1000/4444444444444444444444/4444444444444 // 4444444444444444444444/4444444444444 //

-110- 200404764 第1 5表（續） 藥量(克/公頃) 6-363 1000 6-364 1000 6-365 1000 6-366 1000 6-367 1000 6-368 1000 6-369 1000 6-370 1000 6-371 1000 6-372 1000 6-373 1000 6-374 1000 6-375 1000 6-376 1000 6-377 1000 6-378 1000 6-379 1000 6-380 1000 6-381 1000 6-382 1000 6-383 1000 7-60 1000 7-217 1000 8-56 1000 9-56 1000 10-1 1000 10-2 1000 10-8 1000 10-12 1000 10-13 1000 10-14 1000 10-15 1000 10-16 1000 10-17 1000 10-18 1000 10-19 1000 10-20 1000 10-21 1000-110- 200404764 Table 15 (continued) Dose (g / ha) 6-363 1000 6-364 1000 6-365 1000 6-366 1000 6-367 1000 6-368 1000 6-369 1000 6-370 1000 6-371 1000 6-372 1000 6-373 1000 6-374 1000 6-375 1000 6-376 1000 6-377 1000 6-378 1000 6-379 1000 6-380 1000 6-381 1000 6-382 1000 6- 383 1000 7-60 1000 7-217 1000 8-56 1000 9-56 1000 10-1 1000 10-2 1000 10-8 1000 10-12 1000 10-13 1000 10-14 1000 10-15 1000 10-16 1000 10-17 1000 10-18 1000 10-19 1000 10-20 1000 10-21 1000

野螢藺 紅風見 //////////////////444443/444444444444 0 4 2 4 4 444444444444 200404764 第1 5表（續) 藥量(克/公頃） 野稗 野螢藺 見風紅 10-23 1000 / 4 / 10-24 1000 / 4 4 10-26 1000 / 4 / 10-28 1000 / 4 / 10-29 1000 / 4 4 10-34 1000 / 4 4 10-35 1000 / 4 4 10-37 1000 0 4 4 10-39 1000 / 4 4 10-40 1000 / 4 4 10 - 58 1000 / / / 10-59 1000 / / / 10-116 1000 / 4 4 11-7 1000 4 4 4 11-11 1000 / 4 4 11-23 1000 / 4 4 12-1 1000 / 4 4 12-4 1000 4 4 4 12-7 1000 4 4 4Wild firefly red wind sees ////////////////// 444443/444444444444 0 4 2 4 4 444444444444 200404764 Table 15 (continued) Dose (g / ha) Hotaru Saki sees red 10-23 1000/4 / 10-24 1000/4 4 10-26 1000/4 / 10-28 1000/4 / 10-29 1000/4 4 10-34 1000/4 4 10-35 1000/4 4 10-37 1000 0 4 4 10-39 1000/4 4 10-40 1000/4 4 10-58 1000 // // 10-59 1000 // // 10-116 1000/4 4 11-7 1000 4 4 4 11-11 1000/4 4 11-23 1000/4 4 12-1 1000/4 4 12-4 1000 4 4 4 12-7 1000 4 4 4

[0131] 試驗例2 對發芽後水田雜草的除草效果試驗 在75平方公分的塑膠壺中塡充土壤（栽植土），撥種水 田雜草的野稗、野螢藺的種子，且於混合見風紅的種子之 混合土壤7 5平方公分覆土後，充水至水深5公分的狀態， 在溫室內育成。供試驗的植物於一個葉期的時間內，以本 發明化合物（第1表至第13表所記載的化合物）爲有效成分 ，處理所定有效藥量（g/ha)藥液之藥劑。接者就在溫室內 育成、處理2 1天後除草效果進行調查，與沒有處理做比較 ，從試驗例1的基準來評估除草效果。結果如第1 6表所示 -112- 200404764 第1 6表 藥量(克/公頃) 稗野 R3 野螢藺 1-2 1000 1-8 1000 1-23 1000 1-27 1000 1-28 1000 1-29 1000 1-30 1000 1-32 1000 1-36 1000 1-38 1000 1-40 1000 1-41 1000 1-43 1000 1-44 1000 1-47 1000 1-50 1000 1-59 1000 1-81 1000 1-84 1000 1-88 1000 1-89 1000 1-90 1000 1-91 1000 1-92 1000 1-93 1000 1-94 1000 1-95 1000 1-102 1000 1-103 1000 1-107 1000 1-108 1000 1-112 1000 1-123 1000 1-124 1000 1-165 1000 1-177 1000 1-183 1000 1-189 1000 4344144444443444404441/444442441/42344 4444444444444444444444/44444444444444/ 見風紅 """2 4 4 4 4 4 4 4 4 4 4Test Example 2 Test of Weeding Effect on Weeds in Paddy Fields after Germination The soil (planting soil) was filled in 75 cm 2 plastic pots, and the seeds of wild pupae and wild firefly in the paddy field were planted and mixed. After seeing the red mixed soil of 75 cm2, the soil was filled with water to a depth of 5 cm, and it was grown in a greenhouse. The plants to be tested used the compound of the present invention (compounds described in Tables 1 to 13) as an active ingredient within one leaf stage to treat a drug with a predetermined effective drug amount (g / ha). They then investigated the weeding effect after 21 days of incubation and treatment in the greenhouse, and compared it with no treatment, and evaluated the weeding effect from the benchmark of Test Example 1. The results are shown in Table 16 -112- 200404764 Table 16 Dose (g / ha) Takino R3 Takino 1-2 1000 1-8 1000 1-23 1000 1-27 1000 1-28 1000 1 -29 1000 1-30 1000 1-32 1000 1-36 1000 1-38 1000 1-40 1000 1-41 1000 1-43 1000 1-44 1000 1-47 1000 1-50 1000 1-59 1000 1-81 1000 1-84 1000 1-88 1000 1-89 1000 1-90 1000 1-91 1000 1-92 1000 1-93 1000 1-94 1000 1-95 1000 1-102 1000 1-103 1000 1-107 1000 1 -108 1000 1-112 1000 1-123 1000 1-124 1000 1-165 1000 1-177 1000 1-183 1000 1-189 1000 4344144444443444404441/444442441/42344 4444444444444444444444/44444444444444 / See Fenghong " " 2 4 4 4 4 4 4 4 4 4 4 4

4 4 4 4 4 4 4 4 4 4 4 4 4 4 44 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4

4 4 4 / 4 4 4 4 4 -113- 200404764 第1 6表（續） 藥量(克/公頃) 野螢藺 見風紅 1-190 1000 1-192 1000 1-193 1000 1-198 1000 1-199 1000 1-215 1000 1-237 1000 1-245 1000 1-251 1000 1-254 1000 1-257 1000 1-258 1000 1-265 1000 1-266 1000 1-268 1000 1-273 1000 1-279 1000 1-282 1000 1-285 1000 1-286 1000 1-288 1000 1-291 1000 1-292 1000 1-323 1000 1-324 1000 1-325 1000 1-326 1000 1-327 1000 1-328 1000 2-8 1000 2-9 1000 2-12 1000 2-23 1000 2-24 1000 2-27 1000 2-28 1000 2-29 1000 2-30 1000 4 4 44340444/44320002/210012241/0444124 4444444444444444444//440044444444 44444 4444444344/444443424/443444/44444444444 4 4/4 4 4 4 -113- 200404764 Table 16 (continued) Dosage (g / hectare) Nori Hotakami sees red 1-190 1000 1-192 1000 1-193 1000 1-198 1000 1 -199 1000 1-215 1000 1-237 1000 1-245 1000 1-251 1000 1-254 1000 1-257 1000 1-258 1000 1-265 1000 1-266 1000 1-268 1000 1-273 1000 1-279 1000 1-282 1000 1-285 1000 1-286 1000 1-288 1000 1-291 1000 1-292 1000 1-323 1000 1-324 1000 1-325 1000 1-326 1000 1-327 1000 1-328 1000 2 -8 1000 2-9 1000 2-12 1000 2-23 1000 2-24 1000 2-27 1000 2-28 1000 2-29 1000 2-30 1000 4 4 44340444/44320002/210012241/0444124 4444444444444444444 // 440044444444 44444 4444444344 / 444443424/443444/4444444444

-114- 200404764 第1 6表（續） 藥量(克/公頃) 稗野 03 野螢藺 見風紅 2-36 1000 2-37 1000 2-38 1000 2-41 1000 2-43 1000 2-51 1000 2-60 1000 2-61 1000 2-63 1000 2-64 1000 2-65 1000 2-66 1000 2-67 1000 2-68 1000 2-69 1000 2-70 1000 2-71 1000 2-72 1000 2-73 1000 2-76 1000 2-79 1000 2-81 1000 2-82 1000 2-83 1000 2-85 1000 2-86 1000 2-87 1000 2-88 1000 2-92 1000 2-93 1000 2-94 1000 2-98 1000 2-130 1000 2-167 1000 2-169 1000 2-176 1000 2-177 1000 2-184 1000 424243104/44241440440310434 4 4 4 444444/444444424444444444444/444444444 444444/4//44444444/444/4444///424/4444-114- 200404764 Table 16 (continued) Dose (g / ha) Takino 03 Takino Misaki sees red 2-36 1000 2-37 1000 2-38 1000 2-41 1000 2-43 1000 2-51 1000 2-60 1000 2-61 1000 2-63 1000 2-64 1000 2-65 1000 2-66 1000 2-67 1000 2-68 1000 2-69 1000 2-70 1000 2-71 1000 2-72 1000 2 -73 1000 2-76 1000 2-79 1000 2-81 1000 2-82 1000 2-83 1000 2-85 1000 2-86 1000 2-87 1000 2-88 1000 2-92 1000 2-93 1000 2-94 1000 2-98 1000 2-130 1000 2-167 1000 2-169 1000 2-176 1000 2-177 1000 2-184 1000 424243104/44241440440310434 4 4 4 444444/444444424444444444444/444444444 444444/4/44444444/444/4444 /// 424/4444

-115- 200404764 第1 6表（續） 藥量(克/公頃) 稗野 R3 野螢藺 2-185 1000 2-186 1000 2-205 1000 2-209 1000 2-221 1000 2-227 1000 2-244 1000 2-245 1000 2-246 1000 2-247 1000 3-2 1000 3-3 1000 3-4 1000 3-5 1000 3-6 1000 3-8 1000 3-13 1000 3-18 1000 3-19 1000 3-22 1000 3-23 1000 3-24 1000 3-25 1000 3-29 1000 3-32 1000 3-36 1000 3-37 1000 3-38 1000 3-46 1000 3-47 1000 3-48 1000 3-49 1000 3-53 1000 3-61 1000 3-79 1000 3-80 1000 3-83 1000 3-156 1000 4/1412 2/422003244401342 1241104002 4 44/444/0444444444444//444444444//4 3 4/ 4 44/44/4444344 3 44444444444444444/4444 4 -116- 200404764 第1 6表（續) 藥量(克/公頃） 野稗 野螢藺 見風紅 3-157 1000 0 / / 3-158 1000 4 4 4 3-159 1000 2 4 / 3-160 1000 1 4 / 3-161 1000 0 4 4 3-162 1000 4 4 4 3-163 1000 0 4 4 3-164 1000 0 4 4 3-165 1000 0 1 2 3-166 1000 4 4 4 3-167 1000 0 3 3 3-168 1000 / / / 3-169 1000 0 4 4 3-170 1000 0 0 0 3-171 1000 / / / 3-172 1000 / 0 0 3-173 1000 0 4 3 3-174 1000 1 1 4 3-175 1000 4 4 4 3-176 1000 0 4 4 3-177 1000 0 2 3 3-178 1000 0 4 4 3-179 1000 0 4 3 3-180 1000 0 2 3 3-181 1000 2 4 4 3-182 1000 4 4 4 3-183 1000 4 4 4 3-184 1000 0 2 1 3-185 1000 1 4 4 4-14 1000 4 4 4 4-39 1000 4 4 4 5-6 1000 / 4 4 5-29 1000 0 4 2 5-50 1000 0 2 1 5-64 1000 0 4 3 5-93 1000 / / / 6-8 1000 4 4 4 6-9 1000 4 4 4-115- 200404764 Table 16 (continued) Dosage (g / ha) Takino R3 Takahide 2-185 1000 2-186 1000 2-205 1000 2-209 1000 2-221 1000 2-227 1000 2- 244 1000 2-245 1000 2-246 1000 2-247 1000 3-2 1000 3-3 1000 3-4 1000 3-5 1000 3-6 1000 3-8 1000 3-13 1000 3-18 1000 3-19 1000 3-22 1000 3-23 1000 3-24 1000 3-25 1000 3-29 1000 3-32 1000 3-36 1000 3-37 1000 3-38 1000 3-46 1000 3-47 1000 3-48 1000 3- 49 1000 3-53 1000 3-61 1000 3-79 1000 3-80 1000 3-83 1000 3-156 1000 4/1412 2/422003244401342 1241104002 4 44/444/0444444444444 // 444444444 // 4 3 4/4 44 / 44/4444344 3 44444444444444444444/4444 4 -116- 200404764 Table 16 (continued) Dosage (g / ha) Nori Noguchi see wind red 3-157 1000 0 / / 3-158 1000 4 4 4 3 -159 1000 2 4 / 3-160 1000 1 4 / 3-161 1000 0 4 4 3-162 1000 4 4 4 3-163 1000 0 4 4 3-164 1000 0 4 4 3-165 1000 0 1 2 3- 166 1000 4 4 4 3-167 1000 0 3 3 3-168 1000 // // 3-169 1000 0 4 4 3-170 1000 0 0 0 3-171 1000 // // 3-172 1000/0 0 3-173 1000 0 4 3 3-174 1000 1 1 4 3-175 1000 4 4 4 3-176 1000 0 4 4 3-177 1000 0 2 3 3-178 1000 0 4 4 3-179 1000 0 4 3 3-180 1000 0 2 3 3-181 1000 2 4 4 3-182 1000 4 4 4 3-183 1000 4 4 3-184 1000 0 2 1 3-185 1000 1 4 4 4-14 1000 4 4 4 4-39 1000 4 4 4 5-6 1000/4 4 5-29 1000 0 4 2 5-50 1000 0 2 1 5-64 1000 0 4 3 5-93 1000 // // 6-8 1000 4 4 4 6-9 1000 4 4 4

-117- 200404764 第1 6表（續） 藥量(运公頃) 稗野 R3 野螢藺 見風紅 6-10 1000 6-19 1000 6-27 1000 6-28 1000 6-29 1000 6-32 1000 6-33 1000 6-60 1000 6-62 1000 6-73 1000 6-82 1000 6-83 1000 6-113 1000 6-339 1000 6-340 1000 6-341 1000 6-342 1000 6-343 1000 6-344 1000 6-345 1000 6-346 1000 6-347 1000 6-348 1000 6-349 1000 6-350 1000 6-351 1000 6-352 1000 6-353 1000 6-354 1000 6-355 1000 6-356 1000 6-357 1000 6-358 1000 6-359 1000 6-360 1000 6-361 1000 6-362 1000 6-363 1000 44444444444441444444//4/444/44/4//1/// 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 3 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 / / 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 / / / / / /-117- 200404764 Table 16 (continued) Dose (transportation hectare) Takino R3 Takino Hotaru see red 6-10 1000 6-19 1000 6-27 1000 6-28 1000 6-29 1000 6-32 1000 6-33 1000 6-60 1000 6-62 1000 6-73 1000 6-82 1000 6-83 1000 6-113 1000 6-339 1000 6-340 1000 6-341 1000 6-342 1000 6-343 1000 6- 344 1000 6-345 1000 6-346 1000 6-347 1000 6-348 1000 6-349 1000 6-350 1000 6-351 1000 6-352 1000 6-353 1000 6-354 1000 6-355 1000 6-356 1000 6-357 1000 6-358 1000 6-359 1000 6-360 1000 6-361 1000 6-362 1000 6-363 1000 44444444444441444444 // 4/444/44/4 // 1 /// 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 3 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 / / 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 / / / / / /

200404764 第1 6表（續） 藥量(克/公頃) 6-364 1000 6-365 1000 6-366 1000 6-367 1000 6-368 1000 6-369 1000 6-370 1000 6-371 1000 6-372 1000 6-373 1000 6-374 1000 6-375 1000 6-376 1000 6-377 1000 6-378 1000 6-379 1000 6-380 1000 6-381 1000 6-382 1000 6-383 1000 7-60 1000 7-217 1000 8-56 1000 9-56 1000 10-1 1000 10-2 1000 10-8 1000 10-12 1000 10-13 1000 10-14 1000 10-15 1000 10-16 1000 10-17 1000 10-18 1000 10-19 1000 10-20 1000 10-21 1000 10-23 1000200404764 Table 16 (continued) Dose (g / ha) 6-364 1000 6-365 1000 6-366 1000 6-367 1000 6-368 1000 6-369 1000 6-370 1000 6-371 1000 6-372 1000 6-373 1000 6-374 1000 6-375 1000 6-376 1000 6-377 1000 6-378 1000 6-379 1000 6-380 1000 6-381 1000 6-382 1000 6-383 1000 7-60 1000 7 -217 1000 8-56 1000 9-56 1000 10-1 1000 10-2 1000 10-8 1000 10-12 1000 10-13 1000 10-14 1000 10-15 1000 10-16 1000 10-17 1000 10-18 1000 10-19 1000 10-20 1000 10-21 1000 10-23 1000

野螢藺 見風紅 //////////////////444444/4444444444444 // // // /////////14343/4444444444444 -119- 200404764 藥量(克/公頃） 野稗 野螢藺 見風紅 .i l· V 、 1 - - 46894579089167131Ψ7 22223333455U-· 12-lT - i - I I I I I f I I - o 1 _ -222 000000000000-1111121212 11 11 1x 1x 1i li 11 11 1x ΊΧ 1x . 1X 11 oooooooooooooooooo ΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΩ oooooooooooooooooo 11 1x il lx 1i lx 1x 1x 1M 1x 1x Ίχ 1X 11 1X 1— 003214012//120401 444444/44///444/44 444444444//4444444 試驗例3 對移植水稻的藥害實驗 在75平方公分的塑膠壺中塡充土壤（栽植土充水至 水深5公分的狀態下，將2株2葉期的稻米（品種：日本晴） 移植深度爲1公分。在溫室內育成，移植5天後，以本發明 化合物（第1表至第1 3表所記載的化合物）爲有效成分，處 理所定有效藥量（克/公頃)藥液之藥劑。接者就在溫室內育成 、處理2 1天後除草效果進行調查，與沒有處理做比較，從 試驗例1的基準來評估除草效果。結果如第1 7表所示。Wild firefly sees the red /////////////////// 444444/4444444444444 // // ///////// 14343/4444444444444 -119- 200404764 medicine Amount (g / hectare) Nori Noguchi sees red. Il · V, 1--46894579089167131Ψ7 22223333455U- · 12-lT-i-IIIII f II-o 1 _ -222 000000000000-1111121212 11 11 1x 1x 1i li 11 11 1x ΊΧ 1x. 1X 11 oooooooooooooooooo ΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΟΩ oooooooooooooooooo 11 1x il lx 1i lx 1x 1x 1M 1x 1x Ίχ 1X 11 1X 1— 003214012 // 120401 444/444/444/44/444/44/44/44/444/44/44/44/444/44/44 Experiments on the phytotoxicity of rice were carried out in a 75-cm-cm plastic pot filled with soil (the planting soil was filled with water to a depth of 5 cm), and 2 rice plants (variety: Nihon Haru) at the 2-leaf stage were transplanted to a depth of 1 cm. Incubate in the laboratory. After 5 days of transplantation, the compound of the present invention (compounds listed in Tables 1 to 13) is used as an active ingredient to process a drug solution of a predetermined effective drug amount (g / ha). Investigate the weeding effect after 2 days of incubation and treatment in the room. Compare with no treatment. The herbicidal effect was evaluated on the basis of Test Example 1. The results are shown in Table 17 below.

-120- 200404764 第1 7表 藥量(克/公 頃） 稻米 1-2 1000 1 1-8 1000 0 1-23 1000 3 1-27 1000 4 1-28 1000 2 1-29 1000 0 1-30 1000 2 1-32 1000 1 1-36 1000 3 1-38 1000 2 1-40 1000 1 1-41 1000 3 1-43 1000 0 1-44 1000 1 1-47 1000 1 1-50 1000 1 1-59 1000 3 1-81 1000 0 1-84 1000 1 1-88 1000 1 1-89 1000 1 1-90 1000 0 1-91 1000 1 1-92 1000 3 1-93 1000 0 1-94 1000 1 1-95 1000 1 1-102 1000 3 1-103 1000 0 1-107 1000 3 1-108 1000 3 1-112 1000 0 M23 1000 0 1-124 1000 0 1-165 1000 1 1-177 1000 1 1-183 1000 2 1-189 1000 0 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 1-190 1000 0 1-192 1000 2 1-193 1000 3 1-198 1000 4 1-199 1000 2 1-215 1000 0 1-237 1000 0 1-245 1000 0 1-251 1000 0 1-254 1000 1 1-257 1000 2 1-258 1000 0 1-265 1000 0 1-266 1000 1 1-268 1000 1 1-273 1000 1 1-279 1000 0 1-282 1000 1 1-285 1000 0 1-286 1000 0 1-288 1000 / 1-291 1000 1 1-292 1000 1 1-323 1000 0 1-324 1000 0 1-325 1000 0 1-326 1000 1 1-327 1000 1 1-328 1000 2 2-8 1000 0 2-9 1000 0 2-12 1000 1 2-23 1000 1 2-24 1000 1 2-27 1000 1 2-28 1000 0 2-29 1000 1 2-30 1000 0 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 2-36 1000 1 2-37 1000 0 2-38 1000 1 2-41 1000 1 2-43 1000 1 2-51 1000 1 2-60 1000 0 2-61 1000 0 2-63 1000 1 2-64 1000 4 2-65 1000 1 2-66 1000 1 2-67 1000 1 2-68 1000 1 2-69 1000 0 2-70 1000 3 2-71 1000 1 2-72 1000 0 2-73 1000 0 2-76 1000 1 2-79 1000 0 2-81 1000 1 2-82 1000 1 2-83 1000 0 2-85 1000 4 2-86 1000 1 2-87 1000 1 2-88 1000 2 2-92 1000 / 2-93 1000 3 2-94 1000 1 2-98 1000 0 2-130 1000 0 2-167 1000 1 2-169 1000 0 2-176 1000 2 2-177 1000 2 2-184 1000 3 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 2-185 1000 4 2-186 1000 3 2-205 1000 / 2-209 1000 0 2-221 1000 1 2-227 1000 2 2-244 1000 0 2-245 1000 1 2-246 1000 0 2-247 1000 1 3-2 1000 2 3-3 1000 0 3-4 1000 0 3-5 1000 0 3-6 1000 0 3-8 1000 0 3-13 1000 0 3-18 1000 1 3-19 1000 1 3-22 1000 0 3-23 1000 0 3-24 1000 0 3-25 1000 0 3-29 1000 2 3-32 1000 0 3-36 1000 0 3-37 1000 0 3-38 1000 1 3-46 1000 3 3-47 1000 1 3-48 1000 0 3-49 1000 0 3-53 1000 0 3-61 1000 0 3-79 1000 0 3-80 1000 0 3-83 1000 / 3-156 1000 0 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 3-157 1000 0 3-158 1000 0 3-159 1000 0 3-160 1000 0 3-161 1000 0 3-162 1000 3 3-163 1000 0 3-164 1000 0 3-165 1000 0 3-166 1000 0 3-167 1000 0 3-168 1000 / 3-169 1000 0 3-170 1000 0 3-171 1000 / 3-172 1000 0 3-173 1000 0 3-174 1000 0 3-175 1000 1 3-176 1000 0 3-177 1000 0 3-178 1000 0 3-179 1000 0 3-180 1000 0 3-181 1000 0 3-182 1000 1 3-183 1000 1 3 -184 1000 0 3-185 1000 0 4-14 1000 1 4-39 1000 2 5-6 1000 0 5-29 1000 0 5-50 1000 0 5-64 1000 0 5-93 1000 / 6-8 1000 2 6-9 1000 0 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 6-10 1000 1 6-19 1000 4 6-27 1000 3 6-28 1000 3 6-29 1000 4 6-32 1000 2 6-33 1000 3 6-60 1000 1 6-62 1000 1 6-73 1000 1 6-82 1000 1 6-83 1000 1 6-113 1000 0 6-339 1000 0 6-340 1000 1 6-341 1000 3 6-342 1000 2 6-343 1000 4 6-344 1000 1 6-345 1000 1 6-346 1000 0 6-347 1000 0 6-348 1000 1 6-349 1000 2 6-350 1000 1 6-351 1000 1 6-352 1000 0 6-353 1000 1 6-354 1000 1 6-355 1000 2 6-356 1000 1 6-357 1000 1 6-358 1000 0 6-359 1000 0 6-360 1000 0 6-361 1000 / 6-362 1000 / 6-363 1000 / 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 6-364 1000 / 6-365 1000 / 6-366 1000 / 6-367 1000 / 6-368 1000 / 6-369 1000 / 6-370 1000 / 6-371 1000 / 6-372 1000 / 6-373 1000 / 6-374 1000 / 6-375 1000 / 6-376 1000 / 6-377 1000 / 6-378 1000 / 6-379 1000 / 6-380 1000 / 6-381 1000 / 6-382 1000 1 6-383 1000 0 7-60 1000 1 7-217 1000 0 8-56 1000 1 9-56 1000 0 10-1 1000 / 10-2 1000 0 10-8 1000 0 10-12 1000 0 10-13 1000 0 10-14 1000 0 10-15 1000 0 10-16 1000 0 10-17 1000 0 10-18 1000 0 10-19 1000 0 10-20 1000 0 10-21 1000 0 10-23 1000 1 200404764 第1 7表（續) 藥量(克/公 頃） 稻米 10-24 1000 0 10-26 1000 1 10-28 1000 1 10-29 1000 1 10-34 1000 0 10-35 1000 1 10-37 1000 0 10-39 1000 0 10-40 1000 0 10-58 1000 / 10-59 1000 / 10-116 1000 0 11-7 1000 0 11-11 1000 0 11-23 1000 1 12-1 1000 0 12-4 1000 0 12-7 1000 0 200404764 ^ φ\ 4 對旱田作物的莖葉處理除草效果實驗 在36平方公分的塑膠壺中塡充土壤（栽植土）’播_ 旱田作物之野稗、蒼耳的種子，於覆土 土壤約20立方& 分後，在溫室內育成。在供試驗的植物一個葉期期間’ 照製劑例1〜4的標準來製備本發明化合物（第1表至第1 表所記載的化合物）爲有效成分，處理所定有效藥纛（$ 公頃）藥液之藥劑，稀釋成相當於1 0 0 0公升/公頃的水羹’ 散布處理。接者就在溫室內育成、處理2 1天後除草效果 進行調查，與沒有處理做比較，從試驗例1的基準來評估 有沒有除草效果。 本發明化合物中，至少i — 2、1 — 8、1 一 23 ， 1 - 27、1-28，1一30、1 一 36、卜 40、 丄-41、1 - 44、1 一 47、1 - 59、1 - 84、 1- SS、1-89、1 一 91、1-92、1 - 93、-120- 200404764 Table 17 Dose (g / ha) Rice 1-2 1000 1 1-8 1000 0 1-23 1000 3 1-27 1000 4 1-28 1000 2 1-29 1000 0 1-30 1000 2 1-32 1000 1 1-36 1000 3 1-38 1000 2 1-40 1000 1 1-41 1000 3 1-43 1000 0 1-44 1000 1 1-47 1000 1 1-50 1000 1 1-59 1000 3 1-81 1000 0 1-84 1000 1 1-88 1000 1 1-89 1000 1 1-90 1000 0 1-91 1000 1 1-92 1000 3 1-93 1000 0 1-94 1000 1 1-95 1000 1 1-102 1000 3 1-103 1000 0 1-107 1000 3 1-108 1000 3 1-112 1000 0 M23 1000 0 1-124 1000 0 1-165 1000 1 1-177 1000 1 1-183 1000 2 1 -189 1000 0 200404764 Table 17 (continued) Dose (g / ha) Rice 1-190 1000 0 1-192 1000 2 1-193 1000 3 1-198 1000 4 1-199 1000 2 1-215 1000 0 1-237 1000 0 1-245 1000 0 1-251 1000 0 1-254 1000 1 1-257 1000 2 1-258 1000 0 1-265 1000 0 1-266 1000 1 1-268 1000 1 1-273 1000 1 1-279 1000 0 1-282 1000 1 1-285 1000 0 1-286 1000 0 1-288 1000 / 1-291 1000 1 1-292 1000 1 1-323 1000 0 1-324 1000 0 1-325 1000 0 1-326 1000 1 1-3 27 1000 1 1-328 1000 2 2-8 1000 0 2-9 1000 0 2-12 1000 1 2-23 1000 1 2-24 1000 1 2-27 1000 1 2-28 1000 0 2-29 1000 1 2- 30 1000 0 200404764 Table 17 (continued) Dose (g / ha) Rice 2-36 1000 1 2-37 1000 0 2-38 1000 1 2-41 1000 1 2-43 1000 1 2-51 1000 1 2 -60 1000 0 2-61 1000 0 2-63 1000 1 2-64 1000 4 2-65 1000 1 2-66 1000 1 2-67 1000 1 2-68 1000 1 2-69 1000 0 2-70 1000 3 2 -71 1000 1 2-72 1000 0 2-73 1000 0 2-76 1000 1 2-79 1000 0 2-81 1000 1 2-82 1000 1 2-83 1000 0 2-85 1000 4 2-86 1000 1 2 -87 1000 1 2-88 1000 2 2-92 1000 / 2-93 1000 3 2-94 1000 1 2-98 1000 0 2-130 1000 0 2-167 1000 1 2-169 1000 0 2-176 1000 2 2 -177 1000 2 2-184 1000 3 200404764 Table 17 (continued) Charge (g / ha) Rice 2-185 1000 4 2-186 1000 3 2-205 1000 / 2-209 1000 0 2-221 1000 1 2-227 1000 2 2-244 1000 0 2-245 1000 1 2-246 1000 0 2-247 1000 1 3-2 1000 2 3-3 1000 0 3-4 1000 0 3-5 1000 0 3-6 1000 0 3-8 1000 0 3-13 1000 0 3-18 1000 1 3-19 1000 1 3-22 1000 0 3-23 1000 0 3-24 1000 0 3-25 1000 0 3-29 1000 2 3-32 1000 0 3-36 1000 0 3-37 1000 0 3-38 1000 1 3-46 1000 3 3-47 1000 1 3-48 1000 0 3-49 1000 0 3-53 1000 0 3-61 1000 0 3-79 1000 0 3-80 1000 0 3-83 1000 / 3-156 1000 0 200404764 1 Table 7 (continued) Dose (g / ha) Rice 3-157 1000 0 3-158 1000 0 3-159 1000 0 3-160 1000 0 3-161 1000 0 3-162 1000 3 3-163 1000 0 3- 164 1000 0 3-165 1000 0 3-166 1000 0 3-167 1000 0 3-168 1000 / 3-169 1000 0 3-170 1000 0 3-171 1000 / 3-172 1000 0 3-173 1000 0 3- 174 1000 0 3-175 1000 1 3-176 1000 0 3-177 1000 0 3-178 1000 0 3-179 1000 0 3-180 1000 0 3-181 1000 0 3-182 1000 1 3-183 1000 1 3- 184 1000 0 3-185 1000 0 4-14 1000 1 4-39 1000 2 5-6 1000 0 5-29 1000 0 5-50 1000 0 5-64 1000 0 5-93 1000 / 6-8 1000 2 6- 9 1000 0 200404764 Table 17 (continued) Dose (g / ha) Rice 6-10 1000 1 6-19 1000 4 6-27 1000 3 6-28 1000 3 6-29 1000 4 6-32 1000 2 6 -33 1000 3 6-60 1000 1 6-62 1000 1 6-73 1000 1 6-82 1000 1 6-83 1000 1 6-113 1000 0 6-339 1000 0 6-340 1000 1 6-341 1000 3 6-342 1000 2 6-343 1000 4 6-344 1000 1 6-345 1000 1 6-346 1000 0 6-347 1000 0 6-348 1000 1 6-349 1000 2 6-350 1000 1 6-351 1000 1 6-352 1000 0 6-353 1000 1 6-354 1000 1 6-355 1000 2 6-356 1000 1 6-357 1000 1 6-358 1000 0 6-359 1000 0 6-360 1000 0 6-361 1000 / 6-362 1000 / 6-363 1000 / 200404764 Table 17 (continued) Dose (g / ha) Rice 6-364 1000 / 6-365 1000 / 6-366 1000 / 6-367 1000 / 6-368 1000 / 6-369 1000 / 6-370 1000 / 6-371 1000 / 6-372 1000 / 6-373 1000 / 6-374 1000 / 6-375 1000 / 6-376 1000 / 6-377 1000 / 6-378 1000 / 6-379 1000 / 6-380 1000 / 6-381 1000 / 6-382 1000 1 6-383 1000 0 7-60 1000 1 7-217 1000 0 8-56 1000 1 9-56 1000 0 10-1 1000 / 10-2 1000 0 10-8 1000 0 10-12 1000 0 10-13 1000 0 10-14 1000 0 10-15 1000 0 10-16 1000 0 10-17 1000 0 10-18 1000 0 10-19 1000 0 10-20 1000 0 10-21 1000 0 10-23 1000 1 200 404764 Table 17 (continued) Dose (g / ha) Rice 10-24 1000 0 10-26 1000 1 10-28 1000 1 10-29 1000 1 10-34 1000 0 10-35 1000 1 10-37 1000 0 10-39 1000 0 10-40 1000 0 10-58 1000 / 10-59 1000 / 10-116 1000 0 11-7 1000 0 11-11 1000 0 11-23 1000 1 12-1 1000 0 12-4 1000 0 12-7 1000 0 200404764 ^ φ \ 4 Experiments on the weeding effect of stems and leaves on dry-field crops In a 36-cm plastic pot filled with soil (planting soil) 'seeding_ The seeds of wild field and cocklebur of dry-field crops, After covering the soil with about 20 cubic meters, it is grown in a greenhouse. During one leaf stage of the plant to be tested ', the compounds of the present invention (compounds listed in Tables 1 to 1) were prepared according to the standards of Formulation Examples 1 to 4 as active ingredients, and the prescribed effective medicinal tincture ($ ha) was processed. Liquid medicine, diluted to the equivalent of 1,000 liters / ha of leech 'spreading treatment. The recipients investigated the herbicidal effect after 21 days of incubation and treatment in a greenhouse, and compared it with no treatment, and evaluated the herbicidal effect based on the test example 1. In the compounds of the present invention, at least i-2, 1-8, 1, 1-23, 1-27, 1-28, 1-30, 1-36, Bu 40, 丄 -41, 1-44, 1-47, 1 -59, 1-84, 1-SS, 1-89, 1-91, 1-92, 1-93,

1 - 94、1 - 95、1一1〇2、1-103、1 - 1 〇8、1-165、1 — 177、1 - 183、1 - 18 9、1-190、1-193、1 - 199、1 - 237、 ^-251、1 - 254、1-258、1 - 266、1 〜279、1 - 286、1 — 291、1-324、1-326、1-327、1 — 328、2 - 12、2 - 23、 2 - 24、2 - 27、2 - 28、2 - 29、2 - 30、 2- 36、2 - 41、2- 51、2 - 61、2 - 63、 2 - 64、2 — 65、2 - 66、2 - 67、2 - 68、 -129- 200404764 2 - 69、2-70、2 - 71、2 - 72、2 - 73、 2-76、2 — 79、2-81、2-82、2-83、 2 - 85、2 - 86、2 - 87、2-88、2 — 93、 2- 94、2-130、2-167、2-169、2- 176、2-177、2- 184、2- 185、2- 1 86、2-209、2 — 221、2-244、2 - 24 5、2 — 247、3 - 2、3 — 5、3-8、3 — 13、 3- 18、3 - 19、3 — 23、3 - 24、3 - 25、 3 — 29、3 — 36、3 — 37、3-38、3-46、 3 - 47、3 — 48、3-53、3 — 61、3 — 80、 3-156、3 - 158、3-161、3-162、3 一163、3-164、3-166、3 — 168、3-169、3-170、3-172、3-173、3-1 81、3 - 182、3 — 183、3 — 185、4 — 39、 5 — 93、6 — 8、6 — 9、6 — 10、6 — 1 9、6 — 27、6-28、6-29、6 - 32、6-33、6-60、6-62、6-73、6 — 82、6-83、6 — 341、6 — 342、6 — 346、6 — 348、6 - 3 49、6-350、6 - 351、6 — 352、6 — 35 3、6 - 354、6 - 355、6 - 356、6 — 357、 6 — 360、6-362、6 — 363、6 - 364、6 一365、6-366、6 — 367、7 — 60、10 — 2、10 - 8、10 - 12、10 — 13、10-14、 10-15、 10 — 16、 10 — 17、 10 — 18、 1 -130- 200404764 〇 一 19、 10 — 20、 1〇 一 21 、 10 — 23、 10 一 24、 1〇 一 26、 10 — 28、 10 — 29、 10 — 34、 10 — 35、 10 — 37、 10 — 39、 10-4 0、10 - 116、11 — 7、12 - 1、12 — 4、1 2 — 7 ，顯示對野稗或蒼耳有除草之效果。 【圖式簡單說明】：無1-94, 1-95, 1-102, 1-103, 1-1 08, 1-165, 1-177, 1-183, 1-18 9, 1-190, 1-193, 1 -199, 1-237, ^ -251, 1-254, 1-258, 1-266, 1 to 279, 1-286, 1-291, 1-324, 1-326, 1-327, 1-328 , 2-12, 2-23, 2-24, 2-27, 2-28, 2-29, 2-30, 2- 36, 2-41, 2- 51, 2-61, 2-63, 2 -64, 2 — 65, 2-66, 2-67, 2-68, -129- 200404764 2-69, 2-70, 2-71, 2-72, 2-73, 2-76, 2-79 , 2-81, 2-82, 2-83, 2-85, 2-86, 2-87, 2-88, 2-93, 2-94, 2-130, 2-167, 2-169, 2 -176, 2-177, 2- 184, 2- 185, 2- 1 86, 2-209, 2-221, 2-244, 2-24 5, 2-247, 3-2, 3-5, 3 -8, 3 — 13, 3- 18, 3-19, 3-23, 3-24, 3-25, 3-29, 3-36, 3-37, 3-38, 3-46, 3-47 3-48, 3-53, 3-61, 3-80, 3-156, 3-158, 3-161, 3-162, 3-163, 3-164, 3-166, 3-168, 3 -169, 3-170, 3-172, 3-173, 3-1 81, 3-182, 3 — 183, 3 — 185, 4 — 39, 5-93, 6-8, 6-9, 6-10, 6-1 9, 6-27, 6-28, 6-29, 6-32, 6-33, 6-60, 6-62 6-73, 6 — 82, 6-83, 6 — 341, 6 — 342, 6 — 346, 6 — 348, 6 — 3 49, 6 — 350, 6 — 351, 6 — 352, 6 — 35 3 , 6-354, 6-355, 6-356, 6 — 357, 6 — 360, 6-362, 6 — 363, 6 — 364, 6 — 365, 6 — 366, 6 — 367, 7 — 60, 10 — 2, 10-8, 10-12, 10-13, 10-14, 10-15, 10-16, 10-17, 10-18, 1 -130- 200404764 〇19, 10-20, 1〇 -21, 10-23, 10-24, 10-26, 10-28, 10-29, 10-34, 10-35, 10-37, 10-39, 10-4 0, 10-116, 11 — 7, 12-1, 12 — 4, 1 2 — 7, showing weeding effect on wild salamander or cocklebur. [Schematic description]: None

-13 1--13 1-

Claims (1)

200404764 拾、申請專利範圍： 1 ·—種通式⑴之鹵院磺_苯㈣生_其鹽類200404764 The scope of patents applied for: 1 · —Sulfur compounds of the general formula __benzene㈣ 生 _ 其 盐 {式中，R1爲鹵化（Cl，c6)院基； R爲氯原子、（Ci_c6)院基、烷氧基（c「c6)烷基、 (c「C6)k基羰基、鹵化^-^^烷基羰基、苯基羰基、 3有1個以上之相同或不同均可以的選自γ(γ如後述 所7Κ)之取代基的苯基羰基、烷氧基羰基、苯氧 基線基 '含有1個以上之相同或不同均可以的選自γ(γ 如後述所不）之取代基的取代苯氧基羰基、（C1_C6)烷基 石貝醯基、鹵化（Ci_C6)烷基磺醯基、苯基磺醯基或含有1 個以上之相同或不同均可以的選自γ(γ如後述所示）之 取代基的取代苯基磺醯基； Q係一種在構成原子中至少1個爲氮原子、且該氮原子 與Α的鍵結部位爲可經取代之雜環； A爲（CVCJ伸院基、含有選自鹵素原子、羥基、（ere」 k氧基、（C^C：6)烷氧基羰基或氰基之1個以上相同或 不同均可以的取代基之取代（Ci_C6)伸烷基、（C2_C6)伸 烯基、含有選自鹵素原子、羥基、（Ci_C6)烷氧基、（c「 CJ烷氧基羰基或氰基之i個以上相同或不同均可以的 取代基‘之取代（C2'C6)伸烯基或（C2-C6)伸炔基； G爲氧原子、硫原子、N-R3(其中，r3爲氧原子、 -132· 200404764 烷基、氰基、硝基、苯基（(Vc 個以上之相同或不同均可以的 仕環上ϊ 取代基的取代苯基一基:苯基(::=示)之 之相同或不同均可以的選自γ(γ如7 一 以上 的取代茏其、 俊述所不）之取代基 的取代本基）、N-0R4(其中，R4爲氧原子、（C「其、 苯基（CrCj垸基或在環上含有工個以 相兀土、 均可以的選自Y(Y如後述所示）之 同或不同 (C Γ ^ 取代基的取代苯基 兀基）或 n-NR5R6(其中，p5 u 汉及汉6爲相同或不同 均可以的氧原子、苯基或含丨個 上之相同或不同均可 以的培自Υ(Υ如後述所示）之取代基的取代苯基卜又， R5及R6同時爲（C3-C6)伸烷基）； m爲0或1之整數； X爲含選自相同或不同均可以的氧原子、鹵素原子、 (CrC6)燒基、（c2-c6)嫌基、（CVc6)炔基、環院 基、鹵化（cvc6)烷基、環鹵化（c3-C6)烷基、（^^。院 與基、鹵化d-cdi兀氧基、（c^-Cs)院硫基、鹵化（c「c ) 烷硫基、（Ci-C6)烷亞磺醯基、鹵化（Cl-C6)烷亞磺醯基、 (C「c6)烷磺醯基、（cvc6)烷磺醯基、鹵化（Ci-c6)院礦 醯基、苯基，含有1個以上之相同或不同均可以的選自 Y(Y如後述所示）之取代基的取代苯基、苯氧基，含有 1個以上之相同或不同均可以的選自Υ(Υ如後述所示） 之取代基的取代苯氧基、苯硫基，含有1個以上之相同 或不同均可以的選自Υ (Υ如後述所示）之取代基的取代 苯硫基、苯亞磺醯基，含有1個以上之相同或不同均可 -133- 200404764 基的苯亞磺醯基、苯 同均可以的選自γ(γ 、（CVC6)烷基羰基、 以的選自 Y(Y如後述所示）之取代 磺醯基，含有1個以上之相同或不 如後述·所示）之取代基的苯磺_ s 鹵化（Ci-Cg)院基鑛基、苯基羰其，a "Q有1個以上之相 丨口」驭个 基鑛基、（Ci-C：6)院氧基鑛基、羧基 畢卓（Κ6)烷胺羰 基、相同或不同均可以的（Cl_c6)垸胳销甘 1 6)沅妝釦基、苯胺羰基、 在環上含有1個以上之相同或不同 人丨丨口」习可以的選自γ(γ 如後述所示）之取代基的取代苯胺鑛 _ 碁、本基（cvc6：^ 胺羰基，在環上含有1個以上之相同 c m丨口」驭不冋均可以的選 自Y(Y如後述所示）之取代基的取代 取代本基（c^c6)烷胺羰 基、氧基、胺基、氰基或硝基之^ 4個取代基； y爲相同或不同均可以的鹵素原子、（Κ6)烷基、（c2_ 嫌基、（cvc6)炔基、環（c3_c6)烷基、鹵化（c「c6)院 基、環鹵化（C3-c6)烷基、（CVC6)烷氧基、鹵化（Κ6) 烷氧基、（cvcj烷硫基、鹵化（〇1<6)烷硫基、 烷亞磺醯基、鹵化（(VCJ烷亞磺醯基、（Κ6)烷磺醯 義、鹵化（C^CJ烷磺醯基、苯基、含有選自相同或不 同均可以的鹵素原子、（Ci_C6)烷基' (C^C6)烯基、（C，_ C6)块基、環（CrC6)院基、鹵化（C「c6)院基、環幽化（C3_C6) 元基、（cvcj院氧基、鹵化（c「c6)院氧基、（(^-(：6)院 基齒化（C「C6)院硫基、（C^Cs)院亞磺醯基、鹵化 (C「C6)院亞磺醯基、（κ6)烷磺醯基、鹵化（<：：1<6)烷 擴酶基、（(^-(：6)烷基羰基、鹵化（Ci_c6)烷基羰基、（cv -134- 6)火兀氧基鑛基、簿其 土、卑（cvc6)烷胺羰基、相同或不 同均可以的二（c c ρ — /、 6)丨兀肢羰基、羥基、胺基、氰基或 硝基之1-5個取代基的 ^ ^ ^ π 代苯基、苯氧基、含選自相同 不同均可以的鹵奉原 卞原子、（CVC,)烷基、（c2-c6)烯基、 (Cr C6)炔基、環 3 6) &基、鹵化（C i - C 6)烷基、環鹵 化（c 3 - C 6)院基、（c c 〜 6)j:兀氧基、鹵化（cvcj烷氧基、 (Ci C6)院硫基、鹵化 u & ^1<6)烷硫基、（CVC6)烷亞磺醯 基、鹵化（eve,)烷亞磺醯其 基、（Ci_c6)烷磺醯基、鹵化 (ci-c6)烷磺醯基、（cvc v卢宜班# 、& 6)院基釦基、鹵化（Ci-C6)烷基 羰基、（cvc6)院氧基羰基、錄 —、 瘦基、卓（c^c,)烷胺羰基、 相同或不同均可以的二（ — 1 h);兀fe耘基、羥基、胺基、 氰基或硝基之1-5個取代基的取 ^ 」取代本異基、苯硫基、含 選自相同或不同均可以的鹵奉 凶累原子、（CrC6)烷基、（C，- c6m基、（C2_C6)炔基、環· 6)院基、鹵化（CVC6)烷 基、環鹵化（C3-C6)烷基、（C c V户知甘 1 6)烷氧基、鹵化（C,-C6) h基、(Cl-C6)院硫基、齒化(Ci_c6)院硫 院亞磺驢基、齒化(C「C6)焼亞 ㈣ ^ /r v h、c 6)烷磺醯 、、、、七(Cl-C6)院磺醯基、(Ci、c6)烷基羰基 c6)烷基羰基、（Cl-C6)烷氧基羰基、 。 (1 胺羰基、相同或不同均可以的= 單（cvc0)烷 基、^ ^ -1? ^ ^ 1 〜CrC6)烷胺羰基、羥 基fe基、氧基或硝基之Μ個取代基 苯亞磺醯基、含選自相同或不η 代本硫基、 间均可以的h _ (c「c6)烷基、（C7-c6)儲基、（c Γ 的晦素原子、 基、鹵化（C「C6)烷基、環鹵仆Μ ^ (C3-C6)k -13 5' (cvqm 200404764 氧基、鹵化（(^-(：6)烷氧基、（C^c,)烷硫基、鹵化（Ci_c6) 烷硫基、（cvc6)烷亞磺醯基、鹵化（CVC6)烷亞磺醯基、 (C「C6)烷磺醯基、鹵化（Cl_C6)烷磺醯基、（(^-(：6)烷基 羰基、鹵化（cvc6)烷基羰基、（Ci-c,)烷氧基羰基、羧 基、單（(：「0：6)烷胺羰基、相同或不同均可以的二（Ci_c6) 烷胺羰基、羥基、胺基、氰基或硝基之1- 5個取代基的 取代苯亞磺醯基、苯磺醯基、含選自相同或不同均可以 的鹵素原子、（Ci-C,)烷基、（C2-C6)烯基、（c2-c6)炔基、 環（C3-C6)烷基、鹵化（Ci_c6)烷基、環鹵化（C3-C6)烷基、 (c「c6)院氧基、鹵化（c「c6)烷氧基、（cvc6)烷硫基、 鹵化（cvcj院硫基、（Ci_c6)烷亞磺醯基、鹵化（c「c6) 院亞磺醯基、（(：1<6)烷磺醯基、鹵化（CVC6)烷磺醯基、 (C「C6)院基羰基、鹵化（Ci_c6)烷基羰基、（CVC6)烷氧 基鑛基、羧基、單（Ci_C6)烷胺羰基、相同或不同均可 以的二（C^C6)烷胺羰基、羥基、胺基、氰基或硝基之1-5 個取代基的取代苯磺醯基、（C1-C6)烷基羰基、鹵化（c「 院基鑛基、苯基羰基、含選自相同或不同均可以的 國素原子、（Ci-C,)烷基、（c2-c6)烯基、（c2-c6)炔基、 Ttto 孩（(Vc6)烷基、鹵化（c「c6)烷基、環鹵化（κ6)烷基、 (c「c6)院氧基、鹵化（〇1_(：6)烷氧基、（CVC6)烷硫基、 圖化（Cl-C6)院硫基、（C^Cd烷亞磺醯基、鹵化（Ci-CJ ^亞磺驢基、（CVC6)烷磺醯基、鹵化（CVc6)烷磺醯基、 (ci-c6)烷基羰基、鹵化（Ci_c6)烷基羰基、（CVC6)烷氧 基鑛基、羧基、單（Ci_c6)烷胺羰基、相同或不同均可 200404764 以的二 個取 燒胺鑛基、經基、胺基、氣基或硝基之Μ 單（C *的取代苯基羰基、（CVC6)烷氧基羰基、羧基、 胺幾C1'c6)f胺羯基、相同或不间％可以的二（c「cfi)烷 子之本胺羰基、含選自相同卖不同均可以的鹵素原 户（C「C6)院基、（C2_C6)燃基、（^义）快基、環 基鹵化（C「C6)烷基、環鹵化（C3_C6)烷基、（Ci_C6) :氧基、鹵化(Cl-C6)院氧基、(Ci')院硫s、鹵化(c:_ 烷硫基、（Ci_C6)烷亞磺醯基、國化（Ci_C6)烷亞磺醯 基、（1-〇6)烷磺醯基、鹵化（Ci_C6)烷磺醯基、 烷基羰基、鹵化（CrG)烷基羰基、（CVC6)烷氧基羰基、6 羧基、單（Ci-c：6)烷胺羰基、相同或不同均可以的二（c「 ce)烷胺羰基、羥基、胺基、氰基或硝基之丨_5個取代 基的取代苯胺羯基、苯基（Cl-C6)烷胺羰基、在環上含 有1個以上選自相同或不同均可以的鹵素原子、（c^c) 烷基、（c2-c6)烯基、（c2-c6)炔基、環（CVC6)烷基、鹵 化（C「C6)院基、環鹵化（C3-C6)院基、（CrC6)院氧基、 鹵化（C「C6)|兀氧基、（CrCd院硫基、鹵化（c「c6)院硫 基、（cvcd烷亞磺醯基、鹵化（cvc6)烷亞磺醯基、（c「 C6)烷磺醯基、鹵化（CVCJ烷磺醯基、（Ci_c6)院基鑛基、 商化^厂匚6)烷基羰基、（cvc6)烷氧基羰基、羧基、單 (C^-Cd烷胺羰基、選自相同或不同均可以的二（Ci_c6) 烷胺羰基、羥基、胺基、氰基或硝基之1 - 5個取代基之 取代苯基（C^CJ烷胺羰基、羥基、胺基、氰基或硝基 之1 - 5個取代基；又， -137- 200404764 γ係與苯環上接鄰之碳原子一起爲選自相同或不同均可 以的氧原子、硫原子或氮原子（該氮原子係爲由氫原子、 (CrC6)烷基、（C2-C6)烯基、（C2-C6)炔基或環（(：3<6)烷 基所取代者）之1至2個雜原子’介於（Cl-C4)伸烷基中 而形成之5至6員環者}。 2 .如申請專利範圍第1項之鹵烷磺醯苯胺衍生物或其鹽 類，其中·· Q爲〜種在構成原子中至少有1個爲氮原子、且構成氮 原子成爲A的鍵結部位之元素爲碳原子、氮原子、氧 原子、硫原子或磷原子之4至13員雜原子，或選自1 個以上相同或不同均可以的鹵素原子、（C^C6)烷基、 (C2-C6)烯基、（c2-c6)炔基、瓌（C3-C7)烷基、鹵化（CVC6) 烷基、環鹵化（c3-c7)烷基、（Ci-Cd烷氧基、鹵化（c「c6) 院氧基、（Ci-Cd院硫基、鹵化（c「c6)院硫基、（Ci-CJ 烷亞磺醯基、鹵化（c「c6)烷亞磺醯基、（cvc6)烷磺醯 基、鹵化（CVC6)烷磺醯基、苯基、含有1個以上之相 同或不同均可以的選自Y(Y與第1項相同）之取代基的 取代苯基、苯基（C^-Cs)院基、在環上含有1個以上之 相同或不同均可以的選自Y(Y與上述記載相同）之取代 基的苯基（Cl-c6)烷基、苯氧基，含有1個以上之相同 或不同均可以的選自Y (γ與上述記載相同）之取代基的 取代苯氧基、苯硫基，含有1個以上相同或不同均可以 的選自Υ(Υ與上述記載相同）之取代基的取代苯硫基、 苯亞磺醯基，含有1個以上之相同或不同均可以的選自 -138- 200404764 Y (γ與上述記載相同）之取佧甘& # 其 取代基的本亞磺醯基、苯磺醯 土，含有丨_以上之相同或丨同均可以的選自γ(γ與 上述記載相同)之取代基的苯晴_基、(Ci')賴基、 齒化（eve,)烷基羰基、苯基羰其， 土瑗基，曰有丨個以上之相 问：不同均可以的選自Y(Y與上述記載相同)之取代基 的苯基羰基、（Cl-CJ烷氧基羰基、羧基、單（Ci_c6)烷 胺绩基、相同或不同均可以的二^「06)院胺凝基、苯 ^竣基、在環上曰有1個以上之相同或不同均可以的選 Y(Y與上述載相同）之取代基的苯胺鑛基、苯基 (C^C0)烷胺羰基、在環上含有1個以上之相同或不同 均可以的選自γ(γ與上述記載相同）之取代基的苯基 (C 1 · c6)烷胺羰基、雜環基（雜環基係選自於下列：啦陡 基、吡啶-N-氧化物基、嘧啶基、吡畊基、三畊基、咲 喃基、四氫呋喃基、噻吩基、四氫噻吩基、四氫哌喃基、 四氫硫代派喃基、曙11坐基 '異嘻哩基、曙二哇基、嚷口坐 基、異噻唑基、噻二唑基、咪唑基、***基、壯哗基、 嗎福啉基）、含有1個以上之相同或不同均可以的選自 Υ(γ與上述記載相同）之取代基的取代雜環基（雜環基與 上述記載相同）、羥基、胺基、氰基或硝基之取代基取 代的構成原子中至少有1個爲氮原子，且構成氮原子與 Α之間的鍵結部位之元素爲碳原子、氮原子、氧原子硫 原子或憐原子之4至13貝雜環。 ，如申請專利範圍第2項之鹵院磺醯苯胺衍生物或其鹽 類，其中Q如下通式所不： 139- 200404764{Wherein R1 is a halogenated (Cl, c6) radical; R is a chlorine atom, (Ci_c6) radical, alkoxy (c "c6) alkyl, (c" C6) k-based carbonyl, halogenated ^-^ ^ Alkylcarbonyl, phenylcarbonyl, and 3 have one or more of the same or different substituents selected from the group consisting of phenylcarbonyl, alkoxycarbonyl, and phenoxyline groups which are substituted with γ (γ is as described below 7K) One or more of the same or different substituents selected from the group consisting of substituted phenoxycarbonyl groups of γ (γ as not described below), (C1_C6) alkylsulfenyl, halogenated (Ci_C6) alkylsulfonyl, benzene A sulfosulfanyl group or a substituted phenylsulfonyl group containing one or more of the same or different substituents selected from γ (γ is shown below); Q is a type in which at least one of the constituent atoms is a nitrogen atom And the bonding site between the nitrogen atom and A is a heterocyclic ring which may be substituted; A is (CVCJ Extender group, contains a halogen atom, a hydroxyl group, (ere) koxy group, (C ^ C: 6) alkane (Ci_C6) alkylene, (C2_C6) alkenyl, one or more substituents which may be the same or different from the oxycarbonyl or cyano group, and contains a halogen atom, a hydroxyl group, (Ci _C6) alkoxy, (c "CJ alkoxycarbonyl or cyano i or more of the same or different substituents can be substituted by (C2'C6) alkenyl or (C2-C6) alkynyl; G is an oxygen atom, a sulfur atom, and N-R3 (wherein, r3 is an oxygen atom, -132 · 200404764 alkyl, cyano, nitro, and phenyl ((Vc or more may be the same or different, the same ring may be used on the official ring) Substituent of substituted phenyl group: the same as or different from phenyl group (:: = indicated) may be selected from the substituents selected from the group consisting of γ (where γ is substituted by 7 or more, which is not described above) Group), N-0R4 (wherein R4 is an oxygen atom, (C, its, phenyl group (CrCj 垸 group or a ring containing a coherent soil) may be selected from Y (Y is shown below) The same or different (substituted phenyl carboyl with C Γ ^ substituents) or n-NR5R6 (where p5 u and han 6 are the same or different oxygen atoms, phenyl groups or the same or Different can be substituted from the substituted phenyl group of Υ (as shown below), R5 and R6 are both (C3-C6) alkylene); m is an integer of 0 or 1; X is an integer containing From phase Or different oxygen atoms, halogen atoms, (CrC6) alkyl, (c2-c6) alkyl, (CVc6) alkynyl, cycloalkyl, halogenated (cvc6) alkyl, cyclohalogenated (c3-C6) alkane Radicals, (^^. Radicals, halogenated d-cdioxy radicals, (c ^ -Cs) alkylthio radicals, halogenated (c "c) alkylthio radicals, (Ci-C6) alkylsulfinylfluorenyl radicals, halogenated radicals (Cl-C6) alkanesulfinyl, (C "c6) alkanesulfonyl, (cvc6) alkanesulfonyl, halogenated (Ci-c6) sulfonium, phenyl, containing one or more of the same or Differently substituted phenyl and phenoxy groups selected from the substituents of Y (Y is shown later) may contain one or more of the same or different substituents selected from the group consisting of Υ (Υ is shown later) Substituted phenoxy and phenylthio groups containing one or more substituted phenylthio groups and phenylsulfinyl groups which may be the same or different and are selected from the group consisting of Υ (Υ will be described later) and contain one or more The same or different can be -133- 200404764 phenylsulfinyl and benzene can be selected from γ (γ, (CVC6) alkylcarbonyl, and selected from Y (Y is shown below) Sulfonyl, containing 1 or more of the same or As mentioned later, the benzene sulfonium s-halogenated (Ci-Cg) substituents, phenylcarbonyl groups, a " Q has more than one phase 丨 " Ci-C: 6) Oxyoxyl group, carboxyl bis (K6) alkylamine carbonyl, the same or different (Cl_c6) 垸 pingan 1 6) hydrazine, aniline carbonyl, contains on the ring 1 or more of the same or different people 丨 丨 "can be selected from the group of substituted anilines of γ (γ as shown below) 碁, the base (cvc6: ^ amine carbonyl group, contains 1 on the ring The same cm 丨 as above can be substituted with a substituent selected from Y (Y is shown below) to substitute the substituent (c ^ c6) alkylaminocarbonyl, oxy, amine, cyano or nitrate. ^ 4 substituents; y is a halogen atom which is the same or different, (K6) alkyl, (c2_anyl, (cvc6) alkynyl, cyclic (c3_c6) alkyl, halogenated (c "c6) Group, cyclohalogenated (C3-c6) alkyl, (CVC6) alkoxy, halogenated (Κ6) alkoxy, (cvcjalkylthio), halogenated (〇1 < 6) alkylthio, alkylsulfinyl, Halogenated ((VCJ alkylene Fluorenyl, (K6) alkanesulfonium, halogenated (C ^ CJ alkanesulfonyl, phenyl, containing halogen atoms selected from the same or different, (Ci_C6) alkyl '(C ^ C6) alkenyl, (C, _ C6) block group, ring (CrC6) group base, halogenated (C "c6) group base, ring selenization (C3_C6) element group, (cvcj group oxygen group, halogenated (c" c6) group oxygen group, ((^-(: 6) sulfonyl radicals (C, C6) sulfhydryl radicals, (C ^ Cs) sulfinylsulfenyl radicals, halogenated (C, C6) sulfinylsulfenyl radicals, (κ6) alkylsulfonium Group, halogenated (< :: 1 < 6) alkanoate group, ((^-(: 6) alkylcarbonyl group, halogenated (Ci_c6) alkylcarbonyl group, (cv -134-6) oxooxy group) 1 to 5 substituents of cc, phenol, cvc6 alkylamine carbonyl, the same or different di (cc ρ — /, 6) 丨 carbonyl, hydroxyl, amine, cyano or nitro ^ ^ ^ Π substituted phenyl, phenoxy, containing halogen atoms, halogen atoms, (CVC,) alkyl, (c2-c6) alkenyl, (Cr C6) alkynyl, ring 3 6) & group, halogenated (C i-C 6) alkyl group, ring halogenated (c 3-C 6) alkyl group, (cc ~ 6) j: oxo group, halogenated (cvcj Oxy, (Ci C6) sulfanyl group, halogenated u & ^ 1 < 6) alkylthio group, (CVC6) alkylsulfinylfluorenyl group, halogenated (eve,) alkylsulfinylfluorenyl group, (Ci_c6) alkylsulfonyl group Fluorenyl, halogenated (ci-c6) alkylsulfonyl, (cvc v 卢 宜 班 #, & 6) oxo group, halogenated (Ci-C6) alkylcarbonyl, (cvc6) oxycarbonyl, —, Leptyl, c (c, c) alkylamine carbonyl, the same or different di (—1 h); 1-5 substitutions of alkyl, hydroxy, amine, cyano or nitro ^ "To replace the original isopropyl, phenylthio, containing halogen atoms selected from the same or different, (CrC6) alkyl, (C,-c6m group, (C2_C6) alkynyl, ring · 6) Academic base, halogenated (CVC6) alkyl, cyclohalogenated (C3-C6) alkyl, (C c V Tochigan 1 6) alkoxy, halogenated (C, -C6) h group, (Cl-C6 ) Sulfur group, Ci_c6, Sulfur group, Sulfur group, C (C6) 焼 焼 rv / rvh, c 6) Alkyl sulfonium, ,,, and seven (Cl-C6) Sulfur group Fluorenyl, (Ci, c6) alkylcarbonylc6) alkylcarbonyl, (Cl-C6) alkoxycarbonyl,. (1 amine carbonyl, same or different = mono (cvc0) alkyl, ^^-1? ^^ 1 ~ CrC6) alkylaminocarbonyl, hydroxyfe, oxy or nitro substituents of phenylene Sulfofluorenyl group, containing h _ (c "c6) alkyl group selected from the same or non-n-substituted thio group, (C7-c6) storage group, (c Γ metastable atom, group, halogenated ( C "C6) alkyl, cyclic halide ^ (C3-C6) k -13 5 '(cvqm 200404764oxy, halogenated ((^-(: 6) alkoxy, (C ^ c,) alkylthio , Halogenated (Ci_c6) alkylthio, (cvc6) alkylsulfinyl, halogenated (CVC6) alkylsulfinyl, (C "C6) alkylsulfinyl, halogenated (Cl_C6) alkylsulfinyl, ((^ -(: 6) alkylcarbonyl, halogenated (cvc6) alkylcarbonyl, (Ci-c,) alkoxycarbonyl, carboxyl, mono ((: "0: 6) alkylaminecarbonyl, same or different two (Ci_c6) Alkylaminocarbonyl, hydroxy, amine, cyano or nitro substituted benzene sulfenyl fluorenyl, benzenesulfonyl sulfonyl, containing halogen atoms selected from the same or different, ( Ci-C,) alkyl, (C2-C6) alkenyl, (c2-c6) alkynyl, cyclo (C3-C6) alkyl, halogenated (Ci_c6) alkane , Cyclohalogenated (C3-C6) alkyl, (c "c6) alkyloxy, halogenated (c" c6) alkoxy, (cvc6) alkylthio, halogenated (cvcj alkylthio, (Ci_c6) alkylsulfinyl Fluorenyl, halogenated (c "c6) sulfinylfluorenyl, ((: 1 < 6) alkylsulfonyl, halogenated (CVC6) alkylsulfonyl, (C" C6) alkylcarbonyl, halogenated (Ci_c6) alkyl Carbonyl group, (CVC6) alkoxy group, carboxyl group, mono (Ci_C6) alkylamine carbonyl group, the same or different di (C ^ C6) alkylamine carbonyl group, hydroxyl group, amine group, cyano group or nitro group -5 substituted substituents of benzenesulfonyl, (C1-C6) alkylcarbonyl, halogenated (c "indenyl, phenylcarbonyl, containing a national atom selected from the same or different, (Ci- C,) alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, Ttto ((Vc6) alkyl, halogenated (c "c6) alkyl, cyclohalogenated (κ6) alkyl, (c "C6" alkyloxy, halogenated (〇1-(: 6) alkoxy, (CVC6) alkylthio, graphitized (Cl-C6) alkylthio, (C ^ Cd alkylsulfinyl sulfonyl, halogenated (Ci -CJ ^ sulfenyl, (CVC6) alkylsulfonyl, halogenated (CVc6) alkylsulfonyl, (ci-c6) alkylcarbonyl, halogenated (Ci_c6) alkyl Group, (CVC6) alkoxy group, carboxyl group, mono (Ci_c6) alkylamine carbonyl group, same or different, can be 200404764. Two of them are taken from amine group, warp group, amine group, gas group or nitro group. Mono (C * substituted phenylcarbonyl group, (CVC6) alkoxycarbonyl group, carboxyl group, amine group C1'c6) f aminofluorenyl group, the same or non-concentrated di (c "cfi) alkyl of the present amine carbonyl group , Containing halogens (C "C6) courtyard base, (C2_C6) flammable radical, (^ meaning) fast radical, cyclic halogenated (C" C6) alkyl, ring halogenated (C3_C6) which can be selected from the same and sold differently. Alkyl, (Ci_C6): oxygen, halogenated (Cl-C6) alkyloxy, (Ci ') sulfur, halogenated (c: _ alkylthio, (Ci_C6) alkylsulfinyl sulfonyl, nationalized (Ci_C6 ) Alkylsulfinyl, (1-〇6) alkylsulfinyl, halogenated (Ci_C6) alkylsulfinyl, alkylcarbonyl, halogenated (CrG) alkylcarbonyl, (CVC6) alkoxycarbonyl, 6 carboxyl, Mono (Ci-c: 6) alkylamine carbonyl, the same or different bis (c "ce) alkylamine carbonyl, hydroxyl, amine, cyano or nitro substituted aniline , Phenyl (Cl-C6) alkylamine carbonyl, contains one on the ring The above are selected from the same or different halogen atoms, (c ^ c) alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, cyclic (CVC6) alkyl, halogenated (C "C6) Radicals, ring halogenated (C3-C6) radicals, (CrC6) radicals, halogenated (C "C6) | oxy radicals, (CrCd radicals, halogenated (c" c6) radicals, (cvcd alkylene radicals) Sulfonyl, halogenated (cvc6) alkylsulfinyl, (c "C6) alkylsulfinyl, halogenated (CVCJ alkylsulfonyl, (Ci_c6) courtyard base, Shanghua ^ Plant 6) alkylcarbonyl , (Cvc6) alkoxycarbonyl, carboxyl, mono (C ^ -Cd alkylamine carbonyl, selected from the same or different bis (Ci_c6) alkylamine carbonyl, hydroxyl, amine, cyano or nitro 1- 5 substituents of substituted phenyl (C ^ CJ alkylaminocarbonyl, hydroxyl, amine, cyano or nitro 1 to 5 substituents; and -137- 200404764 γ is adjacent to the carbon on the benzene ring The atoms together are selected from the same or different oxygen atoms, sulfur atoms, or nitrogen atoms (the nitrogen atom is a hydrogen atom, (CrC6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl Or ring ((: 3 < 6) alkyl substituted) 1 to 2 heteroatoms' In (Cl-C4) alkylene group formed in the ring by 5-6}. 2. If the halosulfanilanilide derivative or the salt thereof according to item 1 of the scope of patent application, where Q is a kind of bond in which at least one of the constituent atoms is a nitrogen atom and the constituent nitrogen atom becomes A The element at the site is a carbon atom, nitrogen atom, oxygen atom, sulfur atom, or phosphorus atom with 4 to 13 members, or a halogen atom, (C ^ C6) alkyl, (C ^ C6) alkyl, ( C2-C6) alkenyl, (c2-c6) alkynyl, fluorene (C3-C7) alkyl, halogenated (CVC6) alkyl, cyclohalogenated (c3-c7) alkyl, (Ci-Cd alkoxy, halogenated (C "c6) alkyloxy, (Ci-Cd alkylthio, halogenated (c" c6) alkylthio, (Ci-CJ alkylsulfinylfluorenyl, halogenated (c "c6) alkylsulfinylfluorenyl, ( cvc6) alkylsulfonyl, halogenated (CVC6) alkylsulfonyl, phenyl, substituted phenyl containing one or more of the same or different substituents selected from Y (Y is the same as item 1), benzene Group (C ^ -Cs), a phenyl (Cl-c6) alkyl group, phenoxy group containing at least one of the same or different substituents selected from Y (Y is the same as the above description) on the ring Base, containing one or more of the same or different A substituted phenoxy group or a phenylthio group selected from the substituents of Y (γ is the same as the above description), and a substituted benzene containing one or more substituents selected from the same (or the same as those described above) which may be the same or different. Thio and phenylsulfenyl groups, containing one or more of the same or different, may be selected from -138-200404764 Y (γ is the same as the above description), and the present sulfinyl group of the substituent Benzenesulfonate, phenylsulfonyl, (Ci ') lysyl, dentate (eve,) containing the same or more than the same substituents selected from γ (γ is the same as the above description). Alkylcarbonyl, phenylcarbonyl, and uranyl, which have more than one phase: a phenylcarbonyl group selected from the substituents of Y (Y is the same as the above description), (Cl-CJ alkoxy) A carbonyl group, a carboxyl group, a mono (Ci_c6) alkylamine group, the same or different ^ "06" amine condensate, a benzene group, and one or more of the same or different on the ring are all acceptable Choose an aniline group of Y (Y is the same as the above) substituent, phenyl (C ^ C0) alkylamine carbonyl group, and the ring contains one or more of the same or different The phenyl (C 1 · c6) alkylamine carbonyl group and heterocyclic group (heterocyclic group) selected from γ (γ is the same as the above description) as a substituent can be selected from the group consisting of pyridyl and pyridine-N-oxidation. Physical, pyrimidinyl, pyrimidinyl, sangenyl, sulfanyl, tetrahydrofuranyl, thienyl, tetrahydrothienyl, tetrahydropiperanyl, tetrahydrothiopyranyl, and 11-base (Midyl, sulforilyl, hydrazone, isothiazolyl, thiadiazolyl, imidazolyl, triazolyl, stilbyl, morpholinyl), one or more of them may be the same or different At least one selected from among a substituted heterocyclic group (a heterocyclic group is the same as the above description) of a substituent of Υ (γ is the same as the above description), a substituent group substituted by a substituent of a hydroxyl group, an amino group, a cyano group, or a nitro group Is a nitrogen atom, and the element constituting a bonding site between the nitrogen atom and A is a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a 4 to 13 carbon atom. For example, the halogen compound sulfanilide derivatives or salts thereof in the scope of application for patent No. 2 in which Q is not shown by the following formula: 139-200404764 Q-7 Q-8 Q-9 Q-6Q-7 Q-8 Q-9 Q-6 {式中，G1、 同或{Where G1, or -N G2爲相 y，爲氫原子、烷基、氰_、硝基 N-R3’（式中’ 〜 呵g， 均可以的選自γ，（γ’如後述所不）之取代基的取代苯 (cvc0)院基、苯基或含有1個以上之相同或不同均 在環上含有1個以上之相同或不f γ，（Y，如後述所示）之取代基的取代苯連 以的選自γ，（γ’如後述所不）之取代基的取代苯基）、 N-OR4’（式中，r4爲氫原子、（CrC6)院基、苯基（C「C6) 烷基或在環上含有1個以上之相同或不同均可以的選自 Y’ （Y，如後述所示）之取代基的取代苯基（Ci_c6)烷 基）、N-NR3R6’（式中，R5’及R6’爲相同或不同均可以的 氫原子、苯基或含有1個以上之相同或不同均可以的途 -140- 200404764 rs, γ’（γ’如後述所示）之取代基的取代苯基，又y，及 2同時爲（C3-CJ伸烷基）或cr7r8(式中，R?及RS爲相 不同均可以的氫原子、(C「C6)烷基、(Cl-C6)烷氧 土 b基、氰基或硝基）； C舄氧原子、硫原子或N-R9(式中，R9爲氫原子、（Ci. =)烷基、苯基（Cl-C6)烷基、在環上含有丨個以上之相 同磲不同均可以的選自γ，（γ，如後述所示）之取代基的 代本基（Ci-C：6)烷基、苯基，含有i個以上之相同或 不同均可以的選自Y，（Y’如後述所示）之取代基的苯 基、雜環基（雜環基係與申請專利範圍第2項中所示相 同）、含有1個以上之相同或不同均可以的選自γ，（Υ， 如後述所示）之取代基的取代雜環基（雜環基係與上述相 同）、雜環（Ci-CJ烷基（雜環基係與上述相同）、在環上 曰有1個以上之相同或不同均可以的選自γ，（γ，如後 述所示）之取代基的取代雜環（Ci-CJ烷基（雜環基係與上 述相同）、單（CrC6)烷胺羰基、相同或不同均可以的 (C^C6)烷胺羰基、苯胺羰基，或在環上含有1個以上 之相同或不同均可以的選自Y ’（ Y ’如後述所示）之取代 基的取代苯胺羰基）； J2及J3係爲相同或不同均可以的氧原子、硫原子N-R9 (式 中，R9與上述相同）、RM-C-R11(式中R1Q及R11係爲相 同或不同均可以的氫原子、（CVCd院基、鹵化（c「c6) 烷基、（CVC6)烷氧基、鹵化（Ci-C6)烷氧基、（Ci-C6)烷 硫基、鹵化（c i - C 6)烷硫基、（c i - C 6)烷亞磺醯基、鹵化 -141- 2UU4U4764 Ok亞醯基、（cvc6)烷磺醯基、 磺醺赶 _化（c「c、衫 _、苯基（Ci-CJ烷基、在環上含有 6燒 问竣 > 個以上之：to 火不同均可以的選自γ, (γ，如後述所示 之相 取代苯基(υ6)烷基、苯基或含有丨個 取代基的 不同均可以的選自Υ’（Υ，如後述所示 之相同或 苯基）、C = 〇或c = s; 5代基的取代 J及J5係爲相同或不同均可以的C_R1、式中，卜 原子、齒素原子、(Cl_C6)烷基、鹵化(Ci_c6)产：1·爲氫 ^院氧基、齒化（Cl.c6m氧基、（c「c6)院硫兀基、、=· (h-Cs)烷硫基、（Cl_C6)烷亞磺醯基、鹵化烷亞 磺醒基、（Cl-c6m擴酸基、鹵化（Ci_c6)院擴酿基^ 基（C^C6)烷基、在環上含有丨個以上之相同或不同均 可以的選自γ’（Y’如後述所示）之取代基的苯基（c「C6) 烷基、本基.、曰有1個以上之相同或不同均可以的選自 Y’（Y如後述所示）之取代基的取代苯基或氰基）或氮 原子； J6爲氧原子、硫原子、N-R9(式中，R9與上述相同）或 R^C-RH(式中，RU及R11與上述相同）； R9與上述相同； R13及R14係爲相同或不同均可以的氫原子、鹵素原子、 (cvcj烷基、鹵化（c^cj烷基、（Ci-C6)烷氧基、鹵化 (C「C6)烷氧基、（Ci_C6)烷硫基、鹵化（C「C6)烷硫基、 (c「c6)烷亞磺醯基' _化（〇：1-(：6)烷亞磺醯基、（cvc6) 烷磺醯基、鹵化（cvC6)烷磺釀基、苯基（Ci_CJ烷基、 -142- 在^上含有1個以上之 (γ , @π |Ρ]或不同均可以的選自Υ ’ 如後述所示）之取代 基、含右 的取代苯基（Ci-C0)烷基、苯 3有1個以上之相固十_ 如後述所—门或不同均可以的選自Y，（Y， 谈遮所不）之取代基的 m to ^ 本基、雜環基（雜環基與上 相同）、含有1個以上之相 (γ, <相问或不同均可以的選自Υ， ,/臭忒所不）之取代基的取代雜環基（雜環基與上述 上2 )雜環基（C「C6)烷基（雜環基與上述相同）、在環 3有1個以上之相同或不同均可以的選自γ，（γ，如 後、GfC — ^斤示）之取代基的取代雜環基（C「C6)烷基（雜環基與 込相同）、單（CrC6)烷胺羰基、相同或不同均可以的 (胺羰基、苯胺羰基、在環上含有i個以上之 相同或不同均可以的選自Y’（Y，如後述所示）之取代基 的取代苯胺羰基或氰基； R 及R16係爲相同或不同均可以的氫原子或（cvcj院 基； x’爲選自相同或不同均可以的氫原子、鹵素原子、（C「 C6)烷基、（C2-C6)烯基、（c2-c6)炔基、環（c3-c7)烷基、 烷基、環鹵化（c3-c7)烷基、（cvc6)烷氧基、 鹵化（C「C6)烷氧基、（CVC6)烷硫基、鹵化（C「C6)烷硫 基、（C1-C6)烷亞磺醯基、鹵化（C「C6)垸亞磺醯基、（C「 c6)烷磺醯基、鹵化（Ci-C,)烷磺醯基、苯基、含有1個 以上之相同或不同均可以的运自Y (Y如後述所7K)之 取代基的取代苯基、苯氧基、含有1個以上之相同或不 同均可以的選自γ，（Y ’如後述所示）之取代基的苯氧 -143- γ,本硫基、含有1個以上之相同或不同均可以的選自 其 如後述所示）之取代基之取代苯硫基、苯亞磺醯 曰有1個以上之相同或不同均可以的選自γ，（Υ’ 如後t 〜 、 示）之取代基的取代苯亞磺醯基、苯磺醯基、 Q有 j 個以上之相同或不同均可以的選自γ ’（ γ，如後 @所不、5 、取代基的取代苯磺醯基、（Ci-C6)烷基羰基、 齒化i C1 丨元基羰基、苯基羰基，含有1個以上之相 # 同均可以的選自γ，（γ，如後述所示）之取代基的 取代苯碟帕# 擴醒基、（cvc6)烷氧基羰基、羧基、單（c「c6) 院胺樂i I _ 火巻、相同或不同均可以的（CVC：6)烷胺羰基、苯 火必’在環上含有i個以上之相同或不同均可以的選 自 γ , , 、-N G2 is a phase y, and is a hydrogen atom, an alkyl group, a cyano group, and a nitro group N-R3 '(wherein' ~ gg, may be selected from the substituents of γ, (γ 'is not described later) Substituted benzene (cvc0) radical, phenyl or substituted benzene containing 1 or more of the same or different f γ, (Y, as shown below) substituents on the ring A substituted phenyl group selected from the group consisting of γ, (γ 'is not described later), N-OR4' (wherein R4 is a hydrogen atom, a (CrC6) alkyl group, a phenyl (C "C6) alkyl group Or a substituted phenyl (Ci_c6) alkyl group selected from Y ′ (Y, as shown below) that contains one or more of the same or different substituents on the ring, N-NR3R6 '(wherein R5 'And R6' are the same or different hydrogen atom, phenyl group, or one or more of the same or different may be -140- 200404764 rs, the substitution of the substituent of γ '(γ' is shown below) Phenyl, y, and 2 are both (C3-CJ alkylene) or cr7r8 (where R? And RS are different hydrogen atoms, (C "C6) alkyl, (Cl-C6) Alkoxide b-based, cyanide Or nitro); C 舄 oxygen atom, sulfur atom or N-R9 (where R9 is a hydrogen atom, (Ci. =) Alkyl group, phenyl (Cl-C6) alkyl group, and contains more than one It may be the same or different but may be selected from the group consisting of γ, (γ, as shown below) substituted (Ci-C: 6) alkyl groups and phenyl groups, which may contain i or more of the same or different It may be selected from the group consisting of a phenyl group, a heterocyclic group (the heterocyclic group is the same as that shown in item 2 of the scope of the patent application) of Y, (Y 'is shown below), and one or more of them may be the same or different. A substituted heterocyclic group selected from the group consisting of γ, (i.e., as described later) (heterocyclic group is the same as above), heterocyclic (Ci-CJ alkyl (heterocyclic group is the same as above), A substituted heterocyclic ring (Ci-CJ alkyl (heterocyclic group is the same as above)) selected from the group consisting of γ, (γ, as shown below) which may be the same or different on the ring. (CrC6) alkylamine carbonyl, the same or different (C ^ C6) alkylamine carbonyl, aniline carbonyl, or one or more of the same or different on the ring may be selected from Y '(Y' Substituted aniline carbonyl group as shown below); J2 and J3 are the same or different oxygen atom and sulfur atom N-R9 (where R9 is the same as above), RM-C-R11 (where R1Q and R11 are the same or different hydrogen atoms, (CVCd radical, halogenated (c "c6) alkyl, (CVC6) alkoxy, halogenated (Ci-C6) alkoxy, (Ci-C6) Alkylthio, halogenated (ci-C 6) alkylthio, (ci-C 6) alkylsulfinyl, halogenated -141- 2UU4U4764 Ok fluorenyl, (cvc6) alkylsulfinyl, sulfonium (C "c, shirt_, phenyl (Ci-CJ alkyl group, containing 6 or more groups in the ring > more than one: to fire can be selected from γ, (γ, as shown below) Substituted phenyl (υ6) alkyl, phenyl, or different substituents may be selected from Υ '(Υ, the same or phenyl as shown below), C = 0 or c = s; 5 generations The substituents J and J5 of the group are the same or different C_R1. In the formula, the atom Bu, the halogen atom, the (Cl_C6) alkyl group, and the halogenated (Ci_c6) product are: 1 · is hydrogen ^ oxygen, dentified ( Cl.c6m oxygen, (c "c6) courtyard sulfur ,, = · (h-Cs) alkylthio, (Cl_C6) alkylsulfinyl, halogenated alkylsulfinyl, (Cl-c6m extended acid group, halogenated (Ci_c6) compound extended group (C ^ C6) an alkyl group, a phenyl (c "C6) alkyl group containing at least one of the same or different substituents selected from γ '(Y' as described below) on the ring, and a radical of this group. One or more substituted phenyl or cyano groups selected from the substituents of Y ′ (Y is shown below) or nitrogen atoms; J6 is an oxygen atom, a sulfur atom, and N-R9 (the formula In the formula, R9 is the same as above) or R ^ C-RH (where RU and R11 are the same as above); R9 is the same as above; R13 and R14 are the same or different hydrogen atom, halogen atom, (cvcj alkane) Group, halogenated (c ^ cj alkyl, (Ci-C6) alkoxy, halogenated (C "C6) alkoxy, (Ci_C6) alkylthio, halogenated (C" C6) alkylthio, (c "c6 ) Alkylenesulfinyl '(-: 0: 1-(: 6) Alkylenesulfinyl, (cvc6) Alkylsulfonyl, Halogenated (cvC6) Alkylsulfonyl, Phenyl (Ci_CJ alkyl, -142 -One or more of (γ, @ π | Ρ) or different can be selected from Υ ' As shown below, the substituents, right-containing substituted phenyl (Ci-C0) alkyl groups, and benzene 3 have at least one phase. As described later, the gate or different may be selected from Y, (Y, The m to ^ substituent of the substituent, the heterocyclic group (the heterocyclic group is the same as above), and the phase containing more than one phase (γ, < related or different may be selected from Υ,, / Heterosexual) Substituted heterocyclyl (heterocyclyl is the same as the above 2) heterocyclyl (C "C6) alkyl (heterocyclyl is the same as above), one or more of the ring 3 The same or different can be selected from the group consisting of substituted heterocyclic groups (C "C6) alkyl (heterocyclic groups are the same as fluorene), mono (CrC6) Alkylamine carbonyl, the same or different (amine carbonyl, aniline carbonyl, substituted aniline carbonyl containing i or more of the same or different substituents selected from Y '(Y, shown below)) Or cyano; R and R16 are the same or different hydrogen atoms or (cvcj); x 'is a hydrogen atom, halogen atom, ( C "C6) alkyl, (C2-C6) alkenyl, (c2-c6) alkynyl, cyclo (c3-c7) alkyl, alkyl, cyclohalogenated (c3-c7) alkyl, (cvc6) alkoxy Group, halogenated (C "C6) alkoxy group, (CVC6) alkylthio group, halogenated (C" C6) alkylthio group, (C1-C6) alkylsulfinylfluorenyl group, halogenated (C "C6) sulfinylfluorene (C, c6) alkanesulfonyl, halogenated (Ci-C,) alkanesulfonyl, phenyl, one or more of the same or different may be substituted by Y (Y is as described below 7K) Substituted phenyl group, phenoxy group, phenoxy group containing at least one of the same or different members selected from the group consisting of γ, (Y ′ is as described below), a thio group containing 1 More than one of which is the same or different may be selected from the group consisting of substituted phenylthio and phenylsulfinyl, which are substituted as shown below). One or more of the same or different may be selected from γ, (Υ ′ Substituted phenylsulfenyl, benzenesulfenyl, and Q of the substituents of the following t ~, can be selected from the group consisting of γ '(γ, as the following @ 所 不 、 5, substitution Substituted benzenesulfonyl, (Ci-C6) alkylcarbonyl, dentition i C1 丨 Menylcarbonyl group, phenylcarbonyl group, containing one or more phases # Substituted benzene disk # which can be selected from γ, (γ, as shown below) substituents # Awake group, (cvc6) Alkoxycarbonyl, carboxyl, mono (c "c6) amine amine i I _ fire 巻, the same or different (CVC: 6) alkyl amine carbonyl, benzene fire must contain i or more of the same on the ring Or different can be selected from γ,,, (γ’如後述所示）之取代基的取代苯胺羰基、苯^ (ci-ce)烷胺羰基，在環上含有i個以上之相同或不同 均可以的選自γ’（Y，如後述所示）之取代基的取代苯其 (CVC6)烷胺羰基、羥基、胺基、氰基或硝基之個取 代基； Υ’爲選自相同或不同均可以的氫原子、鹵素原子 」、（C c6)烷基、（c2-c6)烯基、（c2-c6)炔基、環（c3-c6)燒基 鹵化（C「c6)烷基、環鹵化（c3-c6)烷基、（Ci_c6)烷氧基 鹵化（C「C6)院氧基、d-C^)院硫基、鹵化（C^-c 6 J現ί 基、（Ci-C：6)烷亞磺醯基、鹵化（CVC6)烷亞磺醯基、 \ ^ C：6)烷磺醯基、鹵化（CVCd烷磺醯基、苯基、苯氣基 (Ci-C：6)院基羯基、鹵化（C「C6)院基鑛基、苯基幾基 (cvc6)烷氧基羰基、羧基、單（C「c6)烷胺羰基、〜 -144- 200404764 c6)烷胺羰基、苯胺羰基、羥基、胺基、氰基或硝基之 1 - 5個取代基}。 4 .如申請專利範圍第1項之鹵烷磺醯苯胺衍生物或其鹽 類，其中R1爲氟烷基，R2爲氫原子，Q如下通式所示： -N G1 G1 人J1 —/n-r b2J3 y=J5 Q-1 G1 Q-2(γ 'is shown below) The substituted aniline carbonyl and phenyl (ci-ce) alkylamine carbonyl of the substituent may be selected from γ' (Y, as described later) (CVC6) alkylamine carbonyl, hydroxyl, amine, cyano or nitro substituents; Υ 'is a hydrogen atom or a halogen atom selected from the same or different ", (C c6) alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, ring (c3-c6) halohalo (C "c6) alkyl, cyclohalo (c3-c6) alkyl, (Ci_c6) alkoxy halides (C "C6) alkoxy, dC ^) thio, halides (C ^ -c 6 J alkyl, (Ci-C: 6) alkenesulfinyl, halides ( CVC6) alkylsulfinyl, ^ C: 6) alkylsulfinyl, halogenated (CVCd alkylsulfinyl, phenyl, benzene (Ci-C: 6) alkylsulfonyl, halogenated (C "C6 ) Benzyl, phenyl phenyl (cvc6) alkoxycarbonyl, carboxyl, mono (C "c6) alkylamine carbonyl, ~ -144- 200404764 c6) alkylamine carbonyl, aniline carbonyl, hydroxyl, amine, cyano 1 to 5 substituents of nitro or nitro} 4. Haloalkane as claimed in item 1 of the scope of patent application Acyl aniline derivative type, wherein R1 is a fluoroalkyl group, R2 is a hydrogen atom, Q following general formula: -N G1 G1 human J1 - / n-r b2J3 y = J5 Q-1 G1 Q-2 R 13 (式中，G1爲氧原子； R9爲苯基烷基、在環上含有1個以上選自相同 或不同均可以的氫原子、鹵素原子、（Cl-C6)烷基、（C2-C6)烯基、（C2-C6)炔基、環（C3-C6)烷基、鹵化（<^-(：6)烷 基、環鹵化（C3-C6)烷基、（C「C6)烷氧基、鹵化（C「C6) 烷氧基、（cvc6)烷硫基、鹵化（CVC,)烷硫基、（CVC,) 烷亞磺醯基、鹵化（CVC6)烷亞磺醯基、（CVC6)烷磺醯 基、鹵化（cvc6)烷磺醯基、（c^c,)烷基羰基、鹵化（CV c6)烷基羰基、（CVC6)烷氧基羰基、羧基、單（(^-(^烷 胺羰基、二（Ci-Cd烷胺羰基、羥基、胺基、氰基或硝 基的取代基之取代苯基（Ci-Cd烷基、苯基、含有1-5個 選自相同或不同均可以的氫原子、鹵素原子、（c^c,) 烷基、（c2-c6)烯基、（c2-c6)炔基、環（c3-c6)烷基、鹵 化（CVC,)烷基、環鹵化（C3-C6)烷基、（CVC6)烷氧基、 鹵化（c「c6)烷氧基、（c「c6)烷硫基、鹵化（c「c6)烷硫 基、（Ci-Cd烷亞磺醯基、鹵化（CVC6)烷亞磺醯基、（c^ -145- 2UU4U4/b4 6 ^ fen 5¾ ^ - 土 ®化（(^-〇6)院礦釀基、（Ci-Cs)燒基鑛 幽化（C ^ ^C6)燒基羰基、（Cl-C6)烷氧基羰基、羧基 (c C 、1 6)院胺鑛基、二（Cl-C6)烷胺羰基、羥基、胺 w β _硝基的取代基之取代苯基、吡啶基、含有1 k自相同或不同均可以的鹵素原子、（C1_C6)烷 鹵化（C r \ ^ ^ rC6)J：兀基、（Ci_c6)烷氧基或鹵化（Ci-C6：^ 的取伴背— R $之取代吡啶基、嘧啶基、或含有1個以上 相同或不同均可以的鹵素原子、（Ci-C6)烷基、鹵化 6)《元基、（Ci-C：6)院氧基或鹵化d-Cd院氧基的取 之取代嘧啶基）； Rl3爲苯基（Ci-CJ烷基、在環上含有1個以上選自 或不同均可以的氫原子、鹵素原子、（Cl-C6)烷基、 c6)烯基、（c2-c6)炔基、環（c3-c6)烷基、鹵化 基、環鹵化（c3-c6)烷基、（cvc6)烷氧基、鹵化（c 烷氧基、（CVC,)烷硫基、鹵化（CVC,)烷硫基、（c 烷亞磺醯基、鹵化（c「c6)烷亞磺醯基、（CVCdj^ 基、鹵化（c「c6)烷磺醯基、（CVC6)烷基羰基、鹵化 C6)烷基羰基、（cvc6)烷氧基羰基、羧基、單（cvc 胺羰基、二（CrCJ烷胺羰基、羥基、胺基、氰基 基的取代基之取代苯基（Cl~C6)院基、本基、含有1. 選自相同或不同均可以的氫原子、鹵素原子、（C 烷基、（C2-C6)烯基、（C2-C6)炔基、環（(：3-(：6)烷_ 化院基、環鹵化（C3-C6)院基、（CrC6)院氧 鹵化（c i - C 6)院氧基、（C 1 - C 6)院硫基、鹵化（c I - c 6) 基、 、單 基、 個以 基、 氧基 選自 ((V 代基 相同 (C 2 - 、）院 1，C6) 1，C6) 磺醯 (C〖- :6)烷 或硝 ，5個 1、C6) 、鹵 基、 燒硫 -146- 200404764 基、（cvc6)烷亞磺醯基、鹵化（cvc：6)烷亞磺酸基、 cj烷磺醯基、鹵化（cvc：6)烷磺醯基、（c「c0)烷基壞其「 鹵化基、（C^-Cs)院氧基擬基、约* 瘦基、單 (C 1 - c 6)院胺鑛基、一（C i - C 6)院胺鑛基、裡基、γ _ 妆基、 氰基或硝基的取代基的取代苯基、毗啶基、含 、 、 1個以 上選自相同或不同均可以的鹵素原子、 6 J k 基、 鹵化（cvc6)烷基、（cvc6)烷氧基或鹵化（C「c 6 J抚氧_ 的取代基之取代吡啶基、嘧啶基、或含有1個以 < 上選自 相同或不同均可以的取代基的鹵素原子、（C L - c 6化_、 c6)烷氧_R 13 (wherein G1 is an oxygen atom; R9 is a phenylalkyl group, and the ring contains one or more hydrogen atoms, halogen atoms, (Cl-C6) alkyl groups, or (C2- C6) alkenyl, (C2-C6) alkynyl, cyclo (C3-C6) alkyl, halogenated (< ^-(: 6) alkyl, cyclohalogenated (C3-C6) alkyl, (C 「C6) Alkoxy, halogenated (C "C6) alkoxy, (cvc6) alkylthio, halogenated (CVC,) alkylthio, (CVC,) alkylsulfinyl, halogenated (CVC6) alkylsulfinyl, (CVC6) alkylsulfonyl, halogenated (cvc6) alkylsulfonyl, (c ^ c,) alkylcarbonyl, halogenated (CV c6) alkylcarbonyl, (CVC6) alkoxycarbonyl, carboxyl, ((^ -(^ Alkylamine carbonyl, di (Ci-Cd alkylamine carbonyl, substituted hydroxy, amine, cyano or nitro substituted phenyl (Ci-Cd alkyl, phenyl, containing 1-5 selected from The same or different hydrogen atom, halogen atom, (c ^ c,) alkyl, (c2-c6) alkenyl, (c2-c6) alkynyl, cyclo (c3-c6) alkyl, halogenated (CVC, ) Alkyl, cyclohalogenated (C3-C6) alkyl, (CVC6) alkoxy, halogenated (c "c6) alkoxy, (c" c6) alkylthio, halogenated (c "c6) alkane Sulfur, (Ci-Cd alkylsulfinyl sulfonyl, halogenated (CVC6) alkylsulfinyl sulfinyl, (c ^ -145- 2UU4U4 / b4 6 ^ fen 5¾ ^-® ((^ -〇6) Fermentation base, (Ci-Cs) alkynyl mineralization (C ^^ C6) alkynylcarbonyl, (Cl-C6) alkoxycarbonyl, carboxyl (c C, 16) amine amine, di (Cl- C6) Alkylamine carbonyl, hydroxyl, amine w β _nitro substituents substituted phenyl, pyridyl, halogen atoms containing 1 k from the same or different, (C1_C6) alkyl halide (C r \ ^ ^ rC6 ) J: Carboxyl, (Ci_c6) alkoxy or halogenated (Ci-C6: ^ 's companion — R $ is substituted pyridyl, pyrimidinyl, or contains one or more halogen atoms which may be the same or different, ( Ci-C6) alkyl, halogenated 6) "Mid radical, (Ci-C: 6) substituted oxygen or halogenated d-Cd substituted oxygen substituted pyrimidyl); Rl3 is phenyl (Ci-CJ alkyl Contains one or more hydrogen atoms, halogen atoms, (Cl-C6) alkyl, c6) alkenyl, (c2-c6) alkynyl, and ring (c3-c6) alkyl, which may be selected from the group consisting of or different from the ring. , Halogenated, cyclohalogenated (c3-c6) alkyl, (cvc6) alkoxy, halogenated (c alkoxy, (CVC, ) Alkylthio, halogenated (CVC,) alkylthio, (c alkylsulfinyl fluorenyl, halogenated (c "c6) alkylsulfinyl fluorenyl, (CVCdj ^, halogenated (c" c6) alkylsulfinyl sulfonyl, (CVC6) alkylcarbonyl, halogenated C6) alkylcarbonyl, (cvc6) alkoxycarbonyl, carboxyl, mono (cvc amine carbonyl, bis (CrCJ alkylamine carbonyl, hydroxyl, amine, cyano) substituents Phenyl (Cl ~ C6) radical, base, containing 1. Selected from the same or different hydrogen atoms, halogen atoms, (C alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl , Cyclic ((: 3-(: 6) alkane_chemical radical, ring halogenated (C3-C6) radical, (CrC6) oxyhalogenated (ci-C 6) radical, (C 1-C 6) Sulfuryl, halogenated (c I-c 6),, mono, alkoxy, and oxy are selected from ((V-substituted groups are the same (C 2-,)) 1, C6) 1, C6) sulfonium ( C 〖-: 6) Alkane or nitrate, five 1, 1, C6), halo, sulfur-sulfur-146-200404764, (cvc6) alkanesulfinyl, halogenated (cvc: 6) alkanesulfinyl, cj Alkylsulfonyl groups, halogenated (cvc: 6) alkylsulfonyl groups, (c "c0) alkyl groups, their" halogenated groups, (C ^ -Cs) oxoalkyl groups, about * Lean, mono (C 1-c 6) amine-based, mono (C i-C 6) amine-based, aryl, γ _ aryl, cyano or nitro substituted phenyl, Pyridinyl, containing, or more than one selected from the same or different halogen atoms, 6 J k groups, halogenated (cvc6) alkyl, (cvc6) alkoxy, or halogenated (C, c 6 J, oxygen_ A substituted pyridyl group, a pyrimidinyl group, or a halogen atom containing one or more substituents selected from the same or different from the above, (CL-c 6-, c6) alkoxy- 鹵化（CVC6)烷基、（cvc6)烷氧基或鹵化（c 的取代嘧啶基）； A爲（Ci-C,)伸烷基，或含有1個以上選自相同或不^ 1同均 可以的鹵素原子、羥基、（K6)烷氧基、（C c、岭 6 j抚氣 基羰基或氰基的取代基之（Ci-CJ伸烷基； 爲 G爲氧原子、或N-OR4(式中，R4爲（C「C6)烷基）， 〇或1之整數； X爲1-2個選自相同或不同均可以的氫原子或 基之取代基。 5 · —種除草劑，其包括如申請專利車E圍第1 - 4項中任一項 之鹵烷磺醯苯胺衍生物或其鹽類作爲有效成分。 6 · —種使用除草劑之方法，其係在土壤或植物上處理申請 專利範圍第5項之除草劑的有效量。 -147- 200404764 柒、指定代表圖： (一） 本案指定代表圖為：第（）圖。 (二) 本代表圖之元件代表符號簡單說明:Halogenated (CVC6) alkyl, (cvc6) alkoxy or halogenated (c's substituted pyrimidinyl); A is (Ci-C,) alkylene, or contains more than one selected from the same or not ^ 1 A halogen atom, a hydroxyl group, a (K6) alkoxy group, a (C c, a ridge 6 j, a carbonyl group, or a cyano substituent (Ci-CJ alkylene; G is an oxygen atom, or N-OR4 ( In the formula, R4 is (C "C6) alkyl), an integer of 0 or 1, and X is a substituent selected from 1-2 hydrogen atoms or groups which may be the same or different. 5 ·-a herbicide, Including as an active ingredient a halosulfonamide derivative or a salt thereof as described in any one of items 1 to 4 of the patent application vehicle E. 6-A method for using a herbicide, which is treated on soil or plants The effective amount of the herbicide in the scope of the patent application item 5. -147- 200404764 柒. Designated representative map: (1) The designated representative map in this case is: (). (II) The representative symbols of the representative map are simply explained: 捌、本案若有化學通式時，請揭示最能顯示發明特徵的化學 通式：捌 If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention:
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