CN108368064B - 1,2,3-三唑衍生物和包含这种衍生物作为活性成分的杀虫剂和杀螨剂 - Google Patents
1,2,3-三唑衍生物和包含这种衍生物作为活性成分的杀虫剂和杀螨剂 Download PDFInfo
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- CN108368064B CN108368064B CN201680069923.XA CN201680069923A CN108368064B CN 108368064 B CN108368064 B CN 108368064B CN 201680069923 A CN201680069923 A CN 201680069923A CN 108368064 B CN108368064 B CN 108368064B
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- 238000002844 melting Methods 0.000 description 24
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- 238000004519 manufacturing process Methods 0.000 description 1
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- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
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- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical compound O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
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- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
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- YNFMRVVYUVPIAN-AQUURSMBSA-N nemadectin Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C(C)C)O[C@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 YNFMRVVYUVPIAN-AQUURSMBSA-N 0.000 description 1
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- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
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- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- NZYOAGBNMCVQIV-UHFFFAOYSA-N sodium;chloro-(4-methylphenyl)sulfonylazanide;trihydrate Chemical compound O.O.O.[Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 NZYOAGBNMCVQIV-UHFFFAOYSA-N 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 238000012916 structural analysis Methods 0.000 description 1
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- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 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
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 150000004897 thiazines Chemical class 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
- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- IJVXAQIUNIZAHQ-UHFFFAOYSA-N trimethyl-[2-[4-(trifluoromethyl)pyridin-2-yl]ethynyl]silane Chemical compound C[Si](C)(C)C#CC1=CC(C(F)(F)F)=CC=N1 IJVXAQIUNIZAHQ-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XPHOBMULWMGEBA-VZFHVOOUSA-N valienamine Chemical compound N[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O XPHOBMULWMGEBA-VZFHVOOUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-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
- 230000003612 virological effect Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
Description
技术领域
本发明涉及一种新型的1,2,3-三唑衍生物和包含这种衍生物作为活性成分的杀虫剂和杀螨剂。
背景技术
迄今为止,在农业/园艺领域,杀虫剂和杀螨剂在实践中被用于控制各种害虫。然而,传统的通用杀虫剂或杀螨剂在功效、范围和药效残留等方面并不总能让人满意。同时,社会对于减少杀虫剂和杀螨剂的施用量和施用率的需求也未得到充分满足。
此外,害虫对传统的通用杀虫剂或杀螨剂的抗性增强也成为了一个问题。例如,在蔬菜、果树、观赏花卉、茶、小麦/大麦等的栽培中,对例如有机磷制剂类(例如杀螟硫磷,马拉硫磷,丙硫磷,敌敌畏(DDVP))、拟除虫菊酯类(例如扑灭司林,氯氰菊酯(cypermerin),氰戊菊酯,三氟氯氰菊酯,苯甲酰脲类(例如二氟脲,氟苯脲(teflubenzuron),氟啶脲(chlorfluazuron))和沙蚕毒素类(例如巴丹,杀虫磺(bensultap))等各种体系的杀虫剂或杀螨剂产生抗性的害虫进行控制变得十分困难。
此外,尽管还存在害虫尚未获得抗性的杀虫剂或杀螨剂(如,有机卤素类农用化学品DDT和BHC,和氯化环状二烯类农用化学品如艾氏剂、狄氏剂、异狄氏剂、七氯与硫丹),但这些从毒性和环境污染等方便来说是不利的。因此,迫切需要开发在对常规通用目的的农业/园艺杀虫剂或杀螨剂已经获得抗性的多种害虫上以小剂量就呈现足够控制效果的新的杀虫剂或杀螨剂。
关于具有杀虫/杀螨活性的1,2,3-三唑衍生物,专利文献1描述了一种对多种害虫具有杀虫或杀螨活性的1,2,3-三唑衍生物,但是并没有公开本发明所述的1,2,3-三唑衍生物。除此之外,尽管在专利文献2-18中记载了与本发明类似的化合物,但是完全没有描述本发明中的1,2,3-三唑衍生物,在其中1,2,3-三唑衍生物在1位上取代以2-烷硫基、2-烷基亚磺酰基或2-烷基磺酰基,或取代以可被其他取代基取代的苯基。
<引用列表>
[专利文献]
专利文献1:WO2011/113756
专利文献2:WO2015/144895
专利文献3:WO2015/144826
专利文献4:WO2015/068719
专利文献5:JP-A-2015-003906
专利文献6:WO2015/002211
专利文献7:WO2015/000715
专利文献8:WO2014/157600
专利文献9:WO2014/148451
专利文献10:WO2014/142292
专利文献11:WO2014/132972
专利文献12:WO2014/132971
专利文献13:WO2014/123206
专利文献14:WO2014/123205
专利文献15:WO2014/104407
专利文献16:WO2014/021468
专利文献17:WO2014/002754
专利文献18:WO2013/191188
发明内容
本发明要解决的问题
本发明的目的是提供一种新颖的1,2,3-三唑衍生物和含有这种1,2,3-三唑衍生物的杀虫剂或杀螨剂。
解决问题的手段
在为完成上述目的进行大量的深入研究后,本发明的发明人已经发现下式(1)表示的1,2,3-三唑衍生物具有杀虫或杀螨的活性,并完成了本发明。
因此,本申请的第一个方面是由下式(1)表示的1,2,3-三唑衍生物(在本说明书中有时称为“本发明化合物”),第二个方面涉及特征为包含由式(1)表示的1,2,3-三唑衍生物作为活性成分的杀虫剂或杀螨剂。
更具体地,本发明的发明人已经发现,以上所列问题可以通过下述配置解决。
<1>下式(1)表示的1,2,3-三唑衍生物:
[式1]
其中,在式(1)中:
R表示C1-C6烷基或C1-C6卤代烷基;
n表示0-2的整数;
W1和W2各自独立的表示CH或氮原子;
X表示氢原子、卤素原子、氰基、硝基、氨基、羟基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、(C1-C6烷氧基)C1-C6氟烷基、C1-C6烷氧基、C1-C6烷基磺酰基氧基、(C1-C6烷氧基)C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6卤代烷基磺酰基氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、五氟硫烷基、可被C1-C6烷基取代的三唑基、可被C1-C6烷基取代的噁二唑基、可被C1-C6烷基取代的四唑基、(可被C1-C6卤代烷基取代的四唑基)C1-C6烷基、可被卤素原子取代的苯甲酰基、可被卤素原子取代的芳基磺酰基、可被卤素原子取代的芳基亚磺酰基、可被卤素原子取代的芳硫基、可被卤素原子取代的芳基氨基、可被卤素原子取代的芳氧基或者可被卤素原子取代的芳基;m代表1到4的整数,当m大于等于2时,各自的X所代表的可以相同也可以不同。
Q代表苯基、吡啶基、噻唑基、喹啉基、苯并噁唑基、苯并噻唑基或苯并咪唑基,它们可被一个或多个基团选自以下的基团取代:卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基和可被卤素原子取代的苯甲酰基;和
Z代表氢原子、卤素原子、氰基、氨基、羧基、氨基甲酰基、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、(C1-C6烷氧基)C1-C6烷基、C1-C6卤烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基氨基、二(C1-C6烷基)氨基、C1-C6烷氧羰基、(C1-C6烷基)羰基氨基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、(C1-C6卤代烷基)羰基氨基、N,N'-二(C1-C6烷基)羰基氨基、可被卤素原子或C1-C6烷基取代的芳基羰基氨基。
<2>根据<1>的1,2,3-三唑衍生物,其中在式(1)中:
R为C1-C6烷基;
W1和W2为CH;
X为氢原子、卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、五氟硫烷基、或可被卤素原子取代的芳基;
Q为苯基或吡啶基,上述各基团可被一个或多个选自以下的基团取代:卤素原子、氰基、硝基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基,和可被卤素原子取代的苯甲酰基;
Z为氢原子、卤素原子、氰基、C1-C6烷基、C3-C6环烷基或C1-C6卤代烷基。
<3>根据<1>的1,2,3-三唑衍生物,其中在式(1)中:
R为乙基;
W1和W2为CH;
X为氢原子、卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、五氟硫烷基、或可被卤素原子取代的芳基;
Q为苯基,其可被一个或多个选自以下的基团取代:卤素原子、氰基、硝基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基和可被卤素原子取代的苯甲酰基;
Z为氢原子、卤素原子或C1-C6烷基。
<4>根据<1>的1,2,3-三唑衍生物,其中在式(1)中:
R为乙基;
W1和W2为CH;
X为氢原子、卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、五氟硫烷基、或可被卤素原子取代的芳基;
Q为吡啶基,其可被一个或多个选自以下的基团取代:卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基和五氟硫烷基;
<5>含有根据<1>到<4>中任一项的1,2,3-三唑衍生物的杀虫剂或杀螨剂。
发明效果
以式(1)表示的新的1,2,3-三唑衍生物提供了优异的杀虫剂效果或杀螨剂效果。
具体实施方式
根据本发明化合物的1,2,3-三唑衍生物、其制备方法和含有该衍生物作为活性成分的杀虫剂或杀螨剂具体描述如下。
在此,在具有氰基的情况中在下文各基团中指明的碳数排除在氰基中的碳。此外,碳数还排除了含羰基基团如C1-C6烷基羰基和(C1-C6)烷氧羰基中的羰基碳。
附带提及地,在式(1)中W1或W2表示CH的情况下,当X键合至W1或W2时,W1或W2中的H原子被X取代。
由R和Z表示的C1-C6烷基可以是直链也可以是有支链的,其实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、1-戊基、异戊基、新戊基、2-戊基、3-戊基、2-甲基丁基、叔戊基和1-己基。
由X表示的可被羟基或氰基取代的C1-C6烷基可以是直链或有支链的,其实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、1-戊基、异戊基、新戊基、2-戊基、3-戊基、2-甲基丁基、叔戊基、1-己基、羟甲基、氰基甲基、2-甲基氰基甲基、2,2-二甲基氰基甲基、2-乙基-2-甲基氰基甲基、2,2-二乙基氰基甲基和2-氰基乙基。
由Z表示的C3-C6环烷基的实例包括环丙基、环丁基、环戊基和环己基。
由X表示的可被氰基取代的C3-C6环烷基的实例包括环丙基、环丁基、环戊基、环己基、1-氰基环丙基和2-氰基环丙基。
由X表示的(C1-C6烷氧基)C1-C6氟烷基的实例包括1-甲氧基-2,2,2-三氟乙基、1-乙氧基-2,2,2-三氟乙基、2-甲氧基-1,1,1,3,3-六氟异丙基,和2-乙氧基-1,1,1,3,3,3-六氟异丙基。
由X和Z表示的C1-C6烷氧基可以是直链或有支链的,其实例包括甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、1-戊氧基、异戊氧基、新戊氧基、2-戊氧基、3-戊氧基,2-甲基丁氧基,叔戊氧基,和己氧基。
由X表示的C1-C6烷基磺酰基氧基可以是直链或有支链的,其实例包括甲磺酰基氧基、乙基磺酰基氧基、丙基磺酰基氧基、异丙基磺酰基氧基、正丁基磺酰基氧基、异丁基磺酰基氧基、仲丁基磺酰基氧基、叔丁基磺酰基氧基、1-戊基磺酰基氧基、异戊基磺酰基氧基、新戊基磺酰基氧基,2-戊基磺酰基氧基,3-戊基磺酰基氧基,2-甲基丁基磺酰基氧基,叔戊基磺酰基氧基,1-己基磺酰基氧基。
由X表示的(C1-C6烷氧基)C1-C6烷氧基可以是直链或有支链的,其实例包括甲氧基甲氧基、甲氧基乙氧基、乙氧基甲氧基、乙氧基乙氧基、甲氧基丙氧基、乙氧基丙氧基、正丙氧基甲氧基、异丙氧基甲氧基、正丁氧基甲氧基、仲丁氧基甲氧基、叔丁氧基甲氧基、1-戊氧基甲氧基和1-己氧基甲氧基。
由Z表示的(C1-C6烷氧基)C1-C6烷基可以是直链或有支链的,其实例包括甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、异丙氧基甲基、正丁氧基甲基、仲丁氧基甲基、叔丁氧基甲基、1-戊氧基甲基和1-己氧基甲基。
由X表示的可被氰基取代的C1-C6卤代烷基可以是直链或有支链的,其实例包括一氟甲基、一氯甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、2-氯乙基、1-氟乙基、2-氟乙基、6-氟己基、七氟异丙基、1,1,1,3,3,3-六氟异丙基和(氰基)二氟甲基。
由R和Z代表的C1-C6卤代烷基可以是直链或有支链的,其实例包括一氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、2-氯乙基、1-氟乙基、2-氟乙基、6-氟己基和七氟异丙基。
由X表示的C1-C6卤代烷氧基的实例包括三氟甲氧基、2,2,2-三氟乙氧基、2-氯乙氧基和1,1,2,2-四氟乙氧基。
由X表示的C1-C6烷基羰基可以是直链或有支链的,其实例包括乙酰基、乙基羰基、正丙基羰基、异丙基羰基、正丁基羰基、异丁基羰基、仲丁基羰基、叔丁基羰基,1-戊基羰基和1-己基羰基。
由X表示的C1-C6卤代烷基磺酰基氧基的实例包括二氟甲磺酰基氧基、三氟甲磺酰基氧基、氯甲磺酰基氧基、三氯甲磺酰基氧基和2-氯乙磺酰基氧基。
由X和Z表示的C1-C6烷硫基可以是直链或有支链的,其实例包括甲硫基、乙硫基、正丙基硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、1-戊硫基、异戊硫基、新戊硫基、2-戊硫基、3-戊硫基、2-甲基丁硫基,叔戊硫基和1-己硫基。
由X表示的C1-C6烷基亚磺酰基可以是直链或有支链的,其实例包括甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、1-戊基亚磺酰基、异戊基亚磺酰基、新戊基亚磺酰基、2-戊基亚磺酰基、3-戊基亚磺酰基、2-甲基丁基亚磺酰基、叔戊基亚磺酰基和1-己基亚磺酰基。
由X表示的C1-C6烷基磺酰基可以是直链或有支链的,其实例包括甲磺酰基、乙磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、1-戊基磺酰基、异戊基磺酰基、新戊基磺酰基、2-戊基磺酰基、3-戊基磺酰基、2-甲基丁基磺酰基、叔戊基磺酰基和1-己基磺酰基。
由X和Z表示的C1-C6卤代烷硫基的实例包括一氟甲硫基、二氟甲硫基、三氟甲硫基、2,2,2-三氟乙硫基和2,2,2-三氯乙硫基。
由X表示的C1-C6卤代烷亚磺酰基的实例包括一氟甲基亚磺酰基、二氟甲基亚磺酰基、三氟甲基亚磺酰基、2,2,2-三氟乙基亚磺酰基和2,2,2-三氯乙基亚磺酰基。
由X表示的C1-C6卤代烷基磺酰基的实例包括一氟甲基磺酰基、二氟甲基磺酰基、三氟甲基磺酰基、2,2,2-三氟乙基磺酰基和2,2,2-三氯乙基磺酰基。
由X和Z表示的C1-C6烷基氨基可以是直链或有支链的,其实例包括甲氨基、乙氨基、异丙氨基、异丁氨基、1-戊氨基和1-己氨基。
由X和Z表示的(C1-C6烷氧基)羰基可以是直链或有支链的,其实例包括甲氧羰基、乙氧羰基、正丙氧羰基、异丙氧基羰基、正丁氧羰基、仲丁氧羰基、叔丁氧基羰基、和正己基氧羰基。
由X和Z表示的二(C1-C6烷基)氨基可以是直链或有支链的,其实例包括二甲氨基、二乙氨基、N-乙基-N'-甲氨基、二(异丙基)氨基、二(正丁基)氨基、二(正戊基)氨基和二(正己基)氨基。
由X和Z表示的(C1-C6烷基)羰基氨基可以是直链或有支链的,其实例包括乙酰氨基、乙基羰基氨基、正丙基羰基氨基、异丙基羰基氨基和叔丁基羰基氨基。
由X表示的(C1-C6烷基)羰基(C1-C6烷基)氨基可以是直链或有支链的,其实例包括N-(甲基)乙酰氨基、N-(乙基)-正丙基羰基氨基、N-(乙基)异丙基羰基氨基和N-(乙基)叔丁基羰基氨基。
由X和Z表示的N-(C1-C6烷基)氨基甲酰基可以是直链或有支链的,其实例包括N-甲氨基甲酰基、N-乙氨基甲酰基、N-(正丙基)氨基甲酰基、N-异丙基氨基甲酰基、N-(n-己基)氨基甲酰基。
由X和Z表示的N,N'-二(C1-C6烷基)氨基甲酰基可以是直链或有支链的,其实例包括N,N'-二甲氨基甲酰基、N,N'-二乙氨基甲酰基、N-乙基-N'-甲基氨基甲酰基和N-乙基-N'-异丙氨基甲酰基。
由X表示的可被C1-C6烷基取代的三唑基可以是直链或有支链的,其实例包括1,2,4-三唑基-3-基、1-甲基-1,2,4-三唑-3-基、1-乙基-1,2,4-三唑-3-基、1-(正丙基)-1,2,4-三唑-3-基和1-异丙基-1,2,4-三唑-3-基。
由X表示的可被C1-C6烷基取代的噁二唑基可以是直链或有支链的,且其实例包括1,2,4-噁二唑-3-基、5-甲基-1,2,4-噁二唑-3-基、5-乙基-1,2,4-噁二唑-3-基、5-(正丙基)-1,2,4-噁二唑-3-基和5-异丙基-1,2,4-噁二唑-3-基。
由X表示的可被C1-C6烷基取代的四唑基可以是直链或有支链的,并且其实例包括四唑-5-基、1-甲基四唑-5-基、1-乙基四唑-5-基、1-(正丙基)-四唑-5-基、1-异丙基四唑-5-基、2-甲基四唑-5-基、2-乙基四唑-5-基、2-(正丙基)-四唑-5-基和2-异丙基四唑-5-基。
由X表示的(可被C1-C6卤代烷基取代的四唑基)C1-C6烷基的实例包括(5-三氟甲基四唑-2-基)甲基和(5-五氟乙基四唑-2-基)甲基。
由X表示的可被卤素原子取代的苯甲酰基的实例包括苯甲酰基、2-氟苯甲酰基、3-氟苯甲酰基、4-氟苯甲酰基、2-氯苯甲酰基、3-氯苯甲酰基、4-氯苯甲酰基、2-溴苯甲酰基、3-溴苯甲酰基、4-溴苯甲酰基、2-碘苯甲酰基、3-碘苯甲酰基、4-碘苯甲酰基、2,4-二氯苯甲酰基、2,6-二氯苯甲酰基、3,4-二氯苯甲酰基和3,5-二氯苯甲酰基。
由X表示的可被卤素原子取代的芳基磺酰基的实例包括苯基磺酰基、2-氟苯基磺酰基、3-氟苯基磺酰基、4-氟苯基磺酰基、2-氯苯基磺酰基、3-氯苯基磺酰基、4-氯苯基磺酰基、2-溴苯基磺酰基、3-溴苯基磺酰基、4-溴苯基磺酰基、2-碘苯基磺酰基、3-碘苯基磺酰基、4-碘苯基磺酰基、2,4-二氯苯基磺酰基、2,6-二氯苯基磺酰基、3,4-二氯苯基磺酰基、3,5-二氯苯基磺酰基、2-吡啶磺酰基、5-氯-2-吡啶磺酰基、5-三氟甲基-2-吡啶磺酰基、3-氯-5-三氟甲基-2-吡啶基磺酰基、3-吡啶磺酰基、6-氯-3-吡啶基磺酰基和4-吡啶基磺酰基。
由X表示的可被卤素原子取代的芳基亚磺酰基的实例包括苯基亚磺酰基、2-氟苯基亚磺酰基、3-氟苯基亚磺酰基、4-氟苯基亚磺酰基、2-氯苯基亚磺酰基、3-氯苯基亚磺酰基、4-氯苯基亚磺酰基、2-溴苯基亚磺酰基、3-溴苯基亚磺酰基、4-溴苯基亚磺酰基、2-碘苯基亚磺酰基、3-碘苯基亚磺酰基、4-碘苯基亚磺酰基、2,4-二氯苯亚磺酰基、2,6-二氯苯亚磺酰基、3,4-二氯苯亚磺酰基、3,5-二氯苯亚磺酰基、2-吡啶亚磺酰基、5-氯-2-吡啶基亚磺酰基、5-三氟甲基-2-吡啶基亚磺酰基、3-氯-5-三氟甲基-2-吡啶基亚磺酰基、3-吡啶基亚磺酰基、6-氯-3-吡啶基亚磺酰基和4-吡啶基亚磺酰基。
由X表示的可被卤素原子取代的芳硫基的实例包括苯硫基、2-氟苯硫基、3-氟苯硫基、4-氟苯硫基、2-氯苯硫基、3-氯苯硫基、4-氯苯硫基、2-溴苯硫基、3-溴苯硫基、4-溴苯硫基、2-碘苯硫基、3-碘苯硫基、4-碘苯硫基、2,4-二氯苯硫基、2,6-二氯苯硫基、3,4-二氯苯硫基、3,5-二氯苯硫基、2-吡啶基硫基、5-氯-2-吡啶基硫基、5-三氟甲基-2-吡啶基硫基、3-氯-5-三氟甲基-2-吡啶基硫基、3-吡啶基硫基、6-氯-3-吡啶基硫基和4-吡啶基硫基。
由X表示的可被卤素原子取代的芳氨基的实例包括苯氨基,2-氟苯氨基、3-氟苯氨基、4-氟苯氨基、2-氯苯氨基、3-氯苯氨基、4-氯苯氨基、2-溴苯氨基、3-溴苯氨基、4-溴苯氨基、2-碘苯氨基、3-碘苯氨基、4-碘苯氨基、2,4-二氯苯基氨基、2,6-二氯苯氨基、3,4-二氯苯氨基、3,5-二氯苯氨基、2-吡啶基氨基、5-氯-2-吡啶基氨基、5-三氟甲基-2-吡啶基氨基、3-氯-5-三氟甲基-2-吡啶基氨基、3-吡啶基氨基、6-氯-3-吡啶基氨基和4-吡啶基氨基。
由X表示的可被卤素原子取代的芳氧基的实例包括苯氧基,2-氟苯氧基、3-氟苯氧基、4-氟苯氧基、2-氯苯氧基、3-氯苯氧基、4-氯苯氧基、2-溴苯氧基、3-溴苯氧基、4-溴苯氧基、2-碘苯氧基、3-碘苯氧基、4-碘苯氧基、2,4-二氯苯氧基、2,6-二氯苯氧基、3,4-二氯苯氧基、3,5-二氯苯氧基、2-吡啶基氧基、5-氯-2-吡啶基氧基、5-三氟甲基-2-吡啶基氧基、3-氯-5-三氟甲基-2-吡啶基氧基、3-吡啶基氧基、6-氯-3-吡啶基氧基和4-吡啶基氧基。
由X表示的可被卤素原子取代的芳基的实例包括苯基,2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-碘苯基、3-碘苯基、4-碘苯基、2,4-二氯苯基、2,6-二氯苯基、3,4-二氯苯基、3,5-二氯苯基、2-吡啶基、5-氯-2-吡啶基、5-三氟甲基-2-吡啶基、3-氯-5-三氟甲基-2-吡啶基、3-吡啶基、6-氯-3-吡啶基和4-吡啶基。
由Z表示的N-(C1-C6卤代烷基)氨基甲酰基的实例包括N-(2,2,2-三氟乙基)氨基甲酰基和N-(3,3,3-三氟丙基)氨基甲酰基。
由Z表示的N,N'-二(C1-C6烷基)羰基氨基可以是直链或支链的,并且其实例包括N,N'-二乙酰氨基、N-乙酰基-N'-乙基羰基氨基、N,N'-二乙基羰基氨基、N-乙酰基-N'-(正丙基)羰基氨基和N-乙酰基-N'-异丙基羰基氨基。
由Z表示的可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基的实例包括N-(苯基)氨基甲酰基、N-(2-氯苯基)氨基甲酰基、N-(3-氯苯基)氨基甲酰基、N-(4-氯苯基)氨基甲酰基、N-(2-甲基苯基)氨基甲酰基、N-(3-甲基苯基)氨基甲酰基和N-(4-甲基苯基)氨基甲酰基。
由Z表示的(C1-C6卤代烷基)羰基氨基的实例包括三氟甲基羰基氨基、(2,2,2-三氟乙基)羰基氨基和(3,3,3-三氟丙基)羰基氨基。
由Z表示的可被卤素原子或C1-C6烷基取代的芳基羰基氨基的实例包括苯甲酰基氨基、2-氯苯甲酰基氨基、3-氯苯甲酰基氨基、4-氯苯甲酰基氨基、2-甲基苯甲酰基氨基、3-甲基苯甲酰基氨基和4-甲基苯甲酰基氨基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的苯基的实例,包括苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-环丙基苯基、3-环丙基苯基、4-环丙基苯基、2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、3-三氟甲氧基苯基、4-氰基苯基、4-苯氧基苯基、2-(三氟甲基)苯基、3-(三氟甲基)苯基、4-(三氟甲基)苯基、3-五氟硫烷基苯基、3,5-二氯苯基、2-氯-4-(三氟甲基)苯基、3-(三氟甲基)-4-氯苯基、3,5-双(三氟甲基)苯基、2,5-双(三氟甲基)苯基、2,4-双(三氟甲基)苯基、3,4-双(三氟甲基)苯基、4-(全氟异丙基)苯基、2-氯-3,5-双(三氟甲基)苯基、2-氟-3,5-双(三氟甲基)苯基、3-氯-5-(三氟甲基)苯基、3-氟-5-(三氟甲基)苯基、3-溴-5-(三氟甲基)苯基、3-甲基-5-(三氟甲基)苯基、3-乙酰基-5-(三氟甲基)苯基、3-三氟乙酰基-5-(三氟甲基)苯基、3-氰基-5-(三氟甲基)苯基、3-氰甲基-5-(三氟甲基)苯基、3-环丙基-5-(三氟甲基)苯基、3-(1-氰基环丙基)-5-(三氟甲基)苯基、3-三氟甲氧基-5-(三氟甲基)苯基、3-甲硫基-5-(三氟甲基)苯基、3-甲基亚磺酰基-5-(三氟甲基)苯基、3-甲基磺酰基-5-(三氟甲基)苯基、3-三氟甲硫基-5-(三氟甲基)苯基、3-甲氧基羰基-5-(三氟甲基)苯基、3-乙氧基羰基-5-(三氟甲基)苯基、3-(甲基氨基甲酰基)-5-(三氟甲基)苯基、3-(N-甲基氨基甲酰基)二氟甲基-5-(三氟甲基)苯基、3-(N-苯基氨基甲酰基)二氟甲基-5-(三氟甲基)苯基、3-苯基氨基羰基-5-(三氟甲基)苯基、3-(2-吡啶基氨基)羰基-5-(三氟甲基)苯基、3-(3-吡啶基氨基)羰基-5-(三氟甲基)苯基、3-(4-吡啶基氨基)羰基-5-(三氟甲基)苯基、3-(叔丁氧基羰基氨基)-5-(三氟甲基)苯基、3-(三氟乙酰基氨基)-5-(三氟甲基)苯基、3-(三氟甲基磺酰基氨基)-5-(三氟甲基)苯基、3-苯基-5-(三氟甲基)苯基、3-苯氧基-5-(三氟甲基)苯基、3-氰基二氟甲基-5-(三氟甲基)苯基、4-叔丁基苯基、4-联苯基、4-氯-3,5-双(三氟甲基)苯基、4-甲基-3,5-双(三氟甲基)苯基、3-{N-(4-氯苯基)氨基甲酰基}-5-(三氟甲基)苯基、3-氨基甲酰基二氟甲基-5-(三氟甲基)苯基、3-三氟甲基-5-(甲基氨基羰基二氟甲基)苯基、3-苯甲酰基-5-(三氟甲基)苯基、3-三氟甲基-5-{(N-苯基氨基甲酰基)二氟甲基}苯基、3-(1,1'-二氟乙基)-5-(三氟甲基)苯基、2-氟-5-(三氟甲基)苯基和3-羧基-5-(三氟甲基)苯基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6-烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的吡啶基的实例,包括2-吡啶基、3-吡啶基、4-吡啶基、6-氯-2-吡啶基、2-氯-3-吡啶基、2-氯-4-吡啶基、6-溴-2-吡啶基、5-溴-3-吡啶基、2-溴-4-吡啶基、6-甲基-2-吡啶基、4-甲基-2-吡啶基、4-氯-2-吡啶基、4-氰基-2-吡啶基、2-甲基-4-吡啶基、2-三氟甲基-4-吡啶基、6-环丙基-3-吡啶基、6-甲氧基-2-吡啶基、6-甲氧基-3-吡啶基、3-三氟甲基-2-吡啶基、4-三氟甲基-2-吡啶基、5-三氟甲基-2-吡啶基、6-三氟甲基-2-吡啶基、4-五氟乙基-2-吡啶基、5-五氟乙基-3-吡啶基、4-五氟硫烷基-2-吡啶基、4,6-双三氟甲基-2-吡啶基、2,5-双三氟甲基-4-吡啶基、3-氯-5-三氟甲基-2-吡啶基、3-氰基-4,6-双三氟甲基-2-吡啶基、3-氯-4-三氟甲基-2-吡啶基、4-三氟甲基-5-氯-2-吡啶基、4-三氟甲基-6-氯-2-吡啶基、4-三氟甲基-3-溴-2-吡啶基、4-三氟甲基-5-溴-2-吡啶基、4-三氟甲基-6-溴-2-吡啶基、3,5-二氯-4-三氟甲基-2-吡啶基、3-氟-4-三氟甲基-2-吡啶基、4-三氟甲基-5-氟-2-吡啶基、4-三氟甲基-6-氟-2-吡啶基、3,5-二氟-4-三氟甲基-2-吡啶基、4-三氟甲基-6-甲氧基-2-吡啶基、4-三氟甲基-6-氰基-2-吡啶基、4-三氟甲基-6-环丙基-2-吡啶基、4-三氟甲基-3-吡啶基、5-三氟甲基-3-吡啶基、6-三氟甲基-3-吡啶基、2-氟-5-三氟甲基-3-吡啶基、3-三氟甲基-4-吡啶基、4-三氟甲氧基-2-吡啶基、5-三氟甲氧基-2-吡啶基、5-甲硫基-2-吡啶基、4-甲硫基-2-吡啶基、5-甲基亚磺酰基-2-吡啶基、4-甲基亚磺酰基-2-吡啶基、5-甲基磺酰基-2-吡啶基、4-甲基磺酰基-2-吡啶基、4-三氟甲硫基-2-吡啶基、4-三氟甲基亚磺酰基-2-吡啶基、4-三氟甲基磺酰基-2-吡啶基、3-N-甲基氨基甲酰基-2-吡啶基、3-N-(2,2,2-三氟乙基)氨基甲酰基-2-吡啶基、3-N,N'-二甲基氨基甲酰基-2-吡啶基、3-甲基磺酰氨基-2-吡啶基、5-三氟甲基磺酰基氨基-2-吡啶基、5-苯基磺酰基氨基-2-吡啶基和5-甲基氨基磺酰基-2-吡啶基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6-烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的噻唑基的实例,包括2-噻唑基、4-甲基噻唑-2-基、4-三氟甲基噻唑-2-基、4-氯噻唑-2-基、4,5-二甲基噻唑-2-基和5-三氟甲基噻唑-2-基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷基{被N-芳基氨基甲酰基(可被卤素原子或C1-C6烷基取代)取代}、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、可被卤素原子取代的苯甲酰基的基团取代的由Q表示的喹啉基的实例,包括2-喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、4-甲基-2-喹啉基、4-三氟甲基-2-喹啉基、8-三氟甲基-2-喹啉基、4-氯-6-喹啉基、4-氰基-8-三氟甲基-6-喹啉基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的苯并噁唑基的实例,包括2-苯并噁唑基、5-甲基苯并噁唑-2-基、5-甲氧基苯并噁唑-2-基、5-氟苯并噁唑-2-基、5-氯苯并噁唑-2-基、5-溴苯并噁唑-2-基、5-三氟甲基苯并噁唑-2-基、6-甲基苯并噁唑-2-基、6-氟苯并噁唑-2-基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的苯并噻唑基的实例,包括2-苯并噻唑基、5-甲基苯并噻唑-2-基、5-甲氧基苯并噻唑-2-基、5-氟苯并噻唑-2-基、5-氯苯并噻唑-2-基、5-溴苯并噻唑-2-基、5-三氟甲基苯并噻唑-2-基、6-三氟甲基苯并噻唑-2-基、6-甲基苯并噻唑-2-基、和6-氟苯并噻唑-2-基。
可被一个或多个选自卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基的基团取代的由Q表示的苯并咪唑基的实例,包括1-甲基-2-苯并咪唑基、1,5-二甲基-2-苯并咪唑基、1-甲基-5-甲氧基-2-苯并咪唑-2-基、1-甲基-5-氯-2-苯并咪唑-2-基、1-甲基-5-溴苯并咪唑-2-基、1-甲基-5-三氟甲基苯并咪唑-2-基、1-甲基-6-三氟甲基苯并咪唑-2-基、1-甲基-6-氯苯并咪唑-2-基和1,6-二甲基-2-苯并咪唑基。
式(1)中的R优选为C1-C6烷基,更优选乙基。
式(1)中的W1和W2更优选为CH。
式(1)中的X优选为氢原子、卤素原子、氰基、羟基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、(C1-C6烷氧基)C1-C6氟烷基、C1-C6烷氧基、(C1-C6烷氧基)C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6卤代烷基磺酰基氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、五氟硫烷基、可被C1-C6烷基取代的三唑基、可被C1-C6烷基取代的噁二唑基、可被C1-C6烷基取代的四唑基、(可被C1-C6卤代烷基取代的四唑基)C1-C6烷基、可被卤素原子取代的苯甲酰基、可被卤素原子取代的芳基磺酰基、可被卤素原子取代的芳基亚磺酰基、可被卤素原子取代的芳硫基、可被卤素原子取代的芳基氨基、可被卤素原子取代的芳基氧基、或可被卤素原子取代的芳基,更优选为氢原子、卤素原子、氰基、羟基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、(C1-C6烷氧基)C1-C6氟烷基、C1-C6烷氧基、(C1-C6烷氧基)C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6卤代烷基磺酰基氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、(C1-C6烷氧基)羰基、N-(C1-C6烷基)氨基甲酰基、五氟硫烷基、可被C1-C6烷基取代的三唑基、可被C1-C6烷基取代的噁二唑基、可被C1-C6烷基取代的四唑基、(可被C1-C6卤代烷基取代的四唑基)C1-C6烷基、可被卤素原子取代的苯甲酰基、可被卤素原子取代的芳基磺酰基、可被卤素原子取代的芳基亚磺酰基、可被卤素原子取代的芳硫基、可被卤素原子取代的芳基氨基、可被卤素原子取代的芳氧基或可被卤素原子取代的芳基,还更优选为氢原子、卤素原子、氰基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷基磺酰基氧基、C1-C6卤代烷硫基、(C1-C6烷氧基)羰基、五氟硫烷基、可被C1-C6烷基取代的三唑基、可被C1-C6烷基取代的噁二唑基、可被C1-C6烷基取代的四唑基或可被卤素原子取代的芳基。
式(1)中的Q优选为苯基或吡啶基,其中每个可被一个或多个选自上述取代基的基团取代;更优选苯基或吡啶基,其中每个可被一个或多个选自以下的基团取代:卤素原子、氰基、硝基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、和可被卤素原子取代的苯甲酰基。
可被一个或多个选自上述取代基的基团取代的苯基优选为可被一个或多个选自以下的基团取代的苯基:卤素原子、氰基、羧基、可被羟基或氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、{被N-氨基甲酰基(其可被C1-C6烷基取代)取代的}C1-C6卤代烷基、{被N-芳基氨基甲酰基(其可被卤素原子或C1-C6烷基取代)取代的}C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基羰基、C1-C6烷基羰基、五氟硫烷基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基、以及可被卤素原子取代的苯甲酰基,更优选为可被一个或多个选自以下基团取代的苯基:卤素原子、氰基、可被氰基取代的C3-C6环烷基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基羰基和五氟硫烷基。
可被一个或多个选自上述取代基的基团取代的吡啶基优选为可被一个或多个选自以下的基团取代的吡啶基:卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基,更优选可被一个或多个选自以下的基团取代的吡啶基:卤素原子、氰基、C1-C6烷氧基和可被氰基取代的C1-C6卤代烷基,并且最优选为可被一个或多个选自以下的基团取代的吡啶基:卤素原子、氰基和可被氰基取代的C1-C6卤代烷基。
式(1)中的Z优选为氢原子、卤素原子、氰基、氨基、羧基、氨基甲酰基、C1-C6烷基、C3-C6环烷基、(C1-C6烷氧基)C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、N-(C1-C6烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、(C1-C6卤代烷基)羰基氨基、N,N'-二(C1-C6烷基)羰基氨基、或可被卤素原子或C1-C6烷基取代的芳基羰基氨基,更优选氢原子、卤素原子、氰基、氨基、羧基、氨基甲酰基、C1-C6烷基、(C1-C6烷氧基)C1-C6烷基、C1-C6烷氧基羰基、N-(C1-C6烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、N,N'-二(C1-C6烷基)氨基甲酰基、(C1-C6卤代烷基)羰基氨基、N,N'-二(C1-C6烷基)羰基氨基、或可被卤素原子或C1-C6烷基取代的芳基羰基氨基,还更优选优选氢原子、卤素原子、氰基、氨基、C1-C6烷基、C1-C6烷氧基羰基或N,N'-二(C1-C6烷基)氨基甲酰基,但仍然更优选为氢原子、卤素原子、氰基、氨基或C1-C6烷基。
顺便提及,在本申请的一个优选实施例中,由式(1)表示的1,2,3-三唑衍生物是由下式(1A)表示的1,2,3-三唑衍生物:
[式2]
在式(1A)中:
R'表示C1-C6烷基或C1-C6卤代烷基;
n表示0至2的整数;
X'表示氢原子、卤素原子、氰基、硝基、氨基、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、N-(C1-C6烷基)氨基甲酰基、或N,N-二(C1-C6烷基)氨基甲酰基;
m表示1至4的整数,并且当m表示2或更大的整数时,各自的X可以相同或不同;
Q'表示苯基或吡啶基,它们各自可被一个或多个选自以下的基团取代:氢原子、卤素原子、氰基、硝基、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(吡啶基)氨基甲酰基、N,N-二(C1-C6烷基)氨基甲酰基、N-(C1-C6烷基羰基)氨基、N-(C1-C6卤代烷基羰基)氨基、N-(C1-C6烷氧基羰基)氨基、N-(C1-C6卤代烷氧基羰基)氨基、氮原子可被C1-C6烷基取代的C1-C6烷基磺酰基氨基、氮原子可被C1-C6烷基取代的C1-C6卤代烷基磺酰基氨基、氮原子可被C1-C6烷基取代并且苯基可被卤素原子或C1-C6烷基取代的苯基磺酰基氨基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、和可被卤素原子或C1-C6烷基取代的苯氧基;
Z'表示氢原子、卤素原子、氰基、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基羰基、N-(C1-C6烷基)氨基甲酰基、N-(C1-C6卤代烷基)氨基甲酰基、可被卤素原子或C1-C6烷基取代的N-(苯基)氨基甲酰基、N,N-二(C1-C6烷基)氨基甲酰基、氨基、C1-C6烷基氨基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、或(C1-C6卤代烷基)羰基氨基。
每个R'基团的实例包括式(1)中对于R所述的那些相应基团。
每个X'基团的实例包括式(1)中对于X所述的那些相应基团。
每个Q'基团的实例包括式(1)中对于Q所述的那些相应基团。
每个Z'基团的实例包括式(1)中对于Z所述的那些相应基团。
由式(1)表示的1,2,3-三唑衍生物的代表性实例一起示于下表1至4中,但是本发明不限于这些化合物。这些化合物包括包含光学异构体、E形和Z形的化合物。
各表中以及本说明书中的以下每一个符号表示下面描述的相应基团。
另外,“Me”代表甲基,“Et”代表乙基,“n-Pr”代表正丙基,“i-Pr”代表异丙基,“c-Pr”代表环丙基,“n-Bu”代表正丁基,“n-Pen”代表正戊基,“tert-Bu”代表叔丁基,“n-Pen”代表正戊基,“n-Hex”代表正己基,“Ac”代表乙酰基,“Ph”代表苯基。
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-1 | Me | 0 | H | H | H | CH | CH | ||
1-2 | Me | 0 | H | 3-CF<sub>3</sub> | H | CH | CH | ||
1-3 | Me | 0 | H | 3-CF<sub>3</sub> | Me | CH | CH | ||
1-4 | Me | 0 | H | 4-CF<sub>3</sub> | H | CH | CH | ||
1-5 | Me | 0 | H | 4-CF<sub>3</sub> | Me | CH | CH | ||
1-6 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-7 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-8 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | F | CH | CH | ||
1-9 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-10 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-11 | Me | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-12 | Me | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-13 | Me | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-14 | Me | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-15 | Me | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-16 | Et | 0 | H | H | H | CH | CH | 淡黄色固体 | 88-90 |
1-17 | Et | 0 | H | H | Me | CH | CH | ||
1-18 | Et | 0 | H | H | Cl | CH | CH | ||
1-19 | Et | 0 | H | H | Br | CH | CH | ||
1-20 | Et | 0 | H | H | I | CH | CH | ||
1-21 | Et | 0 | H | 3-Cl | H | CH | CH | 红褐色油状 | |
1-22 | Et | 0 | H | 4-Cl | H | CH | CH | 无色油状 | |
1-23 | Et | 0 | H | 3-Br | H | CH | CH | 红褐色油状 | |
1-24 | Et | 0 | H | 3-OCF<sub>3</sub> | H | CH | CH | 红褐色油状 | |
1-25 | Et | 0 | H | 2-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
1-26 | Et | 0 | H | 3-CF<sub>3</sub> | H | CH | CH | 褐色油状 | |
1-27 | Et | 0 | H | 3-CF<sub>3</sub> | Me | CH | CH | 红褐色油状 | |
1-28 | Et | 0 | H | 3-CF<sub>3</sub> | Et | CH | CH | 红褐色油状 | |
1-29 | Et | 0 | H | 3-CF<sub>3</sub> | Cl | CH | CH | 黄色固体 | 87-90 |
1-30 | Et | 0 | H | 3-CF<sub>3</sub> | Br | CH | CH | ||
1-31 | Et | 0 | H | 3-CF<sub>3</sub> | I | CH | CH | 白色固体 | 136-139 |
1-32 | Et | 0 | 3-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-33 | Et | 0 | 4-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-34 | Et | 0 | 5-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-35 | Et | 0 | 6-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-36 | Et | 0 | 3-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-37 | Et | 0 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-38 | Et | 0 | 5-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | 黄色油状 | |
1-39 | Et | 0 | 6-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-40 | Et | 0 | H | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 114-115 |
1-41 | Et | 0 | H | 4-CF<sub>3</sub> | Me | CH | CH | ||
1-42 | Et | 0 | H | 4-CF<sub>3</sub> | Cl | CH | CH | ||
1-43 | Et | 0 | H | 4-CF<sub>3</sub> | Br | CH | CH | ||
1-44 | Et | 0 | H | 4-CF<sub>3</sub> | I | CH | CH | ||
1-45 | Et | 0 | 3-Cl | 4-CF<sub>3</sub> | H | CH | CH |
[表1-2]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-46 | Et | 0 | 4-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-47 | Et | 0 | 5-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-48 | Et | 0 | 6-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-49 | Et | 0 | 3-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-50 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-51 | Et | 0 | 5-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-52 | Et | 0 | 6-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-53 | Et | 0 | H | 4-tert-Bu | H | CH | CH | 无色油状 | |
1-54 | Et | 0 | H | 4-Ph | H | CH | CH | 棕色固体 | 117-121 |
1-55 | Et | 0 | H | 4-OPh | H | CH | CH | 褐色油状 | |
1-56 | Et | 0 | H | 4-CN | H | CH | CH | 黄色固体 | 72-76 |
1-57 | Et | 0 | H | 2-Cl-4-CF<sub>3</sub> | H | CH | CH | 白色固体 | <60 |
1-58 | Et | 0 | H | 2-Cl-4-CF<sub>3</sub> | Me | CH | CH | ||
1-59 | Et | 0 | H | 2-Cl-4-CF<sub>3</sub> | Cl | CH | CH | ||
1-60 | Et | 0 | H | 2-Cl-4-CF<sub>3</sub> | Br | CH | CH | ||
1-61 | Et | 0 | H | 2-Cl-4-CF<sub>3</sub> | I | CH | CH | ||
1-62 | Et | 0 | H | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-63 | Et | 0 | H | 3-Me-5-CF<sub>3</sub> | Me | CH | CH | ||
1-64 | Et | 0 | H | 3-Me-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-65 | Et | 0 | H | 3-Me-5-CF<sub>3</sub> | Br | CH | CH | ||
1-66 | Et | 0 | H | 3-Me-5-CF<sub>3</sub> | I | CH | CH | ||
1-67 | Et | 0 | 3-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-68 | Et | 0 | 4-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-69 | Et | 0 | 5-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-70 | Et | 0 | 6-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-71 | Et | 0 | 3-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-72 | Et | 0 | 4-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-73 | Et | 0 | 5-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-74 | Et | 0 | 6-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-75 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 67 |
1-76 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-77 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | c-Pr | CH | CH | ||
1-78 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CF3 | CH | CH | ||
1-79 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-80 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-81 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | 白色固体 | 122-125 |
1-82 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | NH<sub>2</sub> | CH | CH | 红褐色油状 | |
1-83 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CO<sub>2</sub>Et | CH | CH | 黄色油状 | |
1-84 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CN | CH | CH | 黄色固体 | 119-121 |
1-85 | Et | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 118-120 |
1-86 | Et | 0 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 115-118 |
1-87 | Et | 0 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 98-100 |
1-88 | Et | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 119-124 |
1-89 | Et | 0 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-90 | Et | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 125-127 |
1-91 | Et | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 无色油状 | 98-100 |
1-92 | Et | 0 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-93 | Et | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-94 | Et | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-95 | Et | 0 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-96 | Et | 0 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-97 | Et | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-98 | Et | 0 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-99 | Et | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-100 | Et | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH |
[表1-3]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-101 | Et | 0 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-102 | Et | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-103 | Et | 0 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-104 | Et | 0 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-105 | Et | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-106 | Et | 0 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-107 | Et | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-108 | Et | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-109 | Et | 0 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-110 | Et | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-111 | Et | 0 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-112 | Et | 0 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-113 | Et | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-114 | Et | 0 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-115 | Et | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-116 | Et | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-117 | Et | 0 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-118 | Et | 0 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-119 | Et | 0 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-120 | Et | 0 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-121 | Et | 0 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-122 | Et | 0 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-123 | Et | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-124 | Et | 0 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-125 | Et | 0 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-126 | Et | 0 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-127 | Et | 0 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-128 | Et | 0 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-129 | Et | 0 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-130 | Et | 0 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-131 | Et | 0 | 3-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-132 | Et | 0 | 4-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-133 | Et | 0 | 5-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-134 | Et | 0 | 6-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-135 | Et | 0 | 3-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-136 | Et | 0 | 4-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-137 | Et | 0 | 5-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-138 | Et | 0 | 6-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-139 | Et | 0 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-140 | Et | 0 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-141 | Et | 0 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-142 | Et | 0 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-143 | Et | 0 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-144 | Et | 0 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-145 | Et | 0 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-146 | Et | 0 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-147 | Et | 0 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-148 | Et | 0 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-149 | Et | 0 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-150 | Et | 0 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-151 | Et | 0 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-152 | Et | 0 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-153 | Et | 0 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-154 | Et | 0 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-155 | Et | 0 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH |
[表1-4]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-156 | Et | 0 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-157 | Et | 0 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-158 | Et | 0 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-159 | Et | 0 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-160 | Et | 0 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-161 | Et | 0 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-162 | Et | 0 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-163 | Et | 0 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-164 | Et | 0 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-165 | Et | 0 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-166 | Et | 0 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-167 | Et | 0 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-168 | Et | 0 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-169 | Et | 0 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-170 | Et | 0 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-171 | Et | 0 | H | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-172 | Et | 0 | H | 3-F-5-CF<sub>3</sub> | Me | CH | CH | ||
1-173 | Et | 0 | H | 3-F-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-174 | Et | 0 | H | 3-F-5-CF<sub>3</sub> | Br | CH | CH | ||
1-175 | Et | 0 | H | 3-F-5-CF<sub>3</sub> | I | CH | CH | ||
1-176 | Et | 0 | 3-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-177 | Et | 0 | 4-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-178 | Et | 0 | 5-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-179 | Et | 0 | 6-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-180 | Et | 0 | 3-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-181 | Et | 0 | 4-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-182 | Et | 0 | 5-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-183 | Et | 0 | 6-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-184 | Et | 0 | H | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-185 | Et | 0 | H | 3-Cl-5-CF<sub>3</sub> | Me | CH | CH | ||
1-186 | Et | 0 | H | 3-Cl-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-187 | Et | 0 | H | 3-Cl-5-CF<sub>3</sub> | Br | CH | CH | ||
1-188 | Et | 0 | H | 3-Cl-5-CF<sub>3</sub> | I | CH | CH | ||
1-189 | Et | 0 | 3-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-190 | Et | 0 | 4-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-191 | Et | 0 | 5-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-192 | Et | 0 | 6-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-193 | Et | 0 | 3-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-194 | Et | 0 | 4-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-195 | Et | 0 | 5-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-196 | Et | 0 | 6-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-197 | Et | 0 | H | 3-Br-5-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
1-198 | Et | 0 | H | 3-Br-5-CF<sub>3</sub> | Me | CH | CH | ||
1-199 | Et | 0 | H | 3-Br-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-200 | Et | 0 | H | 3-Br-5-CF<sub>3</sub> | Br | CH | CH | ||
1-201 | Et | 0 | H | 3-Br-5-CF<sub>3</sub> | I | CH | CH | ||
1-202 | Et | 0 | 3-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-203 | Et | 0 | 4-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-204 | Et | 0 | 5-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-205 | Et | 0 | 6-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-206 | Et | 0 | 3-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-207 | Et | 0 | 4-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-208 | Et | 0 | 5-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-209 | Et | 0 | 6-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-210 | Et | 0 | H | 3-CO<sub>2</sub>Me-5-CF<sub>3</sub> | H | CH | CH | 黄色固体 | 97-100 |
[表1-5]
(续上表)
[表1-6]
(续上表)
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-297 | Et | 1 | H | H | Cl | CH | CH | ||
1-298 | Et | 1 | H | H | Br | CH | CH | ||
1-299 | Et | 1 | H | H | I | CH | CH | ||
1-300 | Et | 1 | H | 3-Cl | H | CH | CH | 白色固体 | 134-136 |
1-301 | Et | 1 | H | 4-Cl | H | CH | CH | 白色固体 | 180-181 |
1-302 | Et | 1 | H | 3-Br | H | CH | CH | 白色固体 | 141-144 |
1-303 | Et | 1 | H | 3-OCF<sub>3</sub> | H | CH | CH | 白色固体 | 109-112 |
1-304 | Et | 1 | H | 2-CF<sub>3</sub> | H | CH | CH | 白色固体 | 131-133 |
1-305 | Et | 1 | H | 3-CF<sub>3</sub> | H | CH | CH | 白色固体 | 144-147 |
1-306 | Et | 1 | H | 3-CF<sub>3</sub> | Me | CH | CH | 红褐色油状 | |
1-307 | Et | 1 | H | 3-CF<sub>3</sub> | Et | CH | CH | ||
1-308 | Et | 1 | H | 3-CF<sub>3</sub> | Cl | CH | CH | 淡黄色油状 | |
1-309 | Et | 1 | H | 3-CF<sub>3</sub> | Br | CH | CH | ||
1-310 | Et | 1 | H | 3-CF<sub>3</sub> | I | CH | CH | 白色固体 | 122-125 |
[表1-7]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-311 | Et | 1 | 3-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-312 | Et | 1 | 4-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-313 | Et | 1 | 5-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-314 | Et | 1 | 6-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-315 | Et | 1 | 3-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-316 | Et | 1 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-317 | Et | 1 | 5-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | 白色固体 | 140-145 |
1-318 | Et | 1 | 6-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-319 | Et | 1 | H | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 149-152 |
1-320 | Et | 1 | H | 4-CF<sub>3</sub> | Me | CH | CH | ||
1-321 | Et | 1 | H | 4-CF<sub>3</sub> | Cl | CH | CH | ||
1-322 | Et | 1 | H | 4-CF<sub>3</sub> | Br | CH | CH | ||
1-323 | Et | 1 | H | 4-CF<sub>3</sub> | I | CH | CH | ||
1-324 | Et | 1 | 3-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-325 | Et | 1 | 4-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-326 | Et | 1 | 5-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-327 | Et | 1 | 6-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-328 | Et | 1 | 3-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-329 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-330 | Et | 1 | 5-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-331 | Et | 1 | 6-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-332 | Et | 1 | H | 4-tert-Bu | H | CH | CH | 白色固体 | 162-167 |
1-333 | Et | 1 | H | 4-Ph | H | CH | CH | 黄色固体 | 157-160 |
1-334 | Et | 1 | H | 4-OPh | H | CH | CH | 褐色油状 | |
1-335 | Et | 1 | H | 4-CN | H | CH | CH | 白色固体 | 158-160 |
1-336 | Et | 1 | H | 2-Cl-4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 103-105 |
1-337 | Et | 1 | H | 2-Cl-4-CF<sub>3</sub> | Me | CH | CH | ||
1-338 | Et | 1 | H | 2-Cl-4-CF<sub>3</sub> | Cl | CH | CH | ||
1-339 | Et | 1 | H | 2-Cl-4-CF<sub>3</sub> | Br | CH | CH | ||
1-340 | Et | 1 | H | 2-Cl-4-CF<sub>3</sub> | I | CH | CH | ||
1-341 | Et | 1 | H | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-342 | Et | 1 | H | 3-Me-5-CF<sub>3</sub> | Me | CH | CH | ||
1-343 | Et | 1 | H | 3-Me-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-344 | Et | 1 | H | 3-Me-5-CF<sub>3</sub> | Br | CH | CH | ||
1-345 | Et | 1 | H | 3-Me-5-CF<sub>3</sub> | I | CH | CH | ||
1-346 | Et | 1 | 3-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-347 | Et | 1 | 4-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-348 | Et | 1 | 5-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-349 | Et | 1 | 6-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-350 | Et | 1 | 3-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-351 | Et | 1 | 4-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-352 | Et | 1 | 5-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-353 | Et | 1 | 6-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-354 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 169-171 |
1-355 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-356 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | c-Pr | CH | CH | ||
1-357 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CF3 | CH | CH | ||
1-358 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-359 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-360 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | 白色固体 | 148-152 |
1-361 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | NH<sub>2</sub> | CH | CH | 白色固体 | 84-89 |
1-362 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CO<sub>2</sub>Et | CH | CH | 淡黄色油状 | |
1-363 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CN | CH | CH | 白色固体 | 134-137 |
1-364 | Et | 1 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 79-82 | |
1-365 | Et | 1 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 186-187 |
[表1-8]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-366 | Et | 1 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 淡黄色固体 | 78-82 |
1-367 | Et | 1 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 64-68 | |
1-368 | Et | 1 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-369 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 136-137 |
1-370 | Et | 1 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 66-81 |
1-371 | Et | 1 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-372 | Et | 1 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-373 | Et | 1 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-374 | Et | 1 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-375 | Et | 1 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-376 | Et | 1 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-377 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-378 | Et | 1 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-379 | Et | 1 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-380 | Et | 1 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-381 | Et | 1 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-382 | Et | 1 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-383 | Et | 1 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-384 | Et | 1 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-385 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-386 | Et | 1 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-387 | Et | 1 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-388 | Et | 1 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-389 | Et | 1 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-390 | Et | 1 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-391 | Et | 1 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-392 | Et | 1 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-393 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-394 | Et | 1 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-395 | Et | 1 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-396 | Et | 1 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-397 | Et | 1 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-398 | Et | 1 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-399 | Et | 1 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-400 | Et | 1 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-401 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-402 | Et | 1 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-403 | Et | 1 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-404 | Et | 1 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-405 | Et | 1 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-406 | Et | 1 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-407 | Et | 1 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-408 | Et | 1 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-409 | Et | 1 | 3-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-410 | Et | 1 | 4-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-411 | Et | 1 | 5-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-412 | Et | 1 | 6-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-413 | Et | 1 | 3-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-414 | Et | 1 | 4-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-415 | Et | 1 | 5-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-416 | Et | 1 | 6-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-417 | Et | 1 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-418 | Et | 1 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-419 | Et | 1 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-420 | Et | 1 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH |
[表1-9]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-421 | Et | 1 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-422 | Et | 1 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-423 | Et | 1 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-424 | Et | 1 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-425 | Et | 1 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-426 | Et | 1 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-427 | Et | 1 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-428 | Et | 1 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-429 | Et | 1 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-430 | Et | 1 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-431 | Et | 1 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-432 | Et | 1 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-433 | Et | 1 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-434 | Et | 1 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-435 | Et | 1 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-436 | Et | 1 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-437 | Et | 1 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-438 | Et | 1 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-439 | Et | 1 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-440 | Et | 1 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-441 | Et | 1 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-442 | Et | 1 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-443 | Et | 1 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-444 | Et | 1 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-445 | Et | 1 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-446 | Et | 1 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-447 | Et | 1 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-448 | Et | 1 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-449 | Et | 1 | H | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-450 | Et | 1 | H | 3-F-5-CF<sub>3</sub> | Me | CH | CH | ||
1-451 | Et | 1 | H | 3-F-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-452 | Et | 1 | H | 3-F-5-CF<sub>3</sub> | Br | CH | CH | ||
1-453 | Et | 1 | H | 3-F-5-CF<sub>3</sub> | I | CH | CH | ||
1-454 | Et | 1 | 3-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-455 | Et | 1 | 4-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-456 | Et | 1 | 5-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-457 | Et | 1 | 6-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-458 | Et | 1 | 3-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-459 | Et | 1 | 4-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-460 | Et | 1 | 5-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-461 | Et | 1 | 6-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-462 | Et | 1 | H | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-463 | Et | 1 | H | 3-Cl-5-CF<sub>3</sub> | Me | CH | CH | ||
1-464 | Et | 1 | H | 3-Cl-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-465 | Et | 1 | H | 3-Cl-5-CF<sub>3</sub> | Br | CH | CH | ||
1-466 | Et | 1 | H | 3-Cl-5-CF<sub>3</sub> | I | CH | CH | ||
1-467 | Et | 1 | 3-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-468 | Et | 1 | 4-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-469 | Et | 1 | 5-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-470 | Et | 1 | 6-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-471 | Et | 1 | 3-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-472 | Et | 1 | 4-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-473 | Et | 1 | 5-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-474 | Et | 1 | 6-CF<sub>3</sub> | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-475 | Et | 1 | H | 3-Br-5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 172-173 |
[表1-10]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-476 | Et | 1 | H | 3-Br-5-CF<sub>3</sub> | Me | CH | CH | ||
1-477 | Et | 1 | H | 3-Br-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-478 | Et | 1 | H | 3-Br-5-CF<sub>3</sub> | Br | CH | CH | ||
1-479 | Et | 1 | H | 3-Br-5-CF<sub>3</sub> | I | CH | CH | ||
1-480 | Et | 1 | 3-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-481 | Et | 1 | 4-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-482 | Et | 1 | 5-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-483 | Et | 1 | 6-Cl | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-484 | Et | 1 | 3-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-485 | Et | 1 | 4-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-486 | Et | 1 | 5-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-487 | Et | 1 | 6-CF<sub>3</sub> | 3-Br-5-CF<sub>3</sub> | H | CH | CH | ||
1-488 | Et | 1 | H | 3-CO<sub>2</sub>Me-5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 71-82 |
1-489 | Et | 1 | H | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-490 | Et | 1 | 4-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-491 | Et | 1 | 5-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-492 | Et | 1 | 6-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-493 | Et | 1 | 3-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-494 | Et | 1 | 4-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-495 | Et | 1 | 5-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-496 | Et | 1 | 6-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-497 | Et | 1 | H | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-498 | Et | 1 | 4-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-499 | Et | 1 | 5-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-500 | Et | 1 | 6-Cl | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-501 | Et | 1 | 3-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-502 | Et | 1 | 4-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-503 | Et | 1 | 5-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-504 | Et | 1 | 6-CF<sub>3</sub> | 3,4-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-505 | Et | 1 | H | 3-CONHPh-5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 227-230 |
1-506 | Et | 1 | H | 3-CONH(4-ClC<sub>6</sub>H<sub>4</sub>)-5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 206-211 |
1-507 | Et | 1 | 5-F | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 187-188 |
1-508 | Et | 1 | 5-Me | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 166-167 |
1-509 | Et | 1 | 5-OMe | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 65-70 |
1-510 | Et | 1 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | N | CH | 白色固体 | 250≤ |
1-511 | Et | 1 | H | 4-CF(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 174-179 |
1-512 | Et | 1 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | F | CH | CH | 白色固体 | 120-122 |
1-513 | Et | 1 | H | 3-SF<sub>5</sub> | H | CH | CH | 白色固体 | 153-154 |
1-514 | Et | 1 | H | 3-Ac-5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 154-156 |
(续上表)
[表1-11]
(续上表)
[表1-12]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-581 | Et | 2 | H | 2-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
1-582 | Et | 2 | H | 3-CF<sub>3</sub> | H | CH | CH | 黄色固体 | 105-114 |
1-583 | Et | 2 | H | 3-CF<sub>3</sub> | Me | CH | CH | 红褐色油状 | |
1-584 | Et | 2 | H | 3-CF<sub>3</sub> | Et | CH | CH | 淡黄色油状 | |
1-585 | Et | 2 | H | 3-CF<sub>3</sub> | Cl | CH | CH | 淡黄色油状 | |
1-586 | Et | 2 | H | 3-CF<sub>3</sub> | Br | CH | CH | ||
1-587 | Et | 2 | H | 3-CF<sub>3</sub> | I | CH | CH | 白色固体 | 163-165 |
1-588 | Et | 2 | 3-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-589 | Et | 2 | 4-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-590 | Et | 2 | 5-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-591 | Et | 2 | 6-Cl | 3-CF<sub>3</sub> | H | CH | CH | ||
1-592 | Et | 2 | 3-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-593 | Et | 2 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-594 | Et | 2 | 5-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
1-595 | Et | 2 | 6-CF<sub>3</sub> | 3-CF<sub>3</sub> | H | CH | CH | ||
1-596 | Et | 2 | H | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 168-171 |
1-597 | Et | 2 | H | 4-CF<sub>3</sub> | Me | CH | CH | ||
1-598 | Et | 2 | H | 4-CF<sub>3</sub> | Cl | CH | CH | ||
1-599 | Et | 2 | H | 4-CF<sub>3</sub> | Br | CH | CH | ||
1-600 | Et | 2 | H | 4-CF<sub>3</sub> | I | CH | CH | ||
1-601 | Et | 2 | 3-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-602 | Et | 2 | 4-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-603 | Et | 2 | 5-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-604 | Et | 2 | 6-Cl | 4-CF<sub>3</sub> | H | CH | CH | ||
1-605 | Et | 2 | 3-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-606 | Et | 2 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-607 | Et | 2 | 5-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-608 | Et | 2 | 6-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | ||
1-609 | Et | 2 | H | 4-tert-Bu | H | CH | CH | 白色固体 | 127-131 |
1-610 | Et | 2 | H | 4-Ph | H | CH | CH | 黄色固体 | 178-181 |
1-611 | Et | 2 | H | 4-OPh | H | CH | CH | 褐色固体 | 155-159 |
1-612 | Et | 2 | H | 4-CN | H | CH | CH | 白色固体 | 165-167 |
1-613 | Et | 2 | H | 2-Cl-4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 137-139 |
1-614 | Et | 2 | H | 2-Cl-4-CF<sub>3</sub> | Me | CH | CH | ||
1-615 | Et | 2 | H | 2-Cl-4-CF<sub>3</sub> | Cl | CH | CH | ||
1-616 | Et | 2 | H | 2-Cl-4-CF<sub>3</sub> | Br | CH | CH | ||
1-617 | Et | 2 | H | 2-Cl-4-CF<sub>3</sub> | I | CH | CH | ||
1-618 | Et | 2 | H | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-619 | Et | 2 | H | 3-Me-5-CF<sub>3</sub> | Me | CH | CH | ||
1-620 | Et | 2 | H | 3-Me-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-621 | Et | 2 | H | 3-Me-5-CF<sub>3</sub> | Br | CH | CH | ||
1-622 | Et | 2 | H | 3-Me-5-CF<sub>3</sub> | I | CH | CH | ||
1-623 | Et | 2 | 3-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-624 | Et | 2 | 4-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-625 | Et | 2 | 5-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-626 | Et | 2 | 6-Cl | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-627 | Et | 2 | 3-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-628 | Et | 2 | 4-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-629 | Et | 2 | 5-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-630 | Et | 2 | 6-CF<sub>3</sub> | 3-Me-5-CF<sub>3</sub> | H | CH | CH | ||
1-631 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 135-139 |
1-632 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-633 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | c-Pr | CH | CH | ||
1-634 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH | CH | ||
1-635 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH |
[表1-13]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-636 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-637 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | 白色固体 | 182-185 |
1-638 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | NH<sub>2</sub> | CH | CH | 白色固体 | 83-90 |
1-639 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CO<sub>2</sub>Et | CH | CH | 淡黄色油状 | |
1-640 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | CN | CH | CH | 白色固体 | 135-138 |
1-641 | Et | 2 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 170-172 |
1-642 | Et | 2 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 180-182 |
1-643 | Et | 2 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 72-75 |
1-644 | Et | 2 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 156-158 |
1-645 | Et | 2 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-646 | Et | 2 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 156-158 |
1-647 | Et | 2 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 171-173 |
1-648 | Et | 2 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-649 | Et | 2 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-650 | Et | 2 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-651 | Et | 2 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-652 | Et | 2 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-653 | Et | 2 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-654 | Et | 2 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-655 | Et | 2 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-656 | Et | 2 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-657 | Et | 2 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-658 | Et | 2 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-659 | Et | 2 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-660 | Et | 2 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-661 | Et | 2 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-662 | Et | 2 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-663 | Et | 2 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-664 | Et | 2 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-665 | Et | 2 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-666 | Et | 2 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-667 | Et | 2 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-668 | Et | 2 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-669 | Et | 2 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-670 | Et | 2 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-671 | Et | 2 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-672 | Et | 2 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-673 | Et | 2 | 3-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-674 | Et | 2 | 4-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-675 | Et | 2 | 5-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-676 | Et | 2 | 6-Cl | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-677 | Et | 2 | 3-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-678 | Et | 2 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-679 | Et | 2 | 5-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-680 | Et | 2 | 6-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-681 | Et | 2 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-682 | Et | 2 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-683 | Et | 2 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-684 | Et | 2 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-685 | Et | 2 | H | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-686 | Et | 2 | 3-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-687 | Et | 2 | 4-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-688 | Et | 2 | 5-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-689 | Et | 2 | 6-Cl | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-690 | Et | 2 | 3-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH |
[表1-14]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-691 | Et | 2 | 4-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-692 | Et | 2 | 5-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-693 | Et | 2 | 6-CF<sub>3</sub> | 4-Cl-3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-694 | Et | 2 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-695 | Et | 2 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-696 | Et | 2 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-697 | Et | 2 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-698 | Et | 2 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-699 | Et | 2 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-700 | Et | 2 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-701 | Et | 2 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-702 | Et | 2 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-703 | Et | 2 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-704 | Et | 2 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-705 | Et | 2 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-706 | Et | 2 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-707 | Et | 2 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-708 | Et | 2 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-709 | Et | 2 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-710 | Et | 2 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-711 | Et | 2 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-712 | Et | 2 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-713 | Et | 2 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-714 | Et | 2 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-715 | Et | 2 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-716 | Et | 2 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-717 | Et | 2 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-718 | Et | 2 | 3-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-719 | Et | 2 | 4-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-720 | Et | 2 | 5-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-721 | Et | 2 | 6-Cl | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-722 | Et | 2 | 3-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-723 | Et | 2 | 4-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-724 | Et | 2 | 5-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-725 | Et | 2 | 6-CF<sub>3</sub> | 4-Me-3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-726 | Et | 2 | H | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-727 | Et | 2 | H | 3-F-5-CF<sub>3</sub> | Me | CH | CH | ||
1-728 | Et | 2 | H | 3-F-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-729 | Et | 2 | H | 3-F-5-CF<sub>3</sub> | Br | CH | CH | ||
1-730 | Et | 2 | H | 3-F-5-CF<sub>3</sub> | I | CH | CH | ||
1-731 | Et | 2 | 3-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-732 | Et | 2 | 4-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-733 | Et | 2 | 5-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-734 | Et | 2 | 6-Cl | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-735 | Et | 2 | 3-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-736 | Et | 2 | 4-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-737 | Et | 2 | 5-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-738 | Et | 2 | 6-CF<sub>3</sub> | 3-F-5-CF<sub>3</sub> | H | CH | CH | ||
1-739 | Et | 2 | H | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-740 | Et | 2 | H | 3-Cl-5-CF<sub>3</sub> | Me | CH | CH | ||
1-741 | Et | 2 | H | 3-Cl-5-CF<sub>3</sub> | Cl | CH | CH | ||
1-742 | Et | 2 | H | 3-Cl-5-CF<sub>3</sub> | Br | CH | CH | ||
1-743 | Et | 2 | H | 3-Cl-5-CF<sub>3</sub> | I | CH | CH | ||
1-744 | Et | 2 | 3-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH | ||
1-745 | Et | 2 | 4-Cl | 3-Cl-5-CF<sub>3</sub> | H | CH | CH |
[表1-15]
[表1-16]
(续上表)
[表1-17]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-846 | Et | 2 | H | 3-COOH-5-CF<sub>3</sub> | H | CH | CH | ||
1-847 | Et | 2 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | NHCO(2-ClC<sub>6</sub>H<sub>4</sub>) | CH | CH | 白色固体 | 88-95 |
1-848 | Et | 2 | 4-CF(CF<sub>3</sub>)<sub>2</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-849 | Et | 2 | 4-SF<sub>5</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-850 | Et | 0 | H | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-851 | Et | 0 | 4-Cl | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-852 | Et | 0 | 4-Br | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-853 | Et | 0 | 4-I | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 黄色油状物 | |
1-854 | Et | 0 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-855 | Et | 0 | 4-OCF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 黄色油状物 | |
1-856 | Et | 0 | 4-SF<sub>5</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-857 | Et | 1 | H | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-858 | Et | 1 | 4-Cl | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-859 | Et | 1 | 4-Br | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-860 | Et | 1 | 4-I | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 白色固体 | 135-140 |
1-861 | Et | 1 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-862 | Et | 1 | 4-OCF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 白色固体 | 135-140 |
1-863 | Et | 1 | 4-SF<sub>5</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-864 | Et | 2 | H | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-865 | Et | 2 | 4-Cl | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-866 | Et | 2 | 4-Br | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-867 | Et | 2 | 4-I | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 白色固体 | 183-187 |
1-868 | Et | 2 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-869 | Et | 2 | 4-OCF<sub>3</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | 白色固体 | 114-117 |
1-870 | Et | 2 | 4-SF<sub>5</sub> | 3-CF<sub>3</sub>-4-Cl | H | CH | CH | ||
1-871 | n-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-872 | n-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-873 | n-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-874 | n-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-875 | n-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-876 | n-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-877 | n-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-878 | n-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-879 | n-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-880 | n-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-881 | i-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-882 | i-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-883 | i-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-884 | i-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-885 | i-Pr | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-886 | i-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-887 | i-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-888 | i-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-889 | i-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-890 | i-Pr | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-891 | n-Bu | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-892 | n-Bu | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-893 | n-Bu | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-894 | n-Bu | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-895 | n-Bu | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-896 | n-Bu | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-897 | n-Bu | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-898 | n-Bu | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-899 | n-Bu | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-900 | n-Bu | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH |
[表1-18]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
1-901 | n-Pen | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-902 | n-Pen | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-903 | n-Pen | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-904 | n-Pen | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-905 | n-Pen | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-906 | n-Pen | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-907 | n-Pen | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-908 | n-Pen | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-909 | n-Pen | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-910 | n-Pen | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-911 | n-Hex | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-912 | n-Hex | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-913 | n-Hex | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-914 | n-Hex | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-915 | n-Hex | 0 | H | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
1-916 | n-Hex | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
1-917 | n-Hex | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
1-918 | n-Hex | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
1-919 | n-Hex | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
1-920 | n-Hex | 0 | 4-CF<sub>3</sub> | 3,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH |
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
2-1 | Me | 0 | H | H | H | CH | CH | ||
2-2 | Me | 0 | H | 4-CF<sub>3</sub> | H | CH | CH | ||
2-3 | Me | 0 | H | 5-CF<sub>3</sub> | H | CH | CH | ||
2-4 | Me | 0 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
2-5 | Me | 0 | H | 4-CF<sub>3</sub> | Br | CH | CH | ||
2-6 | Me | 0 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
2-7 | Me | 0 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
2-8 | Me | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | Br | CH | CH | ||
2-9 | Me | 0 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | Br | CH | CH | ||
2-10 | Me | 0 | 4-CF<sub>3</sub> | 6-CF<sub>3</sub> | Br | CH | CH | ||
2-11 | Me | 0 | H | 4-CF<sub>3</sub> | I | CH | CH | ||
2-12 | Me | 0 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
2-13 | Me | 0 | H | 6-CF<sub>3</sub> | I | CH | CH | ||
2-14 | Et | 0 | H | H | H | CH | CH | 黄色油状 | |
2-15 | Et | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 红褐色油状 | |
2-16 | Et | 0 | 4-Cl | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-17 | Et | 0 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-18 | Et | 0 | 4-I | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-19 | Et | 0 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-20 | Et | 0 | 4-OCF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 82-84 |
2-21 | Et | 0 | 4-SF<sub>5</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-22 | Et | 0 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-23 | Et | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-24 | Et | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-25 | Et | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-26 | Et | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-27 | Et | 0 | H | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-28 | Et | 0 | 4-Cl | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-29 | Et | 0 | 4-Br | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-30 | Et | 0 | 4-I | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 103-105 |
2-31 | Et | 0 | 4-CF<sub>3</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-32 | Et | 0 | 4-OCF<sub>3</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 86-87 |
2-33 | Et | 0 | 4-SF<sub>5</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 黄色固体 | 84-87 |
2-34 | Et | 0 | H | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-35 | Et | 0 | 4-Cl | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-36 | Et | 0 | 4-Br | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-37 | Et | 0 | 4-I | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-38 | Et | 0 | 4-CF<sub>3</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-39 | Et | 0 | 4-OCF<sub>3</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-40 | Et | 0 | 4-SF<sub>5</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-41 | Et | 0 | H | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-42 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-43 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-44 | Et | 0 | 4-I | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-45 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH |
[表2-2]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
2-46 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-47 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-48 | Et | 0 | H | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-49 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-50 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-51 | Et | 0 | 4-I | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-52 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-53 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-54 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-55 | Et | 0 | H | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-56 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-57 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-58 | Et | 0 | 4-I | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-59 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-60 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-61 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-62 | Et | 0 | H | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-63 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-64 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-65 | Et | 0 | 4-I | 4-CF<sub>3</sub>-5-Br | H | CH | CH | 白色固体 | 188-197 |
2-66 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-67 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-68 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-69 | Et | 0 | H | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-70 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-71 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-72 | Et | 0 | 4-I | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-73 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-74 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-75 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-76 | Et | 0 | H | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-77 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-78 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-79 | Et | 0 | 4-I | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-80 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-81 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-82 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-83 | Et | 0 | H | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-84 | Et | 0 | 4-Cl | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-85 | Et | 0 | 4-Br | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-86 | Et | 0 | 4-I | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-87 | Et | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-88 | Et | 0 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | 白色固体 | 163 |
2-89 | Et | 0 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-90 | Et | 0 | H | 3-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
2-91 | Et | 0 | H | 4-CF<sub>3</sub> | H | CH | CH | 褐色油状 | |
2-92 | Et | 0 | H | 4-CF<sub>3</sub> | H | N | CH | ||
2-93 | Et | 0 | H | 4-CF<sub>3</sub> | H | CH | N | ||
2-94 | Et | 0 | H | 4-CF<sub>3</sub> | H | N | N | ||
2-95 | Et | 0 | 3-Cl | 4-CF<sub>3</sub> | H | CH | CH | 褐色油状 | |
2-96 | Et | 0 | 4-Cl | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 114-116 |
2-97 | Et | 0 | 5-Cl | 4-CF<sub>3</sub> | H | CH | CH | 褐色固体 | 122-123 |
2-98 | Et | 0 | 6-Cl | 4-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
2-99 | Et | 0 | 4-F | 4-CF<sub>3</sub> | H | CH | CH | 棕色固体 | 102 |
2-100 | Et | 0 | 4-Br | 4-CF<sub>3</sub> | H | CH | CH | 褐色固体 | 97-98 |
[表2-3]
(续上表)
[表2-4]
[表2-5]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
2-201 | Et | 1 | H | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-202 | Et | 1 | 4-Cl | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-203 | Et | 1 | 4-Br | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-204 | Et | 1 | 4-I | 4-CF<sub>3</sub>-5-Br | H | CH | CH | 白色固体 | 188-197 |
2-205 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-206 | Et | 1 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-207 | Et | 1 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-208 | Et | 1 | H | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-209 | Et | 1 | 4-Cl | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-210 | Et | 1 | 4-Br | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-211 | Et | 1 | 4-I | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-212 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-213 | Et | 1 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-214 | Et | 1 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-215 | Et | 1 | H | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-216 | Et | 1 | 4-Cl | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-217 | Et | 1 | 4-Br | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-218 | Et | 1 | 4-I | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-219 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-220 | Et | 1 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-221 | Et | 1 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-OMe | H | CH | CH | ||
2-222 | Et | 1 | H | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-223 | Et | 1 | 4-Cl | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-224 | Et | 1 | 4-Br | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-225 | Et | 1 | 4-I | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-226 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-227 | Et | 1 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | 白色固体 | 163 |
2-228 | Et | 1 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-CN | H | CH | CH | ||
2-229 | Et | 1 | H | 3-CF<sub>3</sub> | H | CH | CH | 白色固体 | 175-177 |
2-230 | Et | 1 | H | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 165-166 |
2-231 | Et | 1 | H | 4-CF<sub>3</sub> | H | N | CH | ||
2-232 | Et | 1 | H | 4-CF<sub>3</sub> | H | CH | N | ||
2-233 | Et | 1 | H | 4-CF<sub>3</sub> | H | N | N | ||
2-234 | Et | 1 | 3-Cl | 4-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
2-235 | Et | 1 | 4-Cl | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 175-177 |
2-236 | Et | 1 | 5-Cl | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 158-162 |
2-237 | Et | 1 | 6-Cl | 4-CF<sub>3</sub> | H | CH | CH | 无色油状 | |
2-238 | Et | 1 | 4-F | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 183-185 |
2-239 | Et | 1 | 4-Br | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 186-193 |
2-240 | Et | 1 | 4-Br | 4-CF<sub>3</sub> | H | N | CH | ||
2-241 | Et | 1 | 4-I | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 182-186 |
2-242 | Et | 1 | 4-Me | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 153-156 |
2-243 | Et | 1 | 4-CN | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 213-215 |
2-244 | Et | 1 | 4-OH | 4-CF<sub>3</sub> | H | CH | CH | ||
2-245 | Et | 1 | 4-COOEt | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 162-165 |
2-246 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 186-187 |
2-247 | Et | 1 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | H | N | CH | ||
2-248 | Et | 1 | 4-CF(CF<sub>3</sub>)<sub>2</sub> | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 190-192 |
2-249 | Et | 1 | 4-CH(CF<sub>3</sub>)<sub>2</sub> | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 154-156 |
2-250 | Et | 1 | 4-C(CF<sub>3</sub>)<sub>2</sub>OMe | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 167-169 |
2-251 | Et | 1 | 4-OMe | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 134-144 |
2-252 | Et | 1 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 161-165 |
2-253 | Et | 1 | 4-SCF<sub>3</sub> | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 166-168 |
2-254 | Et | 1 | 4-SMe | 4-CF<sub>3</sub> | H | CH | CH | ||
2-255 | Et | 1 | 4-SOMe | 4-CF<sub>3</sub> | H | CH | CH |
[表2-6]
[表2-7]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
2-296 | Et | 2 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-297 | Et | 2 | 4-I | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 154-155 |
2-298 | Et | 2 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-299 | Et | 2 | 4-OCF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 179-180 |
2-300 | Et | 2 | 4-SF<sub>5</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-301 | Et | 2 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-302 | Et | 2 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-303 | Et | 2 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-304 | Et | 2 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-305 | Et | 2 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-306 | Et | 2 | H | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-307 | Et | 2 | 4-Cl | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-308 | Et | 2 | 4-Br | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-309 | Et | 2 | 4-I | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 186-188 |
2-310 | Et | 2 | 4-CF<sub>3</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-311 | Et | 2 | 4-OCF<sub>3</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 163-164 |
2-312 | Et | 2 | 4-SF<sub>5</sub> | 3-CN-4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | 白色固体 | 208-209 |
2-313 | Et | 2 | H | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-314 | Et | 2 | 4-Cl | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-315 | Et | 2 | 4-Br | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-316 | Et | 2 | 4-I | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-317 | Et | 2 | 4-CF<sub>3</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-318 | Et | 2 | 4-OCF<sub>3</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-319 | Et | 2 | 4-SF<sub>5</sub> | 3-Cl-4-CF<sub>3</sub> | H | CH | CH | ||
2-320 | Et | 2 | H | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-321 | Et | 2 | 4-Cl | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-322 | Et | 2 | 4-Br | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | 白色固体 | 195-198 |
2-323 | Et | 2 | 4-I | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | 白色固体 | 190-194 |
2-324 | Et | 2 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-325 | Et | 2 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | 白色固体 | 149-151 |
2-326 | Et | 2 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-5-Cl | H | CH | CH | ||
2-327 | Et | 2 | H | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-328 | Et | 2 | 4-Cl | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-329 | Et | 2 | 4-Br | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | 白色固体 | 179-180 |
2-330 | Et | 2 | 4-I | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | 白色固体 | 187-188 |
2-331 | Et | 2 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-332 | Et | 2 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | 白色固体 | 179-180 |
2-333 | Et | 2 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-6-Cl | H | CH | CH | ||
2-334 | Et | 2 | H | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-335 | Et | 2 | 4-Cl | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-336 | Et | 2 | 4-Br | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-337 | Et | 2 | 4-I | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-338 | Et | 2 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-339 | Et | 2 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-340 | Et | 2 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-3-Br | H | CH | CH | ||
2-341 | Et | 2 | H | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-342 | Et | 2 | 4-Cl | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-343 | Et | 2 | 4-Br | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-344 | Et | 2 | 4-I | 4-CF<sub>3</sub>-5-Br | H | CH | CH | 白色固体 | 188-197 |
2-345 | Et | 2 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-346 | Et | 2 | 4-OCF<sub>3</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-347 | Et | 2 | 4-SF<sub>5</sub> | 4-CF<sub>3</sub>-5-Br | H | CH | CH | ||
2-348 | Et | 2 | H | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-349 | Et | 2 | 4-Cl | 4-CF<sub>3</sub>-6-Br | H | CH | CH | ||
2-350 | Et | 2 | 4-Br | 4-CF<sub>3</sub>-6-Br | H | CH | CH |
[表2-8]
[表2-9]
[表2-10]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
2-446 | n-Pr | 2 | H | 4-CF<sub>3</sub> | H | CH | CH | 白色固体 | 120-123 |
2-447 | n-Pr | 2 | H | 5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 109-111 |
2-448 | i-Pr | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-449 | i-Pr | 0 | 4-Cl | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-450 | i-Pr | 0 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-451 | i-Pr | 0 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-452 | i-Pr | 0 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-453 | i-Pr | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-454 | i-Pr | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-455 | i-Pr | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-456 | i-Pr | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-457 | n-Bu | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-458 | n-Bu | 0 | 4-Cl | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-459 | n-Bu | 0 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-460 | n-Bu | 0 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-461 | n-Bu | 0 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-462 | n-Bu | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-463 | n-Bu | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-464 | n-Bu | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-465 | n-Bu | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-466 | n-Pen | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-467 | n-Pen | 0 | 4-Cl | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-468 | n-Pen | 0 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-469 | n-Pen | 0 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-470 | n-Pen | 0 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-471 | n-Pen | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-472 | n-Pen | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-473 | n-Pen | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-474 | n-Pen | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-475 | n-Hex | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-476 | n-Hex | 0 | 4-Cl | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-477 | n-Hex | 0 | 4-Br | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-478 | n-Hex | 0 | 4-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-479 | n-Hex | 0 | 5-CF<sub>3</sub> | 4,6-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
2-480 | n-Hex | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
2-481 | n-Hex | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
2-482 | n-Hex | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
2-483 | n-Hex | 0 | H | 4,6-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
2-484 | CF<sub>3</sub>CH<sub>2</sub> | 0 | H | 5-CF<sub>3</sub> | H | CH | CH | 黄色油状 | |
2-485 | CF<sub>3</sub>CH<sub>2</sub> | 1 | H | 5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 198-199 |
2-486 | CF<sub>3</sub>CH<sub>2</sub> | 2 | H | 5-CF<sub>3</sub> | H | CH | CH |
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
3-1 | Me | 0 | H | H | H | CH | CH | ||
3-2 | Me | 0 | H | 4-CF<sub>3</sub> | H | CH | CH | ||
3-3 | Me | 0 | H | 5-CF<sub>3</sub> | H | CH | CH | ||
3-4 | Me | 0 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
3-5 | Me | 0 | H | 4-CF<sub>3</sub> | Br | CH | CH | ||
3-6 | Me | 0 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-7 | Me | 0 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-8 | Me | 0 | 4-CF<sub>3</sub> | 4-CF<sub>3</sub> | Br | CH | CH | ||
3-9 | Me | 0 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-10 | Me | 0 | 4-CF<sub>3</sub> | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-11 | Me | 0 | H | 4-CF<sub>3</sub> | I | CH | CH | ||
3-12 | Me | 0 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
3-13 | Me | 0 | H | 6-CF<sub>3</sub> | I | CH | CH | ||
3-14 | Et | 0 | H | H | H | CH | CH | 白色固体 | 83-84 |
3-15 | Et | 0 | H | 5-CF<sub>3</sub> | H | CH | CH | 淡黄色固体 | 79-81 |
3-16 | Et | 0 | 4-Cl | 5-CF<sub>3</sub> | H | CH | CH | ||
3-17 | Et | 0 | 4-Br | 5-CF<sub>3</sub> | H | CH | CH | ||
3-18 | Et | 0 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-19 | Et | 0 | 5-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-20 | Et | 0 | H | 5-CF<sub>3</sub> | Me | CH | CH | ||
3-21 | Et | 0 | H | 5-CF<sub>3</sub> | Cl | CH | CH | ||
3-22 | Et | 0 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-23 | Et | 0 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
3-24 | Et | 0 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
3-25 | Et | 0 | H | 6-CF<sub>3</sub> | Me | CH | CH | ||
3-26 | Et | 0 | H | 6-CF<sub>3</sub> | Cl | CH | CH | ||
3-27 | Et | 0 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-28 | Et | 0 | H | 6-CF<sub>3</sub> | I | CH | CH | ||
3-29 | Et | 1 | H | H | H | CH | CH | 白色固体 | 132-133 |
3-30 | Et | 1 | H | 5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 186-187 |
3-31 | Et | 1 | 4-Cl | 5-CF<sub>3</sub> | H | CH | CH | ||
3-32 | Et | 1 | 4-Br | 5-CF<sub>3</sub> | H | CH | CH | ||
3-33 | Et | 1 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-34 | Et | 1 | 5-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-35 | Et | 1 | H | 5-CF<sub>3</sub> | Me | CH | CH | ||
3-36 | Et | 1 | H | 5-CF<sub>3</sub> | Cl | CH | CH | ||
3-37 | Et | 1 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-38 | Et | 1 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
3-39 | Et | 1 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
3-40 | Et | 1 | H | 6-CF<sub>3</sub> | Me | CH | CH | ||
3-41 | Et | 1 | H | 6-CF<sub>3</sub> | Cl | CH | CH | ||
3-42 | Et | 1 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-43 | Et | 1 | H | 6-CF<sub>3</sub> | I | CH | CH | ||
3-44 | Et | 2 | H | H | H | CH | CH | ||
3-45 | Et | 2 | H | 5-CF<sub>3</sub> | H | CH | CH | 白色固体 | 124-126 |
[表3-2]
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
3-46 | Et | 2 | 4-Cl | 5-CF<sub>3</sub> | H | CH | CH | ||
3-47 | Et | 2 | 4-Br | 5-CF<sub>3</sub> | H | CH | CH | ||
3-48 | Et | 2 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-49 | Et | 2 | 5-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-50 | Et | 2 | H | 5-CF<sub>3</sub> | Me | CH | CH | ||
3-51 | Et | 2 | H | 5-CF<sub>3</sub> | Cl | CH | CH | ||
3-52 | Et | 2 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-53 | Et | 2 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
3-54 | Et | 2 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
3-55 | Et | 2 | H | 6-CF<sub>3</sub> | Me | CH | CH | ||
3-56 | Et | 2 | H | 6-CF<sub>3</sub> | Cl | CH | CH | ||
3-57 | Et | 2 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-58 | Et | 2 | H | 6-CF<sub>3</sub> | I | CH | CH | ||
3-59 | n-Hex | 0 | H | H | H | CH | CH | ||
3-60 | n-Hex | 0 | H | 5-CF<sub>3</sub> | H | CH | CH | ||
3-61 | n-Hex | 0 | 4-Cl | 5-CF<sub>3</sub> | H | CH | CH | ||
3-62 | n-Hex | 0 | 4-Br | 5-CF<sub>3</sub> | H | CH | CH | ||
3-63 | n-Hex | 0 | 4-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-64 | n-Hex | 0 | 5-CF<sub>3</sub> | 5-CF<sub>3</sub> | H | CH | CH | ||
3-65 | n-Hex | 0 | H | 5-CF<sub>3</sub> | Me | CH | CH | ||
3-66 | n-Hex | 0 | H | 5-CF<sub>3</sub> | Cl | CH | CH | ||
3-67 | n-Hex | 0 | H | 5-CF<sub>3</sub> | Br | CH | CH | ||
3-68 | n-Hex | 0 | H | 5-CF<sub>3</sub> | I | CH | CH | ||
3-69 | n-Hex | 0 | H | 6-CF<sub>3</sub> | H | CH | CH | ||
3-70 | n-Hex | 0 | H | 6-CF<sub>3</sub> | Me | CH | CH | ||
3-71 | n-Hex | 0 | H | 6-CF<sub>3</sub> | Cl | CH | CH | ||
3-72 | n-Hex | 0 | H | 6-CF<sub>3</sub> | Br | CH | CH | ||
3-73 | n-Hex | 0 | H | 6-CF<sub>3</sub> | I | CH | CH |
化合物编号 | R | n | Xm | Yp | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
4-1 | Me | 0 | H | H | H | CH | CH | ||
4-2 | Me | 0 | H | 2-CF<sub>3</sub> | H | CH | CH | ||
4-3 | Me | 0 | H | 3-CF<sub>3</sub> | H | CH | CH | ||
4-4 | Me | 0 | H | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-5 | Me | 0 | H | 3-CF<sub>3</sub> | Br | CH | CH | ||
4-6 | Me | 0 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-7 | Me | 0 | 4-CF<sub>3</sub> | 3-CF<sub>3</sub> | Br | CH | CH | ||
4-8 | Me | 0 | H | 2-CF<sub>3</sub> | I | CH | CH | ||
4-9 | Me | 0 | H | 3-CF<sub>3</sub> | I | CH | CH | ||
4-10 | Et | 0 | H | H | H | CH | CH | 淡棕色固体 | 103-105 |
4-11 | Et | 0 | H | 2-CF<sub>3</sub> | H | CH | CH | ||
4-12 | Et | 0 | 4-Cl | 2-CF<sub>3</sub> | H | CH | CH | ||
4-13 | Et | 0 | 4-Br | 2-CF<sub>3</sub> | H | CH | CH | ||
4-14 | Et | 0 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-15 | Et | 0 | 5-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-16 | Et | 0 | H | 2-CF<sub>3</sub> | Me | CH | CH | ||
4-17 | Et | 0 | H | 2-CF<sub>3</sub> | Cl | CH | CH | ||
4-18 | Et | 0 | H | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-19 | Et | 0 | H | 2-CF<sub>3</sub> | I | CH | CH | ||
4-20 | Et | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
4-21 | Et | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
4-22 | Et | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
4-23 | Et | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
4-24 | Et | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
4-25 | Et | 1 | H | H | H | CH | CH | 白色固体 | 160-164 |
4-26 | Et | 1 | H | 2-CF<sub>3</sub> | H | CH | CH | ||
4-27 | Et | 1 | 4-Cl | 2-CF<sub>3</sub> | H | CH | CH | ||
4-28 | Et | 1 | 4-Br | 2-CF<sub>3</sub> | H | CH | CH | ||
4-29 | Et | 1 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-30 | Et | 1 | 5-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-31 | Et | 1 | H | 2-CF<sub>3</sub> | Me | CH | CH | ||
4-32 | Et | 1 | H | 2-CF<sub>3</sub> | Cl | CH | CH | ||
4-33 | Et | 1 | H | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-34 | Et | 1 | H | 2-CF<sub>3</sub> | I | CH | CH | ||
4-35 | Et | 1 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
4-36 | Et | 1 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
4-37 | Et | 1 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
4-38 | Et | 1 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
4-39 | Et | 1 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
4-40 | Et | 2 | H | H | H | CH | CH | ||
4-41 | Et | 2 | H | 2-CF<sub>3</sub> | H | CH | CH | ||
4-42 | Et | 2 | 4-Cl | 2-CF<sub>3</sub> | H | CH | CH | ||
4-43 | Et | 2 | 4-Br | 2-CF<sub>3</sub> | H | CH | CH | ||
4-44 | Et | 2 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-45 | Et | 2 | 5-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH |
[表4-2]
化合物编号 | R | n | Xm | Y<sub>p</sub> | Z | W<sup>1</sup> | W<sup>2</sup> | 形状 | 熔点(℃) |
4-46 | Et | 2 | H | 2-CF<sub>3</sub> | Me | CH | CH | ||
4-47 | Et | 2 | H | 2-CF<sub>3</sub> | Cl | CH | CH | ||
4-48 | Et | 2 | H | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-49 | Et | 2 | H | 2-CF<sub>3</sub> | I | CH | CH | ||
4-50 | Et | 2 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
4-51 | Et | 2 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
4-52 | Et | 2 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
4-53 | Et | 2 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
4-54 | Et | 2 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH | ||
4-55 | n-Hex | 0 | H | H | H | CH | CH | ||
4-56 | n-Hex | 0 | H | 2-CF<sub>3</sub> | H | CH | CH | ||
4-57 | n-Hex | 0 | 4-Cl | 2-CF<sub>3</sub> | H | CH | CH | ||
4-58 | n-Hex | 0 | 4-Br | 2-CF<sub>3</sub> | H | CH | CH | ||
4-59 | n-Hex | 0 | 4-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-60 | n-Hex | 0 | 5-CF<sub>3</sub> | 2-CF<sub>3</sub> | H | CH | CH | ||
4-61 | n-Hex | 0 | H | 2-CF<sub>3</sub> | Me | CH | CH | ||
4-62 | n-Hex | 0 | H | 2-CF<sub>3</sub> | Cl | CH | CH | ||
4-63 | n-Hex | 0 | H | 2-CF<sub>3</sub> | Br | CH | CH | ||
4-64 | n-Hex | 0 | H | 2-CF<sub>3</sub> | I | CH | CH | ||
4-65 | n-Hex | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | H | CH | CH | ||
4-66 | n-Hex | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Me | CH | CH | ||
4-67 | n-Hex | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Cl | CH | CH | ||
4-68 | n-Hex | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | Br | CH | CH | ||
4-69 | n-Hex | 0 | H | 2,5-(CF<sub>3</sub>)<sub>2</sub> | I | CH | CH |
接下来,详细描述本发明的1,2,3-三唑衍生物(1)的制备方法。顺便说一下,对于反应装置,除了使用磁力搅拌器或机械搅拌器之外,还可以使用微波合成装置进行反应。
<制备方法1>
[式3]
(R,n,X,m,W1,W2和Q与式(1)中的R、n、X、m、W1、W2和Q具有相同的含义,Z1表示氢原子或卤素原子)。
步骤-1是通过式(2)代表的叠氮衍生物与式(3)代表的乙炔衍生物反应生成1,2,3-三唑衍生物(1a)的步骤。式(2)代表的叠氮衍生物与式(3)代表的乙炔衍生物根据本案是已知且可以得到的,例如,可以从东京化学工业有限公司(Tokyo Chemical Industry Co.,Ltd.)购得。或者这些衍生物也可容易的通过在Experimental Chemistry Course、OrganicSyntheses等中描述的已知方法,以现有试剂反应得到。
在该反应中,衍生物必须在含一价或二价铜试剂的存在下反应,铜试剂的具体实例包括氯化铜(I)、氯化铜(II)、溴化铜(I)、溴化铜(II)、碘化铜(I)、乙酸铜(I)、乙酸铜(II)、氢氧化铜(II)、三氟甲磺铜(I)、2-噻吩甲酸铜(I)、硫酸铜(II)。根据情况,可能需要与还原剂如抗坏血酸钠进行组合。衍生物以相对于底物(2)为0.01到1当量的量使用这样的铜试剂进行反应,从而可以有效地获得目标化合物。反应物(3)通常以相对于底物(2)为1到5当量的量进行使用。
上述反应既可以在没有溶剂的情况下进行,也可以在溶剂存在下进行。作为所使用的溶剂,可使用没有不利影响反应的溶剂,并且可以使用芳香族烃类溶剂如苯、甲苯、二甲苯和氯苯,脂肪烃类溶剂如戊烷、己烷和辛烷,醚类溶剂如二乙醚、二异丙基醚、环戊基甲基醚、四氢呋喃、二甲氧基乙烷和1,4-二噁烷,酮如丙酮、甲乙酮和环己酮,卤素类溶剂如氯仿和二氯甲烷,腈类溶剂如乙腈和丙腈,酯类如乙酸乙酯、乙酸正丙酯、乙酸正丁酯和丙酸甲酯,酰氨类溶剂如N,N'-二甲基甲酰胺、N,N'-二甲基乙酰胺和N-甲基吡咯烷酮,醇类溶剂如甲醇、乙醇、1-丙醇、2-丙醇和叔丁醇、二甲基亚砜,水,或其混合溶剂。
反应可在-78℃到200℃范围中合适选择的温度条件下进行,尽管这可以根据反应条件变化。反应完成后,目标化合物可以通过进行正常的后处理操作获得,但是,若需要,则可以通过柱色谱、重结晶等方法纯化得到化合物。
另外,当Z1为H时,所得到的1,2,3-三唑衍生物可在碱如丁基锂或二异丙基氨化锂的存在下与亲电子试剂反应,从而得到所需的5-取代的-1,2,3-三唑衍生物。
<制备方法2>
[式4]
(R,n,X,m,W1,W2和Q具有与公式(1)中的R、n、X、m、W1、W2和Q相同的含义)。
步骤-2是通过式(2)表示的叠氮衍生物与式(4)表示的取代的乙腈衍生物反应生成5-氨基-1,2,3-三唑衍生物(1b)的步骤。式(4)代表的取代的乙腈衍生物根据本申请是已知且可以从东京化学工业有限公司(Tokyo Chemical Industry Co.,Ltd.)购得。或者,衍生物也可容易地通过在Experimental Chemistry Course、Organic Syntheses等中所描述的已知方法,从现有试剂反应得到。
该反应必须在碱的存在下进行,并且可选用的碱包括例如有机碱如三乙胺、二异丙基乙胺、三(正丁基)胺、N-甲基吗啉、N,N'-二甲基苯胺、N,N'-二乙基苯胺、4-叔丁基-N,N'-二甲基苯胺、吡啶、甲基吡啶和二甲基吡啶,以及碱金属盐如碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、乙酸钠、醋酸钾、甲醇钠、乙醇钠、叔丁醇钾、氢化钠、氢化钾、氨化钠、正丁基锂、叔丁基锂、二异丙基氨化锂、二甲基硅锂(trimethylsilyl lithium)和双三甲基硅基胺基锂(lithium hexamethyldisilazide)。在这些碱中,为了良好的产率,优选金属碱如甲醇钠和乙醇钠。上述衍生物以相对于底物为0.1到5当量的量使用所述碱进行反应,从而可以有效地获得目标化合物。反应物(4)通常以相对于底物(2)为1到5当量的量进行使用。
上述反应既可以在没有溶剂的情况下进行,也可以在溶剂存在下进行。作为所使用的溶剂,可使用没有不利影响反应的溶剂,以及可以使用芳香族烃类溶剂如苯、甲苯、二甲苯和氯苯,脂肪烃类溶剂如戊烷、己烷和辛烷,醚类溶剂如二乙醚、二异丙基醚、环戊基甲基醚、四氢呋喃、二甲氧基乙烷和1,4-二噁烷,酮如丙酮、甲乙酮和环己酮,卤素类溶剂如氯仿和二氯甲烷,腈类溶剂如乙腈和丙腈,酯类溶剂如乙酸乙酯、乙酸正丙酯、乙酸正丁酯和丙酸甲酯,酰氨类溶剂如N,N'-二甲基甲酰胺、N,N'-二甲基乙酰胺和N-甲基吡咯烷酮,醇类溶剂如甲醇、乙醇、1-丙醇、2-丙醇和叔丁醇、二甲基亚砜,水,或其混合溶剂。
反应可在-78℃到200℃范围中合适选择的温度条件下进行,尽管这可以根据所使用的碱或反应条件变化。反应完成后,目标化合物可以通过进行正常的后处理操作获得,但是,若需要,则可以通过柱色谱、重结晶等方法纯化得到化合物。
另外,所得到的5-氨基-1,2,3-三唑衍生物可以与亲电试剂反应,并从而得到5-取代的氨基-1,2,3-三唑衍生物。
<制备方法3>
[式5]
(R,n,X,m,W1,W2和Q具有与公式(1)中的R,n,X,m,W1,W2和Q相同的含义,R2表示可被取代的苯基,或C1-C6烷基)。
步骤-3是在碘的存在下由式(5)表示的苯胺衍生物、由式(6)表示的乙酰基衍生物与由式(7)表示的取代的磺酰肼衍生物生成1,2,3-三唑衍生物(1c)的步骤。由式(5)表示的苯胺衍生物、由式(6)表示的乙酰基衍生物和由式(7)表示的取代的磺酰肼衍生物根据本案是已知的且可以得到的,例如,可以从东京化学工业有限公司(Tokyo Chemical IndustryCo.,Ltd.)购得。或者这些衍生物也可容易的通过在Experimental Chemistry Course、Organic Syntheses等中描述的已知方法,以现有试剂反应得到。在该步骤中,可以按照文献(Chemistry A European Journal,(2014),20,17635-17639)中描述的方法进行合成。
另外,所得到的1,2,3-三唑衍生物可在碱如丁基锂或二异丙基氨化锂的存在下与亲电子试剂反应,从而得到所需的5-取代的-1,2,3-三唑衍生物。
<制备方法4>
[式6]
(R,n,X,m,W1,W2和Q与式(1)中的R,n,X,m,W1,W2和Q含义相同,R2表示可被取代的苯基或C1-C6烷基,R11表示氢原子、C1-C6烷基或C1-C6环烷基)。
步骤-4是由式(8)表示的酮衍生物和由式(7)表示的取代的磺酰肼衍生物反应且然后在乙酸铜存在下与式(5)表示的苯胺衍生物反应生成1,2,3-三唑衍生物(1d)的步骤。在这个步骤中,也可以按照文献(Chemistry A European Journal,(2014),20,13692-13697)中描述的方法进行合成。
<制备方法5>
[式7]
(R,n,X,m,W1,W2和Q具有与式(1)中的R、n、X、m、W1、W2和Q相同的含义,而M表示卤素原子或烷基磺酰基)。
步骤-5是将式(1e)表示的三唑衍生物与式(5a)反应生成1,2,3-三唑衍生物(1c)的步骤。
该反应优选在碱的存在下进行,并且可使用的碱包括,例如,有机碱如三乙胺、二异丙基乙胺、三丁基胺、N-甲基吗啉、N,N'-二甲基苯胺、N,N'-二乙基苯胺、4-叔丁基-N,N'-二甲基苯胺、吡啶、甲基吡啶和二甲基吡啶,以及碱金属盐如碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、乙酸钠、醋酸钾、甲醇钠、乙醇钠、叔丁醇钾、氢化钠、氢化钾、氨化钠、丁基锂、叔丁基锂、二异丙基氨化锂、二甲基硅锂和双三甲基硅基胺基锂。在这些碱中,为了良好的产率,优选金属碱如甲醇钠和乙醇钠。上述衍生物以相对于底物为1到5当量的量使用所述碱进行反应,从而可以有效地获得目标化合物。
上述反应既可以在没有溶剂的情况下进行,也可以在溶剂存在下进行。作为溶剂,可使用没有不利影响反应的溶剂,以及可以使用芳香族烃类溶剂如苯、甲苯、二甲苯和氯苯,脂肪烃类溶剂如戊烷、己烷和辛烷、醚类溶剂如二乙醚、二异丙基醚、环戊基甲基醚、四氢呋喃、二甲氧基乙烷和1,4-二噁烷,酮如丙酮、甲乙酮和环己酮,卤素类溶剂如氯仿和二氯甲烷,腈类溶剂如乙腈和丙腈,酯类溶剂如乙酸乙酯、乙酸正丙酯、乙酸正丁酯和丙酸甲酯,酰氨类溶剂如N,N'-二甲基甲酰胺、N,N'-二甲基乙酰胺和N-甲基吡咯烷酮,醇类溶剂如甲醇、乙醇、1-丙醇、2-丙醇和叔丁醇、二甲基亚砜,水,或其混合溶剂。
反应可在-78℃到200℃范围中合适选择的温度条件下进行,尽管这可以根据所使用的碱或反应条件变化。反应完成后,目标化合物可以通过进行正常的后处理操作获得,但是,若需要,则可以通过柱色谱、重结晶等方法纯化得到化合物。
<制备方法6>
[式8]
(R、X、m、W1、W2和Q与式(1)中的R、X、m、W1、W2和Q具有相同的含义,而M在与式(5a)中M具有相同的含义)。
步骤-6是将式(1f)表示的三唑衍生物与由式(8)表示的硫醇反应生成1,2,3-三唑衍生物(1g)的步骤。
该反应优选在碱的存在下进行,并且可使用的碱包括,例如,有机碱如三乙胺、二异丙基乙胺、三丁基胺、N-甲基吗啉、N,N'-二甲基苯胺、N,N'-二乙基苯胺、4-叔丁基-N,N'-二甲基苯胺、吡啶、甲基吡啶和二甲基吡啶,以及碱金属盐如碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾、乙酸钠、醋酸钾、甲醇钠、乙醇钠、叔丁醇钾、氢化钠、氢化钾、氨化钠、丁基锂、叔丁基锂、二异丙基氨化锂、二甲基硅锂和双三甲基硅基胺基锂。在这些碱中,为了良好的产率,优选金属碱如甲醇钠和乙醇钠。反应以相对于底物为1到5当量的量使用所述碱进行,,从而可以有效地获得目标化合物。根据情况,制备化合物(8)的硫醇盐并然后反应。
此外,该反应也可以在过渡金属催化剂如铜、钯、铑和钌的存在下进行,以得到化合物(1g)。作为过渡金属催化剂,可以使用碘化铜(I)碘或三(二苯亚甲基丙酮)二钯(0)。
上述反应既可以在没有溶剂的情况下进行,也可以在溶剂存在下进行。作为溶剂,可使用没有不利影响反应的溶剂,以及可以使用芳香族烃类溶剂如苯、甲苯、二甲苯和氯苯,脂肪烃类溶剂如戊烷、己烷和辛烷、醚类溶剂如二乙醚、二异丙基醚、环戊基甲基醚,四氢呋喃、二甲氧基乙烷和1,4-二噁烷,酮如丙酮、甲乙酮和环己酮,卤素类溶剂如氯仿和二氯甲烷,腈类溶剂如乙腈和丙腈,酯类溶剂如乙酸乙酯、乙酸丙酯、乙酸丁酯和丙酸甲酯,酰氨类溶剂如N,N'-二甲基甲酰胺、N,N'-二甲基乙酰胺和N-甲基吡咯烷酮,醇类溶剂如甲醇、乙醇、1-丙醇、2-丙醇和叔丁醇、二甲基亚砜,水,或其混合溶剂。
反应可在-78℃到200℃范围中合适选择的温度条件下进行,尽管这可以根据所使用的碱或反应条件变化。反应完成后,目标化合物可以通过进行正常的后处理操作获得,但是,若需要,则可以通过柱色谱、重结晶等方法纯化得到化合物。
<制备方法7>
[式9]
(R、X、m、Z、W1、W2和Q与公式(1)中的R、X、m、Z、W1、W2和Q具有相同的含义,Q表示1到2的整数)。
本发明的式(1i)所表示的化合物可以例如通过式(1h)表示的化合物与氧化剂反应而生成。
该反应中使用的氧化剂,可使用过氧化氢、间氯过氧苯甲酸、高碘酸钠、OXONE(E.I.DuPont的商标名、含过硫酸氢钾的氧化剂)、N-氯琥珀酰亚胺、N-溴代琥珀酰亚胺、叔丁基次氯酸盐、次氯酸钠、氧等。在这些氧化剂中,从产率来看,优选间氯过氧苯甲酸、过氧化氢等。这样的氧化剂优选以相对于底物为0.01至10当量的范围使用,以免对反应的进展产生不利影响,并且进一步优选1至3当量的范围,这是因为目标化合物可以获得良好的产率。
作为该反应所用的催化剂,例如可以使用氧化钼、硼酸、三(乙酰丙酮)铁和钨酸钠等,优选例如氧化钼等。反应中,催化剂以相对于底物(1h)为0.01至1当量的量使用这样的催化剂进行反应,从而可以有效地获得目标化合物。
该反应优选在溶剂中进行。对于溶剂,可使用没有不利影响反应的溶剂,以及可以使用醚基溶剂如二乙醚、四氢呋喃和二噁烷,芳香族烃类溶剂如苯、甲苯、二甲苯和氯苯,腈类溶剂如乙腈和丙腈,酰氨类溶剂如N,N'-二甲基甲酰胺、N,N'-二甲基乙酰胺和N-甲基吡咯烷酮,醇类溶剂如甲醇、乙醇和异丙醇,卤素类溶剂如二氯甲烷、氯仿和1,2-二氯乙烷,脂肪族烃类溶剂如戊烷、己烷、环己烷和环庚烷,酮如丙酮、甲乙酮和环己酮,醇类溶剂如甲醇、乙醇、1-丙醇、2-丙醇和叔丁醇、乙酸、水,或它们的混合溶剂。
根据反应条件和选用碱的不同,反应可在-78℃到溶剂回流温度的范围中合适选择的温度条件下进行,尽管这可以根据反应条件变化。反应完成后,可以通过进行正常的后处理操作获得目标化合物,但是若需要,则可以通过柱色谱、重结晶等方法纯化得到化合物。
本发明化合物,如果需要,可以通过熔点、红外吸收光谱、1H-NMR、13C-NMR、质谱、X射线结构分析等进行分析、确认或鉴定。
本发明化合物可用作农业/园艺害虫防治剂的活性成分,或杀虫剂或杀螨剂。
本发明化合物还可以在控制种类繁多的昆虫、螨虫、甲壳纲动物、软体动物和线虫中发挥优异的活性。农业/园艺的害虫的具体实例包括:
例如,缨尾目昆虫,例如,敏栉衣鱼(ctenolepisma villosa)、蠹鱼(Lepismasaccharina)和斑衣鱼(Thermobia domestica),
蜚蠊目昆虫,例如,美洲大蠊(Periplaneta americana)、黑胸大蠊(Periplanetafuliginosa)、日本大蠊(Periplaneta japonica)、德国小蠊(Periplaneta germanica)和拟德国小蠊(Periplaneta lituricollis),
等翅目昆虫,例如小须眉(Incisitermes minor)、台湾家白蚁(Coptotermesformosanus)、西北散白蚁(Reticulitermes speratus)、黑翅土白蚁(odontotermesformosanus)等,
直翅目昆虫,例如黑胫钩额螽(Ruspolia lineosa)、黄脸油葫芦(Teleogryllusemma)、东方蝼蛄(Gryllotalpa orientalis)、飞蝗(Locusta migratoria)和小翅稻蝗(Oxya yezoensis),
啮目昆虫,例如书虱(Trogium pulsatorium)、嗜卷书虱(Liposcelisbostrychophila)和雕纹书虱(Liposcelis corrodens),
食毛目昆虫,例如鸡翅长鸟虱(Lipeurus caponis)、火鸡领鸟虱(Menacanthusstramineus)、牛毛虱(Damalinia bovis)和山羊毛虱(Damalinia caprae),
虱目昆虫,例如牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinussuis)、头虱(Pediculus humanus capitis)、体虱(Pediculus humanus humanus)、和阴虱(Pthirus pubis),
缨翅目昆虫,例如花蓟马(Frankliniella intonsa)、西花蓟马(Frankliniellaoccidentalis)、温室蓟马(Heliothrips haemorrhoidalis)、豆喙蓟马(Mycterothripsglycines)、茶黄蓟马(Scirtothrips dorsalis)、稻蓟马(Stenchaetothrips biformis)、棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci)、稻管蓟马(Haplothrips aculeatus)和Ponticulothrips diospyrosi,
半翅目昆虫,例如葡萄斑叶蝉(Arboridia apicalis)、小贯小绿叶蝉(Empoascaonukii)、黑尾叶蝉(Nephotettix cincticeps)、灰飞虱(Laodelphax striatella)、褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatella furcifera)、青蛾蜡蝉(Geishadistinctissima)、柑橘木虱(Diaphorina citri)、葡萄根瘤蚜(Viteus vitifoliae)、碗豆长管蚜(Acyrthosiphon pisum)、苜蓿蚜(Aphis craccivora)、棉蚜(Aphis gossypii)、苹果黄蚜(Aphis pomi)、绣线菊蚜(Aphis spiraecola)、茄沟无网蚜(Aulacorthum solani)、苹果绵蚜(Eriosoma lanigerum)、Hyalopterus pruni、菜缢管蚜(Lipaphis erysimi)、桃蚜(Myzus persicae)、禾谷缢管蚜(Rhopalosiphum padi)、麦二叉蚜(Schizaphisgraminum)、梨二叉蚜(Schizaphis piricola)、茶二叉蚜(Toxoptera aurantii)、褐色橘蚜(Toxoptera citricida)、柑橘刺粉虱(Aleurocanthus spiniferus)、银叶粉虱(Bemisiaargentifolii)、烟粉虱(Bemisia tabaci)、柑橘粉虱(Dialeurodes citri)、温室粉虱(Trialeurodes vaporariorum)、草履蚧(Drosicha corpulenta)、吹绵介壳虫(Iceryapurchasi)、桔粉介壳虫(Planococcus citri)、日本臀纹粉蚧(Planococcus kraunhiae)、康氏粉蚧(Pseudococcus comstocki)、角蜡蚧(Ceroplastes ceriferus)、红蜡蚧(Ceroplastes rubens)、红圆蚧(Aonidiella aurantii)、梨笠圆盾蚧(Diaspidiotusperniciosus)、桑白盾蚧(Pseudaulacaspis pentagona)、柑桔矢尖蚧(Unaspisyanonensis)、花肢淡盲蝽(Creontiades coloripes)、Trigonotylus caelestialium、梨冠网蝽(Stephanitis nashi)、杜鹃网蝽(Stephanitis pyrioides)、北二星蝽(Eysarcorisaeneus)、Eysarcoris lewisi、青蝽(Glaucias subpunctatus)、赤条蝽(Graphosomarubrolineatum)、茶翅蝽(Halyomorpha halys)、黑须稻绿蝽(Nezara antennata)、稻绿蝽(Nezara viridula)、小珀蝽(Plautia crossota stali)、甘蔗长椿(Caveleriussaccharivorus)、Togo hemipterus、中华稻缘椿(Leptocorisa chinensis)、点蜂缘椿象(Riptortus clavatus)、稻棘缘蝽(Cletus punctiger)、胡萝卜缘蝽(Rhopalusmaculatus)和温带臭虫(Cimex lectularis),
鞘翅目昆虫,例如小青铜金龟(Anomala albopilosa)、古铜丽金龟(Anomalacuprea)、多色异丽金龟(Anomala rufocuprea)、花金龟(Eucetonia pilifera)、小青花金龟(Gametis jucunda)、沥青七触金龟(Heptophylla picea)、日本弧丽金龟(Popilliajaponica)、Agriotes ogurae fuscicollis、脊胸筒叩甲(Ectinus sericeus)、Melanotusfortnumi fortnumi、小圆皮蠹(Anthrenus verbasci)、烟草甲(Lasioderma serricorne)、大谷盗(Tenebroides mauritanicus)、Epuraea domina、墨西哥大豆瓢虫(Epilachnavarivestis)、茄二十八星瓢蟲(Henosepilachna vigintioctopunctata)、黄粉虫(Tenebrio molitor)、赤拟谷盗(Tribolium castaneum)、紫薇星天牛(Anoplophoramalasiaca)、松墨天牛(Monochamus alternatus endai)、虎天牛(Xylotrechuspyrrhoderus)、绿豆象(Callosobruchus chinensis)、黄足黄守瓜(Aulacophorafemoralis)、甜菜大龟甲(Cassida nebulosa)、甜菜跳甲(Chaetocnema concinna)、玉米根萤叶甲(Diabrotica virgifera virgifera)、黄瓜十一星叶甲(Diabroticaundecimpunctata howardi)、根萤叶甲属(Diabrotica spp.)、马铃薯甲虫(Leptinotarsadecemlineata)、水稻负泥甲(Oulema oryzae)、黄曲条跳甲(Phyllotreta Striolata)、甘薯蚁象甲(Cylas formicarius)、棉铃象甲(Anthonomus grandis)、西印度甘薯象甲(Euscepes postfasciatus)、苜蓿叶象甲(Hypera postica)、蔬菜叶象甲(Listroderescostirostris)、稻象甲(Echinocnemus bipunctatus)、稻水象甲(Lissorhoptrusoryzophilus)、玉米象甲(Sitophilus zeamais)、草皮步行象甲(Sphenophrus venatusvestitus)、纵坑切梢小蠹(Tomicus piniperda)和褐粉蠹(Lyctus brunneus),
膜翅目类,例如月季叶蜂(Arge pagana)、短斑残青叶蜂(Athalia rosaeruficornis)、栗瘿蜂(Dryocosmus kuriphilus)、黄翅蜂(Vespa simillimaxanthoptera)、台湾蚁(Formica japonica)、法老蚁(Monomorium pharaonis)和红火蚁(Solenopsis invicta),
螨虫类,例如大蜂螨(Varroa jacobsoni)、鸡皮刺螨(Dermanyssus gallinae)、柏氏禽刺螨(Ornithonyssus bacoti)、猴耳螨(Ornithonyssus sylvialum)、钝眼蜱属(Amblyomma spp.)、微小牛蜱(Boophilus microplus)、矩头蝉属(Dermacentor spp.)、褐黄血蜱(Haemaphysalis flava)、铃头血蜱(Haemaphysalis campanulata)、长角血蜱(Haemaphysalis longicornis)、卵形硬蜱(Ixodes ovatus)、全沟硬蜱(Ixodespersulcatus)、红扇头蜱(Rhipicephalus sanguineus)、Penthaleus erythrocephalus、麦圆叶爪螨(Penthaleusmajor)、白狭跗线螨(Phytonemus pallidus)、茶跗线螨(Polyphagotarsonemus latus)、Tarsonemus bilobatus、犬脂螨(Demodex canis)、猫脂螨(Demodex cati)、甘蔗黄蜘蛛(Oligonychus shinkajii)、柑桔全爪螨(Panonychuscitri)、Panonychus mori、榆全爪螨(Panonychus ulmi)、朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychus kanzawai)、二斑叶螨(Tetranychus urticae)、荼尖叶节蜱(Acaphylla theavagrans)、Aceria tulipae、番茄刺皮瘿螨(Aculopslycopersici)、橘刺皮瘿螨(Aculops pelekassi)、苹果锈螨(Aculus schlechtendali)、茶叶瘿螨(Calacarus carinatus)、梨上瘿螨(Epitrimerus pyri)、中国瘿螨(Eriophyeschibaensis)、柑橘锈螨(Phyllocoptruta oleivora)、罗宾根螨(Rhizoglyphusrobini)、腐食酪螨(Tyrophagus putrescentiae)、类食酪螨(Tyrophagus similis)、疥螨属(Knemidokoptes spp.)、羊痒螨(Psoroptes ovis)、猫背肛螨(Notoedres.Cati)、人疥螨(Sarcoptes scabiei)、纤恙螨(Leptotrombidium akamushi)、布氏姬螯螨(Cheyletiellablakei)、牙氏姬螯螨(Cheyletiella yasguri)、粉尘螨(Dermatophagoides farinae)和红背蜘蛛(Latrodectus hasseltii);
条马陆目甲壳纲,例如温室马陆(Oxidus gracilis),
等足目,例如鼠妇(Armadillidium vulgare),
十足目,例如克氏原螯虾(Procambarus clarkia),
弹尾目,例如Bourletiella hortensis;
古扭舌(Architaenioglossa)目,例如福寿螺(Pomacea canaliculata),和
肺螺亚纲昆虫,例如非洲大蜗牛(Achatina fulica)、双线蛞蝓(Meghimatiumbilineatum)、Lehmannina valentiana、Acusta despecta sieboldiana;
垫刃目线虫,例如草莓线虫(Nothotylenchus acris)、南方根瘤线虫(Meloidogyne incognita)、马铃薯金线虫(Globodera rostochiensis)、大豆胞囊线虫(Heterodera glycine)、半穿刺线虫(Tylenchulus semipenetrans)、咖啡短体线虫(Pratylenchus coffeae)、燕麦真滑刃线虫(Aphelenchus avenae)、水稻干尖线虫(Aphelenchoides besseyi)和松材线虫(Bursaphelenchus xylophilus);
此外,害虫还包括动物中的体内寄生虫,如蛔虫、蛲虫、丝虫、肝片吸虫、肺吸虫(pulmonary distomiasis)、横川后殖吸虫(metagonimus yuokogawa)、日本血吸虫(Schistosoma japonicum)、猪肉绦虫(Taenia solium)、牛肉绦虫(Taenia saginata)、多房棘球绦虫(Echinococcus multilocularis)和阔节裂头绦虫(diphyllobothriumlatum)。
本发明化合物可作为农业/园艺害虫控制成分使用。在配制时,PesticideFormulation Guide(农药制剂指南)(由日本农药科学协会、农业制剂和应用委员会编辑,日本植物保护协会发行)中所描述的合适的载体、佐剂、表面活性剂、粘合剂、稳定剂等也可混合使用。
含有本发明化合物的农业/园艺害虫防治剂可以配制成日常农业/园艺害虫防治剂形式通常采用的任意形状。例如,害虫防治剂可以配制成常用形式,如粉尘、粗粉尘、DL(无漂移型)粉尘、流动粉尘、微粒、细颗粒、颗粒、可湿性粉剂、颗粒状可湿性粉剂、液体制剂、溶胶(可流动制剂)、可乳化浓缩剂和油溶液,且制剂不仅限于此。
本发明化合物的含量可以根据制剂形式和使用方法适当选择。一般而言,相对于制剂的总量,含量优选为0.0001~90wt%。
在使用本发明化合物作为农业/园艺害虫防治剂的情况下,一种或多种选自杀菌剂(杀霉剂、杀菌剂、抗病毒剂、植物抗性诱导剂)、杀虫剂、杀螨剂、杀线虫剂、除草剂、驱鸟剂、植物调节剂、肥料、土壤调节剂等的可选成份可以混合,如果需要在配制或喷涂时混合以提供混合制剂,或者可以在喷涂时作为罐混物(tankmix)施用。
在上述可选成分中,下面描述杀菌剂和杀虫剂或杀螨剂的代表性实例,但本发明不限于此。
杀真菌剂:
(1)铜试剂
碱性氯化铜(氯氧化铜)、碱性硫酸铜(硫酸铜)、氢氧化铜(氢氧化铜)、硫酸铜、羟基喹啉铜、壬基苯磺酸铜、DBEDC,等。
(2)无机杀真菌剂
硫、石灰-硫混合物(多硫化钙)、碳酸氢钠、碳酸氢钾、金属银(银)等。
(3)有机硫杀真菌剂
福美锌(Ziram)、代森锰(maneb)、代森锰锌(mancozeb)、代森铵(ambam)、聚氨基甲酸酯、丙森锌(propineb)、秋兰姆、噻嗪类、代森锌(zineb),等。
(4)有机磷杀真菌剂
IBP、EDDP、tolclofos-methyl、定菌磷、fosetyl(fosetyl-alminium)等。
(5)苯并咪唑杀真菌剂
多菌灵(Carbendazim)、噻苯达唑、甲基硫菌灵(thiophanate-methyl)、苯菌灵(benomyl)等。
(6)二甲酰胺类杀真菌剂
扑海因(Iprodione)、腐霉利(procymidone)、农利灵(vinclolin)等。
(7)甲酰胺杀真菌剂
氧化萎锈灵(oxycarboxin)、萎锈灵(carboxin)、灭锈胺(mepronil)、氟酰胺(flutolanil)、啶酰菌胺(boscalid)、氟吡菌酰胺(fluopyram)、呋吡菌胺(furametpyr)、噻呋酰胺(thifluzamide)、吡噻菌胺(penthiopyrad)、联苯吡菌胺(bixafen)、氟唑菌苯胺(penflufen)、氟唑菌酰胺(Fluxapyroxad)、吡唑萘菌胺(isopyrazam)、唑虫酰胺(Tolfenpyrad)、环苯吡菌胺(Sedaxane)等。
(8)苯基酰胺类杀真菌剂
甲霜灵(Metalaxyl)、精甲霜灵(metalaxyl-M)、噁霜灵(oxadixyl)、呋霜灵(furalaxyl)、呋酰胺(ofurace)、苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)等;
(9)羧酸酰胺杀真菌剂
烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、异丙菌胺(iprovalicarb)、苯噻菌胺酯(benthiavalicarb-isopropyl)、双炔酰菌胺(mandipropamid)、缬菌胺(valifenalate)等;
(10)SBI试剂
氟菌唑(triflumizole)、咪酰胺(prochloraz)、咪唑富马酸盐(oxpoconazolefumarate)、三唑酮(triadimefon)、双苯三唑醇(bitertanol)、腈菌唑(myclobutanil)、腈苯唑(fenbuconazole)、己唑醇(hexaconazole)、戊唑醇(tebuconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、苯醚甲环唑(difenoconazole)、种菌唑(ipconazole)、亚胺唑(imibenconazole)、环唑醇(cyproconazole)、四氟醚唑(tetraconazole)、硅氟唑(simeconazole)、叶菌唑(metconazole)、氟环唑(epoxiconazole)、氟硅唑(flusilazole)、抑霉唑(imazalil)、氯苯嘧啶醇(fenarimol)、嗪胺灵(triforine)、三唑醇(Triadimenol)、粉唑醇(flutriafol)、啶斑肟(pyrifenox)、十三吗啉(tridemorph)、十二环吗啉(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、螺环菌胺(spiroxamine)、氯啶菌酯(pyrisoxazole)、环酰菌胺(fenhexamid)、稗草丹(pyributicarb)等。
(11)甲氧基丙烯酸酯类杀真菌剂
嘧菌酯(Azoxystrobin)、醚菌酯(kresoxim-methyl)、肟菌酯(trifloxystrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、吡唑醚菌酯(pyraclostrobin)、烯肟菌酯(enestroburin)、醚菌胺(dimoxystrobin)、啶氧菌酯(picoxystrobin)、百克敏(pyribencarb)、氟嘧菌酯(fluoxastrobin)等。
(12)苯胺并嘧啶杀真菌剂
嘧菌环胺(Cyprodinil)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil)等。
(13)苯基吡咯杀真菌剂
咯菌酯(Fludioxonil)、拌种咯(fenpiclonil)等。
(14)抗生素杀真菌剂
春日霉素(Kasugamycin)、多抗霉素(polyoxin)、井冈霉素(validamycin)、链霉素(streptomycin)、土霉素(oxytetracycline)、杀稻瘟菌素(blasticidin-S)等。
(15)其他杀真菌剂
DKF-1001(代号),IKF-5411(代号),MIF-1002(代号),NC-233(代号),S-2200(代号),SB-4303(代号)、苯并噻二唑(acibenzolar-S-methyl)、吲唑磺菌胺(amisulbrom)、唑嘧菌胺(ametoctradin)、异噻菌胺(isotianil)、稻瘟灵(isoprothiolane)、烷苯磺酸盐((iminoctadine-albesilate)双胍三辛烷基苯磺酸盐(iminoctadine tris(albesilate))、双胍辛胺乙酸盐((iminoctadine acetate)双胍辛胺三乙酸酯(iminoctadine triacetate))、氯唑灵(echlomezol)、噻唑菌胺(ethaboxam)、奥索利酸(oxolinic acid)、敌菌丹(captafol,)、环丙酰菌胺(carpropamid)、喹氧灵(quinoxyfen)、灭螨猛(chinomethionat)、克菌丹(captan)、地茂散(chloroneb)、百菌清(chlorothalonil)、氰霜唑(cyazofamid)、乙霉威(diethofencarb)、双氯氰菌胺(diclocymet)、哒菌清(diclomezine)、二噻农(dithianon)、环氟菌胺(cyflufenamid)、氟嘧菌胺(diflumetorim)、霜脲氰(cymoxanil)、硫硅菌胺(silthiofam)、苯酰菌胺(zoxamide)、棉隆(dazomet)、噻酰菌胺(tiadinil)、叶枯酞(teclofthalam)、异丁乙氧喹啉(tebufloquin)、多果定(dodine)、咪唑嗪(triazoxide)、三环唑(tricyclazole)、甲磺菌胺(tolnifanide)、土菌消(hydroxyisoxazole)、吡氟草酮(Pyriofenone)、咯喹酮(pyroquilon)、氰菌胺(fenoxanil)、嘧菌胺(ferimzone)、胺苯吡菌酮(fenpyrazamine)、苯酞(phthalide)、乙嘧酚磺酸酯(bupirimate)、噁唑菌酮(famoxadone)、咪唑菌酮(fenamidone)、氟啶胺(fluazinam)、氟吡菌胺(fluopicolide)、唑呋草(fluoroimide)、磺菌胺(flusulfamide)、氟噻唑菌腈(flutianil)、丙氧喹啉(proquinazid)、霜霉威盐酸盐(propamocarb hydrochloride)、噻菌灵(probenazole)、戊菌隆(pencycuron)、灭菌丹(folpet)、磺菌威(methasulfocarb)、苯菌酮(metrafenone)、昆布多糖(laminarin)等。
杀虫剂:
(1)有机磷杀虫剂
乙酞甲胺磷(acephate)、甲基谷硫磷(azinphos-methyl)、毒虫畏(chlorfenvinphos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、杀螟腈(cyanophos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorvos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、丙线磷(ethoprophos)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、异丙胺磷(isofenphos)、恶唑磷(isoxathion)、马拉硫磷(malathion)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、乙酰甲胺磷(oxydemeton-methyl)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基吡啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、敌百虫(trichlorfon)、蚜灭磷(vamidothion)等。
(2)氨基甲酸酯杀虫剂
涕灭威(Aldicarb)、棉铃威(alanycarb)、恶虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、苯氧威(fenoxycarb)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimor)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate)、灭除威(XMC)、灭杀威(xylylcarb)等。
(3)拟除虫菊酯杀虫剂
氟丙菊酯(Acrinathrin)、丙烯菊酯(allethrin)、联苯菊酯(bifenthrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、超高效三氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、顺式氯氰菊酯(alpha-cypermethrin)、反式氯氰菊酯(theta-cypermethrin)、溴氰菊酯(deltamethrin)、顺式氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氯氟胺氰戊菊酯(fluvalinate)、氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(permethrin)、醚菊酯((phenothrin)苯醚菊酯(1R-反式异构体)(phenothrin(1R-trans-isomer))、除虫菊酯(pyrethrins)、苄呋菊脂(resmethrin)、氟硅菊脂(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)等。
(4)沙蚕毒素杀虫剂
杀虫磺(Bensultap)、杀螟丹(cartap)、杀虫环(thiocyclam)等。
(5)新烟碱类杀虫剂
啶虫脒(Acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)等。
(6)二酰胺类杀虫剂
氯虫苯甲酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)、氟虫酰胺(flubendiamide)、环溴虫酰胺(cyclaniliprole)等。
(7)苯基吡唑杀虫剂
乙酰虫腈(acetoprole)、乙虫腈(ethiprole)、氟虫腈(fipronil)、丁烯氟虫腈(flufiprole)、吡嗪氟虫腈(pyrafluprole)、吡唑虫啶(pyriprole)等。
(8)大环内酯物杀虫剂
阿巴菌素(Abamectin)、阿维菌素(Avermectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)、密灭汀(milbemectin)、乙基多杀菌素(spinetoram)、多杀菌素(spinosad)等。
(9)苯甲酰脲杀虫剂
双三氟虫脲(Bistrifluron)、氟啶脲(chlorfluazuron)、除虫脲(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)、杀铃脲(triflumuron)等。
(10)二酰基肼杀虫剂
环虫酰肼(Chromafenozide),氯虫酰肼(halofenozide),甲氧虫酰肼(methoxyfenozide),虫酰肼(tebufenozide)等。
(11)其他杀虫剂活性成分
印楝素(Azadiractin)、噻嗪酮(buprofezin)、灭螨猛(chinomethionat)、溴虫腈(chlorfenapyr)、灭蝇胺(cyromazine)、丁醚脲(diafenthiuron)、三氯杀螨醇(dicofol)、除螨灵(dienochlor)、硫丹(endosulfan)、flometquin、氟啶虫酰胺(flonicamid)、嘧虫胺(flufenerim)、氟吡呋喃酮(flupyradifurone)、氟蚁腙(hydramethylnon)、烯虫乙酯(hydroprene)、茚虫威(indoxacarb)、氰氟虫腙(metaflumizone)、聚乙醛(metaldehyde)、烯虫酯(methoprene)、甲氧滴滴涕(methoxychlor)、吡蚜酮(pymetrozine)、啶虫丙醚(pyridalyl)、pyrifluquinazone、吡丙醚(pyriproxyfen)、鱼藤酮(rotenone)、螺虫乙酯(spirotetramat)、氟啶虫胺腈(sulfoxaflor)、唑虫酰胺(tolfenpyrad)、三氟苯嘧啶(triflumezopyrim)、AKD-1193(代号),MIE-1209(代号),NA-89(代号),NC-515(代号),ME5382(代号),ZDI-2501(代号)、油酸钠(sodium oleate)、硅藻土(diatomaceous earth)、甘油脂肪酸酯(fatty acid glyceride)、淀粉(starch)、菜籽油(rapeseed oil)、贴纸(聚丁烯)(sticker(polybutene))、丙二醇单脂肪酸酯(propylene glycol monofatty acidester)、机油(石油)(machine oil(petroleum oil))、硫酸烟碱(nicotine-sulfate)、磷酸铁(ferric phosphate)等。
(12)杀螨剂
灭螨醌(Acequinocyl)、磺胺螨酯(amidoflumet)、双甲脒(amitraz)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、四螨嗪(clofentezine)、腈吡螨酯(cyenopyrafen)、丁氟螨酯(cyflumetofen)、三环锡(cyhexatin)、乙螨唑(etoxazole)、喹螨醚(fenazaquin)、苯丁锡(fenbutatin oxide)、苯硫威(fenothiocarb)、唑螨酯(fenpyroximate)、嘧螨酯(fluacrypyrim)、噻螨酮(hexythiazox)、克螨特(propargite)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、吡螨胺(tebufenpyrad)、三氯杀螨砜(tetradifon)。
(13)杀线虫剂
涕灭砜威(aldoxycarb)、硫线磷(cadusafos)、carbam sodium、1,3-二氯丙烯(1,3-dichloropropene)、二氯异丙醚(DCIP)、联氟砜(fluensulfone)、噻唑膦(fosthiazate)、imicyafos、盐酸左旋咪唑(levamisol hydrochloride)、倍硫磷亚砜(mesulfenfos)、异硫氰酸甲酯(methyl isothiocyanate)、酒石酸甲噻嘧啶(morantel tartrate)、尼莫克汀(nemadectin)等。
(14)其他
病毒试剂如核型多角体病毒(NPV)、颗粒体病毒(GV)、胞质型多角体病毒(CPV)和昆虫痘病毒(EPV);由苏云金芽孢杆菌(Bacillus thuringiesis)产生的活孢子和晶体毒素,及其混合物;微生物杀虫剂、昆虫信息素和昆虫引诱剂。其用作杀昆虫剂或杀线虫剂,如小卷蛾线虫(Steinernema carpocapsae)和穿透巴斯德菌(Pasteuria penetrans);
含有本发明化合物作为活性成分的农业/园艺害虫防治剂可用一般害虫防治剂的方法。具体而言,在可湿性粉剂、液体制剂、可乳化浓缩剂、溶胶(可流动制剂)、颗粒状可湿性粉剂或油溶液的情况下,液体可以如下制备:通过将害虫防治剂稀释50至10000倍以得到活性成分的浓度通常为1至10000ppm,优选为1至1000ppm,所得稀释溶液可以每10a农田50至1000L、通常为100至600L的范围内在植物患病区域的树叶上喷洒,但这可根据作物形态例如水稻或果树而变化。
可替代地,害虫防治剂可以通过空中喷雾施加至农业/园艺害虫,其中用水稀释获得预定活性成分浓度的化学溶液通过直升机(包括RC直升机)喷洒。
在粉尘剂、粗颗粒、DL粉尘剂、流动粉尘、微粒、细粒或颗粒的情况下,可用0.3~50kg/10a(有效成分含量:约5~500g)的害虫防治剂施用在害虫出现的区域,土壤表面、土壤下表面或水面。
在育苗箱中对例如水稻的幼苗进行培育时,可以在播种前或者在播种后和移栽日之间,将颗粒施加至土壤表面或土壤表面下,量为10至100g,且在可流动制剂的情况中,无需稀释直接施用或稀释后施用,量为30至1000mL每育苗箱(标准尺寸:30厘米×60厘米×5厘米)。
实施例:
通过下面1,2,3-三唑衍生物的合成实例、制剂实例和测试实例,更具体地描述本发明,但本发明不限于此。
合成实例1:
(1)2-[3,5-二(三氟甲基)苯基]乙炔基三甲基硅烷的合成
在氮气氛中,将氯化钯(II)(2.4g,13.7mmol),三苯基膦(7.2g,27.3mmol)和碘化铜(I)(4.2g,21.8mmol)依次添加3,5-二(三氟甲基)溴苯(80g,273mmol)的三乙胺(270mL)溶液,并在冰冷却下滴加三甲基甲硅烷基乙炔(32.2g,327.6mmol)。滴加完成后,将溶液在室温下搅拌过夜,并通过硅藻土过滤,滤液在减压下浓缩。随后,加入氨水(30mL)和水,并用己烷萃取所得到的溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:己烷)纯化得到标题化合物(83.1g,收率:98%),为橙色油性产物。
1HNMR谱(CDCI3)σ:7.88(2H,s),7.79(1H,s),0.27(9H,s).
(2)1-乙炔基-3,5-二(三氟甲基)苯的合成
向2-[3,5-二(三氟甲基)苯基]乙炔基三甲基硅烷(83.1g,267.7mmol)的甲醇(70mL)和氯仿(70mL)溶液中,加入碳酸钾(7.4g,53.5mmol),然后在室温下搅拌过夜。减压蒸馏除去溶剂后,将水加入溶液中,用乙醚萃取所得溶液。用饱和盐水洗涤有机层,用硫酸钠干燥,过滤除去白色沉淀物,并在减压下浓缩,粗产物经减压蒸馏(82℃,100毫巴)纯化得到标题化合物(48.7g,收率:76%),为无色油性产品。
1HNMR谱(CDCI3)σ:7.92(2H,s),7.84(1H,s),3.26(1H,s).
(3)2-乙基硫基苯胺的合成
向2-氨基硫酚(15g,119.8mmol)的甲醇(25mL)溶液,添加28%甲醇钠-甲醇溶液(27.7g,143.8mmol),在回流加热下滴加碘乙烷(18.7g,119.8mmol)的甲醇(15mL)溶液。滴加完成后,将溶液加热回流6小时,然后冷却至室温,然后蒸馏出溶剂。将水加入到所得到的反应溶液中,用乙酸乙酯萃取所得溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:20)纯化得到标题化合物(得到17.8g,收率:97%),为橙褐油性产品。
1HNMR谱(CDCI3)σ:7.37(1H,dd,J1=7.6Hz,J2=1.6Hz),7.11(1H,td,J1=7.7Hz,J2=1.8Hz),6.73(1H,dd,J1=8.0Hz,J2=1.1Hz),6.69(1H,td,J1=7.6Hz,J2=1.4Hz),4.34(2H,br),2.76(2H,q,J=7.3Hz),1.23(3H,t,J=7.3Hz).
(4)1-叠氮基-2-乙基硫苯的合成
将2-乙基硫苯胺(17.8g,115.8mmol)的35%盐酸(30mL)和水(30mL)混合溶液冷却至-5℃,滴加亚硝酸钠(9.6g,139.0mmol)水溶液(35mL)。滴加完成后,将所得溶液在-5℃搅拌30分钟,随后滴加叠氮化钠(11.3g,173.7mmol)的水溶液(40mL)。将所得溶液在-5℃下搅拌60分钟,室温下搅拌4小时。用乙酸乙酯萃取反应溶液,用饱和盐水洗涤有机层,用硫酸钠干燥,过滤除去白色沉淀物,并在减压下浓缩。所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:20)纯化得到标题化合物(19.3g,收率:93%),为黄色油状产物。
1HNMR谱(CDCI3)σ:7.30(1H,dd,J1=7.8Hz,J2=1.4Hz),7.24-7.22(1H,m),7.14(1H,dd,J1=7.8Hz,J2=0.9Hz),7.10(1H,td,J1=7.6Hz,J2=1.4Hz),2.94(2H,q,J=7.3Hz),1.32(3H,t,J=7.3Hz).
(5)4-[3,5-二(三氟甲基)苯基)-1-(2-乙基硫苯基)三唑(1-75)的合成
向1-叠氮基-2-乙基硫苯(4.5g,25.2mmol)的叔丁醇(36mL)和水(18mL)混合溶液,依次加入1-乙炔基-3,5-二(三氟甲基)苯(6.0g,25.2mmol),无水硫酸铜(II)(603mg,3.8mmol)和抗坏血酸钠(2g,10.1mmol),接着在室温下搅拌过夜。将水加入到所得到的反应溶液中,用乙酸乙酯萃取得到溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:4)纯化,得到标题化合物(得到10.1g,收率:96%),为黄色固体。
1HNMR谱(CDCI3)σ:8.39(2H,s),8.31(1H,s),7.86(1H,s),7.57-7.49(3H,m),7.40(1H,td,J1=7.6Hz,J2=1.7Hz),2.84(2H,q,J=7.5Hz),1.25(3H,t,J=7.3Hz).
(6)4-[3,5-二(三氟甲基)苯基]-1-(2-乙基亚磺酰苯基)三唑(1-354)的合成
向4-[3,5-二(三氟甲基)苯基]-1-(2-乙基硫苯基)三唑(350.0mg,0.84mmol)的氯仿(3mL)溶液,在冰冷却下添加77%的间氯过苯甲酸(188.0mg,0.84mmol),然后在冰冷却下搅拌2小时。在反应溶液中注入饱和碳酸氢钠水溶液,所得溶液用乙酸乙酯萃取。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:1)纯化得到标题化合物(得到350.2mg,收率:96%),为白色固体。
1HNMR谱(CDCI3)σ:8.38(2H,br),8.34(1H,s),8.27(1H,dd,J1=8.0Hz,J2=1.6Hz),7.91(1H,br),7.80(1H,td,J1=7.7Hz,J2=1.2Hz),7.71(1H,td,J1=7.7Hz,J2=1.5Hz),7.56(1H,dd,J1=7.8Hz,J2=0.9Hz),3.36-3.28(1H,m),2.97-2.88(1H,m),1.37(3H,t,J=7.3Hz).
(7)4-[3,5-二(三氟甲基)苯基]-1-(2-乙基磺酰基苯基)三唑(1-631)的合成
向4-[3,5-二(三氟甲基)苯基]-1-(2-乙基硫苯基)三唑(350.0mg,0.84mmol)的氯仿(3mL)溶液,在冰冷却下添加77%的间氯过苯甲酸(385.3mg,1.7mmol),然后在冰冷却下搅拌2小时。在反应溶液中注入饱和碳酸氢钠水溶液,所得溶液用乙酸乙酯萃取。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:1)纯化得到标题化合物(得到363.1mg,收率:96%),为白色固体。
1HNMR谱(CDCI3)σ:8.37(2H,s),8.34(1H,s),8.29(1H,dd,J1=7.6Hz,J2=1.6Hz),7.88-7.83(3H,m),7.58(1H,dd,J1=7.3Hz,J2=1.8Hz),3.21(2H,q,J=7.5Hz),1.26(3H,t,J=7.3Hz).
合成实例2:
(1)三甲基[2-[4-(三氟甲基)-2-吡啶基]乙炔基]硅烷的合成
在氮气氛中,依次将氯化钯(II)(3.17g、17.9mmol)、三苯基膦(9.4g、35.8mmol)和碘化铜(I)(5.5g、28.6mmol)加入到2-氯-4-(三氟甲基)吡啶(65g,358mmol)的三乙胺(320mL)溶液中,并在冰冷却下滴加三甲基甲硅烷基乙炔(42.2g,429.7mmol)。滴加完成后,溶液在80℃下搅拌8小时,经硅藻土过滤,减压浓缩。随后,加入氨水(30mL)和水,将所得溶液用乙酸乙酯萃取。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:20)纯化得到标题化合物(82.2g,收率:94.4%),为橙色油性产物。
1HNMR谱(CDCI3)σ:8.75(1H,d,J=5.0Hz),7.67(1H,s),7.44(1H,dd,J1=5.0Hz,J2=0.9Hz),0.29(9H,s).
(2)2-乙炔基-4-(三氟甲基)吡啶的合成
向三甲基[2-(4-(三氟甲基)-2-吡啶基]乙炔基]硅烷(82.2g,337.9mmol)的甲醇(200ml)和三氯甲烷(200ml)溶液中加入碳酸钾(2.3g,16.9mmol),然后在室温下搅拌1小时。减压蒸馏除去溶剂后,将水加入溶液中,用乙醚萃取所得溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,粗产物经硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:10)纯化得到标题化合物(45.8g,收率:79%),为无色油性产品。
1HNMR谱(CDCI3)σ:8.79(1H,d,J=5.0Hz),7.70(1H,s),7.49(1H,dd,J1=5.0Hz,J2=0.9Hz),3.27(1H,s).
(3)2-氯-4-(五氟-6-磺酰基)苯胺的合成
将4-氨基苯基五氟化硫(6g,27.4mmol)的乙腈溶液(24mL)加热到60℃,加入N-氯琥珀酰亚胺(4.02g,30.1mmol),然后在回流加热下搅拌3小时。将所得溶液冷却至室温,然后在减压下蒸馏除去溶剂。向所得残留物加入30mL的5%氢氧化钠水溶液,所得溶液用乙酸乙酯萃取。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:7)纯化获得标题化合物(收率6.40g,收率:92%),为红棕油物质。
1HNMR谱(CDCI3)σ:7.66(1H,d,J=2.7Hz),7.45(1H,dd,J1=8.9Hz,J2=2.5Hz),6.72(1H,d,J=9.2Hz),4.42(2H,br).
(4)(4-叠氮基-3-氯苯基)-五氟-λ6-硫烷的合成
将2-氯-4-(五氟-λ6-硫基)苯胺(6.40g,25.2mmol)的35%盐酸(30mL)和水(30mL)混合溶液冷却至5℃,滴加亚硝酸钠(2.09g,30.3mmol)水溶液(15mL)。滴加完成后,将所得溶液在-5℃下搅拌30分钟,随后滴加叠氮化钠(2.13g,32.8mmol)水溶液(15mL)。将所得溶液在-5℃下搅拌60分钟,室温下搅拌4小时。用乙酸乙酯萃取反应溶液,用饱和盐水洗涤有机层,用硫酸钠干燥,过滤除去白色沉淀物,并在减压下浓缩。所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:20)得到标题化合物(4.50g,收率:64%),为橙色油性产品。
1HNMR谱(CDCI3)σ:7.80(1H,d,J=2.3Hz),7.68(1H,dd,J1=8.9Hz,J2=2.5Hz),7.23(1H,d,J=8.7Hz).
(5)[3-氯-4-[4-[4-(三氟甲基)-2-吡啶基]三唑-1-基]苯基]-五氟-λ6-硫烷的合成
向(4-叠氮基-3-氯苯基)-五氟-6-硫烷(490.2mg,1.8mmol)的N,N'-二甲基甲酰胺(4mL)和水(1mL)混合溶液中依次添加2-乙炔基-4-(三氟甲基)吡啶(300mg,1.8mmol),无水硫酸铜(II)(42.0mg,0.3mmol)和抗坏血酸钠(138.9g,0.70mmol),然后在室温下搅拌过夜。将水加入到所得到的反应溶液中,用乙酸乙酯萃取所得溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:6)纯化得到的粗标题化合物(产生690.1mg,收率:87%),为黄色固体。
1HNMR谱(CDCI3)σ:8.81(1H,d,J=5.0Hz),8.74(1H,s),8.51(1H,s),8.06(1H,s),7.91(2H,s),7.51(1H,d,J=5.0Hz).
(6)3-乙炔基硫基-4-[4-[4-(三氟甲基)-2-吡啶基]三唑-1-基]苯基]-五氟-λ6-硫烷(2-118)的合成
将60%氢化钠(71.4mg,1.8mmol)的N,N'-二甲基甲酰胺溶液(5mL)在冰上冷却,随后滴加乙硫醇(110.8mg,滴加1.8mmol),接着搅拌10分钟。随后,在冰冷却下加入[3-氯-4-(4-[4-(三氟甲基)-2-吡啶基]-三唑-1-基]苯基]-五氟-6-硫烷(618.5mg,1.4mmolL),然后在室温下搅拌2小时。将水加入反应溶液中,用乙酸乙酯萃取所得溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:6)纯化,得到标题化合物(419.1mg,收率:64%)为红色固体。
1HNMR谱(CDCI3)σ:8.81(1H,d,J=5.0Hz),8.63(1H,s),8.51(1H,s),7.87(1H,d,J=2.3Hz),7.76(1H,dd,J1=8.7Hz,J2=2.3Hz),7.67(1H,d,J=8.7Hz),7.49(1H,d,J=4.1Hz),2.93(2H,q,J=7.3Hz),1.29(3H,t,J=7.3Hz).
(7)[3-乙基磺酰基-4-[4-[4-(三氟甲基)-2-吡啶基]三唑-1-基]苯基]五氟-λ6-硫烷(2-398)的合成
向[3-乙基硫基-4-[(4-[4-(三氟甲基)-2-吡啶基]三唑-1-基]苯基]]-五氟-λ6-亚砜(974mg,2mmol)的氯仿(3mL)溶液,在冰冷却下加入77%的间氯已苯甲酸(939.3mg,4.2mmol),然后在冰冷却下搅拌过夜。在反应溶液中加入饱和碳酸氢钠水溶液,用氯仿萃取溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:1)纯化得到标题化合物(产生490mg,收率:47%)为白色固体。
1HNMR谱(CDCI3)σ:8.81(1H,d,J=5.0Hz),8.66(1H,d,J=2.7Hz),8.60(1H,s),8.48(1H,s),8.24(1H,dd,J1=8.7Hz,J2=2.7Hz),7.72(1H,d,J=8.7Hz),7.51(1H,d,J=6.0Hz),3.39(2H,q,J=7.5Hz),1.33(3H,t,J=7.3Hz).
合成实例3:
(1)2-(1H-三唑-4-基)-4-(三氟甲基)吡啶的合成
在氮气氛中,依次将碘化铜(I)(223mg,1.2mmol)和叠氮三甲基硅烷(4g,35.1mmol)添加到N,N'-二甲基甲酰胺(9mL)和2-乙炔基-4-(三氟甲基)吡啶(4g,23.4mmol)的甲醇(1mL)混合溶液中,然后在100℃搅拌7小时。将所得溶液冷却至室温并通过硅藻土过滤,并在减压下浓缩滤液。随后,所得粗产物用硅胶柱色谱(洗脱溶剂:乙酸乙酯/己烷=2∶1)纯化,得到标题化合物(产生2.0g,收率:40%)为棕色固体。
1HNMR谱(CDCI3)σ:8.83(1H,d,J=5.0Hz),8.36(1H,s),8.27(1H,br),7.50(1H,d,J=4.6Hz).
(2)3-乙炔基磺酰基-5-(三氟甲基)-2[4-[4-(三氟甲基)-2-吡啶基]三唑-1-基]吡啶(2-387)的合成
将2-(1H-三唑-4-基)-4-(三氟甲基)吡啶(200mg,0.9mmol),碳酸钾(193.6mg,1.4mmol)和2,3-二(乙基磺酰基)-5(三氟甲基)吡啶(464.1mg,1.4mmol),(参照国际出版物2016/20286的合成方法)依次加入N,N'-二甲基甲酰胺(3mL)溶液,然后在室温下搅拌过夜。将水加入到溶液中,所得溶液用乙酸乙酯萃取。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,粗产物经硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:6)提纯,得到标题化合物(105mg,收率:25%)为白色固体。
1HNMR谱(CDCI3)σ:9.14(1H,m),8.90-8.87(2H,m),8.62(1H,s),8.32(1H,s),7.57(1H,dd,J1=5.0Hz,J2=0.9Hz),3.99(2H,q,J=7.5Hz),1.50(3H,t,J=7.6Hz).
合成实例4:
1-(2-乙基硫基苯基)-4-[3-(三氟甲基)苯基]三唑(1-26)的合成
在3'-(三氟甲基)苯乙酮(400mg,2.1mmol)的二甲基亚砜(4mL)溶液中,依次添加2-乙基硫苯胺(390.9mg,2.6mmol),4-甲基苯磺酰肼(593.9mg,3.2mmol),碘(809.4mg,3.2mmol),然后在100℃搅拌6小时。将水倒入反应溶液中,用乙酸乙酯萃取所得溶液。有机层用10%硫代硫酸钠水溶液洗涤,然后用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,并在减压下浓缩,所得粗产物用硅胶柱色谱法(洗脱溶剂:乙酸乙酯/己烷=1:6)纯化得到的粗产品得到包体化合物(得到3153mg,产率:42%),为褐色油产物。
1HNMR谱(CDCI3)σ:8.24(1H,s),8.18(1H,s),8.14(1H,d,J=7.3Hz),7.64-7.59(2H,m),7.55-7.47(3H,m),7.39(1H,td,J1=7.4Hz,J2=1.5Hz),2.83(2H,q,J=7.3Hz),1.24(3H,t,J=7.3Hz).
合成实例5:
1-(2-乙基硫基苯基)-5-甲基-4-[3-(三氟甲基)苯基]三唑(1-27)的合成
在4-甲苯磺酰胺(460.6mg,2.5mmol)的甲醇(3mL)溶液中,依次加入3'-(三氟甲基)苯丙酮(500mg,2.5mmol),然后在室温下搅拌10分钟。减压蒸馏除去溶剂,向得到的白色固体中依次加入甲苯(5mL)、乙酸铜(II)(449.2mg、2.5mmol)、特戊酸(505.2mg、4.9mmol)和2-乙基硫基苯胺(758mg,4.9mmol),然后在110℃搅拌8小时。溶剂经减压浓缩,所得粗产物经硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1∶6)纯化,得到标题化合物(得到383.5mg,收率43%),为红棕油物质。
1HNMR谱(CDCI3)σ:8.11(1H,s),8.05(1H,dt,J1=4.5Hz,J2=2.4Hz),7.65-7.61(2H,m),7.54-7.51(2H,m),7.41-7.35(1H,m),2.85(2H,q,J=7.3Hz),1.25(3H,t,J=7.6Hz).
合成实例6:
5-[3,5-二(三氟甲基)苯基]-3-(2-乙基硫基苯基)三唑-4-胺(1-82)的合成
在3,5-二(三氟甲基)苯乙腈(3.59g,14.2mmol)的乙醇(10mL)溶液和2-乙基硫基苯胺(2.54g,14.2mmol)在冰上冷却,依次加入乙醇(10mL)甲醇钠(1.2g,21.3mmol),然后在冰冷却下搅拌72小时。将水倒入反应溶液中,用乙酸乙酯萃取所得溶液。有机层用饱和盐水洗涤,用硫酸钠干燥,过滤除去白色沉淀物,减压浓缩,所得粗产物用硅胶柱层析(洗脱溶剂:乙酸乙酯/己烷=1:6)纯化得到标题化合物(产出5.3g,收率:87%),为红棕油物质。
1HNMR谱(CDCI3)σ:8.29(2H,s),7.79(1H,s),7.58-7.52(2H,m),7.44-7.39(2H,m),4.00(2H,br),2.87(2H,q,J=7.3Hz),1.27(3H,t,J=7.3Hz).
在上述合成和生产实例中产出的化合物的核磁共振谱和(ppm)值在表5中进行展示。核磁共振谱数据由JNM-ECS400光谱仪(JEOL有限公司制造)测量。
[表5-1]
[表5-2]
[表5-3]
[表5-4]
[表5-5]
[表5-6]
[表5-7]
[表5-8]
[表5-9]
[表5-10]
[表5-11]
[表5-12]
[表5-13]
[表5-14]
[表5-15]
[表5-16]
[表5-17]
[表5-18]
[表5-19]
[表5-20]
[表5-21]
[表5-22]
[表5-23]
[表5-24]
<制剂>
将本发明化合物配置为农业/园艺杀虫剂或杀螨剂的方法的具体实施例在下列制剂实例1至5中进行具体描述。
制剂实例1:粉尘剂
通过均匀地粉碎和混合合成实例1的化合物(1-631)(2重量份)、PAP(异丙基磷酸酯)(1重量份)和粘土(97重量份),可以得到含有2wt%活性剂的粉尘。此外,除使用表1至表4所示的相应化合物代替合成实例1的化合物外,可通过相同的方法获得各个粉尘剂。
制剂实例2:可湿性粉剂
通过均匀地粉碎和混合合成实例的化合物(1-631)(20重量份)、烷基苯磺酸钠(3重量份)、聚氧乙烯烷基苯基醚(5重量份)和白土(72重量份),可获得含20wt%活性剂的可湿性粉剂。此外,除了使用表1至表4所示的相应化合物代替合成实例1的化合物外,可以通过相同的方法获得各个可湿性粉剂。
制剂实例3:可乳化浓缩剂
通过混合和溶解合成实例1的化合物(1-631)(30重量份)、甲基萘(40重量份)和聚氧乙烯烷基苯基醚(30重量份),可以得到含有30wt%活性剂的可乳化浓缩剂。此外,除了使用表1至表4所示的相应化合物代替合成实例1的化合物外,可以使用相同的方法获得各个可乳化浓缩剂。
制备实例4:流动剂(flowable formulation)
通过将合成实例1的化合物(1-631)(25重量份)、聚氧乙烯烷基醚(1重量份)、烷基萘磺酸钠(1重量份)、黄烷胶(1重量份)和水(72重量份)均匀混合,可得到含有25wt%活性剂的流动剂。此外,除了使用表1至表4所示的相应化合物代替合成实例1的化合物之外,可以使用相同的方法获得各个流动剂。
制备实例5:颗粒
可以通过进一步将水(15重量份)加入合成实例1的化合物(1-631)(5重量份)、十二烷基硫酸钠(1重量份)、木质素磺酸钙(5重量份)、膨润土(30重量份)和粘土(59重量份)混合得到含有5wt%活性剂的颗粒。然后在捏合机中捏合,在造粒机中造粒,并在流体干燥器中干燥。此外,除了使用表1至4所示的相应化合物代替合成实例1的化合物(1-631)外,可以通过相同的方法获得各个颗粒。
下面,在测试实例1至5中描述对上述得到的根据本发明的害虫防治剂的防治效果进行评估的具体实施例。
测试实例1:斜纹夜蛾(Spodoptera litura)防治测试
将在细胞托盘中生长的甘蓝幼苗放置在转盘上,并通过喷枪将30mL根据制剂实例3制备的稀释的可乳化浓缩剂(500ppm)均匀地喷在其上。在空气干燥后,将幼苗放入具有盖的塑料容器中,该盖穿孔以气孔,在每个容器中释放第二龄幼虫的五只斜纹夜蛾,容器在25℃下放置于恒温室(照明16小时)。释放后四天,对存活幼虫的数量进行调查,根据下列计算公式(a)计算死亡率(%),测试实施两次。
公式(a):
死亡率(%)={1-(在处理区中调查日存活幼虫数/未处理区中调查日存活幼虫数)}*100.
作为代表性实例,化合物1-75、1-81、1-82、1-83、1-85、1-86、1-87、1-88、1-91、1-197、1-229、1-236、1-243、1-251、1-255、1-278、1-305、1-310、1-319、1-336、1-354、1-360、1-361、1-363、1-364、1-365、1-366、1-367、1-369、1-370、1-475、1-507、1-513、1-520、1-528、1-536、1-552、1-554、1-555、1-562、1-587、1-596、1-631、1-637、1-638、1-639、1-640、1-641、1-642、1-643、1-644、1-646、1-647、1-752、1-784、1-786、1-790、1-791、1-798、1-802、1-805、1-806、1-809、1-810、1-815、1-820、1-823、1-830、1-831、1-832、1-833、1-860、1-862、1-867、1-869、2-30、2-32、2-33、2-91、2-96、2-97、2-99、2-100、2-102、2-107、2-112、2-113、2-127、2-134、2-135、2-140、2-143、2-145、2-147、2-169、2-171、2-172、2-230、2-234、2-235、2-236、2-238、2-239、2-241、2-246、2-252、2-261、2-262、2-267、2-275、2-283、2-285、2-295、2-297、2-299、2-309、2-311、2-312、2-322、2-323、2-325、2-329、2-330、2-332、2-351、2-353、2-367、2-370、2-374、2-375、2-376、2-377、2-378、2-379、2-381、2-386、2-388、2-389、2-392、2-393、2-397、2-398、2-401、2-402、2-407、2-408、2-409、2-410、2-411、2-414、2-415、2-420、2-423、2-425、2-427、3-14、3-15、3-29、3-30、3-45、4-10、4-25显示死亡率达80%或更多。
测试实例2:褐飞虱(Nilaparvata lugens)防治测试
将在塑料杯中生长的发芽稻秧苗放置在转盘上,通过喷枪均匀地喷洒30mL根据制剂实例3制备的稀释的可乳化浓缩剂(500ppm)。空气干燥后,将其放入聚碳酸酯制成的塑料容器中,该容器具有设置有尼龙纱布的盖,在每个容器中释放十个褐飞虱第四龄褐飞虱幼虫,容器置于25℃的恒温室中(照明16小时)。释放后五天,对存活幼虫的数量进行调查,根据下列计算公式(a)计算死亡率(%),测试实施两次。
公式(a):
死亡率(%)={1-(在处理区中调查日存活幼虫数/未处理区中调查日存活幼虫数)}*100.
作为代表性实例,化合物1-56、1-83、1-488、1-578、2-147、2-409、2-414、2-427、3-14和4-25显示死亡率为80%或更多。
测试实验3:苜蓿蚜(Aphis craccivora)防治实验
在塑料杯中生长的蚕豆(Vicia faba)幼苗上释放三个苜蓿蚜成虫。释放后一天,将蚕豆幼苗放置在转盘上,通过喷枪均匀地喷洒30mL根据制剂实例3制备的稀释的可乳化浓缩剂(500ppm)。处理后,将幼苗置于25℃恒温室中(照明16小时)。处理后四天,调查寄生成虫和幼虫的数量,并根据下列计算公式(b)计算预防值(%)。测试实施两次。
公式(b):
预防值(%)={1-(处理区中调查日寄生昆虫数/未处理区中调查日寄生昆虫数)}*100.
作为代表性实例,化合物1-26、1-232、1-275、1-510、2-91、2-100、2-140、2-230、2-370、2-375、2-379、2-407、2-408、2-420、2-423、3-15和3-45显示出预防值为80%或更多。
测试实例4:二斑叶螨(Tetranychus urticae)防治测试
将十个二斑叶螨雌性成虫释放在塑料杯中生长的每个豆幼苗上。释放后一天,将豆幼苗放置在转盘上,通过喷枪均匀地喷洒30mL根据制剂实例3制备的稀释的可乳化浓缩剂(500ppm)。处理后,将幼苗置于25℃恒温室中(照明16小时)。处理后八天,对寄生昆虫的存活数进行调查,并根据下列计算公式(b)计算预防值(%),测试实施两次。
公式(b):
预防值(%)={1-(处理区中调查日寄生虫数/未处理区中调查日寄生虫数)}*100.
作为代表性实例,化合物1-834显示出80%或更多的预防值。
工业应用:
根据本发明,可以提供具有优良杀虫杀螨效果的新型1,2,3-三唑衍生物和含有1,2,3-三唑衍生物的杀虫剂或杀螨剂。
通过详细描述了本发明和具体实施例,本领域技术人员可在其中进行各种变化和修改,而不脱离本发明的精神和范围。
本申请基于2015年11月30日提交的日本专利申请(专利申请号2015-33791),其内容以引用方式并入本申请。
Claims (3)
1.一种1,2,3-三唑衍生物由式(1)表示,
[式1]
其中在式(1)中:
R为乙基;
n代表0到2的整数;
W1和W2代表CH;
X为氢原子、卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、五氟硫烷基、或可被卤素原子取代的芳基,其中所述芳基选自苯基、2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-碘苯基、3-碘苯基、4-碘苯基、2,4-二氯苯基、2,6-二氯苯基、3,4-二氯苯基、3,5-二氯苯基;
m代表1到4的整数,当m表示2或更大的整数时,各自的X可以相同也可不同;
Q为苯基,可被一个或多个选自以下的基团取代:卤素原子、氰基、硝基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、五氟硫烷基、氮原子可被C1-C6烷基取代的(C1-C6烷基)氨基磺酰基、可被卤素原子或C1-C6烷基取代的苯基、可被卤素原子或C1-C6烷基取代的苯氧基和可被卤素原子取代的苯甲酰基;
Z为氢原子。
2.一种1,2,3-三唑衍生物由式(1)表示,
[式1]
其中在式(1)中:
R为乙基;
n代表0到2的整数;
W1和W2为CH;
X为氢原子、卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷基羰基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基、(C1-C6烷氧基)羰基、二(C1-C6烷基)氨基、(C1-C6烷基)羰基氨基、(C1-C6烷基)羰基(C1-C6烷基)氨基、五氟硫烷基或可被卤素原子取代的芳基,其中所述芳基选自苯基,2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、2-溴苯基、3-溴苯基、4-溴苯基、2-碘苯基、3-碘苯基、4-碘苯基、2,4-二氯苯基、2,6-二氯苯基、3,4-二氯苯基、3,5-二氯苯基;
m代表1到4的整数,当m表示2或更大的整数时,各自的X可以相同也可不同;
Q为吡啶基,其可以由一个或多个选自以下的基团取代:卤素原子、氰基、可被氰基取代的C1-C6烷基、可被氰基取代的C3-C6环烷基、C1-C6烷氧基、可被氰基取代的C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基、C1-C6卤代烷基羰基和五氟硫烷基;
Z为氢原子。
3.一种含有权利要求1或2中任一项的1,2,3-三唑衍生物作为活性成分的杀虫剂或杀螨剂。
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US11046659B2 (en) | 2021-06-29 |
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