TW585849B - Aminoacetonitrile derivative, agricultural and horticultural insecticide composition containing the same - Google Patents

Aminoacetonitrile derivative, agricultural and horticultural insecticide composition containing the same Download PDF

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Publication number
TW585849B
TW585849B TW088106732A TW88106732A TW585849B TW 585849 B TW585849 B TW 585849B TW 088106732 A TW088106732 A TW 088106732A TW 88106732 A TW88106732 A TW 88106732A TW 585849 B TW585849 B TW 585849B
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Taiwan
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group
hhh
hydrogen atom
halo
alkyl
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TW088106732A
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Nobuharu Andoh
Osamu Sanpei
Kazuyuki Sakata
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Nihon Nohyaku Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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Description

585849 經濟部智慧財產局員工消費合作社印製 A7 B7 五、發明說明（^ ) 發 明 背 景 發 明 之 領 域 本 發 明 傺 關 於 式 (I )之胺基乙腈衍生物以及以該衍生 物 為 活 性 成 分 之 農 園 藝用殺 蟲劑。 本 發 明 傺 關 於該殺蟲 劑 的 使 用 方 法 〇 關 技 m 之 說 明 ： 曰 本 專 利 特 公 平 9- 4 8 7 5 G號（1 9 9 7 )掲示苯基烷酸醯胺 衍 生 物 做 為 農 園 藝 殺 蟲劑， 曰本專 利 特 公 平 6- 220004號 (1 99 4)掲 示 以 N - 苯 基 乙胺基 腈類做 為 生 産 用 中 間體，而 曰 本 專 利 特 公 平 6- 2 6 3 7 3 1 號 (1994) 特 公 平 6 一 2 7 1 5 3 7 號 (1 9 9 4 )及 特 公 平 7 - 2 5 2 2 2 2 號 (1995) 掲 示 有 類 似 本發明式 (I )之胺基乙腈衍生物之化合物。 發 1 之 概 要 基 於 開 發 新 穎 之 農 園藝殺 蟲劑， 本 發 明 者 Μ iiCC 由潛心研 究 結 果 發 現 式 (1)之胺基乙腈衍生物為新穎之化合物並 具 有 顯 著 之 殺 蟲 效 果 ，遽而 完成本 發 明 〇 發 星 之 詳 細 説 明 本發明偽關於式（1 )之胺基乙腈衍生物以及包含該衍 生物為活性成分之農園藝用殺蟲劑：
Ar*-(Q)d-
o = C
CN
R I C
R (請先閱讀背面之注意事項再填寫本頁) R7 I 一 W- (C)to -Ar2 (I)
8 I R (式中Ar 1和Ar 2傺相同或各異分別代表苯基； 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（ &gt; 鹵 至少具有一個相同或不同之取代苯基係選自鹵素原子 硝基，氡基，院基，_代（^1-〇6院基， l-C6烷氧基，鹵代Ci-Ce烷氧基，C2-Ce烯基， 代C2*~Ce嫌基，C2-C6炔基，C3-C6環院基， C 2 - c 6烯氧基，鹵代C 2 - C 6烯氣基，C i - C 6烷硫基 ，鹵代Ci 院硫基，Ci -Ce焼礙醒氧基，Ci-Cb 烷亞硫醯基，C i - C 6烷磺醯基，鹵代C i - C 6烷磺醯基 ，C 2 - C 6烯硫基，鹵代C 2 - c 6烯硫基，C 2 - c 6烯亞 醯基，鹵代c2 -C6烯亞硫醯基，C2 -c6烯磺醯基， 硫 鹵代C 2 - C 6烯磺醯基， 胺 C 6烷胺基， - C 1 - C 6 院
經濟部智慧財產局員工消費合作社印制衣 基，C 1 - C 6烷磺醯胺基，鹵代C i - C 6烷磺醯胺基， Ci-C6烷羰基，鹵代Ci-Cs烷羰基，Ci-Ce烷氧羰 基，苯基，一取代苯基具有至少一個相同或不同之取代 基傺選自_素原子，氡基，硝基，Ci-C6烷基，鹵代 Ci-C6烷基，Ci-Ce烷氣基，鹵代Ci-Ce烷氧基， (^-“烷硫基，鹵代Ci -C6烷硫基，Ci-Ce烷亞硫 醯基，鹵代C i - C 6烷亞硫醯基，C i - C 6烷磺醯基，及 鹵代Ci -C6烷磺醯基所構成之基， 苯氣基，一取代苯氧基在其環上至少具有一個相同或 不同之取代基俗選自鹵素原子，氡基，硝基，C i - C e 院基，鹵代Ci_C6院基，Ci-C6院氧基，鹵代Ci-C6 院氧基，Ci_C6院硫基，鹵代Ci-C6院硫基，Ci-Ce 烷亞硫醯基，鹵代Ci-Ce烷亞磺醯基，Ci-Ce烷磺醯 基以及_代（：1 -Cs烷磺醯基所組成之基， 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 經濟部智慧財產局員工消費合作社印製 585849 A7 _B7_ 五、發明說明（4 ) 苯乙炔基， 被取代之苯乙炔基在其環上至少具有一個相同或不同 之取代基傺選自鹵素原子，氰基，硝基，C i - C 6烷基 ，鹵代Ci-Cs烷基，Ci-Ce烷氧基，鹵代“-“烷 氧基，Ci-C6烷硫基，鹵代Ci-Ce烷硫基，Ci-Cs 烷亞硫醯基，鹵代Ci-C6烷亞硫醯基，Ci-Ce烷磺醯 基以及鹵代Ci -C6烷磺醯基所組成之基， 毗啶氧基以及 一取代之吡啶氧基在其環上至少具有一個相同或各異 之取代基係選自鹵素原子，氰基，硝基，（^-(：6烷基 ,齒代Ci-Cs院基，Ci_C6院氣基，齒代Ci_C6院 氧基，Ci -Cs焼硫基，1¾代Ci-Ce；院硫基，Ci-Cs 烷亞硫醯基，鹵代Ci -Ce烷亞硫醯基，Ci -C6烷磺醯 基以及鹵代C i - C 6烷磺醯基所組成之基； 毗啶基； 取代之吡啶基在其環上至少具有一個相同或不同之取 代基係選自鹵素原子，氰基，硝基，Ci-Ce烷基，鹵 代Ci-Cs院基，Ci -Ce?院氧基，鹵代Ci_C6院氧基， C 2 - C 6烯氧基，鹵代C 2 - C 6烯氣基，C i - C 6烷硫基， 鹵代Ci -C6烷硫基，Ci -C6烷亞硫醯基，鹵代Ci -C6 烷亞硫醯基，C2-C6烯硫基，鹵代c2-c6烯硫基， C2 -C6烯亞硫醯基，鹵代C2 -Ce烯亞硫醯基，Ci -ce 烷磺醯基，鹵代（：1-(：6烷磺醯基，鹵代c2-c6烯磺醯 基，鹵代C 2 - C 6烯磺醯基C i - C 6烷胺基及二-C 1 - C 6烷胺基 所組成之基； _ ^ 本紙張尺度適用中國國家標準（CNS)A4規格（210 x 297公釐） ----------------------訂---------線 — · (請先閱讀背面之注意事項再填寫本頁) 1---------------------- 585849 A7 B7 經濟部智慧財產局員工消費合作杜印製 五、發明說明（4 萘基；或 取代之萘基在環上至少具有一個相同或不同之取代基 係選自鹵素原子，氰基，硝基，Ci-Cs烷基，鹵代 Ci-Cs院基，Ci-Cs院氧基，_RCi-C6院氧基， C 2 - C e烯氣基，鹵代C 2 - C 6烯氧基，C i _ C 6烷硫基， 鹵代c 1 - C e烷硫基，C i - C 6烷亞硫醯基，鹵代C i - C 6 烷亞硫醯基，Ci-Ce烷磺醯基，鹵代（^-(：6烷磺醯基 ，C2~*C6傭硫基，S代C2-C6稀硫基，C2-C6稀亞 硫醯基，鹵代C2-Ce烯亞硫醯基，〇2-(：6烯磺醯基， 鹵代 C 6烯磺醯基，C i 胺基所組成之基； Q代表以下之基 R1 一 C 一 6烷胺基及二-C i - C 6烷 R2 (式中R1和R2可相同或各異分別代表氫原子，鹵素原 子，Ci_C6院基，鹵代Ci-C6院基，Ci -Ce;院氧基， I®代Ci -C6院氧基，C3 環院基或取代之C3 -C6 環烷基至少具有一個相同或不同之取代基係選自鹵素原 子及Ci -C6烷基，而R1和R2傺相接代表在其鏈上至少 有一取代基偽選自鹵素原子，C i - C 6烷基和C i - C 6烷 氣基所構成之基），-CH=CH-或- CsC-，d為0或1之 整數； R 3代表氫原子， 烷基，鹵代 烷基， ----------------------訂---------I J (請先閱讀背面之注咅心事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7_ 五、發明說明（厂） 氰代c i - C S烷基，c i - C e烷硫基，鹵代C i - C 6烷硫 基，C2-C6稀基或C2-C6稀基； (請先閱讀背面之注咅心事項再填寫本頁) R 4 , R 5 , R 6 , R7和可相同或各異各自代表氫原子 ，鹵素，Ci-Cs烷基，鹵代Ci-Ce烷基，C3-C6環 烷基或取代之C 3 - C 6璟烷基至少具有一相同或不同之 取代基偽選鹵素原子及（：1_ -Cs烷基，苯基所組成之基 或取代之苯基至少具有一個相同或不同之取代基係選自 鹵素原子，硝基，氰基，C i - C 6烷基，鹵代C i - C 6烷 基，Ci-Ce烷氧基，鹵代Ci_C6烷氧基，Ci-Ce烷 硫基，鹵代（^-(^烷硫基，Ci-Cs烷亞硫醯基，鹵代 Ci -C6烷亞硫醯基，Ci -C6烷磺醯基，鹵代Ci -Ce 烷磺醯基，C i - C 6烷胺基和二-C i - C e烷胺基所構成之 基，而R 4和R 5傺一起形成為C 1 - C 6鏈烯基； W為- 0_，-S-，- S〇2 -或- N(R9 )-(式中R9代表氫原 子或Ci-Ce烷基），而 a和b像相同或各異為0或1至4之整數））； 經濟部智慧財產局員工消費合作社印製 在本發明中，式（I )之胺基乙腈衍生物最佳之取代基 包含例如Ar 1和Ar 2作為取代基用之苯基，鹵素原子， 鹵代C i - C 6烷基和在A r 1和A r 2環上做為取代基之鹵 代C丄-C 6烷氣基，R 1 ，R 2，R a , R 5和R e作為取代 基用之氫原子，R4作為取代基用iCi-Ce烷基，Q作 為取代基用之- CH2 -，W作為取代基用之- 0- ,而a宜 為1之整數而b最好為0。 本發明式（I )之胺基乙腈衍生物含有立體異構物之化 一 7 - 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7_五、發明說明（b ) 合物，同樣本發明亦含有此立體異構物。 本發明式（I )之胺基乙腈衍生物，例如可由以下之製 法加以製造。 onnc \J/ Λ :— c I ί
I W — (C) b-Ar2I (VII) M-CN (VI) 3-NH2 (V) CN R5 R7 I I I HN-C-(C)a-W- (〇,-Αγ = la I I I R3 R4 Re R8 (IV) (請先閱讀背面之注意事項再填寫本頁) 0II Ar1- (Q) d— C，Hal (III) (IV) 或
0II Ar1- (Q) d- C-OH
〇 CN R8 R7II I I I Ar1- (Q) d- C-N-C- (C) .-W- (C) b-Ar2III I (I) A r 1，A r 2， 代表鹼金屬原 經濟部智慧財產局員工消費合作社印製 (II) (式中R3，R4，RS，R6，R7，R8 Q, W, a, b及d傺同以上所述者一樣， 子，而Hal代表鹵素原子） 1·式（IV)—►式（I)
式（I)之胺基乙腈衍生物俗在鹼（如三乙胺，吡啶等） 之存在下令式（IV)之胺基乙腈衍生物與式（III)之醯基 _反應而製造。式（I)之胺基乙腈衍生物則使用縮合劑 (如二璟己基磺二亞醯胺，2 -氯-卜甲基吡啶碘等）令式 (IV)之胺基乙腈與式（II)之酸縮合反應而製造。式（II -8 - 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（7 ) 之酸類可由習知方法製造（如，J. Org· Chem· 763， (請先閱讀背面之注意事項再填寫本頁) 1948, Organic Synthesis coll.,Vol. 1,436, J.Org. Chew. 763, 1948, Organic Synthesis Coll.,Vol. 1, 336, Beilsteins Handbuch 9, 573， Beilsteins
Handbuch 9，63 3等）0 2 ·式（V I I ) ~►式（I V ) 式（IV)之胺基乙腈，例如可令式（VII)之羰基化合物 與式（VI)之金屬氡化物（如，氰化鈉，氰化鉀等）和與式 (V)之胺類反應而製造。可使用有機氰化物類如三甲基 甲矽烷腈和丙酮偕醇腈做為CN源。此種反應乃為習知之
Strecker反應方法（例如，Formation of C-C Bonds Vol· 1, Georg Τ h i e ηι e Publishers 1 9 7 3 , Organic Synthesis Coll. Vo 1 . ,3, 88^ )0 式（VII)之羰基化合物，例如可由以下之製法加以製 造。
0 R5 R7 BASE II I I ,ντη R4-C- (C) * —L + W，-(C)b-Ar2--一^^ (Vli, 經濟部智慧財產局員工消費合作社印製
I I
Re Re (VIII-1) (ΙΧΊ) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五
R — c — R說 *明04發 R w +
I L- (C)b-Ar2I (VII) (VIII-2) (IX-2) 經濟部智慧財產局員工消費合作社印製 RO R5I IR4-C- (C) .-L+ W，-I IRO Re (X-l)RO R5I IR4-C- (C).-W1 +I IRO Re (X-2)OH R5I IR4-CH- (C).-L +IRe (XI-1)OH R5I IR4-CH-(C).-r +IRe (XI-2)
»—-, e ••I c I R
Γ A (ix-1) R7I L- (C)b-Ar2I R8 (IX-2) R7I Wf - (C)b-Ar2I R8 (IX-1) R7I L- (C)b-Ar2I R8 (IX-2)
BASE RO R5 R7 I I I l-C- (C)a-Wr- (C)b-Ar2 I I I RO Re Re (XII)
ACID (VII) OXIDATION (請先閱讀背面之注意事項再填寫本頁)
BASE
OH R5I I
I -CH- (C) rW，一 C) b-Ar2I I Re R8 (XIII) .10· 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（9 ) 式中 R3， R4， R5, R6， R7， R8，Arl，Ar2， (請先閱讀背面之注音？事項再填寫本頁) a及b偽如以上所述者相同之意義，L代表殘基如鹵素原 子，甲基磺醯氧基或對甲基苯磺醯氧基，為0H，SH_ NHR9 (其中R9如同以上所述之相同意義，Rs為Ci-Ce 烷基可相同或各異代表（^1 -C4烯基，或Rs —起形成 Cl - C4嫌基。 式（VII)之羰基化合物，例如可令具有殘基L之式（VIII -1)化合物在鹼的存在下與式（IX-1)之化合物反應而製造。 同樣，式（VII)之羰基化合物亦可由式（VIII-2)之化 合物與式（IX-2)之化合物反應而製造。 經濟部智慧財產局員工消費合作社印製 再者，式（VII)之羰基化合物可令式（V-1)之化合物其 羰基以乙縮醛，縮酮等形式被保護在酸性條件下與式（1 X - 1)之化合物反應所衍生之式（XII)之化合物經由脫保護 反應而製造。同樣，式（XII)之化合物可令式（X-2)之化 合物與式（IX-2)之化合物反應而製造。又，式（VII)之 羰基化合物可令式（XI-1)之醇化合物使用適當之氧化劑 (例如，過錳酸鉀等）與式（IX-1)之化合物反應所衍生之 式（XIII)化合物經由氧化而製造。同樣式（XIII)之化合 物可令式（X卜2)之醇化合物與式（IX-2)之化合物反應而 製造。 本發明典型之式U)胺基乙腈化合物係由表1，2及3 所示。 R7 I W-(C)b-Ar2 I R8 0 CN Η5 II I I C-N-C-(C), II I R3 R4 Re 式（1)
Ar1 -(Q)&lt; -11- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 經濟部智慧財產局員工消費合作社印製
A7 ____B7___ 五、發明說明（…） 表1 (Re = RT = R8 = Hj Qzz-ciR1) (R2)-, d=l，b=0 (已有表逑者即例如
No· Arl Ar2 R2 R3 r R5 W a 1 Ph Ph (CH2 )2 H CH3 H 0 1 2 Ph 4-Cl-Ph Η 1 H H ch3 H 0 1 3 Ph 4-Cl-Ph (CHa)2 H ch3 H 0 1 4 Ph 4-CFa-Ph H H H ch3 H 0 . 1 5 Ph 4-CHF2〇-Ph H H H ch3 H 0 1 6 Ph 4-CF3〇-Ph H H H ch3 H 0 1 7 Ph 4-CF3S-Ph H H H ch3 H 0 1 8 Ph 4-CF3SO2- Ph H H H ch3 H 0 1 9 Ph 4-Cl-Ph CH30 H H ch3 H 0 1 10 2-Cl-Ph 2-Cl-Ph H H H ch3 H 0 4 11 2-Cl-Ph 4-Cl-Ph H H H &lt; ch3 H 0 2 12 2-Cl-Ph 4-Cl-Ph H H H H H 0 U* I 1 13 2-Cl-Ph 4-Cl-Ph H H H CH3 H 0 1 14 2-Cl-Ph 4-Cl-Ph H H H ch3 CH3 0 1 15 2-Cl-Ph 4-Cl-Ph H H H ch3 ch3 0 1 16 2-Cl-Ph 4-Cl-Ph H H H ch3 0 1 17 2-Cl-Ph 4-Cl-Ph H H H ch3 n-CaH? 0 1 18 2-Cl-Ph 4-Cl-Ph H H H ch3 n~C4Hg 0 1 19 2-Cl-Ph 4-Cl-Ph H H H ch3 Π-ΟλΗθ 0 1 -12- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（ 表一L (續） 經濟部智慧財產局員工消費合作社印製 ίο· Ar1 Ar2 20 2-Cl-Ph 4-Cl-Ph 21 2-Cl-Ph 4-Cl-Ph 22 2-Cl-Ph 4-Cl-Ph 23 2-Cl-Ph 4-Cl-Ph 24 2-Cl-Ph 4-Cl-Ph 25 2-Cl-Ph 4-Cl-Ph 26 2-Cl-Ph 4-Cl-Ph 27 2-Cl-Ph 4-Cl-Ph 28 2-Cl-Ph 4-Cl-Ph 29 2-Cl-Ph 4-Cl-Ph 30 2-Cl-Ph 4-Cl-Ph 31 2-Cl-Ph 4-CFa-Ph 32 2-Cl-Ph 4-CF3-Ph 33 2-Cl-Ph 4-CF3〇-Ph 34 2-Cl-Ph 4-CHF2〇-Ph 35 2-Cl-Ph 4-CF3S-Fh 36 2-Cl-Ph 4-CF3S〇2-Ph 37 2-F-Ph 4-CF30-Ph 38 2-F-Ph 4-CHF2〇-Ph 39 2 + Ph 4-CF3S-Ph 40 2-F-Ph 4-CF3S〇2-Ph 41 2-F-Ph 4-Cl-Ph R1 Η Η Η Η Η Η Η R2 R3 R4 R5 CH3 C2H5 η~〇3Η7 i-C3H7 C-C3H5 t-C4H9
CHa C2H5 11-C4H9 CH2C=CH
H
H •13- Η (CH2)4 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 CH3 CHa ch3 CHa CH3 CHa CH3
H
H
H
H (請先閱讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7B7 經濟部智慧財產局員工消費合作社印製 五、發明說明（^) (纊）
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 42 2-F-Ph 4-Cl-Ph (CH 2)2 H ch3 H 0 1 43 2-F-Ph 4-CFa-Ph H H H ch3 H 0 1 44 3-Cl-Ph 4-Cl-Ph H H H ch3 CHa 0 1 45 3-Cl-Ph 4-Cl-Ph H H H ch3 CHa 0 1 46 3-Cl-Ph 4-Cl-Ph H H H ch3 n-CaH? 0 . 1 47 3-Cl-Ph 4-Cl-Ph H H H ch3 n-C3H7 0 1 48 3-Cl-Ph 4-Cl-Ph H H H c2h5 H 0 1 49 3-Cl-Ph 4-Cl-Ph H H H ch3 H 0 1 50 3-Cl-Ph 4-Cl-Ph H H H CHa H 0 4 51 3-Cl-Ph 4-Cl-Ph H H H n-C3H7 H 0 1 52 3-Cl-Ph 4-Cl-Ph H H H 1-C3H7 H 0 1 53 3-Cl-Ph 4-Cl-Ph H H H c~C 3H5 H 0 1 54 3-Cl-Ph 4-Cl-Ph H H H t_C4H9 H 0 1 55 3-Cl-Ph 4-Cl-Ph H H H (CH2)4 0 1 56 3-Cl-Ph 4-Cl-Ph (CH 2)2 H CH3 H 0 1 57 4-Cl-Ph Ph H H H CHa H 0 1 58 4-Cl-Ph Ph H H H ch3 H s 1 59 4-Cl-Ph Ph H H H CHa H S〇2 1 60 4-Cl-Ph 2-Cl-Ph H H H CH3 ' H 0 1 61 4-Cl-Ph 2-Cl-Ph H H H CHa H 0 4 62 4-Cl-Ph 3-Cl-Ph H H H CH3 H 0 1 63 4-Cl-Ph 4-Cl-Ph H H H H H 0 1 _14_ --------訂---------線— · (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格，、公釐） 585849 A7 B7 五、發明說明（〇 查一L(纊
No.
Ar1
Ar5 R1 R2 R3 R5 經濟部智慧財產局員工消費合作社印製 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph. 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph 4-Cl-Ph H CH：
H H
H H H H H H H H H H
H CH3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 ch3 C2H5 n-CsH? i-CaHr C-C3H5 t-C4H9 CF3 H CH3 C2H5 H CH2 .15· 本紙張尺度適用中國國家標準（CNS)A4規格uiu x 297公釐）
H H H H H CH3 η~〇3Η7 n-C^Hg CF3 H H H H H (CH2)4 CH3 1—
n-C4H9 CH2C = CH H CH3 ch3 CHs ch2 b=l (請先閱讀背面之注意事項再填寫本頁) -線· 585849 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明說明（^ ) 虹（續）
No· Ar* Ar2 Rl R2 R3 R4 R5 W a 85 4-Cl-Ph 4-Cl-Ph ί-03Ητ H H CH3 H 0 1 86 4-Cl-Ph 4-Cl-Ph I-CsHt H H ch3 H 0 1 87 4-Cl-Ph 4-Cl-Ph CFa H H ch3 H 0 1 88 4-Cl-Ph 4-Cl-Ph (CH2 )2 H ch3 H 0 1 89 4-Cl-Ph 4-Cl-Ph (CH2)3 H ch3 H 0 . 1 90 4-Cl-Ph 4-Cl-Ph (CH2)4 H ch3 H 0 1 91 4-Cl-Ph 4-Cl-Ph F F H ch3 H 0 1 92 4-Cl-Ph 4+Ph H H H ch3 H 0 1 93 4-Cl-Ph 4-Br-Ph H H H ch3 H 0 1 94 4-Cl-Ph 4-F-Ph H H H ch3 H 0 1 95 4-Cl-Ph 3-CF3-Ph H H H ch3 H 0 1 96 4-Cl-Ph 4-CFa-Ph H H H ch3 H 0 1 97 4-Cl-Ph 4-C2F5-Ph H H H ch3 H 0 1 98 4-Cl-Ph 4-i-C3F7-Ph H H H ch3 H 0 1 99 4-Cl-Ph 4-CFa-Ph (CH2)2 H ch3 H 0 1 100 4 - cr-Ph 4~n~C3F7&quot;Ph H H H ch3 H 0 1 101 4-Cl-Ph 4-CHa-Ph H H H ch3 H 0 - 1 102 4-Cl-Ph 4~t~C4H9_Ph H H H ch3 H 0 1 103 4-Cl-Ph 4-(t-C4H9 H H H ch3 H 0 1 -C^C)~Ph 104 4-Cl-Ph 4-CH3〇-Ph H H H ch3 H 0 1 105 4-Cl-Fh 4-CF3〇-Ph H H H ch3 H 0 1 (請先閱讀背面之注意事項再填寫本頁) --線· ]β 本紙張尺度適用中國國家標準（CNS)A4規格（2川χ W7公釐） 585849 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明說明（W ) (續）
No· Ar丨 Ar2 Rl R2 R3 R4 R5 W a 106 4-Cl-Ph 4-CHFz〇-Ph H H H ch3 H 0 1 107 4-Cl-Ph 4-CF3S〇2-Ph H H H ch3 H 0 1 108 4-Cl-Ph 4-CH3S-Ph H H H ch3 H 0 1 109 4-Cl-Ph 4-CH3S〇2-Ph H H H ch3 H 0 1 110 4-Cl-Ph 4-CF3S-Ph H H H ch3 H 0 . 1 111 4-Cl-Ph 4-CF3S〇2-Ph H H H ch3 H 0 1 112 4-Cl-Ph 4-CHF2S-Ph H H H ch3 H 0 1 113 4-Cl-Ph 4-CHF2S02-Ph H H H ch3 H 0 1 114 4-Cl-Ph 4-n-C3F7S-Ph H H H ch3 H 0 1 115 4-Cl-Ph 4-i~C3F7S-*Ph H H H ch3 H 0 1 116 4-Cl-Ph 4~n~C3F7S〇2~Ph H H H ch3 H 0 1 117 4-Cl-Ph 4-n-CeFi3S~Ph H H H ch3 H 0 1 118 4-Cl-Ph 4-n~CeFi3S〇2~Ph H H H ch3 H 0 1 119 4-Cl-Ph 4-CF3S〇2NH-Ph H H H ch3 H 0 1 120 4-Cl-Ph 4-(5-CF3-2-Pyr)0 H H H ch3 H 0 1 • _Ph 121 4-Cl-Ph 2,4-Cl2-Ph H H H ch3 H 0 1 122 4-Cl-Ph 3,4-Cl2-Ph H H H ch3 H 0 1 123 4-Cl-Ph 3-Cl-4-F-Ph H H H ch3 H . 0 1 124 4-Cl-Ph 3-CF3-4-N〇2-Ph H H H ch3 H 0 1 125 4-Cl-Ph 3,5-(CH3)2-Ph H H H CHa H 0 1 126 4-Cl-Ph 2,3,4,5,6-Fs-Ph H H H ch3 H 0 1 —17 —— — — — — — — — — — — II 1111111 ·11111111 I H I I J . (請先閱讀背面之注意事項再填寫本頁) 紙張尺度適用中國國家標準（CNS)A4規格\2ίό X 297公釐） 585849 A7 B7 五、發明說明（4) (續） 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 127 4-Cl-Ph 4-(Cl2C=CH- CH20)-Ph H H H ch3 H 0 1 128 4-Cl-Ph 4-(Cl2C=CH- CH2S)-Ph H H H ch3 H 0 1 129 4-Cl-Ph 4-(Cl2C=CH- CH2S〇2)-Ph H H H ch3 H 0 1 130 4-Cl-Ph 2,6-Cl2+(Cl2 -C=CHCH20)-Ph H H H ch3 H 0 1 131 4-Cl-Ph 4-CN-Ph H H H ch3 H 0 1 132 4-Cl-Ph 4-N〇2-Ph H H H ch3 H 0 1 133 4-Cl-Ph 4-(Ph-C = C)Ph H H H ch3 H 0 1 134 4-Cl-Ph 2-Naph H H H ch3 H 0 1 135 4-Cl-Ph 6-Cl-2-Naph H H H ch3 H 0 1 136 4-Cl-Ph 6-CF3-2-Naph H H H ch3 H 0 1 137 4-Cl-Ph 5-Cl-2-Pyr H H H ch3 H 0 1 138 4-Cl-Ph, 6-Cl-3-Pyr H H H ch3 H 0 1 139 4-Cl-Ph 5-N〇2-2-Pyr H H H ch3 H 0 1 140 4-Cl-Ph 5-CN-2-Pyr H H H ch3 H 0 1 141 4-F-Ph 4-Cl-Ph H H H ch3 H 0 i 142 4-F-Ph 4-Cl-Ph H H H ch3 H n-ch3 1 143 4-F-Ph 4-F-Ph H H H ch3 H 0 1 144 4-F，Ph 4-I-Ph H H H ch3 H 0 1 -18- (請先閱讀背面之注意事項再填寫本頁)
— — — — — — — ^---I-----I 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（π ) 衷1 (鏞) 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W B 145 4-F-Ph 4-i-C3HT-Ph H H H CH3 H 0 i 146 4-F-Ph 4-CF3〇-Ph H H ； H ch3 H 0 1 147 4-F-Ph 4-CFa-Ph H H H ch3 H 0 1 148 4-F-Ph 4-CN-Ph H H H ch3 H 0 1 149 4-F-Ph 4-NOz-Ph H H H ch3 H 0 1 150 4-F-Ph 3-C1-4-F-Ph H H H ch3 H 0 1 151 4-F-Ph 2,3,4,5,6- F5-Ph H H H ch3 H 0 1 152 4-F-Ph 6-C1-2-Pyr H H H ch3 H 0 1 153 4-Br-Ph 4-Cl-Ph H H H ch3 H 0 1 154 2-I-Ph 4-CF3-Ph H H H ch3 H 0 1 155 4-I-Ph 4-Cl-Ph H H H ch3 H 0 1 156 4-I-Ph 4-I-Ph H H H ch3 H 0 1 157 4-I-Ph 4-CFa-Ph H H H ch3 H 0 1 158 2-CH3-Ph 3,5-(CH3)2- Ph H H H ch3 H 0 1 159 2-CH3-Ph 4-CFa-Ph H H H ch3 H 0 1 160 3-CH3-Ph 3,5-(CH3)2- Ph H H H ch3 H 0 1 161 4-CHa-Ph 3,5-(CH3) 2-Ph H H H CHa H 0 1 —19 --------------1111111 ^ — — — — — — — I I I till. (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明) u_ (續） 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 162 2-CH30-Ph 3,5-(CH3).2 H H H CH3 H 0 1 -Ph 163 3-CFa-Ph 4-Cl-Ph H H H ch3 H 0 1 164 4-CHaO-Ph 3,5-(CH3) 2 H H H ch3 H 0 1 -Ph 165 4-CH3〇-Ph 4-Cl-Ph H H H ch3 H 0 1 166 4-CH30-Ph 4-Cl-Ph H H H ch3 CH3 0 1 167 4-CH3〇-Ph 4-Cl-Ph H H H ch3 1V-C3H7 0 1 168 4-CH3〇-Ph 4-Cl-Ph H H H ch3 Π-C3H7 0 1 169 4-CH3〇-Ph 4-Cl-Ph H H H ch3 Π-ΟλΗθ 0 1 170 4-CH30-Ph 4-Cl-Ph H H H ch3 H 0 4 171 4-CHaO-Ph 4-Cl-Ph H H H C 2H5 H 0 1 172 4-CH30-Ph 4-Cl-Ph H H H n*&quot;C 3H7 H 0 1 173 4-CHaO-Ph 4-Cl-Ph H H H 1-C3HT H 0 1 174 4-CH3〇-Ph 4-Cl-Ph H H H C-C3H5 H 0 1 175 4-CHaO-Ph 4-Cl-Ph H H H t&quot;C^Hg H 0 1 176 4-CHaO-Ph 4-Cl-Ph H H H (CH2)4 0 1 177 4-CFaO-Ph 4-Cl-Ph H H H ch3 H 0 1 178 4-CHFaO-Ph 4-Cl-Ph H H H ch3 H 0 1 179 4-CF3SO2O 4-Cl-Ph H H H CHa H 0 1 -Ph 180 4-CHF2S-Ph 4-Cl-Ph H H H ch3 H 0 1 •20 ---------------------訂---------線 (請先閱讀背面之注意事項再填寫本頁) 本紙U尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（θ 表1 (鏞) 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 181 4-CHF2S〇2-Ph 4-Gl-Ph H H H CH3 H 0 1 182 4-CFaS-Ph 4-Cl-Fh H H H ch3 H 0 1 183 4-CFaS02-Ph 4-Cl-Ph H H H ch3 H 0 1 184 4-n - C3F7-PI1 4-C1-Ph H H H ch3 H 0 1 185 4-CF3S02NH- Ph 4-Cl-Fh H H H ch3 H 0 . 1 186 4-CFa-Ph 2-Cl-Ph H H H ch3 H 0 1 187 4-CF3-Ph 4~C1-Ph H H H ch3 H 0 1 188 4-CF3-Ph 4-F-Ph H H H ch3 H 0 1 189 4-CF3-Ph 4-I-Ph H H H ch3 H 0 1 190 4-CF3-Ph 2,4-Cl2-Ph H H H ch3 H 0 1 191 4-CF3-Ph 2,4-Fz-Ph H H H ch3 H 0 1 192 4-CF3-Ph 2,6-F2-Ph 'h H H ch3 H 0 1 193 4-CF3.-Ph 4-I-2-CH3-Ph H H H ch3 H 0 1 194 4-CFa-Ph 4-CH3-Ph H H H ch3 H 0 1 195 4-CFa-Ph 4-CFa-Ph H H H ch3 H 0 1 196 4-CF3-Ph 4-C2F5-Ph H H H ch3 H 0 1 197 4-CF3-Ph 4-n-C3F7-Ph H H H ch3 H 0 1 198 4-CF3-Ph 4-i~C3F7~Ph H H H ch3 H 0 1 199 4-CF3-Ph 4-(Ph0)-Ph H H H CHa H 0 1 200 4-CF3-Ph 4-CF30-Ph H H H CHa H 0 1 201 4-CF3-Ph 4-CHFzO-Ph H H H ch3 H 0 1 —21_ --------訂---------線-^丨·---- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（％ ) 寿1 (續) 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 Rl R2 R3 r R5 W a 202 4-CF3-Ph 4-CF3S〇2〇-Ph H H H CH3 H 0 1 203 4-CFa-Ph 4-CFaS-Ph H H H ch3 H 0 1 204 4-CFa-Ph 4~CF3S〇2-Ph H H H ch3 H 0 1 205 4-CF3-Ph 4-CHF2S-Ph H H H ch3 H 0 1 206 4-CF3-Ph 4-CHF2S02-Ph H H H CHs H 0 _ 1 207 4-CFa-Ph 4-n~C3F7S-Ph H H H CH3 H 0 1 208 4-CFa-Ph 4~i~C3F7S~Ph H H H ch3 H 0 1 209 4-CFa-Ph 4-n~C3F7S〇2~Ph H H H ch3 H 0 1 * 210 4-CFa-Ph 4-n-CeFi3S-Ph H H H ch3 H 0 1 211 4-CFa-Ph 4*~卩-。6卩 1 3SO2- Ph H H H ch3 H 0 1 212 4Uh 4-CF3S〇2NH-Ph H H H ch3 H 0 1 213 4-CFa-Ph 4-C00CH3-Ph H H H ch3 H 0 1 214 4-CFa-Ph 2-(Cl2C=CH- CH20)-Ph H H H ch3 H 0 1 215 4-CFa-Ph 4-(Cl2C=CH- CH2S)-Ph H H H ch3 H 0 1 216 4-CF3-Ph 4-(C12C=CH-CH2S02卜Ph H H H ch3 H 0 1 217 4-CF3-Ph 2,6-Cl2+(Cl2 -C=CHCH2〇)-Ph H H H ch3 H 0 1 •22- --------------------訂---------線 ^9. (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 經濟部智慧財產局員工消費合作社印製 A7 _B7 五、發明說明（Μ ) 表一L(續）
No. Ar1 Ar2 Rl R2 R3 r R5 a 218 4-CF3-Ph 4- (ί-〇4Η9〇 = C) H H H CH3 H 0 1 - Ph 219 4-CFa-Ph 4-(Ph-C=C) H H H ch3 H 0 1 -Ph 220 4-C2F5-Ph 4-Cl-Ph H H H ch3 H 0 . 1 221 4-C2Fs-Ph 4-CFa-Ph H H H ch3 H 0 1 222 4-C2Fs-Ph 4-i-C3F7-Ph H H H ch3 H 0 1 223 4~n~C3F7&quot;Ph 4-Cl-Ph H H H ch3 H 0 1 224 4-n-C3F7-Ph 4-CF3-Ph H H H ch3 H 0 1 225 4-n~C3F7~Ph 4-i-C3F.T-Ph H H H ch3 H 0 1 226 4-i-C3FT-Ph 4-Cl-Ph H H H ch3 H 0 1 227 4-i-C3F7**Ph 4-CF3-Ph H H H ch3 H 0 1 228 4-i-C3F7-Ph 4-i-C3FT-Ph H H H ch3 H 0 1 229 4-N〇2-Ph 4-F_Ph H H H ch3 H 0 1 230 4-Ph-Ph 4-Cl-Ph H H H ch3 H 0 1 231 2,4-Cl2-Ph 4-Cl-Ph H H H ch3 H 0 1 232 2,4-Cl2-Ph 4-Cl-Ph CH3O H H ch3 H 0 1 233 2,4-Clz-Ph 4-CF3-Ph H H H ch3 H 0 1 234 2,6-Cl2-Ph 4-Cl-Ph H H H ch3 H 0 1 235 2,6-F2-Ph 4-Cl-Ph H H H ch3 H 0 1 236 2,6-F2-Ph 4-CFa-Ph H H H ch3 H 0 1 237 3,4-F2-Ph 4-F-Ph H H H ch3 H 0 1 23 --------訂---------線&quot;^^丨· (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 _B7 五、發明說明（》) 轰JL(續） 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R*1 RB W a 238 3,4-F2-Ph 4-CF3-Ph H H H CH3 H 0 1 239 2,3-(CH3)2-Ph 3,5-(CH3)2 -Ph H H H ch3 H 0 1 240 3,5-(CH3)2-Ph 4-CH3-Ph H H H ch3 H 0 1 241 3,5-(CH3)2-Ph 4-0CH3-Ph H H H ch3 H 0 . 1 242 3,5-(CH3)2-Ph 2,3-(CH3)2 -Ph H H H ch3 H 0 1 243 3,5-(CF3)2-Ph 4-CFs-Ph H H H ch3 H 0 1 244 2,4,6-(CH3) a-Ph 4-Cl-Ph H H H ch3 H 0 1 245 2,3,4,5,6-Fs-Ph 4-F-Ph H H H CHs H 0 1 246 5-Cl-2-Pyr 4-Cl-Ph H H H CH3 H 0 1 247 5-Cl-2-Pyr 4-CF3-Ph H H H ch3 H 0 1 248 5-C1-2-Pyr 5-Cl-2-Pyr H H H ch3 H 0 1 249 5-Cl-2-Pyr 5-CF3~2- Pyr H H H ch3 H 0 1 250 6-CJL-3 二 Pyr 4-Cl-Ph H H H ch3 H 0 1 251 6-Cl-3-Pyr 4-CFa-Ph H H H ch3 H 0 1 252 5 - CF3**2-Pyr 4-Cl-Ph H H H ch3 H 0 1 253 5-CF3-2-Pyr 4-CF3-Ph H H H ch3 H 0 1 254 5-CF3-2-Pyr 4-Cl-2-Pyr H H H ch3 H 0 1 255 5-CF3-2-Pyr 4-CF3-2- Pyr H H H ch3 H 0 1 -24- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規袷uiu X 297公釐） 585849 A7 B7 五、發明說明) 弄1 (鏞) 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 256 6-CF3-3-Pyr 4-Cl-Ph H H H CH3 H 0 1 257 6-CF3-3-Pyr 4-CFa-Ph H H H ch3 H 0 1 258 5-CN-2-Pyr 4-Cl-Ph H H H ch3 H 0 1 259 5-N〇2-2-Pyr 4-Cl-Ph H H H ch3 H 0 1 260 5-CF3〇-2-Pyr 4-Cl-Ph H H H ch3 H 0 . 1 261 5-CF30-2-Pyr 4-CFa-Ph H H H ch3 H 0 1 262 5-CF3S-2-Pyr 4-Cl-Ph H H H CHa H 0 1 263 5-CF3S-2-Pyr 4-CF3-Ph H H H CHa H 0 1 264 5-CF3S02-2-Pyr 4-Cl-Ph H H H ch3 H 0 1 265 5-CF3S02-2-Pyr 4-CFa-Ph H H H ch3 H 0 1 266 3,5-Cl2-2-Pyr 4-Cl-Ph H H H CHa H 0 1 267 3,5-Cl2-2-Pyr 4-CF3 ~Ph H H H CH3 H 0 1 268 5-CF3-3-Cl-2-Pyr 4-Cl-Ph H H H ch3 H 0 1 269 5-CF3-3-Cl-2-Pyr 4-CF3-Ph H H H ch3 H 0 1 270 2-Naph 4-C1-Ph H H H ch3 H 0 1 271 6-Cl-2-Naph 4-Cl-Ph H H H ch3 H 0 1 272 6-Cl-2-Naph 4-CF3-Ph H H H ch3 H 0 1 273 6_CF3-2-Naph 4-Cl-Ph H H H ch3 H 0 1 274 6-CF3-2-Naph 4-CF3-Ph H H H ch3 H 0 1 275 6-CF30-2-Naph 4-Cl-Ph H H H ch3 H 0 1 276 6-CF3S-2-Naph 4-Cl-Ph H H H ch3 H 0 1 277 6-CF3S02-2-Naph 4-Cl-Ph H H H CHa H 0 1 -25- -I----------I ·11111--訂·--------. (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格Uiu X 297公釐） 585849 κι Β7 五、發明說明（Μ) 表一L_(續） 經濟部智慧財產局員工消費合作社印製
No. Ar1 Ar2 R1 R2 R3 R4 R5 W a 278 4-CFa-Ph 4-Cl-Ph H H H CHa H 0 1 b=l 279 4-Cl-Ph 4-Cl-Ph H H H CH3 H 〇 1 11 b=l 280 4-Cl-Ph Ph H H H ch3 H 0-1 11 R7 = CH3,b=l 281 4-CFa-Ph Ph H H H ch3 Η 1 l〇 1 11 R7=CH3,b=l 282 4-CF3〇-Ph 4-CF3-Ph H H H ch3 H 0 1 283 2-F-4-Cl-Ph 4-CFa-Ph H H H ch3 H 0 1 284 2-Cl-4-F-Ph 4-CFa-Ph H H H ch3 H 0 1 285 2,4-F2-Ph 4-CFa-Ph H H H ch3 H 0 1 286 4-(PhC=C) Ph 4-Cl-Ph H H H ch3 H 0 1 -26 --------^---------^ (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（&lt;) 表2 (R6=R7=Re = H，b=〇) No. Arl Ar2 (QU R3 R4 R5 W a 287 Ph 4-Cl-Ph CH=CH H CH3 H 0 1 288 Ph 4-Cl-Ph CEC H ch3 H 0 1 289 Ph 4-CF30-Ph C=C H ch3 H 0 1 290 4-Cl-Ph 4-Cl-Ph CH=CH H ch3 H 0 1 291 4-Cl-Ph 4-CFa-Ph c^c H ch3 H 0 1 表3 經濟部智慧財產局員工消費合作社印製 (R6 = R7 = Re = H，b=〇，d=0) No. Ar1 Ar2 R3 R4 R5 W a 292 4-Cl-Ph Ph H CHa H 0 1 293 4-CF3-Ph 4-CFa-Ph H CH3 H 0 1 294 3-CF3-Ph 4-CFa-Ph H ch3 H 0 1 295 2-CFa-Ph 4-CF3-Ph H ch3 H 0 1 296 4-CFa-Ph 4-Cl-Ph H C2H5 H 0 1 29? 4-CF3-Ph 4-Cl-Ph H H H 0 1 298 4-CF3-Ph 4-Cl-Ph H t~C^Hg H 0 1 299 4-CFa-Ph 4-Cl-Ph H (CH2)4 0 1 300 4-CFa-Ph 2-Cl-Ph H ch3 H 0 4 -27- --------訂---------線—j (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（21u χ 297公釐） 585849 A7 B7 五、發明說明（4) 經濟部智慧財產局員工消費合作社印製 表3 (德) No· Ar1 Ar2 Π3 R4 R5 W n 301 4-Cl-Ph 2,6-Cl2-4-(Cl2C= H CHa H 0 1 CHCH2O)-Ph 302 4-CFa-Ph 4-(t-C4H9C = C)- H CH3 H 0 1 Ph 303 4-CFa-Ph 4-(PhC = C)-Ph H ch3 H 0 1 304 3,5-(CH3)2~Ph 4-Cl-Ph H ch3 H 0 1 305 •4-CF3-Ph 4-Cl-Ph H ch3 H 0 1 306 4-CF3〇-Fh 4-CF3-Ph H ch3 H 0 0— i 1 307 3-CF3〇-Ph 4-CF3-Ph H ch3 H 0 1 308 4-CFa-Ph Ph H ch3 H 0 1 v R7=CH3，b=l 309 4-F-Ph 4-CFa-Ph H ch3 H 0 1 310 254-Cl2~Ph 4-CFa-Ph H ch3 H 0 1 311 4-1-Ph 4-CFa-Ph H ch3 H 0 1 312 4-N〇2-Ph 4-CF3-Ph H ch3 H 0 1 313 4-C2F5-Ph 4-CF3-Ph H ch3 H 0 1 314 4-CFa-Ph 4-CFaO-Ph H ch3 H 0 1 315 4-CH3〇-Ph 4-CF3-Ph H ch3 H 0 1 316 4-CN-Ph 4-CFa-Ph H ch3 H 0 1 317 2,6-Cl2-Ph 4-CF3-Ph H CHa H 0 1 -28- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格uw 297公釐） 585849 A7 B7 五、發明說明（π ) 裹3 (籲) 經濟部智慧財產局員工消費合作社印製
No. Ar* Ar2 R3 IT W t\ 318 3,5-Cl2-Ph 4-CF3-Ph H CHa H 0 1 319 2-Cl-Ph 4-CFa-Ph H ch3 H 0 1 320 3-Cl-Ph 4-CF3-Ph H ch3 H 0 1 321 4-Cl-Ph 4-CF3-Ph H ch3 H 0 1 322 2-Cl-4-N02-Ph 4-CFa-Ph H ch3 H 0 1 323 3-CH30-Ph 4-CF3-Ph H ch3 H 0 1 324 3,4-Cl2-Ph 4-CFa-Ph H CHa H 0 1 325 2-Cl-4-F-Ph 4-CFa-Ph H ch3 H 0 1 326 4-CF3-Ph 4-CFa-Ph CHa ch3 H 0 1 327 2,5-Cl2-Ph 4-CFa-Ph H ch3 H 0 1 328 4-CFaS-Ph 4-CF3-Ph H ch3 H 0 1 329 2-CHa-Ph 4-CFa-Ph H ch3 H 0 1 330 3-CH3-Ph 4-CF3-Ph H ch3 H 0 1 331 4-CHa-Ph 4-CFa-Ph H ch3 H 0 1 332 2-CH3〇-Ph 4-CFa-Ph H ch3 H 0 1 333 2,4-F2」Ph 4-CFa-Ph H ch3 H 0 1 334 5,6-Cl2~3-Pyr 4-Cl-Ph H ch3 H 0 1 335 5, 6-Cl2*&quot;3-Pyr 4-CFa-Ph H ch3 H 0 1 336 2-Cl-3-Pyr 4-CFa-Ph H ch3 H 0 1 337 6-Cl-3-Pyr 4-CFa-Ph H ch3 H 0 1 338 2-Naph 4-CF3-Ph H ch3 H 0 1 339 4-C00CH3-Ph 4-CF3-Ph H 1 ch3 H 0 1 29 (請先閱讀背面之注意事項再填寫本頁)
I I I n ϋ n 一-0、» I n ϋ ϋ n n I I I ϋ ϋ ϋ ·ϋ ϋ n H ϋ H ϋ I 1 I ϋ ϋ n n n n I 本紙張尺度適用中國國家標準（CNS)A4規格uiu X 297公釐） 585849 A7 B7 五、發明說明（&gt;〇 經濟部智慧財產局員工消費合作社印製
表3 (缠) No. Ar1 Ar2 R3 R4 R5 W a 340 3-Pyr 4-CF3-Ph H CH3 H 0 1 341 2-C1-6-CH3-3- 4-CF3-Ph H ch3 H 0 1 Pyr 342 2,6-Cl2~4-Pyr 4-CF3-Ph H ch3 H 0 1 .343 4 十 CHh 4-CFs-Ph H ch3 H 0 1 344 4-n*-C4Hg-Ph 4-CF3-Ph H ch3 H 0 1 345 4-(CH3)2N-Ph 4-CF3-Ph H ch3 H 0 1 346 4-CH3C00-Ph 4-CF3-Ph H ch3 H 0 1 347 4-CN-Ph 4-CFa-Ph H t-CUHg H 0 1 348 2-CHF2S-3-Pyr 4Uh H CH3 H 0 1 349 6-CHF2〇-3-Pyr 4-CFa-Ph H ch3 H 0 1 350 2-F-4-CF3-Ph 4-CFa-Ph H ch3 H 0 1 351 4-CF3C0NH-Ph 4-CFa-Ph H ch3 H 0 1 352 4- (3-CI-5-CF3- 4-CF3-Ph H ch3 H 0 1 2-Pyr)0-Ph 353 2,4-Cl2-Ph 4-CFa-Ph H t-C4H9 H 0 1 354 2，4-Cl2_Ph 4-CFa-Ph H I-CsHt H 0 1 355 4-CN-Ph 4-CFa-Ph H i-C3Ht H 0 1 356 2,4-Cl2-Ph 4-CF3-Ph H ch3 CH3 0 1 357 4-CN-Ph 4-CF3-Ph H ch3 CHa 0 1 Rf=H -30 --------------------- 訂---------線j (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（巧） 壶3 (績) No. Ar1 Ar2 R3 Rn W a 358 4-CN-Ph 4-CF3-Ph H CH3 CH3 0 1 Rf=L 359 2-Pyr 4-CFa-Ph H ch3 H 0 1 360 2-CHaS-3-Pyr 4-CFa-Ph H ch3 H 0 1 361 2-CH3S02-3-Pyr 4-CF3-Ph H CHa H 0 1 362 3,5-Cl2-2-Pyr 4-CF3-Ph H CH3 H 0 1 363 3-C1-5-CF3-2- 4-CFa-Ph H ch3 H 0 1 Pyr 364 4-CF3S〇2NH-Ph 4-CFa-Ph H ch3 H 0 1 365 4-CN-Ph 4-CF3-Ph CH3 ch3 H 0 1 366 4-CF3S02-Ph 4-CFs-Ph H CHa H 0 1 367 1-Naph 4-CFa-Ph H CHa H 0 1 368 4-n-C3H7S-Ph 4-CF3 H CHa H 0 1 369 4-C2F5S-Ph 4-CFa-Ph H CH3 H 0 1 在表1, 2和3中Ph代表苯基，Pyr表示吡啶基，Naph --------訂-------Ί 線—一 (請先閱讀背面之注意事項再填寫本頁)^:/. 經濟部智慧財產局員工消費合作社印製 指萘基而c -則表示脂環烴。 表4即表示在表1，2及3中所列述化合物之物理性。 31- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 _ B7 五、發明說明（Μ ) 經濟部智慧財產局員工消費合作社印製 表4 編號 物理性（熔點，折射率， NMR(CDC13/TMS), (Ϊ 值（PPffi)) 1 m. p. 101 °C 2 m.p.152 °C 3 m. p. 121 °C 9 nD 1.542 (21 °C) 10 paste NMR: 1.65(s.3H), 1.51-1. 72 (m.4H) , 1.80-2.12 (m. 4H), 3.69(s.2H), 3.95-4.03 (m.2H) , 5.59(br.lH), 6.8-6.9(m.2H), 7.1-7. 40 (m. 6H). 11 paste NMR: 1.74(s.3H), 2.06(m.2H), 3.61(m.2H), 3. 55-3. 80 (m. 2H), 4.28(m.2H), 7. 06 (br. 1H) , 7.12 (d. 2H), 7.18-7. 24 (m. 2H), 7.25-7.40(m.4H). 12 m.p.127-133 °C 13 m.p.138-139 °C 14 ίπ.ρ.Ώ8-99 °C (Rf=H) 15 paste (Rf=L) NMR： 1.32(d.3H), 1.75(s.3H), 3.72(s.2H), 4. 60-4. 70 (m. 1H), 5.97(br.lH), 6.76(d.2H), 7. 20-7. 42 (m. 6H). 16 paste (Rf=L) NMR: 0.83(t.3H), 1.20-2.00 (m.4H), 3.66(s.2H), 4.82(br.lH), 5.87(br.lH), 6.86(d.2H), 7.15-7. 30 (m. 6H). 32- (請先閱讀背面之注意事項再填寫本頁) 訂---------線— 本紙張尺度適用中國國家標準（CNS)A4規格αιυ X 297公釐） 585849 Α7 Β7 五、發明說明（Μ ) 衷4 (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，（Ϊ 值（ppm)) 17 paste (Rf=H) NMR: 0. 89 (t. 3H), 1.20-2. 00 (m. 4H) , 3. 40-3. 57 (m. 2H), 5.02(br.lH), 5.70(br. 1H), 6.73(d.2H), 7.05-7. 30 (m. 6H). 18 m. p.125-128 °C (Rf=H) 19 paste (Rf=L) NMR: 0.81(t.3H), 1.10-1.80(m.6H), 3.67(s.2H)， 4.75-4.82(m.lH) , 5.T9(br.lH), 6.85(d. 2H), 7.18-7.40(m.6H). 20 m. p.97°C 21 m. p.131 °C 22 m.p.107-110 °C 23 m.p.123-126 °C 24 m.p.125-126 °C 25 paste NMR: 1.08(s.9H), 3.68-3.82 (m.2H) , 4. 36-4. 47 (m. 2H), 5.69(br.lH), 6.75(d.2H), 7. 18-7.46 (m. 6H). 26 m.p.78-84 °C 27 paste NMR: 1.94(s.3H)，3.20 (s.3H), 3.83 (m.2H), 4.46 (s.2H), 6.82(cL2H), 7·12-7·30(ηι·5Η)，7.37(d.lH). 28 m.p.110-112 °C 29 m.p.118-120 °C -33- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（Ζΐϋ X 297公釐） 585849 A7 B7 五、發明說明（W) 經濟部智慧財產局員工消費合作社印製
轰(續） 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，值（ppm)) 30 πι. p.72-74 °C 41 m.p.132-133 °C 42 Λ.p.116-117 °C 44 m. p.134-143 eC (Rf=H) 45 paste (Rf=L) NMR: 1.31(d.3H), 1.74(s.3H), 3.54(s.2H), 4.62-4. 70 (m. 1H), 6.12 (br. 1H) , 6. 76 (d. 2H) , 7. 06-7. 30 (m. 6H). 46 paste (Rf=H) NMR: 0.92(t.3H), 1.20-2.00 (m.4H) , 3.29(s.2H), 5.02-5.12(s.lH), 5.45(m.lH), 6.75(d.2H), 7.13-7.26(m.6H). 47 paste (Rf=L) NMR: 0.85(t.3H), 1.20-2.00 (m.4H) , 3.49(s.2H), 4.78-4.81(m.lH), 5.81(br.lH), 6.84(d.2H), 7·15-7·30(πι·6Η). 48 m.p/134-136 eC 49 m·p·103-104 eC 50 paste NMR: 1.65(s.3H), 1.50*2.10(m.6H) , 3.54(s.2H), 3.88-3.93 (s.2H) , 5.52(br.lH), 6.79(d.2H), 7.10-7.30(m.6H)： 51 m. p. 96-99 °C -34- (請先閱讀背面之注意事項再填寫本頁) 0. 訂---------線丨4 · 準 標 家 國 國 中 用 適 度 尺 張 紙 本 釐 公 97 2 X σ 1 ΙΖ 格 .規 585849 A7 B7 五、發明說明（^ ) 經濟部智慧財產局員工消費合作社印製 (籲） 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，值（ppm)) 52 m.p.121-122 °C 53 m.p.121-124 °C 54 paste NMR: 1.07(s.9H), 3.52-3.66 (m.2H) , 4. 33-4. 52 (m. 2H), 5.55(br.lH), 6.78(d.2H), 7.10-7. 33 (m. 6H). 55 paste NMR: 1.20-2.00 (m.8H) , 3. 49 (s)/3. 52 (s) (2H), 4. 35 (br) /4. 85 (br) (1H) ,5.62 (br) /5.95 (br) (1H), 6. 70-6. 80 (m. 2H) , 7. 00-7. 30 (m. 6H). 56 m.p.113-114 °C 57 m.p.132-135 °C 58 m. p.142 °C 59 m.p.169 〇C 60 m.p.126-127 °C 61 paste NMR: 1.64(s.3H), 1.52-2.15(m.8H), 3.53(s.3H), 3.95-4.03(m.2H) , 5.59(br.lH), 6.86-6. 95 (m. 2H), 7.12-7.40(m.6H). 62 m.p.126-127 °C 63 m.p.122-128 °C 64 m. p. 152 °C 65 m.p.87-89 °C -35- (請先閱讀背面之注意事項再填寫本頁)
訂---------線II 格 規 A4 S) N (C 準 標 家 國 國 中 用 適 度 尺 張 紙 本 釐 公 97 2 585849 A7 B7 五、發明說明（外） (續） 經濟部智慧財產局員工消費合作社印製 .編號 物理性（熔點，折射率， NMR(CDC1 3 /TMS)，cJ 值（ppm)) 66 m. p. 95°C 67 m.p.153 °C 68 paste NMR: 1· 64 (s· 3H), 1.50-2.10 (m.6H)，3.54 (s.2H)， 3. 87-3. 93 (m. 2H) , 5. 47 (br. 1H), 6. 80 (d. 2H), 7.15-7.40(m.6H). 69 m.p.124-141 °C 70 paste NMR: 0.85(t)/0.92(t) (3H), 1. 20-2. 00 (m. 4H),. 3.21-3. 36 (m)/3. 49 (s) (2H), 4. 74-4. 80 (br)/5. 04-5.12 (br) (1H), 5.41(br)/5.76(br) (1H) , 6. 70-7. 30 (m. 8H). 71 m. p.124-130 °C (Rf=H) 73 m·p·126-127 °C 74 m. p·· 104-105 0C 75 m. p. 140 °C 76 πκρ. 142 °C 77 paste NMR: 1.07(s.9H), 3. 52-3.66 (m.2H), 4.34-4.50 (m.2H), 5· 57(br.1H), 6· 75(d·2H), 7· 12-7· 37(m. 6H)· 36 --------^-------- (請先閱讀背面之注意事項再填寫本頁) 線丨 « 本紙張尺度適用中國國家標準（CNS)A4規格U_lu X 297公釐） 585849 A7 Β7 五、發明說明 寿4 (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，值（ppm)) 79 paste NMR: 1.20-2. 10 (m.8H), 3. 48 (s)/3. 50 (s) (2H), 4.32(br)/4.84(br) (1H), 5. 60 (br)/5.90 (br) (1H), 6.67-6.75 (m.2H) , 7. 00-7.30 (m. 6H). 80 paste NMR: 1.91(s.3H), 3.1KS.3H), 3. 70 (s. 2H) , 4. 39-4. 51 (m. 2H), 6.78(d.2H), 7.09(d.2H), 7. 22-7. 26 (m. 4H). 81 m. p. 83-84 °C 82 m. p.57-63 °C 83 m. p. 114-117 eC 84 m. p.105-108 °C 85 m· p· 148-149 eC (Rf=H) 86 m. p.152-154 °C (Rf=L) 88 m. p.145-146 °C 89 m.p.123 °C 90 m.p.135-137 eC 91 m.p.96-97 °C 92 m.p.160-161 °C 94 m. p.127-130 °C 95 m. p.132-133 °C 96 m· p· 120-121 eC 97 m. p. 96-100°C _37_ (請先閱讀背面之注意事項再填寫本頁) --·--------訂---------^ — · 規 4 ' A ·: ‘ s).&gt;.’N(、 準少-標f 國..&gt; 國、 中.‘ 用V Μ . 度 尺 張 紙 本 釐 公 97,ν 585849 A7 B7 五、發明說明（4)弄4 (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC1 3 /TMS)，值（ppm)) 99 m.p.114-115 °C 100 m.p.126-127 °C 102 i ρ· 162 °C 103 m.p.159-163 °C 105 m.p.130 °C 108 m. p. 85-86 °C 109 paste NMR: 1.80(s.3H), 3.03(s.3H), 3.58(s.2H), 4.32 (dd. 2H), 5.88(br.lH), 6.96(d.2H), 7.18(s.2H), 7.32(d.2H), 7.86(d.2H). 114 m. p. 91-92 eC 116 paste 關R: L81(s.3H), 3.59(s.2H), 4. 36-4.45 (m. 2H) , 5.68(br. 1H), 7.03-7.10 (m.2H), 7.18(d.2H), 7.33(d.2H), 7.76(d.lH), 7.99(d.lH)· 117 m.p. 102-104 °C 118 paste NMR: 1.81(s.3H), 3.59(s.2H), 4. 30-4. 45 (m. 2H) , 5.66(br.lH), 7.04-7.10(m.2H), 7.17 (d.2H)，7.33 (d.2H), 7.75 (d.lH), 7.99(d. 1H). 120 m.p.160-161 °C 121 m.p. 88-90 °C -38 (請先閱讀背面之注意事項再填寫本頁)
本紙張尺度適用中國國家標準（CNS)A4規格νιυ a 297公釐） 585849 A7 B7 五、發明說明（Μ ) 經濟部智慧財產局員工消費合作社印製 (纊） 編號 物理性（熔點，折射率， NMR(CDC1 3 /TMS)，cT 值（ppm)) 122 m.p.125-126 °C 123 m. p.93-94 °C 124 m.p.141-142 °C 125 m·p.175-176 〇C 126 nD 1.511(26 V) 125 m. p.88-89 °C 128 m. p.87-89 °C 129 paste NMR: 1.81(s.3H), 3.59(s.2H), 3.93(d.2H), 4.35(dd.2H), 5.80(br,lH), 5.98 (t.lH), 6.98 (d.2H), 7.19 (d.2H), 7.33(d.2H), 7.82(d.2H). 130 m.p.127-128 eC 133 m.p.156-158 °C 134 m.p·146-147 eC 141 m.p.159-160 °C 142 m.p.156-157 °C 143 m.p.128-129 °C 144 m. p.144 °C 145 m.p.137-139 °C 146 m.p.107-109 °C 147 m.p.112-113 V 148 m.p.138-140 °C —39 (請先閱讀背面之注意事項再填寫本頁) ____ 訂---------線丨j 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（&gt;〇 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13/TMS)，值（ppm)) 149 m.p.108-110 °C 150 m.p.128-129 °C 151 m.p.108-110 °C 152 m. p.136 °C 153 m. p.146 eC 154 m. p.146-147 °C 156 m. p.142-143 eC 157 m. p.98-99 °C 158 m.p.123-124 °C 160 m.p.117-118 °C 161 m.p.110-112 °C 163 nD 1.521(21 °C) 164 m.p.126-127 °C 165 m.p.115 °C 166 m. p.129-131 eC 167 paste (Rf=H) NMR: 0.91(t.3H), 1.20-1.90 (m.4H) , 3. 18-3. 38 (m. 2H), 3.78(s.3H), 5.04-5.12(m.lH), 5.39(br.lH), 6.70-6.82(m.6H), 7.20(d.2H). -40- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（M ) (續） 閱 讀 背 面 之 注 意 事 項 再 填 寫 本 頁 編號 物理性（熔點，折射率， nmr(cdci3 /tms)，β 值（ppm)) 168 paste (Rf=L) NMR: 0.84(t.3H), 1.20-1.90 (m.4H) , 3. 41-3.55 (m. 2H), 3.79(s.3H), 4.72-4.80 (m.lH), 5.72(br.lH), 6.78-6.85 (m.4H) , 7.05(d.2H), 7.24(d.2H). 169 m.p.121-126 eC (Rf=H) 170 paste NMR: 1.61(s.3H), 1.45-2. 10 (m.6H) , 3. 52 (s. 2H) , - 3. 78 (s. 3H), 3.85-3.93 (m.2H), 5.44(br.lH), 6.78(d. 1H), 6.87(d.2H), 7.15(d.2H), 7.28(d.2H).
171 m.p.104-107 °C 172 paste NMR: 0.95(t.3H), L 35-1.55 (m.2H) , 1. 95-2.05 (m. 2H), 3.53(s.2H), 3.80(s.3H), 4.19-4. 33 (m. 2H), 5.63(br,lH), 6.74 (d.2H), 6.87(d.2H), 7.11(d. 2H), 7.23(d. 2H). 173 m.p.114-117 °C . , 經濟部智慧財產局員工消費合作社印製 174 m.p.119-122 °C ' 175 paste NMR: 1.03(s.9H), 3.49-3.64 (m.2H), 3.81(s.3H), 4. 32-4. 50 (m. 2H), 5.58(br.lH), 6.77(d.2H), 6.91(ά.2Η), 7.13(d.2H), 7.24(d.2H). 本紙張尺度適用中國國家標準（CNS)A4規格的7公釐） 585849 A7 ____ B7 五、發明說明（令） SLA (續） 經濟部智慧財產局員工消費合作社印製
編號 物理性（熔點，折射率、 NMR(CDC13 /TMS)， 值（ppm)) 176 paste NMR: 1.20-2.10(m.8H), 3.43-3. 55 (m. 2H), 3. 73 (s)/3.87 (s) (3H), 4. 26 (br)/4. 80 (br) (1H), 5.61 (br)/5.86 (br) (1H), 6. 65~7. 25 (m. 8H). 184 m.p.87-88 °C 丨 186 m. p.130 °C 187 m.p.119 °C 188 m.p.128-130 °C 189 in. p. 145-147 °C 190 m.p-80-81 °C 191 m. p.88-90 °C 192 m.p.112-113 °C 193 m.p.108-109 °C 195 m.p.95-96 °C 19B m.p.105-111 °C 197 m. p. 82-85 °C 199 m.p.135-136 °C 200 m. p. 85-87 °C 207 m·ρ·59-60 °C —9 (請先閱讀背面之注意事項再填寫本頁) —訂---------線r 本紙張尺度適用中國國家標準（CNS)A4規格（21u X zy/公釐） 585849 A7 B7 五、發明說明（41 ) (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，ί 值…讯）） 209 paste NMR: 1.83(s.3H), 3.67(s.3H), 4. 30-4. 50 (m. 2H) , 5.82(br.lH), 7.03-7.05 (m.2H) , 7.37(d.2H), 7.61(d.2H), 7.74(d.lH), 7.98(d. 1H). 210 m.p.90-91 °C 211 paste NMR: 1.83(s.3H), 3.68(s.2H), 4.30-4. 46 (m. 2H) , 5.73(br.lH), 7.03-7.10(m.2H) , 7.38(d.2H), 7.61(d.2H), 7.75(d.lH), 7.98(d. 1H). 213 m.p.103-105 °C 216 m.p.87-88 °C 218 m.p.159-161 °C 219 m.p.177-178 °C 220 m.p.140-143 °C 221 m.p.133-137 °C 223. m.p.88-89 °C 224 m.p.86-88 °C 229 nD 1.554 (26 °C) 230 m.p.131-132 °C 231 m. p. 100 °C 232 nD 1.543 (21 °C) 233 m.p.123-124 °C -43- ---------------------訂---------線一 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明) 表(續） 經濟部智慧財產局員工消費合作社印製
編號 物理性（熔點，折射率， NMR(CDC1 3 /TMS)， 值（ppm)) 234 m.p.141 °C 235 m.p.130-131 °C 236 m.p.154-155 °C 237 m. p.94eC 238 m. p. 85°C 243 m. p.104-106 eC 244 m. p. 136 °C 245 m. p. 87°C 253 m.p.97-99 °C 269 m.p.137-139 °C 270 m. p. 138 °C 278 m.p.71-73 °C 279 m.p.103-106 °C 280 m.p.106-108 °C ；: --..... 281 m.p*114-117 °C 282 m.p.121-125 °C 283 m.p. 105-106 °C 284 m.p.141-143 °C 285 m.p.115-120 °C 286 m.p. 162-164 °C 287 m.p. 140-142 eC --------^---------線. (請先閱讀背面之注意事項再填寫本頁) -44- 本紙張尺度適用中國國家標準（CNS)A4規格Uii) X 297公釐） 585849 '乂 .... A7 B7 五、發明說明（和） (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13/TMS)，C?值（ppm) 288 paste NMR: 1.89(s.3H), 4.27(s.2H), 6.52(br.lH), 7.26(d.2H), 7.30-7.60 (m.5H). 289 paste NMR: 1.91(s.3H), 4.31(s.2H), 6.28(br.lH), 6.96(d.2H), 7.35-7.60(m.5H). 290 m.p.163-164 °C 291 paste NMR: · 1.92(sr3H), 4.37(s.2H)，6.33(br.lH)，7.02(d.2H), 7.35(d.2H), 7.47(d.2H), 7.59(d.2H), 292 m.p.l35rl40 °C 293 m.p.135-136 °C 294 m. p. 115 °C 295 m.p. 128-130 °C 296 m.p.ljl8-119 eC 297 m.p. 134-140 °C 298 m· p· 125-135 0C 299 paste NMR: 1· 40-2· 30 (m. 8H), 4· 62/4· 99 (br· s· 1H), 6· 38/6· 62 (br· s· 1H), 6. 99-6· 97 (m· 2H), 7*16-7*30(m.2H), 7. 62-7* 82 (m. 4H) —45— (請先閱讀背面之注意事項再填寫本頁) - · -|線_ 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 經濟部智慧財產局員工消費合作社印製 A7 _B7 五、發明說明U4 ) (續） 編號 物理性（熔點，折射率， NMli(CDCl3 /TMS)，ί 值（ppm) 300 paste NMR: 1. 50-2.35 (m.8H) , 1.84(s.3H), 4.12(q.2H), 6.31(br.s.lH), 6.92(d.2H), 7.21(dd.lH), 7.34(dd.lH), 7.66(d.2H), 7.85(d.2H) 301 m.p.135-136 °C 302 m.p.217-218 eC 303 m.p.195-198 °C 304 m.p.129-130 °C 305 m.p.106-108 °C 306 m.p.132-136 °C 307 m. p.92°C 308 m. p.72-77 °C 309 m.p.135-137 °C 310 m.p.120-122 °C 311 m.p：155-160 °C 312 m. p. 96-97 eC 313 m.p.127-129 °C 314 m.p.127-128 eC 315 m.p.161-166 °C 316 paste NMR: 1.98(s.3H), 4.45(q.2H), 6.65 (br. s. 1H) , 7.03(d.2H), 7.58(d.2H), 7.76(d.2H), 7.88(d.2H) .46 (請先閱讀背面之注意事項再填寫本頁) ---------訂---------線一 本紙張尺度適用中國國家標準（CNS)A4規格Uio X 297公釐） 585849 A7 B7 五、發明說明（4r ) 表」L (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)，值（ppffl) 317 paste NMR: 1.98(s.3H), 4.47(s.2H), 6. 33 (br. s. 1H), 7.01(d. 1H), 7.32(m.4H), 7.57(d.2H) 318 paste NMR: . 1.97(s.3H), 4.44(q.2H), 6. 56 (br. s. 1H) , 7.02(d.2H), 7.53(m. 1H), 7.61(d. 2H), 7.63(s.2H) 319 m·p·122-123 eC 320 m.p.149-154 °C &quot; 321 m.p.144-145 °C 322 m.p.205-208 °C 323 m.p.142-144 °C 324 m.p.147-148 °C 325 m.p.130-132 °C 326 m. p. 98-100°C .327 m.p.118-121 °C 328 m.p.140-141 °C 329 m.p.137-140 °C 330 m.p.166-168 °C 331 m.p.187-190 °C 332 m. p. 85-88 °C 333 m.p·127-128 0C 334 m.p.171-173 °C -47- 11------^---------線 (請先閱讀背面之注意事項再填寫本:!;-)； 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（0) 表」_ (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR(CDC13 /TMS&gt;， ί 值（ppm) 335 m.p.158-159 °C 336 m.p.150-154 °C 337 m.p.137-140 °C 338 m.p.219-222 eC 339 m.p.126-130 °C 340 m.p.133-134 °C 341 paste NMR: 1.99(s.3H), 2.50(s,3H), 4.41(d.lH)，4.49(d.lH)， 7.03(d. 2H), 7.25(d.2H), 7. 30 (br. s. 1H) , 7.59(d.2H), 8.18(d. 1H) 342 m.p.119-123 °C 343 m.p.249-251 °C 344 m.p.184-187 °C 345 m.p.254-257 °C 346 m.p.170-173 °C 347 m.p.111-114 °C 348 paste NMR: 1.97(s.3H), 4.40(d. 1H), 4.47(d. 1H), 6. 65 (br. s. 1H), 7.03(d.2H), 7.19-7.23(m.lH), 7.59(d.2H), 7.62(t.lH), 7.80-7.9ΚΓΠ.1Η), 8. 55-8. 57 (m. 1H) -48 -------------1 (請先閱讀背面之注意事項再填寫本頁) --訂---------線j ,4..J*irc 本紙張尺度適用中國國家標準（CNS)A4規格Ujlu X 297公釐） 585849 A7 B7 五、發明說明（V ) 表—L (續） 經濟部智慧財產局員工消費合作社印製 編號 物理性（熔點，折射率， NMR (CDC1 3 /TMS) , ί 值（ppm) 349 paste NMR: 1.94(s.3H), 4.41(dd.2H), 6. 71 (br. s. 1H), 6.93((1.1H), 7.00(d. 2H), 7.45(t.2H), 7.55(d.2H), 8.11-8.14(πι.1Η), 8.56(d.lH) 350 m.p.118-119 °C 351 m.p.161-163 °C 352 m.p.132-139 °C 353 m.p.149-151 °C 354 paste NMR: 1.22-1.29 (m.6H) , 2.76(m.lH), 4.60(q.2H), 6.70(br.s.lH), 6.99 (d.2H)，7.34 (m.lH), 7.43 (m.lH), 7.48(d.2H), 7.70(d.2H) 355 paste NMR: 1.20-1.32(m.6H) , 2. 81 (m. 1H) , 4.60(q.2H), 6.43 (br. s. 1H) , 6. 98 (d. 2H) , 7. 55 (d. 2H), 7.76-7.86 (m.4H) , 7.70(d.2H) 356 paste NMR: 1· 52-1.57 (m· 3H), 1· 91/1.93 (s.3H), 5· 03/5· 26 (q.2H), 6.76/6.96 (br.s. 1H), 6.98-7. 10 (m. 2H), 7. 26-7. 79 (m. 5H) 357 m. p.210-213 °C (Rf=H) 358 m.p.206-208 °C (Rf=L) 359 m· p· 90-91 eC -49 --------訂---------線·^ (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格《innc 297公釐） 585849 A7
B 五、發明說明（# ) 經濟部智慧財產局員工消費合作社印製
表_丄（續） 編號 物理性（熔點，折射率， NMR(CDC13 /TMS)， ί 值（ppm) 360 m.p.137-140 °C 361 m. p. 13 2 °C 362 paste NMR: 1.99(s.3H), 4.43 (d.2H), 4.49 (d.lH)，7.04 (d.2H), 7.57(d.2H), 7.89(d.lH), 8. 25 (br. s. 1H) , 8.41(d.lH) 363 paste NMR: 1.99(s.3H), 2.61(s.3H), 4.46(s.2H), 7. 02-7. 09 (m. 4H), 7.58(d.2H), 7.92-7.96 (m.lH), 8. 53-8. 55 (m. 1H) 364 m.p.200-202 °C 365 m.p.137-142 °C 366 m.p.130-133 °C 367 m.p.138-140 °C 368 m.p.141-142 °C 369 m.p.138-139 °C -50 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 2：；/ ） 585849 經濟部智慧財產局員工消費合作社印製 A7 ____B7____ 五、發明說明（Μ ) 在表3或表4中，Η-Η或Rf-L傺指稱立體異構物；
Rf_H表示於立體異構物中具有高Rf值異構物，而Rf-L則 表示具有低Rf值之異構物。 以下卽列述本發明之典型實施例，配方例以及試驗例。 奮榆例 奮渝例1編號63化合物之製造 將4 -氯酚（2.56克），溴乙醛二甲基乙縮醛（3.4克）， 無水碳酸鉀（2.76克）及觸媒用量之碘化鈉加入於DMF(二 甲基甲醯胺）（2〇ml)並在加熱下回流3小時。加水於反 應混合物，然後用醋酸乙酯萃取並使有機層經由無水硫 酸鈉乾燥，並蒸餾溶劑。殘留物經由矽凝膠管柱層析法 (醋酸乙酷-己烷）精製而得卜氯苯氧乙醛二甲基乙縮醛 (2 · 3 7克）〇 將4-氯苯氧乙醛二甲基乙縮醛（1·〇克）溶解於兩酮（l〇ml) ，加入2N氫氯酸（1·〇克），並將混合物在回流下加熱8小 時。待反應混合物濃縮後，加水並用醋酸乙酯萃取混合 物。萃取液則經由無水硫酸鈉予以乾燥。蒸除溶劑而得 4-氯苯氧乙醛之精製物。 將粗製之4 -氛苯氣乙醛（0·5克），氣化鈉⑶·17克）及 氯化銨（0 · 2 7克）加入於2 8 %氨水（2 0 m 1 )中並搜拌2天。 加醋酸乙酯於反應溶液並用水洗淨混合物，經由無水硫 酸鈉乾燥蒸除溶劑。將所生成之油液溶解於THF(四氫呋 喃）（5inl)並加入4 -氯苯乙醯氣（0.38克）及三乙胺（0·22 克）。並將混合物在室溫攪拌6小時。加水於反應混合 -51- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） • ϋ .1 ϋ I ϋ I I ϋ ϋ ϋ ϋ -I · ϋ II ϋ I ϋ I I ϋ ϋ I I I ^ ^ I I ϋ .1 ϋ .1 ϋ I ϋ H ϋ H ϋ ^ 1 ϋ ϋ ϋ ·1 I ϋ I (請先閱讀背面之注意事項再填寫本頁) 585849 A7 B7 五、發明說明（0) (請先閱讀背面之注意事項再填寫本頁) 物，用醋酸乙酯萃取並將萃取物經由無水硫酸鈉乾燥， 同時蒸除溶劑。殘餘物經由矽凝膠管柱層析法（醋酸乙 酯-己烷）加以精製而得標的之化合物（0 · 2 1克；收率2 4 % ;熔點 1 2 2 - 1 2 8 °C )。 實施例2 編號64化合物之製造 將4 -氯酚（1 0克），氯丙酮（1 0 · 8克），無水磺酸鉀（1 2 · 9 克）及碘化鉀（1·3克）加入於丙酮（100ml)中並在回流下 加熱6小時。過濾反應混合物並濃縮濾液得4 -氯苯氣丙 酮（14克）。 將4 -氯苯氧丙酮（6.0克），氰化鈉（1.91克）及氯化銨 (2. 6克）加入於28%氨水（20ml)内經劇烈攪拌24小時。 加醋酸乙酯於反應混合物，用水洗淨混合物並經由無 水硫酸鈉乾燥，同時蒸除溶劑而得2 -胺基-2 -甲基-3 - ( 4 -氯苯氯基）丙腈（6.5克）。 經濟部智慧財產局員工消費合作社印製 將4-氯苯氧丙酮（0·4克）加入於亞硫醯氯（lflil)並在回 流下加熱1小時，在減壓下蒸餾多餘之亞硫醯氯。所生 成之醯基氯加入於T H F溶液（5 in 1 )，其中2 -胺基-2 -甲基 - 3 - ( 4 -氯苯氧基）丙腈（0 · 4 9克）和三乙胺（0 · 2 6克）則在 冰冷下溶解並在室攪拌3小時。加水於反應混合物並用 醋酸乙酯萃取混合物。萃取物則經由無水硫酸鈉予以乾 燥並蒸除溶劑。用己烷-乙醚洗淨固體殘餘物得標的化 合物（0 · 5 6 克，産率 6 6 % ; m · p . 1 5 2 °C )。 實」fe_M 3.· 一編號8 1化合物之製造 將4 -氣苯氣丙酮（1 · 8 4克），氰化銷（G · 5克），氯化鞍 -52- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7_ 五、發明說明) (請先閱讀背面之注意事項再填寫本頁) (〇 . 9克）溶解在甲醇（1 0 m 1 )中，並添加餘量之無水乙胺 溶液。在室溫攪拌混合物2天。待完成反應後，蒸除溶 劑並用醋酸乙酯萃取殘餘物，隨即利用一般之步驟而得 2-胺基-2-甲基- 3- (4-氯苯氧基）丙腈（2·2克）。 將2 -胺基-2-甲基- 3- (4 -氯苯氧基）丙腈（0·5克）及4-氯苯基乙醯氯（0.38克）溶解在THMlOml)中，並添加以 吡啶（Q . 1 6克）在回流下加熱混合物5小時。待冷卻至室 溫之後，過濾不溶物質並蒸除溶劑。所生成之油狀物則 經由矽凝膠管柱層析法（醋酸乙酯-己烷）加以純化而得 標的之化合物（0 · 1 6克；産率2 0 % ; m · p · 8 3 - 8 4 °C )。 奮旃例4 編號1 6 6化合物之製造 將4 -甲氣苯基乙酸（0·67克）及2 -氯-卜甲毗啶基碘（1.10 克）懸浮在T H F ( 1 0 m 1 )中，並在室溫下滴加以三乙胺（0 . 5 0 克）。攪拌5分鐘後，添加2 -胺基-2 -甲基-3 - ( 4 -氯苯氧 基）丁腈（Q · 9 0克）並攪拌混合物歷6小時。待完成反應 後，過濾不溶物質並蒸除溶劑。殘餘物經由矽凝膠管柱 層析法（醋酸乙酯-己烷）加以精製得標的化合物（G. 7 8克 ;産率 5 2 % ; m · ρ · 1 2 9 - 1 3 1DC )。 奮施例J3 編號2 5 3化合物之製造 經濟部智慧財產局員工消費合作社印製 將2 - ( 5 -三氟甲基-2 -吡啶基）醋酸氫氯化物（〇 · 7 4克）， 2 -胺基-2-甲基- 3_(4 -三氟甲基苯氣）丙腈（0·65克），2-氯-卜甲基吡啶基碘（1 · 1 7克）及三乙胺（0 · 9 3克）加入於 乙腈（1 0 m 1 )並在回流下加熱6小時。加水於反應混合物 ，用醋酸乙酯萃取混合物並經由無水硫酸鈉乾燥。然後 -53-本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（p) 蒸除溶劑。殘餘物經由矽凝_管柱層析法（醋酸乙酯-己 烷）精製而得標的之化合物（0·34克；産率28%;&quot;1·?· (請先閱讀背面之注意事項再填寫本頁) 9 7 - 9 9 〇C ) 〇 奮旃例β 編號2 8 8化合物之製造 將3-苯乙炔羧酸（〇·28克），2-胺基-2-甲基- 3-(4-氯 苯氧基）丙腈（〇 · 4 0克）以及二環己磺化二亞胺（〇 · 4 1克） 溶解在二氯甲烷（5 m 1 )並將溶液在回流下加熱8小時。 過濾反應混合物並將濾液濃縮。殘餘物經由矽凝膠管柱 層析法（醋酸乙酯-己烷）精製而得標的之化合物（〇 · 1 1克 ;産率1 7 % ;漿狀）。 經濟部智慧財產局員工消費合作社印製 本發明之含有式U)之胺基乙腈衍生物為活性成分之 農園藝殺蟲劑係適用於控制各種農業，林業，園藝，儲 藏物品以及衛生的害蟲或對稻田，果樹，蔬菜，其他農 作物以及花卉有害線蟲等各種有害蟲類。對於有害蟲類 有很強的殺蟲效果，例如，鱗翅目（L e p i d 〇 p t e r a )害蟲， 如小角紋葉捲蛾(Adoxophyes oranafasciata)，小捲葉 蛾（Adoxophyes s p)，蘋小食心蟲（Grapholita inopinata )，梨小食心蟲（Grapholita m ο 1 e s t a )，大豆 食心蟲（Leguminivora glycinivorella),桑捲葉蛾 (Olethreutesinori),茶葉細蛾（Caloptilia thevivora) Caloptilia z a c h v y s a ,窄翅潛葉蛾(Phyllonorycter ringoniella)，梨潛皮細蛾（Spulerrina astaurota )， 葉粉蝶（Piers r a p a e crucivora ),美洲棉鈐蟲，棉鈐 蟲，煙草蚜蟲以及蕃茄螭螬(Heliothis sp.)，蘋果蠹 -5 4 - 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（Η ) 蛾（L a s p e y resiapomone11 a )，小菜蛾（P1ut e 1 1 a xjj 〇 s t e \J_b_)，蘋實巢蛾(Ajr,g,i,r ,e s t h i a con Lu g e 11a), (請先閱讀背面之注意事項再填寫本頁) 梨實巢蛾（Carposina ni pones is )，七星稻螟（C h_i 1 〇 s u 1 is )，黑尾夜蟬（CjLaphalocrocis iL^dlja Lj^) ，煙草籮蛾（Kphestia e 1 ut e 1 1 a ),桑螟（Glyphodes EXJ oalis)，三化螟（Scirpophaga incertulas )，直紋 稻苞蟲 Lp a r n a r a guttata )，水稻葉夜蛾（Pseudaletia se^p a rata)，大螟(S e s a m i a i n f e r e n s )，斜紋夜蛾 (S p 〇 d o p t e r a 1 i tura),甜菜夜蛾(Spodopter a e x i g u a_) 經濟部智慧財產局員工消費合作社印製 ,半翅目(Hemiptera)之害蟲如紫莞葉蟬(Macrosteles fascifrons)，稻螺蛉(Nephotettix cincticeps)，稻 褐飛虱(Nilaparvata 1 u g e n s)，百背飛風(Sogatella furcifera)，纟秀皮蟲(D i aphor ina c i t r i )，萄粉虱 (Aleurolobus taonabae)，棉粉風（B e m i s i a t a b a c i ), 溫室白粉虱(Trialeurodes vaporariorum)，葡萄蚊 (Lipaphis e r y s i m i)，桃姆(H y z u s persicae),印第安 蠘蚊(Ceroplastes ceriferus),綿献(Pulvinaria aurantil)，樟圓敝（Pseudaonidia duplex)，梨圓阶 (Comstockaspis perniciosa),矢尖蚁（U n a s p i s yanonesis);鞘蛾科(Coleopt er a)之害蟲如大豆甲蟲 (A η o m a 1 a rufocuprea),日本甲蟲（Popillia japonica ) ，释草甲蟲（Lasioderma serricorne),竹蠢（L y c t u s brunneus)，2 8點瓢蟲(Epilachna vj_g i n t i o t o p u n c t a t a ) ，緣 H 象(Callosobruchus chinensis)，蔬菜象甲 -5 5 -本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 經濟部智慧財產局員工消費合作社印製 585849 A7 B7 五、發明說明) (Listroderes costirostris),玉米象(Sitophilus z e a, m a i s )，花象蟲(Ant honomus gr adi s ),稻象甲 (Lissorhoptus oryzophilus),黃守爪蠅 (Aulacophora f e m 〇 r a 1 i s )，稻負泥蟲(Oul ema o ryz ae) ，黃寬條跳甲(Phyllotreta striolata)，松斑螟 (T o m i c u s piniperda)，馬鈐薯甲蟲(Leptinotarsa decemlineata)，墨西哥豆瓢蟲(Epilachna varivestis ) ，南爪十二星葉甲(Diabrotica s p ·);雙翅目(D i p t e r a ) 之害蟲如爪實蠅（D a c u s (Zeugodacus)cucurbitae)，橘 小實蠅(D a c u s ( Bactrocera) dorsalis),稻潛蠅(Agromyza oryzae)，戀蠅(Delia ant i qua ),玉米籽粟蠅(Delia P 1 a t u r a )，大豆萊瘿蚊（Asphondy 1 ia s p·),家蠅(M u s c a domestica)，家蚊(C u 1 e x p i p i e n s);線蟲屬 Ty lenchida) 之害蟲如敗根線蟲（Pratylenchussp.),馬鈐薯包囊線 蟲(Globodera rostochiensis)，根結線蟲(Meloidogyne s p.),橘線蟲（Tylenchulus semipenetrans), Aphelenchus avenae，菊乾尖線蟲（Aphelenchoides ritzemabosi)〇 含有本發明式（I )胺基乙腈衍生物之農園藝殺蟲劑對 於稻田作物，農場作物，果樹，蔬菜，以及其他農作物 和花卉在抵抗上述害蟲方面有顯著之控制效果，可施用 在稻田水，莖部及葉子或土壤，如在稻田，農地，果樹 ，蔬菜，其他作物和花卉在預定害蟲出現之適當時機以 及在害蟲出現之前式出現以後，本發明之農園藝用殺蟲 -56- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） ----------------------訂---------線—赢 (請先閱讀背面之注意事項再填寫本頁) I I ^ I I I MM MM MM I I · 經濟部智慧財產局員工消費合作社印製 585849 A7 B7 五、發明說明（π ) 劑經證實顯示有所需要之效果。 本發明之農園藝殺蟲劑一般在使用之前傺使用習知之 農藥製法調配成習用之適當製劑。 式（I)之胺基乙腈衍生物，如有需要時可摻混以適量 之載體和輔助劑經由溶解，分散，懸浮，混合，浸積吸 收或吸附作用，而將混合物配製成懸浮液，乳化液，液 體，可濕性粉劑，粒劑，粉劑，錠劑等。 任何之固體或液體均可做為本發明之惰性載體使用。 可供使用之固體載體，例如包括有大豆粉，榖粉，木粉 ，樹皮粉，鋸屑，煙草莖粉末，果實榖粉，麥粕，纖維 素纖維，植物萃取後所剩之殘餘物，合成聚合物如研磨 之合成樹脂，黏土（如高嶺土，皂土，酸性黏土等），滑 石（如，滑石，藥蠟石等），5夕石類（如矽藻土，石英砂， 雲母，白碳（微細之水合矽，宜為矽酸水合物，含有高 分散矽酸；某些産物主要俗含有矽酸鈣），活性碳，硫 粉，浮石，煆烷之矽藻土，研磨磚粉産品，飛灰和砂， 無機礦物粉末如磺酸鈣，磷酸鈣，化學肥料或硫銨之組 份，磷酸銨，硝酸銨，尿素和氯化銨，該呰載體可單獨 使用或以2種以上混合物使用。 液體載體包括其中之一種本身係具有溶劑之作用而另 一種則無有溶劑作用但可分散活性成分可做為輔肋劑使 用。其典型之實施例包括有以下之載體，可單獨或以二 種以上做為混合物使用，例如，水，醇類（如甲醇，乙 醇，異丙醇，丁醇，乙二醇等），酮類（如丙酮，甲乙酮 -57- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） (請先閱讀背面之注意事項再填寫本頁)
585849 經濟部智慧財產局員工消費合作社印製 A7 B7_ 五、發明說明（Η ) ，甲異丁酮，二異丁酮，環己酮等），醚類（如乙醚，二 噁烷，溶纖素，二丙醚四氫呋喃等），脂族烴類（如煤油 ，礦油等），芳香族烴（如苯，甲苯，二甲苯，溶劑萘， 烷基萘等），li化烴類（如二氯乙烷，氯仿，四氯化硕， 氯化苯等），酯類（如醋酸乙酯，酞酸酯，酞酸二異丙酯 ，酞酸二丁酯，酞酸二辛酯等），醯胺類（如二甲基甲醯 胺，二乙基甲醯胺，二甲基乙醯胺等），腈類（如乙腈等） ，二甲基亞礁等。 其他輔肋劑包括以下所列舉之典型輔肋劑。該些輔助 劑偽依照其目的而使用並可單獨使用或併合二種或以上 輔肋劑使用。又，在某種案例中則不使用輔助劑。 以乳化，分散，增溶溶解及/或潤濕活性成分為目的 時，可使用界面活性劑，界面活性劑的例子，例如包括 ，聚氣乙烯烷醚，聚氣乙烯烷芳基醚，聚氧乙烯高級脂 肪酸酯，聚氧乙烯樹脂酸酯，聚氧乙烯山梨糖醇-月桂 酸酯，聚氧乙烯山梨糖醇-油酸酯，磺酸烷基酯，蔡磺 酸縮合物，木素磺酸酯，高級醇硫酸鹽等。 輔肋劑可使用以安定活性成分化合物並黏結或結合活 性成分化合物。輔肋劑的例子包括有，酪朊，明膠，澱 粉，甲基纖維素，羧甲基纖雒素，阿拉伯樹膠，聚乙烯 醇，木材松節油，稻殼油，皂土，木質素亞硫酸鹽液體 等。 輔肋劑可用以改善固體産品之流勳性。例如此種輔助 劑的例子為蠟，硬脂酸鹽，磷酸烷酯等。 -58- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） (請先閱讀背面之注意事項再填寫本頁) -— — —— — — I— ^ — — — — — — — — — . 585849 A7 B7 五、發明說明（π ) 關於懸浮液産品用之反絮凝劑，例如可使用萘磺酸縮 合物，凝縮之磷酸鹽輔肋劑。 (請先閱讀背面之注意事項再填寫本頁) 消泡劑可使用矽酮油等輔肋劑。 如有需要時可調整活性成分之用量。如為粉劑或粒劑 時則適當之用量為ο . ο 1至5 G %重量，而乳化劑及可濕性 粉劑之適用量為〇 . Q1至50%重量。 欲控制各種不同之害蟲，本發明之農園藝用殺蟲劑可 應用適當用稀釋或懸浮在水中等在農作物在上面發現有 害蟲時可預期地達成防止昆蟲侵害或對害蟲出沒場所産 生致命的後果。 本發明之農園藝用殺蟲劑的用量視其不同因素如使用 目的，處理害蟲之方式，農作物的生長狀態，害蟲之出 沒方面，天候，環境條件，配方，使用方法，應用地點 及應用時期而有差異。依照目的每10公畝可適當地選擇 有0 . 1至1 0 k g活性成分化合物之範圍之内。 為能進一步地延長控制病蟲害的時間或減少劑量，可 使用本發明之農園藝用殺蟲劑與其他之控制病蟲害之農 園藝用劑混合。 經濟部智慧財產局員工消費合作社印製 本發明之典型實施例及試驗例係如下所逑。惟此並不 能限制本發明。 在以下配製劑中，所有之”份π係表示”份重”的意思。
ILJLULX 在表1，2或3中所示之化合物 5 0份 二甲苯 4 0份 聚氧乙烯壬苯醚和苯磺酸烷酯之混合物 1 0份 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 經濟部智慧財產局員工消費合作社印製 A7 B7 五、發明說明（W) 將 以 上 各成 分 混 合 並 均 勻 溶 解 形 成 為 乳 液 〇 配 製 例 2 在 表 1， 2或 3 中 所 示 之 化 合 物 3份 黏 土 粉 末 8 2份 矽 藻 土 粉末 15份 將 制 以 tRA 上 各成 分 混 合 並 均 勻 研 磨 形 成 為 粉 劑 〇 StL 在 Tr\ 表 Λ-1 , 2或 3 中 所 示 之 化 合 物 5份 皂 土 粉 末和 黏 土 90份 木 質 素 磺酸 鈣 5份 將 以 上 各成 分 均 勻 混 合 至 捏 和 於 添 加 適 量 水後，所生 成 之 混 合 物經 由 造 hi 及 乾 燥 而 得 W 劑 〇 配製例4 在 表 1， 2或 3 中 所 示 之 化 合 物 2 0份 高 嶺 土 及合 成 之 局 分 散 性 矽 酸 7 5份 聚 氧 乙 烯壬 苯 醚 和 烷 基 苯 擴 酸 鋁 之 混 合 物 5份 將 以 上 各成 分 混 合 並 均 勻 研 磨 而 得 可 濕 性 粉劑。 試 驗 例 小菜蛾（P 1 τι t e 1 1 a xylostella)/&lt;^ 除蟲效果 在 中 國 甘籃 的 禾 Μ 上 駐 留 以 培 育 用 小 菜 蛾 (plutella X y 1〇 S t e 1 ] J )成蟲並令其下蛋徑2 天後開始培育，在中 國 甘 藍 禾 S上 所 下 的 蛋 沈 澱 或 浸 潤 以 含 有 表 1，2或3化 合 物 之 農 m m 稀 釋 至 5 0 0 p p in 並歷 3 0秒鐘 0 風 乾後，將禾 m 置 於 2 5 °C之溫室内 〇 從 浸 漬 藥 液 起 6 天 後 ，檢査孵化 昆 蟲 的 數 目。 並 由 下 式 計 算 昆 蟲 之 死 亡 率 同 時依照以下 -60- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 __B7_ 五、發明說明（t?) 之標準方式加以測定。1地區，1 〇隻毘蟲，3序列 (請先閱讀背面之注意事項再填寫本頁) 無處理區之孵化昆蟲數 -處理區的孵化昆蟲數 真正的昆蟲死亡率=- 無處理區之孵化毘蟲數 A=死亡昆蟲率100% B =死亡毘蟲率99至99 % C =死亡昆蟲率89至80 % D=死亡毘蟲率79至50% 所得結果如表5所示。 試驗例2__茶小捲葉蛾（Adoxophyes s p ·)之除蟲效果 將茶葉（品種：Yabukita)浸漬在含有表1 , 2或3所載 化合物之農藥經稀釋至5G0ppm之藥液中歷30秒鐘。經風 乾後，將其放置在直徑9 c m之塑膠盤中，並接種以2蟲 鹼期之茶小捲葉蛾（Adoxophyes s p .)盤子罩以蓋子放置 在2 5 °C及7 0 %濕度之溫室内。從接種起8天後，撿查毘 蟲之死亡數目並依照試驗例1做成測定。1地區，1 0隻 毘蟲，3序列。 經濟部智慧財產局員工消費合作社印製 示 所 5 表 如 結 得 所 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 _B7 五、發明說明（k ) 表5 經濟部智慧財產局員工消費合作社印製
化合物 編號 試驗例 1 試驗例 2 化合物1 編號 試驗例 1 試驗例 2 2 A A 4 9 B 3 A 5 2 A A 12 A 5 3 A A 13 A A 5 4 A 14 A A 5 5 A 2 1 A A 5 7 A A 2 2 A 6 0 A A 2 3 A A 6 2 A A 2 4 A A 6 4 A A 2 5 A 6 6 A A 2 6 A A 6 7 A D 2 7 A 6 8 A 2 8 A A 6 9 A A 2 9 A 7 3 A A 3 0 A A 7 4 A A 4 1 A A 7 5 A A 4 2 A 7 6 A 4 6 A 7 7 A 4 8 A A 7 9 A A •62 ------------裝--------訂------ (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（W) 經濟部智慧財產局員工消費合作社印製 表_5_ (績&gt; 化合物 编號 試驗例 1 拭驗例 2 化合物 编號 試驗例 1 試驗例 2 8 0 A A 14 1 A A 8 1 A A 14 3 A A 8 3 A A 14 6 A A 8 4 B 14 7 A A 9 1 A 14 8 A A 9 2 A A 14 9 A A 9 4 A A 15 0 A A 9 5 A A 15 1 A A 9 6 A A 15 3 A A 9 7 A A 15 6 A A 10 0 A A 15 7 A A 10 5 A A 16 3 A 10 8 A 16 5 A A 114 A A 17 3 A A 116 A A 17 4 A 118 C 17 6 A 12 1 A A 18 4 A 12 2 A A 18 6 A A 12 3 A A 18 8 A A 12 4 A A 1 8 7 A A 12 6 A A 18 9 A A 12 8 A 19 0 A A -63- --------------------訂--------11^^1.--- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 B7 五、發明說明（^) 表_5_ (續&gt; 經濟部智慧財產局員工消費合作社印製 化合物 编號 試驗例 1 试驗例 2 化合物 缠號 賦驗例 1 轼驗例 2 19 1 A A .2 4 5 A 19 5 A A 2 5 3 A A 19 6 A A 2 6 9 A A 19 7 A 2 7 0 A A 2 0 0 A A 2 7 1 A 2 0 7 A A 2 7 8 A 2 0 9 A A 2 7 9 A A 2 2 0 A A 2 8 0 A 2 2 1 A 2 8 2 A A 2 2 3 A 2 8 3 A C 2 2 4 A 2 8 4 A A 2 2 9 A A 2 8 5 A A 2 3 1 A A 2 8 6 A 2 3 2 A A 2 9 3 A A 2 3 3 A A 2 9 4 A A 2 3 4 C 2 9 6 A 2 3 5 A A 2 9 9 A 2 3 6 A A 3 0 6 A A 2 3 7 A A 3 0 7 A 2 3 8 A A 3 0 9 A A 2 4 3 A A 3 1〇 A A 2 4 4 A 3 11 A A -64 ------------ώΜ (請先閱讀背面之注意事項再填寫本頁) 訂--------- 表紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 585849 A7 _B7 五、發明說明） 經濟部智慧財產局員工消費合作社印製
*65 (請先閱讀背面之注意事項再填寫本頁) --------訂-------線| 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 申請曰期 1999， 4, 27 案 號 88106732 類 別 (以上各欄由本局填註） sa 9. 13, _ .年月曰修玉/更正/補无 A4 C4 9915271 585849 新量 專利説明書 發明 新型 名稱 發明 創作 人 中 文 英文 姓 名 國 籍 住、居所 姓 名 (名稱） 胺基乙腈衍生物，及含其之農園藝殺蟲劑組成物 (89年9月19日修正）
AMINOACETONITRILE DERIVATIVE, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPOSITION CONTAINING THE SAME 治之 亘修和 藤瓶田本本本 安三坂日日日 12 3 12 3 5 1 ο ο 13 6 6 I I I 315 5 Γ町町 Ί多多 J1本本 W市市 U野野 2 乂 Β3 R3 ffί長長 t内内 ^河河 府府府 阪阪阪 大大大 12 3 -6 •裝· 曰本農藥股份有限公司 (曰本農藥株式會社） 線 經濟部中央標準局員工消費合作社印製 國 日本 三、申請人 住、居所 (事務所） 代表人 姓 名 東京都中央區日本橋1 丁目2番5號 村田利和 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇X：297公釐）

Claims (1)

  1. 585849 A8 B8 C8 D8 「、申請專利範圍f'31隱年月日修正/更正/補充 第8810 6 732號「胺基乙膪衍生物，及含其之農園藝殺蟲劑組 成物」專利案 (89年10月31日修正） 六申請專利範圍： 1· 一種式（1)之胺基乙腈衍生物： Ο CN R5 R7 II I I I Ar 1 -(Q)d — C-N-C-(C)a — W- (C )b-Ar2 III I R3 R4 R6 Re (I) 經濟部智慧財·/1局員工消費合作社印製 (式中A r1和A r2係相同或各異分別代表苯基； 一取代之苯基至少具有一相同或各異之取代基以及 選自 鹵素原子，硝基，氰基，C6烷基，鹵代（^-(：6烷 基，C6烷氧基，鹵代烷氧基，c2- C6炔基， C2 - C6烯氧基，鹵代C2-C6烯氧基，C6烷硫基，鹵 代(]6院硫基，Ci_C6i^擴醯基，鹵代c^-Ce院磺醯 基’ c2-C6嫌硫基’鹵代C2-C6^硫基，C2-C6嫌礦醯 基，鹵代C2-C6烯磺醯基，二- G烷胺基，Ci-Ce 烷磺醯胺基，鹵代h - C6烷磺醯胺基，烷羰氧基， 鹵代烷羰胺基，（^-(：6烷氧羰基，苯基，苯氧基， 苯乙炔基，吡啶氧基以及 至少一個相同或各異之取代基在其環上具有一被取 代之吡啶氧基而選自鹵素原子，鹵代Ci - c6烷基，吡 IT------^_ (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 585849 A8 B8 C8 D8 六、申請專利範圍 代 取1 有 具 上 環 其 在 基 代 取 之 異 各 或 同 相 個1 ; 少 基至 陡 c!c I 子cl 原代 素鹵 鹵基 氧 吃烷 ¾6 基-C 陡C1吡， 之基 自 選 烷 基 氧 C烷 鹵 基 C 烷’ J基 - 硫 C!烷 代C6 或 基 萘 基 醯 磺 烷 6 C 麵 C ’ 團 基基 硫之 烷下 6 C 以 1表 C代 代 Q 鹵 R —c IR (請先閱讀背面之注意事項再填寫本頁) 經濟邡智慧財產局員工消費合作社印製 (式中R1和R2可相同或各異分別代表氫原子，q - C6 烷基’ L - C6烷氧基，而R1和R2係連結代表C2 - C6乙 炔基）-或- CeC -； d爲0或1之整數； R3代表氫原子，1-C6烷基，C2-C6炔基，或C3-C6 環院基； R4代表氫原子，L - C6烷基，或三氟甲烷基；R5代 表氫原子，或L - C6烷基；R6代表氫原子；R7代表氫 原子或甲基；R8代表氫原子；而R4和R5係一起形成爲 Ci - c6院撐； W爲-0-，-s-，-S02-或-N(R9)-(式中R9代表氫原子 或G - C6烷基），而 a和b係相同或各異爲〇或爲丨至4之整數））。 2·如申請專利範圍第1項之胺基乙腈衍生物，其中Ar1和 A r2代表苯基； -2- 本紙張尺度適用中國國家標準（CNS &gt; A4規格（210X 297公慶) 一 585849 : A8 B8 C8 D8 六、申請專利範圍 (請先閱讀背面之注意事項再填寫本頁) 一被取代之苯基至少具有一相同或各異之取代基而 選自鹵素原子，硝基，氰基，Ci- c6烷基，鹵代L-C6 烷基，C2 - C6烯基，鹵代c2 _ C6烯基，Ci - c6烷氧基， 鹵代Ci - c6烷氧基，c2 - C6烯氧基，鹵代c2 - c6烯氧基， Ci - C6烷硫基，鹵代Ci - C6烷硫基，q _ c6烷磺醯基， 鹵代Ci - c6烷磺醯基，c2 - C6烯硫基，鹵代c2 - c6烯硫 基，c2 - c6烯磺醯基，鹵代c2 - C6烯磺醯基，二-Cl - c6 烷胺基，h - c6烷磺醯胺羞，鹵代q - c6烷磺醯胺基， (^-(：6烷羰氧基，鹵代κ6烷羰胺基，烷氧羰 基，苯基，苯氧基，苯乙炔基，吡啶氧基，以及 一取代之吡啶氧基在其環上至少具有一個相同或不 同之被取代基選自鹵素原子，鹵代L - c6烷基，吡啶 基； 一取代之吡啶基在其環上至少具有一個相同或不同 之被取代基選自鹵素原子，鹵代q - c6烷基，鹵代q -C6烷氧基，鹵代Ci-G烷硫基，萘基；以及 Q代表 經濟部智慧財/i局員工消費合作社印製 R1 I -C 一 I R2 (式中R1和R2可相同或不同分別代表氫原子，（^-〇6 烷基，或Ci-G烷氧基，而R1和R2可連結代表c2-c6 乙炔基），-(^=(：11-或-(：三（：-;〇1爲0或1之整數； R3代表氫原子，Ci - C6烷基，C2 - C6炔基或C3 - C6環 本紙張尺度適用中國國家標準（CNS ) A4規格（2!〇X2W公釐） 585849 ABCD 六、申請專利範圍 院基； (請先閱讀背面之注意事項再填寫本頁) R4代表氫原子，Cl-c6烷基，或三氟甲烷基；r5代 表氫原子’或烷基；R6代表氫原子；R7代表氫 原子或甲基；R8代表氫原子； w爲-0-，-s-，-S02-或-N(R9)-(式中R9爲氫原子或 C 1 - C 6院基），以及 a和b可相同或各異爲〇或爲1至4之整數））。 3·如申請專利範圍第2項之胺基乙膪衍生物，其中Ari和 Ar2代表苯基； 一取代之苯基至少具有一相同或不同之取代基係選 -----------------自齋素原-子，硝基，氰--基-，C 1 G 6 -焼基，鹵^代^ ^ 基烷氧基，鹵代Ci- C6烷氧基，（：2-(：6烯氧基， 鹵代C2 - C6烯氧基，q _ C6烷硫基，鹵代L - C6烷硫基， (^-^烷磺醯基，鹵代1-(：6烷磺醯基，C2- (：6烯硫基， 鹵代c2 - c6烯硫基，c2 - c6烯磺醯基，鹵代c2 - c6烯磺 醯基，1-(:6烯氧羰基，苯基，苯氧基，苯乙炔基，吡 啶氧基，以及 經濟部智慧財產局員工消費合作社印製 一取代之tftil定氧基在其環上至少具有一個相同或不 同之取代基係選自鹵素原子，鹵代Ci - c6烷基，吡啶 基； 一取代之fftn定基在其環上至少具有一個相同或各異 之取代基係選自鹵素原子，鹵代L - c6烷基，鹵代Ci -C6烷氧基，鹵代Q-C6烷硫基所構成之基，萘基；或 Q代表 -4- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 585849 8 8 8 8 ABCD 六、申請專利範圍 (式中R和R2係相同或各異分別代表氫原子，Ci — C6 院基，或q - C6烷氧基，而R1和R2可連結代表C2 — C6 烷撐），-CH=CH-或-CeC - ; d爲0或1之整數； R3代表氫原子，Q - C6烷基或c2 - C6炔基； R4代表氫原子，L-C6烷基，或三氟甲烷基；R5代 表氫原子，或烷基；R6代表氫原子；R7代表氫 原子或甲基；R8代表氫原子； W爲-0-，-S-，-S02-或-N(R9)-(式中R9爲氫原子或 Q - C6烷基），而 a和b可相同或各異爲〇或爲1至4之整數））。 4. 一種農園藝用殺蟲劑之組成物，其特徵爲，包含以申 請專利範圍第1至3項中任何一項之胺基乙腈衍生物 爲活性成分者。 (請先閱讀背面之注意事項再填寫本頁) ，1Τ f 經濟部智您財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨0X297公釐）
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