TW201130418A - Ester compound and use thereof - Google Patents
Ester compound and use thereof Download PDFInfo
- Publication number
- TW201130418A TW201130418A TW100105598A TW100105598A TW201130418A TW 201130418 A TW201130418 A TW 201130418A TW 100105598 A TW100105598 A TW 100105598A TW 100105598 A TW100105598 A TW 100105598A TW 201130418 A TW201130418 A TW 201130418A
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- Taiwan
- Prior art keywords
- compound
- formula
- configuration
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- reaction
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- -1 Ester compound Chemical class 0.000 title claims abstract description 113
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims description 169
- 239000000203 mixture Substances 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 238000004519 manufacturing process Methods 0.000 claims description 47
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- 238000000034 method Methods 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 34
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- 239000002904 solvent Substances 0.000 claims description 26
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
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- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
- A01M1/00—Stationary means for catching or killing insects
- A01M1/20—Poisoning, narcotising, or burning insects
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Description
201130418 六、發明說明: 【發明所屬之技術領域】 本發明係關於一種酯化合物及其用途。 【先前技術】 迄今為止已經合成各種化合物以用於防治害蟲。舉例 而言,於JP-A-60-16962以及JP-A-57-158765中所描述之 某些醋化合物。 【發明内容】 本發明之目的係提供一種具有良好的害蟲防治效果 之新穎化合物。 本發明之發明人精心研究後發現如下述式(1)所示之 酯化合物具有良好的害蟲防治效果,遂完成本發明。 亦即,本發明係關於下述之發明: [1]一種式(1)所示之酯化合物(後文中,將此化合物稱為本 發明化合物):
其中R1表.不Ci_C4烧基; [2] 如[1]所述之酯化合物,其中,於式(1)中,在該環丙 烷環之1-位置的取代基和在該環丙烷環之3-位置的取代 基之相對構型為反式構型; [3] 如[1]所述之酯化合物,其中,於式(1)中,該環丙烷 3 322813 201130418 環之1-位置的絕對構型為R構型; [4] 如[1]所述之酯化合物,其中,於式(1)中,該環丙烷 環之1-位置的絕對構型為R構型,以及在該環丙烷環之卜 位置的取代基與在該環丙烧環之3-位置的取代基之相對 構型為反式構型; [5] 如[1]至[4]中任一項所述之酯化合物,其中,於式(1) 中,在該環丙烷環之3-位置的取代基之雙鍵為E構型或E 構型與Z構型之混合物,且E構型之比例為5〇%或以上; [6] 如[1]至[4]中任一項所述之酯化合物,其中,於式(1) 中,在該環丙院環之3-位置的取代基之雙鍵為£構型; [7] 如[1]至[4]中任一項所述之酯化合物,其中,於式(1) 中,R1為甲基; [8] 如[1]至[4]中任一項所述之酯化合物,其中,於式 中,R1為乙基; [9] 如[5]所述之酯化合物,其中,於式(1)中,Ri為曱基; [10] 如[5]所述之酯化合物,其中,於式(1)中,^為乙基; [11] 如[6]所述之酯化合物,其中,於式(1)中,Ri為甲基; [12] 如[6]所述之酯化合物,其中,於式(1)中,Ri為乙基; [13 ] —種害蟲防治劑,係包含[1 ]至[12 ]中任一項所述之 酯化合物及惰性載劑; [H] —種防治害蟲之方法,係包含將有效量之[丨]至[12] 中任一項所述之酯化合物施加於害蟲或害蟲棲息處之步驟; [15] —種防治害蟲之方法,係包含將有效量之[丨]至[12] 中任一項所述之酯化合物施加於蟑螂或蟑螂棲息處之步驟; 322813 4 201130418 [16] 如[15]所述之防治害蟲之方法,其中,該蟑螂為美洲 蟑螂(Periplaneta Americana); [17] 如[15]所述之防治害蟲之方法,其中,該蟑螂為德國 緯螂(Blattella germanica); [18] —種防治害蟲之方法,係包含將有效量之[1]至[12] 中任一項所述之酯化合物喷灑於蟑螂或蟑螂棲息處之步 驟; [19] 如[18]所述之防治害蟲之方法,其中,該蟑螂為美洲 緯螂; [20] 如[18]所述之防治害蟲之方法,其中,該蟑螂為德國 _螂。 本發明之化合物具有良好的害蟲防治效果,因而適用 於作為害蟲防治劑之活性成分。 於本發明之化合物中,有由位於環丙烷環之1-位置及 3-位置的兩個不對稱碳原子而得之異構物,以及由存在於 環丙烧環之3-位置的取代基中之雙鍵衍生而得的異構物。 各個具有害蟲防治活性之異構物或該等具有害蟲防治活性 之異構物的任何比例之混合物皆包含於本發明中。
R1表示之Ci-C〗烷基之實例包括曱基、乙基、丙基、丁 基及異丙基。 5 322813 201130418 一種下列化合物。 取代基與在環丙坑 其中,在環丙烧環之卜位置的 式構型; 仇置的取代基之相對構型為反 -種式(1)所示之化合物 對構型為β構型; 、中,環丙烷環之1-位置的絕 一種式(1)所示之化合物,
對構型為R構型,以及其中,環丙燒環之卜位置的絕 環丙烧環之3>位置的取=燒環之卜位置的取代基與在 -種式⑴所示之化a物相對構型為反式構型; 取代基之雙鍵為£構型或在環城環之3-位置的 構型之比例為5()%或以上;型與Z構型之混合物,且E 一種式⑴所示之化合物 取代基與在環内燒環、中,在環丙燒環之卜位置的 式構型,在環㈣環之^置的取代基之相對構型為反 E構型與Z構型之混合物,4置的取代基之雙鍵為E構型或 -種式⑴所示之化合物,^構,比例為50%或以上; 對構型為R構型,在環,壤丙燒環之卜位置的絕 E構型或E構型與z構型:=—位置的取代基之雙鍵為 或以上; 〇物’且E構型之比例為δ0% -種式⑴所示之化合物 對構型W構型,在環丙貌環中之之卜位置的絕 烧環之3-位置的取代基之相對構型為==: 環之3—位置的取代基之雙物構型或E構型與t構: 322813 6 201130418 混合物,且E構型之比例為_或以上; 一種式⑴所示之化合物,其中,在環丙歸之 取代基之雙鍵為£構型; 置的 一種式⑴所示之化合物,其中,在環丙烧環之卜位置的 ^代基與在%咕環之3_位置的取代基之相對構型為反、 '構型’以及在環狀環之3_位置的取代基之雙鍵為 一種式⑴所示之化合物,其中,環丙烧環之卜位置 對構型為R構型,以及在環㈣環之3_位置 之 鍵為E構型; 〜丞之雙 種式(1)所示之化合物,其中,環丙院環之卜位置的 對,型為R構型’在環㈣環之卜位置的取代基與在環内 院%3-位置的取代基之相對構型為反式構型,以及在環 丙烧環之3-位置的取代基之雙鍵為請型; 衣 一種式(1)所示之化合物,其中,在環⑽環之卜位置的 取代基與在環丙院環之3_位置的取代基之相對構型為反 式構型’以及R1為甲基; 一種式⑴所示之化合物,其中,環丙炫環之1-位置的絕 對構型為R構型’以及Ri為甲基; Γ種式⑴所示之化合物,其中,環丙烧環之1-位置的絕 對,型為R構型’在環丙貌環之卜位置的取代基與在環丙 院環之3-位置的取代基之相對構型為反式構型, 為甲基; 一種式(1)所示之化合物 其中’在環丙烷環之3-位置的 322813 7 201130418 取代基之雙鍵為E構型或E構型與 型之比例為咖或以上,以及R1為甲^之混合物,請 := 所示之化合物,其中’在環W環之1-位置的 式構丙燒環之3一位置的取代基之相對構型為反 ί構刑斑7%丙烷環之3_位置的取代基之雙鍵為E構型或 及R1為甲A構型之混合物,請型之比例為5G%或以上,以 斛⑴所不之化合物’其中’環丙烷環之卜位置的絕 型為R構型,在環丙烷環之位置的取代基之雙鍵為 舞里或E構型與2構型之混合物,以籌型之比例為遞或 以上’以及R1為曱基; H 所示之化合物,其中,環丙院環之卜位置的絕 尸構型’在環丙烧環之卜位置的取代基與在環丙 二/立置的取代基之相對構型為反式構型,在環丙烷 的取代基之雙鍵為E構型或E構型與Z構型之 δ 構型之比例為5〇%或以上,以及Rl -種式⑴所示之化人 及甲基’ ㈣物其中,在環丙院環之3—位置的 戈基之雙鍵為Ε構型,以及R1為甲基; 合:3’其中,在糧環之卜位置的 < 、元衣之3-位置的取代基之相對構型為反 ^及丙烧環之3~位置的取代基之雙鍵為Ε構型, SSI所示之化合物,其中,環丙烧環之卜位置的絕 構型’在環丙貌環之3_位置的取代基之雙鍵為 322813 8 201130418 E構型,以及Ri為甲基; 對所不之化合物,其中’環丙烷環之1_位置的絕 ρ ·、、、_,在環㈣環之卜位置的取代基與在環两 位置的取代基之相對構型為反式構型,在環丙娟 2 '位置的取代基之雙鍵為E構型,以及Ri為甲基; :=二示之化合物,其中’在環丙燒環之卜位置的 =與在核丙燒環之3_位置的取代基之相對構型為反 式構型,以及R1為乙基; 對構^ A 1 所不之化合物’其中’環丙燒環之卜位置的絕 對魅為R構型,以及R1為乙基; 示之化合物,其中,環㈣環之卜位置的絕 炫=構型,在環丙烧環之卜位置的取代基與在環丙 置的取代基之相對構型為反式構型,以及ri
Sit:之化合物,其中,在環丙烧環之3-位置的 型或E構型與2構型之混合物,E構 i之比例為50%或以上,以及乙基; 再 之化合物’其中,在環:環之卜位置的 E槿❹Ϊ ㈣代基之賴為E構型或 ;構型之混合物’Ε構型〜例一上,: 種式(1)所示之化合物,其中, 322813 9 201130418 E構型或E構型與Z構型之混合物,E構型之比例為50%或 以上’以及R1為乙基; 一種式(1)所示之化合物,其中,環丙烷環之卜位置的絕 對構型為尺㈣’在環丙院環之1-位置的取代基與在環丙 烷%之3-位置的取代基之相對構型為反式構型,在環丙烷 環之3-位置的取代基之雙鍵為E構型或E構型與z構型之 混合物,以冓型之比例為50%或以上,以及R1為乙基; 種式(1)所不之化合物,其中,在環丙烧環之 3-位置的 取代基之雙鍵為E構型,以及^為乙基; 二之:Γ勿’其中,在環_之1,置的 六:’元環之3'位置的取代基之相對構型為反 ⑽環之3'位置的取代基之雙鍵為£構型, Μ及Κ為乙基; 一種式(1)所示之化合物,Α 對構型為《構型,在科^=環丙㈣之卜位置的絕 Ε構型,以及Ri為乙基;*之3_位置的取代基之雙鍵名 一種式(1)所示之化合物, 對構型為β構型,在严兩^、中,環丙烷環之1_位置的絕 烧環之3-位置的取環之卜位置的取代基與在環丙 環之3-位置的取代基^目對構型為反式構型’在環丙烷 -種式(1)所示之化合物,鍵為Ε構型,以及R1為乙基; 取代基與在環丙烷環,之3其中,在環丙烷環之丨_位置的 式構型; 、、位置的取代基之相對構型為順 一種式(1)所示之化合物, 其中’環丙烷環之1-位置的絕 322813 10 201130418 =構里為R構型’以及在環丙烧環之卜位置的取代基與在 、元衣之3位置的取代基之相對構型為順式構型; -種式⑴所示之化合物,其中,在環丙炫環之卜位置的 取代基與在核丙烧環之3 _位置的取代基之相對構型為順 式構型,在環狀環之3_位置的取代基之雙鍵為£構型; 以及 種式(1)所示之化合物,其中,環丙烷環之卜位 對,型為R構型,在環丙院環之卜位置的取代基與在環丙 烷%<之3〜位置的取代基之相對構型為順式構型,以及2 丙烧環之3-位置的取代基之雙鍵為E構型。 【實施方式】 以下將說明本發明化合物之製造方法。 本發明化合物可例如藉由以下方法製造。 (製造方法^ 該方法為將式(2)所示之醇化合物:
〃式(3)所示之羧醵化合物或其反應性衍生物反應 HA ch3
HO
^CH=C(CN)SR1 (3) ο 其中R1表示與上述相同之意思。 反應性衍生物之實例包括式(3)所示羧酸化合物之酿 322813 11 201130418 鹵(acid halide)、式(3)所示羧酸化合物之酸軒式(3) 所示叛酸化合物之醋等。醯^之實例包括醯氣化合1及酿 溴化合物,並且酯之實例包括甲基酯、乙基酯等。 此反應通常於縮合劑或鹼存在下在溶劑中進行。 此反應所使用之縮合劑之實例包括二環己基碳二亞 胺及1-乙基-3-(3-二曱基胺基丙基)碳二亞胺鹽酸鹽。 此反應所使用之鹼之實例包括有機鹼類,諸如三乙胺、 °比°定、N,N-二乙基苯胺、4-二曱基胺基η比咬及二異丙基乙 基胺。 此反應所使用之溶劑之實例包括烴類諸如苯、甲苯及 己烷;醚類諸如二乙醚及四氫呋喃;齒化烴類諸如氯仿、 一氯曱烧、1,2_二氯乙烧及氣苯;此等溶劑之混合物等β 此反應之反應時間通常在5分鐘至72小時之範圍内。 此反應之反應溫度通常在-20°C至1〇〇。〇之範圍内(由 - 2 0 C至溶劑之彿點’若所使用之溶劑的彿點低於1 〇 〇), 以及較佳為-5°C至100°C (由-5°C至溶劑之沸點,若所使用 之溶劑的沸點低於100°C)。 在此反應中,式(2)所示醇化合物相對於式(3)所示羧 酸化合物或其反應性衍生物所使用之莫耳比例可任意設 定,並且較佳為等莫耳比例或接近等莫耳比例。 以1莫耳(mol)之式(2)所示醇化合物為基準計,縮合 劑或鹼通常可在0. 25 mol至過量之範圍内以任意比例使 用,並且較佳為1. 0 mol至2 mol。此等縮合劑或驗係依 據式(3)所示叛酸化合物或其反應性衍生物之種類而適當 12 322813 201130418 選擇。 在反應完成後,反應混合物通常會進行後續處理,舉 例而言,將反應混合物過濾,接著將濾液濃縮,或者將反 應混合物倒入水中並將所獲得之溶液以有機溶劑萃取後再 濃縮,如此可獲得本發明之化合物。所獲得之本發明化合 物可藉由例如層析法之操作而純化。 (製造方法2) 於本發明之化合物中,式(1 -1)所示之化合物(其中, 在環丙烷環之1-位置的取代基與在環丙烷環之3-位置的 取代基之相對構型為順式構型)可藉由下列所示之方法製 造。 式(H)
CH=C(CN)SR 其中R1表示與上述相同之意思。 該方法為將式(45)所示内酯化合物: h3c ch3
o CN 其中R1表示與上述相同之意思, 與式(5)所示化合物於驗存在下反應: 13 322813 201130418
此反應通常在鹼存在下於溶劑中進行。此反應所使用 之溶劑之實例包括嗣類諸如丙酮、甲基乙基酮及甲基異丁 基酮;醚類諸如四氫呋喃;鹵化烴類諸如氣仿、二氯曱烷、 1,2-一氯乙烧及氯求;酿胺類諸如N,N-二曱基曱酿胺;亞 砜類諸如二曱基亞砜;此等溶劑之混合物等。 此反應所使用之鹼之實例包括碳酸鹽類諸如碳酸鈉、 碳酸卸及碳酸絶。 此反應之反應時間通常在5分鐘至72小時之範圍内。 此反應之反應溫度通常在-20°C至ΙΟΟΐ之範圍内(由 -2(TC至溶劑之沸點’若所使用之溶劑的沸點低於), 並且較佳為-5°C至lOOt:(由-5Ϊ至溶劑之沸點,若所使用 之溶劑的沸點低於100°C)。 在此反應中,式(4)所示内酯化合物相對於式所示 化合物所使用之莫耳比例可任意設定,並且較佳為等莫耳 比例或接近等莫耳比例。 以1 mol之式(4)所示内酯化合物為基準計,鹼通常 可在0.25 mol至過量之範圍内以任意比例使用,並且較佳 為 0. 5 mol 至 2 mol。 在反應完成後,反應混合物通常會進行後續處理,舉 例而言,將反應混合物過濾,接著將濾液濃縮,或者將反 322813 14 201130418 應混合物倒入水中並將所獲得之溶液以有機 濃縮,因此可單離式叫)所示化合物。式(⑼所示= 物可藉由諸如層析法之操作而純化。 ° 式⑵所不醇化合物係JP-A-57-158765中所描述 合物。 化 本發明之中間產物可藉由例如下述方法製造。 (參考製造方法1) 在式(3)所示之幾酸化合物中,式(3_η所示之竣酸化 合物其中’在環丙燒環之卜位置的取代基與在環㈣環之 3-位置的取代基之相對構型為反式構型者可藉由例如 方法製造。 (第1步驟) 將式(6)所示之卡隆酸(caronaldehyde)酯衍生物:
其中R2表示G-C5烷基, 與式(7)所示之腈化合物於驗存在下反應: R1S、^CN (7) 其中R1表示與上述相同之意思, 因而可製得式(8)所示之化合物: 15 322813 201130418
其中R1及R2表示與上述相同之意思。 (第2步驟) 使式(8)所示化合物在鹼存在下進行水解反應,而可 製得式(3-1)所示之羧酸化合物:
其中R1表示與上述相同之意思。 第1步驟之反應通常藉由下述方式進行:以1 mol之 式(6)所示之卡隆酿酯衍生物為基準計,使用1.〇至1.5 mol之比例的式(7)所示之腈化合物及1至1〇 mol之比例 的鹼,使此等物質於極性溶劑中在0°C至80°C(較佳為〇°C 至30°C )反應。此反應所使用之驗之實例包括碳酸鹽諸如 碳酸钟及碳酸納;及驗金屬化合物諸如氫化納。此反應所 使用之極性溶劑之實例包括醯胺類諸如N,N-二甲基曱醯 胺;及亞颯類諸如二曱基亞砜。 在反應完成後,反應混合物通常會進行後續處理,舉 例而言,將反應混合物加入水中並將所獲得之溶液以有機 溶劑萃取’隨後再將有機層脫水並濃縮,而可獲得式(8) 322813 201130418 所示之化合物。 第2步驟之反應通常藉由下述方式進行:以1 mol之 式(8)所示化合物為基準計,使用1至10 mo 1之比例的驗, 於溶劑中在0°C至80°C(較佳為0°C至30°C)反應。此反應 所使用之鹼之實例包括氫氧化物諸如氫氧化鉀或氫氧化 鈉。此反應所使用之溶劑之實例通常為水與醚(諸如四氫0夫 喃)之混合物或水與醇(諸如甲醇)之混合物。 在反應完成後,將反應混合物進行後續處理,舉例而 言,將反應混合物酸化,隨後以有機溶劑萃取,接著再將 有機層脫水並濃縮,而可獲得式(3-1)所示之羧酸化合物。 式(6)所示之卡隆搭酯衍生物係Tetrahedron 45, 3039-3052(1989)中所描述之化合物。 (參考製造方法2) 式(4)所示内酯化合物:
其中R1表示與上述相同之意思, 可藉由例如將式(9)所示之内鱗醇(1 acto 1)衍生物:
17 322813 201130418 與式(7)所示之腈化合物: (7) 其中R1表示與上述相同之意思, 在鹼存在下反應而製造。 此反應通常藉由下述方式進行:以1 mol之式(9)所 示内驗醇衍生物為基準計,使用1. 0至1 · 5 mo 1之比例的 式(7)所示之腈化合物以及1至10 mol之比例的驗,於極 性溶劑中在0°C至80°C(較佳為〇°C至50°C)反應。此反應 所使用之鹼之實例包括碳酸鹽諸如碳酸鉀及碳酸鈉;及鹼 金屬化合物諸如氫化納。此反應所使用之極性溶劑之實例 包括醯胺類諸如N,N-二曱基曱醯胺;及亞砜類諸如二曱基 亞硬。 在反應完成後,將反應混合物進行後續處理,舉例而 言,將反應混合物酸化並以有機溶劑萃取,隨後再將有機 層脫水並濃縮,而可單離式(4)所示之内酯化合物。 式(9)所示之内鱗醇衍生物係Synthet i c Communications, 17,1089-1094(1987)中所描述之化合 物。 本發明化合物對其具有防治效果之害蟲之實例包括 有害的節肢類害蟲諸如有害的昆蟲類及有害的蟎類 (acarines),且更具體係下列害蟲類。 半翅目(Hemiptera):飛兹(planthoppers)諸如斑飛 蝨(Laodelphax striatellus)、褐飛蝨(Nilaparvata 18 322813 201130418 lugens)及白背飛益(Sogatella furcifera);葉蟬 (leafhoppers)諸如偽黑尾葉蟬(Nephotettix cincticeps) 及二點黑尾葉禪(Nephotettix virescenes);財蟲(aphids) 諸如棉财(Aphis gossypii)及桃財(Myzus persicae);盲 缚(plant bugs)諸如稻綠椿象(Nezara antennata)、點蜂 緣椿象(Riptortus clavatus)、二星蝽(Eysarcoris lewisi)、白星蝽(Eysarcoris parvus)、小珀蜂象(Plautia s tali)及大綠椿(Halyomorpha mista);粉益(white flies) 諸如溫室粉兹(Trialeurodes vaporariorum)、煙草粉蟲 (Bemisia tabaci)及銀葉粉兹(Bemisia argentifolii); 介殼蟲(scales)諸如紅圓介殼蟲(Aonidiella aurantii)、 梨圓介殼蟲(Comstockaspis perniciosa)、桔矢尖介殼蟲 (Unaspiscitri)、紅蠛介殼蟲(Ceroplastesrubens)及吹 棉介殼蟲(Icerya purchasi);軍配蟲(lace bugs);床蝨 (bed bugs)諸如溫帶臭蟲(Cimex lectularius)、木兹 (Jumping plantlice)等; 鱗翅目(Lepidoptera):填蛾科(Pyralidae)諸如二化 堵(Chilo suppressalis)、稻縱捲葉野螟蛾 (Cnaphalocrocis medinalis)、棉卷葉野螟(Notarcha derogata)及印度榖粉螟蛾(Plodia interpunctella)、斜 紋夜蛾(Spodoptera litura)、東方黏蟲(Pseudaletia separata);夜蛾科(Noctuidae)諸如粉纹夜蛾 (Trichoplusia spp.)、棉鈴蟲屬(Heliothis spp.)及瘤蛾 屬(Earias spp.);粉蝶科(Pieridae)諸如紋白蝶(Pieris 19 322813 201130418 rapae);捲葉蛾科(Tortricidae)諸如小捲葉蛾屬 (Adoxopheys spp.)、梨小食心蟲(Grapholita molesta)、 小角紋捲葉蛾(Adoxophyes orana fasciata)及蘋果蠹蛾 (Cydia pomonella);果姓蛾科(Carposinidae)諸如桃小食 心蟲(Carposina niponensis);潛蛾科(Lyoneti idae)諸如 潛蛾屬(Lyonetia spp.);毒蛾科(Lymantriidae)諸如毒蛾 (Lymantria spp.);毒蛾科(Lymantriidae)諸如黃毒蛾屬 (Euproctis spp.);巢蛾科(Yponameutidae)諸如小菜蛾 (Plutella xylostella);麥蛾科(Gelechiidae)諸如棉紅 鈴蟲(Pectinophora gossypiella);燈蛾科(Arctiidae) 諸如美國白娥(Hyphantria cunea);谷蛾科(Tineidae)諸 如幕衣蛾(Tinea translucens)以及衣蛾(Tineola bisselliella)等; 雙翅目(Diptera):庫蚊屬(Culex spp.)諸如淡色庫 蚊(Culex pipiens pallens)及三斑家蚊(Culex t r i t aen i orhynchus )及致倦庫蚊(Culex quinquefasciatus);黑斑蚊屬(Aedes spp.)諸如埃及斑蚊 (Aedesaegypti)及白線斑蚊(Aedesalbopictus);瘧蚊屬 (Anopheles spp.)諸如中華癔蚊(Anopheles sinensis)及 甘比亞瘧蚊(Anopheles gambiae);搖蚊科 (Chironomidae);蠅科(Muscidae)諸如家蠅(Musca domestica)及廄腐蠅(Muscina stabulans);麗蠅科 (Calliphoridae);肉繩科(Sarcophagidae);小家繩 (little housefly);花蠅科(Anthomyiidae)諸如灰地種娜 20 322813 201130418 (Delia platura)及蔥罐(Delia antique);果實罐科 (Tephritidae);果蠅科(Drosophilidae);蚤蠅科 (Phoridae)諸如東亞異蚤题(Megaselia spiracularis); 毛蠓(Clogmia albipunctata);蛾蚋科(Psychodidae); 蚋科(Simuliidae) ; it科(Tabanidae);刺繩科 (Stomoxyidae);潛繩科(Agromyzidae)等; 鞘翅目(Coleoptera):葉曱屬(Diabrotica spp.)諸 如玉米根葉曱(Diabrotica virgifera virgifera)及十一 星瓜葉曱(Diabrotica undecimpunctata howardi);金龜 子科(Scarabae i dae)諸如金銅金龜(Anoma 1 a cuprea)及榛 姬金龜(Anomala rufocuprea);象鼻蟲科(Curculionidae) 諸如玉米象曱(Sitophi lus zeamais)、稻水象曱 (Lissorhoptrus oryzophilus)及綠豆象曱 (Callosobruchuys chienensis);擬步甲科 (Tenebrionidae)諸如黃粉蟲(Tenebrio molitor)及赤擬 榖盜(Tribolium castaneum);金花蟲科(Chrysomelidae) 諸如稻負泥蟲(Oulema oryzae)、黃守瓜(Aulacophora femoralis)、黃條葉蚤(Phyllotreta striolata)及科羅拉 多金花蟲(Leptinotarsa decemlineata);鰹節蟲科 (Dermestidae)諸如白腹皮蠹(Dermestes maculates);竊 蠹科(Anobiidae);食植瓢蟲屬(Epi lachna spp.)諸如茄二 十八星瓢蟲(Epilachna vigintioctopunctata);扁螽蟲科 (Lyctidae);長蠢蟲科(Bostrychidae);蛛蠹科 (Ptinidae);天牛科(Cerambycidae);蟻型隱翅蟲 21 322813 201130418 (Paederus fuscipes)等; 蜚蠊目(Blattodea):德國斐蠊(Blattel la germanica)、黑胸大蠊(Periplaneta fuliginosa)、美洲 蜚蠊(Periplaneta americana)、棕色斐蠊(Periplaneta brunnea)、東方 S 嫌(Blatta orientalis)等; 纓翅目(Thysanoptera):瓜薊馬(Thrips palmi)、葱 薊馬(Thrips tabaci)、西方花薊馬(Frankliniella occidentalis)、黑腹薊馬(Frankliniella intonsa)等; 膜翅目(Hymenoptera):蟻科(Formicidae)諸如小黃 家蟻(Monomorium pharaosis)、絲光褐林蟻(Formica fusca japonica)、無毛凹臭犧(Ochetellus glaber)、雙針蠘 (Pristomyrmex pungens)、寬結大頭蟻(Pheidole noda) 及阿根廷蟻(Linepithema humile);長腳蜂(long-legged wasps)諸如二紋長腳蜂(Polistes chinensis antennalis)、家長腳蜂(Polistes jadwigae)及黃長腳蜂 (Polistes rothneyi);胡蜂科(Vespidae)諸如曰本大黃蜂 (Vespa mandarinia japonica)、黃胡蜂(Vespa simillima)、小胡蜂(Vespa analis insularis)、黃邊胡 蜂(Vespa crabro flavofasciata)及黑尾虎頭蜂(Vespa ducalis);腫腿蜂科(Bethylidae);藤蜂(Xyl〇copa);玳 瑁蜂科(Pompilidae);泥蜂科(Sphecoidae);紅切葉蜂 (mason wasp)等; 直翅目(Ori:hoptera):螻蛄(m〇ie crickets)、蚱猛 (grasshoppers)等; 22 322813 201130418 蚤目(Siphonaptera):猫蚤(Ctenocephalides felis)、犬蚤(Ctenocephalides canis)、人蚤(Pulex irritans)、印度鼠蚤(Xenopsylla cheopis)等; 益目(Anoplura):人體兹(Pediculus humanus corporis)、陰蟲(Phthirus pubis)、牛盘(Haematopinus eurysternus)、羊蝨(Dalmalinia ovis)等; 等翅目(Isoptera):散白蟻屬(Reticulitermes spp·) 諸如黃胸散白蟻(Reticulitermes speratus)、臺灣家白蟻 (Coptotermes formosanus)、黃肢散白蟻(Reticulitermes flavipes)、美國散白蠘(Reticulitermes hesperus)、南 方散白蟻(Reticulitermes virginicus)、黑脛散白蟻 (Reticulitermes tibialis)及金又散白蟻(Heterotermes aureus);楹白蟻屬(Incisitermes spp.)諸如小楹白蟻 (Incisitermes minor)以及古白蟻屬(Zootermopsis spp.) 諸如内華達古白蠘(Zootermopsis nevadensis)等; 蜱瞒目(Acarina):葉蜗科(Tetranychidae)諸如二斑 葉蟎(Tetranychus urticae)、神澤葉蟎(Tetranychus kanzawai)、柑桔全爪蜗(Panonychus citri)、榆全爪蜗 (Panonychusulmi)及小爪蟎屬(〇lig〇nychus spp.);癭蟎 科(Er i ophy i dae)諸如刺皮節蜱(Acu 1 ops pe 1 ekass i)及蘋 果斯氏刺癭蜗(Aculus schlechtendali);細蜗科 (Tarsonemidae)諸如茶黃蜗(Polyphagotarsonemus latus);擬葉蟎科(Tenuipalpidae);杜克葉蟎科 (Tuckerellidae);硬蜱科(ix〇didae)諸如長角血蜱 23 322813 201130418 (Haemaphysalis longicornis)、血蜱(Haemaphysalis flava)、美洲犬蜱(Dermacentor variabilis)、卵形硬碑 (Ixodes ovatus)、全溝硬蜱(Ixodes persulcatus)、狎硬 蜱(Ixodes scapularis)、微小牛蜱(Boophilus microplus)、美洲鈍眼蜱(Amblyomma americanum)及棕色 犬壁蝨(Rhipicephalus sanguineus);粉蜗科(Acaridae) 諸如腐食酷·蜗(Tyrophagus putrescentiae);皮刺螨科 (Dermanyssidae)諸如美洲塵瞒(Dermatophagoides farinae)、歐洲塵蜗(Dermatophagoides ptrenyssnus); 肉食瞒科(Chey let idae)諸如普通肉食蜗(Cheyletus eruditus)、馬六曱肉食蜗(Cheyletus malaccensis)及肉 食蜗(Cheyletus moorei);雞瞒(chicken mite)諸如柏氏 禽刺瞒(Ornithonyssus bacoti)、北方刺脂蜗 (Ornithonyssus sylviarum)及雞皮刺瞒(Dermanyssus gallinae);毛壁兹科(Trombiculidae)諸如紅纖恙蜗 (Leptotrombidium akamushi)等; 始口蛛目(Araneae):日本葉螯蛛(Japanese foliage spider)(彭妮紅螯蛛(Chiracanthium japonicum))、紅背 缺1蛛(紅色物蛛(Latrodectus hasseltii))等、橫帶人面虫知 蛛(Nephi la clavata)(長腳蛛科(Tetragnathidae))、八疲 塵蛛(Cyclosa octotuberculata)、聖安德魯十字物蛛 (St. Andrew’ s cross spider)(悅目金蛛(Argiope amoena))、横紋金蛛(Wasp spider)(橫紋金蛛(Argiope bruennichii))、圓蛛(Orb-weaving spider)(大腹園蛛 24 322813 201130418 (Araneusventricosus))、草蛛(grass spider)(森林漏斗 蛛(Agelena silvatica))、狼蛛(w〇if spider)(黑豹蛛 (Pardosa astrigera))、斷尾蜘蛛(dock spider)(黃褐狡 蛛(Dolomedes sulfurous))、黑猫跳蛛(Carrhotus xanthogramma)、家隅蛛(common house spider)(大姬蛛 (Achaearanea tepidariorura))、安定隙蛛(Coelotes insidiosus)、跳蛛(jumping spider)(繩虎 (Salticidae))、高腳換蛛(huntsman spicier)(白額高腳蛛 (Heteropoda Venatoria))等; 唇足綱(Chilopoda):蝶松諸如姑蜒(Thereuonema hilgendorfi)、少棘娱虫公(Scolopendrasubspinipes)、曰 本蜈虫公(Scolopendra subspinipes japonica)、背條紅蜈 讼(Scolopocryptops rubiginosus)、粗背石娱讼 (Bothropolys asperatus)等; 倍足綱(Diplopoda):馬陸(millipedes)諸如花園馬 陸(garden millipede)(雅麗酸馬陸(Oxidus gracilis))、 花園馬陸(紅色馬陸(Nedyopus tambanus))、巨型馬陸 (train millipede)(汽車馬陸(Parafontaria laminata))、 巨型馬陸(汽車馬陸(Parafontaria laminata armigera))、 東帶馬陸(Parafontaria acutidens)、條馬陸目 (Epanerchodus oriental is)等; 等足目(Isopoda):潮蟲(sow bugs)諸如多霜躐鼠婦 (Porcellionides pruinosus)(球鼠婦(Brandt))、鼠婦 (?01^6111〇30&661*1^1^61116);球潮蟲(卩111131^8)諸如 25 322813 201130418 普通鼠婦(common pill bug)(鼠婦(Armadillidium vulgare));海水魚風(sea louses)諸如海緯螂(wharf roach)(奇異海蟑螂(Ligia exotica))等; 腹足綱(Gastropoda):樹蛞蝓(tree slug)(黃螺 (Limax marginatus));黃蛞蝓(yell〇w siUg)(Limax flavus)等。 本發明之害蟲防治劑含有本發明之化合物及惰性載劑。 本發明之害蟲防治劑通常製成下述之製劑(f〇rmulati〇n)。 製劑之實例包括油溶液、可乳化濃縮物、可濕性粉末、可 流動性製劑(如水性懸浮液或水性乳劑)、微膠囊、粉劑、 顆粒、錠劑、喷霧劑、二氧化碳製劑、#蒸散製劑(如殺蟲 線圈(insecticidal coil)、電熱殺蟲片或液態吸收芯型熱 蒸散殺蟲劑)、壓電殺蟲製劑、熱煙燻劑(fum 如自 燃型煙義、化學反應型煙_❹孔μ板煙燦劑)、無 加熱蒸散製劑(如樹脂蒸散製劑、紙蒸散製劑、非織造織物 蒸散製劑、針織織物蒸散製劑或昇華錠劑)、喷霧製劑(如 煙霧製劑)、直接接觸製劑(如片狀賴製劑、帶狀接觸製 劑或網狀接觸製劑)、ULV製劑及毒辑。 製劑之形成方法包括下列方法。 ϋ L種係包括將本發明之化合物與固態載劑、液態 載劑、或毒舰合,然後魏 他製劑用之助劑,並且若必要時,進行進—面,古:诏及兵 (2) —種方法,係包括將本發明之化合物浸責 (impregnation)於不含活性成分之基底村=。 322813 26 201130418 (3)—種方法’係包括將本發明之化合物與基底材料混*合’ 然後再將此混合物進行成型製程。 依據製劑的形式’此等製劑通常含有〇.001至98重 量%之本發明化合物。 製劑中所使用之固態载劑之實例包括黏土(如高顏 土、矽藻土、膨土、文挾土(Fubasami clay)或酸性白黏土) 之細粉末或顆粒、合成之水合氧化矽、滑石、陶瓷、其他 無機礦物(如絹雲母、石英、硫、活性碳、碳酸鈣或水合石夕 石)及細粉末與粒狀物質諸如化學肥料(如硫酸銨、磷酸 銨、硝酸銨、氯化銨或尿素);在室溫為固體之物質(如 2,4,6-三異丙基-1,3,5-三嘿烧("(:1^〇乂8116)、萘、對-二氯 苯或樟腦、金剛合金(adamantine));以及毛敦、纖維、織 物、針織物、薄片、紙、紗線(thread)、發泡體(f〇am)、 多孔材料及多絲纖維,該多絲纖維係包含一種或更多選自 下列所組成群組之物質:羊毛、絲、棉、麻、木漿、合成 樹脂(如聚乙烯樹脂諸如低密度聚乙烯、直鏈低密度聚乙烯 及高密度聚乙烯;乙烯-乙烯酯共聚物諸如乙烯—乙酸乙烯 酯共聚物;乙烯-甲基丙烯酸酯共聚物諸如乙烯—曱基丙烯 酸甲酯共聚物及乙烯-甲基丙烯酸乙酯共聚物;乙烯-丙烯 酸酯共聚物諸如乙烯-丙烯酸甲酯共聚物及乙烯_丙烯酸乙 酉曰共聚物,乙烯-乙烯基羧酸共聚物諸如乙烯—丙烯酸共聚 物;乙稀-四環十二稀共聚物;聚丙稀樹脂諸如丙彿均致物 及丙烯—乙烯共聚物;聚-4-f基戊烯-1、聚丁烯—丨、聚丁 二烯、聚苯乙烯;丙烯腈_苯乙烯樹脂;丙烯腈—丁二烯_ 322813 27 201130418 苯乙稀樹脂;笨乙烯彈性體諸如苯乙烯共軛二烯嵌段共聚 物及氫化苯乙烯共軛二烯嵌段共聚物;氟樹脂;丙烯酸系 樹脂諸如聚曱基丙烯酸曱酯;聚醯胺樹脂諸如尼龍6及尼 龍66 ;聚酯樹脂諸如聚對苯二曱酸乙二酯、聚萘二甲酸乙 二酯(polyethylene naphthalate)、聚對笨二曱酸丁二醋 及聚對苯二甲酸伸環己基二亞曱酯(p〇lyCyCl〇hexylene dimethylene terephthalate);或多孔樹脂諸如聚碳酸 酯、聚縮酸、聚丙稀礙(polyacryl sulfone)、聚芳酯、經 基苯曱酸聚酯、聚醚醯亞胺、聚酯碳酸酯、聚苯醚樹脂、 聚氣乙烯、聚偏二氯乙烯、聚胺曱酸酯(polyurethane)、 發泡之聚胺曱酸酯、發泡之聚丙烯及發泡之乙烯)、玻璃、 金屬及陶瓷。 液態載體之實例包括芳族或脂族烴(如二曱苯、曱苯、 烧基萘、苯基二甲苯基乙烧、煤油、輕油、己院或環己院)、 鹵化烴(如氣苯、二氯曱烷、二氣乙烷或三氣乙烷)、醇(如 曱醇、乙醇、異丙醇、丁醇、己醇、苯曱醇或乙二醇)、醚 (如二乙醚、乙二醇二曱醚、二乙二醇單甲醚、二乙二醇單 乙醚、丙二醇單曱醚、四氫呋喃或二哼烷)、酯(如乙酸乙 酯或乙酸丁酯)、嗣(如丙酮、曱基乙基g同、曱基異丁基西同 或環己酮)、腈(如乙腈或異丁腈)、亞砜(如二曱基亞颯)、 醯胺(如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺或N_曱基_ 吡咯啶酮)、碳酸亞烷酯(alkylidene carbonate)(如碳酸 丙烯酯)、植物油(如大豆油或棉籽油)、植物精油(如撥油、 牛膝草油(hyssop oil)或檸檬油)及水。 322813 28 201130418 氣態載劑之實例包括丁烷氣體、氟氣碳化物、液化石 油氣(LPG)、二曱醚及二氧化碳。 界面活性劑之實例包括烷基硫酸鹽、烷基磺酸鹽、烧 基芳基續酸鹽、院基芳基醚、聚氧乙烯化烧基芳基峻、聚 乙二醇醚、多元醇酯及糖醇衍生物。 用於製劑之其他助劑之實例包括黏合劑、分散劑及安 定劑。具體而言’例如酪蛋白、明膠、多醣類(如殿粉、阿 拉伯膠、纖維素衍生物或褐藻酸)、木質素衍生物、膨土、 醣、合成之水溶性聚合物(如聚乙烯醇或聚乙烯吡咯咬酮)、 聚丙稀酸、BHT(2,6-二-第二丁基-4-甲基紛)及BHA(2-第 三丁基-4-曱氧基酚及3-第三丁基-4-曱氧基酚之混合 物)。 殺蟲線圈之基底材料之實例包括植物粉末(諸如木屑 及沈積物粉末)與黏合劑(諸如燻香材料粉末、澱粉及麩質) 之混合物。 電熱殺蟲片之基底材料之實例包括藉由將棉絨硬化 所獲得之板以及藉由將棉絨與木漿之混合物的原纖維 (pulp)硬化所獲得之板。 自燃型煙燻劑之基底物質之實例包括可燃性放熱劑 諸如硝酸鹽、亞确酸鹽、脈(guanidine)鹽、氯酸鉀、确化 纖維素、乙基纖維素及木粉;熱分解刺激劑諸如鹼金屬鹽、 驗土金屬鹽、重鉻酸鹽及路酸鹽;氧載劑諸如硝酸鉀;助 燃劑諸如三聚氰胺(melamine)及麥粉澱粉;增量劑諸如矽 躁土;以及結合劑諸如合成膠。 29 322813 201130418 化學反應型煙壎劑之基底材料之實例包括放熱劑諸 如驗金屬硫化物、多硫化物、硫氫化物及氧化舞;催化劑 諸如含碳材料、碳化鐵及活性白黏土;有機發泡劑諸如偶 氮二甲醯胺(azodicarbonamide)、苯續醯肼 (benzenesulfonylhydrazide)、二硝基五亞甲基四胺 (dinitropentamethylenetetramine)、聚苯乙烯及聚胺甲 酸醋,以及填充劑諸如天然纖維及合成纖維之條料。 使用作為樹脂蒸散製劑之基底材料的樹脂之實例包 括聚乙烯樹脂諸如低密度聚乙烯、直鏈低密度聚乙烯及高 密度聚乙烯;乙烯-乙烯酯共聚物諸如乙烯_乙酸乙烯酯共 聚物;乙烯-曱基丙烯酸酯共聚物諸如乙烯_曱基丙烯酸甲 醋共聚物及乙稀-甲基丙騎乙醋共聚物;乙稀_丙稀酸酿 共聚物諸如乙稀-⑽酸曱S旨共聚物及乙稀_丙烯酸乙醋共 聚物’乙歸-乙烯基共聚物諸如乙烯-丙稀酸共聚物; 乙稀四環十—婦共聚物;聚丙烯樹脂諸如丙婦共聚物及丙 稀“乙烯“聚物,聚—4_曱基戊烯一卜聚丁烯小聚丁二烯、 =笨—稀丙稀腈一笨乙烯樹脂;丙稀猜-丁二稀一苯乙稀樹 月二苯乙稀彈性體諸如苯乙烯共輛二稀嵌段共聚物及氣化 $乙烯八1¾—稀嵌段共聚物;I樹脂;丙稀酸系樹脂諸如 聚曱基丙稀酉义甲醋;聚醯胺樹脂諸如尼龍6及尼龍66 ;聚 酯樹脂諸如聚對苯二 __ τ ®文乙一西曰、聚萘二曱酸乙二酯、聚 *本甲酉夂丁一酉曰及聚對苯二甲酸伸環己基二亞甲酯;聚 碳酸醋、聚縮駿、聚丙稀石風、聚芳醋、經基苯甲酸聚醋、 聚醚醢亞胺、聚酿碳酸醋、聚苯喊樹脂、聚氣乙稀、聚偏 30 322813 201130418 二氯乙烯及聚胺甲酸酯。此等基底材料可單獨使用戈缸八 兩種或更多種而使用。若必要時,可於此等基底材料中0 入塑化劑諸如鄰苯二甲酸酯(如鄰苯二曱酸二曱酯、鄰笨: 曱酸二辛酯等;)、己二酸酯及硬脂酸。此樹脂蒸散製劑可藉 由混合本發明之化合物與基底材料,揉捏混合物,隨後^ 藉由射出成型法、擠出成型法或加壓成型法使其成型而製 備。所製得之樹脂製劑可進行進一步的成型或切割步驟, 若必要時,加工成諸如板、膜、帶、網或繩狀。此等樹脂 製劑可加工成動物頸圈、動物耳標、片狀產品、陷阱繩、 園藝支架及其他產品。 毒餌之基底材料之實例包括餌成分諸如榖類粉末、植 物油醋及結晶纖維素;抗氧化劑諸如二丁基經基曱苯及 去甲二氫愈創木酸(nord i hydrogua i aret i c ac i d);保存劑 =如去氫乙酸(dehydroacetic acid);用於孩童或寵物之 意外攝取抑制劑諸如辣椒粉;吸引昆蟲之香料諸如起司香 料、洋蔥香料及花生油。 本發明之害蟲防治方法通常係藉由將有效量之本發 月化&物,以本發明害蟲防治劑之形式施加於害蟲或其棲 息處(如植物體、土壤、房屋内部、動物體、車子内部或室 外開放空間)而實施。 鉍加本發明害蟲防治劑之方法包括下列方法,且係根 據本發明$蟲防治劑m使用n域等㈣當地選擇。 (1) 一種方法,係包含將本發明之害蟲防治劑施加於害蟲或 害蟲之棲息處。 322813 31 201130418 (2) —種方法,係包含將本發明之害蟲防治劑以溶劑(例如 水)稀釋後,接著再將稀釋液喷灑於害蟲或害蟲之棲息處9 於此方法中,本發明之害蟲防治劑通常配製成可乳化濃縮 物、可濕性粉末、可流動性製劑、微膠囊等。通常係將製 劑稀釋,以使本發明化合物之濃度可成為0. 1至10, 000 ppm ° (3 ) —種方法,係包括將本發明害蟲防治劑於害蟲之棲息處 加熱,而使活性成分由害蟲防治劑揮發並擴散。 在此例中,本發明化合物之施加量及濃度皆可根據形 式、施加時間、施加區域、施加方法、害蟲種類、欲造成 之傷害等而適當地決定。 當本發明之化合物用於預防流行病時,本發明化合物 於空間中之施加量通常為0. 0001至1,000 mg/m3,以及本 發明化合物於平面之施加量為0. 0001至1,000 mg/m2。根 據製劑之形式,殺蟲線圈或電熱殺蟲片係藉由加熱使活性 成分揮發並擴散而施加。樹脂蒸散製劑、紙蒸散製劑、非 織造織物蒸散製劑、針織織物蒸散製劑或昇華錠劑係允許 直接將其置於欲施加之空間中,並且放置於吹風下。 當以預防流行病為目的而將本發明之害蟲防治劑施 加於空間中時,空間之實例包括衣櫃、日式壁櫥、日式五 斗櫃、碗櫃、廁所、浴室、遮棚、客廳、餐廳、車庫、車 子内部等。此害蟲防治劑亦可施加於室外開放空間。 當本發明之害蟲防治劑用於防治家畜(諸如牛、馬、 豬、綿羊、山羊及雞)以及小型動物(諸如狗、貓、大鼠及 32 322813 201130418 小鼠)之外部寄生蟲時,本發明之害蟲防治劑可藉由獸醫領 域中已知的方法施加於動物。具體而言,當欲進行全身性 防治時,本發明之害蟲防治劑係以錠劑、與飼料之混合物 或栓劑之形式、或者藉由注射(包括肌肉、皮下、靜脈内及 腹膜内注射)而投予至動物。另一方面,當欲進行非全身性 防治時,本發明之害蟲防治劑係藉由下述方法施加至動 物:喷灑油溶液或水性溶液、洗注(p〇ur-〇n)處理或滴注 (sp〇t-〇n)處理或以洗髮精製劑清洗動物或將由樹脂蒸散 製劑所製成之頸圈或耳標配戴於動物。在投予至動物體之 實例中,本發明化合物之劑量範圍通常為每丨公斤動物體 重使用0. 1至1,〇〇〇 mg。 當本發明之害蟲防治劑使用於農業領域之害蟲防治 時,其用量可根據施加時間、施加區域、施加方法及其他 因素而廣泛地變動,並且以每1〇, 000 ra2而論,本發明化 合物之用量通常在1至10, 〇〇〇 g之範圍内。當本發明之害 蟲防治劑製備成可乳化濃縮物、可濕性粉末、可流動性製 劑等時,害蟲防治劑通常是以水稀釋使活性成分之濃度成 為〇· 01至10, 〇〇〇 ppm後再施加,而顆粒或粉劑則通常以 原樣使用。 此等製劑或製劑之水稀釋液可直接喷灑於害蟲或植 物(諸如作物植物)以防止害蟲,或者可使用於土壤處理以 防治棲息於農耕地土壤中之害蟲。 ,亦可藉由下述方法進行施加:將形成片狀或繩狀或線 狀製劑之樹脂製劑直接捲繞於植物周圍;將製劑配置於植 322813 33 201130418 物或將製劑麵於根部之土壤表面。 本發月之化合物可作為 諸如農場,'草地或果園==於= 合物可防治棲息於農耕 W農耕土地。本發明之化 述“植物作#”。 H此農耕土地係耕作下 稻'小麥、大麥、黑麥㈣、燕 杯1、棉、黃豆、花生、騫麥(沾咖⑻、甜菜、油 菜籽、向曰葵、甘蔗、菸草等; * ^菜.加科蔬菜($子H青椒、辣椒、馬龄箸 等)’萌蘆科蔬菜(胡瓜、南瓜、筒瓜、西瓜、甜瓜等);十 字祀科蔬菜(曰本蘿蔔、蕪菁、辣根、球莖甘藍、大白菜、 高麗菜、黑芥(brown mustard)、青花菜、花椰菜等);菊 科蔬菜(牛蒡、茼蒿、朝鮮薊、萵苣等);百合科蔬菜(蔥、 洋蔥、蒜、蘆筍等);繳形花科蔬菜(胡蘿蔔、洋芽、芽菜、 防風草(parsnip)等);藜科蔬菜(菠菜、瑞士甜菜(Swiss chard)等);薄荷科蔬菜(曰本羅勒、薄荷、九層塔等);草 莓、蕃薯、山藥、芋(aroid)等; 果樹:仁果類(蘋果、普通梨木、日本梨、木瓜、棍 梓(quince)等);核果類(桃、李、油桃、日本李、櫻桃、 杏、洋李等);柑橘類植物(蜜柑(Satsuma mandarin)、柳 橙、檸檬、萊姆、葡萄柚等);堅果類(栗、胡桃、榛果、 杏仁、開心果、腰果、澳洲胡桃等);漿果類(藍莓、蔓越 莓、黑莓、覆盆子等);葡萄、柿、撖欖、枇杷、香蒸、^加 啡、棗、椰子、油椰子(oil palm)等; 322813 34 201130418 果祕以外之樹種.茶樹、桑樹、木本植物(杜鵑花屬、 山茶花屬、繡球屬(hydrangea)、山茶花(sasanqua)、莽草 (I^iciumreligiosum)、櫻木、百合木(tuHptree)、細 葉紫薇(crape myrtle)、吊鍾花(fragrant〇Hve)等)、行 道樹(椁樹、樺樹、山茱萸、尤加利(eucalyptus)、銀杏、 溆丁香、楓樹、橡樹、白揚樹、紫荊、楓香、梧桐、櫸樹、 曰本側柏、冷杉、日本鐵杉、杜松、松樹、雲杉、紫杉、 榆木、七葉樹(horse chestnut)等)、珊瑚樹、羅漢松 (Podocarpus macrophyllus)、日本杉(japanese cedar)、 曰本扁柏(Japanese cypress)、八豆屬(cr〇t〇n)、紡錘樹 (spindle tree)、山楂(Chainese howthorn)等; 草坪(Lawn):結縷草屬(zoysia)(曰本結縷草、台北 草(mascarene grass)等)、狗牙根(Bermuda grass)(普通 狗牙根(Cynodon dactylon)等)、小糠草(匍匐性小糠草 (creeping bent grass)、翦股穎草(Agrostis stolonifera)、細弱翦股穎(Agrostis tenuis)等)、早熟 禾屬(bluegrass)(肯塔基藍草、粗莖早熟禾等)、羊茅(高 羊茅、軟羊茅、匍匐紫羊茅等)、黑麥草(毒麥(darne 1)、 多年生黑麥等)、鴨茅、貓尾草(timothy grass)等; 其他:花(玫瑰、康乃馨、菊花、洋桔梗(土耳其桔梗 (prairie gentian))、滿天星、非洲菊、金盞花、鼠尾草、 矮牵牛、馬鞭草、鬱金香、紫菀屬、龍膽花、百合花、三 色紫蘿蘭、仙客來、蘭花、鈴蘭、薰衣草、紫羅蘭、葉牡 丹、報春花、聖誕紅、劍蘭、洋蘭、雛菊、馬鞭草、東亞 35 322813 201130418 蘭類(cymbidium)、秋海棠等)、生物燃料植物(麻風樹屬、 紅花、亞麻齐油(g〇ld-of-pleasure)、柳枝稷 (switchgrass)、芒草、白紋條葉草蘆、蘆竹、洋麻、樹薯、 柳等)、觀葉植物;等。 上述“植物作物”包含基因轉殖植物作物。 本發明之化合物可與其他殺蟲劑、殺蟎劑、殺線蟲 劑、土壌害蟲防治劑、殺真菌劑、除草劑、植物生長調節 劑、蟲類拒避劑(repellent)、增效劑(synergist)、肥料 或土壤改良劑混合或組合使用。 此等殺蟲劑及殺蟎劑之活性成分之實例包括: (1)合成性除蟲菊精(pyrethroid)化合物類: 阿納寧(acrinathrin)、亞列寧(allethrin)、yS-赛 扶寧(beta-cyf luthrin)、畢芬寧(bifenthrin)、乙氰菊酯 (cycloprothrin)、賽扶寧(cyfluthrin)、赛洛寧 (cyhalothrin)、賽滅寧(cypermethrin)、益避寧 (empenthrin)、第滅寧(deltamethrin)、益化利 (esfenvalerate)、醚菊酯(ethofenprox)、芬普寧 (fenpropathrin)、芬化利(fenvalerate)、護賽寧 (flucythrinate)、伏芬普斯(flufenoprox)、氟氯苯菊酯 (flumethrin)、福化利(fluvalinate)、合芬寧 (halfenprox)、益普靈(imiprothrin)、百滅寧 (permethrin)、普亞列寧(pral lethrin)、除蟲菊酯 (pyrethrins)、異列滅寧(resmethrin)、σ-赛滅寧 (sigma-cypermethrin)、石夕護芬(si laf luofen)、七氟菊酯 36 322813 201130418 (tefluthrin)、泰滅寧(tralomethrin)、四氟苯菊酯 (transfluthrin)、治滅寧(tetramethrin)、苯喊菊醋 (phenothrin)、赛酚寧(cyphenothrin)、α-赛滅寧 (alpha-cypermethrin)、(-賽滅寧(zeta-cypermethrin)、 λ-賽洛寧(lambda-cyhalothrin)、7-賽洛寧 (gamma-cyhalothrin)、伏滅靈(furamethrin)、r -福化利 (tau-f luvalinate)、美特寧(metof luthrin)、2, 2-二曱基 -3-(1-丙烯基)環丙烷羧酸2, 3, 5, 6-四氟-4-曱基苯甲酯、 2, 2-二甲基-3-(2-曱基-1-丙烯基)環丙烧致酸2, 3, 5, 6-四氟-4-(曱氧基曱基)苯曱酯、2, 2, 3, 3-四曱基環丙烷羧酸 2,3, 5, 6-四氟-4-(曱氧基曱基)苯甲酯等; (2)有機磷化合物類: 跋殺松(acephate)、墙化I呂、丁硫松(butathiofos)、 硫線構(cadusafos)、氯氧磷(chlorethoxyfos)、克芬松 (chlorfenvinphos)、陶斯松(chlorpyrifos)、曱基陶斯松 (chlorpyrifos-methyl)、氰乃松(cyanophos) : CYAP、大 利松(diazinon)、DCIP(dichlorodiisopropyl ether)、酴 線磷(dichlofenthion) ·· ECP、二氯松(dichlorvos) : DDVP、 大滅松(dimethoate)、甲基毒蟲畏(dimethylvinphos)、二 硫松(disulfoton)、EPN、愛殺松(ethion)、普伏松 (ethoprophos)、益多松(etrimfos)、芬殺松(fenthion): 1^?、撲滅松(£611丨1;1*〇1:11丨011).1£?、福赛絕({〇31:11丨323七6)、 福木松(formothion)、磷化氫、亞芬松(isofenphos)、加 福松(isoxathion)、馬拉松(malathion)、馬硫松 37 322813 201130418 (mesulfenfos)、滅大松(methidathion) : DMTP、亞素靈 (monocrotophos)、二溴構(naled) : BRP、異亞颯磷 (oxydeprofos) : ESP、巴拉松(parathion)、裕必松 (phosalone)、亞胺硫磷(phosmet) : PMP、甲基0密唆磷 (pirimiphos-methyl)、塔硫磷(pyridafenthion)、11 奎硫填 (quinalphos)、赛達松(phenthoate) : PAP、佈飛松 (profenofos)、丙蟲磷(propaphos)、普硫松(prothiofos)、 白克松(pyraclofos)、蔬果磷(salithion)、硫丙填 (sulprofos)、丁基》密咬填(tebupirimfos)、雙硫磷 (temephos)、殺蟲畏(tetrachlorvinphos)、托福松 (terbufos)、硫滅松(thiometon)、三氣松(trichlorphon): DEP、繁米松(vamidothion)、福瑞松(phorate)、硫線填 (cadusafos)等; (3)胺基甲酸酯(Carbamate)化合物類: 棉鈐成(alanycarb)、免敵克(bendiocarb)、免扶克 (benfuracarb)、BPMC、加保利(carbaryl)、克百威 (carbofuran)、丁基加保扶(carbosulfan)、地蟲威 (cloethocarb)、乙硫苯威(ethiofencarb)、仲丁威 (fenobucarb)、芬硫克(fenothiocarb)、芬諾克 (fenoxycarb)、呋線威(furathiocarb)、異丙威 (isoprocarb) : MIPC、速滅威(metolcarb)、納乃得 (methomyl)、滅賜克(methiocarb)、NAC、殿殺滅(oxamyl)、 抗芽威(pirimicarb)、安丹(propoxur) : PHC、XMC、硫雙 威(thiodicarb)、滅殺威(xylylcarb)、得滅克(aldicarb) 38 322813 201130418 等; (4) 沙蠶毒素(Nereistoxin)化合物類: 培丹(cartap)、免速達(bensultap)、殺蟲環 (thiocyclam)、殺蟲單(monosultap)、殺蟲雙(bisultap) 等; (5) 新類尼古丁(Neonicotinoid)化合物類: 益達胺(imidacloprid)、烯咬蟲胺(nitenpyram)、亞 滅培(acetamiprid)、喧蟲唤(thiamethoxam)、β塞蟲琳 (thiacloprid)、達特南(dinotefuran)、可尼丁 (clothianidin)等; (6) 苯甲醯脲(Benzoylurea)化合物類: 克福隆(chlorfluazuron)、雙三氟蟲脲 (bistrifluron)、汰芬隆(diafenthiuron)、除蟲脲 (diflubenzuron)、氟咬蜱脲(fluazuron)、氟環脲 (flucylcoxuron)、氟芬隆(flufenoxuron)、六伏隆 (hexaflumuron)、祿芬隆(lufenuron)、諾伐隆 (novaluron)、多氟蟲醯脲(noviflumuron)、得福隆 (teflubenzuron)、殺鈐脲(triflumuron)、三唾隆 (triazuron)等; (7 )苯基°比唾(Pheny 1 py razo 1 e )化合物類: 乙酿蟲肼(acetoprole)、乙蟲清(ethiprole)、芬普 尼(fipronil)、D比洛胺(vaniliprole)、氟轰肼 (pyriprole)、丁稀氟蟲肼(pyrafluprole)等; (8)Bt毒素殺蟲劑: 39 322813 201130418 衍生自蘇力菌(Baci 1 lus thuringiesis)之活抱子或 由蘇力菌所產生之結晶毒素、及其混合物; (9) 肼(Hydrazine)化合物類: 可芬諾(chromafenozide)、氯蟲醯肼 (halofenozide)、滅芬諾(methoxyfenozide)、抑盘胼 (tebufenozide)等; (10) 有機氯化合物類: 阿特靈(aldrin)、地特靈(dieldrin)、除蜗靈 (dienochlor)、硫丹(endosulfan)、曱氧基氯 (methoxychlor)等; (11) 天然殺蟲劑: 機油、菸鹼-硫酸鹽; (12) 其他殺蟲劑: 阿維菌素-B(avermectin-B)、溴瞒酯 (bromopropylate)、布芬淨(buprofezin)、溴蟲清 (chlorphenapyr)、滅繩胺(cyromazine)、D-D(l,3-二氯丙 稀)、因滅丁(emamectin-benzoate)、芬殺蜗(fenazaquin)、 D比氟硫璘(flupyrazofos)、稀蟲乙酯(hydroprene)、美賜 年(methoprene)、因得克(indoxacarb)、0惡蟲酮 (metoxadiazone)、倍脈心-A (milbemycin-A)、派滅淨 (pymetrozine)、咬蟲丙趟(pyridalyl)、百利普芬 (pyriproxyfen)、賜諾殺(spinosad)、氟蟲胺 (sulfluramid)、唾蟲醯胺(tolfenpyrad)、α坐騎威 (triazamate)、氟蟲酿胺(flubendiamide)、彌拜菌素 40 322813 201130418 (lepimectin)、珅酸(Arsenic acid)、苯克赛 (benclothiaz)、氰胺化約(Clacium cyanamide)、多硫化 鈣(Calcium polysulfide)、可氣丹(chlordane)、DDT、 DSP、伏芬靈(f lufenerim)、氟尼胺(f lonicamid)、氟蟲芬 (flurimfen)、覆滅蜗(formetanate)、安百故 (metam-ammonium)、威百故(metam-sodium)、溴化曱燒、 油酸鉀、普奇芬(protrifenbute)、螺曱蜗酯 (spiromesifen)、硫、氰氟蟲腙(metaf lumizone)、螺蟲乙 酯(spirotetramat)、必克松(pyrif luquinazone)、多殺菌 素(3卩丨1161:(^3111)、氣轰酿胺(〇111〇犷3111^311丨11口1*〇16)、滅釘 螺(tralopyril)等。 蟲類拒避劑之活性成分之實例包括N,N-二乙基-間-甲苯醯胺、檸檬烯(limonene)、沈香油莠醇(linalool)、 香茅越(citrone 11 al)、薄荷醇(menthol)、薄荷_ (menthone)、日本扁柏油(hinokitiol)、天竺赛醇 (geraniol)、桉油醇(eucalyptol)、因得克(indoxacarb)、 蒈烷-3, 4-二醇(carane-3, 4-diol)、MGK-R-326、MGK-R-874 及 BAY-KBR-3023 。 增效劑之活性成分之實例包括5-[2-(2-丁氧基乙氧 基)乙氧基曱基]-6-丙基-1,3-苯并二氧雜環戊婦、N-(2-乙基己基)雙環[2. 2. 1]庚-5-烯-2, 3-二羧醯亞胺、八氣二 丙基醚(octachlorodipropylether)、氰硫基乙酸異莰酯 (thiocyanoacetic acidisobornyl)、N-(2-乙基己基)-1-異丙基-4-曱基雙環[2. 2. 2]辛-5-稀-2, 3-二羧_癒亞胺。 41 322813 201130418 [實施例] 以下將藉由製造例、參考製造例、調配例及試驗例更 進一步詳細說明本發明,然而本發明並不限於此等實施例。 首先,本發明化合物之製造例係顯示如下。舉例而言, 於1H-NMR中,描述方式“1.21 + 1.22(s+s,3H)”係指於 1.21 ppm及1.22 ppm存在有單峰之波峰,且此兩個波峰 之總積分值為3H。 製造例1 於2-羥曱基-5-曱基-4-(2-丙炔基)-2, 4-二氫-[1,2, 4]三唾-3-酮(1. 00g,6. OOmmol)及(1R)-反-3-[ (1EZ) -2 -氰基-2-(曱基硫基)乙婦基]-2, 2-二曱基環丙烧叛酸 (1.26g,5.97mmol)之氯仿溶液(20mL)中,加入1-乙基-3-(3-二甲基胺基丙基)碳二亞胺鹽酸鹽(1. 60g,8· 35mmol) 及4-二曱基胺基吡啶(30mg)。於室溫攪拌此混合物48小 時後,將水倒入反應混合物中,並且以乙酸乙酯萃取此溶 液。有機層以硫酸鎂脫水後,接著於減壓下濃縮,將殘餘 物進行矽膠管柱層析法而獲得1.35g下式所示之(1R)-反 -3_[(1EZ)-2 -氮基-2-(曱基硫基)乙稀基]- 2,2-二曱基環 丙烷羧酸3-曱基-5-側氧基-4-(2-丙炔基)-4, 5-二氫 -[1,2,4]三唑基甲酯邙:2= 50:50)(以下稱為本發明之化 合物0)): 42 322813 201130418
h3c ch3 、合ch=c(cn)sch3 o o ^-NMRiCDCls^MS) δ (ppm) : 1.20+1.21 (s+s, 3H>, 1.32+1.34 (s+s,3H), 1.79 to 1.82(d,lH), 2.35(s,3H), 2.37(m,lH), 2.40+2.46(s+s,3H), 2.49 to 2.53(m, 1H), 4.44(d,2H,2.4Hz), 5.67 to 5.82(m,2H), 6.13 (d,0.5H,J =10.0 Hz), 6.17(d,0.5H, J =10.0 Hz) 製造例2 將製造例1所得之(li〇-反-3-[(lEZ)-2-氰基-2-(曱 基硫基)乙稀基]-2,2-二曱基環丙院緩酸3 -曱基-5-側氧 基-4-(2 -丙快基)-4,5-二氮-[1,2, 4]三σ坐基曱醋藉由石夕膠 管柱層析法(洗提液:己烧/乙酸乙酯=2 : 1)純化為Ε異構 物及Ζ異構物,而獲得呈具有較高極性區分(fraction)的 下式所示之(1R)_反_3-[(1Ε)-2-氰基-2-(曱基硫基)乙稀 基]- 2, 2-二甲基環丙烧缓酸3-曱基-5-側氧基-4-(2-丙炔 基)-4, 5-二氫-[1,2, 4]三σ坐基曱S旨(以下稱為本發明之化 合物(2)): 43 322813 201130418
白色結晶,熔點為104.0至105.0°(::屮-删1^(仁〇(:13,11^)5(??11〇:1.21 (s,3H), 1.34(s,3H), 1.81(d,1H, J=5.2Hz)f 2.35(s,3H),2.37 (m,lH), 2.40(s,3H), 2.49to2.53(dd,lH>,4.44(d,2H,2.8Hz), 5.75(dd,2H), 6.13(d,lH,J=l〇.〇Hz) 製造例3 操作係以與製造例1相同之方式進行,但使用2-羥曱 基-5_甲基_4-(2 -丙快基)-2,4-二氮-[1,2, 4]三〇坐-3-酉同取 代3-羥曱基-1-(2-丙炔基)咪唑啶-2, 4-二酮,以及使用 (1R)-反- 3_[(1ΕΖ)-2 -氮基-2-(乙基硫基)乙稀基]_2,2-二 曱基環丙院叛酸取代(1R)_反_3-[(1ΕΖ)-2-氰基-2-(曱基 硫基)乙烯基]-2, 2-二甲基環丙烷羧酸,而獲得下式所示之 (1R)-反- 3-[(1ΕΖ)_2_氮基_2-(乙基硫基)乙稀基]_2,2_二 甲基環丙烷羧酸3-甲基-5-側氧基-4-(2-丙炔基)-4, 5-二 氫-[1,2,4]三唑基甲酯(E: Z= 50: 50)(以下稱為本發明之 化合物(3)):
44 322813 201130418 淡黃色液體:h-NMIUCDClhTMS) δ (ppm) : 1.20 to 1.37 (in, 9H, E+Z 異構物),1.81(d,0.5H, Z 異構物 >,1.83(d,0.5H, E 異構物),2·36 (s,3H), 2.37(m,lH〉,2·53(πι, 1H>, 2.84(q,lH, E 異構物),2·91 (q,lH, Z 異構物4.43(d, 2H), 5.67to5.82(m,2H), 6.20(d, 0.5H, E 異構物),6.24(d,0.5H, Z 異構物) 製造例4 將製造例3所獲得之(1R)-反-3-[(lEZ)-2-氰基-2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸3-曱基-5-側 氧基-4-(2-丙炔基)-4, 5-二氳-[1,2, 4]三唑基甲酯進行矽 膠管柱層析(洗提液:己烷/乙酸乙酯=2 : 1),而獲得呈具 有較向極性區分的下式所不之(1R)_反_3_[(1Ε)-2 -氮基 -2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸3-曱基 -5-側氧基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三0坐基曱酉旨 (以下稱為本發明之化合物(4)):
H3C CH3 δ〇Η2〇Η3 淡黃色液體:^-NMRiCDClhTMS) δ(ρριη): 1.21(s,3H>, 1.30(t, 3H), 1.34 (s,3H), 1.83(d,lH), 2.36(s, 3H), 2.37(m,lH), 2.53(dd, 1H), 2.84 (q,2H), 4.44(d,2H), 5.75(dd,2H), 6.20(d,lH) 製造例5 將製造例3所獲得之(1R)-反-3-[(lEZ)-2-氰基-2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸3-曱基-5-側 氧基-4-(2-丙炔基)-4, 5-二氳-[1,2, 4]三唑基甲酯進行矽 45 322813 201130418 膠管柱層析(洗提液:己院/乙酸乙醋=2: 1),而獲得呈具 有較低極性之分液的下式所示之(1R)_反_3-[(1ΕΖ)-2 -氮 基- 2-(乙基硫基)乙婦基]-2,2_二曱基環丙烧叛酸3_曱基 -5-側氧基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基曱酯 (E : Z= 33 : 67)(以下稱為本發明之化合物(5)):
淡黃色液體:iH-NMRiCDClhTMSMippm): 1.20(s, 3H), 1.32(s,3H>, 1.31tol.34(t,3H), 1.81(d,0.67H, Z 異構物),1.83(d,0.33H, E 異構物),2.36(s, 3H), 2.37(m,lH), 2.54(m,lH), 2.91(q, 1H), 4.43(d, 2H),5.67 to 5.82(m,2H>, 6.20(d,0.33H, E 異構物),6.24 (d,0.67H, Z 異構物) 製造例6 將製造例1所得之(1R)-反-3-[(lEZ)-2-氰基-2-(曱 基硫基)乙烯基]-2, 2-二甲基環丙烷羧酸3-曱基-5-側氧 基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基甲酯進行矽膠 管柱層析(洗提液:己烷/乙烯乙酯=2 : 1),而獲得呈具有 較高極性之分液的下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基 -2-(曱基硫基)乙烯基]-2, 2-二甲基環丙烷羧酸3-曱基 -5_側氧基_4-(2 -丙快基)-4,5_二氫-[1,2, 4]三0坐基曱酉旨 (E : Z= 80 : 20)(以下稱為本發明之化合物(6)): 46 322813 201130418
淡黃色液體:h-NMiUCDClhTMS) δ(ρρπι): 1.20+1.21(s+s,3H), 1.32 + 1.34(s+s,3H), 1.79tol.82(d,lH), 2.35(s,3H), 2.37(m,lH>, 2.40+2.46(s+s,3H), 2.49 to 2.53(m, 1H) , 4.44(d,2H,2.4Hz), 5.67to5.82(m,2H), 6.13 (d,0.8H,J= 10.0 Hz), 6.17 (d,0.2H, J = 10.0 Hz) 製造例7 將製造例3所獲得之(1R)-反-3-[(lEZ)-2-氰基-2-(乙基硫基)乙稀基]-2,2-二甲基環丙烧叛酸3_曱基-5_側 氧基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基曱酯進行矽 膠管柱層析(洗提液:己烷/乙酸乙酯=2 : 1),而獲得呈具 有較高極性之分液的下式所示之(1R)-反-3-[(1ΕΖ)-2-氰 基-2-(乙基硫基)乙稀基]-2,2-二曱基環丙烧叛酸3_曱基 -5-側氧基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基甲酯 (E : Z=90 : 10)(以下稱為本發明之化合物(7)):
淡黃色液體:h-NMIUCDClhTMSmppin) : 1.20 (s, 3H) , 1.32(s,3H), 1.31 to 1.34(t,3H), 1.81 (d,0.1H, Z 異構物),1.83(d,0.9H, E 異構物),2.36(s, 3H), 2.37(m,lH), 2.54(m,lH), 2.91(q, 1H), 4.43(d, 2H},5.67 to 5.82(m,2H), 6.20(d,0.9H, E 異構物),6.24 (d,0.1H, Z 異構物) 47 322813 201130418 製造例8 將製造例3所獲得之(1R)-反-3-[(1ΕΖ)-2-氰基-2_ (乙基硫基)乙稀基]-2,2 -二甲基環丙烧叛酸3 -曱基-5 -側 氧基-4-(2-丙炔基)-4, 5-二氫-[1, 2, 4]三唑基曱酯進行矽 膠管柱層析(洗提液:己烷/乙酸乙酯=2 : 1),而獲得呈具 有較高極性之分液的下式所示之(1R)-反-3-[(1ΕΖ)-2-氰 基-2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸3-甲基 -5-側氧基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基甲酯 (E : Z= 80 : 20)(以下稱為本發明之化合物(8)):
淡黃色液體:iH-NMRiCDClhTMSMippm) : 1.20 (s, 3H) , 1.32 (s,3H), 1.31 to 1.34(t,3H>, 1.81 (d,0.2H, Z 異構物),1.83(d,0.8H, E 異構物),2.36(s, 3H), 2.37(m,lH), 2.54(m,lH), 2.91(q, 1H), 4.43(d, 2H),5.67 to 5.82(m,2H), 6.20(d,0.8H, E 異構物), 6.24(d,0.2H, Z 異構物) 有關羧酸化合物(3)等之製造,係如以下參考製造例 所示。 參考製造例1 將(1R)-反-3-曱醯基-2, 2-二曱基環丙烷羧酸曱酯 (6.41g,41.1mmol)、甲基硫基乙腈(3.94g,45.2mmol)及 碳酸鉀(6. 24g,45. 2mmol)加入N,N-二曱基曱醯胺(40mL) 與甲苯(15mL)之混合物中,隨後在100°C攪拌3小時。將 48 322813 201130418 反應混合物冷卻至室溫並加入2〇〇ml之冰水中,將溶液以 乙酸乙S旨萃取兩次(每次1 〇〇mL)。合併所得之乙酸乙g旨層, 以飽和鹽水(50mL)清洗1次,隨後以硫酸鎂脫水。在減壓 下將有機層濃縮後,將殘餘物進行矽膠管柱層析而獲得 8. 23g下式所示之(1R)-反~3-[(lEZ)-2-氮基-2-(甲基硫 基)乙烯基]-2,2-二甲基環丙烷羧酸甲酯: h3c ch3 Y^CH^CiCNJSCHa H3CO-^; 無色液體··iH-NMRiCDCh, TMS) 5(ppm): 1.23+1.24(s+s,3H), 1.32 + 1.33(s+s,3H), 1.79+1.80(d+d, 1H,J= 5.2 Hz>, 2.40+2.46 (s+s, 3H), 2.50 to 2.53(m/lH), 3.70 (s,3H), 6.18+6.21(d+d, 1H,J= 10.0Hz) 參考製造例2 將(1R)-反-3-[(lEZ)-2-氰基-2-(甲基硫基)乙烯基] -2, 2-二曱基環丙烷羧酸曱酯(2. 29g,10. 2mmol)溶解於曱 醇(6mL)與水(10mL)之混合物中,並於其中加入氫氧化卸 (1. lg,19. 6mmol) ’隨後在室溫攪拌12小時。將反應混合 物加入冰水(30mL)中,並以乙酸乙酯(20mL)萃取此溶液。 於所得之水層中加入鹽酸直到pH變成2,隨後以乙酸乙酯 (30mL)萃取兩次。將所得之乙酸乙酯層合併,以飽和鹽水 (30mL)清洗2次,接著以硫酸鎂脫水。於減壓下濃縮有機 層後,獲得2. 08g下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基 -2-(曱基硫基)乙烯基]-2,2-二曱基環丙烷羧酸: 49 322813 201130418
HO Ύ) ^CH=C(CN)SCH3 淡黃色結晶:4-剛只(00(:13, TMS} δ(ρρπι): 1.24 + 1.25(S+S,3H), 1.36 +1.37(s+s,3H), 1.79+1.81(d+d, 1H, J = 5.2 Hz), 2.41+2.47(s+s, 3H}, 2.50 to 2.56(m,1H), 6.17+6.21(d+d,lH,E+Z,J=10.4Hz) 參考製造例3 將氣乙腈(4.0g, 53.0mmol)及碳酸斜(8.8g, 63.8mmol) 加入N,N-二甲基甲醯胺(3〇mL)中,並且在冰冷下將乙硫醇 (3· 7mL,49. 9mmol)加入其中,隨後在室溫攪拌24小時。 之後’加入(1R)-反-3-甲醯基-2, 2-二曱基環丙烷羧酸曱酯 (8.20g, 52.6mmol)及碳酸奸(9.〇g,65.2mmol),隨後再於 至/jtt進一步授拌24小時。將反應混合物加入至冰水(1 〇〇mL) 中,並且此溶液以乙酸乙酯萃取兩次(每次1 〇〇mL)。將所 得之乙酸乙酯層合併,以飽和鹽水(50mL)清洗丨次,接著 =硫酸鎖脫水。於減壓下濃縮有機層,將殘餘物進行石夕膠 管柱層析’以獲得9.93g下列通式所示之(1趵__反_3— [(1ΕΖ)-2-氰基—(乙基硫基)乙烯基]_2,2〜二甲基環丙烷 羧酸曱酯: 1 < 322813 50 201130418 pH=C(CN)SCH2CH3
0 。 無色液體 ^H-NMRiCDClh TMS) δ(ρριη): 1.23+1.24(s+S,3H>, 1.26 to 1.33(m,3H), 1.33+1.35(s+s,3H), 1.79 to 1.83(m, 1H), 2.50 to 2.55(m, 1H), 2.84 to 2.90 (m,2H), 3.71(s,3H), 6.25 to 6.29(m,lH) 參考製造例4 在將(1R)-反-3-[(1ΕΖ)-2 -氮基-2-(乙基硫基)乙稀 基]-2, 2-二曱基環丙烷羧酸甲酯(9. 90g, 41. 4mmol)溶解 於曱醇(15mL)及水(5mL)之混合物中後,於其中加入氫氧化 鉀(3. 5g,62. 5mmol),接著於室溫攪拌12小時。將反應混 合物加入冰水(60mL)中,並且將此溶液以乙酸乙酯(50mL) 萃取。於所得之水層中加入鹽酸直到pH成為2,隨後以乙 酸乙酯(50mL)萃取2次。將所得之乙酸乙酯層合併,以飽 和鹽水(50mL)清洗2次,接著以硫酸鎂脫水。於減壓下濃 縮有機層後,獲得8. 98 g下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基-2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸: H^C CH,
參考製造例5 於(1R)-反-3-[(1ΕΖ)-2 -氰基-2-(乙基硫基)乙稀基] -2, 2-二曱基環丙烷羧酸(8. 98g,39. 9mmol)中加入曱苯 51 322813 201130418 (25mL),接著再加入亞硫醯氯(5.0g,42.0mmol)。此外, 加入N,N-二曱基甲醯胺(50mg),隨後在内部溫度60至70°C 攪拌4小時。於減壓下將反應混合物濃縮,而獲得9. 62 g 下式所不之(1R)_反_3_[(1ΕΖ)-2 -氮基_2_(乙基硫基)乙稀 基]-2,2-二甲基環丙烷羧醯氣:
參考製造例6 反應係以與參考製造例3相同之方式進行,但使用丙 硫醇取代乙硫醇,而獲得下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基-2-(丙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸曱酯:
無色液體 ^H-NMiMCDClh TMS) 5(ppm):0.99tol.00(m,3H), 1.23+ 1.24(s+s,3H), 1.33+1.35(s+s, 3H) , 1.62 to 1.70(m,2H), 1.79 to 1.82(m,lH>, 2.50 to 2.56 (m,lH), 2.80 to 2.89(m,2H), 3.71 (s,3H),6.23 to 6.28(m,1H) 參考製造例7 反應係以與參考製造例4相同之方式進行,除了使用 (1R)-反-3-[(1ΕΖ)-2-氰基-2-(丙基硫基)乙烯基]-2, 2-二 52 322813 201130418 曱基環丙烷羧酸曱酯取代(1R)-反-3-[(1ΕΖ)-2-氰基-2-(乙基硫基)乙烯基]-2,2-二曱基環丙烷羧酸曱酯,而獲得 下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基-2-(丙基硫基)乙稀 基]-2,2-二曱基環丙烷羧酸: u r' r*u
淡黃色固體 ^H-NMRiCDClh TMS> δ(ρριη): 0.99 to 1.04(m,3H>, 1.25+1.26(s+s,3H), 1.36+1.37(s+s,3H), 1.62 to 1.70(m,2H), 1.79 to 1.83(m,lH),2.53 to 2.56 (m,lH>,2.80 to 2.90(m,2H), 6.23 to 6.28(m,lH) 參考製造例8 反應係以與參考製造例3相同之方式進行,除了使用 丁硫醇取代乙硫醇,而獲得下式所示之(1R)-反-3-[(1ΕΖ) -2-氰基-2-(丁基硫基)乙稀基]-2, 2-二甲基環丙烧叛酸曱
53 322813 201130418 無色液體 ^H-NMRiCDClh TMS) δ(ρρια): 0.92 to 0.95(m,3H), 1.22 + 1.23(s+s,3H), 1.32+1.33(s+s, 3H, 1.41 to 1.65(m,4H), 1.79 to 1.82(m,1H),2.52 to 2.56(m, 1H),2.80 to 2.91(m, 2H),3.71(s,3H), 6.22 to 6.28(m,lH) 參考製造例9 反應係以與參考製造例4相同之方式進行,除了使用 (1R)-反-3-[(1ΕΖ)-2-氰基-2-(丁基硫基)乙烯基]-2, 2-二 曱基環丙烧叛酸甲自旨取代(1R)_反- 3- [(1ΕΖ)-2 -氮基-2_ (乙基硫基)乙烯基]-2,2-二曱基環丙烷羧酸甲酯,而獲得 下式所示之(1R)_反-3-[(1ΕΖ)-2 -氰基-2-(丁基硫基)乙稀 基]-2,2-二曱基環丙烷羧酸:
淡黃色固體:iH-NMRiCDCIh TMS) δ(ρρπ\): 0.99 to 1.04(m, 3H), 1.25+ 1.26(s+s,3H), 1.36+1.37 (s+s,3H), 1.40 to 1.70(m,4H), 1.79 to 1.83(m,lH), 2.53 to 2.58(m,1H), 2.81 to 2.92(mf2H)f 6.22 to 6.28(m,lH) 參考製造例10 反應係以與參考製造例3相同之方式進行,除了使用 異丙硫醇取代乙硫醇,而獲得下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基-2-(異丙基硫基)乙烯基]-2, 2-二甲基環丙 烷羧酸曱酯: 54 322813 201130418 h3co
ch3 、、ch=c(cn)sch(ch3)2 無色液體:h-NMRiCDCls, TMS) δ(ρριη): 1.23 to 1.39(m, 12H), 1.81 to 1.85(m,lH), 2.51 to 2.62(m,1H), 3.31 to 3.45<m,lH), 3.71+ 3.72(s+s,3H), 6.27 to 6.36(m,lH) 參考製造例11 反應係以與參考製造例4相同之方式進行,除了使用 (1R)-反-3-[(1ΕΖ)-2-氰基-2-(異丙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸曱酯取代(1R)-反-3-[(1ΕΖ)-2-氰基 -2-(乙基硫基)乙烯基]-2, 2-二曱基環丙烷羧酸曱酯,而獲 得下式所示之(1R)_反_3-[(1ΕΖ)-2-氰基-2-(異丙基硫基) 乙烯基]-2,2-二曱基環丙烷羧酸: HX CH,
參考製造例12 將(lR)-4-羥基-6, 6-二甲基-3-氧雜雙環[3. 1. 0]己 -2-酮(1.585g,11.2mmol)、曱基硫基乙腈(1.30g, 14. 9mmol)及碳酸鉀(1. 85g,13. 4mmol)加入至 N,N-二甲基 甲醯胺(15mL)中,隨後於20°C攪拌48小時。將反應混合 物加入冰水(50mL)中,並且以乙酸乙酯(50mL)萃取此溶液。 55 322813 201130418 於獲得之水層中加入5%鹽酸直到pH變成2,接著將水層以 乙酸乙酯萃取2次(每次60ml)。將獲得之乙酸乙自旨層合併, 以飽和鹽水(50mL)清洗1次,接著以硫酸鎮脫水。於減壓 下將有機層濃縮後,獲得2. 30g下式所示之2~(Xis,5R)-6, 6-二曱基-4-侧氧基-3-氧雜雙環[3. 1.0]己~2-基)-2-(曱基硫基)乙腈:
淡黃色液體:W-NMIMCDClh TMS) δ(ρρπ〇: 1.22 to 1.31(m, 1.4 4 (m, 1H), 1.77(m, 1H), 2.35(s, 1.5H), 2.38(s, 1.5H), 3.60(d, 〇.5H), 3.64(d, 0.5H), 4.23{m, 0.5H), 4.33(m, 0.5H) 調配例如下所示。份(parts)係係以質量計。 調配例1 將各20份之本發明化合物(1)至(8)分別溶解於65份 二甲苯中,於其中加入15份之S0LP0L 3005XCTOHO Chemical Industry Co.,Ltd·之註冊商標),並藉由攪拌 而徹底地混合,以獲得可乳化濃縮物。 調配例2 將5份的SORPOL 3005X分別加入各40份之本發明化 合物(1)至(8)中,將此混合物徹底混合,並將32份之 CARPLEX#80(合成的水合氧化矽,SHI0N0GI & CO.,LTD. 之註冊商標)及23份之300-網目矽藻土加入其中,隨後藉 56 322813 201130418 由混合機攪拌而混合以獲得可濕性粉末。 調配例3 將各1. 5份之本發明化合物(1)至(8)、1份之T0KUSIL GUN(合成的水合氧化石夕,由Tokuyama Corporation製造)、 2份之REAX 85A(木質素續酸鈉,由West Vaco Chemicals 製造)、30 份之 BENTONITE FUJI(膨土,由 Houjun 製造) 及65.5份之SHOUKOUZANAclay(高屬土,由Shoukouzan Kougyousho製造)的混合物徹底研磨及混合,並將水加入 其中。將混合物徹底捏合’藉由擠壓造粒機進行造粒,接 著乾燥而獲得1. 5%顆粒。· 調配例4 於各10份之本發明化合物(1)至(8)、1〇份之苯基二 曱苯基乙烷及0· 5份之SUMIDUR L-75(二異氰酸伸甲苯醋 (tolylene diisocyanate),由 Sumitomo Bayer Urethane
Co·,Ltd.製造)的混合物中加入20份之1 〇%阿拉伯膠水溶 液,並將混合物以均質混合機攪拌,而獲得具有平均粒徑 為20 之乳劑。於乳劑中加入2份之乙二醇,並於溫度 6〇°C之溫浴中將混合物進一步攪拌24小時而獲得微膠囊 楽:。另一方面’將0. 2份之三仙膠及1. 〇之份veeguM R(石夕 酸鎮紹’由 Sanyo Chemical Industries, Ltd.所製造)分 散於56. 3份之離子交換水中以獲得增稠劑溶液。接著,將 42. 5份之上述微膠囊漿與57· 5份之上述増稠劑溶液混合 而獲得微膠囊。 σ 調配例5 322813 57 201130418 將各10份之本發明化合物(1)至(8)與10份之苯基二 甲苯基乙烷的混合物加入至2〇份之ι〇%聚乙二醇水溶液 中’並將此混合物藉由均質混合機攪拌而獲得具有平均粒 徑為3/zra之乳劑。另一方面’將〇. 2份之三仙膠及1. 〇 伤之 VEEGUMR(石夕酸鎮|呂’由 Sanyo Chemical Industries, Ltd.製造)分散於58. 8份之離子交換水中以獲得增稠劑溶 液。接著,將40份之上述乳劑溶液與6〇份之上述之增稠 劑溶液混合而獲得可流動性製劑。 調配例6 於各5份之本發明化合物(1)至(8)中,加入3份之 CAKPLEX #80(合成的水合氧化石夕’SHI圆GI &⑺,ltd 之註冊商標)、G. 3份之PAP(磷酸單異㈣與魏二異丙醋 之混合物)及91· 7份之滑石⑽網目),並將混合物以混 合機攪拌以獲得粉劑。 調配例7 將各〇. 1份之本發明化合物⑴至⑻溶解於1〇份之 二氣曱烧中’並將此溶液與89 9份之脫臭煤油 (deodorized ker0Sine)混合而獲得油溶液。 調配例8 調配例9 將各〇.1份之本發明化合物⑴至⑻及39·9份之脫 臭煤油混合並溶解,將此叫填充至喷中並安裝闕 門部分。接著,在加壓下藉由閥^分將6〇份之推進劑(液 化石油氣)填充於其中而獲得油性喷霧製劑。 322813 58 201130418 將各0.6份之本發明化合物(1)至(8)、5份之二甲苯、 3_ 4份之脫臭煤油及1份之Re〇d〇1 M〇_6〇(乳化劑,κ&〇 C〇n>oration之註冊商標)混合並溶解,並將此溶液與5〇 份之水填充至噴霧容器中,接著,在加壓下藉由閥門部分 將40份之推進劑(液化石油氣)填充於其中,而獲得水性噴 霧製劑。 調配例10 將各0. 3g之本發明化合物(1)至(8)溶解於2〇ml之丙 酮中,並藉由攪拌將此溶液與99. 7g用於線圈(c〇il)(藉由 以4 . 3 · 3之比例混合捬粉(Tabu p〇wder)、除蟲菊精榨渣 及木質粉末而得)之基底材料均勻地混合。接著,於其中加 入100ml的水,並將混合物徹底捏合,經乾燥及成型後獲 得殺蟲線圈。 調配例11 將各0.8g之本發明化合物(1)至(8)與〇.4§之向曰葵 基丁氧化物(piperonyl butoxide)的混合物溶解於丙酮 中,並將總體積調整至10ml。接著,使〇.5ml之此溶液均 勻地浸透用於電熱殺蟲片之基底材料(將棉絨與木漿之混 合物的纖維硬化而得之板)中,其具有2. 5cmxl. 5cm之尺寸 及0. 3cm之厚度,而獲得電熱殺蟲片。 調配例12 將各3份之本發明化合物(1)至(8)溶解於份之脫 臭煤油中以獲得溶液’將此溶液倒入由氣乙烯所製造之容 器中。將其上部可藉由加熱器加熱之液體吸收芯(無機研磨 322813 59 201130418 粉末以黏結劑硬化並經燒結)插入該容器中,而獲得用於液 體吸收芯型熱蒸散裝置之零件。 調配例13 將各lOOmg之本發明化合物(1)至(8)溶解於適當量之 丙酮中’並使該溶液浸透具有4. 〇cmx4. Ocm尺寸及1.2cm 厚度之多孔陶瓷板而獲得熱煙燦劑。 製劑例14 將各100/zg之本發明化合物(丨)至(8)溶解於適當量 之丙酮中’並將此溶液均勻地塗佈在具有2cmx2cm尺寸及 0.3mm厚度之濾紙上,經風乾以移除丙酮,藉此獲得在室 溫使用之揮發劑。 調配例15 將各10份之本發明化合物(1)至(8)、35份之含有5〇 份聚氧乙烯烧基醚硫酸銨鹽(p〇ly〇xyethylene alkyl ether sulfate ammonium salt)的白碳與 55 份之水混合, 接著藉由濕式研磨法精細地研磨,而獲得1〇%製劑。 下列試驗例係說明本發明之化合物可有效作為害蟲 防治劑之活性成分。 試驗例1 將各0. 1份之本發明化合物(丨)、(2)及(4)溶解於1〇 份之異丙醇中,並將此溶液與89. 9份之脫臭煤油混合而製 備0· l%(w/v)油溶液。 將六隻美國蟑螂成蟲(美洲蜚蠊,3隻雄性及3隻雌性) 釋放至試驗容器(直徑12 5cm,1〇C[n高,底面係由16網目 60 322813 201130418 金屬線所製成)中,該容器之内面塗佈有奶油,並且將此容 器放置於測試箱(底面:46cmx46cm,高度:70cm)之底部。 使用噴搶在高於容器之上表面60cm處以0. 4kg/cm2之壓力 噴灑各1. 5ml之本發明化合物(1)、(2)及(4)的油溶液。在 喷麗後30秒,將容器從箱中拉出。在預定時間後,計算被 消滅的蟑螂數目並決定消滅比例(重複2次)。消滅比例係 經由下列方程式計算。 消滅比例(%) = (被消滅的蟑螂數目/測試的蟑螂數目)xl〇〇 用以對照之試驗係以與上述同樣之方式進行,除了使 用下式所示之(1R)-順-3-((Z)-2-氰基-2-曱氧基乙烯 基)-2, 2-二甲基環丙烷羧酸2, 5-二側氧基-3-(2-丙炔基) 咪唑啶基曱酯(於JP-A-60-16962中所描述之化合物,以下 稱為比較化合物(1)):
以及下式所示之(1R)-反-3-(2-曱基-1-丙烯基)-2, 2-二甲基環丙烷羧酸3-曱基-5-側氧基-4-(2-丙快基)-4,5-二氫-[1,2,4]三唑基曱酯(於川_八_57_158765中所描 述之化合物’以下稱為比較化合物(2)):
61 322813 0 201130418 結果(喷灑後2分鐘)如表1所示。 表1 試驗化合物 喷灑後2分鐘之消滅比例(°/〇) 本發明化合物(1) 100 本發明化合物(2) 92 本發明化合物(4) 100 比較化合物(1) 42 比較化合物(2) 33 試驗例2 將各0. 025份之本發明化合物(1)及(4)溶解於10份 之異丙醇中,並將此溶液與89. 975份之脫臭煤油混合以製 備0. 025%(w/v)油溶液。 將10隻常見熱帶家蚊(淡色庫蚊)之雌性成蟲釋放至 每一邊為70cm之方形玻璃箱中。使用喷搶將本發明化合物 (1)及(4)之油溶液以0. 9 kg/cm2之壓力由箱子側邊之小窗 喷灑至箱中。在喷灑後1分鐘,計算被消滅的蚊子數目並 決定消滅比例。消滅比例係經由下列方程式計算。 消滅比例(%)=(被消滅的蚊子數目/測試的蚊子數目)xl〇〇 結果如表2所示。 表2 試驗化合物 喷灑後1分鐘之消滅比例(%) 本發明化合物(1) 95 本發明化合物(4) 100 試驗例3 62 322813 201130418 將各0. 025份之本發明化合物(丨)及溶解於1〇份 之異丙醇中,並將此溶液與89. 9975份之脫臭煤油混合7以 製備0. 025%(w/v)油溶液。 ° 將ίο隻蒼蠅(家蠅)成蟲釋放至每一邊為7〇cm之方形 玻璃箱中’使用喷搶將各0. 7ml之本發明化合物(丨)及 的油溶液以0.9kg/cm2之壓力由箱子侧邊之小窗喷濃至箱 中。在喷灑後5分鐘,計算被消滅的蒼蠅數目並決定消滅 比例。消滅比例係經由下列方程式計算。 消滅比例(%)=(被消滅的蒼蠅數目/測試的蒼罐數目)χ1〇〇 結果如表3所示。 表3 試驗化合物 喷灑後5分鐘之消滅比例 本發明化合物(1) 80 ~~— 本發明化合物(4) 80 ~- 試驗例4 將1份之本發明化合物(1)溶解於1〇份之異丙醇中, 並將此溶液與89份之脫臭煤油混合以製備i%(w/v)油溶 液0 將10隻常見熱帶家蚊(淡色庫蚊)之雌性成蟲釋放至 測試容器(底部直徑1 〇. 5cm ’ 7cm高,650m 1)中,並且此杯 狀物之頂部以網子覆蓋。將此杯狀物放置於測試箱(底面: 46cmx46cm,高:70cm)之底部。使用噴搶在高於杯狀物之 上表面30cm處以0. 4kg/cm2之壓力喷灑〇. 5ml之本發明化 合物(1)的油溶液。喷灑後立即將杯狀物從測試箱拉出。在 63 322813 201130418 喷麗後2分鐘,計算被消滅的蚊子數目並決定消滅比例。 試驗例5 將1份之本發明化合物(1)溶解於1〇份之異丙醇中 並將此溶液與89份之脫臭煤油混合以製備i%(w/v)油溶 液0 將10隻蒼绳(家繩)成蟲釋放至測試容器(底部直徑 l〇.5cm,7cm高,650ml)中,並且此杯狀物之頂部以網子 覆蓋。將此杯狀物放置於測試箱(底面:46cmx46cm,高: 70cm)之底部。使用喷槍在高於杯狀物之上表面go cm處以 0· 4kg/cm2之壓力喷灑0. 5ml之本發明化合物(i)的油溶 液。喷灑後立即將杯狀物從測試箱拉出。在喷灑後2分鐘, 計算被消滅的蚊子數目並決定消滅比例。 試驗例6 將1份之本發明化合物(1)溶解於10份之異丙醇中, 並將此溶液與89份之脫臭煤油混合以製備0. l%(w/v)油溶 液。 將6隻美國蟑螂(黑胸大蠊,3隻雄性及3隻雌性)成 蟲釋放至測試容器(直徑12. 5cm,10cm高,底面係由16 網目金屬線所製成)中,該容器之内面塗佈有奶油,並將此 容器放置於測試箱(底面:46cmx46cm,高度:70cm)之底部。 使用喷搶在高於容器之上表面60cm處,以0· 4kg/cm2之壓 力喷灑1.5 ml之本發明化合物(1)的油溶液。在喷灑後30 秒,將容器從箱中拉出。在喷灑後1分鐘,計算被消滅的 蟑螂數目並決定消滅比例(重複2次)。 322813 201130418 試驗例7 將0. 1份之本發明化合物(1)、(2)及(4)溶解於ι〇份 之異丙醇中,並將此溶液與89. 9份之脫臭煤油混合以製備 0. l%(w/v)油溶液。 將6隻美國蟑螂(美洲蜚蠊,3隻雄性及3隻雌性)成 蟲釋放至測試容器(直徑12. 5cm,10cm高,底面係由16 網目金屬線所製成)中,該容器之内面塗佈有奶油,並且將 此谷器放置於測試箱(底面:46cmx46cm,高度:70cm)之底 部。使用喷搶在高於容器之上表面6〇cm處,以〇. 4kg/cm2 之壓力喷灑各1.5ml之本發明化合物(1)、(2)及(4)的油溶 液。在喷灑後30秒,將容器從箱中拉出。在喷灑後3分鐘, 計算被消滅的蟑螂數目並決定消滅比例(重複2次)。消滅 比例係經由下列方程式計算。 消滅比例(% )=(被消滅的蟑螂數目/測試的蟑螂數目)X1 〇 0 結果(噴灑後3分鐘)如表4所示。 表4 試驗化合物 -— 喷灑後3分鐘之消滅比例(%) 本發明化合物 100 本發明化合物 100 本發明化合物(4 ) 100 試驗例8 將各0· 00625份之本發明化合物(1)、(2)、(3)、(4) 及(5),谷解於10份之異丙醇中,並將此溶液與89. 99375 份之脫臭煤油混合以製備〇 〇〇625%(w/v)油溶液。 65 322813 201130418 將10隻德國蟑螂(德國斐蠊,5隻雄性及5隻雌性) 成蟲釋放至測試容器(直徑8. 75cm,7.5cm高,底面係由 16網目金屬線所製成)中,該容器之内面塗佈有奶油,並 且將此容器放置於測試箱(底面:46cmx46cm,高度:70cm) 之底部。 使用喷槍在高於容器之上表面60cm處,以0.4kg/cm2 之壓力喷灑各1.5ml之本發明化合物(1)、(2)、(3)、(4) 及(5)的油溶液。在喷灑後30秒,將容器從箱中拉出。在 喷灑後2分鐘,計算被消滅的蟑螂數目並決定消滅比例(重 複1次)。消滅比例係經由下列方程式計算。 消滅比例(%) = (被消滅的蟑螂數目/測試的蟑螂數目)χ100 結果(喷灑後2分鐘)如表5所示。 表5 試驗化合物 喷灑後2分鐘之消滅比例(°/〇) 本發明化合物(1) 100 本發明化合物(2) 100 本發明化合物(3) 100 本發明化合物(4) 100 本發明化合物(5) 90 (產業利用性) 本發明之化合物具有極佳之害蟲防治效果,而適用於 作為害蟲防治劑之活性成分。 【圖式簡單說明】無 【主要元件符號說明】無 66 322813
Claims (1)
- 201130418 七、申凊專利範圍: 1. 一種式(1)所示之酯化合物:CH=C(CN)SR1 (1 ) 2. 如申請專利範圍第1項所述之酯化合物,其中,於式⑴ 中,在該環丙烷環之1-位置的取代基與在該環丙烷環 之3-位置的取代基之相對構型為反式構型。 3. 如申清專利範圍第1項所述之酯化合物,其中,於式(1) 中,垓%丙燒環之丨_位置的絕對構型為r構型。 4. 如申請專利範圍第1項所述之酯化合物,其中,於式G) 中,該環丙烷環之1-位置的絕對構型為R構型,以及 在該環丙烷環之1-位置的取代基與在環丙烷環之3_位 置的取代基之相對構型為反式構型。 5·如申請專利範圍第!至4項中任一項所述之醋化合物, 其中,於式(1)中,在該環丙烷環之位置的取代基之 雙鍵為e構型或E構型與z構型之混合物,且該Ε ς型 之比例為50%或以上者。 6·如申請專利範圍第1至4項中任一項所述之g旨化合物, 其中,於式(1)中,在該環丙烷環之位置的取 雙鍵為E構型。 7·如申請專利範圍第1至4項中任-項所述之g旨化合物, 1 322813 201130418 其中,於式(1)中,R1為曱基。 8·如申請專利範圍第1至4項中任一項所述之酯化合物, 其中,於式(1)中,R1為乙基。 9.如申請專利範圍第5項所述之酯化合物,其中,於式(1) 中,R1為曱基。 .如申5青專利範圍第5項所述之g旨化合物,其中,於式(1 ) 中,R1為乙基。 .如申明專利範圍第6項所述之g旨化合物,其中,於式(1) 中,R1為甲基。 如申》青專利範圍第6項所述之醋化合物,其中,於式(1) 中,R1為乙基。 I3· 一種害蟲防治劑,係包含申請專利範圍第丨至12項中 任一項所述之酯化合物以及惰性載劑。 一種防治害蟲之方法,係包含將有效量之申請專利範圍 第1至12項中任一項所述之酯化合物施加於害蟲或害 蟲樓息處之步驟。 15·—種防治害紅方法,係包含料效4之”專利範圍 第1至12項中任一項所述之酯化合物施加於蟑螂或蟑 螂棲息處之步驟。 I6·如申請專利範圍第15項所述之防治害蟲之方法,其 中’該蜂鄉為美洲蟑鄉。 、 17·如申請專利範圍第15項所述之防治害蟲之方法,其 中’該蟑螂為德國蟑螂。 種防治害蟲之方法,係包含將有效量之申請專利範圍 322813 2 201130418 第1至12項中任一項所述之酯化合物喷灑於蟑螂或蟑 螂棲息處之步驟。 19. 如申請專利範圍第18項所述之防治害蟲之方法,其中, 該蟑螂為美洲蟑螂。 20. 如申請專利範圍第18項所述之防治害蟲之方法,其中, 該蟑螂為德國蟑螂。 322813 « 201130418 四、指定代表圖:本案無圖式 (一) 本案指定代表圖為:第()圖。 (二) 本代表圖之元件符號簡單說明: 五、本案若有化學式時,請揭示最能顯示發明特徵的化學式:322813 $T〇0105598 號專利 I 100年5月23 5修正替換¥ j 201130418 t . 選擇。 在反應完成後,反應混合物通常會進行後續處理,舉 例而言,將反應混合物過濾,接著將濾液濃縮,或者將反 應混合物倒入水中並將所獲得之溶液以有機溶劑萃取後再 濃縮,如此可獲得本發明之化合物。所獲得之本發明化合 物可藉由例如層析法之操作而純化。 (製造方法2) 〇 ,m " 式u—1)所示之化合物(其中 ί = 代基與在環㈣之3-位置的 造代基之相對_為順式構型)可藉由下列所示之方法製 造 式(1~1);中R表示與上述相同之意思。 4去為將式⑷所示⑽旨化合物:其中尺1表示與上述相同之 , (4) ’、式(5)M化合物錢麵下反應: 322813修正版 13 (5) (5)201130418此反應通常在驗存在下於溶劑中進行。此反應所使用 之溶劑之實例包括鲖類諸如丙酮、曱基乙基酮及曱基異丁 基酮;醚類諸如四氫呋喃;函化烴類諸如氯仿、二氯甲烷、 1,2-二氣乙烷及氯苯;醯胺類諸如n,N-二甲基甲醯胺;亞 砜類諸如二曱基亞颯;此等溶劑之混合物等。 此反應所使用之鹼之實例包括碳酸鹽類諸如碳酸鈉、 碳酸鉀及碳酸鉋。 此反應之反應時間通常在5分鐘至72小時之範圍内。 此反應之反應溫度通常在-20°C至lOOt之範圍内(由 -20°C至溶劑之沸點,若所使用之溶劑的沸點低於100¾), 並且較佳為-5°C至100°C (由-5°C至溶劑之彿點,若所使用 之溶劑的沸點低於100°C)。 在此反應中,式(4)所示内酯化合物相對於式(5)所示 化合物所使用之莫耳比例可任意設定,並且較佳為等莫耳 比例或接近等莫耳比例。 以1 mol之式(4)所示内酿化合物為基準計,驗通常 可在0. 25 mol至過量之範圍内以任意比例使用,並且較佳 為 0.5 mol 至 2 mol 。 在反應完成後,反應混合物通常會進行後續處理,舉 例而言,將反應混合物過濾’接著將濾液濃縮’或者將反 14 322813 201130418h-NMRiCDClhTMS) δ (ppm) : 1.20+1.21 (s+s, 3H) , 1 · 32 + 1.34 (s+s, 3H), 1.79 to 1.82('d,lH), 2.35(s,3H), 2.37(m,lH), 2.40+2.46 (s+s, 3H), 2.49 to 2.53(m,1H), 4.44(d,2H,2.4Hz), 5.67to5.82(m,2H), 6.13 (d,0.5H,J = 10.0 Hz), 6.17{d,0.5H, J =10.0 Hz) 製造例2 fl 將製造例1所得之(1R)-反-3-[(lEZ)-2-氰基_2-(曱 基硫基)乙烯基]-2, 2-二甲基環丙烷羧酸3-甲基-5-側氧 基-4-(2-丙炔基)-4, 5-二氫-[1,2, 4]三唑基甲酯藉由矽膠 管柱層析法(洗提液:己烧/乙酸乙S旨==2 : 1)純化為E異構 物及Z異構物,而獲得呈具有較高極性區分(fraction)的 下式所示之(1R) -反- 3- [(1Ε)-2 -氰基-2-(曱基硫基)乙稀 基]-2, 2-二曱基環丙烷羧酸3-曱基-5-侧氧基-4-(2-丙炔 0 基)-4, 5-二氫-[1,2, 4]三唑基曱酯(以下稱為本發明之化 合物(2)): 43 322813 第10〇i〇5598號專利申請案 100年5月23日修正替^百 201130418白色結晶,熔點為104·0至105.0°C:1H-NMR(CDCl3,TMS>δ(pPIn):1.21 (s,3H), 1.34(s,3H), 1.81(d,lH, J=5.2Hz), 2.35(s,3H},2.37 (mflH), 2.40(s,3H), 2.49 to 2.53(dd,1H), 4.44(d,2H,2.8Hz)f 5.75(dd,2H), 6.13(d,lH,J=l〇.〇Hz) 製造例3 操作係以與製造例1相同之方式進行’但使用(1R)-反-3-[(1ΕΖ)-2-氰基-2-(乙基硫基)乙烯基]-2, 2-二甲基 環丙烷羧酸取代(1R)—反-3_[(1EZ)_2_氰基(甲基硫基) 乙烯基]-2, 2-二甲基環丙炫羧酸,而獲得下式所示之(1R)-反-3-[(1ΕΖ)-2-氰基-2-(乙基硫基)乙烯基]—2, 2-二甲基 環丙炫竣酸3-曱基-5-侧氧基(2_丙炔基)~4, 5-二氫 -[1,2,4]三唑基曱酯(£:2=50:50)(以下稱為本發明之化 合物(3)):44 322813修正版 201130418 --_ • 第100105598號專利申請案 100年5月23日修正替梭‘ 將各0. 025份之本發明化合物(1)及(4)溶解於份 之異丙醇中,並將此溶液與89. 975份之脫臭煤油混合以製 備0. 025%(w/v)油溶液。 將10隻倉繩(豕繩)成蟲釋放至每一邊為70cm之方形 玻璃箱中’使用喷搶將各〇· 7ml之本發明化合物(1)及(4) 的油溶液以0. 9kg/cm2之壓力由箱子侧邊之小窗喷麗至箱 中。在喷灑後5分鐘’計算被消滅的蒼蠅數目並決定消滅 比例。消滅比例係經由下列方程式計算。 〇 、 消滅比例(%) =(被消滅的蒼蠅數目/測試的蒼蠅數目〉χ1〇〇 結果如表3所示。 表3 试驗化合物 喷灑後5分鐘之消滅比例(%) 本發明化合物Π) 80 本發明化合物(4) 80 試驗例4 將1份之本發明化合物(1)溶解於10份之異丙醇令, 並將此溶液與89份之脫臭煤油混合以製備1%(W/V)油溶 液。 將10隻常見熱帶家蚊(淡色庫蚊)之雌性成蟲釋放至 測試容器(底部直徑10.5cm,7cm高,650ml)中,並且此杯 狀物之頂部以網子覆蓋。將此杯狀物放置於測試箱(底面: 46cmx46cm,高:7〇cm)之底部。使用喷槍在高於杯狀物之 上表面30cm處以〇· 4kg/cm2之壓力喷灑〇· 5ml之本發明化 合物(1)的油溶液。喷灑後立即將杯狀物從測試箱拉出。在 63 322813修正版 第100Ϊ05598號專利申請案 100年5月23日修正替換頁 201130418 噴灑後2分鐘,計算被消滅的蚊子數目並決定消滅比例。 試驗例5 將1份之本發明化合物(1)溶解於ίο份之異丙醇中, 並將此溶液與89份之脫臭煤油混合以製備l%(w/v)油溶 液0 將10隻蒼蠅(家蠅)成蟲釋放至測試容器(底部直徑 10. 5cm,7cm高,650ml)中’並且此杯狀物之頂部以網子 覆蓋。將此杯狀物放置於測试箱(底面:46cDix46cm,高: 70cm)之底部。使用喷槍在高於杯狀物之上表面30 cm處以 0· 4kg/cm2之壓力喷灑〇. 5ml之本發明化合物(1)的油溶 液。喷灑後立即將杯狀物從測試箱拉出。在喷麗後2分鐘, 計算被消滅的蒼蠅數目並決定消滅比例。 試驗例6 將1份之本發明化合物(1)溶解於10份之異丙醇中, 並將此溶液與89份之脫臭煤油混合以製備1 %(w/v)油溶 液。 將6隻美國蟑螂(黑胸大蠊,3隻雄性及3隻雌性)成 蟲釋放至測試容器(直徑12. 5cm,10cm高,底面係由16 網目金屬線所製成)中,該容器之内面塗佈有奶油,並將此 谷器放置於測試箱(底面:46cmx46cm,高度:70cm)之底部。 使用喷槍在咼於容器之上表面6〇cm處’以〇.4kg/cm2之壓 力喷灑1 · 5 ml之本發明化合物(1)的油溶液。在喷麗後3〇 秒,將容器從箱中拉出。在喷灑後1分鐘,計算被消滅的 蟑螂數目並決定消滅比例(重複2次)。 322813修正版
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