TW306908B - - Google Patents
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- TW306908B TW306908B TW084100978A TW84100978A TW306908B TW 306908 B TW306908 B TW 306908B TW 084100978 A TW084100978 A TW 084100978A TW 84100978 A TW84100978 A TW 84100978A TW 306908 B TW306908 B TW 306908B
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims abstract description 14
- -1 aminecarbonyl Chemical group 0.000 claims description 237
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- 239000000203 mixture Substances 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 239000007789 gas Substances 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 230000002079 cooperative effect Effects 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
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- 241001465754 Metazoa Species 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- QJZYHAIUNVAGQP-UHFFFAOYSA-N 3-nitrobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2(C(O)=O)[N+]([O-])=O QJZYHAIUNVAGQP-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 244000125300 Argania sideroxylon Species 0.000 claims 1
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- 206010012239 Delusion Diseases 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical class NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 claims 1
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- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
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- 125000001475 halogen functional group Chemical group 0.000 abstract 2
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- 101100030842 Drosophila melanogaster chic gene Proteins 0.000 description 24
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- 239000000843 powder Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 17
- 229910052744 lithium Inorganic materials 0.000 description 17
- 241000209140 Triticum Species 0.000 description 16
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- 125000004104 aryloxy group Chemical group 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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- 125000005418 aryl aryl group Chemical group 0.000 description 9
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
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- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
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- C07D—HETEROCYCLIC COMPOUNDS
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Description
五、發明説明(1 ) A7 B7 本發明係關於’F式T之苯乙酸衍生物 R5ON=C(R4)_c(R3)=N0CH2
C02Rl (R2), c=x 其中取代基及參數具有下列之意義: X 係 NOCH3* CHOCHa > CHCH3或 CHCH2CH3; R 1 係氫或C α - C 4 -烷基; R2 係氰基*硝基,三鎮甲基,鹵素•CrCr烷基或 G - U-烷氧基; m 係0 * 1或2 *若a係2時則R2可相異; R3 係氬,氰基*硝基,羥基,胺基,鹵素-烷基 ,Ci-CA-鹵烷基,Cx-Cf烷氧基* Ci-Cf齒烷氧基》 Ca-Cf烷硫基,C'-Cf烷胺基或二- c^-c^•烷胺基; R4 係氫,氰基*硝基,羥基,胺基,鹵素,C i - C «5 -烷基 ,CrCe -烷氧基* Ci-Ce -烷硫基* Ci-Ce -烷肢基,二 -Ci-Ce -烷胺基* C2-Cs -烯基* C2-Ce -烯氧基> c2-ce-烯硫基 C, 烯胺基> N-Cz-Ce -烯基 (請先閱讀背面之注意事項I填寫本頁) 裝· 訂
U 經濟部中央橾準局員工消費合作社印製 -N-Ca-Ce-烷睽基,C2-Ca-炔基,C2-C3-炔氧基, C2-C3 -炔硫基,c2-cs -炔胺基· N-C2-Ce -炔基 -N - C i - C β -烷胺基,有可能這些基圈烴基係部份或完 全鹵化或帶有1至3個下列基:氣基,硝基,羥* * 捥基,胺基•羧基,胺羰基,胺硫羰基,鹵素, 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X 297公釐) 經濟部中央梂率局貝工消费合作杜印製 306908 b7五、發明説明(2 ) C 1 - C 3 -烷胺羰基,二-C X - C 3 -烷胺羰基,C : - C 3 ~烷胺 硫羰基,二-c:-cs-烷胺硫羰基* c:-ce-烷《基, C ^ - C <3 -烷颯氧基> C : - C β -烷氧基,C i - C β -鹵烷氧基► Ci-Cs-垸氧羰基,Ci-Ce -烷硫基,L'-Ce -烷胺基*二 -C - C β -烷胺基* C 2 - c s -烯氧基,C 3 - C β -環烷基, c3-c3 -環烷氧基,雜環基,雑環氧基,芳基,芳氧基 ,芳基-C T - C 4 -烷氣基,芳硫基,芳基-C τ - C 4 -烷硫基 ,雜芳基,雜芳氧基*雑芳基-C i - C 4 -烷氧基*雜芳 硫基,雜芳基-C a - C 4 -烷硫基•有1了能環狀基係部份 或完全鹵化或帶有1至3個下列基:氰基*硝基,羥 基,锍基,胺基,羧基,胺羰基,胺硫羰基* C i - C β -烷基,C i - C β - _ 烷基,C i - c s -烷理基 > Ci-Ce-烷硯氧基,C3-Ce-環烷基,c'-c»-烷氣基* C i - C «5 -鹵烷氧基* C i - C a -烷氧嫉基,C X - C 0 -烷硫基, CT-Ce-烷肢基,二-L'-Ce-烷胺基,Cj-Ce-烷肢羰基 ,二-Ci-Ce-烷胺羰基,Ci-Ce-烷胺硫羰基,二 -Ci-Ce-烷胺硫羰基,C2-Ce-烯基,C2-C6-烯氧基, 苄基,苄氧基,芳基,芳氧基 > 芳硫基,雜芳基,雑 芳氧基,雑芳硫基及C( = N0Rs)-An-fT7; C 3 - c s -環烷基> C 3 - C «-環烷氧基> C 3 - C β -環烷硫基, C3-Cs-環烷胺基* N-C3-Ce -環烷基- N- CS-Ce-烷胺基 * c3-c0-瑁烯基,C3-Ce-環烯氧基* c3-cs-環烯硫基 ·· ,C3-Ca-環烯胺基,N-C3-Ca-環烯基-N-Ci-Ce-烷胺 基,雑環基,雑環氧基 >雑環硫基,雑環胺基*N -雑 (請先閱讀背面之注意事項再填寫本頁) 裝. 、νβ
U 本紙張尺度適用中囷國家標準(CNS ) Α4規格(210 X 297公釐) A7 B7 五、發明説明(3 ) 環基-N - C - C 3 -烷胺基,芳基,芳氧基,芳硫基,芳 胺 基 > Ν - ‘芳 基 -N 1 ~ C & -烷胺基 *雑芳基,雑芳 氧基 » 雜 芳 硫 基 雜 芳 胺 基 > N- 雑 芳 基 -N -c 1 ~ C β -烷 胺基 t 有 可 能 r,w 環 狀 基 係 部 份 或 兀 全 鹵 化 或 帶 有1 至3 個下 列 基 氰 基 » 硝 基 » 羥 基 » m 基 * 胺 基 ,羧 基, 胺羰 基 » 胺 硫 羰 基 > 鹵 素 > Cl -C a - 烷 基 Cx f 1/ β - 鹵烷基, Cl -C & _ 烷 m 甘 巻 ♦ C 1 -C Θ - 焼 理 氧 基 c3 -c Tftff (5 -環 烷基, Cl -C β " 院 氧 基 » C】 -C β — 鹵 烷 氧 基 ♦ Cx -c <3 *** 燒 氧羰基, Ci -C S ~ 院 硫 基 i (:! -C 6 ~ 烷 胺 基 —- -c 1 - Cs-烷胺 基, c. -C » - 烷 胺 羰 基 t -~~· -C 1 — Ca -烷胺羰基, C 1 - C β ~ 烷胺 硫 羰 基 > 二 -C 1 ~ Co -烷肢硫羰基I * C 2 CB iji 甘 -Jaw * * C2 -C β - TO 氧 基 > 基 > 苄 氧 基 » 芳 基 » 芳氧 基, 雑芳 基 及 雑 芳 氧 基 > (請先閲讀背面之注意事項再填寫本頁) 裝· 訂 蛵濟部中央樣隼局貝工消費合阼.fi印裝 R5 係氫,
Ci-Cw-烷基,C3-Cs-環烷基,Cz-Ci。-烯基 * c2-c10 -炔基,Ct-Cu -烷羰基,c2-c10 -烯羰基, C 3 - C i 0 -炔羰基或C i - C i 〇 -烷碾基*有可能這些基面部 份或完全鹵化或帶有1至3個下列基:氰基》硝基, 羥基,疏基,胺基•羧基*胺羰基*胺硫羰*,鹵素 ,(:1-C3-烷基,L'-Ce-鹵烷基,CrCe-烷理基>
Ci-Ce -烷®氧基> Ci-Ce -烷氧基,Ci-Ce-歯烷氧基, C 1 - C s -烷氧激基* C : - C β -烷硫基,C 1 - C s -烷胺基,二 --C Ϊ - C 3 -烷胺基,C i - C 0 -烷胺羰基,二-C i - C «3 -烷胺羰 基,Ci-Cc5-烷胺硫羰基,二-Ci-Ce-烷胺硫羰基, 本紙張尺度適用中國國家標準(CNS ) A4规格(210X 297公釐) A7 306908 B7 五、發明説明(4 ) C2-Cs-烯基,c2-ce-烯氧基,C3-C3-環烷基, C3-C3-環烷氣基,雑環基,雜環氧基,笮基,苄氧基 *芳基,芳氧基,芳硫基,雑芳基 > 雑芳氧基及雜芳 硫基,有可能環狀基係部份或完全鹵化或帶有1至3 個下列基:氣基*硝基,羥基,蹄基 > 胺基,羧基, 胺羰基,胺硫羰基,鹵素,C i - C β -烷*,C - C 6 -鹵烷 基,c i - c s -烷砸基> c ] - s -烷sa氧基,c 2 - c«-環烷基 ,C 1 - C s -烷氧基,C i - C β -鹵烷氧基· C i - C β -垸氣羰基 ,(:i - C β -烷硫基,C , - C β -烷胺基,二~ C i - c s -烷胺基 ,Ci-Ce -烷胺羰基*二- Ci-Ce-烷胺羰基,Cx-Ce-烷 胺硫羰基,二烷胺硫羰基,C2-CS-烯基, c2-cs -烯氧基,苄基*笮氧基•芳基,芳氧基 > 芳硫 基,雑芳基•雑芳氧基*雜芳硫基或C( = N0Re)-An-R?; 芳基,芳羰基,芳《基,雑芳基*雑芳羰基或雑芳» 基*有可能這些基團部份或完全鹵化或帶有1至3個 下列基:氰基,硝基,羥基*捥基*胺基,羧基*胺 羰基,胺硫羰基,鹵素* C X - C s -烷基,C i - C s -鹵烷基 * C : - C β -烷羰基》C : - C s -烷礙基,C : - C β -烷»氧基, C 3 - C β -環烷基,(:i - C 3 -烷氧基> C i - C 〇 -虚烷氧基, C a - C <3 -烷氧羰基,C i - C s -烷硫基,C i - C <3 -烷胺*,二 -C : - ce -烷胺基,C i - C β -烷胺羰基,二-C i - C (5 -烷胺羰 •基,Ca-Ce -烷胺硫羰基,二- -烷胺硫羰基, C 2 - C β -烯基* C 2 - C <5 -烯氧基,苄基,笮氧基,芳基, -7 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公釐) (請先閲讀背面之注意事項再填寫本頁) 裝. -a 經濟部中央標隼局貝工消費合作社印製 經濟部中央標孪局員工消费合作社印裝 A 7 __B7_ 五、發明説明(5 ) 芳氧基,雑芳基•雑芳氧基,雑芳硫基或C ( = N 0 R a )-An-R7 ; 其中 A 係氧*硫或氮且其中之氮帶有氫或Ci-Ce -烷基; η 係0或1 ; R® 係氫或Ci-Ce -烷基且 R 7 係氫或C τ - C a -烷基, 及其鹽類。 本發明另關於製備這些化合物之方法及中間物及含有彼 等的姐合物Μ控制動物的害蟲及有害真菌。 害蟲控制之苯乙酸衍生物揭示於文獻(ΕΡ-A 422 597, EP- A 463 488 · EP-A 370 629,EP- A 460 575 * EP-A 472 300, WO-A 90/07,493, WO-A 92/13,830 > WO-A 92/ 18,48?)。 本發明之標的係提供具有改良作用之新顆化合物。 吾等已發琨此標的可藉開始定義之苯乙酸衍生物來達成 。吾等已另發現文中之其製備方法及中間物及含彼等之姐 合物可控制動物害蟲及有害真菌及其用途。 式I化合物可藉由文獻中本身已知之不同方法來獲得。 合成式I化合物不綸-C ( X ) - C 0 2 R 1基或-C Η ζ 0 N = C ( R 3 )-C(R4)=N0RB-誰先構成並無意義。 -C ( X ) - C 0 2 R 1之構成揭示於例如開始的文獻中。 合成- CH20N = CU3) -C(R4) = Ν0Ιίβ側踺的方式基本上須視 取代基R 3及R 4的性質而定。 本紙張尺度適用中國國家標準(CNS ) Α4规格(210 X 297公釐) ί^-- C (請先閱讀背面之注意事項再填寫本頁) 訂
J 306908 A7 ΒΊ 五、發明説明(6 若其中 R a 及 R 4 非歯素 * 則-C Η 2 0 N = C (R 3 ) - C (R 4 ) = N 0 R 6 之構成一般係Μ式II之笮基衍生物與式II之羥亞胺反 應來進行。 R5-ON=C(R4 )-C(R3)=NOH +
III
Ll-CH2
(R2),
-► R5-ON=C(R4)-C(R3)=NOCH/^ I
(R2)> 式中L1係親核性可取代之離去基如鹵素或磺酸翹 基團*較佳係氯、溴、碘、甲磺酸鹽、甲苯磺酸鹽或 三氣磺酸蘧。 依赫本威爾(Houben“Si/eyl)Vol. E 14b, p. 370ff 及赫本威爾* Vol. 10/1, p. 118Qff所述方法,在本 身已知方式中•於惰性有機溶劑*鹼(如氫化納,氫 氧化鉀,碳酸鉀或三乙胺)存在下進行反應。 (請先閱讀背面之注意事項再填寫本頁) 裝 訂 水 經濟部中央標準局員工消費合作社印裝
r5-l2 VI
H0N*C (R4 ) -C (R3 ) -NOH IV R5-ON=C(R4)-C(R3)=NOH III 本紙張尺度適用中國國家梯準(CNS ) A4规格(21〇Χ297公釐) 1五、發明説明( A7 B7 式VI中La係親核性可取代之離去基如鹵素或磺酸鹽 基團,較佳係氮、溴、碘、甲磺酸醱、甲苯磺酸鹽或 三氟磺酸鹽。 依赫本威爾,V 〇 1 , E 1 4 b,p . 3 0 7 f f,p . 3 7 0 f f 與 P. 385ff;赫本威爾,Vol. 10/4, p. 55ff> p. 180ff與 p. 217ff;赫本威爾,Vol. E 5, p. 780ff 所述方法,在本身已知方式中,於惰性有機溶劑,鹼 (如碳酸鉀、氫氧化鉀、氫化納、吡啶或三乙胺)存 在下進行反應。 另外,首先用二羥基亞胺衍生物IV將苄基衍生物I 轉化成對應之式V苄基肟,然後將V與產生I之親核 性經取代試劑VI反應亦可得到式I »
HON=C(R4 )-C(R3)=NOH
IV 工工 L1-CH2,
(請先閱讀背面之注意事項再填窩本頁) 裝· -9 -► 經濟部中央標準局員工消費合作社印製 R5-L2
VI 10
HON*C(R4)-C(R3)=NO-CHf^ V
(R2).
Rs-ON=C(R4)-C(R3)=NOCH I
(R2), 本紙張尺度適用中國國家標準(CNS ) Μ規格(210X 297公釐) 306S〇s A7 B7 五、發明説明(8 ) 依赫本威爾,V 〇 1 . 1 0 / 1 , p . 1 1 8 9 f f ;赫本威爾, V ο 1 . E 14b, p. 3 0 ? f f , p . 3 7 0 f f 與 p, 385 ff ;赫本 威爾,Vo 1 . 1.0/4, p . 55ff,p . 180ff 與 p. 2 1 7 f f ; 赫本威爾,V o 1 . E 5 , p . 7 8 0 f f所述方法,在本身已 知方式中,於惰性有機溶劑,鹸(如碳酸鉀*氫氧化 » 鉀,氫化納*吡啶或三乙胺)存在下進行反應。 以相似方式*由羰羥基亞胺VI與羥基胺I X a或其鹽 I X b反應亦可製備式II所須之羥基亞胺。 R5-ONH2 IXa or R5_〇NH3®QG IXb
0=C(R4)-C(R3)=N0H VII (請先閱讀背面之注意事項再填寫本頁) 裝.
、1T 經濟部中央榡準局員工消费合作社印製 -► r5-〇N=C(R4)-C(R3)=NOH III 式I X b之Q ® 係酸之陰離子,尤其係無機酸,例如 鹵化物(如氯化物)。 依 E P - A 5 1 3 5 8 0 ;赫本威爾,V ο 1 . 1 0 / 4 , P · 73ff ;赫本威爾,Vol. E. 14b, p. 369ff與 p. 3 8 5 f f所述方法,在本身已知方式中,於惰性有櫬溶 蜊下進行反應。 另外 > 首先用羰羥基亞胺衍生物W將苄基衍生物II 轉化成對應之式VI苄氧基亞胺|然後將V1D與產生I之 羥基胺I X a或其鼸I X b反應亦能得到式1 。 -1 Ί 本紙張尺度適用中國國家梯準(CNS ) A4規格(210X 297公釐)
J Α Μ Β7 五、發明説明(
0=C(R4)-C(R3)-N0H +
VII L1-CH2
(R2),
0=C{ R4 )-C(R3)=NO-CH VIII
(R2),
IXa/IXb -R5-ON=C(R4)-C(R3)=NOCH
I
(R2). (請先閱讀背面之注意事項再填寫本頁) 裝 訂 經濟部中央標準局員工消費合作社印製 依赫本威爾,Vo 1 . E 14b , p . 369ff ;赫本威爾, Vol. 10/1, p. 1189ff及赫本威爾,Vol. 10/4, p. 73『『或£?4 5 13 5 80所述方法,在本身已知方式中, 於惰性有機溶酬中進行反應。 另一種可能製備式I之方法係用Η -羥基酞.亞醢胺與 苄基衍生物I反應,接著肼解成苄羥基胺I[ a且用羰 基化合物X興K a進一步反懕。 12 本执張尺度遑用中國國家標準(CNS〉A4規格(2! 0 X 297公釐)
U I A7 B7 五、發明説明(ίο) 〇
N-OH + Li-CHj
(R2),
• m mu m i ml- (請先閱讀背面之注意事項再填寫本頁) 裝丨
Ila I R5-ON-C( R4 )-C(R3)=0 .+ X依EP-A 46 3 488,德画申請專利第42 2凡867.3所 述方法,在本身已知方式中*於惰性有機溶劑下進行 反應。藉由如對應之羥亞胺羰基化合物Via與親核性經取 代試劑VI反應得到所需之羰基化合物X。 —► Rs-0N=C(R4)-C(R3)*〇 X - R5-L2 + HON*C(R<)-C(R3)«〇 ▽I Vila
Ila HI m» nn nn nn - mt m —^ϋ n 訂 經濟部中央標準局員工消費合作社印製 or r5-onh3®q0 抑或用羥基胺I X a或其顎I X b與對應之二羰基化合 物X I反應得到所需之羰基化合物X。 / R5-ONH2 ' IXa + 0=C(R4)-C(R3)=0
XI IXb rS-0N*C(R4)-C(R3)»0
X -]3- 本紙張尺度逋用中國國家梂準(CNS ) A4規格(210Χ2<Π公釐) I五、發明説明(11 A7 B7
依 E P - A 5 ] 3 580,赫本威爾;Vol. 10/4, t>. 55ff, p. 73「f, p. 180ff及 p. 217ff ;赫本威爾* V ο 1 . E ] 4 b , p . 3 0 7 f f 及 3 6 9 f f ,赫本威爾,V ο ΙΕ 5 , p . 7 8 0 Γ f 所 述方法 * 在本 身已知 方式中 * 於惰 性有機溶劑下進行反懕。 « 對等地,首先用羥亞胺衍生物Wa將苄羥基胺la 轉化成對應之式V苄氧亞胺基衍生物,然後用如上述 產生I之親核性經取代試劑VI與V反應得到化合物I H0N=C(R4)-C(R3)=0 + H2NO-CH2
Vila
Ila
(R2), (請先閲讀背面之注意事項再填寫本頁) 裝_ 訂 -►
(R2)> C02Rl
U 水 經濟部中央標準局貝工消費合作杜印製 r5-l2
VI
依相似方式,先用式)(I之二羰基衍生物將苄基胺 14 衣紙張尺度適用中國國家梯準(CNS ) Λ4規格(210 X 297公釐) 306908 五、發明説明(12 ) A7 B7 I a轉化成苄氧基亞胺衍生物VI,然後用如上所述產 生I之羥基胺I X a或其鹽I X b與VI反應亦能製備化合 物I 。 〆(R2)m 0=C(R4)-C(R3)=〇 + H2NO-CH2
XI
Ila
C02R1 (R2).
0=C (R4 ) -c (R3) >rNO-CH2,c=x VIII I (請先閱讀背面之注意事項再填寫本頁) 裝- 、*τ IXa/IXb
k 經濟部中央標準局員工消費合作社印製 2. 其中R3及/或R4係鹵素原子之化合物可藉由本身已 知方法由其中有關基係羥基之對應先驅物得到(c f . 赫本威爾,V 0 1 · E 5 , P · 6 3 1 ; J . 0 r g · C h e πι. 36(1971), 233; J. Org. Chem. 57(1992), 3245) 〇 較佳地 > 產生鹵素衍生物之對廯反應係在i及VI階段 進行。 3. 其中R3及/或R4經由0,S或N原子踺結至分子結構 -15- 本紙張尺度適用中國國家榡率(CNS ) A4現格(210 X 297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(Ί5 ) 之化合物可藉由本身已知方法由其中有關基係鹵素原 子之對應先驅物得到(cf.赫本威爾,Vo丨.E 5 , P · 8 2 6 f f 及 1 2 8 0 f f , J . 0 r g . C h e m . 3 6 Π 9 7 1 ), 233,J. 〇rg. Cheiu. 46(1981), 3623)。較佳地,鹵 素衍生物之對應轉化作用係在I及VI階段進行。 » 4. 在某些情形中其中R3及/或”經由氧原子鍵结至分 子之化合物亦可藉由本身已知方法由其中有關基係理 基之對應先驅物得到(cf.赫本威爾,Vol, E5, p. 826-829, Aust. J. Chem. Zi(1974), 1341-9) 〇 較 佳地,產生烷氧基衍生物之對應反應係在I及VI階段 進行。 5. 得到其中R 3非鹵素之化合物,最好依EP-A 493 711所述方法用内酷ΧΠ先轉變化合物成對應苯甲酸X BI ,且經由對應之鹵化物將XIB轉變成氰基羧酸XIV( 其依品納(Pinner)反應之方式轉變(Angew. Chem- 94 (1 982), 1)成ct-_g§XV,然後再轉變成衍生物I (cf. EP 348 766, DE 37 05 389, EP 178 826. DE 3623921)° R5-ON=C () -c (R3) =NOH + _(R2)m o
X XII
本紙法尺度適用中國I)家樣準(⑽)M規格(21〇乂297公羡) - - ^—^1. --- ...... n^n 裝 !- ( (請先閱讀背面之注意事項再填寫本頁) 訂 」 A7 B7 五、發明説明(U )
Y (R2)m R5-ON=C (R4 ) -C (R3 ) =NO-CH2^^j (Hal=鹵素 COHal XIII.a R5-ON=C(R4)-C(R3)=NO-CHf
XIV
XV R5-〇N=C(R4)-C(R3)=NO-CH£
(R2), C02R (R2). R^H) (請先閱讀背面之注意事項再填寫本頁) 裝· 訂 -► R5〇N=C(R4)-C(R3)eNOCH2^
(R2). c=x C02R1
U 水 經濟部中央標準局員工消費合作社印装 依水解醋x V及產生i之接續反應之方法得到其中 R 1係氫之化合物I 。 化合物 I 係已知(E P - A 5 U 5 8 0,E P - A 4 7 7 6 3 1, ΕΡ-Λ 46 3 488 > ΕΡ-Α 370 629 ,Ε Ρ- A 4 6 0 5 7 5 )或可依 本文所述方法製備。 -17 本紙伕尺度適用中國國家揉準(CNS ) Λ4規格(210 κ 297公釐) 經濟部中央標隼局員工消费合作社印裝 306908 A7 _B7_ 五、發明説明(15 ) 由於化合物I其C = C及C = N雙鍵之原因•在製備時得到化 合物I如E/乙異構物之混合物,其可藉常用方式(如結晶 法或色析法)分離成個別化合物〇 若在合成時得到異構物之混合物•一般而言,分離非絕 對必須的,且在某些情形中個別異構物在甩於製備期或施 用期可轉變成另一個異構物(如光作用•酸或鹼下)。相 對轉變亦可能發生在腌用後,例如,植物,經處理植物或 於有害真菌或將要控制之動物害蟲的處理期間。 關於C = X雙鐽,其有關活性K化合物I之E異機物較佳 (有關- COaR1基之-0CH3,-CH3或- CH2CH3基為主之姐態) 〇 翮於-C (R3) =N0CH2-雙鐽*其有關活性Μ化合物I之順 式異構物較佳(有關-〇CH2 -基之R3基為主之姐態)。 在開始之化合物I之定義中,所用集合性術語,其一般 代表下列基: 鹵素:氣、氛、溴及碘; 糕蓽:具有1到4,6或10個碳原子之直鍵或支鐽烷基, 例如Ci-U -烷基,如甲基*乙基 > 丙基,卜甲乙基* 丁基 ,1 -異丙基,2 -甲丙基,1,1 -二甲乙基,戊基,1 -甲丁基 ,2 -甲丁基,3 -甲丁基,2 , 2 -二甲丙基,I -乙丙基,己基 ,1 ,卜二甲丙基,1 , 2 -二甲丙基,1 -甲戊基,2 -甲戊基, 3-甲戊基,4 -甲戊基,1,1-二甲丁基,丨.2 -二甲丁基, 1 , 3 -二甲 丁基,2 , 2 -二甲丁基 > 2 , 3 -二甲 Γ 基,3 , 3 -二甲 丁基,1 -乙丁基,2 -乙丁基,1 , 1 . 2 -三甲丙基* 1. , 2 , 2 -三 —1 8 - 衣紙張尺度適用中國國家標準(CNS ) Α4規格(210Χ 297公釐) --------ί 裝-- ί (請先鬩讀背面之注意事項再填寫本頁) 訂 經濟部中央標率局員工消費合作社印製 A7 B7 五、發明説明(16) 甲丙基* 1-乙基-1-甲丙基及1-乙基-2-甲丙基; 掠胺基:一種胺基,其帶有如上所述之1到6個碳原子 之直鍵或支鏈烷基; 二烷胺基:一棰胺基,其帶有如上所述之2個直鏈或支 鐽垸基,這些烷基彼此獨立且各具有1到6個碳原子; m :具有1到1 〇個碳原子之直鍵或支鍵烷基,其經 由羰基(-C0-)鐽結之該結構; 院?I基:具有1到6個或1 0個碳原子之直鍵或支鐽烷基 ,其經由楓基(-S02-)鍵結之該結構; 焼亞H:具有1到6個碳原子之直踺或支鍵烷基,其 經由亞理基(-S( = i〕)-)鏈結之該結構; 院腌羰基:具有如上所述1到6個碳原子烷胺基,其經 由羰基(-C0-)鏈結之該結構; 二捺胺羰某:每個情形中之二烷胺基*其中每個烷基具 有如上所述之1個到6個碳原子的烷基,其經由羰基 (-C0-)鏈結之該結構; 糕胺硫羰基:具有如上所述1到6個碳原子之烷胺基, 經由硫羰基(-CS -丨鍵結之該結構; 二烷胺硫羰某:每個情形中之二烷胺基*其中每個烷基 具有如上所述之1到6個碳原子的烷基*其經由硫羰基 (-CS-)鏈結之該結構; 鹵烷某:具有1到6個碳原子之直鏈或支鍵烷基•這些 基之氫原子可能部份或完全被如上所述之鹵素原子取代* '例如C , - C 2 -鹵烷基如氮甲基,二氣甲基,三氯甲基•氟甲 ~ 1 9 ~ 冬紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) (請先閱讀背面之注意事項再填寫本頁) ί 裝------訂------1 .外------
m —^ϋ nn —^ϋ nn t^n ί mK A7 B7 經濟部中央標準局貝工消費合作社印製 五、發明説明(π ) 基,二氟甲基,三氟甲基,氣氟甲基,二氯氣甲基,氣二 氟甲基,1-氟乙基,2 -氟乙基,2,2 -二氣乙基* 2,2 -三 氟乙基,2 -氯-2 -氟乙基,2 -氯-2 , 2 -二氟乙基,2 , 2 -二氯 -2 -氟乙基* 2,2,2 -三氯乙基及五氟乙基; 院氣基:具有如上所述之1到4個或6個碳原子之直鐽 或支鏈之烷基 > 其經由氧原子(-0-)鏈結之該結構,例如 CrCs -烷氧基如甲氧基,乙氧基,丙氧基* 1-甲乙氧基, 丁氧基,1-甲丙氧基,2 -甲丙氧基* 1,1-二甲乙氧基,戊 氧基,1-甲丁氧基,2-甲丁氧基,3-甲丁氧基,2,2 -二甲 丙氧基,1-乙丙氧基*己氧基,U1-二甲丙氧基,1,2 -二 甲丙氧基,1-甲戊氧基> 2-甲戊氧基,3 -甲戊氧基,4-甲 戊氧基,1 ,卜二甲丁氧基,1 , 2 -二甲丁氧基,1 , 3 -二甲丁 氧基,2 , 2 -二甲丁氧基,2 , 3 -二甲丁氧基,3 , 3 -二甲丁氧 基,1-乙丁氧基,2 -乙丁氧基* 1,1,2 -三甲丙氧基* 1,2,2 -三甲丙氧基,卜乙基-卜甲丙氧基及1-乙基-2-甲丙 氧基; 檢氣羰某:具有1到6個碳原子之直鏈或支鰱烷基,其 經由氧羰基(-oc( = o)-)鍵結之該結構; 歯烷氣基:具有1到6個碳原子之直鍵或支鏈烷基*這 些基之氫原子可部份或完全被如上所述之鹵素原子取代, 且這些基經由氧原子鍵結之該結構; 糕硫某:具有如上所述之1至4個或6個碳原子之直鍵 或支鐽烷基,其經由硫原子(-S -)鍵結到該結構 > 例如甲 硫基,乙硫基,丙硫基,1-甲乙硫基,丁硫基,1-甲丙疏 --------( 裝-- (請先閲讀背面之注意事項再填寫本頁) 、v8 」 水 本紙張又度逋用中國國家揉準(CNS ) A4規格(210 X 297公釐)
I A7 B7 五、發明説明(18 ) 基,2 -甲丙硫基,1 , 1 -二甲乙硫基,戊硫基* 1 -甲丁硫基 ,2 -甲丁硫基> 3 -甲丁硫基> 2 , 2 -二甲丙硫基,1 -乙丙硫 基,己硫基,1,1-二甲丙硫基,1,2 -二甲丙硫基,1-甲戊 硫基> 2 -甲戊硫基,3 -甲戊硫基,4 -甲戊硫基* 1,1-二甲 丁硫基,1 , 2 -二甲丁硫基,1 , 3 -二甲丁硫基,2 , 2 -二甲丁 硫基,2 , 3 -二甲丁硫基* 3,3 -二甲丁硫基,1-乙丁硫基, 2 -乙丁硫基,1,1 , 2 -三甲丙硫基,1,2 , 2 -三甲丙硫基, 1,2,2-三甲丙硫基,1-乙基-卜甲丙硫基及卜乙基-2-甲丙 硫基; 撰烷某:具有3到6個碳環員之單環烷基例如環丙基, 環丁基*環戊基及環己基; 铺某:具有2到6 β或10M碳原子且雙鏈在任何所欲位 置之直踺或支鐽烯基,例如c2-cs-烯基如乙烯基,1-丙烯 基,2 -丙烯基,1-Ζι烯基,1-丁烯基,2 -丁烯基,3 -丁烯 基,1-甲基-卜丙烯基,2 -甲基-卜丙烯基,1-甲基-2-丙 烯基,2 -甲基-2 -丙烯基,1 -戊烯基,2 -戊烯基> 3 -戊烯 基,4 -戊烯基,1 -甲基-卜丁烯基,2 -甲基-1 - 丁烯基, 3 -甲基-卜丁烯基,卜甲基-2-丁烯基> 2 -甲基-2-丁烯基 ,3 -甲基-2 - 丁烯基* 1 -甲基-3 - 丁烯基,2 -甲基-3 - Γ烯 經濟部中央標準局員工消費合作社印裝 —--------ί 裝-- 為 (請先閱讀背面之注意事項再填寫本頁)
J 基,3 -甲基-3 - 丁烯基,1 , 1 -二甲基-2 -丙烯基,U 2 -二甲 基-卜丙烯基,1,2 -二甲基-2-丙烯基,1-乙基-1-丙烯基 > 1-乙基-2-丙烯基,1-己烯基,2 -己烯基,3 -己烯基* 4-己烯基,5-己烯基,1-甲基-1-戊烯基* 2 -甲基-1-戊烯 '基* 3 -甲基-1 -戊烯基,4 -甲基-;!-戊烯基· 1 -甲基-2 -戊 -21 - 本紙張尺度適用中國國家標準(CNS ) Α4規格(210x 297公釐) 306908 A7 經濟部中央標準局員工消費合作杜印策 __B7五、發明説明(19 ) 烯基,2 -甲基-2-戊烯基,3 -甲基-2-戊烯基,4 -甲基- 2-戊烯基> 1-甲基-3-戊烯基* 2 -甲基-3-戊烯基,3 -甲基 -3 -戊烯基* 4 -甲基-3-戊烯基,1-甲基-4-戊烯基,2 -甲 基-4-戊烯基,3 -甲基-4-戊烯基,4 -甲基-4-戊烯基, 1 , 1 -二甲基-2 - 丁烯基> 1 , 1 -二甲基-3 - 丁烯基,1 , 2 -二甲 基-1 - 丁烯基,1 , 2 -二甲基-2 - 丁烯基* 1 , 2 -二甲基-3 - 丁 烯基,1 , 3 -二甲基-卜丁烯基> 1 , 3 -二甲基-2 - 丁烯基, 1,3 -二甲基-3-丁烯基,2, 2 -二甲基-3-丁烯基,2,3 -二甲 基-1 - 丁烯基,2,3 -二甲基-2 - 丁烯基,2 , 3 -二甲基-3 - 丁 烯基,3,3 -二甲基-卜丁烯基,3,3 -二甲基-2 -丁烯基· 1-乙基-1-丁烯基,卜乙基-2-丁烯基 > 卜乙基-3-丁烯基 ,2 -乙基-1-丁烯基,2 -乙基-2-丁烯基,2 -乙基-3- 丁烯 基,1,1,2 -三甲基-2-丙烯基,卜乙基-1-甲基-2-丙烯基 ,1 -乙基-2 -甲基-:!-丙烯基及1 -乙基-2 -甲基-2 -丙烯基; 揣氬某:具有2到6個碳原子且雙鍵在任何所欲位置之 直鐽或支鏈烯基*其經由氧原子(-〇-)鍵結之該結構; 摇硫某或烯腌某:具有2到6個碳原子S雙鍵在任何所 欲位置之直鍵或支鍵烯基,其經由硫原子或氮原子分刖鍵 結到烯硫基或烯胺基; 懦羰某:具有2到1 0個碳原子且雙鏈在任何所欲位置之 直鐽或支鍵烯基,其經由(-C0-)鏈結之該結構; 接某:具有2到1 0個碳原子且三鏈在任何所欲結構之直 鐽或支鍵炔基,例如C2-Ce-炔基如乙炔基,2-丙炔基, 2 -丁炔基,3 -丁炔基,1-甲基-2-丙炔基,2 -戊炔基,3- --------ί -ΐ I (請先閱讀背面之注意事項再填寫本頁) 訂 V' 夸 -22- 本紙張尺度適用中國國家標準(CNS ) A4規格(210 X 297公釐) A7 B7 經濟部中央橾準局員Μ消費合作江印裝 五、發明説明(20) 戊炔基,4 -戊炔基,1 -甲基-2 - 丁炔基> 1 -甲基_ 3 _ J快基 * 2 -甲基-3 - 丁炔基,1 ,:!-二甲基-2 -丙炔基*卜乙基_ 2 _ 丙炔基,2 -己炔基,3 -己炔基,4 -己炔*,己快基’ 卜甲基-2-戊炔基*卜甲基-3-戊炔基,1-甲基戊炔基 ,2-甲基-3-戊炔基,2-甲基-4-戊炔基,3-甲基-4-戊快 基,4 -甲基-2 -戊炔基,1,1-二甲基-2- 丁炔基,1,1 _二甲 基-3-丁炔基,1,2-二甲基-3-丁炔基,2,2 -二甲基_3_ 丁 炔基,1-乙基- 2- Γ炔基,卜乙基-3-丁炔基’ 2_乙基_3_ 丁炔基及1-乙基-1-甲基-2-丙炔基; 姑氬某或炔硫某及悚胺某:具有2到6個碳原子且三鍵在 任何所欲位置之直鏈或支鍵炔基,其經由氧原子或硫原子 或氮原子分別鍵結到炔氧基,炔硫基或炔胺基之結構; 协锻某:具有3到10個碳原子,且三踺在任何所欲位置 之直雄或支鍵炔基*其經由羰基(-C0-)鍵结到該结構; 摄锚某成孭烯ft某,搜铺硫某及現烯胺蓽:具有3到6 個碳環員之單環烯基,其經由氧原子或硫原子或氮原子直 接鍵结到環烯氧基或環烯硫基或環烯胺基之結樽例如環丙 烯基,環丁烯基,環戊烯基或環己烯基; 榻榇氬某或頊烷硫蓽及環烷胺基:具有3到δ個之碳環 員之單環烯基,其經由氧原子或硫原子或氮原子分別鍵结 到環烷氣基,環烷硫基或環烷胺基之结檐,钶如環丙基, 環丁基,環戊基或環己基; 雖雜-MAJL丄—^_遞_11_基_&_100£_基—:3 之 6 g , 飽和或部份未飽和的簞或多環糸之雑環,且帶有1到3個 -23- (請先聞讀背面之注意事項再填寫本頁) .裝---- ,-ιτ _____1 Λ1. 本紙張尺度適用中國國家梂準(CNS ) Α4规格(2丨0:< 297公釐) 經濟部中央標準局貝工消費合作社印裝 A7 __B7_ 五、發明説明(21 ) 選目氧,氮及硫之雑原子*巨其經由氧原子或硫原子或氮 原子分別直接鏈結至雜環氧基,雑環硫基或雑環胺基之結 構*例如2 -四氫呋喃基》環氧乙烷基,3 -四氫呋喃基> 2 -四氫噻吩基,3-四氫噻吩基,2 -吡咯啶基,3 -吡咯啶基 ,3 -異噚唑啶基,4 -異曙唑啶基* 5 -異啤唑啶基,3 -異噻 唑啶基,4 -異噻唑啶基,5 -異噻唑啶基· 3 -吡唑啶基, 4 -吡唑啶基,5 -吡唑啶基> 2 -聘唑啶基,4 -啤唑啶基, 5 -啤唑啶基,2 -噻唑啶基> 4 -噻唑啶基,5 -噻唑啶基, 2 -咪唑啶基,4 -眯唑啶基,1 , 2 , 4 -啤二唑啶-3 -基, 1,2,4 -噚二唑啶-5-基,1,2,4-_ 二唑啶- 3- *,1,2,4-_ 二唑啶-5 -基,1 , 2 , 4 三唑啶-3 -基,1 , 3 , 4 -聘二唑啶-2 -基,1,3, 4 -噻二唑啶-2-基> 1,3,4 -三唑啶-2-基,2,3 -二 氫呋喃-2 -基,2 , 3 -二氫呋哺-3 -基,2 , 3 -二氪呋喃-4 -基 * 2, 3-二氫呋喃-5-基,2,5 -二氫呋喃-2-基,2,5-二氫呋 喃-3-基,2,3 -二氫噻吩-2-基,2,3 -二氫噻盼-3-基, 2,3-二氫噻吩-4-基,2, 3-二氫噻吩-5-基,2, 5-二氫噻吩 -2 -基,2,5 -二氫噻吩-3 -基,2,3 -二氫吡咯-2-基,2,3-二氫吡咯-3 -基,2 , 3 -二氫吡咯-4 -基,2 , 3 -二氫吡咯-5 -基,2 , 5 -二氫吡咯-2 -基,2 , 5 -二氫吡咯-3 -基,2 , 3 -二氫 異噚唑-3 -基,2 , 3 -二氫異噚唑-4 -基,2 , 3 -二氫異啤唑 -5 -基,4 , 5 -二氬異嗶唑-3 -基* 4 , 5 -二氫異啤唑-4 -基, 4 , 5 -二氫異啤唑-5 -基,2 , 5 -二氫異噻唑-3 -基,2 , 5 -二氫 異if唑-4 -基,2 , 5 -二氫異嘧唑-5 -基,2 , 3 -二氫輿吡唑 -3 -基,2 , 3 -二氫異吡唑-4 -基,2 , 3 -二氫異吡唑-5 -基* 本紙張尺度適用中國國家梂準(CNS ) Α4規格(210 X 297公釐) --------f .裝-- I (請先閱讀背面之注意事項再填寫本頁)
、1T 1 A7 B7 五、發明説明(22 ) 4.5 -二氫異吡唑-3-基,4,5-二氫異吡唑-4-基,4, 5-二氫 異吡唑-5-基* 2,5-二氫異吡唑-3-基,2, 5 -二氫異吡唑 -4-基,2,5-二氫異吡唑-5-基,2, 3-二氫噚唑-3-基, 2 , 3 -二氫噚唑-4 -基,2 , 3 -二氫啤唑-5 -基,4 , 5 -二氫曙唑 -3 -基* 4 , 5 -二氫噚唑-4 -基,4 , 5 -二氫啤唑-5 -基,2 , 5 -二氫啤唑-3 -基,2 , 5 -二氫啤唑-4 -基,2 , 5 -二氫啤唑-5 -基,2,3 -二氫哺唑-2-基,2,3 -二氫噻唑-4-基,2,3 -二氫 噻唑-5-基,4,5 -二氫唾唑-2-基,4,5-二氫唾唑-4-基* 4 ,5 -二氩噻唑-5-基,2,5 -二氫噻唑-2-基,2,5-二氫噻唑 -4-基> 2,5-二氫噻唑-5-基,2,3-二氫眯唑-2-基,2,3-二氫咪唑-4-基,2, 3··二氫咪唑-5-基,4, 5-二氫咪唑- 2-基,4,5 -二氫眯唑-4-基,4,5 -二氫眯唑-5-基,2,5 -二氫 眯唑-2-基,2,5 -二氫咪唑-4-基,2,5 -二氫咪唑-5-基, 2-嗎啉基,3-嗎啉基,2 -六氫吡啶基,3 -六氫吡啶基, 4-六氫吡啶基,3-四氫嗒畊基* 4 -四氫嗒哄基,2 -四氫嘧 啶基,4 -四氫嘧啶基,5-四氫嘧啶基,2 -四氫吡畊基, 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 1.3.5 -四氫三哄-2-基,1,2,4 -四氫三畊-3-基,1,3 -二氫 嗶畊-2-基,1,3 -二噻烷-2-基,2 -四氫呱喃基,1,3-二氧 戊環-2-基,3,4,5,6 -四氫吡啶-2-基,4H -1,3-噻畊-2 -基 ,4H-3.1-苯并噻畊-2-基,1,1-二氧-2,3,4,5-四氫_吩 -2 -基,2 Η - 1 , 4 -笨并噻畊-3 -基,2 Η - 1 , 4 -苯并啤畊-3 -基 ,1 , 3 -二氫噚畊-2 -基,1 , 3 -二噻烷-2 -基; 每某或另氬某,努疏某,芳禳某及芳瓶某:芳族軍或多 員環系之烴基•其經由氧原子(-〇-)或硫原子(-S-)或羰基 -25- 本紙張尺度適用中國國家標準(CNS ) Α4规格(2丨0Χ 297公釐) 306S08 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明(23 ) ,(-C0-)或碓基(-S0Z-)直接鍵結之芳氧基,芳硫基,芳 羰基或芳楓基等結檐例如笨基,葵基與菲基或苯氧基,蔡 氧基及菲氧基及對應的羰基和®基; 笠芳族單或多費壞糸之烴基,其經由氮原子鐽結 到該結構; 雜芳華或雜芳-硫基,鏟关锶蠤及雜转謳某: 芳族單或多環之基團、其除了碳員環外另外可含有1到4 個氮原子或1到3個氮原子及1個氧或硫原子或1 0氣或 硫原子且經由氧原子(-〇-)或硫原子(-S-),羰基(-C0-)或 礙基(-S02-)分別直接鍵結之雑芳氧基,雜芳硫基,雑芳 羰基或雜芳砸基等結構*例如 - £=¾雜芳基二3個m鹿;:5員環之雑芳基 其除了碳原子外可含有1到3個氮原子,可含有1到 3個如環員之氮原子,例如2 -吡咯基,3 -吡咯基, 3-吡唑基,4-吡唑基,5-吡唑基,2-咪唑基,4 -咪唑 基,1 , 2 , 4 -三唑-3 -基及1 , 3 , 4 -三唑-2 -基; - 5-S雑芳某,含有1到4個氣IS孑或1到3俩想.原孑 及1個硫或氣原子或1俩氩或碕原孑:5 _氧瓌之雜芳 基其除了碳原子外可含有1到4 β氮原子或1到3個 氮原子及如遢原之1髑硫或氧原子或1画氧或硫原子 >例如2 -呋喃基,3 -呋喃基,2 -噻吩基,3 -唾吩*, 2 -吡咯基,3 -吡咯基,3 -異聘唑基,4 -異喟唑基* ' 5 -異嗶唑基,3 -異嗶唑基,4 -異噻唑基,5 -異_唑基 ,3 -吡唑基,4 -吡唑基,5 -吡唑基> 2 -啤唑基,4 -啤 -26 - 本紙張尺度適用中國國家標準(CNS ) Α4現格(2丨0 X 297公釐) (請先閲讀背面之注意事項再填寫本頁)
U 裝. ,11 五、發明説明(2〇 A7 B7 經濟部中央標準局Μ工消費合作社印製 啤 基 * 5 - 嗶 唑 基 » 2- 噻 唑 基 » 4 - 噻 唑 基 » 5- 唾 唑 基 > 2- 咪 唑 基 > 4 - 咪 唑 基 r 1 , 2 , 4- m 二 唑 -3 -基' -1 ,2 ,4 - m 二 唑 -5 -基, 1,2 ,4 -噻二 二唑- 3- 基 » 1 , 2 , 4- 哺 — 唑 -5 -基, ,1 ,2 ,4 _三唑- 3- 基 » 1 , 3 , 4- 噚 唑 -2 -基 y 1 , 3 , 4- 唾 二 唑 -2 基, * 1 ,3 ,4 -二 0$ — 2- 基 » 苯 并 稠 合 之 5 ~ i 芳 華 t 含 有 1 到 3 俩 頒. 原 子 1 俩 氛 原 子 及 / 1 俩 氧 原 子 硫 原 子 • 5 - 員 環 之 雑 芳 基 其 除 了 碳 原 子 外 可 含 有 1 到 4 個 氮 原 子 或 1 到 3 個 氮 原 子 其 如 還 原 之 1 個 硫 或 氧 原 子 或 1 涸 氣 或 硫 原 子 > 且 其 中 2 個 相 鄰 到 碳 CES m 棄 到 1 個 氮 原 子 與 相 鄰 的 碳 環 員 經 由 丁 -1 ,3 二烯- 1 , 4- —- 基 架 橋 \ 择 由 m 原 子 耩 結 5- _ 雜 芳 華 > 含 有 1 到 4 俩 m 原 子 > 或 經 由 氮 原 子 鏈 結 苯 并 稠 合 壽 之 雑 華 f 含 有 1___到 3_個 Μ 原.: 5 - 員 瑪 之 雑 芳 碁 其 除 了 碳 原 子 外 可 含 有 1 到 4 個 氮 原 子 或 如 >ΒΒΓ 還 原 之 1 到 3 個 M3 原 子 » 且 其 中 之 2 個 碳 環 員 或 1 個 氮 原 子 與 1 個 相 鄰 之 碳 TW 環 員 可 經 由 -1 ,3 二烯-1 , 基 架 橋 這 環 可 經 由 任 — 個 之 氮 環 i 鐽 結 到 該 結 構 > 看 雜 芳 華 » 含 有 1 到 3 俩 或 1 到 4 個 原 子 6 - 賢 環 之 雑 芳 基 其 除 了 碳 原 子 外 可 含 有 如 湛 原 之 1 到 3 個 或 1 到 4 個 氮 原 子 > 如 2- 吡 啶 基 3 ~ 吡 啶 基 吡 啶 基 > 3- 嗒 哄 基 » 4- 嗒 畊 基 » 2- 噃 啶 基 > 4- 嘧 啶 基 ♦ 5- 嘧 啶 基 » 吡 哄 基 » 1 > 3 , 5- 三 咁 -2 -基. * 1 ,2 ,4 哄-3 -基及1 , 2 , 4,5 -四畊-3 -基; -27- 本紙張尺度適用中國國家梯準(CNS ) Α4規格(210Χ 29了公釐) I I— I — I. - II —1 《 .i : I - (請先閱讀背面之注意事項再填寫本頁) -*
J . 306908 經濟部中央橾準局員工消费合作社印策 A7 B7五、發明説明(25 ) - 笨井琚会之B -爵雑勞某•含有1到4個氤原孑:6 -員 環之雜芳基其中2個相鄰之碳環員可經由丁 - 1 , 3 -二 烯-1 , 4 -二基架橋,如暗啉,異晻啉,喹唑啉及喹喏 啉, 或其相對應之氧基,硫基,羰基或《基; 雑芳胺基:芳族之單或多員環糸的基囿其除了碳環員外 ,可另含有1到4個氮原子或1到3個氮原子及1個氧或 硫原子且其經由氮原子踺結到該結構。 所述之部份或完全鹵化以圖表示以此方式之基團中的氫 原子可部份或完全被相同或相異之如上所述的鹵素原子取 代。 有關式I化合物其生物性的作用,以其中m係0之式I 化合物較佳。 同樣較佳的為其中R 1係甲基之式I化合物。 此外,R3係氫,羥基,環丙基,氣,甲基,乙基,1-甲 乙基,甲氧基 > 甲硫基或苯基之化合物I較佳的。 其中R 3係甲基的化合物I是另外較佳之化合物1。 此外其中R 3係甲氧基之化合物I是較佳的。 其中R 3係羥基之化合物1係額外較佳的。 此外其中R 3係氯之化合物I係較佳的。 另外其中R4係氫,羥基,環丙基,氯,甲基*乙基*異 丙基,甲氧基或甲硫基之化合物I係較佳的。 萁中R 4係甲基之化合物[係額外較佳的。 另外其中R 4係甲氧基之化合物I係較佳的 --------{.裝丨| (請先閱積背面之注意事項再填寫本頁) 、1Τ .1 束 本紙張又度適用中國國家標準(CNS ) Α4規格(2丨Ο X 297公釐) 經濟部中央標準局員工消費合作杜印製 A7 _ B7 五、發明説明(26 ) 其中R 4係羥基之化合物I係額外較佳的。 另外其中R 4係乙基之化合物I係較佳的。 其中R 4係異丙基之化合物I係額外較佳的。 其中R *係環丙基之化合物丨係額外較佳的。 g外其中R 4係未經取代或經取代之芳基或雜芳基之式I 化合物係較佳的。 另外其中R4係未經取代或經取代之吡啶基,嘧啶基,吡 哄基,嗒畊基或三畊基化合物I係較佳的。 另外其中R4係未經取代或經取代之呋喃基 > 噻吩基或吡 咯基之式I化合物係較佳的。 另外其中R 4係未經取代或經取代之啤唑基·噻唑基,異 噚唑基,異噻唑基,吡唑基或咪唑基之式I化合物係較佳 的。 另外其中R4係未經取代或經取代之晖二唑基,唾二唑基 或三唑基之式I化合物係較佳的。 其中R 4係苯基,其係未經取代或帶有1個或2個下列之 基:硝基,氰基,羥基,胺基 > 胺羰基,胺硫羰基,鹵素 ,Ca-Cf 烷基,C,-C4-_ 烷基 * Ci-Cf 烷氧基,Ci-C4-_ 烷氧基,Ci-Ci -烷胺基,二- -烷胺基,Ci-Cf烷颯 基,Ci-Ci -烷氧羰基* Ci-Cr烷胺羰基或二-C i - C 4 -烷胺 羰基之式I化合物係額外較佳的。 其中R B係氫,C , - C « -烷基,芳烷基•雜芳烷基·芳氣烷 基雑芳氧烷基,芳基或雑芳基之式I化合物係額外較佳 的。 -29- 本紙张尺度適用中國國家標準(CNS ) A4規格(210X 297公釐) n^— 1^—^i - ..... 1 = - -( I m^i f 典 (請先閣讀背面之注意事項再填寫本頁) 訂 表 A 7 B7 五、發明説明(27 ) 另外R ί ’係C 1 - C β -烷基之式[化合物係較佳的。 其中R e係甲基或乙基之式I化合物係額外較佳的。 另外R s係芳烷基或雜芳烷基之式I化合物係較佳的。 其中R 5係芳氧烷基或雜芳氧烷基之式I化合物係額外較 佳的。 其中R β係芳基或雜芳基之式I化合物係額外較佳的。 另外其中X係Ν 0 C Η 3之式[化合物係較佳的。 另外其中X係C Η 0 C Η 3之式I化合物係較佳的。 另外其中X係C H C Η 3或C H C H 2 C Η 3之式1化合物係較佳的 〇 有關式I化合物之用途,下表的式I化合物係特較佳的 表 1 通式I ,1之化合物,其中(R2)ra係氫且取代基R3,R4及 R β之姐合可供表A各對應情形之化合物 (請先閱讀背面之注意事項再填寫本頁) 裝. 訂
och3 co2CH3 I. 象 經濟部中央標準局員工消賢合作社印焚 表 2 通式I . 1之化合物,其中(R 2 ) 係氯且取代基R R s之姐合可供表A各對應情形之化合物。 表 3 -30 本紙張尺度適用中國國家梂準(CNS ) A4規格(210X 297公釐) A7 B7 五、發明説明(28 通式I . 2之化合物 > 其中(R 2 ) ra係氫旦取代基R 3,R 4及 之姐合可供表A各對應情形之化合物。 R3 (R2), r5on.
NO-CH2 j , CH-. C=CH R4 co2ch3 表 4 通式I . 2之化合物,其中(R 2 ) „係氯且取代* R R5之姐合可供表A各對應情形之化合物。 表 5 通式I . 3之化合物,其中(R 2 ) „係氫且取代基R R 5之姐合可供表A各對應情形之化合物。 R4及 R4及 --------1 .裝— - (請先閲讀背面之注意事項再填寫本頁) 訂
ch2ch3 CO2CH3 1.3 永 表 6 通式I . 3之化合物,其中(R 2) „係氯且取代基R R 6之組合可供表A各對應情形之化合物。 表 7 通式I . 4之化合物•其中(R 2 ) «係氫且取代基R R s乏姐合可供表A各對應情形之化合物。 -3 1- 本紙浪尺度適用中國國家梂準(CNS ) A4規格(210/ 297公釐) 及 經濟部中央標嗥局貞工消費合作社印放 A7 B7 五、發明説明(29 r5on
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A B 五、發明説明(U1 ) 經濟部中央標準局員工消費合作社印裝 m CC m 1 c〇 -基 m 1 co t* l 1 涯 1 裝 1 装 1 逋 m 1 CO 1 r-H 1 K 補 1 CM 1 H m i CO 1 1 權 1 CNj 1 卜 m 3: U 31 1 m 1 »H 1 CO 1 1 m X 卜 X X c; t ry •H X -烯 緘 1 r-i co 1 1 m »-H 1 t 褒 fr n S CJ W) s cT c!T nl c!? 1 1 -~x 笾 fr 1 w K ω E 1 <*0 X 1 W m 濉 I w K E * n SC I ac CJ 1 sc 1 s: MB a 33 U 1 3: c!? I X va V X c? f X 1 0 1 X CJ ac • 0 1 X a i X a ( K cT 秦 X WS a 1 m m 猢 權 m « m m m m m m 凍 α: 雜 m 禳 镞 癥 m m m 雜 m 鐮 m 通 媒 雜 m 逛 猫 起 装 m 猫 逛 盎 猫 m 盜 猫 猫 逛 猫 涅 挺 Br fr fr fr Sr fr fr Er Br Br EE- ffih fr fr Sr 5- Br • η 1 cn n 1 n Π 1 11 1 <n 丨1 1 n H 1 ll i Π 1 n I il 1 Π 1 •ψ 1] 1 ll 1 u 1 11 1 !I 1 嚤 11 1 η Ο: 〇 ch3 »n S 〇 <·» s o _1 X a λ 33 〇 ch3 m X <n X 3C 〇 n X U 3? 〇 |ch3 ) fn S υ ^_ n X υ • 0 as 〇 CN <N iN rj m CN <N n K〇 <N r· <N ω <N Ol o «*1 — r> CN rn n m 胷 (Λ <n Ζ <N 04 <N <N <N <H Ol <N <N ΓΊ (N <N <N <N (N <N *144- I--------^ --《^ (請先閱讀背面之注意事項tk本頁) 訂 」 本紙張尺度適用中國國家標準( CNS ) A4現格(210X 297公釐) B7___— — 五、發明説明(142) 化合物I適宜作為殺真菌餌1 ° 以顯著對抗廣泛植病真菌,特別對囊子菌縟(Ascorayc_ etes)及擔孢子_網(.Basidiomycetes)之活性區別化合物 I 。彼等在某些情形中有全面活性且用作為葉及土壤之殺 真菌劑。 彼等化合物對於控制不同農作物之多重真菌特別重要’ 這些農作物如小麥*黑麥,裸麥*燕麥,米*玉米,青草 ,棉花,黃豆,咖啡,甘Μ,水果及裝飾植物與蔬菜如胡 瓜,豆及南瓜,及這些植物的種子。 彼等化合物特別適用控制以下植物疾病:毅類之白粉病 ,甜菜之白粉病,瓜之白粉病,蘋果之白粉病,葡萄之白 粉病,毅類之銹病,棉花之根腐病,甘蔗及殺類之黑櫳病 蘋果之黑星病(斑點病),親類之斑黏病小麥之穎枯病, 草莓及葡萄之灰徽病,落花生之褐斑病,小麥及裸麥之褐 斑病,米之稻瘟病,馬羚薯及蕃茄之晚疫病,不同種植物 之枯萎病,葡萄之霜霉病,水果及蔬菜之斑黏病。 化合物I係用殺真菌有效之活性成份處理輿菌或欲保!! 不受興菌侵襲之種子,植物,材料或土壤。彼等化合物可 使用于受真菌慼染前或後之材質,植物或種子。 彼等化合物可轉變成常用組合物如溶液、乳蜊、懸浮液 、塵削、粉蜊、糊蜊與粒蜊。所用削型端賴待刖所欲之用 途而定。在任何情形中,需保證使苯乙酸衍生物之微細及 均勻分散才行。以已知的方法製備姐合物如以溶劑及/或 載削延展活性化合物,視浦要甩乳化劑及分散劑;若以水 -14 5-
本紐又度逋用中國國家縣(CNS ) Α4规格(2!〇X 297公釐) 五、發明説明(U5) A7 B7 為稀釋劑時,則亦可用其它的有櫬溶劑作為輔助性·溶m。 適合作為本目的之輔肋性溶劑如芳族(如,二甲苯} 化芳族(如’氯苯),石撇(如,粗製油體_份),酵類 (如 > 甲醇’ 丁酵),_類(如,環己_),胺頫(如, 乙酵胺,二甲基甲醯胺)及水;載劑如土壤中之天然碟物 (如高嶺土’礬土’滑石及白堅)及土壤合成性礦物(如 ,高分散性之矽酸及砂酸H),乳化劑如非離子性及陰離 子性乳化劑(如聚氧乙烯腊肪醇醚,烷磺酸_及芳磺酸_ )及分敗劑(如木質素亞硫酸化物之顢液及甲基嫌維素) 一般而言》殺真菌姐合物含有0.1至95,較佳為量0.5 至9 0重量百分比活性成份。 依所要效果之類型,施用速率為每公頃0.01至2.0公斤 之活性化合物。 當用活性成份治療種子時*其董通常每公斤需用0.001 至0.1克,較佳為0.01至0.05克。 當本發明之組合物用作為殺真菌劑時•其可與如殺草削 、殺蟲劑、生長調節素,殺真菌繭或另用肥料一起使用。 為與其它殺真菌劑混用時,殺真菌作用範隨在許多例子 請 先 閲 讀 背
項 I 旁 裝 訂 經濟部中央標準局員工消费合作社印製 僅 孅贰 但 酸基 , 甲乙 用:胺亞 腌制硫, 靼限二綷 一何基酸 物任甲甲 合作二胺 化來如硫 明用,贰 發非物基 本而生乙 與物衍亞 可合其 , 蜊姐及鋅 菌之醋酸 真能酸甲 殺可甲胺 之明胺硫 。列說硫二 加所來二基 增列用*甲 會下是疏二 中 只 > 本紙張尺度遙用中國國家橾準(CNS )八4规格(21 Ο X 297公釐)
I A7 B7
經濟部中央標準局員工消費合作社印U 五、發明説明(1料) 硫 胺 甲酸 鎂,亞甲 过 - 二胺贰二 硫胺甲酸鎂鋅 > 四甲 基硫胺 甲 醯 贫 一 硫化物* Ν , Ν ’-亞 乙基贰 硫 胺甲酸 鋅之氨錯合物 » N, N ’ -亞丙基贰硫胺 甲酸 鋅之氨 m *曰 合物> Ν,N,-亞 丙基贰 硫 胺甲 酸鋅及N > Ν’- 聚亞 丙基贰 (硫胺甲釀基)二硫化合 物 » m 基衍 生物,如 二硝基( 1 -甲庚 基 )苯基丁烯酸酿 ,2-第 二 丁 基-4 ,6 -二硝苯基 3,3 -二 甲基丙烯醋 2 -第二 丁基 -4 ,6 -二硝苯基異丙基 碳酸 酯及二 異 丙基5- 硝異酞酯; 雑 環物 質,如2 - 十t基咪唑 -2- 基 乙酸醋 ,2,4-- 二氯 -6 -(鄰-氯苯胺并) -S- 三畊 ,0 酞 亞醢胺 膦酸硫酸二乙 酯 5-胺 基-1-[贰 -(二甲胺基 )氧 m 基]-3- 苯基-1 , 2 , 4-三 唑 2,3 - 二氰基-1 ,4- 二硫 Μ晻嗣 2-硫基 -1,3 -二 硫基 [4 ,5 -b ] II奎噚啉,甲基 卜(丁胺 甲醯基)-2-苯眯唑胺 甲酸甲 醋 2-甲 氧羰胺苯 并咪唑, 2 _ (呋 哺 -2-基) -苯并咪 唑, 2- 00 1唑- 4 -基)-苯 并咪唑, Ν ~ (1 , 1, 2 , 2-四 氣乙硫基)四氫 酞 亞 醯胺 ,N-三氯 甲硫四氫呔 亞醯胺,N -三 三氯甲硫 肽适醢 胺 N - 二氣 氟甲硫基 -N , Ν ’ -二甲 基- N- 苯硫酸 二醣胺, 5-乙 氧 基 -3-Ξ ΐ氯甲基- 1 , 2 ,3-_ 二 唑 2 -硫《氧甲硫苯 并噻唑 » 1 , 4 -二 氯-2, 5' 二甲 氧基 梁 , -45» ’ 4- (2 -氯苯亞阱基)- 3 -甲基 -5 -異嗶唑嗣,2 -硫吡 啶-1 -氧 化物 8 -羥基《 _及 其飼髖 * 2 , 3-二 氫-5-羧醣苯 胺基 -6- 甲基- 1,4- m 噻炔* 2 3 - 一 氫 -'5 -狻醢苯胺基- 6 -甲基-1 . 4 -啤 噻 炔* 4, 4 -二氣化物, .2- 甲 基-5 ,6-二氫- 4 Η - 哌喃 -3- 羧醯苯肢基 2-甲基 呋喃 -1 4 7 ~ 本紙張尺度適用中國國家標準(CNS ) A4規格(210X 297公釐)
經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(145) -3 -羧醯苯胺基,2 , 5 -二甲基呋喃-3 -羧醯苯胺基> 2 , 4 , 5 -三甲基呋喃-3 -浚醯苯胺基,2 , 5 -二甲基-N -環己基呋喃 -3 -羧醯胺,N -瓌己基-N -甲氧基-2 , 5 -二乙呋喃-3 -羧醯胺 ,2 -甲醯苯胺基,2 -吲哚醣苯胺基,N -甲醯基-N -嗎啉 -2 , 2 , 2 -三氯乙基縮醛,六氫吡畊-1 , 4 -二基贰-(1 - ( 2 , 2 , 2 -三氯乙基)甲醯胺),1-(3,4 -二氯苯胺基)-1-甲醣胺基 -2,2,2 -三氯乙烷,2,6-二甲基-N-十三基嗎啉及其软, 2 , 6 -二甲基-N -環十二基嗎福啉及其醱,N - [ 3 -(對-第三-丁苯基)-2 -甲丙基]-順-2 , 6 -二甲基嗎福啉,N - [ 3 -(對-第三-丁苯基)-2 -甲丙基]-六氫吡啶,1-[2-(2,4-二氮苯 基)-4 -乙基-1,3-.二氧戊璁-2-基乙基]-1 Η-1,2,4 -三唑, 卜[2 - U , 4 -二氯苯基)-4 - £ -丙基-1 , 3 -二氧戊環-2 -基乙 基]-1 Η - 1 , 2 , 4 -三唑,Ν -(正-丙基)-Ν - ( 2 , 4 , 6 -三氯苯氧乙 基)-Ν’ -咪唑腺,卜(4 -氯苯氧基)-3,3 -二甲基-1 - (1 Η - 1 , 2,4 -三唑-卜基)-丁 - 2-嗣,卜(4-氯苯氧基)-3,3 -二甲基 -1-(1丨彳-1,2,4-三唑-1-基)-了-2-醇,€(-(2-氯苯基)-〇{ -(4 -氣苯基)-5 - _啶甲酵,5 - 丁基-(2 -二甲胺基)-4 -羥基 -6 -甲基嘧啶,贰-(對-氯苯基)-3-吡啶甲酵> 1,2-贰-( + 3-乙氧羰基-2-硫腺基)-苯,1,2 -贰- (3 -甲氧羰基-2-硫腺 基)-苯* 及不同的殺真菌劑如+二胍乙酸醋,3 - ! 3 - (3 , 5 -二甲基 -2 -氧環己基)-2 -羥乙基:1-麩醢胺基,六氫苯,DL -甲* -N-(2,6 -二甲苯基)-N -呋喃-2-基鋁氫化物*甲基DL-H-( 2,6-二甲苯基)-«-(2’-甲氣乙醚基)-鋁氫化物,《-(2,6- -14 8- 本紙張尺度適用中國國家揉準(CNS ) A4规格(210X297公釐) ic裝! (請先閱讀背面之注意事項再^'本百) 訂 水 ---B7 __ 五、發明説明(us) 二甲苯基)~N -氧乙醢基—DL-2 -胺了内釀,甲基DL-N-(2,6 _一甲苯基(笨乙釀基)-鋁氫化物,5 -甲基-5-乙烯基 -3 - (3,5 -二氣笨基)-2 , 4 -二氧基-1 , 3 -噚唑啶,3 - [ 3,5 -二 氣苯基」_ 5 -甲基-5 -甲氧甲基-1,3 -噚唑啉-2 j -二酮, 3 - ( 3,5 -二氡笨基卜異丙胺甲醢乙内醢腺,n - (3 * 5 -二氯 苯基)-1,2-二甲環丙烷-12-二羧亞醯胺* 2-氰基-[N-(乙 胺羰基)-2 -甲氧亞胺:j-乙醯胺,ι-[2-(2,4-二氯苯基)戊 基]-1 Η - 1, 2 , 4 -三唑,2 , 4 -二象-α - (1 H - 1,2,4 -.三唑-卜基 甲基)-二苯甲基酵,Κ3 -氣-2,6 -二硝基-4-三氟甲笨基 )-5 -三氟甲基-3_氣—2 -胺綦吡啶,及卜((贰- (4-氣笨基 )-甲矽烷基)-甲基)_]^-1,2,4-三唑。 式I之化合物另適於有效控制害蟲如毘巖,蜘蛛類節肢 動物’線蟲。逭些化合物可用在般類保護環埦衛生*貯有 保護及獸«部份中當作殺害巋蜊。 有害蟲昆蟲包括:鱗翅目(Lepidoptera)之有害動物實 例為:小地老虎(Agrotis ypsilon),黃地老虎(Agrotis segetum) , Alabama argillacea,黎豆夜蛾(Anticarsia gemmatalis),藏實巢蛾(Argyresthia conjugella) ’ Y 紋夜蛾(Autograph a gamma)’ 松尺蝴(B up alus piniari** 經濟部中央標率局員工消費合作社印装 us ),捲葉蛾(Cacoecia mu r ί n a n a ),Capua reticulana. Cheimatobia brumata ,雲杉捲窠蛾(Choristoneura furaiferana),西方雲杉捲絜(Chorist〇neura occidental fs ) , 美洲粘蟲 (Cirphis unipunct a) , 蘋果蠢蛾 (Cydia pomonella),歉洲松毛淼(Dendrolinus pini), -149- 本紙張尺度適用中國國家標準(CNS ) A4規格(2丨0X297公釐) B7 五、發明説明(U7) 7 里螺(〇Iaphania nitidalis),巨座玉米螟(Diatraea srandUseila),埃及金剛纘(Earias Usuiana),小玉 米摂(Elasm〇palpijS iignoseiius),gup〇eciiia ambig-uella Evetria bouliana,粒庸地老虎(Felt丨a subte-rranea) ’大蠘螟(Galleria μ丨丨〇nena),李小食心蟲 4 (Grapholitha funebrana),梨小食心蟲(Graph〇iitha molesta)梅转蟲(Heliothis armigera),美洲SI夜蛾 (Heliothis virescens),玉米穗夜蛾(He 丨丨〇this ’菜摂(Hellula undalis),Hibernia defoliaria,美國 白蛾(HyphantrU cunea),蘋果巢蛾(Hyponomeuta malinellus),番 Jg 蠢蛾(Keiferja iycopers{ceiia), 截杉尺蠖(Lambdina fiscellaria),甜菜夜蛾(Laphygma exigua),咖啡一點潛蛾(Leucoptera coffeella) * 旋紋 潛葉蛾(Leucoptera scitella),細蛾(Lithocolletis blancardella),i.obesia bot「ana,黃綠條螺(Lox〇ste- ge stictical is) * 舞骞蛾(Lyraantria dispar) ·偺后毒 蛾(Lyraantria monacha)窄翅潛娥(Lyonetia clerkelia 經濟部中央橾準局貝工消费合作社印裝 ),天幂毛蟲(Malacosoma neustria) * 甘藍夜蛾(Ma||le_ stra brassicae),_麥_ 蛾(〇mia Pseud〇tsugata) » 歡洲玉米娱(Ostrinia nubilaHs)’Panolis 紅羚蟲(Pectinopliora gossyp 丨 ella)’ S 雑角夜蛾 idroma saucria)» 天社蛾(Phalera biicephala},馬卜替 塊楚蛾(Phthorimaea operculella) ’ Phyll〇Cn!stis c i tre 1 U,大菜粉蜾(P Ur ί s brass icae),p lath J p 6 n a -150- 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公着) A7 B7 五、發明説明(U8) scabra,小菜蛾(Plutelu xy 丨〇steMa),大豆夜蛾 (Pseudoplusia includens) · Phyacionia frustrana «
ScrobipalpuU absoluta,麥蛾(Sit〇tr〇ga Ce「eaier^_ la),葡萄長鬚捲《峨(Ί . , . .,, . ^ 項 is 系 mi6pargan〇this pilleriana),草地 粘蟲(Spodoptera frugiperda),斜紋夜蛾(Sp〇d〇pte「a
I 1 1 t u r a ),s P 0 d 0 p r· e r a 11 o r* a i i s ,大頭啸蠅(Th a u »a t _ opoea Pity0caiapa) ’ 棟綠捲絮蛾(T〇rtrix viridana), 粉紋夜蛾(TrUhopUsU ni)及雲杉小捲絜蛾(26丨「34-era canadensis) 〇 鞘翅日(Coleopi:e「a)之實例為:梨長吉丁(Agr i Us sinuatus)具條叩甲(Agri〇tes Hneatus),麥金針裊 Usriotes obscurus),六月金龜子(Aniphiraallus solstitialis) ’ Anisandrus dispar*,棉玲象甲(Antho-noraus grandis) ’ 蘋祀象甲(Anthonomus pomorum), Atomaria linearis’ 溶小蜂(Blastophagus piniperda) ’Blitophaga undata,蚤豆象(Bruchus rufiaanus),这 象(Bruchus pisorum) , Bruchus lentis , IS果捲M 象甲 (Byctiscus betulae),龜甲(Cassida nebulosa) , 1¾ 絜 甲(Cerotoraa trifurcata),甘藍萊象甲(Ceuthorrhyn-chus assirailis) * 象甲(Ceutorrynchus napi),甜菜脛 跳甲(Chaetocnema tibialis),煙草金針 ft(Conoderus vespertinus),天門冬夜甲(Crioceris a s p a r a S i) * 長角 M 甲(Diabrotiea longicornis),十二星瓜聚甲(Diab- 'rotica 12-punctata), 玉米根M 甲 (Diabrotica virgi- -1 5 1 本紙張尺度適用中國國家標準(CNS ) Α4規格(2丨0 X 297公釐) 請 先 閲 讀 背 ir 之 注 意 事 項 本衣 頁 訂 經濟部中央棣窣馬興Μ消費合作注印狄 A7 B7 經濟部中央懞隼馬貝工消費合泎汰印焚 五、發明説明(H9 ) fera),墨西哥豆雜盡(Epilachna varivestis),煙草跳 甲(Epitrix hirtipennis) , Eutinobothrus brasilie- nsis’ 象甲(Hylobius abietis),埃及苜猜象甲(Hypepa brunneipennis),苜猜絮象甲(Hypera postica) * 松小蠢 (I ps typographus) * 負?尼 §(Leraa b i1 i n ea t a , Lena * melanopus),馬龄薯甲蟲(LePtinotarsa decemlineata) * 甜菜金針蟲(Limonius californieus),稻象甲(l】’ss-orhoptrus oryzophi ius),叩甲(Melanotus c〇 nuaun i s),
Meligethes aeneus * 蹈金龜(Melolontha hipp0casta- ni» Melolontha raelolontha) , 0 u 1 e ma ory 乙 sie ,象甲 (Ortiorrhynchus sulcatus),草莓根象甲(Oti〇rrhyne-hus ova’tus) * 猿葉患(Phaedon cochleariae),跳甲 (Phyllotreta chrysocephala),鳃金龜饜(Phy]l〇phaga sp.),庭園麗金龜(Phyllopertha horticola),藤臂淡 足跳甲(Phyllotreta nemorMim),黃曲條跳甲(Phyllotr-eta striolata),日本麗金龜(Popillia japonica),豌 豆葉象甲(SUona lineatus)與谷象(Sitophilus gran-aria); 雙翅目(Dipt era)之實例為:埃及斑蚊(々6(168368¥9-ti) * Aedes vexans,墨西哥楠實撕(Anastrepha ludens ),五斑按蚊(Anopheles raaculipennis),地中海實撕 (C e r a t i t i s capitata),Chrysoraya bezziana,C h r y s o -mya· hominivorax,Chrysomya raacreilaria * 高梁期蚊 (Contarinia sorghi(:〇la),糞撕(Cordyiobia anthro- 152- 本紙张尺度逋用中國國家標準(CNS ) A4规格(210X297公釐) (請先閱讀背面之注意事項再i4寫本頁)
L -訂- A7 B7 經濟部中央樣隼馬員工省费合阼达印11 五、發明説明(15〇) pophaga),庫蚊(culex Pipiens),瓜實蠅(Dacus cucurbit ae) » 油橄攬實蠅 (Dacus 〇ieae) , 蕾苔莢期蚊 (Dasineura brassicae),黃腹族撕(Fannia canicular二 is) * 大馬窗撕((jaster〇philus intestinalis),Gloss-ί π a morsitans, Haematobia i r r i t a n s , Haplodiplosis equestris,種撕(Hylemyia platura),紋皮撕(Hypo-derma lineata) , 潛萬撕 (Liriomyza sativae) , 三繁潘 挪(Liriomyza trifolii),綠棚(Lucilia caprina), Lucilia cuprina絲光綠嫌(Lucilia serieata),尖眼 If 蚊(Lycoria pectoralis),瘿紋(Mayetiola destructor ),家撕(Musca domestica) » 廐麻嫌(Muscina stabul-ans),羊鼻級(Oestrus ovis),瑞典嫌(Oscinella frit),甜菜潛葉撕(Pegomya hysocyami, Phorbia a n t i q u a , P h o r b i a brassieae,Phorbia coarctata),櫻 桃實挪(Rhagoletis cerasi) * 蘋實級(Rhagoletis poraonella),牛蛇(Tabanus bovinus),大蚊(Tipula oleracea)及歃洲大蚊(Tipula paludosa); 纓翅目(Thy sa nop t era)之實例為:煙草裼酹馬(Fra nk-liniella fusca)» 苜糖 M 馬(Prankliniella occidental i s) , 花薊騄 (Frank 1 in iel U t「itici ) ,橘實薊馬 (Scirtothrips citri) ·稻 ίί 馬(Thrips oryzae),檢槲 酹馬(Thrips palmi)及煙草薊馬(Thrips tabaci); 膜翅目(Hyiaenoptera),例如:黄翅罙葉蜂(Athalia "rosae),切絮嫌(Atta cephalotes, Atta sexdens),德 -153- (請先閲讀背面之注意事項I寫本頁) :裝. 訂 U. 本紙張尺度適用中國國家梯準(CNS ) A4規格(210 X 297公釐) A7 B7 _ 五、發明説明(151) /+(切萬嫌(Atta texana) * 壤條(Hoplocampa fflinuta) * ϋ 實葉錄(Hoplocampa testudinea),廚蟻(M〇nomo「ium pharaonis),火儀(Solenopsis geminata)及外引紅火嫌 (Solenopsis i n v i c t a ); 異翅目(Heteroptera),例如:喜綠蝽(Acrosternum i hilare),玉张長蝽(Blissus leucopterus),煙草黑斑盲 蝽(Cyrtopeltis notatus),棉紅蝽(Dysdercus cingd- a t u s ) » i# (Dysdercus intermedius) ^ Jgi# (Eurygas-ter integriceps) , Euchistus impictiventris, M 足綠 勝(Leptoglossus phyllopus)’ 牧草盲錄(Lygus llneo-laris),牧草盲擦(Lygus pratensis),稻綠擦(Nezara viridula),甜菜擬網蝽 (Piesma quadrata),So l ubea insularis 及 Thyarita perditor ; 經濟部中央標準局負工消费合作社印製 同翅目(Homoptera),例如:無網長管蚜(Acyrthos-iphon onobrychis),落葉松球蚜(Adelges laricis) * Aphidula nastur*t.:ii * 蚕豆蚜(Aphis fabae),薄果姆 (Aphis p o m i) » Aphis sa mb uc ί » ϋ 短尾扮(Brachy-ca udus cardui) » ^ M tf (Brev i coryne brass i cae), Ceros i pha gossypii. Drey f us i a nordmann i anae, Dreyfusia piceat"圚尾蚜(Dyasphis radicola), Dysaulacorthum pseudosolani,蚕亘微葉蠓(Enpoasca f abae),麥長管蚜(Macros ί p K u m avenae),大戟長管蚜 (Microsiphum euphorbiae),餺務長管扮(Macrosiphun rosae),蚕亘修尾蚜(Megoura viciae),轚薇麥蚜 Ί 5 4 - 本紙張尺度適用中國國家梂準(CNS > Α4规格(2丨0X297公釐) 五、發明説明(152) (Metopolophiura dirhodum) , Myzodes persicae,樱桃黑 瘤額扮(Myzus cerasi),稻褐飛虱(Nilaparvata lugens ),萵苣根簡棉蚜(Pemph Uus bu「sar ius),蔗飛虱 (P e r k i n s i e I 1 a s a c c h a r i c i da ) * § iH (Phorodon humuli),鍊木風(ps.ylla mali),木風(Psylla piri), Rhopalomyzus ascalonicus ,玉米溢管姆(1?11〇?31〇81口-hum maidis) > 扮(Sappaphis mala),顏果姆(Sappaphis mali),麥二叉婉(Schizaphis graminum) * Schizone-u r a lanuginosa* 溫室白粉虱(Trialeurodes vaporar-iorum)及葡萄根癯蚜(Viteus vitifolii); 等翅目(Isoptera),例如:Calotermes flavicollis, Leucotermes flavipes,白樣(Reticuiiterraes lucifu-gus) & Terries n a t. a 1 e n s i s ; 直翅目(Orthoptera),例如:家蟋摔(Acheta domest-ica),東方小蠊(Blatta orientalis),徳國小蠊(Bla-ttella germanica),歒洲球嫂(Porficula auricularia ),歐洲螋姑(Gryllotalpa gryllotalpa),飛鏟(Locu-s t a migratoria) ' 雙帶炸磁(M e1 a η ο p 1 u s bivittatus) * 赤腿蚱蜢(Melanoplus femurrubrum),墨西哥昨蜢 經濟部中央標準局貝工消费合作社印策 (Melanoplus mexicanus) ’ 通徒作猛(Meianopius Sang-uinipes),洛硪山蚱蜢(Melanoplus spretus),紅翅蜷 (Nomadacris septemfasciata) ’美洲大蠊(Periplan-eta ameri cana) · ^ U (Schistocerca americana) * 蚱蜢(Schistocerca peresrina),天社蛾(Staurono- -1 55- 本紙張尺度適用中國國家標率(CNS ) A4規格(21 〇 X 297公釐) 五、發明説明(155) A7 B7 tus maroccanus)及溫室翅摔(Tachycines asynamorus 經濟部中央標準局員工消费合作社印製 姝形網(Arachno idea),例如:螝蟎目(A carina),如 美洲花蜱(/Ublyorama amerMcanum),花蜱(Amblyomma variegaturo),波斯 ® 喙蜱(Argas persicus),具瓌方頭 iM (Boophilus annulatus) > 蛛(Boophilus decoloratus ),微小牛蜱(Boophilus microplus),短須钃(BreviPa_· lpus phoenicis) * 苜猜笞嫌(Bryobia praetiosa),矩 頭蛛(Dermacentor silvarum),媒耳櫪東方葉嫌(E〇tet-ranychus carpini),權鳒(E「i〇phyes sheldoni), Hyalomma truncatum,羊硬蛛(Ixodes ricinus) » 婢 (Ixodes rubicundus),嗓蛛(Orn i thodorus mo u b a t a ) * 耳殘嚷蛛(Otobius megnini),梅旁葉鳒(Paratetran-ychus pilosus) » Dermanyssus gallinae ,檐輯嫌 (Phyllocoptruta oleivora,側多食肤嫌蟎(p0.lyphago-tarsoneraus 1 atus),羊痛鳒(Psoroptes ovls),扇頭蛛 (Rhipicepha 1us appedίculatus ),扇頭蜱(Rhipicepha-lus evertsi) » Sarcoptes s c a b i e ί ,朱砂 MS|(Tetra- nychus cinnabar'inus),紅葉嫌(Tet ran ychus kanzawai )*太平洋紅葉痛(T e t r a n y c h u s p a c i f i c u s ),棉紅蟎 (Tetranychus teiai-ius)* 及棉絮蟎(Tetranychus u r t ί c a e ); 線蟲網,例如根瘤嫌裊類*例如:馬柃If根線裊(Mel- oidogyne hapla),花生根結嫌 ft (Meloldogyne incogn- 1 56- 本紙張尺度適用中國國家梂準(CNS ) Α4规格(2丨0 X 297公釐) 請 先 閱 面 之 注 項 旁〆裝 Jr η 产 A7 B7 經濟部中央標率局貝工消費合作社印製 五、發明説明(154 ) ita), Meloidogyne javanica,形成孢囊之線應類:例如 :球線蟲(Globodera rostochiensis),異皮線 erodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii),及莖與葉之嫌蟲如 :Belonolairous longicaudatus,馬鈴薯 M 線巖(Dity- t lenchus destructor),甘薯莖線 H(Ditylenchus dipsaci), Hel iocotylenchus multicinctus, Lo n s i d -orus elongatus,穿孔媒盡(Radopholus siraiiis), Rotylenchus robustus,尾線& (Trichodorus primiti-vus) * 根結線蟲(Tylenchorhynchus claytoni, Tylenc-horhynchus dubius) ·小麥線惠(Pratyienchus negle-ctus) * 根腐線蟲(Pratylenchus penetrans),咖啡游離 根線巖(Pratylenchus curvitatus),及 Pratylenchus s ο o d e y i ° 該等活性化合物可以例如:其本身形式使用,或以其製 得之姐合物形式或腌用形式使用,例如:可直接哦蠢之溶 液,粉劑,懸浮液或分敗液,乳液,油分散液*糊繭’撒 粉蜊,撤播劑*或粒繭供嗔灑,哦霧,撖粉,撖播或驪水 用。其施用形式完全依製劑之使用目的而定,但必須確使 根據本發明活性成份盡可能形成最均勻分佈。 在立即可施用製劑之活性化合物濺度可在實質範園中有 所變異。 一般,彼等係0.0001至10« ,較佳為0.01至1¾° 活性化合物很成功用於超低量方法(u L V ),若有可能® -1 57- 本紙張尺度適用中國國家梂準(CNS ) A4規格(2ΙΟΧ2ί>7公釐) (請先閲讀背面之注意事項再填寫本頁)
V 裝. 訂 加 遘尚 添 至 時, 須 1 液¾ 無 ο 散柴 至 係 分¾ 甚 率 油^ , 用 及煤 物 拖 蜊,, 合 之。糊如 姐 物頃,份 之 合公液槪 份 化 \乳油 成性斤,物 性活公液礦 活 之 ο 溶之 比 篇1之黏 分 害至用-沸 百。制 2灑度 量物控 ο 哏高 重合下為接至 95化形佳直度 過性情較供中 超活外,備用 含之戶 ο 製使 用劑 2 於 經濟部中央梯準局貝工消费合作社印製 Α7 Β7 五、發明説明(1 55 ) 可使用煤焦油類,及植物油或動物油,脂系,環糸與芳香 糸烴類如:苯,甲苯,二甲苯,石蟣,四氫萘 > 烷基化萘 類及其衍生物,甲醇,乙酵,丙酵,丁酵,氣彷,四氣化 碳,環己醇*環己_,氣笨,異佛爾嗣,及強極性溶劑如 :二甲基甲醯胺,二甲亟楓,N -甲基吡咯烷酮及水。 水性配方可由水添加至乳液縮物,糊劑,油分敗液或可 濕性粉末(嘖灑散劑,油分敗液)中製得。製備乳液,糊劑 與油分散液時*可利用濕潤蜊或粘附劑,分敗蜊或乳化蜊 使成份本身或溶於一種油或溶劑中之成份與水均質化。然 而,適於經水稀釋之濃縮物亦可包括活性成份,瀰澗W, 粘附蜊,乳化劑或分散劑旦可能使用溶劑或油製得。 合宜界面活性物質為鐮金羼,1«(土金羼及木質磺酸、酚 磺酸、萘磺醸及二丁萘磺酸之銨鹽》及烷芳基磺酸酯,烷 基硫酸酷,烷基磺酸醏、腊肪族酵的硫醗酯及脂肪酸和其 鐮金鼷和鐮土金饜鹽類,硫酸化脂肪族酵乙二酵褽之_、 磺化萘之縮合產物,及用由醛處理後之萘衍生物,用酚及 甲醛處理之萘及萘磺酸的縮合產物,聚氧乙烯辛基酚醚* 乙氧化之異辛基酚,辛基酚及ΐ酚►烷酚聚乙二酵酷,三 -158- 本紙張尺度適用中國國家搮準(CNS ) A4规格(210X 297公釐)
經濟部中央標準局貝工消费合作杜印製 A 7 ____B7 五、發明説明(156) 丁苯基聚乙二酵脂,烷芳基聚_酵,異三癸基酵脂肪族酵 環氧乙烷縮合物,乙氧綦性篦麻油,聚氧乙烯烷賭,乙氧 基性聚氧丙烯,月桂酵聚乙二酵酯縮醛,山梨酵醋,木質 亞硫酸濃液及甲基纖維素。 用固賭載劑琨合物或研磨活性物筲可製備粉劑,臞劑及 擴散性姐合物。 一般組合物含0.01至95 (較佳為0.1至90)重鼉百分比 之活性化合物。用於本文活性化合物之純度依NMR光譜為 9 0至1 0 0 S!較佳為9 5至1 0 0 »:。
密化 重此物 加烷1分 緊性 0〇 依合 由烷二至百 由 土活 和 化 物乙十加簠 物 嶺之 膠合性 合氧份烷重 合 高比 矽混活 混瑁量乙 9 混 細分 末密ί 該耳重氧佔 該 微百 粉繁蜊 *荑2 環物 , 份量 份物製 中10, 耳合 中 董重 量合之 物至物莫化 物 重 5 重混物 合 8 產40性 合 95有92之合 混之之之活 混 與含 與油化 於份胺份ί 於 物劑 物纗性 溶量醯量成 溶 合應 合石附 物重醇重構 物 :化到 化面粘。合 6 乙 2 所 合 例明得 明表好}化,單與物 化 實發式 發膠良比明笨Ν-驩產 明 之本方 本矽有分發甲酸鈣之 發 物之此 之在具百本二油之油 本 合份依 份»到釐份份耳酸麻 份 姐董。。最哦得重量量莫磺MCM 為重合物重份式23重重1 苯耳}重 下5 混合30量方佔1090至基莫比20 W . . . I Ε I W 本紙張疋度適用中國國家梯準(CNS ) Α4规格(2丨OXM7公釐) B7 五、發明説明(157) 6 0重量環己醑,3 0重量份異丁醇,5重量份之7奠耳 環氧乙烷加至1莫耳異丁基酚之產物及5璽量份之 40莫耳環氧乙烷加至1莫耳Μ麻油之產物所構成(活 性化合物佔1 6重董百分比)。 V . 8 0重量份本發明化合物與3重量份二異丁基萘-« -磺 酸之納鹽* 10重量份來自亞硫酸願液之木質素磺酸之 納鹽與7重量份粉末矽膠充份混合且在綞磨中研磨混 合物(活性化合物佔8 0重量百分比)。 VI . 90重量份本發明化合物與1 0重量份Ν -甲基-cx -吡咯啶 酮之溶液且所得之溶液通用於非常细滴之型式施用( 活性化合物佔9 0重量百分比)。 W. 20重量份本發明化合物溶混合物中,該混合物由40重 量份環己酮> 30重量份異丁酵* 20重董份之7奠耳環 氧乙垸加至1萁耳異丁基酚之產物及10簠量份之40黄 耳環氧乙烷加至1莫耳Μ麻油之產物所嫌成。倒出溶 液使其微散成1 0 〇,〇 〇 〇水重量份,所得水份散劑含 0 . 0 2重量百分比活性化合物。 ▽HI . 20重量份本發明化合物與3重量份二異丁基萘-α -磺 經濟部中央標隼局貞工消費合作社印裝 酸之納鹽,17重量份來自亞硫酸醆液之木質素磺酸之 納鹽及6 0重量份粉末狀矽膠充份混合並在麵磨中研磨 中研磨混合物。賴微敝混合物,成20 , 000水重量份, 得到0 . 1重量百分比活性化合物之嗔霧液》 可把活性成份结合至固體載劑中製備顆粒•如,包覆》 浸漬或同質性顆粒,固體載爾之實例為磺土如矽酸,矽膠 -1 6 0 - 本紙張尺度適用中國國家梯準(CNS ) Α4规格(2丨0Χ297公釐) A7 __B7 五、發明説明(158 ) ,矽酸鹽(酯)> 滑石*白陶土,活性白土,石灰石•石灰 ,白堊*粘泥,黃土,粘土 •白堊石,矽藻土 •硫酸鈣, 硫酸鎂,氧化鎂* 土中塑料*肥料如疏酸胺,瞵酸銨,硝 酸銨及尿素,及蔬菜產物如毅粉,樹皮粉*木粉及堅果毅 粉,織維狀粉末及其它固體載劑。 若合宜甚至在立刻使用前(槽混合物)將不同類型之油 類,殺草劑,殺真菌劑,其它農藥及殺菌劑加至活性化合 物。這些藥劑可依照本發明重量比率1 : 1 0至]0 : 1混合劑姐 合物中。 合成實例 下列合成實例之程序係用起始化合物合宜修飾而得到進 一步之化合物I 。所得之化合物見於具有物理數據的下列 表中。 實例1 (E,E)-2-甲氧亞胺基甲基,1''-乙醢基)亞 胺氧甲基]苯乙酸甲醋 經濟部中央標準局員工消費合作社印装 在保護的氣體且具有稍為冷凍的室溫中將21克(0.21莫 耳)二乙豳基單胯加至6 · 4克(0 . 2 1奠耳)氬化納(8 0 % ) 於150毫升無水之二甲基甲醢胺且在室溫下播拌混合物 30分。然後滴加60克(0.2]荑耳)2 -甲氧亞胺基- 2- (2 溴甲基)苯乙酸甲酸於3 6 0奄升二甲基甲醣胺的溶液並在 室溫中攫拌16小時。加人10¾強度之邇酸後,用甲基第三 丁醚萃取。用水冲洗經結合之有機相> Μ N a 2S 0 4乾燦並濃 縮。將殘餘物懸浮於稍冷之甲酵中。經由抽吸濾除後,得 -16 1- 本紙張尺度適用中國國家標準(CNS ) A4規格(2丨Ο X 297公釐) 經濟部中央標準局員工消費合作社印製 A7 B7 五、發明説明(159 ) 到38克(59¾)如淡棕色晶體且熔點為69-71 t:之檷題化合 物。 "H-NMR (CDC13):5=1.87(s, 3H); 2.30(s, 3H); 3.85 (s, 3H); 4.05(s, 3H); 5.15(s, 2H); 7. 1 7 - 7 . 48 ( m, 4 H ) p p m ° 實例2 (E,E,E)-2 -甲氧亞胺基- 2- [2'-(l''-甲基,1'·-(1"· -乙 氧亞胺乙基))亞胺氧甲基]苯乙酸甲醗之製備 將0.96克(9.8毫奠耳)之0 -乙羥基胺鹽酸鹽及0.6克 無水的分子篩珠(3A)加至2.5克(8.2毫莫耳)(Ε,Ε)-2 -甲氧亞胺基-2- [2’- (:Τ’-甲基,1’’-乙醢碁)亞胺氧甲 基]苯乙酸甲酯於6 0奄升溫熱的甲醇溶液·經冷卻至室溫 後,該混合物靜止至室溫5天。濾除分子篩後,濺縮溶液 ,將殘餘物分配於甲基第三丁醚及水間,且用水冲洗有機 相,M Na2S〇4乾煉並濃縮。用正-己烷研制殘餘物後用抽 吸來濾除,得到1.8克(63¾)如白黃色晶髑且熔點為 6 9 - 7 2 T: 之標題化合物。 ^-NMR (CDCl3):<5=1.27(t, 3H) ; 1 . 96 (s , 3H) ; 1.99 (s, 3H); 3.84(s, 3H); 4.04(s, 3H); 4.1?(q, 2H), 5.06(s, 2H); 7.17-7.49U, 4H)ppm 實例3 (E , E , E) - 2 -甲氧亞胺基-2 - [ 2 ' - (1 ’ ·-甲基,1 ' ' - U ’ ’ ’ -羥 亞胺乙基))亞胺氧甲基]苯乙酸甲賄之製備 將2.0克(17奄莫耳)之二乙醢基二肟分加至0.6克( -162- 本紙張尺度適用中國國家標準(CNS ) Α4規格(210X 297公釐) 一 裝-- (請先閱讀背面之注意事項本頁)
、1T 」 ___ B7 五、發明説明(16〇) 20奄舆耳)氫化納(80¾)於14奄升無水的二甲基甲醯胺中 竝在室溫時播拌混合物30分。然後加人5 . 0萣(i 7¾莫耳 )2 -甲氧亞胺基- 2- (2渙甲基)苯乙酸甲醋於30毫升二甲 基甲醸胺的溶液並在室溫時攪拌混合物2小時。加入1 0 % 強度之鹽酸後*用甲基第三-丁醚萃取*用水冲洗經結合 的有機相,K N a 2 S 0 4乾燦並且滬縮。用甲酵研制殘餘物後 >抽吸《除固體迴旋蒸發氣漉縮後在矽膠上(甲基第三-丁醚/正-己烷)K柱狀色析純化濾液。得到1 . 0克 (1 8 )如白色粉末且熔點為1 0 7 - 1 1 1 t〕之檷題化合物。 iH-NMR ( C D C 1 a) : δ = 1 .97 (s , 3H); 2 . 00 (s, 3H); 3,84 (s, 3H); 4.05(s. 3H); 5.08(s, 2H); 7. 1 7 - 7.45 ( ra, 4H); 8.56(s, lHippra0 實例4 4 -羥亞胺基-2 , 2 -二甲基戊-3-嗣之製備 經濟部中央梯準局員工消费合作社印製 在室溫時將40克氯化氫於156克乙_的溶液加至96克( 0.84莫耳)2,2-二甲基-3-戊酮於960克之甲苯中。冷卻至 -1 0 υ 後 > 滴加9 5克正-丁基亞硝酸鹽於4 7 0克乙醚的溶 液《在-1 0 t:至0 播拌混合物4小時讓其變成室溫。總 共經過1 6小時後*每次用1升冰水冲洗酒合物三次。然後 每次用1 Μ氫氧化納的溶液萃取二次。分出驗性相用2 0 X強 度之硫酸中和。抽取濾除粗製產物,乾燥後由正-己烷再 结晶。得到6 6克(5 5 % )如白黃色粉末且熔點為1 0 7 - 1 1 (ΓΌ 之檷題化合物。 '1 Η - N M R ( C D C i a ) : a =1.29(s, 9 H) ; 1 . 9 9 (s. 3 H ) ; 8.30 -1 6 3 - 本紙張尺度適用中國國家標準(CNS ) A4規格(210X297公釐) 五、發明説明Ο61 ) (s , 1 H ) p p m 實例5 (E)-2-甲氣亞胺基- 2- [2'-(l,f-甲基, 二甲乙羰基))亞胺氧甲基]苯乙酸甲酯之製備 在保護的氣體下將25克(0.1 7莫耳)4-羥亞胺基-2,2- * 二甲基戊-3 -嗣分批加入6 . 4克(0 . 2 1箅耳)氫化納(8 Ο ίΚ) 於150奄升的無水二甲基甲醢胺,將反應混合物溫熱至 5 0 t:。持鑛攫拌3 0分,滴加5 0克(0 . 1 7奠耳)2 -甲氧亞胺 基-2 - ( 2 ’ -溴甲基)苯乙酸甲酯於3 0 0奄升二甲基甲醢胺的 溶液並在室溫下播拌混合物1 6小時。加人1 Ο »ί強度之鼸酸 後,用甲基第三-丁醚萃取。用水冲洗經結合的有機相, KNa2S〇4乾燦並灕縮。在矽膠上(甲基第三-丁醚/正-己烷)上以柱狀色析法純化黑色油狀的殘餘物然後將所得 之粗製產物懸浮於冰冷的甲酵中。抽吸»除後得到24克 (4U)幾乎無色的粉末且熔點為58-60 t:之檷題化合物。 ^-NMRfCDCU): «3 =1.19(s, 9H); 1.90(s, 3H); 3.83 (s, 3H); 4.04(s, 3H); 5.11(s, 2H); 7.18-7.45(m, 4 H ) p p m 〇 實例6 經濟部中*梂準局貝工消费合作社印製 (E)-2-甲氧亞胺基-2-[2,-(l·’-甲基, 64.....-氣苯基)己氣亞胺基,(2·'·,2’’’-二甲 丙基))亞胺氧甲基]苯乙酸甲賄之製備 將5.9克(26奄興耳)0-6-(4,-氮苯基)己羥基胺> 3.6克無水的分子篩珠(3久)及1.6克(8.6毫奠耳)對- -164- —本紙張尺度itifl巾DH轉率(CNS丨A4规格(2丨GX297公釐y 經濟部中央梂準局貝工消费合作社印製 Α7 ___ Β7__ 五、發明説明(162) 甲苯磺酸水合物加至3.0克(8.6¾莫耳)(Ε)-2 -甲氧亞胺 基 _2-[2,-(1,,-甲基,1,,-(1,,,,1,,’-二甲乙羰基>)甲 肢氧甲基]苯乙酸甲酯於60毫升溫熱甲酵溶液’經冷卻至 室溫後迴流混合物3小時。烴由把分子篩»除後*濃縮溶 液,將殘餘物分配於甲基第三-丁醚與水間’用水沖洗有 機相,以Na2S〇4乾煉並漉縮。在矽膠上(己烷/甲基第三 -丁醚)柱狀色析後,得到3.8克(79¾)如白黃色油®的 檷題化合物。 UMR (CDCU): δ =1.09(s, 9H); 1.26-1.42U,4H); 1.52-1.67(m,4H); 1.90(s, 3H); 2.57( t,2H); 3.84(s, 3H); 3.99(t, 2H); 4.03(s, 3H); 5.02(s, 2H) ; 7 · 07 -7 . 47 U, 8H) ppm ° 實例7 (E)-2-甲氣亞胺基-2-[2’-(l,’-甲基》丨’,-甲氣嫌基)亞 胺氧甲基]苯乙酸甲酸之製備 將6.1克(52毫萁耳)2 -羥亞胺基丙酸甲酿分批加人 2.0克(67¾莫耳)氫化納(80¾)於1〇〇毫升無水二甲基 甲醢胺,反應混合物熱至50t!。捋緬攢拌30分’然後滴加 15克(52亳莫耳)2 -甲氣亞胺基- 2- (2,-澳甲基)笨乙酸甲 酯於9 0奄升二甲基甲醢胺之溶液,並在室溫攢拌混合物 1 6小時。加入1 0強度鹽酸後,用甲基第三-丁醚萃取。 用水冲洗經結合有機相,以Na2S〇4乾嫌並濃縮°殘餘物懸 浮於冰冷甲酵。油吸«除後得到7 · 2克(4 3丨)如灰_色粉 末且熔點為78-82 t:之檷趙化合物。 -16 5- 本紙張尺度適用中國國家#準(CNS ) A4规格(210X297公釐) (請先閲讀背面之注意事項\1^寫本頁) 訂 •U. A7 B7 五、發明説明(165) lH-NMR (CDCla):<5 =2.04(s. 3H); 3.85(s. 3H); 3.86 (s,3H); 5.19(s, 2H); 7.16-7.49U,4H)ppid。 實例8 2-[2-(l’’-甲基,甲氧亞胺基,丨苯基)甲 基)亞胺氧甲基]苯基-3-甲氧基-丙- Ε- 2-烯酸甲醋
c == choch3 co2ch3 H3CON== C(C6H5) — C(CH3)= noch2 將2.4克(28¾奠耳)0-甲羥基胺鹽酸鹽與3克無水分 子篩(3 A )加至2 . 5克(7奄奠耳)2 - [ 2〜(1 ” -甲基, 1”-苄醢基)亞胺氧甲基]-苯基-3-甲氧丙- E- 2-烯酸甲賄 於100毫升甲酵的溶液。在室溫時讅反應溶液靜置3天接 著在6 0 t攪拌8小時。 濾除分子篩後,將溶液加至200毫升水並用甲基第三-丁醚萃取混合物。 經濟部中央標準局員工消费合作社印製 用水冲洗經結合有機相,KNa2S〇4乾燥並漉縮。在矽膠 上(正-己烷/甲基第三-丁醚9:1)行柱狀色析後 > 得 到1 . 1克(4 0 S:),形成為異構物之混合物(側鍵之異構化 作用*異構物1:10)之標趙化合物。無色油體。 I R [ c ία - 1 ](薄膜) 768, 1036. 1057. 1111, 1130, 1190, 1256. 1284, 1634, 1709, 2930 -1 66 - 本紙張尺度遑用中國國家橾準(CNS ) A4規格(210X297公釐) A7 B7__ 五、發明説明(164 ) 實例9 α _ [ 2 ’ - (1 , ’ -甲基,]’ · _ ( ! u _甲氧亞胺基,! ’ ’ ’ _苯基 )甲基]亞胺氧甲基]苯基H-甲基丙烯酸甲酯之製備
co2ch3 H3CON— C(C6H5) — C(CH3)= noch2 . c == CHCH3 將1克(11.4¾¾耳)〇-甲羥基胺鹽酸鼸及2克無水分 子篩(3A)加至1龟(2.9奄舆耳)α-[2’-(1”-甲基,1”-苄醸基)匪胺氧甲基j苯基- E- /3-甲基丙烯酸甲醋於50奄 升甲酵的·溶液,先讓溶液靜置在室溫2小時*然後在加熱 6小時。濾除分子篩後,加水並用甲基第三-丁醚萃取混 合物。用水冲洗經結合之有櫬萃取物,以Na2S〇4乾燦並瀟 縮。 經矽膠(正-己烷/甲基第三-丁醚9:1)柱狀色析後 ,得到0 . 9克(85¾)形式為異構物混合物(1 : 1,側鍵異構 化作用)之標題化合物。無色油體。 IUcnT1](薄膜):693, 764, 872, 892, 1 005, 1 035, 1207, 1253, 1435, 1716, 2920 經濟部中央梯隼局貝工消費合作社印51 實例10 (E)-2-甲氧亞胺基- 2- [2·-(1,’-甲基,1·*-(1’’·-(2)-甲 氧亞肢基> 1 · · ’ -苯基)甲* ) ( Ε )-亞胺氧甲基:]苯乙醸甲 酷·(表I ,化含物I 48)異構或(Ε)-2 -甲氧亞胺基-2-[ ,2,( 1 ' ’ -甲 * , 1 ’ Μ 1 ’ ’ ’ - (Ε)-甲氧亞胺基,]'’ ’-笨基)甲 — 16 7- 本紙張尺度適用中國國家橾準(CNS ) Α4規格(2ΗΤΧ 297公釐) 經濟部中央標隼局員工消費合作社印製 五、發明説明(165) 基](E )-亞胺氧甲基]苯乙酸甲賭: 將46克起始化合物懸浮於600奄升乙_>用200奄升經 飽和之醚H C I處理並在室溫時靜置1 9小時》將反應溶液加 至冰水中並用二氯甲烷萃取,M Na2S04乾燥萃取物.。經 迴旋蒸發器濃縮後,得到形式(35克$75%理論值)。 熔點:1 1 8 - 1 2 0 t: i: 9 5 % S , E , E ) -168- 本紙張尺度逋用中國國家揉準(CNS ) A4規格(210X297公釐) A7
B 五、發明説明(166) 經濟部中央標窣局貝工消費合作社印製
表 I 人 0~(r2)* R4 H3COC 人5? n 〆 OCH3 0 No. R2m R3 R4 RS 败逋 I.01 H ch3 CH3 , H 熔黏:107-111°C 1.02 H ch3 ch3 ch3 熔點:89-91°C 1,03 H ch3 ch3 C2H5 熔點:69-72°C 1.04 H ch3 ch3 異-c3h7 熔點:128-130°C 1.05 H ch3 ch3 正-c«h9 熔酤:59-62°C 1.06 H ch3 ch3 第三 油;1H-NHR(CDC13):6· 1.29(s,9H); 1.92(s,3H>;. 2.00(sr3H); 3,85(s#3H); 4.04(s,3H); 5.06(s,2H); 7.17-7.48(m,4H) ppm 1.07 H ch3 ch3 正 熔黏:49-53°C 1.08 H ch3 ch3 ch2cn 熔點·· 80-86°C 1.09 H ch3 ch3 ch2ch2cn 熔點:52-61°C 1.10 H ch3 ch3 3-甲基-丁. -2-烯-1-基_ 熔點:S1-S6°C 1.11 H ch3 ch3 4-Cl-C6H4-CH2 熔黏:128-130°C 1.12 H ch3 ch3 2-萘 基-CH2 搭點:83-85〇C 1.13 H ch3 ch3 6-(4'-氣苯基) 己-1-基7 油;1H-NMR(CDC13):δ* 1.26-1.70(m,8H); 1.94(s,3H); 1.98(s,3H); 2.56(t,2H); 3.84(s,3H); 4.03(s,3H); 4.10(t,2H); 5.06(s,2H); 7·08-7·50(m,8H) ppm 1,14 H ch3 ch3 2,4-(N〇2)2-C«H3 熔點:158-161〇C 1.15 H ch3 ch3 3-CF3-C6H4 熔點:77-79°C 1-16 H ch3 ch3 4-CF3, 6-01-%¾ -2-¾ 熔點:134-137°C 1.17 H ch3 ch3 4-CF3-吡啶 -2-« 熔黏 1 92-95°C 1-18 H ch3 ch3 6-C1-,哺啶 -4-« 110»120°C 1.19 H ch3 CHj (E)-l-氯丙烯 -3-¾ 熔貼:76-7B«iC 1.20 H CHj ch3 (E)-4-(4 *- 舐苯基)-1*-2- 馆貼:69-73〇C (請先閲讀背面之注意事項再填寫本頁) -169- 本紙張尺度適用中國國家樣準(CNS ) A4规格(210X 297公釐) 第84100978¾專利 中文銳明膂修正頁 __________——- ^•告4 【85年7月) R7 ψ γ^ψ:η _Μ3_ 五、發明説明(167) 經濟部中央標準局負工消費合作社印製
No* R2« R3 R4 R5 败!^ 1.21 Η ch3 ch3 丙炔-3-S 熔點:119-121°C 1.22 Η ch3 ch3 2-控内~1 iSi£ : 74-79〇C 1.23 Η ch3 ch3 6-羥-2-甲基-啼淀甲3 189-194°c 1.24 Η ch3 ch3 羥-2-異丙基-嘧啶-4-基甲基 溶贴:180-187°C 1.25 Η ch3 ch3 . 6-羥-2-環丙基-· 噃啶-4-基甲基 190-193°c 1.26 Η ch3 ch3 5-(2'-呋喃)-戊 -1-基 熔點:36-40〇C 1.27* Η ch3 ch3 5-(2·-Ν-甲基吡咯 )-戊-1 -基 yi 熔點·: 40-44°C 1.28 Η ch3 ch3 2-(4,-(氛苯基) ™吗嗤-4_基甲基 熔黏:110-115°C 1.29 Η ch3 ch3 3-三氟甲基吡啶 -2-基 熔點:112-115°C 1-30 Η ch3 ch3 三氰甲基吡啶 -2-基 熔黏:110-115°C 1.31 Η ch3 ch3 6-(2'-疏苯)-己-1-基 IR [cm-l]: 893, 958, 988, 1021, 1049, 1070, 1219, 1365, 1729, 2935 1-32 Η ch3 I 5三-C4H0 Η 熔點:114-117〇C 1.33 Η CH3 第三-CnHo ch3 运貼:51-S5〇C 1.34 Η ch3 第三 -CaHo c2h5 油;IR (薄膜):2972, 2955, 1729, 1364, 1219, 1069, 1044, 1020, 957 1.35 Η ch3 H - ‘cx 異-c3h7 油;IR (薄瞑):2972, 2937, 1729, 1366, 1323, 1218, 1070, 1047, 1020, 962 1.36 Η ch3 項三 C.tH〇 正-c<h9 油;IR (薄蜈 >:2957, 2935, 2Θ72# 1929, 1437, 1364, 1218, 1069, 1020, 959 1.37 Η ch3 湞三 -Ullo 第三-αιι〇 油;IR (薄2973, 1730, 1364,.1210, 1195r 1069, 1047, 1020, 956, 916 --------^ I 裝------- 訂 ------{•線 » / (诗先閲讀背面之注意事項再填寫本頁) 170 本紙伕尺度適用中國國家標窣(CNS ) A4規格(210 X 297公釐) 第&4100978號專利申請m 中文銳明軎修正頁(85年7 ^ ^7 ^ , i :,· ·.: 1 補充j 五、發明説明(168 ) 經濟部中央標準局員工消費合作社印製
No· R2» R3 R5 数據 Ι·38 Η ch3 第三 -C4He 正 油;IR (薄瞑):2955, 2933, 2870, 1729, 1364, 1218, 1069, 1049, 1020, 958 1.39 Η ch3 第三 "C4He (E)-l-氛丙烯 -3-基 油.;IR < 薄膜.}: 295S, 1729, 1437, 136S, 1219, 1069, 1046, 1020, 959, 915 1.40 Η ch3 第三 -c4h〇 丙炔-3-基 < 油,· IR (薄膜):3300, 2955, 1729, 1437, 1365, 1321, 1219, 1069, 1020, 1006, 916_ 1-41 Η CH3 第三 "C-iHi) 3-甲基-丁 -2-烯-1-基 .油,;IR (薄胰):2968, 2954, 1729, 1437, 1218, 1069, 1046, 1019, 985, 918 1-42 Η ch3 第三 2-萘基.-CH2 油.;IR (海膜):2954, 1728, 1437, 1365, 1219, 1069, 1019, 958, 921, S96 1*43 Η ch3 «a: —^ 第二 -c4h〇 4-C1-CsH4-CH2 ,油IR (薄膜):2960, 1728, 1491, 1365, 1218, 1089, 1069, 1015, 980, 919, 881 1.44 Η ch3 XV* ~^4Ηβ (E)-4-(4,-氛苯基 > 丁-2-烯-1-基 油;IR (薄膜}: 2963, 1728, 1491, 1365, 1218, 1093, 1069, 1048, 1016, 983, 960 1.45 Η ch3 第三 "CaHo 6-(4'-·氛苯基 )己-1-基 油;IR (薄膜):2934, 1729, 1492, 1364, 1218, 1092, 1069, 1048, 1016, 958 1.46 Η ch3 第三 -CaH〇 3-CF3-CsH4 油;IR (薄P): 2980, 1729, 1450, 1331, 1214, 1169, 1127, 1069, 1020# 941, 92Θ 1.47 Η ch3 C6H5· Η 熔點:139-143°C 1.48 Η CHj c«h5 ch3 熔點:71-75°C 1.49 Η ch3 c4h5 C2H5 熔點:65-70°C Ι..50 Η ch3 CtHs S-c3h7 一 熔貼:83-87°C 1.51 Η ch3 C4H5 rE-C^H, (油;IR < 薄腴):2956, 2937, 1728, 1219, 1201, 1069, 1046, 1019, 978, 959 1.52 Η "* H— ch3 csh5 4-Cl-CiH4-CH2 馆贴:88-93°C 17 1- . ~1 —^M— (請先閏讀背面之注意畜‘項再填寫本頁) 訂
.X - 免適用中國囡家標準(〇<5)八4規格(210'乂 297公釐) 經濟部中央標準局貝工消費合作社印製 306 細 a7 B7 五、發明説明(169)
No. R2« R3 R4 R5 敝據 1.53 Η ch3 CSHS 3-CF3-CeH4 油;IR《薄鼸):2940, 1729, 1450, 1329, 1281, 1219r 1169, 1126, 1069, 1021, 957 1.54 Η ch3 c«h5 6-(4〜氯苯基) 己-卜基 油;IR (薄縝):2935, 1732, 1492, 1444, 1437, 1219, 1069, 1015, 985, 959 1.55 Η ch3 C6H5 (E)-4-(4,-鈑笨 基)丁-2-烯-1-基 ,油·; IR (:薄臢.}: 2945, 1727, 1491, 1444, 1437, 1219, 1201, 1069, 1047, 1015, 974 1.56 Η c«h5 c6h5 ch3 IR [cm·*1] (KSr)i 692, 766, 958, 986, 1018, 1051, 1069, 1221, 1445, 1727, 2940 1.57 Η c«h5 c$h5 c2h5 油;IR [cirri](薄臢,): 693, 766, 959, 985r 1019, 1050, 1069, 1221, 1445, 1728, 2940 1.58 Η c6h5 c6h5 正·<:3η7 油;IR [cnr1](薄瞬); 693, 766, 962, 987r 1020, 1068, 1221, 1445, 1728, 2930 1.59 Η c6h5 C«H5 異-C3H7 油;IR [cirri](薄膜): 693, 766, 978, 1019, 1069, 1121, 1220, 1323, 1445, 1728, 2960 1.60 Η c6h5 C6H5 1E-C4H9 油; IR [cnH](薄膜): 693, 960, 975, 1020, 1069, 1220, 1445, 1728, 2956 1.61 Η c«h5 * c6h5 第三-C4He 油;IR [cm-ι] {薄膜.): 694, 961# 971, 1019, 1069, 1190, 1220, 1364, 1445, 1728, 2960 1.62 Η c6h5 c4h5 正,C‘Hi3 油;IR [cirri](薄臟 >: 693, 959f 986, 1019# 1069, 1220, 1445r 1728, 2935, 2952 1.63 Η C‘HS CiHs 3-甲基-丁. -2-婦-1 -基 油.;IR【cnrM (薄顧” 693, 766, 958, 9Θ6, 1019, 1069, 1220, 1444, 1728, 2930 1.64 Η ch3 ch3 4_苯*-丁-丨-綦 熔黏《 64-66〇C 1.65 Η CHj CHj 4-苯氣丁-1-基 油;IR【crtr1】(薄Bl): 755, Θ90, 987, 1020, 1049, 1070, 1220# 1245, 1498, 1728, 2940 (請先閲讀背面之注意事項再填寫本頁) Φ1Ι -172- 本紙張尺度適用中國國家標準(CNS ) A4规格(210X 297公釐) A7 B7 發明説明(17Q) 經濟部中央樣準局員工消費合作社印裝
No. R2m R3 R4 R5 敝逋 1.66 Η ch3 CH3 2-W-氣苯铒基) -乙-〗-基 油;IR【cm-ι】(薄親): 749, 1020, 1036, 1051, 1070, 1205 1219, 1260, 1507, 1728, 2940 1.67 Η ch3 ch3 3-(2'-頬苯氧基) 丙-卜基 *· 53-56°C 1.68 Η ch3 ch3 4-<2’-顛苯氧基) .丁-卜基 熔點:4 7-5 0°C 1.69 Η ch3 ch3 6-(4f-氯苯氧基) -己-1-基 油.;IR [cm-1](薄膦.〉: 890, 1020, 1047, 1070, 1219, 1244, 1366, 1492r 1728, 2939 1.70 Η ch3 ch3 2-(4'-氛苯氧基) '丙-1 -基 油;IR [cnri](薄臢.): 886, 958, 1020, 1049, 1070, 1220, 1241, 1366, 1490, 1728, 2920 1.71 Η ch3 ch3 c6hs-c2h4-o-c2h4 油;IR [cm·1](薄膜): B93, 958, 984, 1020, 1049, 1069f 1120, 1219, 1366, 1728, 2940 1.72 Η ch3 ch3 E-4-(3,-甲氧苯基 )-丁-3-烯-1-基 < 油;IR [cnri](薄瞋 890, 959, 1020, 1046, 1070, 1219, 1266, 1366, 1436, 1728, 2940 1.73 Η ch3 ch3 4-(V-氟苯基)- 丁-3-烯-1-基 熔點:60-64°C 1.74 Η ch3 ch3 co2ch3 P?N's-〇CH3 — ch2— 熔黏·: 160-164°C 1-75 Η ch3 ch3 (3-渙異聘唑 -5-S)甲基 油j IR [cm-i】(薄鼷): 879, 898, 952, 1020, 1070, 1202, 1219, 1366, 1437, 1728, 2940 1.76 Η ch3 ch3 (3-CF3- 馎啤吨-5-*) 甲稱 油」IR [cnr1】(KBr): 941# 1013, 1055, 1070, 1149, 1187, 1199, 1226, 1726 1.77 Η ch3 ch3 (3-课-丙與吗啤 二5-ft)甲« 油;IR【cm-〗】(薄瞬” 828, 898, 958, 983f 1021, 1070, 1219, 1367, 1437, 1728, 2960 (請先閱讀背面之注意事項再填寫本頁) 裝---
,1T -173- 本紙張尺度適汛中國國家標準(CNS ) A4規格(2丨0X29?公廋) A7 B7 五、發明説明(171) 經濟部中央橾準局貝工消費合作社印製
No. R2· R3 R4 R5 敝逋 1.78 Η ch3 ch3 (3-瓖丙钨嗶唑 -5-基)甲基 熔貼:72-7S°C 1.79 Η ch3 ch3 (3-i-肉 δ 油;iH-NMR(CDCl3): -1,2.4-呵二唑-5- δ - 1.34(s,3H); 填)-甲《 1.36(S,3H); 1.92(S,3H); 2.04(S,3H); 3.13(inflH); 3.84{s,3H); 4.04(s,3H); 5.06(s,2H); 5.31(s,2H); 7.15-7.45(m,4H) 1.80 Η ch3 ch3 (2-甲基嗶唑 油;IR [cm-l](薄齡): -4-基)-甲基 885, 894, 958, 986, 1020, 1070, 1219, 1366, 1437, 1728f 2920 1.81 Η ch3 p—OCHi— c6H4 CH3 熔點:105-110°C Ι·82 Η ch3 P-OCH3- CeH4 C2Hs 溶點:64-70°C 1.83 Η ch3 p—OCH3— c6h4 £-c3h7 熔黏:58-65〇C 1.84 Η ch3 P-0CH3- c€h4 異-c3h7 熔點:60-S8〇C 1.85 Η ch3 P-0CH3- c6h4 ZE-c4h9 熔黏:95-100°C 1.86 Η ch3 P-OCH3- c«H4 第三-C4He 熔點:76-80°C 1.87 Η ch3 C6Hs _3-氣-苄基 一 油;IR [cnrl】(薄縝): 695, 779, 959, 1019; 1069, 1220, 1255, 1446, 1591, 1728, 2920 1.88 Η ch3 CeH5 3-溴-苄基 油.;IR [cm-l](薄隳)·· 695, 777, Θ90# 959, 1019, 1069, 1219, 1436, 1444, 1728, 2930 1.89 Η ch3 c‘h5 3-CF3-^« 油;IR【cnr1】(薄親 702, 1020, 1072, 1125, 1166, 1201, 1220, 1330, 1445, 1729, 2930 1.90 Η ch3 C4H5 4-M-苄基 油.;IR【cnri】(薄瞬 02€, 925, 958, 1020, 1069, 1202, 1221, 1484, 1728 1.91 Η ch3 c‘H5 3,4-二鉍苷《 IR 【cnri】 (KBr): 767, 879, 959, 1020, 1069, 1219/1437, 1444, 1471, 1728, 2930 -174- (請先閲讀背面之注意事項$寫本頁) 訂 本紙張尺度適用中國國家揉準(CNS ) Λ4規格(210 X297公釐) A7 B7 五、發明説明(口2) 經濟部中央橾準局員工消費合作社印裝
No. R2» R3 R4 RS 败據 1.92 H CHj C6H5 [fj] ——CH2— 。令W0、 0 熔贴:140-147OC 1.93 H ch3 ch3 -ch2co2ch3 熔貼·· 7〇-73〇c 1.94 H ch3 ch3 2-甲氧乙-1-基 熔酤·· 62-65〇C 1,95 H ch3 4-C1- c6h4 ch3 熔點:104-107〇C 1.96 H ch3 4-C1— c6h4 c2hs 熔點:74-76°C Ι·97 H ch3 4-C1- c6h4 IE-C3H7 油;IR (薄齡)·· 989, 1020, 1069, 1091, 1219, 1491, 1728, 2938 1.98 H ch3 4-C1- c6h4 異-C3H7 油;IR (薄膜: 974, 1019, 1069, 1091, 1120, 1219, 1324, 1490, 1728, 2960 1.99 H ch3 4-C1- c6h4 ΐΕ»〇4Η9 油;IR (薄膜.): 959, 979, 1020, 1070, 1091, 1219, 1728, 2937, 2957 1.100 H ch3 4-Cl- c6h4 第三-c4h〇 IR (KBr): 833, 894, 981, 993, 1021, 1067, 1218, 1364, 1722, 2970 1.101 H ch3 4-C1- c6h4 正-c6h13 油;IR《薄膜… 958# 1020, 1070, 1091, 1219, 1491, 1729, 2935, 2953 1.102 H ch3 4 - Cl- c«h4 3-甲基丁-2-m-i-m 油;IR (薄膜 960, 1019, 1069, 1219, 1437, 1491, 1728, 2930 1-103 H ch3 4-Cl- CfeH4 炔丙基 油;IR (薄賴·>: 958, 1009, 1069, 1092, 1220, 1437, 1491, 1728, 2120, 2930, 3280 1.104 H ch3 4 •F— c6h4 ch3 m.p.j 104-107°C 1.105 H ch3 4-F- c«h4 c2hs 油;IR《薄_)ι 841, 9S7, 1020, 1069, 1222, 1438「1509, 1728, 2930 -1 7 5 - (請先閱讀背面之注意事¾¾寫本頁)
打 ___i A----- 本紙張尺度逋用中國國家標準(CNS ) A4規格(2丨Ο X 297公釐)
7 7 A B 五、發明説明(173 ) 經濟部中央標準局貝工消费合作社印裝
No· R2m R3 R5 敝據. 1.106 H ch3 4—P— C6H4 正-〇3日7 油;(薄脚): 959, 989, 1020, 1069, 1222, 1437, 1S09, 1728, 2930 Ι·107 H ch3 4 —F— CeH4 異 -C3H7 m.p.: 66-71〇C 1.108 H ch3 4-F- c6h4 第三-c4h〇 熔點:76-81〇C 1.109 H ch3 4-F- c6h4 E-C4H9 油IR (薄膜): 959, 980, 1020, 1070, 1222, 1509, 1729, 2938, 2957 1.110 H ch3 4-F- c6h4 EE-c6h13 油;(薄膜): 958, 986, 1020, 1070, 1222, 1509, 1729, 2935, 2953 I.Ill H ch3 4-F- C6H4 3-甲丁基- 油·; IR (薄_): 841, 960, 986, 1019, 1069, 1222, 1508, 1728, 2930 1.112 H ch3 4--p— C6H4 炔丙基 熔黏:83-88°C 1-113 H ch3 4-C2- C6H4 Η : 137-140°C 1.114 H ch3 4-C1- c6h4 (2-甲基噻唑 -4-*)甲基 熔點:128-133〇C 1.115 H ch3 4—Cl— c6h4 (噻唑-4-基)甲基 熔點:93-97°C 1.116 H ch3 4-C1- c6h4 (3-異-丙基 -I,2,4-噚二唑-5-基)-甲基 ’油·; IR (薄膜): 874, 958, 1018, 1069, 1091, 1220, 1491, 1589, 1728, 2960 1.117 H ch3 4-C1- C6H4 (3-異-丙基異噚唑 -5-基)-甲基 /油.;IR (薄_): 959, 986, 999, 1021, 1070, 1092, 1220, 1437, 1491, 1728, 2960 1.118 H ch3 4-C1- c6h4 (3-溴-ip琴唑 -5-基)-甲基 1油;IR (薄膜” 952, 1014, 1069, 1092, 1201, 1219, 1334, 1362, 1436, 1727, 2930 1.119 H ch3 4-C1- c6H4 (3-CF3-辑噚唑 -5-堪)-甲基 :油;IR (溥賴): 970, 1016, 1070, 1092, 1155, 1192, 1219, 1491, 1728, 2930 1.120 H ch3 3—Cl— C‘H< ch3 熔點 * 78-81〇C 1.121 H ch3 C2HS ch3 熔點:88-910C -I 76- 本紙張尺度適用中國國家#準(CNS ) A4規格(2! Ο X 297公釐) 5 8ο 03 6 7 Β 五、發明説明(174) 經濟部中央標準局員工消費合作杜印製
No. R2« R3 R* R5 敝逋 1.122 Η ch3 C2H5 c2h5 熔點:60-65°C 1.123 Η ch3 4-CH3- c6H4 ch3 油·; IR (薄膜)·· 958, 1020, 1036, 1069, 1200, 1220, 1321, 1438, 1728, 2939 1.124 Η ch3 4-CH3- c6h4 c2h5 油IR (薄 922, 957, 983, 1020, 1069, 1220, 1438, 1729, 2940 1.125 Η ch3 4-CH3- ^ 13 正-C3H7 •油·; IR (薄膜): 959, 988, 1020, 1070, 1219, 1437, 1729, 2939, 2965 1.126 Η ch3 3-C1- c6h4 異-c3h7 _油;IR (:薄膜): 959, 980, 1020, 1070, 1120, 1201# 1219, 1324; 1729, 2940, 2980 1.127 Η ch3 3-C1- C6H4 正 油;IR (薄膜): 959, 980, 1020, 1070, 1201, 1219, 1729, 2938, 2956 1.128 Η ch3 3-C1- CfiH4 3-氮丙-2- «ClaEl 1 *fcrf· .輝-1-¾ 熔點:73-75°C 1.129 Η ch3 3-C1- c6h4 炔丙基 油;IR (薄膜)·· 928, 958, 1010, 1049, 1069, 1201, 1220, 1322, 1437, 1728, 2110, 2930, 3280 1,130 Η ch3 2-C1- C«H4 ch3 熔點:132-134°C 1.131 Η ch3 2-C1- c6h4 c2h5 熔點:104-108°C 1.132 Η ch3 2—Cl— c6h4 正-c3h7 熔酤:63-66〇C 1.133 Η ch3 3-CH3- isoxa- 20I- 5-yl ch3 油(薄膜): 2941, 1728, Ϊ438, 1220, 1201, 1070, 1039, 1019, 959, 897 1-134 Η ch3 3-CH3- isoxa- 20I- 5-yl C2H5 油.;IR (薄膜i): 2941, 1728, 1438, 1322, 1220, 1069, 1038, 1020, 988, 95Θ 1.135 Η ch3 3-CH3- isoxa- 20I- 5-yl iE-c3H7 油;IR《溥P): 2968, 2940, 1728, 1438, 1322, 1220/1070, 1047, 1019, 959 --I 7 7 - 本紙張尺度逋用中國國家樣孪(CNS ) Λ4规格(210Χ 297公釐) (請先閱讀背面之注意事項寫本頁) Β 五、發明説明(1乃) 經濟部中央標準局貝工消費合作杜印製 NO. R2m R3 R4 R5 数逋 1.136 Η ch3 3-CH3-與呵唑 -5-基 S-C3H7 油.;找(薄91): 2975, 2935, 1728, 1438, 1371, 1324, 1220, 1119, 1070, 1049, 1018, 960 1.137 Η ch3 3-CH3- 铒噚唑 m,5-S 5-yl 正 -C4H9 «油; IR {薄瞬>: 2957, 2939, 1728, 1438, 1322, 1220, 1070, 1020, 985, 958 1.138 Η ch3 3-CH3- 異曙唑 :5-基 正-c*h13 油;IR (薄膜): 2936, 1728, 1437, 1369, 1321, 1220, 1201, 1070, 1019, 958 1.139 Η ch3 3-CH3- 異噚唑· ~5** 基 丙基-1-烯-3-基 IR (薄鼴): 2940, 1727, 1438, 1220, 1201, 1069, 1048, 1019, 958r 914, 898 1-140 Η ch3 3-CH3- 異嗶唑 -5-基 (E)-l-氣丙 -1 -烯-3-基 油·,· IR (薄膜): 2940, 1728, 1438, 1220, 1201, 1070, 1048, 1018, 988# 957, 898 1.141 3-C1 ch3 ch3 ch3 熔黏:10S-107°C 1.142 3-C1 ch3 c«h5 ch3 熔點:120-123°C 1.143 3-C1 ch3 c6h5 c2h5 熔黏:113-115°C 1.144 Η sch3 ch3 ch3 油;IR (薄膜): 2930, 1737, 1432, 1302, 1221, 1063, 1048, 1012, 984, 952, 873 1.145 Η sch3 ch3 c2h5 油;IR (film): 2938, 1728, 1437r 1220, 1070, 1047, 1019, 987, 959, 883 1.146 Η sch3 ch3 正 -C3H7 油;IR (薄祺.): 2938, 1728, 1437, 1321, 1220, 1070, 1047, 1018, 989, 958 1.147 Η sch3 ch3 異 -C3H7 油;IR (薄瞬.μ 2956, 2938, 1728, 1436, 1220# 1070, 1040, 1018, 987, 959 1.148 Η sch3 ch3 正-c‘h13 油;IR (薄瞬): 2933# 1729, 1436, 1321, 1219, 1070, 1047, 1018, 989# 958 1-149 Η sch3 ch3 1 丙-1-烯-3-基 油;IR (薄脚Η 2930, 1728, 1436, 1320, 1219, 1200, 1069, 1046, 1017, 990# 958 -178- 本紙张尺度適用中國國家標準(CRS ) Α4現格(210Χ297公釐) (請先閲讀背面之注意事項 β5 .n τ - A7 B7 五、發明説明(176)
No. R2» R3 R5 敝據 1.150 Η sch3 CH3 3-CF3-C*H«-CH2- ,油.;IR (薄_): 2930, 1729, 1330, 1220, 1201, 1166, 1124, 1072, 1017, 987, 958 1.151 Η ch3 3 — 吡啶基 < ch3 油IR (薄膜): 2935, 1728, 1438, 1220, 1201, 1070, 1042, 1019, 958, 896, 875 1-152 Η ch3 3« 吡啶基, c2h5 <油;IR (薄膜): 2935, 1728, 1438, 1322, 1220, 1202, 1069, 1044, 1019, 982, 958 1.153 Η ch3 3» m啶基 正'3H7 油;:TR (薄膜.): 2966, 2939, 1728, 1437, 1220, 1070, 1045, 1020, 984, 958 1.154 Η ch3 3- 吡啶基· 舆-c3h7 *油;找(薄膜): 2965, 1728, 1371, 1324, 1220, 1121, 1070, 1048, 1021, 977, 960 1.155 Η ch3 3- 吡啶基- 正 油j IR (薄瞬): 2957, 2938, 1728, 1437, 1219, 1201, 1071, 1020, 979, 959 1.156 Η ch3 3 — 吡啶基 丙-1-婦-3'"基 油J (薄膜): 2940, 1728, 1322, 1220, 1202, 1070, 1020, 958 1.157 Η ch3 3- 吡啶基 (E)-l-氯丙-1-烯-3-基 油.;IR (薄膜): 2940, 1728, 1437, 1322, 1220, 1202, 1070, 1049, 1020, 985, 958 (請先閲讀背面之注意事項本頁) ¾ •本 訂 經濟部中央橾窣局貝工消費合作社印製 -1 7 9 - 本紙張尺度適用中國國家標丰(CNS ) A4规格(2!〇Χ 297公釐)
7 B 五、發明説明(1Ή) 經濟部中央樣準局貝工消费合作社印製 表II rsony4〆0 ~(R2)m R4 CH3°\^J^OCH3 , 0 No. R2n R3 R4 4 R5 败逋 II.1 H ch3 ch3 H 油;IR [cm-ι](:薄瞩·)·· 920, 985, 1111, 1132, 1257, 1286, 1365, 1437# 1633, 1709, 2930, 3370 II.2 H ch3 C6Hs ch3 ‘油L; IR [cm-1](薄膜): 768, 1037, 1057, 1111, 1130, 1190, 1256, 1284, 1634, 1709, 2930 II.3 H ch3 c$h5 c2hs 油;IR [cnr:](薄瞬.): 769, 1007, 1035, 1057 1111, 1129, 1256, 1284r 1634, 1709, 2930 II.4 H ch3 c6h5 正-c3h7 油;IR [cnr”(薄膜): 990, 1020, 1037, 1058, 1111, 1129, 12S6, 1284, 1634, 1710, 2930 II.5 H ch3 c6h5 興,c3h7 IR【cmd] (薄膜,): 769, 974, 1113, 1129, 1191, 1256, 1284, 1370, 1634, 1710, 2970 ΙΙ·6 H ch3 c6h5 3-幫苄基 油;IR [cnri】(薄膜): 769, 919, 1001, 1111, 1130, 1256, 1284, 1445, 1634, 1708, 2930 II.7 H ch3 c6Hs 正-c4H9 油;(薄p): 1030, 1111, 1130, 1256, 1284, 1634, 1710, 2956 II.8 H ch3 c«h5 第三-Cdfl 油;IR {簿犋): 768, 971, 1111, 1130, 1190, 1256, 1284, 1346, 1634, 1710, 2980 II.9 H ch3 C‘HS E-ctH13 油;(薄_)* 1003, 1030, 1058, 1111# 1129, 125S, 1283, 1634, 1710, 2933 II.10 H ch3 C‘Hs 3·甲《了 -2-烯-1-揭 油·; IR {薄膜·)| 768# 997, 1111, 1129, 1255, 1203, 1435, 1444. 1630, 1709, 2930 -180- (請先閲請背面之注意事項再填寫本頁)
-丁 I 本紙张尺度逋用中國國家標準(CNS ) A4规格(2!〇Χ297公釐) A7 B7 五、發明説明(178) 經濟部妒央標準局貝工消资合作社印裝
No· R2» R3 R4 R5 败據 11*11 Η ch3 CeH5 i丙基 ^ ; IR (薄隈 >: 769, 1006, 1029, 1058, 1U2, 1130, 1256, 1285, 1633, 1708, 2100, 2940, 3270 11-12 Η ch3 4-C1» CfiH4 ch3 熔貼:109-li3°C 11.13 Η ch3 4-C1- c6h4 c2h5 油;IR (薄膜): 1012, 1036, 1056, 1091, 1111, 1130, 1256, 1284, 1634, 1710, 2940 11.14 Η CH3 4*C1- csh4 正-c3h7 油·; IR (薄膜… 991, 1012, 1058, 1092, 1110, 1129, 1255, 1284, 1634, 1710, 2930, 2960 11.15 Η ch3 4-C1- C6H4 異-C3H7 ,油IR (薄鹛): 998, 1091, 1111, 1130, 1255, 1284, 1435, 1491, 1634, 1710, 2930 11.16 Η ch3 4-C1- CfeH4 正 -c4h9 '油;IR (薄膜>: 977, 1012, 1091, 1111, 1129, 1255, 1284, 1491, 1634, 1710, 2930, 2950 11.17 Η ch3 4-C1- c6h4 第三-C4He 油·; IR (薄膜): 972, 1111, 1130, 1189, 1256, 1284, 1365, 1490, 1635, 1711, 2940, 2970 11.18 Η ch3 4-Cl- C6H4 1£-c«h13 油;(薄膜): 1012, 1058, 1091, 1111, 1130, 1256, 1284, 163S, 1711, 2933 11.19 Η ch3 4—Cl — C6H4 炔丙基 (油;IR (薄醉〉: 1006, 1028, 1058, 1092, 1111, 1130, 1256, 1285, 1634, 1708, 2110, 2940, 3270 11.20 Η ch3 4-F- C6H4 ch3 熔點:113-118〇C 11.21 Η ch3 4-F- c6h4 C2H5 油;IR (:薄_): 1036, 1056, 1112, 1130, 1225, 1256, 1284, 1509, 1635, 1710, 2930, 2970 ΙΓ.22 Η ch3 4-F- c6h4 (£-C3H7 油《薄關 992, 1064, 1112, 1130, 1225, 1256,,1284, 1509, 1635, 1710, 2940, 2960 18 1
本紙張尺度適用中國國家標準(CNS〉A4规格(210X 297公釐)
B 五、發明説明(179) 經濟部中央標準局負工消费合作社印製
No. R2m R3 R4 R5 败逋 11.23 Η ch3 4—F— c6H4 昏 c3h7 油.;IR (:薄稱): 975, 1113, 1129, 1158, 1225, 1256, 1284, 1508, 1634, 1710, 2930, 2960 11.24 Η ch3 4-F- c6h4 IE-c4h9 '油;IR ( 1000, 1013, 1112, 1130, 1225, 1256, 1284, 1508, 1635, 1710, 2920, 2940 11.25 Η ch3 4»F- c6h4 2-甲基丙-1-基 <無.;IR (:薄闕}: 1003, 1029, 1111, 1130, 1225, 1256, 1284, 1508, 163S, 1710, 2950 11.26 Η ch3 4-F- C^H4 第三-CaHo 涵;{薄齲): 973, 1111, 1130, 1189, 1225, 1256, 1365, 1508, 1635, 1710, 2940, 2970 11.27 Η ch3 4-F- c6h4 正-C«H13 1油;IH (薄膜 1002, 1111, 1130, 1226, 1256, 1284, 1508, 1635, 1711, 2933 11.28 Η ch3 4-F- c6h4 3-丙-2~婦-1-基 ; IR (薄膜): 1012, 1058, 1111, 1130, 1226, 1256, 1285r 1509, 1635, 1709, 2940 11.29 Η ch3 4-F— C6H4 炔丙基 *油;(薄膜): 1006, 102B, 1112, 1130, 1226, 1256, 1285, 1509, 1630, 1708, 2110, 2940, 3280 11.30 Η ch3 4-OCH3- c6h4 ch3 通;IR (薄膜): 1035, 1057, 1111, 1129, 1174, 12S3, 1512, 1608, 1633, 1708, 2930 11.31 Η ch3 4-OCH3- CfiH4 c2h5 «油.;IR (薄酹): 1036, 1058, 1112, 1130, 1176, 1254, 1286, 1512, 1634, 1709, 2930, 2960 11.32 Η ch3 4-OCH3- c«H4 £-C3H7 油;:[R (薄糗)ί 990r 1036, 1111, 1129, 1176, 1254, 1285, 1512, 1634, 1709, 2930, 2960 11.33 Η ch3 4-OCH3- c6H4 V8-C3H7 油;IR (薄樹): 972, 1032, 1113, 1129, 1174, 1253, 1286, 1512, 2634r 1709, 2930, 2960 11.34 Η ch3 4-OCH3- c‘H4 [E-C4H, 油;IR (:两膜): Θ38, 998, 1025, 1111, 1132, 1176, 12S4, 1262, 1634, 1711, 2920, 2940 -182- (請先閱讀背面之注意事項再 本紙張尺度適用中國國家橾率(CNS ) A4规格(2!〇 ·<29·7公釐) 五、發明説明(18Q)
7 7 A B 經濟部中央標準局属工消费合作社印製
No. R2” R3 R4 R5 教據 11.35 Η οη3 4-OCH3- c6H4 第三-αΗ〇 油IR (薄摒): 960, 1034, 1111, 1129, 1175, 1190, 1252, 1511, 1633, 1709, 2960 11.36 Η ch3 4-OCH3- c«h4 2-甲基丙-1-基 •涵;IR (簿膜): 1004, 1031, lin, 1129, 1175, 1253, 1512, 1607, 1634, 1709, 2950 11.37 Η ch3 4-OCH3« c6h4 块丙基 涵;IR (.薄膜i): 1006, 1030, 1112, 1130, 1175, 1255, 1512, 1608, 1633, 1707, 2110, 2930, 3270 11.38 Η ch3 4-Cl-C6H4 3_甲基丁-2-烯 -1-基 油;IR (薄膜): 996, 1091, 1111, 1130, 1256, 1284, 1435, 1491, 1634, 1710, 2930 11.39 Η ch3 ch3 ch3 油;IR《薄_): 2930, 1710, 1635, 1284, 1255, 1129, 1110, 1057, 1032, 903, 888 11.40 Η ch3 ch3 c2h5 《油;IR (薄膜… 2935, 1710, 1635, 1366, 1284, 1256, 1130, 1U1, 1044, 919, 891 11.41 Η ch3 ch3 IE-c3h7 吻」IR《簿膜.): 2930, 1711, 1635, 1284, 1256, 1129, 1110, 1044, 1019, 990, 926 11.42 Η ch3 ch3 異-c3h7 ,油;IR (薄膜): 2965, 1711, 1635, 1366, 12Θ4, 1256, 1130, 1113, 986, 914, 894 11.43 Η ch3 ch3 正 -C4H9 《油IR《薄瞬}: 2957, 2936, 1711, 1635, 1365, 1284, 1256, 1130, 1111, 1029 11.44 Η ch3 ch3 撰-C4H9 油.,· IR (薄膜‘): 2956, 1711, 1635, 1366, 1284# 1256, 1130, 1111, 1032, 926 IJ.45 Η ch3 ch3 油J m {薄膜): 2965, 1711, Ϊ635, 1365, 1256, 1192, 1129, 1110, 9Θ4, 930, 894 11.46 Η ch3 ch3 i£-c«H13 油;IR (薄撕): 2934, 1712, 1635, 1365, 1284, 12S6, 1130, 1111, 1058, 1020 -183- (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规格(2i〇X 297公釐) 306908 五、發明説明(181) 經濟部中央標準局员工消费合作社印製
No. Η2* R3 R4 R5 數據 11.47 Η ch3 ch3 (E)-l-氣丙-1 一 婦-3-基 油;(薄隳): 2940, 1709, 1634, 1366, 1285, 1255, 1130, 1110, 1019, 988, Θ93 11.48 Η ch3 ch3 丙-1-摊-3-基 油;IR (薄糈.): 2940, 1710, 1634, 1366, 1284, 1256, 1130, 1110, 1024, 1001, 919 11-49 Η ch3 ch3 丙炔-3-¾ 油;(薄瞩)·· 3269, 2940, 2110, 1702, 1624, 1254f 1245, 1128, 1110, 1025f 995, Θ96 11.50 Η ch3 ch3 3,7-二甲基-2,6 — 辛二烯-1-基. ,浊·; IR (:薄 P): 2932, 1712, 1635, 1436, 1365, 1255, 1130, 1111, 1002, 895 11.51 Η ch3 ch3 3-CF3-C6H4 油;IR (薄瞑‘): 2940, 1710, 1448, 1328, 1281, 1255, 1168, 1127, 1062, 927 11.52 Η ch3 ch3 3—CF3""CgH4*CH2 油;IR (薄膜 2940, 1710, 163S, 1330, 1256, 1202, 1192, 1166, 1128, 1074, 1018 11.53 Η ch3 ch3 3-CF3-CtH4-CH(CH3) 油.;(薄腱): 2925, 1710, 1635, 1329, 1271, 1257, 1204, 1166, 1128, 1073, 892 11.54 Η ch3 ch3 CH2—〇** CH2-CH2 油;IR (薄膜): 2935, 1710# 1634f 1365, 1284, 1256, 1129, 1112, 1057, 1038, 1002 11.55 Η ch3 ch3 6-《4、氯笨基} 己-卜基 油'· IR (薄膜): 2935, 1710, 1635, 1492, 1284, 1255, 1130, 1111, 1029, 1015 11.56 Η ch3 ch3 4 -C1- C5H4-CH2-CH2-〇-CH2-CH2 油;IR (薄膜): 2935, 1709, 1635, 1493, 12Θ4, 1256, 1129, 1112, 1057, 1038, 1015 11.57 Η ch3 ch3 6-(V-铽苯基) 己-丨-基 油;IR (薄P” 2934, 1710, 1635, 1510, 1256, 1220, 1130, 1110, 1029, 1003 II.58 3-C1 ch3 ch3 ch3 熔黏:125-127»C 11.59 3-CJ ch3 c4h5 ch3 熔贴:171-173〇C 11.60 3-C1 CHj C‘Hs c2h5 熔贴《 128-131°C (諳先閱績背面之注意事項
本紙浪尺度適用中國國家標準(CNS ) A4規格(210X 297公* ) A7
7 B 五、發明説明(182)
表 III 經濟部中央梂準局負工消费合作社印裝 R5〇N °^θ~ (R2} m 0 No· R2» R3 R4 R5 歟據 III.l H ch3 C6Hs ch3 油.;3:R【cm·1】(薄膜>: 693f 764, 872, 892, 1005, 1035, 1207, 1253, 1435, 1716, 2920 III.2 H ch3 c6hs c2hs 油IR [cnrl](薄臢): 766, 927, 978, 1012, 1036, 1208, 1253, 1435, 1444, 1717, 2960 III.3 H ch3 c6h5 正 -c3h7 油j IR【cnr1】(薄瞩t): 693, 766, 988, 1037, 1067, 1208, 12S3, 1435, 1717, 2965 III.4 H ch3 CeH5 異-c3h7 油;IR【cnr1](薄膜1): 766, 974, 1037, 1121, 1208, 1253, 1370, 1435, 1717, 2975 III.5 H ch3 c6h5 J-C4H9 ,油·; IR [cm-y (薄願 >: 766, 977, 1015, 1033, 1208, 1253, 1434, 1718, 2934, 2957 III.6 H ch3 c6h5 第三-C4He 油·; IR【cm-i】(薄_ ): 696, 766, 972, 1036, 1190, 1207, 1253, 1364, 1718, 2978 III.7 H ch3 C4H5 3-甲碁丁 -2-烯-1-基 油·? IR【cnri】(薄顏.): 693, 766, 981, 997, 1036, 1207, 1253, 1435, 1444, 1717, 2930 III-8 H ch3 ch3 UyJ—CH2— ]—/ch3 CO2CH3 IR [cm-i] (KBr) 7S9, 925, 991, 1017, 1036, 1177, 1209, 12S3, 1435, 1715 III.9 H ch3 C‘HS 正-C‘Hi3 油 i IR (薄 693, 766, 1013, 1036, 1208, 1253, 1434, 1718, 2932, 2953 -185- (請先閲讀背面之注意事項* 卜本頁) 本紙張尺度適用中國國家棣準(CNS ) A4規格(210X297公釐) Α7 Β7 五、發明説明(185 )
No. R2« RJ R4 R5 km III.10 H ch3 c6H5 炔内* 油;IR (薄瞬): 694, 765, 929, 1007, 1032, 1209, 1254, 1434, 1444, 1715, 2100, 2930, 3270 III.11 H ch3 ch3 ch3 油L; IR (薄禊): 2918, 1718, 1435, 1366, 1252, 120B, 1034, 903, 888, 761 III-12 H ch3 ct3 c2h5 油;π (薄瞬.): 2970, 2940, 2925, 1719, 1435, 1366, 1252, 1208, 1038, 983, 920, 890, 761 III.13 H ch3 ch3 正-C3H7 涵,,·找(薄膜}: 2964, 2935, 1719, 1435, 1365, 1252, 1037, 1019, 989, 926 III.14 K ch3 ch3 異·〇3Η7 油?工R (薄澳” 2970, 2925, 1719, 1366, 1252, 1036, 1017, 985, 944, 936, 913, 893 III.15 H ch3 ch3 E-CiH, 油;找(薄膜): 2958, 2934, 1719, 1434, 1365, 1252, 1208, 1031, 983, 891 III.16 H ch3 ch3 異-c«h9 -油·; IR (薄_)ί 2957, 2929, 1719, 1435, 1365, 1252, 1208, 1033, 980, 926 III.17 H ch3 ch3 第三-CaHo 涵;IR (薄隳): 2980, 1720, 1366, 1252, 1194, 1036, 1018, 983, 930, 918, 893 III.18 H ch3 ch3 £-CjHi3 油;IR (薄_): 2954, 2932, 1720, 1434, 1365, 1252, 1036, 984, 921, 897 111,19 H ch3 ch3 氯丙-i- 烯-3-¾ 油;u (薄Μ): 2940, 2920, 1717, 1435, 1366, 1253, 1208, 1020, 983, 934, 894, 761 III.20 H CHj ch3 内-1 油;IR ( _薄隳): 2950, 1719, 1435, 1366, 1253, 1208, 1026, 919, 890, 761 III.21 H CHj ch3 丙炔-3-* 油;IR (薄斛 3290, 2950, 2930, 2125, 1717, 1435, 1366, 1254, 1208, 1033, 1009, 8Θ1 .186- (請先閲讀背面之注意事項再IPc本頁) 本紙張尺度適用中國國家糅隼(CNS ) A4规格(210X 297公簸) A7 B7 五、發明説明(184) 經濟部中央橾隼局負工消费合作杜印袋
No. R2b R3 RS 敢邯 III.22 H ch3 ch3 3,7-二甲基-2.6-辛二烯-1-¾ I油;IR (薄胸.}: 2967, 2928, 1720, 1435, 1376, 1365, 1252, 1015, 838 III.23 H ch3 ch3 3-CF3-C6H4 油;IR (薄膜): 2950, 1717, 1449, 1328, 1281, 1253, 1210, 1169, 1126, 927, 900 III.24 H ch3 •ch3 3-CF3-C6H4-CH2 ,油;IR (薄膜): 2940, 2920, 1717, 1366, 1330, 1254, 1202, 1166, 1127, 1074, 1034, 884 III.25 H ch3 ch3 3—CF3—CgH4-CH(CH3) «油.;IR (薄膜): 2980, 1717, 1329, 1269, 1255, 1204, 1166, 1126, 1073, 1014, 704 III.26 H ch3 ch3 c6h5-ch2-ch2«o- CH2-CH2 油,;IR (薄膜》: 2940, 1717, 1435, 1365, 1253, 1121, 1036, 983, 893, 750, 700 III.27 H ch3 ch3 6-(4'-氛苯基) 己-1-基 油;(薄膜” 2933, 2857, 1717, 1492, 1365, 1253, 1092, 1034, 1015, 987 III.28 H ch3 ch3 4-Cl-C6H4_CH2- CH2-0-CH2-CH2 •油;IR (薄膜> : 2940, 2920, 1717, 1493, 1365, 1253, 1122, 1091, 1037, 1016, 983, 894 III.29 H ch3 ch3 6-(4<-氣苯基) 己十塞 油;IR (薄膜}: 2933, 2858f 1717, 1510, 1365, 1254r 1221, 1157, 1034, 893 III.30 3-Cl ch3 ch3 ch3 熔點:60-61°C III.31 3-CX ch3 c«h5 ch3 油IR (薄膜): 1037, 1256, 1435, 1444, 171Θ, 2930 III.32 3-C1 ch3 ' I csh5 c2h5 油」IR《薄蜈): 1038, 1256, 1435, 1443( 1718, 2940, 2970 (請先閱讀背面之注意事項需本頁) —1 87— 本紙張尺度遑用中國國家標準(CNS〗Α4规格(210Χ297公* ) θ〇69〇8 A7 B7 五、發明説明(185) 對抗有害真菌作用之實例 有可能以下列試驗顯示通式I化合物之殺真菌作 將活性化合物製備成溶於混合物之2 0 $強度轧劑 合物係由7 0重量西分比環己銅,2 0重董百分比N e k a LN (Lutensoi® AP6,具有乳化及分散作甩之濕削 氧化烷基酚為主)及10重量百分比Emu 1 ph or® EL E ra u i a n E L ,M乙氣化脂昉酵為主之乳化劑), 稀禪成所欲濃度· 小麥徽菌崔提西變種(v a r . t r ί t i c i ) 先用活性化合物之水性製劑(含2 5 0 p p m )處理小 H (Kanzler變種)。約24小時後1將小麥徽菌之孢 麥徽菌崔提西變種)灑在植物上。依此方式處理植 20-22¾ 且在相對大氣濕度75-80¾下培莆7天》然 真菌發展之程度。 此實驗中,用本發明化合物處理植物顯示15¾或 到真菌侵襲,用已知活性化合物處理植物(化合物 號,表3 ,EP-A 463 488 )顯示40¾受到輿菌侵襲 處理植物受到70¾輿菌侵襲。 在對應實驗中(Ka η z 1 e r變種之小麥苗,施用率6 ),其中植物先受到感染及培窗,然後用活性化合 ,依本發明化合物處理植物顯示5 Si或更少受到輿菌 用已知活性化合物(化合物第195號,表3 ,EP-A 48S)處理植物顯示有25¾受到真菌侵襲且未經處理 ‘ 6 0 «受到侵襲。 用: 、該混 nil® ,以乙 ( 且用水 麥苗Μ 子(小 物在 後鑑定 更少受 第195 且未經 3 ppm 物處理 镘襲, 463 植物有 1 1 8 3 - 本紙铁尺度適用中國國家揉準(CNS ) A4规格(210X297公釐) A7 B7 五、發明説明(186) 對抗動物害蟲作用之實例 有可能下列試驗顯示逋式I化合物之殺蟲作用: 將活性化合物製備成 a) 0.1¾強度之丙嗣溶液或 b) 0.1¾強度溶液於混合物之乳液,該混合物係20¾強度 乳劑,該混合物係由70重量百分比環己酮,20重量百 分比 N e k a n i 1 L N ( L u t e n s ο 1 °» A P 6,具有乳化及分 散作用之濕酬,以乙氧化烷基酚為主)及1 0重量百分 比Emulpho「® EL(K乙氧化脂肪醇為主之乳化蝌)且 在a)中用丙_或|3)中用水稀釋成所欲灑度。 實驗終了後,鑑定每個情形中化合物最低濃度且與未經 處理之控制姐試驗相較仍引起80至100¾抑制率或死亡率( 作用閥或最小之濃度)。 黑蚊接觭作用 用水性有效化合物製劑處理嚴重慼染之矮豆(Vicia f a b a ) 。2 4小時後決定死亡率。 此試驗中,本發明化合物1.67, 1.68, 1.71, 1.72, 1.73, 1.98, 1.105, 1.106, 1,109, 1.110, 11.02, 11-05, 11.09, 11.12, 11.13, 11.14, 11.16, 11.24, 經濟部中央樣準局貝工消费合作社印製 I I . 1 〇 2 , I I I . 〇 1 , I I I . 0 2 及 I Π . 1 0 顯示作用閥為 4 0 0 p p m 或更少。 綠色稻米禁蚱蜢接觸作用 用水性活性化合物製蜊處理圓形濾器然後Μ 5個挺蚱蜢 /成癥佔據。2 4小時後評估死亡率。 -18 9- 本紙張尺度適用中國國家揉準(CNS ) Α4规格(210X297公釐) 經濟部中央橾準局貝工消费合作社印製 〇〇69Q8 A7 B7 五、發明説明(187) 此 試 驗 中, 本 發 明化 合 物 1 . 6 8 * 1.81 » I . 82 * I · 8 3, I . 96 » II .09 , ί I . 12, I : 1.1 3 , 1 I . 14, II .1 9 , I I . 27及 I I I . 02 顯 示作 用 閥 為0 . 4 奄 克 或 更 少。 埃 及 棉 葉 蟲接 觭 作 用 用 水 性 活性 化 合 物製 劑 處 理 m 器 並K 5 隹 Μ 幼 蟲 佔 據0 4 小 時 後 進 行第 次 評估 〇 若 至 少 有 一隻 幼 蟲 仍 存 活 ,加 人 飼 料 混 合 物。 2 4小 時後 決 定 死 亡 率 〇 此 試 驗 中, 本 發 明化 合 物 I . 8Z 1.95 » I .36 » I . 10 5. I . 106, 1.112 * I 丨:.0 3 , II. 09 » 11.11, I j · 12 II .13. II .1 4, 1 1.16 » I [ .18 , I 1 . 19 * II .20 , I I . 22 » II .23 , II .24 , I 1.25 » 11: • 1Ί、 II. 28 • II • 2 9 及 I II .1 0 顯 示作 用 閥 為 0 . 4 奄克 或 更 少 ° 一 般 紅 蜘 蛛蟎 接 觸 作用 用 水 性 活性 化 合 物製 劑 處 理 具 有 連生 _- 對 葉 Η 之 培栽 矮 豆 〇 24小 時後 用 厭 重慼 染 葉 Η 慼 染 植物 〇 在 溫 室 中 12天 後 決 定 侵 m 力。 此 試 田6 m 中, 本 發 明化 合 物 I . 07 • 1.95 * I . 105, I .106 * I . 107, I .109 * I . 110, ] [I . 03 > II .04 , I 1 . 06 ♦ II .0 7 , II .09 , I 1.10 * I ! .16, ] :. 18 » II .19, I 1:. 20 * II .22 , I I .24 , [ 1.25 I i .26 , ] Π · 2 7 » II ‘ 28 及 I I . 29 顯 示 作用 閥 為40 0 ppm或更少。 一 1 9 (〉- (請先閲讀背面之注意事項再填寫本頁) t, 裝. 訂 本紙張尺度通用中國國家標準(CNS ) A4規格(210 X 297公釐) 公告木 .............. ❿ή)〆 —-----^ d 補充 第84100978號專利申請案 中文補充説明書1(85年7 、 實驗報告 對抗有害眞菌之補充實例 下列試驗説明式I化合物之殺眞菌作用: 取活性化合物於含70重量%環己酮、20重量% Nekaml ® LN (Lutensol® AP6,以乙氧化烷酚爲主之具乳化及分散作用之濕化 劑)與10重量% Emulphor㊣EL(Emulan® EL,以乙氧化脂肪醇 爲主之乳化劑)之混合物中製成強度20%之乳液,並加水稀釋至所 需濃度。 所採用之對照化合物爲EP-A 463 488之表II中活性化合物No. 497。 對抗禾白粉菌(Erysiphe gramiuis var, tritici)(小麥粉徽)之作用 在小麥苗(品種Kanzler)之葉子上,首先以活性化合物之水性製劑處理 。約24小時後,在植株上撒上小麥粉徽之抱子(Erysiphegraminisvar. tritici)。依此方式處理之植物於20至22〇C及相對大氣濕度75至80%下培養 7天。然後測定眞菌發展程度。 本試驗中,以63??111根據本發明化合物1.01-1.08,1.10,1.15,1.19-1.22, 1.31, I.33-I.35, 1.40, 1.41, 1.44, 1.46, I.48-I.53, 1.65, I.68-I.73, 1.75-1.77, 1.79, 1.80, 1.82, 1.85, 1.89, 1.90, 1.93-1.99, 1.103, I.105-I.107, 1.111, 6820-HRC.DOC/HYC 9 1.113, I.121-I.123, II.〇l-H.〇7, ΙΠ2-Π.32, 11.36, II.39-II.51, III.01-IiL〇8 及III.11-III.28處理之植物之受害程度爲15%或以下,而以相應量之已知 活性化合物(EP-A463 488,表Π,N〇 497)處理之植物之受害程度則爲 40%,未處理(對照組)植物之受害程度爲。 在相應試驗中,以63 ppm對於原文第3頁以後之根據本發明化合物 A. 01, A.06, A.07, A.09, A.15-A.19, B.03, B.05, B.06, B.08, B.13, B. 16, B.21,C.(H-C.03, C.05-C.14及C.16處理之植物展現之受害程度爲 15%或以下’而以相應量之已知活性化合物(Ep-A463 488,表π,N〇 497)處理之植物之受害程度爲40%。未處理(對照組)植物之受害程度則爲 70%。 在小麥苗(品種Friihgold)之葉子上,首先以活性化合物之水性製劑處 理。約24小時後’在植株上撒上小麥粉黴之孢子(Erysiphe var tritici)。依此方式處理之植物於20至22〇C及相對大氣濕度75至80%下培養 7天。測定眞菌發展程度。 本試驗中,以250 ppm根據本發明化合物A.25-A.30,A.32-A.34, A.38-A.40, A.42, A.44, A.46-A.56, A.59, A.70-A.73, A.75-A.82, A.84-A.85, B.23-B.39, B.41-B.50, B.53-B.58, B.61-B.65, B.67-B.71, C.17- C. 29,C.31-C.33, C.35-C.36, C.39, C.41-C.47, C.49-C.50, C.53-C.59處理 之植物展現15°/❶或以下之受害程度,未處理(對照組)植物之受害程度則 爲 70%。 682G-HR.C.DOC/HYC 9 對抗隱匿柄銹菌(Puccinia recondita)(小麥鋒病)之作用 在小麥苗(品種Kanzler)之葉子上,撒上小麥銹病孢子(柯^出^ recondita)。依此方式處理之植物在2〇至22°C及相對大氣濕度9〇至95%下 培養24小時’以水性活性化合物製劑處理。再於2〇至22°c及相對大氣濕 度65至70%下8天後,測定眞菌發展程度。目視評估。 本試驗中,以250 ppm根據本發明化合物1.05, 1.07, 1.22,1.31, 1.51, I. 82-I.83, 1.91, I.94-I.99, I.105-I.107, 1.109, 1.110, I.121-I.125, II.01-II.07, II. 09-II.15,IU7-II.48,11.51,11.54,11.56,11.57,ΙΙΙ.01-ΙΠ.05, 111,07, IIL09-III.16,111.18,111.19,II.26與EGL28處理之植物展現5%或以下之受 害程度,而以相應量之已知活性化合物(EP-A 463 488,表II,No. 497) 處理之植物則展現25%之受害程度,未處理(對照組)植物之受害程度爲 60%。 在相應試驗中,以250 ppm列於原文第3頁以後之根據本發明化合物 B. 02-B.04,B.06-B.09,B.11-B.21, C.01-C.03,C.05-C.07,C.09 與 C11- C. 14處理之植物展現之受害程度爲15%或以下,而以相應量之已知活性 化合物(EP-A 463 488,表II,No. 497)處理之植物之受害程度則爲25% 。未處理(對照組)植物之受害程度則爲60%。 對抗葡萄生單私板(Plasmopara viticola)(葡萄霜撤(Vkie Penmospora))·之作用 在盆栽葡萄(品種Muller Thurgau)之葉子上,先以活性化合物之水性 製劑處理。約8天後’以葡萄霜徽抱子(piasmopara yitic〇la)(vine 682G*HRC.DOC/HYC 9 306308 上策气德和玄
Peronospora)感染葉部。依此方式處理之葡萄先置入24 C之 # @ #内16小0寺 内48小時後,置於20至30°C之溫室内5天。植物再置入濕軋東 ,加速脱離孢囊梗。然後評估葉子背面眞菌發展程度。 .λ ^46- 本試驗中,以250 口?111之根據本發明化合物八.24,八.264-’ λ 79-A-81? Α.49, Α.51-Α.60, Α.62,Α.64-Α.71, Α.73-Α74 Α.76-Α.77,八· _ r 70-Β.71, Α.84-Α.85, Β.22-Β.25, Β.28-Β.35, Β.38, Β.40, Β.43-Β-68, C.17-C.18, C.21-C.24, C.26-C.33, C.35-C.37, C.39-C.47, C.49-C.57處理 之植物展現之受害程度爲或以下;未處理(對照組)植物之交害私度 爲75%。 ^ 表A(補充表I)
no. X R1 R2m ΊΓ kT-— R5 mp‘ P’C] A.01 ΝΟΟΪ3 ch3 H CH3 1-CH3)4-C1-吡唑-3-基 CH? 128-129 A.02 noch5 CH? ci CH3 uCH3!4-C1 — 嘥唑-3-基 CH7CH3 99-100 A.Q3 NOCH3 ch3 H CH? ^0113, 4-C1- .. 咄唑-3-基 ch(ch3)2 143-144 A.04 NOCH3 ch3 H 'CHiCH? ch,c.h3 «5-87 Α.ΰ5 NOCH3 CH3 H CH3 IQh5 .…~~ CH^COoCHj 88-99 A.〇6 NOCH3 CH3 H CH3 〔6打5 CH9CONH2 82-S4 A.07 NOCH3 ch3 H CH3 CH3CH2〇CH^ 85-86 A.08 NOCH3 ch3 K ch3 CH2CN (CH2)2CH3 122-123 A.09 NOCH3 ch3 H CHs 塞哇-4-基. 油 A. 10 NOCH3 ch3 H Oh &2s CH(CH3)C〇7CH3 油 682G-HRC.DOC/HYC 令 -4 - 4 no. X r! A R3 R4 nip. [°C] A.ll NOCH; CH? H ch3 QH5 CH(CH5)CO〇CH- (CH3h 油 A.12 NOCH3 CH; H ch3 c<;H5 CH2C02CH(CH3)2 32-84 A. 13 NOCH3 CH? H ch3 c6h3 CH:C02C(CH3>3 73-74 A,i4 NOCH3 CH; H CH7 C6H5 CK(CHjJCON- fCH3)2 油 - A. 15 nochj ch5 H CH2CH3 QHs CHfCHi)7 油 A.16 n〇ch3 ch3 H CH2CH3 QH5 (CH2)?CH3 油 A.17 NOCH3 CHi H CH2CH3 C6H5 ch2ch=ch2 油 A.iS NOCH? CH3 H CH2CH3 C5H5 CH:C-CH 1- 油 A.19 n〇ch; ch5 H CHi 的匕咬-3-基 CH,-[3-CF3-QH43 油 A.20 NOCH3 CH3 H ch3 卜CH3-:吡唑-3-差. ch-」ch3 油 A.21 NOCH3 CH3 H ch3 l-CH〕-咐嗅-3-基[ (CH;hCH3 油 A.22 noch:. CHj H CHi 吡唑-3·基 CH(CH?)2 油, A.23 NOCH3 CH} H CR:,;' 1-峻-3-基 (CHi)5CH? 油、 Λ.24 NOCH3 CH-, H CH] Qh5 CH(OT)C02CHr C H3 油 A.25 NOCH3 C'H? H CK3 2,4-CVQ* CH2CH-CH2 92-95 A.26 NOCH? CH; H CH-; 2,4-ClrCfiH3 CH2CH=C(CH3)2 62-66 Α·27 NOCH.? CH3 H CH? P塞吩基 ch3 86-87 AM NOCHj ch3 H ch3 '"塞吩-3-基 ch:ch3 油 A.29 NOCH3 ch3 H CH; "塞吩-3-基 CH2CH2CH.1 63-64 A.30 NOCH3 c:h3 H CH3 p塞吩-3-基 CH(CH3)2 ik A31 noch3 CH; H CH:, 11塞吩-3-基 ch2c=ch 79-82 A.32 NOCH? CH? H CH, p塞吩-3-基 ch2ch=ch2 油 A.33 N0CH3 ch3 H ch3 吡啶-4-基 ch3 A.34 nochj CHj K ch3 ϊ»比症-4-基 CH2CH3 76-S0 A.35 NOCH3 CH; H CH3 巧匕淀-4-基 ch2ch2ch3 油 A.36 NOCHj ch3 H ch3 p比0S>4-基 CH(CH3)1 油 Λ.37 NOCH3 CRi H CHj ρ比淀-4-基 CHiCs CH 油一, Α_3δ NOCHj ch3 H ch3 口主吩-2-基 ch2c*h3 76-8ΰ - A. 39 NQCH3 ch3 H CH3 塞吩-2-基 CH2CH2CH3 油 A.40 NOCH3 ch3 紝 CH? ,塞吩-2-基 CH(CH3)2 油 A.41 NOCH; ch3 H CH.7 Ρ基吩_2·墓 CH2CH2CH2CH3 油 A.42 NOCH3 ch3 H CHi »塞吩-2-基 CHiCH=CH2 60-63 A.43 NOCH3 ch3 ii c.h3 塞吩-2-基 CH2-CH=CCCH3>2 油 Λ.44 NOCH; ch3 ;{ CH? 2.4-C12-C6Hi H 129-131 A.45 NOCH3 ch3 H CHi 2,4-Ch-CiHi CHiGv 油 Λ.46 NOCH3 CH3 H CH] 峨咬-2-基 CHj 油 A.4? NOCH? ch3 H ch3 ' p比症-2-基 CH2CH2CH3 油 A.48 NOCH3 ch3 H CH? 峨淀-2-基 CH(CH3)2 油 A.49 N〇CH? ch3 H ch3 17比症**2-基 CH2CH2CH2CH? 油 5 no. X R1 R2n R3 R4 R5 mp. [°C] A.50 NOCHj ch3 H CH3 竹匕咬-2-基 ch:ch=ck2 油 A.51 NOCH3 CH? H ch.5 3:CH(CH3h: 異g嗤- ch3 75-77 A.52 NOCHj ch3 H CH.i 2-C0H5- p咢哇-4-基 CH3 136-13¾ A.53 NOCH3 ch3 H (¾ ^CH(CH3)CH2^ CH:t-異哼唑基 ch3 油 A.54 NOCH3 c:h3 H CH3 -3-CH(CH3jCH2^ ClHy 異 yi CH2CsCH 油 Λ.55 NOCH3 ch3 H CKj 3-C(CH3'm-異号唑-5-基 CH2CH20CH3 i- 油 A.56 NOCH3 ch3 H CH; 3-C('CH3)3. 異"号唑-5-基 ch3 90-93 A.57 NOCH3 ch3 H ch3 3-C(CH3)3-異"号唑-5-基 H 57-60 A.58 NOCH3 CH3 H CH^ 3-CH(CH))CTL·-CHr異嘮唑-5-基 H 105-107 Λ.59 NOCH3 CH? H CH.i * 3-CH(CH^)CH2-CHj-異》咢唑-5-基 CH2CH20CH3 油 A.60 NOCH·; CH? H ch3 3-CH2CH2CH3-異1^等唾-5-基 CH3 80-82 A.61 N0CH3 CHi H ch3 峡1"南-3-基 CH? 96-99 A.62 NOCH3 ch3 H ch3 3-CH2CH2CH.r 異p号峻_5-基 ch2c^ch 59-62 A.63 NOCH3 ch5 H ch3 3-CH2CH(CK3)2-異嘮嗖-5-基 ch2-c = ch 油 aM n〇ch3 CH, H ch3 3-ai2CH(CHV)2- 異-号唑-5-基 ch3 59-61 A.65 noch3 CH3 H ch3 2-CVH5·崎唑_4_基 CH2ChCH 103-104 A.66 noch3 CH; H CH3 ρ 比遠 _2-基 Clh 126-127 A.67 N〇CH? ch3 H ch3- I-C0.H5-吋t啶-4-基 ch3 91-93 A.68 NOCH3 CH:1 H CH, 4-N(CH3)2-C6H4- ch2ch3 S8-92 A別 noch3 ch3 H . ch3 4-N(CH〇rQH4- CH? 92-95 A.70 NOCH3 ch3 H ch3 Br CH3 油 A.71 NOCH3 ch3 H ch3 CN ch3 110-112 A.72 NOCH3 ch5 H OC2H5 csh5 CH? 53-55 A.73 NOCH3 CH> H 〇-α-〇3Η7 c6h5 CH? 36^38 A. 74 NOCH3 ch3 H 0-i-C3H7 〇h5 ch3 87-S9 A. 75 NOCH3 ch3 H O-CI-C4H9 C^Hs ch3 油 A.76 NOCH3 ch3 H nh2 C6H5 ch3 油 A.77 NOCH3 ch3 R NHCH3 c6h5 ch3 74-77 A.7S NOCH3 ch3 H N(CH3)2 C^Hs ch3 62-65 A.79 NOCHi ch3 Fi OC2H5 CH3 ch3 油 A.SO NOCH3 ch3 H Br J CH? 0¾ 92^6 A.S1 NOCH3 ch3 H SC2tis CH? CHs 油 A.82 NOCH3 ch3 H NHCHj (¾ ch3 油 A.33 NOCH? CHj H NHCH3 4-C]-C6H4 CHjC^CH 1lg-U9 -6- 6 306908 no. X R1 R2.t. K} R4 R5 mp. [°C] A.S4 NOCH] ch3 6-CH3 nhch3 4-F-CgHu ch3 93-97 A.85 noch3 ch3 4-OCH3 NHCHj 4-F-QH4 Oil 油 A.86 NOCH3 ch3 H CH3 2.4-C12-QH3 CH3 130-i32 A.87 N0CH3 CHj H ch3 OCH2CH3 (¾ 油 A.SS N0CH3 ch3 H ch3 0(CH2>2CH3 CH3 油 A.89 MOCH3 ch3 H ch3 OC.H(CH3h CH.^ 油 A.90 NOCHi CH3 K ch3 0(CH2)5CH; CH? 油 A.91 NOCH3 ch3 H CH; OCH.CH-CH2 ch5 油 Λ.92 NOCH3 cu3 H ch3 OCH2-C6H5 ch3 油
表B(補充表II) no. X R1 R3 R4 R5 mp. [°C] B.01 choch3 CH3 H H 2,4-Cl2-C6H3 CH2CH3 油 B.02 CHOCH3 CHi H H 2,4-α2-〇όΗ.ι 油 B.03 CHOCH3 ch3 H CH2CH3 QH5 ch2ch=ch2 油 B.04 CHOCH3 ch3 H CH2CH3 CH2CsCH 油 B.05 CHOCH3 -ch3 H CH7CH3 QH5 CH2CH=C(CH3)2 油 B.〇6 CHOCH3 ch3 H ch3 異 4峻-5-基 ch3 油 Β,(Γ7 CHOCH3 ch3 H ch3 3-CHr異呤唑-5-基 CH2CH=CHC1 (E) 油 B.OS CHOCH3 ch3 H ch3 3-CHr異^峻-5-基 ch2chch2 油 Β.09 CHOCH3 ch3 H ch3 3-CHr異哼唑-5-基 (CH2)3CH5 油 Β.10 CHOCH3 ch3 H ch3 3-CH3-異今唑-5-基 香葉草基 油 Β.Π choch3 ch3 H ch3 3-CH;r異咩唑-5-基 CH2-[3-CF3-C0H4] 油- B.12 CHOCH3 ch3 H CH? p塞吩-3-基 ch2ch=ch2 油 3.13 CHOCH3 ch3 H ch3 -塞吩-3-基 ch2c-ch 油 B.14 CHOCH3 ch3 H ch3 4-0¾¾ CH2CH=CC1-CH3 油 B.15 choch3 ch3 H CHj 4-CK6H4 CH2CH=CHC1 (Z) 油 B.16 CHOCH3 c.h3 H CH3 4.CI-C6H4 CH2C(CH3)=CH2 油 Β.Π CHOCH3 ch3 H ch3 4-α-€〇Η4 CH2C(Ci)==CH2 S9-91 Β.Ι8 CHOCH3 ch3 H ch3 4-Cl-QH4 CH2C(Br)«CH7 油 Β.19 CHOCH? ch3 H ch3 4-C1-QH4 ch2ch==chch3 油 Β.20 CHOCH3 ch3 H CH/ 4-a-CfiH4 CH2CH2CH=CH2 油 Β.21 CHOCH3 CHj H CH3 4-CI-C0H4 CH(CH3)CsCH 油 Β.22 CHOCH3 ch3 H ch3 4-ci-c6H4 H 56-59 -7- 7 no. X R: R2m R3 R4 R5 mp. [UC] B.23 CHOCHg ch3 H CH; 4-F-C0H4 Η 油 B.24 CHOCH^ CK3 H ch3 LF-QH4 ch2~ch=ch2 油 B.25 CHOCH3 CH】 H CH; 4-f-C6H4 ch?.cci-ch2 油 B.26 CHOCH? ch3 ri CHi 4-F-QH4 CH:-CBr=CH2 油 B.27 CHOCH3 ch3 H CHi CH2-CH-CGCH3 油 B.2S CHOC& CHj H ch3 4-F<:6Ha CH2-C(CH3)=CHi 油 B.29 CHOCH3 CH; H ch3 4-F-QHj CH(CHv)-C = CH 油 B.30 CHOCH3 CH. H . ch3 ^-F-C:6H4 (Z) -ch^chchci 油 B.3I CHOCH3 CH: H ch3 4-F-QH4 CH2-CH=C(CH5)2 油 B.32 CHOCH? CHi H CH; 4-F_C6H4 CH2-CH=CH-CH3 油 B.33 CHOCH;! CH., H CH; 4-F-C5H4 CH:-CH=CHBr 油 B.34 CHOCH3 CH^ H ch3 4-F-C6H4 CH2CH2〇H=CHa 油 B.55 CHOCH, CH: H ch3 4-Br-C6H4 CH2CH-CH7 油 B.36 CHOCH3 ch3 H CHi. 4-Br-C5H4 CHi-C-CH 油 B.37 CHOCH3 CHi H CH3 4-Br-C6H4 CHiCH=CiCH')2 油 B.38 CHOCH3 CH3 H CHj 3-G-QH4 CH.CH-CHi 61-64 B.39 CHOCB3 CH:1 H ch3 3-Cl-QH4 ch2c^ch 88-90 B.40 CHOCH3 CH; H (¾ 3-CI-QH4 CH:CH=C(CH?)2 60-63 B.4I CHOCH5 CH3 H ch3 2A"C\7-C6Er ch2c-ch 油 B.42 CHOCH. ch3 H ch3 2,4-a2-C6H3- ch2ch 二 a!2 73-77 ΒΛ3 CHOCK. ch3 H CH? 2,4-a2-QHr CH2-CH=CiCH5)2 油 B.44 CHOCH3 CH3 H CHi 塞吩冬基 CH2Cfi=CH7 55-5S B.45 CHOCH3 CH; H ch3 β塞吩-2-基 CH2ChCH 59-63 B.46 chochj .CHj H CHj 嘍吩-2-基 ch2ch=c(.ch3)2 油 β.47 ch〇ch3 ch3 H ch3 ρ比咬-2-基 CH.ChCH 油 B.48 ch〇ch3 CH] H ch3 叶匕咬-4-基 ch2ch=ch. 油 B.49 CHOCH.7 CH3 H CHj ρ比咬-4-基 CH2C ^ CH 油 B.50 CHOCH3 CHj H CH3 3-CH(CHih- 異嘮唑-5-基 ch2c^ch 油 3.51 CHOCH3 CH.i H CH? 3-C(CH3)3-異号峻-5-基 CH2C-CH 102^105 B.52 CHOCH3 CH3 H ch3 2-C$H5-,号峻-4-墓 CHaCsCH 油 B.53 CHOCH; CH; H CH, 3-CH(CH„〇CH2-CH3·異嘮唑-5-基 CH2OC.H 油 R.54 CHOCH.1 ch3 H CH; 咬喊-3-基 CH2C-CH 73-76 B.55 CHOCH; CH? H CH. 竹匕岐-4-基 CH3 104-107 B.56 CHOCH3 ch3 H 0¾ 3-CH,CH2CH3-異噚唑-5-基 CH^C-CH 59-61 B.57 CHOCH3 ch3 H CHj 3-CH2CH2CHv 異^哇-5-基 (¾ 油 B.5S CHOCH3 CH;: H ch3 3-CH2CH2CH3-異°号吐-5-基 油 B.59 CHOCH3 ch3 I H ch3 3-CH2CH(CH3)2' 異哼唑-5_基 CH3 油 -8- 8 .306308 no. X R; R4 R5 mp. [yC] B.60 CH〇€H3 ch3 H ch3 3-CH2CH(CH3),_-異咩唑-5-基 CH2C-CH 油 Β.όΐ CHOCH3 CH? H CHj I-C0H5- 比咬-4-基 CHj S6-88 Β.62 CHOCH.^ CH3 H CHy 1p比咬-4-基 CH2C-CH 油 Β.63 CH〇CH? CH3 H CB) CM CH3 92-96 Β.64 CHOCH3 ch3 K OCH3 C〇H3 CHj 油 Β.65 CHOCH3 CH^ H OC2Hs CfiHs CHj 油 Β.66 CHOCH3 CKj H SCH-j CsHs CH^ 103-105 Β.67 CHOCH3 H SC2H5 CH? CH3 油 B.6'3 choch3 C.H3 H NHCH3 CH3 ch5 油 Β,69 CHOCH3 CH? H NHCHr 4-C\~C6H4 CH^C^CH 94-96 Β,70 CHOCH3 CH3 4-OCH3 NHCH3 4-F-C6H4 CH3 92-95 Β.71 CHOCH3 CHi 4-OCH3 NHCH3 4-F-C6H4 CH^CsCH 115-117 Β.72 CHOCHj CH; H CH3 2,4-Cl2-C6H3 CH3 115-117
表C(補充表III) no. X R1 R2m R3 R4 师,[°c] cm CHCHj CH? H CH3CH3 C〇H; (CH;)2CH3 cm CHCH3 ch3 H CH7CH3 CH(CH3h 油 C.03 CHCH3 ch3 H CH2CH3 QHj CH2CH=CH2 油 c.04 CHCH3 ch3 H ch3 4-C1- p比淀-3-基 ch3 104-106 C.05 CHCH3 CH3 H CH2CH3 c«h5 ch3 油 C.06 CHCH3 ch3 H CH2CH3 c6h5 CH2CH3 油- C.07 CHCH3 ch3 H CH3 3-CH3-異嘮唑-5-基 CH3 油 CM CHCH3 CH3 H ch3 3-0¾ '異β号吐-5-基 ch2ch; 油 C.09 CHCH3 CHi H CHj 3_CH3·異<7号嗅-5-基 (CH,)2CH3 油 C.10 CHCH3 CH3 H CH] 3-CH3-異今唑各基 ch(ch3)2 油 C.M CHCH3 CHi H ch3 3-CH3-異咩唑-5-基 (CH2)3CH, 油 C.12 CHCHj CH; H CH3 3-CH3-異》号峻-5-基 (CH2)sCH3 油 C.I3 CHCH3 CH3 H CH.j 3-CH3·異巧也-5-基 CH2CH-CH2 油 C.14 CHCH3 ch3 H cr3 3-CH3-異》号唑-5-基 CH2CH:CHC1 (E) 油 C.i5 CHCH3 ch3 H CH?, 3-0¾-異今ϋ基 香葉草基- 油 C.16 CHCH? CHi H ch3 3-CM” 異Κ5-基 CHr[3-CFrC6H4] 油 C.17 chch3 ch3 H ch3 吩-3-基 CH? 油 CM CHCHi CH] H ch3 "塞吩-3-基 CE2CH3 油 -9- 9 no. X R! 尺 R·1 R4 R5 mp. [°C] C.19 chch5 CH; H ch3 吩-3-基 CH2CH2CH3 油 C.20 chch3 CH, H CH, «塞吩-3-基 CH(CH„〇2 油 C,2[ chch3 ch3 H ch3 11塞吩-3-基 CH2〇hCH 油 C.22 CHCHj CH3 H ch3 嘩吩_3-基 ch2ch=ch2 油 C.23 CHCH3 CH3 H ch3 B塞吩-2-基 CH3 油 C24 CHCH3 CH? H CHj "塞吩-2-基 CH2CH3 油 C.25 CHCH3 CK; H ch3 噻吩-2-基 CH2CH2CH3 油 C.26 CHCH3 CTI3 H ch3 "塞吩-2-基 CH(CH,)2 油 C.27 CHCH3 CH3 H CH? p比峻-2-基 CHj 油 C28 chch3 CH; H CH? 叶匕淀-2-基 ch2ch. 油 C.29 CHCH3 ch3 H ch3 咄啶-2-.基 ClbC ^ CH 油 C.30 CHC.H3 CH; H CH: p比σ定-2-基 H 油 C.31 CHCH3 H CH:1 ^比*^-4-基 ch3 油 CHCHj ch3 H CH、. 巧匕沒>4·基 CHiC^CH 油 C.33 CHCH3 CH; H ch3 3-CH(CH3j2· 異崎唑-5-基 ch3 油 C.34 CHCH3 CH) H ch3 3-CH2CH2CH3-異·咢峻-5-基 ch2och 油 C.33 chch3 CH] H ch3 3-(:H2CH2CH3-異崎唑_5-基 CH? 油 C.36 CHCH3 CH: H CH? 3-N〇2-QH4 CH: 油 C.37 chch3 CHi H ch3 3-CH2CH(CH3)7- 異啐唑-5-農 ch3 油 C.38 chch3 CH:; H ch3 2-CE2CE(ai3j2~ 異哼唑_5•基· CH7C-CH 油 C.39 CHCH, -ch5 H ch3 4-C(;H5-吡啶_2-基 ch3 油 C.40 CHCHj CH- H ch3 4-C(,H5-吡啶-2-基_ CHiCnCH 油 C.41 CHCH? CI-Ii H ch3 l-C^Hs. p比3备4-基 CHi 油 C.42 CHCH3 CH:; H ch3 1-CH3- nbi-2-ί- CH? 油 C.43 CHCH3 CH? H ch3 i-CH]- p比咬-2-基 C2H5 油 C.^4 CHCHi CH: H CH3 1-CH?-吡唑-2-基 11-C3H7 油 C.45 CHCH3 CH] H CH] I-CH3- i-QH: 油- C.46 CHCH3 CH3 H CE} l-Cflt- 0比峻-2-基 CH2-CH=CH2 油 C.47 CHCH3 CH, H ch3 CN CH3 油 C.48 CHCH3 ch3 H OH QH5 ch5 81-84 C.49 CHCH) CH: H oc2h5 QH; CH; 油 C.50 CHCH3 ch3 H och3 QH5 ch3 L油 C.51 CHCH3 CHj H 0-n-C3H7 QH5 CH; 油 C.52 CHCH3 CH] H 0~i-C?H7 C〇H5 CH3 油 Co5 CHCH3 CM3 H Br QH5 CH; 60-61 C.54 CHCH? CH;. H sch3 c6h5 CH, 油 C.55 CHCH3 ch3 H NH: C6h5 CHi 油 CM CHCH3 CHj H ΝΉαΗ3 C〇Hs ch3 52-5^ -ίο- 10 306908 ao. X Rl R2:U R; R4 R5 mp. [°C) C.57 chch3 ch3 H N(CH3)2 C6H5 0¾ C.58 chch3 ch3 H OC2H5 ch3 CH? 油 C59 chch3 ch3 H NHCH3 ch3 ch3 油 C.60 CHCHb ch3 H CH? 2,4-Ch-QH? ch3 油 表D(新表)
no. X R1 R2m R3 - R4 R5 ιτφ. [°C] D.Oi NOCH3 H H CH3 UH5 CHj 90-93 D.02 NOCH3 H H ch3 4-F-Cf.Hs ch3 104-105 -11- 公告本
as 第84100978號專利申請案 中文補充説明書11(85年7月) 實驗報告 比較下列化合物之生物活性
0
I
no. R3 R4 R5 X a. 1 CK3 2,4 -CI2 -CqH3 ch3 CHO a.2 CK3 2,4,C12-Cs:-:3 CH^CSCH CHO a. 3 CH3 2,4-Cl2-C6:-:3 ch2ch = ck2 CHO a. 4 CH3 2 / 4 - CI2 · ch3 CH a. 5 CH3 2 , 4 - CI2 * C5H3 ch3 NO A H 2,4-Cl2-C5H3 CH] CHO 所採用之對照化合物入爲\¥0 90/07493中第23頁之活性化合物No. 60。 對有害眞菌之作用實例 在下列試驗中測定式I化合物之殺眞菌作用 取活性化合物於含有70重量%環己酮、20重量% Nekanil㊣ LN (Lutensol® AP 6,以乙氧化烷酚爲主之具有乳化與分散作用 之濕化劑)與10重量% Emulphor® EL(Emulan® EL,以乙氧化 ^820-HR.C.DOC/HYC 9 3GS908 脂肪醇爲主之乳化劑)之混合物中製成強度20%之乳液,並加水稀 釋至所需濃度。 對葡萄生單轴徽(Plasmopara viticola)(霜徽(Peronospora))之作用 以活性化合物之調配物(活性成份含量:63ppm)喷麗盆栽葡萄 (品種MullerThurgau)至滴濕爲止。8天後,以葡萄生單軸黴(piasmopara viticola)之游孢子懸浮液喷灑植物。依此方式處理之植物保持在2〇至3〇°c 及高濕度下5天。評估前’植物再保持在高濕度下16小時。目視進行評 估0 no. 受害程度(%) a.l 0 a.2 25 a.3 25 a.4 0 A 60 未處理 80 對稻梨抱(Pyricularia oryzae)稻熱病之作用 以活性化合物之調配物(活性成份含量:16ppm)噴灑稻秧苗(品 種台農67號)至滴濕爲止。24小時後,以稻梨孢之水性孢子懸浮液噴灑 植物。依此方式處理之植物保持在22至24°C及相對大氣濕度下95至99% 下6天。目視進行評估。 682G-HRC.DOC/HYC 9 PIBNi-f 公告束 申請曰期 84.02.07. 案 號 84 100978 Ιηϋ,-ΟΊ6 類 別 ㈤ch A ; , /狄 r ! (以上各樹士本局填柱) $06908 A4 III專利説明書 發明 新型 名稱 發明 創作 人 中 文 英 文 名 姓 國 籍 住、居所 茏乙酸衍生物,其製備方法及中間產物 ,K含其之姐合物
PHENYLACETIC ACID DERIVATIVES, PREPARATION THERHOF AND INTERMEDIATES THEREFOR. AND COMPi)SITinNS CQKTAIHiHG THEM 斯 瑞茲 爾哈爾瑞 拜勒.洛洛 ‘慕特· · 特.瑞茲拉 伯斯伯蘭西 哈路艾法吉 諾恩 門根曼 拉丹默 特格斯ί乂 索-克· •歐·德 特里德哈 伯西哈伯 休華I田艾 1.2.3.5.6.7,8.9.均德國 虎 7 街 谠虎虎 bTFn*r--alr* * 號5 1 普 號3街西2丹號 20爾格高街一 2 達索西克克丹街號 納瑞波泰瑞史113 曼布ΓΡ市布ε格格 洛姆芬ί分肯西高威 號普艾沙沙艾市|爾 4卡市域域市德佛艾 D3納克勞勞德塔市市 市市纳河河塔史罕其 罕罕德恩恩史佛賓拜 曼曼安來來紐西西哈 «國國函國國國國國國 西德德德德德德德德德 裝 訂 經濟部中央標準局員工消费合作社印製 姓 名 (名稱) 德商巴地斯顔料化工廠 國 籍 德國 三、申請人 住、居所 (事務所) 德國來恩河勞域沙孖市卡爾一波斯街38號 代表人 1 .卡爾一菲得里契.班格 姓 名 2 .克勞斯.狄特.Μ芬 -1 -
Claims (1)
- 妄;U 1.00978¾專利由13 案 由文由讀惠利節_修11:申請專利範圍-正·下式I之苯乙酸衍生物或其鹽類 (R2): RsON=C(R')-C{R3)^NOCHf 經濟部中央標準局貝工消費合作社印製 co2r: 其中取代萋及參數具有下勿Θ意義: X 1¾ Ν 0 C H a ' C Η 0 C Η , sC C Η ΓΗ 3 ; R1 係氫戎C , - C 4 -垸基; R 2 偽南素,C t - C 4 -烷基或C i - i.U -烷氣基; in 煤0或1 ; R3 係氪,羥基,胺基,鹵素,烷基,Ct-C4 -垸 氧基,Ct-Cc垸碲基· Cd: Λ-烷胺基或二- Ct-C4-烷胺基; R4,彳系氰亳,鹵素,“-U -烷基,Ct-Ce -烷氣基, C2-C*» -烯氧基*有可能瑄些基團之烴基像部份或完 全鹵化或帶有1至3侗下列基:茏基; 茏基,異噁唑基,基,It唑基,_唑基,_嗯 基,嗎唑基或呋喃基,有可能環吠基係部份鹵化或 帶有1至3個下列基:硝基,Ci-Ce -烷基> Ct-C^-烷氣基,二- Ci-U -烷胺基,苯基; R5 係氡, - 1.. l_Ci〇-综基’C;?_Ci〇-铺基,快基,有可 能瑄些基晒部份鹵化或帶有1至3個下列基··氰基 -1 本紙伕尺度逋用中國國家標準(CNS ) A4規格(210X297公釐) 減 1裝 訂 I 線 (請先閲讀背面之注意事項再填寫本頁) 306908 A8 Β8 C8 … D8 々、申請專利範圍 (請先閲讀背面之注意事項再填寫本頁) ,羥基,胺羰基,烷氧基,Ct-C«-烷氧羰基 ,Ci-Ce-烷胺羰基,苯基或萘基,苯氧基,嘧啶基 ,呋喃基,吡咯基,噁唑基,異噁唑基,1,2,4 -噁 二啤基,_喟基或嗶唑基•有可能環狀基涤部份鹵 化或帶有1至3個下列基:羥基,C t - C β -烷基, “-C«-齒烷基,C3-Ce -環烷基,(^-Ce -烷氧基,苯 基; 笼基,吡啶基,有可ΙΓ這些基團部份鹵化或帶有1 至3個下列基:硝基,_C ! - i U -鹵烷基; 但若R 5為(U - C 4 -烷基且X為C H 0 (: Η 3,R 3則不為氮。 2. 根楝申請專利範圍第1項之苯乙酸衍生物或其鹽類,其 中R 3,R 4及R s具下列意義: r 3 係m *羥基,環丙基·鹵素,c 1 - c a -烷基, Ct - C4 -垸氧萋或Ci-C4 -烷硫基, R4 !系鹵#,Ci-C4 -烷基,C^-Cf烷氧基; 茏基· 5 i雜芳基或吡啶基·有可能埴些基係部份 鹵化或帶有1至3個下列基:硝基,I、-Ce-烷基, C t - 1% -垸氧基,二-C ! - C « -烷胺基,S基; R5 皞氮> 經濟部中央樣率局貝工消費合作社印策 C 1 - C,〇 -烷基,C 2 - U 0 -烯基,c 2 - C i 〇 -炔基,有可 能這些*两部份鹵化或帶有丨至3俩下列基:氰基 ,羥蔫,胺羰基,C^-Ce -烷氣基,U-Ce -烷氣羰基 ,Ct-C«-烷,瞭羰基,茏基或#基,茏氧基,5員雜 芳基或嘧啶基,有可能芳香基及雜芳香基係部份鹵 〇 本紙張尺度逋用中國困家樣準(CNS ) A4见格(210X297公釐) 六、申請專利範圍 4 . A8 Β8 C8 D8 化或帶有1至3個下列基:羥基,C 1 - C β -烷基, C- C «5 - _ 烷基, C3-Ce -環烷基,Ct-Ce -烷氣基,苯基; 笼基,吡啶基,有可能這些基團部份鹵化或帶有1 至3爾下列基:硝基,c t - C β 鹵烷基。 根撺申請專利範圍第1項之苯乙酸衍生物或其鹽類,其 中!n 1¾ 0 根堉申請專利範閜第1項之'笨乙酸衍生构或其馥類,其 由I? 1诶甲*。 ~ 一種弊備甶請專利範阑第1 I自:之茏乙酸衍生物或其薷類 ,包括W太身已知方式將下式II之笮基衍生物 co2ri 〜#------,1τ------^ (請先閲讀背面之注意事項再填寫本頁) 經濟部中央橾隼局員工消费合作杜印繁 其中L1煤親核性取代之離去基,輿下式之羥荖亞薛反應 R 5 0 « = C ( 8 4 ) - C ( R 3 ) = Η Ω Η 丨 Π ) 一棰製燁由請專利範圍第1項之苯乙酸衍生物或其鹽類 ,其中R3及R4非鹵素之方法,包括R本身已知方式將式 I之笮基衍生物 3 - 本紙伕尺度適用中國國家揉率(CNS ) Α4洗格(210Χ297公釐) 306908 A8 B8 C8 D8— (R2). 申請專利範圍(R2)m 其中L 1係親核性取代之離去基,與下式[V之二羥基亞胺 反應 Η 0 N = C ( R 4 ) - C ( R 3 ) = Η 0 Η I V 以產生下式V之化合物 HON=C(R< )_c(R3)=NOCH: C=X I co2r! (請先閲讀背面之注意事項再填寫本頁) 經濟部中央揉準局員工消費合作社印装 然後將V與不式VI之化合物反應 Rs - L2 V [ 其中L 2係親核性可取代之離去基M產生[' 。 一铺製備申請專利範圍第1項之笼乙酸衍生物或其鹽類 ,其中R 3非南素之方法,包括K太身已知方式將式ϋ之 平蓽衍生物 Li-CH· (R2)t II 4 1 I R -X 2 -O c——c 本紙張尺度逍用中國國家標準(CNS ) A4規格(210X297公釐) 3ϋ69〇8 8 888 ABCD 六、申請專利範圍 其中L 1係親核性取代之雜去基,與下式VI之羰羥基亞胺 反應 0 = C ( R 4 ) - C ( R 3 ) = Η Ο Η V 11 K產生式Vffl之化合物 〇-C ( R< ) -c ( ) -NOCH(R2), viii 然後將Vi a) 先與羥基胺或其鹽,接著用式vi化合物 R5 - L2 V [ (其中L2係親核性可取代之離去基)進行反應或 b ) 用下式[X a或1 X b之羥基胺或羥基銨鹽 r5-onh: IXa Rs-onh3® ςΡ IXb (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局貝工消費合作社印製 8 . 其中Q ® 侮酸之陰離子, W姦生根撺由請專利範圍第1項之式[化合物σ 一種對杭動物害蟲之组合物,包含常用添加物及有效最 之根棟由請專利範圍第丨項之茏乙酸衍生物或其鹽類, 或式I化合物中R 1及R 3為甲基、R 4為2 , 4 - i: u - « Η 3、m -F. 本紙張尺度適用中國國家揉準(CNS ) A4规格(210X 297公釐) 306908 8 8 8 8 ABCD 六、申請專利範圍 10 11 12 13 為〇 a r 3為氣者3 一種對杭有害真菌之姐 之根據申請專利範園第 稂楝申請專利範圍第8 類節肢動物或線蟲為主 一種控制動物害蟲之方 利範圍第1項之茏乙酸 中R1及R5為甲基、R4為 處理害蟲,其環境或欲 表面,材®或空間。 一棰控制有害真_之方 利範圍第]遺之笼乙醋 ,其環境或欲保持不存 誓或空間: 一種式Vill之化合物: 合物,包含常用添加物及有效量 1項之笼乙_衍生物或其鹽類。 項之組合物,可控制昆蟲,蜘蛛 之動物害蟲。 法,包栝用有效量之根撺申請專 衍生物或其鹽類,或式I化合物 2 , 4 - C U - C s Η 3、m 為 0 且 R 3 為氫者 保持不存有該動物害蟲之植物· 法*包栝用有效量之根據申請專 衍生物或其鹽_,處理有害真菌 有該有害* ll之植物,表面,材 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央揉準局貝工消費合作社印製 0-C(R4)~C(R3)-HOCH(R2)r VIII 其由 X Ν η (: Η :, > C Η 0 c H a 0¾ C H C Η R 1 偽氧或Γ i - C Λ -烷基; 6 - 本紙張尺度適用中國國家標準(CNS ) A4规格(210X297公釐) ^〇βθ〇8 A8 B8 C8 D8六、申請專利範圍 R2 係鹵素,(:ι-ί:Λ -烷基或Ci-G -烷氧基; m 係0或Ί ; R 3 係篋,羥基,胺基,鹵素,C , - C 4 -烷基,C 1 - C 4 -烷 氯基,C , - C Λ -垸碲基,c t - C 4 -烷胺基或二-C X - C 4 -烷胺基; R 4 像氰基,鹵素,C ! - C β -烷基,C ! - C β -垸氧基, “ -C « -烯氣基,有可能這费基團之馋基係部份或完 全_化或帶有1至3個''卞列基:笼基; mm. 笼基· 5員雑芳基或吡啶基,有可能環狀基係部份 南化戎帶有1至3個下列基:硝基,烷基, - C β -烷氬基,二-C 1 - C « -烷胺基,笼基: 1 4 .枵撺申諳專利範圍第1 3項之式VI化合物,其係當作中間 夠3 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標隼局員工消费合作社印製 本紙張尺度逋用中國國家榇準(CNS ) Α4洗格(210Χ297公釐)
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| CN1152007C (zh) † | 1994-01-05 | 2004-06-02 | 诺瓦提斯公司 | 杀虫剂 |
| US5874467A (en) * | 1994-02-04 | 1999-02-23 | Bayer; Herbert | Phenylacetic acid derivatives and use as fungicides |
| CH689228A5 (de) * | 1994-10-07 | 1998-12-31 | Novartis Ag | Oximether, sowie diese enthaltende Pflanzenschutzmittel. |
| WO1996016026A1 (en) * | 1994-11-17 | 1996-05-30 | Novartis Ag | O-benzyl oxime ether derivatives and their use as pesticides |
| PT820435E (pt) * | 1995-04-08 | 2001-10-30 | Basf Ag | Processo para a preparacao de isomeros essencialmente puros de alfa-bis-oximas |
| TR199701672T1 (xx) * | 1995-06-22 | 1998-05-21 | Novartis Ag | Zararl� bitki ve hayvanlar� �ld�r�c� trioksimino heterosiklik bile�ikler. |
| AU708591B2 (en) * | 1995-06-27 | 1999-08-05 | Bayer Aktiengesellschaft | O-benzyl oxime ether derivatives and their use in crop protection compositions |
| JPH11508569A (ja) * | 1995-07-04 | 1999-07-27 | ノバルティス アクチェンゲゼルシャフト | トリアゾリン及びイソキサゾリンビス−オキシム誘導体並びに殺虫剤としてのその用途 |
| CN1192200A (zh) * | 1995-07-27 | 1998-09-02 | 巴斯福股份公司 | 苯乙酸衍生物.制备它们的方法和中间体,以及它们用作杀害虫的组合物和杀真菌剂 |
| DE19528651A1 (de) * | 1995-08-04 | 1997-02-06 | Basf Ag | Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
| IL123421A0 (en) * | 1995-09-18 | 1998-09-24 | Basf Ag | Phenylacetic acids their preparation and compositions comprising them |
| AR004012A1 (es) | 1995-10-10 | 1998-09-30 | Basf Ag | Derivados de acido fenilacetico, procedimientos para su obtencion, su uso para preparar composiciones para combatir animales u hongos nocivos, lascomposiciones asi obtenidas y los procedimientos de aplicacion de dichas composiciones. |
| DE19537750A1 (de) * | 1995-10-10 | 1997-04-17 | Basf Ag | Oxiaminooximether, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
| DE19539324A1 (de) * | 1995-10-23 | 1997-04-24 | Basf Ag | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
| DE19540361A1 (de) | 1995-10-30 | 1997-05-07 | Basf Ag | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
| EP0873313B1 (de) * | 1995-11-02 | 2000-03-15 | Basf Aktiengesellschaft | Pyridylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung |
| DE19540989A1 (de) * | 1995-11-03 | 1997-05-07 | Basf Ag | Pyridylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
| KR19990071886A (ko) | 1995-12-07 | 1999-09-27 | 더블류. 하링, 지. 보이롤 | 농약의 제조방법 |
| EP0865424B1 (en) * | 1995-12-07 | 2002-09-18 | Bayer Aktiengesellschaft | Pesticides |
| EP0782982B1 (de) | 1996-01-03 | 2000-05-17 | Novartis AG | Verfahren zur Herstellung o-Chlor-Methyl-Phenylglyoxylsäure-Derivaten |
| NZ331122A (en) * | 1996-04-26 | 2000-06-23 | Basf Ag | Fungicide mixtures containing a carbamate derivative and/or an oxime ether derivative and organotin compound |
| WO1997040673A1 (de) * | 1996-04-26 | 1997-11-06 | Basf Aktiengesellschaft | Fungizide mischungen |
| EP0900020B1 (de) * | 1996-04-26 | 2002-06-26 | Basf Aktiengesellschaft | Fungizide mischungen |
| DK0900012T3 (da) * | 1996-04-26 | 2002-07-01 | Basf Ag | Fungicide blandinger |
| SK138698A3 (en) * | 1996-04-26 | 1999-04-13 | Basf Ag | Fungicidal mixtures |
| EA001105B1 (ru) * | 1996-04-26 | 2000-10-30 | Басф Акциенгезельшафт | Фунгицидные смеси |
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-
1995
- 1995-01-03 US US08/682,760 patent/US5874467A/en not_active Expired - Fee Related
- 1995-01-03 JP JP52033595A patent/JP3307396B2/ja not_active Expired - Fee Related
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- 1995-01-03 BR BR9506719A patent/BR9506719A/pt not_active IP Right Cessation
- 1995-01-03 HU HU9602153A patent/HU221460B/hu not_active IP Right Cessation
- 1995-01-03 CN CN95191969A patent/CN1104410C/zh not_active Expired - Fee Related
- 1995-01-03 SK SK1024-96A patent/SK282153B6/sk unknown
- 1995-01-03 CZ CZ19962314A patent/CZ293803B6/cs not_active IP Right Cessation
- 1995-01-03 AU AU14546/95A patent/AU691863B2/en not_active Ceased
- 1995-01-03 KR KR1019960704234A patent/KR100371884B1/ko not_active Expired - Fee Related
- 1995-01-03 PL PL95315773A patent/PL179077B1/pl not_active IP Right Cessation
- 1995-01-03 RU RU96118118/04A patent/RU2165411C2/ru not_active IP Right Cessation
- 1995-01-03 EP EP95906288A patent/EP0738259B1/de not_active Expired - Lifetime
- 1995-01-03 NZ NZ278587A patent/NZ278587A/en unknown
- 1995-01-03 WO PCT/EP1995/000013 patent/WO1995021153A1/de not_active Ceased
- 1995-01-03 ES ES95906288T patent/ES2150550T3/es not_active Expired - Lifetime
- 1995-01-03 CA CA002182529A patent/CA2182529A1/en not_active Abandoned
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- 1995-01-03 DK DK95906288T patent/DK0738259T3/da active
- 1995-01-03 PT PT95906288T patent/PT738259E/pt unknown
- 1995-01-03 EP EP99107871A patent/EP0945431A3/de not_active Withdrawn
- 1995-01-27 IL IL13765995A patent/IL137659A/xx unknown
- 1995-01-27 IL IL11246895A patent/IL112468A/xx unknown
- 1995-02-03 ZA ZA95858A patent/ZA95858B/xx unknown
- 1995-02-07 TW TW084100978A patent/TW306908B/zh active
- 1995-03-01 UA UA96083372A patent/UA56987C2/uk unknown
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1998
- 1998-03-25 AU AU59513/98A patent/AU704472B2/en not_active Ceased
- 1998-06-16 US US09/097,863 patent/US6066756A/en not_active Expired - Fee Related
- 1998-06-16 US US09/097,862 patent/US5990339A/en not_active Expired - Fee Related
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