TWI829595B - 作為殺蟲劑之新穎雜芳基三唑和雜芳基四唑化合物 - Google Patents
作為殺蟲劑之新穎雜芳基三唑和雜芳基四唑化合物 Download PDFInfo
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- TWI829595B TWI829595B TW112119453A TW112119453A TWI829595B TW I829595 B TWI829595 B TW I829595B TW 112119453 A TW112119453 A TW 112119453A TW 112119453 A TW112119453 A TW 112119453A TW I829595 B TWI829595 B TW I829595B
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- phenyl
- cycloalkyl
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- 239000000575 pesticide Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 176
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- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 58
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 54
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- 229910052731 fluorine Inorganic materials 0.000 claims description 54
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 41
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- NAHGTSVYKAHQNA-UHFFFAOYSA-N 3-cyclopropyl-5-(trifluoromethoxy)benzoic acid Chemical compound C1(CC1)C=1C=C(C(=O)O)C=C(C=1)OC(F)(F)F NAHGTSVYKAHQNA-UHFFFAOYSA-N 0.000 claims description 2
- IMAOINSQXWKXPK-UHFFFAOYSA-N methyl 3-cyclopropyl-5-(trifluoromethoxy)benzoate Chemical compound C1(CC1)C=1C=C(C(=O)OC)C=C(C=1)OC(F)(F)F IMAOINSQXWKXPK-UHFFFAOYSA-N 0.000 claims description 2
- GICYPCVPKJIIRE-UHFFFAOYSA-N 3-ethylsulfanyl-5-fluorobenzoic acid Chemical compound CCSC1=CC(F)=CC(C(O)=O)=C1 GICYPCVPKJIIRE-UHFFFAOYSA-N 0.000 claims 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical group CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 claims 1
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- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000014616 translation Effects 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 229940072651 tylenol Drugs 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
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Chemical class 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P5/00—Nematocides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/14—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 three or more hetero rings
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Abstract
本發明關於新穎通式(I)之雜芳基三唑和雜芳基四唑化合物,其中結構單元Y、Q
1、Q
2、R
1、R
2、R
3a、R
3b、R
4和R
5具有說明中所給的意義,包含該等化合物之調配物和組成物、及彼等在植物保護中用於控制動物害蟲(包括節肢動物和昆蟲)之用途及彼等用於控制動物體外寄生蟲之用途。
Description
本發明關於新穎雜芳基三唑和雜芳基四唑化合物,包含該等化合物之調配物和組成物及彼等在植物保護中用於控制動物害蟲(包括節肢動物和昆蟲)之用途及彼等用於控制動物體外寄生蟲之用途。
在WO 2017/192385中揭示某些式I之雜芳基三唑和雜芳基四唑化合物(R
3b=氫)用於控制動物外寄生蟲之用途。
現代植物保護產品和獸醫殺體外寄生蟲劑必須符合許多要求,例如關於效力、持久性、廣效性、和抗破壞性質。毒性的問題、與其他活性化合物或調配物助劑之可組合性發揮作用以及合成活性化合物所需費用的問題。此外,可能發生抗藥性。基於所有該等理由,對新穎作物保護組成物或獸醫外寄生蟲殺蟲劑的研究不能視為完備,且與已知化合物相比至少在相關的各個方面具有改良性質之新穎化合物仍有持續的需求。
本發明之目的為提供在各方面擴大殺蟲劑藥譜之化合物。
本發明因此提供一種通式(I)之化合物
(I),
其中(構型1-1):
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
6烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;氧呾-3-基-CH
2-或視需要地經鹵素或C
1-C
3鹵烷基取代的苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、或在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-NHCO-苯基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多三個取代基係獨立地選自由下列所組成之群組A:C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基(C
3-C
6cycloalkylsulfanyl)、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、在各情況下視需要地經取代的C
3-C
6環烷基、苯硫基(phenylsulfanyl)、苯亞磺醯基、苯磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基 -NHCO-苯基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基和C
1-C
4鹵烷氧基;
其他一至二個視需要的取代基係各自獨立地選自由下列所組成之群組B:鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-NHCO-苯基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的萘基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-NHCO-苯基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為選自由下列所組成群組之雜環:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基、9-員雜芳基和10-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-NHCO-苯基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基或C
1-C
6鹵烷基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;鹵素;-CN;視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
1-C
4烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;視需要地經取代的C
3-C
6環烷基;視需要地經取代的C
1-C
6鹵烷基;視需要地經取代的C
2-C
6烯基;視需要地經取代的C
2-C
6鹵烯基;視需要地經取代的C
2-C
6炔基;苯甲基,其中該苯基取代基係視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
4烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、和C
1-C
3烷磺醯基;雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、和C
1-C
4烷氧基;視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代的苯基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
4烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、和C
1-C
3烷磺醯基;或雜環基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、和C
1-C
4烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成C
3-C
6-碳環或3-至6-員雜環系統,視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
4烷氧基和C
1-C
3鹵烷氧基;
R
4為吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基,其中該吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-CSNH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-NHCO-C
3-C
6環烷基、-NHCO-苯基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
3-C
6環烷基、-N(C
1-C
4烷基)CO-苯基、-N(SO
2C
1-C
3烷基)
2、-NH(SO
2C
1-C
3烷基)、-N(C
1-C
4烷基)(SO
2C
1-C
3烷基)、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H和-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
R
5為氫、鹵素、-CN、或在各情況下視需要地經取代的C
1-C
3烷基、C
3-C
4環烷基、C
1-C
3烷氧基、C
1-C
3烷氧基C(O)-、(C
1-C
3烷氧基)
2CH-、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-C(=NOC
1-C
4烷基)H、或-C(=NOC
1-C
4烷基)-C
1-C
4烷基。
本發明此外提供通式(I)之化合物
其中(構型1-2)
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或視需要地經取代的CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
6烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;視需要地經鹵素或C
1-C
3鹵烷基取代的氧呾-3-基-CH
2-或苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:
鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2,
及在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
6鹵烷硫基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-NHCO-苯基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
6烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
6烷基)H、-C(=NOC
1-C
6烷基)-C
1-C
6烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6鹵烷基和C
1-C
6烷氧基;
及視需要地經取代的4-至6-員飽和或部分不飽和雜環;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多三個取代基係獨立地選自由下列所組成之群組A:
視需要地經取代的C
4-C
6烷基;
C
1-C
6烷硫基,其視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:-NH
2、-OH、-NO
2、-CN、-SH、CO
2C
1-C
4烷基、-CONH
2、SF
5、-SO
2NH
2、C
1-C
4烷基、C
3-C
4環烷基、C
2-C
4烯基、C
5-C
6環烯基、C
2-C
4炔基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、N-C
1-C
4烷醯胺基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
2-C
4烯氧基、C
2-C
4炔氧基、C
3-C
4環烷氧基、C
5-C
6環烯氧基、C
1-C
4烷氧羰基、C
2-C
4烯氧羰基、C
2-C
4炔氧羰基、C
6-、C
10-、C
14-芳氧羰基、C
1-C
4烷醯基、C
2-C
4烯羰基、C
2-C
4炔羰基、C
6-、C
10-、C
14-芳羰基、C
1-C
4烷硫基、C
1-C
4鹵烷硫基、C
3-C
4環烷硫基、C
2-C
4烯硫基、C
5-C
6環烯硫基、C
2-C
4炔硫基、C
1-C
4烷亞磺醯基、C
1-C
4鹵烷亞磺醯基、C
1-C
4烷磺醯基、C
1-C
4鹵烷磺醯基、-SO
2-NH(C
1-C
6烷基)、-SO
2-N(C
1-C
6烷基)
2、C
1-C
4烷氧膦基(phosphinyl)、C
1-C
4烷膦醯基(phosphonyl)、N-C
1-C
4烷胺羰基、N,N-二-C
1-C
4烷胺羰基、N-C
1-C
4烷醯胺羰基、N-C
1-C
4烷醯基-N-C
1-C
4烷胺羰基、C
6-、C
10-、C
14-芳基、C
6-、C
10-、C
14-芳氧基、苯甲基、苯甲氧基、苯甲硫基、C
6-、C
10-、C
14-芳硫基、C
6-、C
10-、C
14-芳胺基、苯甲胺基、雜環基、雜芳基和三烷矽基,經由雙鍵鍵結之取代基,諸如C
1-C
4亞烷基(例如亞甲基或亞乙基)、側氧基、亞胺基和經取代的亞胺基;
及在各情況下視需要地經取代的C
4-C
6鹵烷硫基、C
4-C
6鹵烷氧基、C
4-C
6烷氧基、C
4-C
6鹵烷基、C
3-C
6環烷基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、C
2-C
6烯硫基(C
2-C
6alkenylsulfanyl)、C
2-C
6烯亞磺醯基、C
2-C
6烯磺醯基、C
2-C
6炔硫基(C
2-C
6alkinylsulfanyl)、C
2-C
6炔亞磺醯基、C
2-C
6炔磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、雜環基硫基、雜環亞磺醯基、雜環磺醯基、雜芳硫基(heteroarylsulfanyl)、雜芳亞磺醯基、雜芳磺醯基、S-C
1-C
6烷亞磺醯亞胺醯基(S-C
1-C
6alkylsulfinimidoyl)、S-C
3-C
6環烷亞磺醯亞胺醯基、S-C
2-C
6烯亞磺醯亞胺醯基、S-C
2-C
6炔亞磺醯亞胺醯基、S-苯亞磺醯亞胺醯基、S-雜環亞磺醯亞胺醯基、S-雜芳亞磺醯亞胺醯基、S-C
1-C
6烷磺醯亞胺醯基(S-C
1-C
6alkylsulfonimidoyl)、S-C
3-C
6環烷磺醯亞胺醯基、S-C
2-C
6烯磺醯亞胺醯基、S-C
2-C
6炔磺醯亞胺醯基、S-苯磺醯亞胺醯基、S-雜環磺醯亞胺醯基、S-雜芳磺醯亞胺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-N(C
3-C
6環烷基)CO-C
1-C
6烷基、-NHCO-苯基、-N(C
1-C
6烷基)CO-苯基、-N(C
3-C
6環烷基)CO-苯基、-NHCO-C
3-C
6環烷基、-N(C
1-C
6烷基)CO-(C
3-C
6環烷基)、-N(C
3-C
6環烷基)CO-(C
3-C
6環烷基)、-NHCO-雜芳基、-N(C
1-C
6烷基)CO-雜芳基、-N(C
3-C
6環烷基)CO-雜芳基、-NHCO-雜環基、-N(C
1-C
6烷基)CO-雜環基、-N(C
3-C
6環烷基)CO-雜環基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
6烷基)(C
3-C
6環烷基)、-CON(C
3-C
6環烷基)
2、-CONH-苯基、-CON(C
1-C
6烷基)苯基、-CON(C
3-C
6環烷基)苯基、-CONH-雜芳基、-CON(C
1-C
6烷基)雜芳基、-CON(C
3-C
6環烷基)雜芳基、-CONH-雜環基、-CON(C
1-C
6烷基)雜環基、-CON(C
3-C
6環烷基)雜環基、-C(=NOC
1-C
6烷基)H、-C(=NOC
1-C
6烷基)-C
1-C
6烷基、-NHSO
2-C
1-C
6烷基、-N(C
1-C
6烷基)SO
2-C
1-C
6烷基、-N(C
3-C
6環烷基)SO
2-C
1-C
6烷基、-NHSO
2-苯基、-N(C
1-C
6烷基)SO
2-苯基、-N(C
3-C
6環烷基)SO
2-苯基、-NHSO
2-C
3-C
6環烷基、-N(C
1-C
6烷基)SO
2-(C
3-C
6環烷基)、-N(C
3-C
6環烷基)SO
2-(C
3-C
6環烷基)、-NHSO
2-雜環基、-N(C
1-C
4烷基)SO
2-雜環基、-N(C
3-C
6環烷基)SO
2-雜環基、-NHSO
2-雜芳基、-N(C
1-C
6烷基)SO
2-雜芳基、-N(C
3-C
6環烷基)SO
2-雜芳基、-SO
2NH(C
1-C
6烷基)、-SO
2N(C
1-C
6烷基)
2、-SO
2N(C
1-C
6烷基)(C
3-C
6環烷基)、-SO
2NH(C
3-C
6環烷基)、-SO
2N(C
3-C
6環烷基)
2、-SO
2NH(苯基)、-SO
2N(C
1-C
6烷基)(苯基)、-SO
2N(C
1-C
4環烷基)(苯基)、-SO
2NH(雜芳基)、-SO
2N(C
1-C
6烷基)(雜芳基)、-SO
2N(C
3-C
6環烷基)(雜芳基)、-SO
2NH(雜環基)、-SO
2N(C
1-C
4烷基)(雜環基)、-SO
2N(C
3-C
6環烷基)(雜環基);
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基和C
1-C
6鹵烷氧基;
及視需要地經取代的4-至6-員飽和或部分不飽和雜環;
及-SO
2NH
2;
及另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:
鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2,
及在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
6鹵烷硫基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-NHCO-苯基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
6烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
6烷基)H、-C(=NOC
1-C
6烷基)-C
1-C
6烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6鹵烷基和C
1-C
6烷氧基;
或
R
2為視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的萘基:
鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2,
及在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
6鹵烷硫基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-NHCO-苯基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-C(=NOC
1-C
6烷基)H、-C(=NOC
1-C
6烷基)-C
1-C
6烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6鹵烷基和C
1-C
6烷氧基;
或
R
2為選自由下列所組成群組之雜環:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基、9-員雜芳基和10-員雜芳基,彼等各自係視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:
鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2,
及在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
3-C
6環烷基-C
1-C
6烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
6鹵烷硫基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-NHCO-苯基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-C(=NOC
1-C
6烷基)H、-C(=NOC
1-C
6烷基)-C
1-C
6烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6鹵烷基和C
1-C
6烷氧基;
或
R
2為在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基或C
1-C
6鹵烷基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;鹵素;-CN;視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、和-CON(C
1-C
6烷基)
2;視需要地經取代的C
3-C
6環烷基;視需要地經取代的C
1-C
6鹵烷基;視需要地經取代的C
2-C
6烯基;視需要地經取代的C
2-C
6鹵烯基;視需要地經取代的C
2-C
6炔基;苯甲基,其中該苯基取代基係視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、和C
1-C
6烷磺醯基;雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、和C
1-C
6烷氧基;視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代的苯基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、和C
1-C
6烷磺醯基;或雜環基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、和C
1-C
6烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成C
3-C
6-碳環或3-至6-員雜環系統,視需要地經一至二個、各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、在各情況下視需要地經取代的C
1-C
6烷基、C
1-C
6烷氧基和C
1-C
6鹵烷氧基;
R
4為吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基,其中該吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CO
2-C
1-C
6烷基、-SO
2NH
2、-CONH
2、-CSNH
2、-NO
2、-NH
2、在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
1-C
6鹵烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
6鹵烷硫基、C
1-C
6鹵烷亞磺醯基、C
1-C
6鹵烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
2-C
4烯硫基、C
2-C
4烯亞磺醯基、C
2-C
4烯磺醯基、C
2-C
4炔硫基、C
2-C
4炔亞磺醯基、C
2-C
4炔磺醯基、苯硫基、苯亞磺醯基、苯磺醯基、S-C
1-C
6烷亞磺醯亞胺醯基、S-C
3-C
6環烷亞磺醯亞胺醯基、S-C
2-C
6烯亞磺醯亞胺醯基、S-C
2-C
6炔亞磺醯亞胺醯基、S-苯亞磺醯亞胺醯基、S-C
1-C
6烷磺醯亞胺醯基、S-C
3-C
6環烷磺醯亞胺醯基、S-C
2-C
6烯磺醯亞胺醯基、S-C
2-C
6炔磺醯亞胺醯基、S-苯磺醯亞胺醯基、-NH(C
1-C
6烷基)、-N(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-N(C
3-C
6環烷基)CO-C
1-C
6烷基、-NHCO-C
3-C
6環烷基、-N(C
1-C
6烷基)CO-(C
3-C
6環烷基)、-N(C
3-C
6環烷基)CO-(C
3-C
6環烷基)、-N(C
1-C
6烷基)CO-苯基、-N(C
3-C
6環烷基)CO-苯基、-NHCO-苯基、-N(CO-C
1-C
6烷基)
2、-N(CO-C
3-C
6環烷基)
2、-N(CO-苯基)
2、-N(CO-C
3-C
6環烷基)(CO-C
1-C
6烷基)、-N(CO-C
3-C
6環烷基)(CO-苯基)、-N(CO-C
1-C
6烷基)(CO-苯基)、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
6烷基)(C
3-C
6環烷基)、-CON(C
3-C
6環烷基)
2、-CONH-SO
2-C
1-C
6烷基、-CONH-SO
2-苯基、-CONH-SO
2-(C
3-C
6環烷基)、-CON(C
1-C
6烷基)-SO
2-C
1-C
6烷基、-CON(C
1-C
6烷基)-SO
2-苯基、-CON(C
1-C
6烷基)-SO
2-(C
3-C
6環烷基)、-CONH-苯基、-CON(C
1-C
6烷基)苯基、-CON(C
3-C
6環烷基)苯基、-N(SO
2C
1-C
6烷基)
2、-N(SO
2C
1-C
6鹵烷基)
2、-N(SO
2C
3-C
6環烷基)
2、-N(SO
2C
1-C
6烷基)SO
2-苯基、-N(SO
2C
3-C
6環烷基)SO
2-苯基、-NHSO
2-C
1-C
6烷基、-NHSO
2-C
1-C
6鹵烷基、-N(C
1-C
6烷基)SO
2-C
1-C
6烷基、-N(C
3-C
6環烷基)SO
2-C
1-C
6烷基、-NHSO
2-苯基、-N(C
1-C
6烷基)SO
2-苯基、-N(C
3-C
6環烷基)SO
2-苯基、-NHSO
2-C
3-C
6環烷基、-N(C
1-C
6烷基)SO
2-(C
3-C
6環烷基)、-N(C
3-C
6環烷基)SO
2-(C
3-C
6環烷基)、-SO
2NH(C
1-C
6烷基)、-SO
2N(C
1-C
6烷基)
2、-SO
2N(C
1-C
6烷基)(C
3-C
6環烷基)、-SO
2NH(C
3-C
6環烷基)、-SO
2N(C
3-C
6環烷基)
2、-SO
2NH(苯基)、-SO
2N(C
1-C
6烷基)(苯基)、-SO
2N(C
1-C
4環烷基)(苯基)、-C(=NOC
1-C
6烷基)H和-C(=NOC
1-C
6烷基)-C
1-C
6烷基;
R
5為氫、鹵素、-CN、或在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6烷氧基C(O)-、(C
1-C
6烷氧基)
2CH-、-CO
2C
1-C
6烷基、-CONH(C
1-C
6烷基)、-CON(C
1-C
6烷基)
2、-NHCO-C
1-C
6烷基、-N(C
1-C
6烷基)CO-C
1-C
6烷基、-C(=NOC
1-C
6烷基)H、或-C(=NOC
1-C
6烷基)-C
1-C
6烷基。
式(I)化合物同樣地涵蓋任何存在的非鏡像異構物或鏡像異構物和E/Z異構物,以及式(I)化合物的鹽和N-氧化物,及其用於控制動物害蟲之用途。
關於上下文中所指定的式之較佳基團定義係給出於下文中。
較佳者(構型2-1)為式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
6烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;氧呾-3-基-CH
2-;或視需要地經鹵素或C
1-C
3鹵烷基取代的苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成之群組取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、C
1-C
6烷基、視需要地經取代的C
3-C
6環烷基;C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多三個取代基係獨立地選自由下列所組成之群組A: C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基和C
1-C
3鹵烷基;視需要地經取代的C
3-C
6環烷基;-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基和C
1-C
4鹵烷氧基;
另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、C
1-C
6烷基、視需要地經取代的C
3-C
6環烷基;C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的萘基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、C
1-C
6烷基、視需要地經取代的C
3-C
6環烷基;C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為選自由下列所組成群組之雜環:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基、9-員雜芳基和10-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、C
1-C
6烷基、視需要地經取代的C
3-C
6環烷基;C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
6烷基:C
1-C
3烷氧基-、C
1-C
3鹵烷氧基-、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;視需要地一至二個選自由下列所組成群組之取代基經取代的C
3-C
6環烷基:鹵素、-CN、-COOH、-CONH
2、C
1-C
6烷基、C
1-C
6鹵烷基、C
3-C
6環烷基、C
1-C
6烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;C
1-C
6鹵烷基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;鹵素:-CN;視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;視需要地經一至二個選自由下列所組成群組之取代基取代的C
3-C
6環烷基:鹵素、-CN、-COOH、-CONH
2、C
1-C
6烷基、C
1-C
6鹵烷基、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;視需要地經一至二個選自由下列所組成群組之取代基取代的C
1-C
6鹵烷基:羥基、-CN、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;苯甲基,其中該苯基取代基係視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代的苯基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;及雜環基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成C
3-C
6-碳環或3-至6-員雜環系統,其視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基和C
1-C
3鹵烷氧基;
R
4為吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基,其中該吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-CSNH
2、-NO
2、-NH
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-NHCO-C
3-C
6環烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-N(C
1-C
4烷基)CO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
3-C
6環烷基;-N(C
1-C
4烷基)CO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基和C
1-C
3鹵烷基;-N(SO
2C
1-C
3烷基)
2、-NH(SO
2C
1-C
3烷基)、-N(C
1-C
4烷基)(SO
2C
1-C
3烷基)、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H,及-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
R
5為氫、鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
3-C
4環烷基、C
1-C
3烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷氧基C(O)-、(C
1-C
3烷氧基)
2CH-、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-C(=NOC
1-C
4烷基)H、或-C(=NOC
1-C
4烷基)-C
1-C
4烷基。
同樣較佳(構型2-2)的是式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
6烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;氧呾-3-基-CH
2-;或視需要地經鹵素或C
1-C
3鹵烷基取代的苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:
鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、C
1-C
6烷基,
視需要地經取代的C
3-C
6環烷基;
C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;
-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多三個取代基係獨立地選自由下列所組成之群組A:
C
4-C
6-烷基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
視需要地經取代的C
3-C
6環烷基;
-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-NHCO-C
3-C
4環烷基、-NHSO
2-苯基;
-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基和C
1-C
4鹵烷氧基;
及另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:
鹵素、羥基、-NH
2、-CN、-SF
5、-COOH、-CONH
2、-NO
2、C
1-C
6烷基,
視需要地經取代的C
3-C
6環烷基;
C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH(C
3-C
6環烷基)、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的萘基:
鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、C
1-C
6烷基,
視需要地經取代的C
3-C
6環烷基;
C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;
-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為選自由下列所組成群組之雜環:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基、9-員雜芳基和10-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:
鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-SF
5、-NH
2、C
1-C
6烷基,
視需要地經取代的C
3-C
6環烷基;
C
3-C
6環烷基-C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
3-C
6環烷硫基、C
3-C
6環烷亞磺醯基、C
3-C
6環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯硫基、苯亞磺醯基、苯磺醯基,其中在各情況下該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-C(=NOC
1-C
4烷基)H、-C(=NOC
1-C
4烷基)-C
1-C
4烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
6烷基:
C
1-C
3烷氧基-、C
1-C
3鹵烷氧基-、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
視需要地經一至二個選自由下列所組成群組之取代基取代的C
3-C
6環烷基:鹵素、-CN、-COOH、-CONH
2、C
1-C
6烷基、C
1-C
6鹵烷基、C
3-C
6環烷基、C
1-C
6烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;
及C
1-C
6鹵烷基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;鹵素;-CN; 視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;視需要地經一至二個選自由下列所組成群組之取代基取代的C
3-C
6環烷基:鹵素、-CN、-COOH、-CONH
2、C
1-C
6烷基、C
1-C
6鹵烷基、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;視需要地經一至二個選自由下列所組成群組之取代基取代的C
1-C
6鹵烷基:羥基、-CN、C
3-C
6環烷基、C
1-C
6烷氧基、C
1-C
6鹵烷氧基、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、和-CON(C
1-C
4烷基)
2;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;苯甲基,其中該苯基取代基係視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;視需要地經一至五個各自獨立地選自由下列所組成群組之取代基取代的苯基:鹵素、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、-SF
5、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;及雜環基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員飽和及部分不飽和雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:鹵素、=O(側氧基)、羥基、-CN、-COOH、-CONH
2、-NO
2、-NH
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成C
3-C
6-碳環或3-至6-員雜環系統,其視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基和C
1-C
3鹵烷氧基;
R
4為吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基,其中該吡啶、嘧啶、吡𠯤、嗒𠯤或5-員雜芳基係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-COOH、-CO
2-C
1-C
6烷基、-CONH
2、-CSNH
2、-NO
2、-NH
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
6烷硫基、C
1-C
6烷亞磺醯基、C
1-C
6烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NH(C
1-C
4烷基)、-N(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基,其中該烷基係視需要地經-CN、C
1-C
6烷基和C
1-C
4烷氧基取代;-NHCO-C
1-C
4鹵烷基、-NHCO-C
3-C
6環烷基,其中該環烷基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基或C
1-C
4烷氧基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基和C
1-C
3鹵烷基;-N(C
1-C
4烷基)CO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
3-C
6環烷基;-N(C
1-C
4烷基)CO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-N(SO
2C
1-C
3烷基)
2、-NH(SO
2C
1-C
3烷基)、-N(C
1-C
4烷基)(SO
2C
1-C
3烷基)、-N(SO
2C
1-C
3鹵烷基)
2、-NH(SO
2C
1-C
3鹵烷基)、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-CONH-SO
2-C
1-C
3烷基、-CON(C
1-C
4烷基)(C
3-C
6環烷基)、-CONH(C
1-C
4鹵烷基)、-CONH(C
3-C
6環烷基)、-CONH(C
3-C
6氰環烷基)、-C(=NOC
1-C
4烷基)H和-C(=NOC
1-C
4烷基)-C
1-C
4烷基;及-CONH-苯基,其中該苯基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
R
5為氫、鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
3-C
4環烷基、C
1-C
3烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷氧基C(O)-、(C
1-C
3烷氧基)
2CH-、-CO
2C
1-C
4烷基、-CONH(C
1-C
4烷基)、-CON(C
1-C
4烷基)
2、-NHCO-C
1-C
4烷基、-N(C
1-C
4烷基)CO-C
1-C
4烷基、-C(=NOC
1-C
4烷基)H、或-C(=NOC
1-C
4烷基)-C
1-C
4烷基。
進一步較佳(構型3-1)的是式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
3烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
3鹵烷基;C
2-C
4烯基;C
2-C
4鹵烯基;C
2-C
4炔基;C
2-C
4鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;氧呾-3-基-CH
2-;或視需要地經鹵素或C
1-C
3鹵烷基取代的苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多兩個取代基係獨立地選自由下列所組成之群組A::C
3-C
4環烷基、C
1-C
4烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯硫基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基或C
1-C
3鹵烷基;苯亞磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基或C
1-C
3鹵烷基;苯磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基或C
1-C
3鹵烷基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;-CONH(C
3-C
4環烷基)、-CON(C
1-C
3烷基)(C
3-C
4環烷基)、-C(=NOC
1-C
3烷基)-C
1-C
3烷基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基和C
1-C
3鹵烷氧基;
另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯基和5-至6-員雜芳基,其中該苯基和5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
或
R
2為噻吩、呋喃、吡唑、噻唑、異噻唑、㗁唑或異㗁唑,彼等各自視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、羥基、-CN、-NO
2、C
1-C
6烷基、C
3-C
4環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
6烷基:C
1-C
3烷氧基-、C
1-C
3鹵烷氧基-、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;苯基,其中該苯基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;C
3-C
6環烷基;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;苯甲基,其中該苯基取代基係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、和C
1-C
4鹵烷氧基;或雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基、和C
1-C
4烷氧基;或視需要地經一個選自由下列所組成群組之取代基取代的苯基:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成環丙烷、環丁烷、氧呾或四氫吡喃環,彼等視需要地經一至二個各自獨立地選自由下列所組成之群組取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
R
4為吡啶、嘧啶或噻唑,其中(A)該吡啶或嘧啶係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基和C
1-C
3鹵烷磺醯基及(B)該噻唑係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基和C
1-C
3鹵烷磺醯基;
R
5為氫、鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
3-C
4環烷基、或C
1-C
3烷氧基。
進一步較佳(構型3-2)也是式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經一個選自下列的取代基取代的C
1-C
3烷基:-CN、-CONH
2、-COOH、-NO
2和-Si(CH
3)
3;C
1-C
3鹵烷基;C
2-C
4烯基;C
2-C
4鹵烯基;C
2-C
4炔基;C
2-C
4鹵炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一或二個鹵素原子取代;氧呾-3-基-CH
2-;或視需要地經鹵素或C
1-C
3鹵烷基取代的苯甲基;
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經一至五個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:
鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
或
R
2為苯基、吡啶、嘧啶、吡𠯤或嗒𠯤,其中該苯基、吡啶、嘧啶、吡𠯤或嗒𠯤係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上及至少一個且最多兩個取代基係獨立地選自由下列所組成之群組A:
C
4-烷基、C
3-C
4環烷基,其中該C
3-C
4環烷基係視需要地經-CN或鹵素取代、C
1-C
4烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯硫基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
苯亞磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
苯磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、CN、C
1-C
6烷基和C
1-C
3鹵烷基;
-NHCO-C
1-C
3烷基、-NHCO-C
3-C
4環烷基、-NHSO
2-苯基;
-CONH(C
3-C
4環烷基)、-CON(C
1-C
3烷基)(C
3-C
4環烷基)、-C(=NOC
1-C
3烷基)-C
1-C
3烷基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基和C
1-C
3鹵烷氧基;
及另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:
鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基和5-至6-員雜芳基,其中該苯基和5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
或
R
2為噻吩、呋喃、吡唑、噻唑、異噻唑、㗁唑或異㗁唑,彼等各自視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:
鹵素、羥基、-CN、-NO
2、C
1-C
6烷基、C
3-C
4環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
6烷基:
C
1-C
3烷氧基-、C
1-C
3鹵烷氧基-、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基,其中該苯基係視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
2為視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的萘基:
鹵素、羥基、-CN、-NO
2、C
1-C
6烷基、C
3-C
4環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基
或
R
2為9-員或10-員雜芳基,其係視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:
鹵素、羥基、-CN、-NO
2、C
1-C
6烷基、C
3-C
4環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
3-C
4環烷硫基、C
3-C
4環烷亞磺醯基、C
3-C
4環烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基;
及苯基和5-至6-員雜芳基,其中該苯基或5-至6-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基和C
1-C
3鹵烷基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代的C
1-C
6烷基:C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、和C
1-C
3鹵烷磺醯基;C
3-C
6環烷基;C
1-C
6鹵烷基;C
2-C
6烯基;C
2-C
6鹵烯基;C
2-C
6炔基;C
2-C
6鹵炔基;苯甲基,其中該苯基取代基係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、和C
1-C
4鹵烷氧基;或雜環基-C
1-C
6烷基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基、和C
1-C
4烷氧基;或視需要地經一個選自由下列所組成群組之取代基取代的苯基:鹵素、-CN、-NO
2、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成環丙烷、環丁烷、氧呾或四氫吡喃環,彼等視需要地經一至二個各自獨立地選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
6烷基、C
1-C
3鹵烷基和C
1-C
4烷氧基;
R
4為吡啶、嘧啶、吡𠯤、嗒𠯤或噻唑,其中(A)該吡啶、嘧啶、吡𠯤或嗒𠯤係視需要地經一至三個選自由下列所組成群組之取代基取代:鹵素、-CN、-NH
2、-NO
2、-COOH、-CONH
2、-CSNH
2、-CO
2-C
1-C
3烷基、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基、C
1-C
3鹵烷磺醯基、-NHCO-C
1-C
3烷基、-NHCO-C
1-C
3鹵烷基、-NHCO-C
1-C
3氰烷基、-NHCO-C
3-C
4環烷基,其中該環烷基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、-CN、C
1-C
6烷基或C
1-C
4烷氧基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
1-C
3烷氧基和C
1-C
3鹵烷氧基;-NHSO
2-C
1-C
3烷基、-NHSO
2-C
1-C
3鹵烷基、-CONH(C
1-C
3烷基)、-CON(C
1-C
3烷基)
2、-CONH-SO
2-C
1-C
3烷基、-CON(C
1-C
3烷基)(C
3-C
6環烷基)、-CONH(C
1-C
3鹵烷基)、-CONH(C
3-C
6環烷基)、-CONH(1-氰基-C
3-C
6環烷基)、-CONH-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
1-C
3烷氧基和C
1-C
3鹵烷氧基;
及(B)該噻唑係視需要地經一至二個選自由下列所組成群組之取代基取代:鹵素、-CN、-NO
2、C
1-C
6烷基、C
3-C
6環烷基、C
1-C
3鹵烷基、C
1-C
4烷氧基、C
1-C
3鹵烷氧基、C
1-C
3烷硫基、C
1-C
3烷亞磺醯基、C
1-C
3烷磺醯基、C
1-C
3鹵烷硫基、C
1-C
3鹵烷亞磺醯基和C
1-C
3鹵烷磺醯基;
R
5為氫、鹵素、-CN、C
1-C
3烷基、C
1-C
3鹵烷基、C
3-C
4環烷基、或C
1-C
3烷氧基。
特佳 (構型4-1)的是式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經-CN、-Si(CH
3)
3或一至三個選自由下列所組成群組之取代基取代的C
1-C
3烷基:氟、氯或溴;C
2-C
4烯基;C
2-C
4炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯和溴;
R
2為苯基或吡啶,其中該苯基或吡啶係經一至三個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、乙硫基、乙亞磺醯基、乙磺醯基、異丙硫基、異丙亞磺醯基、異丙磺醯基、環丙硫基、環丙亞磺醯基、環丙磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基、和苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
或
R
2為苯基或吡啶,其中該苯基或吡啶係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上且一個取代基係獨立地選自由下列所組成之群組A:環丙基、甲硫基、甲亞磺醯基、甲磺醯基、乙硫基、乙亞磺醯基、乙磺醯基、異丙硫基、異丙亞磺醯基、異丙磺醯基、三級丁硫基、三級丁亞磺醯基、三級丁磺醯基、環丙硫基、環丙亞磺醯基、環丙磺醯基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲亞磺醯基、三氟甲磺醯基;苯磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、CN、甲基和三氟甲基;(環丙胺基)羰基、1-(甲氧基亞胺基)乙基;苯基和5-員雜芳基,其中該苯基或5-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基、三氟甲基和三氟甲氧基;
另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基和苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
或
R
2為噻吩、呋喃、吡唑、噻唑、㗁唑或異㗁唑,彼等各自視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基和苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
3烷基:甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基和苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
3烷基:甲基、乙基、異丙基、正丙基、環丙基、環丁基、二氟甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、和三氟甲磺醯基;環丙基、二氟甲基、三氟甲基、二氟甲基、三氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、乙炔基、2-丙烯-1-基和2-丙炔-1-基;苯甲基,其中該苯基取代基係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:氟、氯、溴、-CN, NO
2、甲基、三氟甲基和甲氧基;雜環基-甲基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、三氟甲基和甲氧基;及視需要地經一個選自由下列所組成群組之取代基取代的苯基:氟、氯、溴、-CN、-NO
2、甲基、三氟甲基和甲氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成環丙烷、環丁烷、氧呾或四氫吡喃環;
R
4為吡啶、嘧啶或噻唑,其中(A)該吡啶或嘧啶係視需要地經一至三個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、乙基、二氟甲基、三氟甲基、五氟乙基、環丙基、甲氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基和三氟甲磺醯基和(B)該噻唑係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、乙基、二氟甲基、三氟甲基、五氟乙基、環丙基、甲氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基和三氟甲磺醯基;
R
5為氫、氟、氯、溴、-CN、甲基、乙基、異丙基、二氟甲基、三氟甲基、環丙基、甲氧基、或乙氧基。
特佳者(構型4-2)亦為式(I)化合物,其中
X 為O或S;
Q
1和Q
2獨立地為CR
5或N,其條件為Q
1和Q
2中之至少一者為N;
Y 為直接鍵或CH
2;
R
1為氫;視需要地經-CN、-Si(CH
3)
3或一至三個選自由下列所組成群組之取代基取代的C
1-C
3烷基:氟、氯或溴;C
2-C
4烯基;C
2-C
4炔基;C
3-C
4環烷基-C
1-C
2烷基-,其中該C
3-C
4環烷基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯和溴;
R
2為苯基或吡啶,其中該苯基或吡啶係經一至三個各自獨立地選自由下列所組成群組之取代基取代,其條件為至少一個取代基在與鍵結至C=X基團之碳相鄰的任一碳上:
氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、乙硫基、乙亞磺醯基、乙磺醯基、異丙硫基、異丙亞磺醯基、異丙磺醯基、環丙硫基、環丙亞磺醯基、環丙磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基,
及苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
或
R
2為苯基或吡啶,其中該苯基或吡啶係經總共一至三個取代基取代,其條件為該(等)取代基不在與鍵結至C=X基團之碳相鄰的任一碳上且一個取代基係獨立地選自由下列所組成之群組A:
三級丁基、環丙基、1-氰環丙基、甲硫基、甲亞磺醯基、甲磺醯基、乙硫基、乙亞磺醯基、乙磺醯基、異丙硫基、異丙亞磺醯基、異丙磺醯基、三級丁硫基、三級丁亞磺醯基、三級丁磺醯基、環丙硫基、環丙亞磺醯基、環丙磺醯基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲亞磺醯基、三氟甲磺醯基、三氟乙亞磺醯基、三氟乙磺醯基;
苯磺醯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、CN、甲基和三氟甲基;
(環丙胺基)羰基、1-(甲氧基亞胺基)乙基、乙醯胺基、(環丙羰基)胺基、(苯磺醯基)胺基;
及苯基和5-員雜芳基,其中該苯基或5-員雜芳基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基、三氟甲基和三氟甲氧基;
及另一個至二個視需要之取代基各自獨立地選自由下列所組成之群組B:
氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基
及苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基;
或
R
2為噻吩、呋喃、吡唑、噻唑、㗁唑或異㗁唑,彼等各自視需要地經一至三個各自獨立地選自由下列所組成群組之取代基取代:
氟、氯、溴、-CN、-NO
2、甲基、環丙基、二氟甲基、三氟甲基、甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基
及苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基
或
R
2為經一個選自由下列所組成群組之取代基取代的C
1-C
3烷基:
甲氧基、三氟甲氧基、二氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基
及苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、二氟甲基和三氟甲基
或
R
2為萘基;或吡唑并[1.5-a]吡啶-2-基,視需要地經三氟甲基或氯取代;
R
3a、R
3b係獨立地選自由下列所組成之群組:氫;視需要地經一至三個獨立地選自由下列所組成群組之取代基取代的C
1-C
3烷基:甲基、乙基、異丙基、正丙基、環丙基、環丁基、二氟甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、和三氟甲磺醯基;環丙基、二氟甲基、三氟甲基、二氟甲基、三氟甲基、2,2-二氟乙基、2,2,2-三氟乙基、乙炔基、2-丙烯-1-基和2-丙炔-1-基;苯甲基,其中該苯基取代基係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、NO
2、甲基、三氟甲基和甲氧基;雜環基-甲基,其中該雜環基取代基係選自由下列所組成之群組:4-至10-員雜環基、5-員雜芳基和6-員雜芳基,彼等各自係視需要地經一至三個獨立地選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、三氟甲基和甲氧基;及視需要地經一個選自由下列所組成群組之取代基取代的苯基:氟、氯、溴、-CN、-NO
2、甲基、三氟甲基和甲氧基;
或
R
3a、R
3b與彼等所連接的碳一起形成環丙烷、環丁烷、氧呾或四氫吡喃環;
R
4為吡啶、嘧啶、吡𠯤或噻唑,其中(A)該吡啶、嘧啶或吡𠯤係視需要地經一至三個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NH
2、-NO
2、-COOH、-CONH
2、-CSNH
2、-CO
2Me、甲基、乙基、二氟甲基、三氟甲基、五氟乙基、環丙基、甲氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基、三氟甲磺醯基、-NHCO-甲基、-NHCO-三氟甲基、-NHCO-CH
2CN、-NHCO-環丙基、-NHCO-1-氰環丙基、-NHSO
2-甲基、-NHSO
2-三氟甲基、-NHCO-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、甲基、二氟甲基、三氟甲基、甲氧基、二氟甲氧基和三氟甲氧基;-CONH-甲基、-CONH-SO
2-甲基、-CON-(N-甲基)-N-環丙基、-CONH-二氟乙基、-CONH-三氟乙基、-CONH-環丙基、-CONH-1-氰環丙基、-CONH-苯基,其中該苯基係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、甲基、二氟甲基、三氟甲基、甲氧基、二氟甲氧基和三氟甲氧基;
及(B)該噻唑係視需要地經一至二個選自由下列所組成群組之取代基取代:氟、氯、溴、-CN、-NO
2、甲基、乙基、二氟甲基、三氟甲基、五氟乙基、環丙基、甲氧基、二氟甲氧基、三氟甲氧基、甲硫基、甲亞磺醯基、甲磺醯基、二氟甲硫基、二氟甲亞磺醯基、二氟甲磺醯基、三氟甲硫基、三氟甲亞磺醯基和三氟甲磺醯基;
R
5為氫、氟、氯、溴、-CN、甲基、乙基、異丙基、二氟甲基、三氟甲基、環丙基、甲氧基、或乙氧基。
非常特佳(構型5-1)的是式(I)化合物,其中
X 為O;
Q
1為N;
Q
2為CR
5;
Y 為直接鍵;
R
1為氫、環丙基-CH
2-、3,3,3-三氟丙基、乙基或2,2-二氟乙基;
R
23-氯-2-氟-5-(三氟甲基)苯基、3-氯-5-(甲磺醯基)苯基、5-(甲磺醯基)吡啶-3-基、3-(甲磺醯基)苯基、3-(三氟甲磺醯基)苯基、5-[(三氟甲基)磺醯基]吡啶-3-基、3-氯-5-[(環丙胺基)羰基]苯基、3-環丙基-5-(三氟甲基)苯基、2,3,5-三氯苯基、3-苯基-5-(三氟甲基)苯基、[3-氯-5-(三氟甲基)苯基]甲基、3-(4-氟苯基)-5-(三氟甲基)苯基、2-氯苯基、2,5-二氯苯基、2,3,4-三氯苯基、2,3-二氯苯基、2,4-二氯苯基、2,6-二氟苯基、3-氯-5-(三氟甲磺醯基)苯基、5-氯-3-噻吩基、3,4,5-三氯-2-噻吩基、2,5-二氯-3-噻吩基、4,5-二氯-2-噻吩基、1-甲基-5-(三氟甲基)-1H-吡唑-3-基、4-氯-1-甲基-3-(三氟甲基)-1H-吡唑-5-基、5-甲基-1,2-㗁唑-3-基、5-環丙基-1,2-㗁唑-3-基、3-氯-1,2-㗁唑-5-基、2-氯-1,3-噻唑-5-基、1-甲基-1H-吡唑-4-基、5-氯-1-甲基-1H-吡唑-4-基、3-氯-5-環丙磺醯基苯基、3-氯-5-(4-氟苯基)磺醯基苯基、3-氯-5-乙磺醯基苯基、3-環丙基-5-氟苯基、3-氯-5-(異丙硫基)苯基、3-氯-5-(1H-吡唑-1-基)苯基、3-氯-5-(1H-1,2,4-三唑-1-基)苯基、3-氯-5-環丙基苯基、3-氯-5-異丙磺醯基苯基、1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-基、3-環丙基-5-(三氟甲氧基)苯基、4-(三氟甲磺醯基)苯基、3-氯-5-[1-(甲氧基亞胺基)乙基]苯基、3-(三級丁硫基)-5-氯苯基、1-(4-氟苯基)-5-(三氟甲基)-1H-吡唑-3-基、5-[4-(三氟甲氧基)苯基]吡啶-3-基、3-氯-5-甲硫基苯基(methylsulfanylphenyl)、3-氯-5-甲亞磺醯基苯基、或3-苯甲醯胺基-5-氯苯基;
R
3a為氫、甲基或甲氧基甲基;
R
3b為甲基或甲氧基甲基,若R
3a為氫;
R
3b為氫,若R
3a為甲基或甲氧基甲基;
R
4為2-吡啶基、2-嘧啶-2-基、2-嘧啶-4-基、5-氯吡啶-2-基、4-氯吡啶-2-基、5-氰吡啶-2-基、4-氰基-2-吡啶基、5-(三氟甲基)-吡啶-2-基、5-(二氟甲氧基)吡啶-2-基、5-(三氟甲硫基)吡啶-2-基、3,5-二氟-2-吡啶基、5-氯-3-氟-2-吡啶基、5-氟嘧啶-2-基、5-氯嘧啶-2-基、2-吡𠯤-2-基或1,3-噻唑-2-基;
R
5為氫或甲基。
非常特佳者(構型5-2)亦為式(I)化合物,其中
X 為O或S;
Q
1為N
Q
2為CR
5Y 為直接鍵或CH
2;
R
1為氫、甲基、乙基、2-(三甲矽基)乙基、2,2-二氟乙基、2,2,2-三氟乙基、3,3,3-三氟丙基、或環丙基-CH
2- ;
R
23-氯-2-氟-5-(三氟甲基)苯基、3-氯-5-(甲磺醯基)苯基、3-甲磺醯基-5-(三氟甲基)苯基、5-(甲磺醯基)吡啶-3-基、3-(甲磺醯基)苯基、3-(三氟甲磺醯基)苯基、5-[(三氟甲基)磺醯基]吡啶-3-基、3-氯-5-[(環丙胺基)羰基]苯基、3-環丙基-5-(三氟甲基)苯基、2,3,5-三氯苯基、3-苯基-5-(三氟甲基)苯基、[3-氯-5-(三氟甲基)苯基]甲基、3-(4-氟苯基)-5-(三氟甲基)苯基、2-氯苯基、2,5-二氯苯基、2,3,4-三氯苯基、2,3-二氯苯基、2,4-二氯苯基、2,6-二氟苯基、3-氟-5-(三氟甲磺醯基)苯基、3-氯-5-(三氟甲磺醯基)苯基、5-氯-3-噻吩基、3,4,5-三氯-2-噻吩基、2,5-二氯-3-噻吩基、4,5-二氯-2-噻吩基、1-甲基-5-(三氟甲基)-1H-吡唑-3-基、4-氯-1-甲基-3-(三氟甲基)-1H-吡唑-5-基、5-甲基-1,2-㗁唑-3-基、5-環丙基-1,2-㗁唑-3-基、3-氯-1,2-㗁唑-5-基、2-氯-1,3-噻唑-5-基、1-甲基-1H-吡唑-4-基、5-氯-1-甲基-1H-吡唑-4-基、3-氯-5-環丙磺醯基苯基、3-氯-5-(4-氟苯基)磺醯基苯基、3-氯-5-乙磺醯基苯基、3-環丙基-5-氟苯基、3-氯-5-(異丙硫基)苯基、3-氯-5-(1H-吡唑-1-基)苯基、3-氯-5-(1H-1,2,4-三唑-1-基)苯基、3-三級丁基-5-氯苯基、3-三級丁基-5-溴苯基、3-氟-5-環丙基苯基、3-氯-5-環丙基苯基、3-氯-5-異丙磺醯基苯基、1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-基、3-環丙基-5-(三氟甲氧基)苯基、4-(三氟甲磺醯基)苯基、3-氯-5-[1-(甲氧基亞胺基)乙基]苯基、3-(三級丁硫基)-5-氯苯基、1-(4-氟苯基)-1H-吡唑-4-基、1-(4-氟苯基)-5-(三氟甲基)-1H-吡唑-3-基、5-[4-(三氟甲氧基)苯基]吡啶-3-基、3-氯-5-甲硫基苯基、3-氯-5-甲亞磺醯基苯基、3-苯甲醯胺基-5-氯苯基、3-(三級丁磺醯基)-5-氯苯基、5-[4-(三氟甲基)苯基]-吡啶-3-基、5-[4-(三氟甲氧基)苯基]-吡啶-3-基、5-(4-氯苯基)吡啶-3-基、5-(4-氟苯基)吡啶-3-基、3-氯-5-[(苯磺醯基)胺基]苯基、3-乙醯胺基-5-氯苯基、3-氯-5-[(環丙羰基)胺基]苯基、3-氯-5-[(2,2,2-三氟乙基)亞磺醯基]苯基、3-氯-5-[(2,2,2-三氟乙基)磺醯基]苯基、3-氯-5-[3-(三氟甲基)-1H-吡唑-1-基]苯基、3,5-雙(甲磺醯基)苯基、吡唑并[1,5-a]吡啶-2-基、7-(三氟甲基)吡唑并[1,5-a]吡啶-2-基、6-氯吡唑并[1,5-a]吡啶-2-基、萘-2-基、3-[4’-(三氟甲氧基)苯基]-苯基、3-(4’-氟苯基)-5-(三氟甲基)苯基或3-氯-5-(1-氰環丙基)苯基;
R
3a為氫、甲基或甲氧基甲基;
R
3b為甲基或甲氧基甲基,若R
3a為氫;
R
3b為氫,若
3a為甲基或甲氧基甲基;
R
3a和R
3b與彼等所連接的碳一起形成環丙烷環;
R
4為吡啶-2-基、嘧啶-2-基、嘧啶-4-基、5-氟嘧啶-2-基、5-氯嘧啶-2-基、5-氰嘧啶-2-基、5-(三氟甲基)嘧啶-2-基、5-甲基嘧啶-2-基、5-氟吡啶-2-基、5-氯吡啶-2-基、2-氯吡啶-4-基、5-氰吡啶-2-基、4-氰基-吡啶-2-基、6-氰基-吡啶-2-基、5-甲氧基-吡啶-2-基、5-(三氟甲基)-吡啶-2-基、5-(二氟甲氧基)吡啶-2-基、5-(三氟甲硫基)吡啶-2-基、5-硝吡啶-2-基、5-胺吡啶-2-基、3,5-二氟吡啶-2-基、5-氯-3-氟吡啶-2-基、吡啶-2-基-5-甲酸、吡啶-2-基-5-甲酸甲酯、N-甲基-吡啶-2-基-5-甲醯胺、N-環丙基-吡啶-2-基-5-甲醯胺、N-環丙基-N-甲基-吡啶-2-基-5-甲醯胺、N-(1-氰環丙基)-吡啶-2-基-5-甲醯胺、N-(2,2-二氟乙基)-吡啶-2-基-5-甲醯胺、N-(2,2,2-三氟乙基)-吡啶-2-基-5-甲醯胺、N-甲磺醯基-吡啶-2-基-5-甲醯胺、N-(4-氟苯基)-吡啶-2-基-5-甲醯胺、5-乙醯胺基吡啶-2-基、5-(三氟乙醯胺基)-吡啶-2-基、5-(2-氰乙醯胺基)-吡啶-2-基、5-[(環丙羰基)胺基]吡啶-2-基、5-[(1-氰環丙羰基)胺基]-吡啶-2-基、5-(甲烷磺醯胺基)-吡啶-2-基、5-(三氟甲基磺醯胺基)-吡啶-2-基、5-[(4-氟苯甲醯基)胺基]吡啶-2-基、吡𠯤-2-基、2-氰基-吡𠯤-5-基、或1,3-噻唑-2-基;
R
5為氫、甲基或三氟甲基。
在另一較佳實施態樣中,本發明關於式(I’)化合物
(I’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
3a、R
3b、R
4和R
5具有構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中所給的意義。
在另一進一步較佳實施態樣中,本發明關於式(I’)化合物
(I’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
3a、R
3b、R
4和R
5具有構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中所給的意義。
在式(I’)化合物之另一較佳實施態樣中,Q
1表示N或CR
5和Q
2表示N且所有其他結構單元Y、R
1、R
2、R
3a、R
3b、R
4和R
5具有上述構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中的意義。
在式(I’)化合物之另一進一步較佳實施態樣中,Q
1表示N或CR
5和Q
2表示N且所有其他結構單元Y、R
1、R
2、R
3a、R
3b、R
4和R
5具有上述構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中的意義。
在式(I’)化合物之其他進一步較佳實施態樣中,Q
1表示N和Q
2表示CR
5且所有其他結構單元Y、R
1、R
2、R
3a、R
3b、R
4和R
5具有上述構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中的意義。
在式(I’)化合物之另一進一步較佳實施態樣中,Q
1表示N和Q
2表示CR
5且所有其他結構單元Y、R
1、R
2、R
3a、R
3b、R
4和R
5具有上述構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中的意義。
其中,特佳者為下示構型:
化合物之式 | 具有依照下列之Q 1 | 具有依照下列之Q 2 | 具有依照下列之所有其他結構單元 |
I’ | N | CR 5 | 構型(1-1) |
I’ | N | CR 5 | 構型(2-1) |
I’ | N | CR 5 | 構型(3-1) |
I’ | N | CR 5 | 構型(4-1) |
I’ | N | CR 5 | 構型(5-1) |
I’ | CR 5 | N | 構型(1-1) |
I’ | CR 5 | N | 構型(2-1) |
I’ | CR 5 | N | 構型(3-1) |
I’ | CR 5 | N | 構型(4-1) |
I’ | CR 5 | N | 構型(5-1) |
I’ | N | N | 構型(1-1) |
I’ | N | N | 構型(2-1) |
I’ | N | N | 構型(3-1) |
I’ | N | N | 構型(4-1) |
I’ | N | N | 構型(5-1) |
I’ | N | CR 5 | 構型(1-2) |
I’ | N | CR 5 | 構型(2-2) |
I’ | N | CR 5 | 構型(3-2) |
I’ | N | CR 5 | 構型(4-2) |
I’ | N | CR 5 | 構型(5-2) |
I’ | CR 5 | N | 構型(1-2) |
I’ | CR 5 | N | 構型(2-2) |
I’ | CR 5 | N | 構型(3-2) |
I’ | CR 5 | N | 構型(4-2) |
I’ | CR 5 | N | 構型(5-2) |
I’ | N | N | 構型(1-2) |
I’ | N | N | 構型(2-2) |
I’ | N | N | 構型(3-2) |
I’ | N | N | 構型(4-2) |
I’ | N | N | 構型(5-2) |
在另一較佳實施態樣中,本發明關於式(I’’)化合物,其中R
3b為C
1-C
3烷基,尤佳為Me,及R
3a為H
(I’’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
4和R
5具有構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中所給的意義。
在另一進一步較佳實施態樣中,本發明關於式(I’’)化合物,其中R
3b為C
1-C
3烷基,尤佳為Me,及R
3a為H
(I’’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
4和R
5具有構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中所給的意義。
在另一較佳實施態樣中,本發明關於式(I’’’)化合物,其中R
3b為C
1-C
3烷基,尤佳為Me,及R
3a為H
(I’’’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
4和R
5具有構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中所給的意義。
在另一進一步較佳實施態樣中,本發明關於式(I’’’)化合物,其中R
3b為C
1-C
3烷基,尤佳為Me,及R
3a為H
(I’’’),
其中結構單元Y、Q
1、Q
2、R
1、R
2、R
4和R
5具有構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中所給的意義。
在一進一步較佳實施態樣中,本發明關於式(I’p1)化合物
(I’p1),
其中Y為直接鍵及結構單元R
1、R
2、R
3a、R
3b、R
4和R
5具有下表所給的意義:
項目 | R 1下列構型中所給的意義 | R 2下列構型中所給的意義 | R 3a、R 3b下列構型中所給的意義 | R 4下列構型中所給的意義 | R 5下列構型中所給的意義 |
1 | 4-1 | 4-1 | 5-1 | 4-1 | 4-1 |
2 | 4-1 | 4-1 | 5-1 | 4-1 | 5-1 |
3 | 4-1 | 4-1 | 5-1 | 5-1 | 4-1 |
4 | 4-1 | 5-1 | 5-1 | 4-1 | 4-1 |
5 | 4-1 | 5-1 | 5-1 | 5-1 | 4-1 |
6 | 4-1 | 5-1 | 5-1 | 4-1 | 5-1 |
7 | 4-1 | 4-1 | 5-1 | 5-1 | 5-1 |
8 | 4-1 | 5-1 | 5-1 | 5-1 | 5-1 |
9 | 5-1 | 4-1 | 5-1 | 4-1 | 4-1 |
10 | 5-1 | 4-1 | 5-1 | 4-1 | 5-1 |
11 | 5-1 | 4-1 | 5-1 | 5-1 | 4-1 |
12 | 5-1 | 5-1 | 5-1 | 4-1 | 4-1 |
13 | 5-1 | 5-1 | 5-1 | 5-1 | 4-1 |
14 | 5-1 | 5-1 | 5-1 | 4-1 | 5-1 |
15 | 5-1 | 4-1 | 5-1 | 5-1 | 5-1 |
16 | 5-1 | 5-1 | 5-1 | 5-1 | 5-1 |
17 | 4-1 | 3-1 | 5-1 | 4-1 | 4-1 |
18 | 4-1 | 3-1 | 5-1 | 4-1 | 5-1 |
19 | 4-1 | 3-1 | 5-1 | 5-1 | 4-1 |
20 | 4-1 | 3-1 | 5-1 | 5-1 | 5-1 |
21 | 5-1 | 3-1 | 5-1 | 4-1 | 4-1 |
22 | 5-1 | 3-1 | 5-1 | 4-1 | 5-1 |
23 | 5-1 | 3-1 | 5-1 | 5-1 | 4-1 |
24 | 5-1 | 3-1 | 5-1 | 5-1 | 5-1 |
在另一進一步較佳實施態樣中,本發明關於式(I’p1)化合物
(I’p1),
其中Y為直接鍵及結構單元R
1、R
2、R
3a、R
3b、R
4和R
5具有下表所給的意義:
項目 | R 1下列構型中所給的意義 | R 2下列構型中所給的意義 | R 3a、R 3b下列構型中所給的意義 | R 4下列構型中所給的意義 | R 5下列構型中所給的意義 |
1 | 4-2 | 4-2 | 5-2 | 4-2 | 4-2 |
2 | 4-2 | 4-2 | 5-2 | 4-2 | 5-2 |
3 | 4-2 | 4-2 | 5-2 | 5-2 | 4-2 |
4 | 4-2 | 5-2 | 5-2 | 4-2 | 4-2 |
5 | 4-2 | 5-2 | 5-2 | 5-2 | 4-2 |
6 | 4-2 | 5-2 | 5-2 | 4-2 | 5-2 |
7 | 4-2 | 4-2 | 5-2 | 5-2 | 5-2 |
8 | 4-2 | 5-2 | 5-2 | 5-2 | 5-2 |
9 | 5-2 | 4-2 | 5-2 | 4-2 | 4-2 |
10 | 5-2 | 4-2 | 5-2 | 4-2 | 5-2 |
11 | 5-2 | 4-2 | 5-2 | 5-2 | 4-2 |
12 | 5-2 | 5-2 | 5-2 | 4-2 | 4-2 |
13 | 5-2 | 5-2 | 5-2 | 5-2 | 4-2 |
14 | 5-2 | 5-2 | 5-2 | 4-2 | 5-2 |
15 | 5-2 | 4-2 | 5-2 | 5-2 | 5-2 |
16 | 5-2 | 5-2 | 5-2 | 5-2 | 5-2 |
17 | 4-2 | 3-2 | 5-2 | 4-2 | 4-2 |
18 | 4-2 | 3-2 | 5-2 | 4-2 | 5-2 |
19 | 4-2 | 3-2 | 5-2 | 5-2 | 4-2 |
20 | 4-2 | 3-2 | 5-2 | 5-2 | 5-2 |
21 | 5-2 | 3-2 | 5-2 | 4-2 | 4-2 |
22 | 5-2 | 3-2 | 5-2 | 4-2 | 5-2 |
23 | 5-2 | 3-2 | 5-2 | 5-2 | 4-2 |
24 | 5-2 | 3-2 | 5-2 | 5-2 | 5-2 |
根據另一態樣,本發明涵蓋可用於製備通式(I)之化合物之中間化合物,同上。
特別地,本發明涵蓋通式(
a*)之中間化合物:
其中結構單元Y、R
1、R
2、R
3a和R
3b具有構型(1-1)或構型(2-1)或構型(3-1)或構型(4-1)或構型(5-1)中所給的意義。
特別地,本發明也涵蓋通式(
a*)之中間化合物:
其中結構單元Y、R
1、R
2、R
3a和R
3b具有構型(1-2)或構型(2-2)或構型(3-2)或構型(4-2)或構型(5-2)中所給的意義。
特別地,本發明涵蓋通式(
b*)之中間化合物:
其中:
E為氫或C
1-C
6烷基;
A為-CN、氯或氟;
L為S、SO或SO
2。
特別地,本發明涵蓋通式(
c*)之中間化合物:
其中:
E為氫或C
1-C
6烷基;
A為溴、氯、氟、-CN或三氟甲基,較佳為氯。
特別地,本發明涵蓋通式(
d*)之中間化合物:
其中:
E為氫或C
1-C
6烷基;
A為溴、氯或氟,較佳為氯;
L為S、SO或SO
2,較佳為S或SO
2,更佳為SO
2;
J為乙基、異丙基、三級丁基、環丙基、2,2,2-三氟乙基或4-氟苯基;
及,其中式(
d*)化合物不為3-(乙硫基(ethylsulfanyl))-5-氟苯甲酸或3-(三級丁硫基(tert-butylsulfanyl))-5-氟苯甲酸。
本發明也涵蓋化合物3-環丙基-5-(三氟甲氧基)苯甲酸和3-環丙基-5-(三氟甲氧基)苯甲酸甲酯。
取決於取代基的性質,式(I)化合物也可能於立體異構物的形式,即於幾何及/或光學異構物或不同組成之異構物混合物的形式。本發明提供純立體異構物及此等異構物的任何混合物,即使其通常只為本文討論的式(I)化合物。
然而,根據本發明較佳者為使用式(I)化合物及其鹽的光學活性立體異構形式。
本發明因此關於用於控制動物害蟲(包括節肢動物且特別是昆蟲)之純鏡像異構物和非鏡像異構物及其混合物。
如果合適,式(I)化合物可以各種多晶形式存在或呈各種多晶形式之混合物存在。純多晶型物和多晶型物混合物均由本發明提供且可根據本發明使用。
定義
熟習該項技術者知曉,若未明確說明,則本申請案所使用的用語"一(a)"或"一(an)"可視情況意指"一(1)個"、"一(1)或多個"或"至少一(1)個"。
就本文所述的全部結構而言,諸如環系統和基團,相鄰的原子必須不為-O-O-或-O-S-。
具有可變數量之可能碳原子(C原子)的結構在本申請案中可稱為C
碳原子下限-C
碳原子上限結構(C
LL-C
UL結構),以便因此可更明確地規定。實例:烷基可由3至10個碳原子組成且該情況係對應於C
3-C
10-烷基。由碳原子與雜原子組成的環結構可稱作"LL-至UL-員"結構。6-員環結構的一實例為甲苯(經甲基取代的6-員環結構)。
若取代基的總稱(例如C
LL-C
UL-烷基)係位於複合取代基的末端(例如C
LL-C
UL-環烷基-C
LL-C
UL-烷基),則在該複合取代基開端的取代基(C
LL-C
UL-環烷基)則可經後者取代基C
LL-C
UL-烷基相同或不同地且獨立地單-或多取代。在本申請案用於化學基團、環狀系統與環狀基團的所有總稱可透過加入"C
LL-C
UL"或"LL-至UL-員"更明確地規定。
在上式中所給之符號的定義中,使用下列取代基的一般表示之總稱:
鹵素關於第7主族元素,較佳為氟、氯、溴和碘,更佳為氟、氯和溴,且甚至更佳為氟和氯。
雜原子的實例為N、O、S、P、B、Si。較佳地,術語"雜原子"關於N、S和O。
根據本發明,"烷基" – 就其本身或作為化學基團的一部分 – 表示較佳具有1至6個碳原子之直鏈或分支烴,例如甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丙基、1,3-二甲基丁基、1,4-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基和2-乙基丁基。較佳者亦為具有1至4個碳原子之烷基諸如(尤其是)甲基、乙基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基或三級丁基。本發明的烷基可經一或多個相同或不同的基團取代。
根據本發明,"烯基" – 就其本身或作為化學基團的一部分 – 表示較佳具有2至6個碳原子和至少一個雙鍵之直鏈或分支烴,例如乙烯基、2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-2-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基。較佳者亦為具有2至4個碳原子之烯基諸如(尤其是)2-丙烯基、2-丁烯基或1-甲基-2-丙烯基。本發明的烯基可經一或多個相同或不同的基團取代。
根據本發明,"炔基" – 就其本身或作為化學基團的一部分 – 表示較佳具有2至6個碳原子和至少一個參鍵之直鏈或分支烴,例如2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基和2,5-己二炔基。較佳者亦為具有2至4個碳原子之炔基諸如(尤其是)乙炔基、2-丙炔基或2-丁炔基-2-丙烯基。本發明的炔基可經一或多個相同或不同的基團取代。
根據本發明,"環烷基" – 就其本身或作為化學基團的一部分 – 表示較佳具有3至10個碳原子之單-、雙-或三環烴,例如環丙基、環丁基、環戊基、環己基、環庚基、環辛基、雙環[2.2.1]庚基、雙環[2.2.2]辛基或金剛烷基。較佳者亦為具有3、4、5、6或7個碳原子之環烷基,諸如,尤其是環丙基或環丁基。本發明的環烷基可經一或多個相同或不同的基團取代。
根據本發明,"烷基環烷基"表示較佳具有4至10或4至7個碳原子之單-、雙-或三環的烷基環烷基,例如甲基環丙基、乙基環丙基、異丙基環丁基、3-甲基環戊基和4-甲基環己基。較佳者亦為具有4、5或7個碳原子之烷基環烷基諸如(尤其是)乙基環丙基或4-甲基環己基。本發明的烷基環烷基可經一或多個相同或不同的基團取代。
根據本發明,"環烷基烷基"表示較佳具有4至10或4至7個碳原子之單-、雙-或三環的環烷基烷基,例如環丙基甲基、環丁基甲基、環戊基甲基、環己基甲基和環戊基乙基。較佳者亦為具有4、5或7個碳原子之環烷基烷基諸如(尤其是)環丙基甲基或環丁基甲基。本發明的環烷基烷基可經一或多個相同或不同的基團取代。
根據本發明,"羥烷基"表示較佳具有1至6個碳原子之直鏈或分支醇,例如甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、二級丁醇和三級丁醇。較佳者亦為具有1至4個碳原子之羥烷基。本發明的羥烷基可經一或多個相同或不同的基團取代。
根據本發明,"烷氧基"表示較佳具有1至6個碳原子之直鏈或分支O-烷基,例如甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基和三級丁氧基。較佳者亦為具有1至4個碳原子之烷氧基。本發明的烷氧基可經一或多個相同或不同的基團取代。
根據本發明,"烷硫基(alkylthio或alkylsulfanyl)"表示較佳具有1至6個碳原子之直鏈或分支S-烷基,例如甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基和三級丁硫基。較佳者亦為具有1至4個碳原子之烷硫基。本發明的烷硫基可經一或多個相同或不同的基團取代。
根據本發明,"烷亞磺醯基"表示較佳具有1至6個碳原子之直鏈或分支烷亞磺醯基,例如甲亞磺醯基、乙亞磺醯基、正丙亞磺醯基、異丙亞磺醯基、正丁亞磺醯基、異丁亞磺醯基、二級丁亞磺醯基和三級丁亞磺醯基。較佳者亦為具有1至4個碳原子之烷亞磺醯基。本發明的烷亞磺醯基可經一或多個相同或不同的基團取代且包含二種鏡像異構物。
根據本發明,"烷磺醯基"表示較佳具有1至6個碳原子之直鏈或分支烷磺醯基,例如甲磺醯基、乙磺醯基、正丙磺醯基、異丙磺醯基、正丁磺醯基、異丁磺醯基、二級丁磺醯基和三級丁磺醯基。較佳者亦為具有1至4個碳原子之烷磺醯基。本發明的烷磺醯基可經一或多個相同或不同的基團取代。
根據本發明,"環烷硫基(cycloalkylthio或cycloalkylsulfanyl)”表示較佳具有3至6個碳原子之-S-環烷基,例如環丙硫基、環丁硫基、環戊硫基、環己硫基。較佳者亦為具有3至5個碳原子之環烷硫基。本發明的環烷硫基可經一或多個相同或不同的基團取代。
根據本發明,“環烷亞磺醯基”表示示較佳具有3至6個碳原子之-S(O)-環烷基,例如環丙亞磺醯基、環丁亞磺醯基、環戊亞磺醯基、環己亞磺醯。較佳者亦為具有3至5個碳原子之環烷亞磺醯基。本發明的環烷亞磺醯基可經一或多個相同或不同的基團取代且包含二種鏡像異構物。
根據本發明,“環烷磺醯基”表示較佳具有3至6個碳原子之-SO
2-環烷基,例如環丙磺醯基、環丁磺醯基、環戊磺醯基、環己磺醯基。較佳者亦為具有3至5個碳原子之環烷磺醯基。本發明的環烷磺醯基可經一或多個相同或不同的基團取代。
根據本發明,"苯硫基(phenylthio或phenylsulfanyl)"表示-S-苯基,例如苯硫基。本發明的苯硫基可經一或多個相同或不同的基團取代。
根據本發明,“苯亞磺醯基”表示-S(O)-苯基,例如苯亞磺醯基。本發明的苯亞磺醯基可經一或多個相同或不同的基團取代且包含二種鏡像異構物。
根據本發明,“苯磺醯基”表示-SO
2-苯基例如苯磺醯基。本發明的苯磺醯基可經一或多個相同或不同的基團取代。
根據本發明,"烷羰基"表示較佳具有2至7個碳原子之直鏈或分支烷基-C(=O),諸如甲羰基、乙羰基、正丙羰基、異丙羰基、二級丁基羰基和三級丁基羰基。較佳者亦為具有1至4個碳原子之烷羰基。本發明的烷羰基可經一或多個相同或不同的基團取代。
根據本發明,"烷氧羰基" - 單獨或作為化學基團之組分 - 表示於該烷氧基部分中較佳具有1至6個碳原子或具有1至4個碳原子之直鏈或分支烷氧羰基,例如甲氧羰基、乙氧羰基、正丙氧羰基、異丙氧羰基、二級丁氧羰基和三級丁氧羰基。本發明的烷氧羰基可經一或多個相同或不同的基團取代。
根據本發明,"烷胺羰基"表示於該烷基部分中較佳具有1至6個碳原子或1至4個碳原子之直鏈或分支烷胺羰基,例如甲胺羰基、乙胺羰基、正丙胺羰基、異丙胺羰基、二級丁胺羰基和三級丁胺羰基。本發明的烷胺羰基可經一或多個相同或不同的基團取代。
根據本發明,"
N,N-二烷胺羰基"表示於該烷基部分中較佳具有1至6個碳原子或1至4個碳原子之直鏈或分支N,N-二烷胺羰基,例如N,N-二甲胺羰基、N,N-二乙胺羰基、N,N-二(正丙胺基)羰基、N,N-二(異丙胺基)羰基和N,N-二-(二級丁胺基)羰基。本發明的N,N-二烷胺羰基可經一或多個相同或不同的基團取代。
根據本發明,"芳基"表示較佳具有6至14個(尤其是6至10個)環碳原子之單-、雙-或多環芳族系統,例如苯基、萘基、蒽基、菲基,較佳地表示苯基。此外,芳基亦表示多環系統諸如四氫萘基、茚基、二氫茚基、茀基、聯苯基,其中該鍵結位置係在芳族系統上。本發明的芳基可經一或多個相同或不同的基團取代。
經取代的芳基的實例為芳基烷基,其在C
1-C
4-烷基及/或C
6-C
14-芳基部分可經一或多個相同或不同的基團取代。該等芳基烷基的實例包括苯甲基和1-苯基乙基。
根據本發明,"雜環(heterocycle)"、"雜環(heterocyclic ring)"或"雜環系統"表示具有至少一個環的碳環系統,其中至少一個碳原子係經雜原子置換,較佳經由下列所組成群組之雜原子置換:N、O、S、P、B、Si、Se,且其為飽和、不飽和或雜芳族且可為未經取代或經取代,其中該鍵結位置在環原子上。除非另有不同地定義,否則該雜環較佳地在雜環中含有3至9個環原子(尤其是3至6個環原子)及一或多個(較佳為1至4個,尤其是1、2或3個)雜原子(較佳選自由N、O、及S組成之群組),雖然應沒有兩個氧原子彼此直接相鄰。該等雜環通常含有不超過4個氮原子及/或不超過2個氧原子及/或不超過2個硫原子。當該雜環基或雜環係視需要地經取代時,其可稠合至其他碳環或雜環。在視需要地經取代的雜環基的情況下,本發明也包括多環系統,例如8-氮雜雙環[3.2.1]辛基或1-氮雜雙環[2.2.1]庚基。在視需要地經取代的雜環的情況下,本發明也包括螺環系統,例如1-氧雜-5-氮雜螺[2.3]己基。
本發明的雜環基為(例如)哌啶基、哌𠯤基、嗎福林基、硫嗎福林基、二氫哌喃基、四氫哌喃基、二㗁烷基、吡咯啉基、吡咯啶基、咪唑啉基、咪唑啶基、噻唑啶基、㗁唑啶基、二氧戊環基、二氧雜環戊烯基(dioxolyl)、吡唑啶基、四氫呋喃基、二氫呋喃基、氧呾基(oxetanyl)、氧𠰂基(oxiranyl)、氮呾基(azetidinyl)、氮𠰂基(aziridinyl)、氧氮呾基(oxazetidinyl)、氧氮𠰂基(oxaziridinyl)、氧氮𠰢基(oxazepanyl)、氧氮𠮿基(oxazinanyl)、氮𠰢基(azepanyl)、側氧吡咯啶基、二側氧吡咯啶基、側氧嗎福林基、側氧哌𠯤基和氧𠰢基(oxepanyl)。
特別重要的是雜芳基,即雜芳族系統。根據本發明,術語雜芳基表示雜芳族化合物,即落於上述雜環定義的完全不飽和芳族雜環化合物。較佳者為具有來自上述群組的1至3個(較佳1或2個)相同或不同雜原子之5-至7-員環。本發明的雜芳基為(例如)呋喃基、噻吩基、吡唑基、咪唑基、1,2,3-和1,2,4-三唑基、異㗁唑基、噻唑基、異噻唑基、1,2,3-、1,3,4-、1,2,4-和1,2,5-㗁二唑基、氮呯基、吡咯基、吡啶基、嗒𠯤基、嘧啶基、吡𠯤基、1,3,5-、1,2,4-和1,2,3-三𠯤基、1,2,4-、1,3,2-、1,3,6-和1,2,6-㗁𠯤基、氧呯基、硫呯基、1,2,4-三唑酮基和1,2,4-二氮呯基。本發明的雜芳基亦可經一或多個相同或不同的基團取代。
術語"在各情況下視需要地經取代"意指基團/取代基,諸如烷基、烯基、炔基、烷氧基、烷硫基、烷亞磺醯基、烷磺醯基、環烷基、芳基、苯基、苯甲基、雜環基和雜芳基係經取代,意指(例如)衍生自未經取代的基本結構之經取代的基團,其中取代基為(例如)一(1)個取代基或多個取代基,較佳1、2、3、4、5、6或7個選自由下列所組成之群組:胺基、羥基、鹵素、硝基、氰基、異氰基、巰基、異硫氰基、C
1-C
4-羧基、甲醯胺、SF
5、胺磺醯基、C
1-C
4烷基、C
1-C
4鹵烷基、C
3-C
4環烷基、C
2-C
4烯基、C
5-C
6環烯基、C
2-C
4炔基、N-單-C
1-C
4烷胺基、N,N-二-C
1-C
4烷胺基、N-C
1-C
4烷醯胺基、C
1-C
4烷氧基、C
1-C
4鹵烷氧基、C
2-C
4烯氧基、C
2-C
4炔氧基、C
3-C
4環烷氧基、C
5-C
6環烯氧基、C
1-C
4烷氧羰基、C
2-C
4烯氧羰基、C
2-C
4炔氧羰基、C
6-、C
10-、C
14-芳氧羰基、C
1-C
4烷醯基、C
2-C
4烯羰基、C
2-C
4炔羰基、C
6-、C
10-、C
14-芳羰基、C
1-C
4烷硫基、C
1-C
4鹵烷硫基、C
3-C
4環烷硫基、C
2-C
4烯硫基、C
5-C
6環烯硫基、C
2-C
4炔硫基、C
1-C
4烷亞磺醯基(包括C
1-C
4-烷亞磺醯基之二鏡像異構物)、C
1-C
4鹵烷亞磺醯基(包括C
1-C
4鹵烷亞磺醯基之二鏡像異構物)、C
1-C
4烷磺醯基、C
1-C
4鹵烷磺醯基、N-單-C
1-C
4烷胺磺醯基、N,N-二-C
1-C
4烷胺磺醯基、C
1-C
4烷氧膦基(phosphinyl)、C
1-C
4烷膦醯基(phosphonyl)(包括C
1-C
4烷氧膦基和C
1-C
4烷膦醯基之二鏡像異構物)、N-C
1-C
4烷胺羰基、N,N-二-C
1-C
4烷胺羰基、N-C
1-C
4烷醯胺羰基、N-C
1-C
4烷醯基-N-C
1-C
4烷胺羰基、C
6-、C
10-、C
14-芳基、C
6-、C
10-、C
14-芳氧基、苯甲基、苯甲氧基、苯甲硫基、C
6-、C
10-、C
14-芳硫基、C
6-、C
10-、C
14-芳胺基、苯甲胺基、雜環基和三烷矽基、經由雙鍵鍵結之取代基(諸如C
1-C
4亞烷基(例如亞甲基或亞乙基))、側氧基、亞胺基和經取代的亞胺基。當二或多個基團形成一或多個環時,彼等可為碳環、雜環、飽和、部分飽和、不飽和,例如包括芳族且具有進一步取代。以舉例方式提及的取代基(第一取代基層級),若彼等含有含烴的組分,則其中可視需要地具有進一步經取代(第二取代基層級),例如經一或多個各自獨立地選自鹵素、羥基、胺基、硝基、氰基、異氰基、疊氮基、醯胺基、側氧基和亞胺基之取代基取代。術語"(視需要地)經取代的"基團較佳地僅包括一或二個取代基層級。
本發明的鹵素取代的化學基團或鹵素化基團(例如烷基或烷氧基)係經鹵素單-或多取代至最多取代基之最大可能數目。該等基團也稱為鹵基(諸如,例如,鹵烷基)。在經鹵素多取代的情況下,鹵素原子可為相同或不同,且可全部鍵結至一個碳原子或可鍵結至多個碳原子。鹵素尤其是氟、氯、溴或碘,較佳為氟、氯或溴及更佳為氟。更具體地說,鹵素取代的基團為單鹵環烷基(諸如1-氟環丙基、2-氟環丙基或1-氟環丁基)、單鹵烷基(諸如2-氯乙基、2-氟乙基、1-氯乙基、1-氟乙基、氯甲基、或氟甲基);全鹵烷基(諸如三氯甲基或三氟甲基或CF
2CF
3)、多鹵烷基(諸如二氟甲基、2-氟-2-氯乙基、二氯甲基、1,1,2,2-四氟乙基或2,2,2-三氟乙基)。鹵烷基的其他實例為三氯甲基、氯二氟甲基、二氯氟甲基、氯甲基、溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2,2,2-三氯乙基、2-氯-2,2-二氟乙基、五氟乙基、3,3,3-三氟丙基和五氟-三級丁基。較佳者為具有1至4個碳原子及1至9個(較佳1至5個)選自氟、氯和溴之相同或不同的鹵素原子之鹵烷基。特佳者為具有1或2個碳原子及1至5個選自氟和氯之相同或不同的鹵素原子之鹵烷基,諸如,尤其是二氟甲基、三氟甲基或2,2-二氟乙基。經鹵素取代的化合物之其他實例為鹵烷氧基(諸如OCF
3、OCHF
2、OCH2F、OCF
2CF
3、OCH
2CF
3、OCH
2CHF
2和OCH
2CH
2Cl、鹵烷基硫基(haloalkylsulfanyl)諸如二氟甲硫基、三氟甲硫基、三氯甲硫基、氯二氟甲硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、1,1,2,2-四氟乙硫基、2,2,2-三氟乙硫基或2-氯-1,1,2-三氟乙硫基、鹵烷亞磺醯基諸如二氟甲亞磺醯基、三氟甲亞磺醯基、三氯甲亞磺醯基、氯二氟甲亞磺醯基、1-氟乙亞磺醯基、2-氟乙亞磺醯基、2,2-二氟乙亞磺醯基、1,1,2,2-四氟乙亞磺醯基、2,2,2-三氟乙亞磺醯基和2-氯-1,1,2-三氟乙亞磺醯基、鹵烷亞磺醯基諸如二氟甲亞磺醯基、三氟甲亞磺醯基、三氯甲亞磺醯基、氯二氟甲亞磺醯基、1-氟乙亞磺醯基、2-氟乙亞磺醯基、2,2-二氟乙亞磺醯基、1,1,2,2-四氟乙亞磺醯基、2,2,2-三氟乙亞磺醯基和2-氯-1,1,2-三氟乙亞磺醯基、鹵烷磺醯基諸如二氟甲磺醯基、三氟甲磺醯基、三氯甲磺醯基、氯二氟甲磺醯基、1-氟乙磺醯基、2-氟乙磺醯基、2,2-二氟乙磺醯基、1,1,2,2-四氟乙磺醯基、2,2,2-三氟乙磺醯基和2-氯-1,1,2-三氟乙磺醯基。
在具有碳原子之基團的情況下,較佳者為彼等具有1至4個碳原子之基團,尤其是1或2個碳原子之基團。較佳者一般為來自下列群組之取代基:鹵素(例如氟和氯)、(C
1-C
4)烷基(較佳為甲基或乙基)、(C
1-C
4)鹵烷基(較佳為三氟甲基)、(C
1-C
4)烷氧基(較佳為甲氧基或乙氧基)、(C
1-C
4)鹵烷氧基、硝基和氰基。特佳者在此為取代基甲基、甲氧基、氟和氯。
經取代的胺基諸如經單-或二取代的胺基意指選自經取代的胺基的群組之基團,其係例如經一或二個選自下列群組之相同或不同的基團N-取代:烷基、羥基、胺基、烷氧基、醯基和芳基;較佳地N-單-和N,N-二烷胺基(例如甲胺基、乙胺基、N,N-二甲胺基、N,N-二乙胺基、N,N-二-正丙胺基、N,N-二異丙胺基或N,N-二丁胺基)、N-單-或N,N-二烷氧基烷胺基(例如N-甲氧基甲胺基、N-甲氧基乙胺基、N,N-二(甲氧基甲基)胺基或N,N-二(甲氧基乙基)胺基)、N-單-和N,N-二芳胺基,諸如視需要地經取代的苯胺、醯胺基、N,N-二醯胺基、N-烷基-N-芳胺基、N-烷基-N-醯胺基以及飽和N-雜環;較佳者在此為具有1至4個碳原子的烷基;在此,芳基較佳為苯基或經取代的苯基;關於醯基,定義進一步給予於下,較佳為(C
1-C
4)烷醯基。該等適用於經取代的羥胺基或肼基。
經取代的胺基亦包括在氮原子上具有四個有機取代基之四級銨化合物(鹽)。
視需要地經取代的苯基較佳為未經取代或經來自下列群組之相同或不同基團單-或多取代,較佳為最多三取代的苯基:鹵素、(C
1-C
4)烷基、(C
1-C
4)烷氧基、(C
1-C
4)烷氧基-(C
1-C
4)烷氧基、(C
1-C
4)烷氧基-(C
1-C
4)烷基、(C
1-C
4)鹵烷基、(C
1-C
4)鹵烷氧基、(C
1-C
4)烷硫基、(C
1-C
4)鹵烷硫基、(C
1-C
4)烷亞磺醯基、(C
1-C
4) 鹵烷亞磺醯基、(C
1-C
4)烷磺醯基 (C
1-C
4)鹵烷磺醯基、氰基、異氰基和硝基,例如鄰-、間-和對-甲苯基、二甲基苯基、2-、3-和4-氯苯基、2-、3-和4-氟苯基、2-、3-和4-三氟甲基-和-三氯甲基苯基、2,4-、3,5-、2,5-和2,3-二氯苯基、鄰-、間-和對-甲氧基苯基、4-七氟苯基。
視需要地經取代的環烷基較佳為未經取代或經來自下列群組之相同或不同基團單-或多取代,較佳為最多三取代的環烷基:鹵素、氰基、(C
1-C
4)烷基、(C
1-C
4)烷氧基、(C
1-C
4)烷氧基-(C
1-C
4)烷氧基、(C
1-C
4)烷氧基-(C
1-C
4)烷基、(C
1-C
4)鹵烷基和(C
1-C
4)鹵烷氧基,尤其是經一或二個(C
1-C
4)烷基取代。
本發明的化合物可出現於較佳實施態樣中。本文所述的各個實施態樣可彼此組合。不包括違反自然法則且熟習該項技術者根據其專業知識可以因此排除之組合。例如,排除具有3或多個相鄰的氧原子之環結構。
異構物
取決於取代基的性質,式(I)化合物可於幾何及/或光學活性異構物或不同組成之對應異構物混合物的形式。此等立體異構物為例如鏡像異構物、非鏡像異構物、阻轉異構物(atropisomers)或幾何異構物。因此,本發明包含純立體異構物及此等異構物的任何混合物。
方法及用途
本發明亦關於控制動物害蟲之方法,其中使式(I)化合物作用於動物害蟲及/或彼等的棲息地。動物害蟲的控制較佳地在農業和森林中,及在原料保護中進行。較佳地從中排除用於人類或動物體的手術或治療處理之方法及在人類或動物體上進行之診斷方法。
本發明此外關於式(I)化合物作為殺蟲劑(特別是作物保護劑)之用途。
在本申請案的情況下,術語"殺蟲劑"在各情況下亦總是包含術語"作物保護劑"。
具有良好的植物耐受性、有利的溫血動物毒性及良好的環境相容性(compatibility)的式(I)化合物適合於保護植物及植物組織對抗生物或非生物脅迫因子、適合於增加收成產率、適合於改良收成材料的品質和適合於控制農業、園藝、畜牧業、水產培養、森林、花園和休閒設施、庫存產品與材料的保護、及衛生領域中所遇到的動物害蟲,尤其是昆蟲、蛛形綱動物、蠕蟲,特別是線蟲和軟體動物。
在本專利申請案的情況內,術語“衛生”係理解為意指目的是預防疾病,特別為傳染性疾病,且用以保護人類及動物健康及/或保護環境及/或維持清潔的任何及所有措施、程序及實施。根據本發明,這尤其包括用於例如紡織品或硬質表面(尤其是玻璃、木材、混凝土、瓷器、陶瓷、塑料或亦為金屬的表面)之清潔、消毒及滅菌,且確保該等保持無衛生害蟲及/或彼等排泄物的措施。關於此點較佳地自本發明範圍排除的是可應用於人體或動物體的手術或治療處理程序及在人體或動物體上進行之診斷程序。
術語“衛生防區”因此涵蓋其中該等衛生措施、程序及實施具有重要性的所有領域、技術領域和工業應用,例如關於在廚房、麵包房、機場、浴池、游泳池、商場、飯店、醫院、馬厩、畜牧業等等中的衛生。
術語“衛生害蟲”因此係理解為意指一或多種存在於衛生防區是有問題的動物害蟲,特別是出於健康的理由。因此主要目的為衛生害蟲存在於衛生防區及/或與其接觸之避免或減至最少。此特別可透過施用可用以預防感染及對付已存在的感染二者之殺蟲劑而達成。亦可使用避免或減少與害蟲接觸之製劑。衛生害蟲包括例如下述之有機體。
術語“衛生保護”因此涵蓋維持及/或改善此等衛生措施、程序及實施的所有行動。
式(I)化合物較佳地可用作為殺蟲劑。彼等具有對抗一般敏感及抗性物種且對抗所有或一些發育期之活性。上述害蟲包括:
來自節肢動物門(Arthropoda)之害蟲,特別是來自蜘蛛綱(Arachnida)例如粉蟎屬(Acarus spp.)(例如粗腳粉蟎(Acarus siro)、枸杞瘤節蜱(Aceria kuko)、柑橘瘤癭蟎(Aceria sheldoni))、剌皮節蜱屬(Aculops spp.)、刺節蜱屬(Aculus spp.)(例如福氏刺節蜱(Aculus fockeui)、蘋果刺節蜱(Aculus schlechtendali))、大壁蝨屬(Amblyomma spp.)、橫紋葉蟎(Amphitetranychus viennensis)、銳緣壁蝨屬(Argas spp.)、牛蜱屬(Boophilus spp.)、短須蟎屬(Brevipalpus spp.)(例如紫紅短須蟎(Brevipalpus phoenicis))、麥苔蟎(Bryobia graminum)、苜蓿苔蟎(Bryobia praetiosa)、刺尾蠍屬(Centruroides spp.)、足蟎屬(Chorioptes spp.)、雞蟎(Dermanyssus gallinae)、歐洲室塵蟎(Dermatophagoides pteronyssinus)、美洲塵蟎(Dermatophagoides farinae)、革蜱屬(Dermacentor spp.)、始葉蟎屬(Eotetranychus spp.)(例如核桃始葉蟎(Eotetranychus hicoriae))、梨上節蜱(Epitrimerus pyri)、真葉蟎屬(Eutetranychus spp.)(例如班氏真葉蟎(Eutetranychus banksi))、節蜱屬(Eriophyes spp.)(例如梨節蜱(Eriophyes pyri))、家食甜蟎(Glycyphagus domesticus)、紅足海鐮螯蟎(Halotydeus destructor)、半跗線蟎屬(Hemitarsonemus spp.)(例如茶半跗線蟎(Hemitarsonemus latus)(= 多食細蟎(Polyphagotarsonemus latus))、長鬚壁蝨屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、寡婦蜘蛛屬(Latrodectus spp.)、棕蜘蛛屬(Loxosceles spp.)、歐洲秋收恙蟎(Neutrombicula autumnalis)、Nuphersa屬、赤葉蟎屬(Oligonychus spp.)(例如茶紅葉蟎(Oligonychus coffeae)、柏木赤葉蟎(Oligonychus coniferarum)、冬青赤葉蟎(Oligonychus ilicis)、甘蔗赤葉蟎(Oligonychus indicus)、芒果赤葉蟎(Oligonychus mangiferus)、草地赤葉蟎(Oligonychus pratensis)、石榴赤葉蟎(Oligonychus punicae)、樟赤葉蟎(Oligonychus yothersi))、鈍緣蜱屬(Ornithodorus spp.)、禽刺蟎屬(Ornithonyssus spp.)、葉蟎屬(Panonychus spp.)(例如柑橘葉蟎(Panonychus citri)(=柑橘全爪蟎(Metatetranychus citri)、歐洲葉蟎(Panonychus ulmi)(=Metatetranychus ulmi)、柑橘銹蟎(Phyllocoptruta oleivora)、多趾寬葉蟎(Platytetranychus multidigituli)、多食細蟎(Polyphagotarsonemus latus)、痂恙蟲屬(Psoroptes spp.)、扇頭壁蝨屬(Rhipicephalus spp.)、根蟎屬(Rhizoglyphus spp.)、疥癬蟲屬(Sarcoptes spp.)、中東金蠍(Scorpio maurus)、細蟎屬(Steneotarsonemus spp.)、稻細蟎(Steneotarsonemus spinki)、跗線蟎屬(Tarsonemus spp.)(例如亂跗線蟎(Tarsonemus confuses)、白跗線蟎(Tarsonemus pallidus))、葉蟎屬(Tetranychus spp.)(例如加拿大葉蟎(Tetranychus canadensis)、朱砂葉蟎(Tetranychus cinnabarinus)、土耳其斯坦葉蟎(Tetranychus turkestani)、二點葉蟎(Tetranychus urticae))、阿氏真恙蟎(Trombicula alfreddugesi)、蠍屬(Vaejovis spp.)、斜背瘤節蜱(Vasates lycopersici);
來自唇足綱(Chilopoda)之綱,例如地蜈蚣屬(Geophilus spp.)、蚰蜒屬(Scutigera spp.);
來自黏管目(Collembola)之目或綱,例如棘跳蟲(Onychiurus armatus);綠圓跳蟲(Sminthurus viridis);
來自倍足綱(Diplopoda)之綱,例如具斑馬陸(Blaniulus guttulatus);
來自昆蟲綱(Insecta)之綱,例如來自蜚蠊目(Blattodea)之目,例如東方蜚蠊(Blatta orientalis)、亞洲蜚蠊(Blattella asahinai)、德國蜚蠊(Blattella germanica)、馬德拉蜚蠊(Leucophaea maderae)、歐洲缺翅姬蜚蠊(Loboptera decipiens)、家屋斑蠊(Neostylopyga rhombifolia)、角腹蠊屬(Panchlora spp.)、稀蠊屬(Parcoblatta spp.)、家蠊屬(Periplaneta spp.)(例如美洲家蠊(Periplaneta americana)、澳洲家蠊(Periplaneta australasiae))、蘇利南潛蠊(Pycnoseelus surinamensis)、棕帶姬蠊(Supella longipalpa);
來自鞘翅目(Coleoptera)之目,例如條紋葉甲(Acalymma vittatum)、菜豆象(Acanthoscelides obtectus)、褐金龜屬(Adoretus spp.)、小蜂窩甲蟲(Aethina tumida)、赤楊紫跳甲(Agelastica alni)、瘦吉丁蟲屬(Agrilus spp.)(例如光蠟瘦吉丁蟲(Agrilus planipennis)、吉丁蟲(Agrilus coxalis)、線紋瘦吉丁蟲(Agrilus bilineatus)、青銅樺吉丁蟲(Agrilus anxius))、叩甲屬(Agriotes spp.)(例如直條叩甲(Agriotes linneatus)、小麥叩甲(Agriotes mancus)、外米擬步行蟲(Alphitobius diaperinus)、六月金龜子(Amphimallon solstitialis)、家具竊蠹(Anobium punctatum)、星天牛屬(Anoplophora spp.)(例如光肩星天牛(Anoplophora glabripennis))、花象屬(Anthonomus spp.)(例如棉鈴象甲(Anthonomus grandis))、圓皮囊屬(Anthrenus spp.)、梨象屬(Apion spp.)、甘蔗金龜屬(Apogonia spp.)、隱食甲屬(Atomaria spp.)(例如甜菜隱食甲(Atomaria linearis))、毛皮囊屬(Attagenus spp.)、天藍巴利斯(Baris caerulescens)、惡條豆象(Bruchidius obtectus)、豆象屬(Bruchus spp.)(例如豌豆象(Bruchus pisorum)、蠶豆象(Bruchus rufimanus))、龜金花蟲屬(Cassida spp.)、菜豆螢葉甲(Cerotoma trifurcata)、象甲屬(Ceutorrhynchus spp.)(例如甘藍莢象甲(Ceutorrhynchus assimilis)、油菜莖象甲(Ceutorrhynchus quadridens)、蕪菁象甲(Ceutorrhynchus rapae))、凹脛跳甲屬(Chaetocnema spp.)(例如甘薯凹脛跳甲(Chaetocnema confinis)、玉米葉凹脛跳甲(Chaetocnema denticulata)、荒地玉米跳甲(Chaetocnema ectypa))、門第庫斯方喙象(Cleonus mendicus)、寬胸金針蟲屬(Conoderus spp.)、根頸象屬(Cosmopolites spp.)(例如香蕉根頸象(Cosmopolites sordidus))、紐西蘭草金龜(Costelytra zealandica)、叩甲屬(Ctenicera spp.)、象鼻蟲屬(Curculio spp.)(例如美核桃象鼻蟲(Curculio caryae))、大栗象鼻蟲(Curculio caryatrypes)、栗鈍象鼻蟲(Curculio obtusus)、小栗象鼻蟲(Curculio sayi)、鏽赤扁穀盜(Cryptolestes ferrugineus)、長角扁穀盜(Cryptolestes pusillus)、楊幹隱喙象(Cryptorhynchus lapathi)、芒果隱喙象(Cryptorhynchus mangiferae)、細枝象屬(Cylindrocopturus spp.)、密點細枝象(Cylindrocopturus adspersus)、洋松細枝象(Cylindrocopturus furnissi)、大小蠹屬(Dendroctonus spp.)(例如山松甲蟲(Dendroctonus ponderosae))、皮囊屬(Dermestes spp.)、葉甲屬(Diabrotica spp.)(例如黃瓜條葉甲(Diabrotica balteata)、玉米根葉甲(Diabrotica barberi)、十一星葉甲食根亞種(Diabrotica undecimpunctata howardi)、十一星瓜葉甲幼蟲(Diabrotica undecimpunctata undecimpunctata)、玉米根螢葉甲(Diabrotica virgifera virgifera)、墨西哥玉米根葉甲(Diabrotica virgifera zeae)、蛀野螟屬(Dichocrocis spp.)、稻鐵甲蟲(Dicladispa armigera)、兜蟲屬(Diloboderus spp.)、象甲屬(Epicaerus spp.)、食植瓢蟲屬(Epilachna spp.)(例如南瓜食植瓢蟲(Epilachna borealis)、墨西哥豆食植瓢蟲(Epilachna varivestis))、毛跳甲屬(Epitrix spp.)(例如黃瓜毛跳甲(Epitrix cucumeris)、茄毛跳甲(Epitrix fuscula)、煙草毛跳甲(Epitrix hirtipennis)、美國馬鈴薯毛跳甲(Epitrix subcrinita)、塊莖毛跳甲(Epitrix tuberis))、鑽孔蟲屬(Faustinus spp.)、裸蛛甲(Gibbium psylloides)、闊角穀盜(Gnathocerus cornutus)、菜心野螟(Hellula undalis)、黑異爪蔗金龜(Heteronychus arator)、寡節鰓金龜屬(Heteronyx spp.)、優雅海拉莫法(Hylamorpha elegans)、家天牛(Hylotrupes bajulus)、苜蓿葉象甲(Hypera postica)、金象甲(Hypomeces squamosus)、咪小蠹屬(Hypothenemus spp.)(例如咖啡果咪小蠹(Hypothenemus hampei)、蘋枝褐咪小蠹(Hypothenemus obscurus)、柔毛咪小蠹(Hypothenemus pubescens))、甘蔗大褐齒爪鰓金龜(Lachnosterna consanguinea)、鋸角毛食骸甲(Lasioderma serricorne)、長首穀盜(Latheticus oryzae)、薪甲屬(Lathridius spp.)、細頸金花蟲屬(Lema spp.)、科羅拉多金花蟲(Leptinotarsa decemlineata)、銀潛蛾屬(Leucoptera spp.)(例如咖啡銀潛蛾(Leucoptera coffeella))、Limonius ectypus、水稻水象鼻蟲(Lissorhoptrus oryzophilus)、蔔象屬(Listronotus)(=象甲屬(Hyperodes spp.))、筒喙象屬(Lixus spp.)、螢葉甲屬(Luperodes spp.)、黃胸寡毛跳甲(Luperomorpha xanthodera)、粉蠹屬(Lyctus spp.)、縊虎天牛屬(Megacyllene spp.)(例如刺槐天牛(Megacyllene robiniae))、美洲葉甲屬(Megascelis spp.)、梳爪叩甲屬(Melanotus spp.)(例如Melanotus longulus oregonensis)、花粉甲(Meligethes aeneus)、鰓金龜屬(Melolontha spp.)(例如大栗鳃角金龟(Melolontha melolontha))、Migdolus屬、長角天牛屬(Monochamus spp.)、南美果樹象甲(Naupactus xanthographus)、郭公蟲屬(Necrobia spp.)、Neogalerucella屬、金黃蛛甲(Niptus hololeucus)、椰子犀角金龜(Oryctes rhinoceros)、鋸胸粉扁蟲(Oryzaephilus surinamensis)、Oryzaphagus oryzae、耳喙象屬(Otiorrhynchus spp.)(例如蘋果耳喙象(Otiorhynchus cribricollis)、苜蓿耳喙象(Otiorhynchus ligustici)、草莓耳喙象(Otiorhynchus ovatus)、草莓根耳喙象(Otiorhynchus rugosostriarus)、葡萄黑耳喙象(Otiorhynchus sulcatus))、負泥蟲屬(Oulema spp.)(例如黑角負泥蟲(Oulema melanopus)、稻負泥蟲(Oulema oryzae)、小青花金龜(Oxycetonia jucunda)、辣根猿葉甲(Phaedon cochleariae)、鰓角金龜屬(Phyllophaga spp.)、劍鰓角金龜(Phyllophaga helleri)、葉蚤屬(Phyllotreta spp.)(例如辣根葉蚤(Phyllotreta armoraciae)、油菜籽葉蚤(Phyllotreta pusilla)、西部葉蚤(Phyllotreta ramosa)、黃條葉蚤(Phyllotreta striolata))、日本金龜子(Popillia japonica)、安第斯馬鈴薯象屬(Premnotrypes spp.)、大谷蠹(Prostephanus truncatus)、蚤甲蟲屬(Psylliodes spp.)(例如馬鈴薯跳甲(Psylliodes affinis)、油菜金頭跳甲(Psylliodes chrysocephala)、忽布跳甲(Psylliodes punctulata))、蜘甲屬(Ptinus spp.)、暗色瓢蟲(Rhizobius ventralis)、榖蠹(Rhizopertha dominica)、棕櫚象屬(Rhynchophorus spp.)、紅棕象甲(Rhynchophorus ferrugineus)、棕櫚象甲(Rhynchophorus palmarum)、小蠹屬(Scolytus spp.)(例如歐洲榆小蠹(Scolytus multistriatus))、六齒長蠹蟲(Sinoxylon perforans)、米象屬(Sitophilus spp.)(例如榖象蟲(Sitophilus granarius)、羅望子象(Sitophilus linearis)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais))、尖隱味象屬(Sphenophorus spp.)、藥材甲(Stegobium paniceum)、莖象屬(Sternechus spp.)(例如豆莖象(Sternechus paludatus))、扁肩象屬(Symphyletes spp.)、纖毛象屬(Tanymecus spp.)(例如玉米纖毛象(Tanymecus dilaticollis)、印度纖毛象(Tanymecus indicus)、甜菜灰色象蟲(Tanymecus palliatus)、大黃粉蟲(Tenebrio molitor)、大穀盜(Tenebrioides mauretanicus)、擬穀盜屬(Tribolium spp.)(例如美洲黑擬穀盜(Tribolium audax)、擬穀盜(Tribolium castaneum)、扁擬榖盜(Tribolium confusum)、斑皮蠹屬(Trogoderma spp.)、籽象屬(Tychius spp.)、脊虎天牛屬(Xylotrechus spp.)、距步甲屬(Zabrus spp.),例如玉米距步甲(Zabrus tenebrioides);
來自革翅目(Dermaptera)之目,例如海肥螋(Anisolabis maritime)、歐洲秋螋(Forficula auricularia)、溪岸蠼螋(Labidura riparia);
來自雙翅目(Diptera)之目,例如斑蚊屬(Aedes spp.)(例如埃及斑蚊(Aedes aegypti))、白線斑蚊(Aedes albopictus)、叮刺斑蚊(Aedes sticticus)、白肋斑蚊(Aedes vexans),潛蠅屬(Agromyza spp.)(例如苜蓿斑潛蠅(Agromyza frontella)、玉米斑潛蠅(Agromyza parvicornis))、果實蠅屬(Anastrepha spp.)、瘧蚊屬(Anopheles spp.)(例如四斑瘧蚊(Anopheles quadrimaculatus)、岡比亞瘧蚊(Anopheles gambiae)),瘿蚊屬(Asphondylia spp.)、寡毛實蠅屬(Bactrocera spp.)(例如瓜實蠅(Bactrocera cucurbitae)、東方果實蠅(Bactrocera dorsalis)、橄欖實蠅(Bactrocera oleae)),花園毛蚊(Bibio hortulanus)、琉璃蠅(Calliphora erythrocephala)、紅頭麗蠅(Calliphora vicina)、地中海果實蠅(Ceratitis capitata)、搖蚊屬(Chironomus spp.)、金蠅屬(Chrysomya spp.)、斑虻屬(Chrysops spp.)、高額麻虻(Chrysozona pluvialis)、螺旋蠅屬(Cochliomya spp.)、癭蚊屬(Contarinia spp.)(例如葡萄癭蚊(Contarinia johnsoni)、甘藍癭蚊(Contarinia nasturtii)、梨癭蚊(Contarinia pyrivora)、向日葵癭蚊(Contarinia schulzi)、高粱癭蚊(Contarinia sorghicola)、麥黃吸漿蟲(Contarinia tritici))、人皮蠅(Cordylobia anthropophaga)、稻環搖蚊(Cricotopus sylvestris)、家蚊屬(Culex spp.)(例如地下家蚊(Culex pipiens)、熱帶家蚊(Culex quinquefasciatus))、庫蠓屬(Culicoides spp.)、絨蚊屬(Culiseta spp.)、野生齧齒蠅屬(Cuterebra spp.)、橄欖蠅(Dacus oleae)、葉癭蚊屬(Dasineura spp.)(例如油菜莢葉癭蚊(Dasineura brassicae))、地種蠅屬(Delia spp.)(例如蔥地種蠅(Delia antiqua)、麥地種蠅(Delia coarctata)、毛跗地種蠅(Delia florilega)、灰地種蠅(Delia platura)、甘藍地種蠅(Delia radicum))、人膚蠅(Dermatobia hominis)、果蠅屬(Drosophila spp.)(例如黑腹果蠅(Drosophila melanogaster)、斑翅果蠅(Drosophila suzukii))、稻象屬(Echinocnemus spp.)、芹菜尤列實蠅(Euleia heraclei)、廁蠅屬(Fannia spp.)、馬蠅屬(Gasterophilus spp.)、舌蠅屬(Glossina spp.)、麻虻屬(Haematopota spp.)、毛眼水蠅屬(Hydrellia spp.)、小灰毛眼水蠅(Hydrellia griseola)、種蠅屬(Hylemya spp.)、蝨蠅屬(Hippobosca spp.)、牛蠅屬(Hypoderma spp.)、斑潛蠅屬(Liriomyza spp.)(例如菜斑潛蠅(Liriomyza brassicae)、南美斑潛蠅(Liriomyza huidobrensis)、蔬菜斑潛蠅(Liriomyza sativae))、綠蠅屬(Lucilia spp.)(例如銅綠蠅(Lucilia cuprina))、羅蛉屬(Lutzomyia spp.)、孟松蚊屬(Mansonia spp.)、家蠅屬(Musca spp.)(例如家蠅(Musca domestica)、舍蠅(Musca domestica vicina))、狂蠅屬(Oestrus spp.)、黑麥稈蠅(Oscinella frit)、擬長跗搖蚊屬(Paratanytarsus spp.)、Paralauterborniella sucincta、花蠅屬(Pegomya)或泉蠅屬(Pegomyia spp.)(例如甜菜泉蠅(Pegomya betae)、甜菜潛葉蠅(Pegomya hyoscyami)、懸鉤子泉蠅(Pegomya rubivora))、白蛉屬(Phlebotomus spp.)、草種蠅屬(Phorbia spp.)、玻璃蠅屬(Phormia spp.)、鎧氏酪蠅(Piophila casei)、蘆筍實蠅(Platyparea poeciloptera)、Prodiplosis屬、胡蘿蔔莖蠅(Psila rosae)、繞實蠅屬(Rhagoletis spp.)(例如櫻桃繞實蠅(Rhagoletis cingulata)、核桃繞實蠅(Rhagoletis completa)、黑櫻桃繞實蠅(Rhagoletis fausta)、西部櫻桃繞實蠅(Rhagoletis indifferens)、越桔繞實蠅(Rhagoletis mendax)、蘋果繞實蠅(Rhagoletis pomonella))、肉蠅屬(Sarcophaga spp.)、蚋屬(Simulium spp.)(例如南方蚋(Simulium meridionale))、廄蠅屬(Stomoxys spp.)、牛虻屬(Tabanus spp.)、根斑蠅屬(Tetanops spp.)、大蚊屬(Tipula spp.)(例如歐洲大蚊(Tipula paludosa)、牧場大蚊(Tipula simplex)、番木瓜長尾實蠅(Toxotrypana curvicauda);
來自半翅目(Hemiptera)之目,例如Acizzia acaciaebaileyanae、Acizzia dodonaeae、Acizzia uncatoides、Acrida turrita、無網長管蟲牙屬(Acyrthosipon spp.)(例如豌豆蟲牙(Acyrthosiphon pisum))、Acrogonia屬、Aeneolamia屬、隆脉木蝨屬(Agonoscena spp.)、刺粉蝨屬(Aleurocanthus spp.)、歐洲甘藍粉蝨(Aleyrodes proletella)、甘蔗穴粉蝨(Aleurolobus barodensis)、棉絮粉蝨(Aleurothrixus floccosus)、榴蓮木蝨(Allocaridara malayensis)、小綠葉蟬屬(Amrasca spp.),例如小綠葉蟬(Amrasca bigutulla)、小葉蟬(Amrasca devastans)、李薊圓尾蚜(Anuraphis cardui)、圓蚧屬(Aonidiella spp.)(例如橘紅腎圓盾介殼蟲(Aonidiella aurantii)、橘黃腎圓盾介殼蟲(Aonidiella citrina)、木瓜腎圓盾介殼蟲(Aonidiella inornata)、梨瘤蚜(Aphanostigma piri))、蚜蟲屬(Aphis spp.)(例如橘卷菜蚜(Aphis citricola)、豆蚜(Aphis craccivora)、蠶豆蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphis glycines)、綿蚜(Aphis gossypii)、常春藤蚜(Aphis hederae)、葡萄蔓蚜(Aphis illinoisensis)、飛蓬根蚜(Aphis middletoni)、鼠李馬鈴薯蚜(Aphis nasturtii)、夾竹桃蚜(Aphis nerii)、蘋果蚜(Aphis pomi)、芹菜蚜(Aphis spiraecola)、莢迷蚜(Aphis viburniphila)、葡萄葉蟬(Arboridia apicalis)、Arytainilla屬、小圓盾介殼蟲屬(Aspidiella spp.)、盾介殼蟲屬(Aspidiotus spp.)(例如夾竹桃圓蚧(Aspidiotus nerii))、Atanus屬、馬鈴薯蚜(Aulacorthum solani)、煙草粉蝨(Bemisia tabaci)、Blastopsylla occidentalis、白千層木蝨(Boreioglycaspis melaleucae)、光管舌尾蚜(Brachycaudus helichrysii)、微管蚜屬(Brachycolus spp.)、甘藍蚜(Brevicoryne brassicae)、嘻木蝨屬(Cacopsylla spp.)(例如黃木蝨(Cacopsylla pyricola))、小褐稻蝨(Calligypona marginata)、Capulinia屬、紅頭大葉蟬(Carneocephala fulgida)、甘蔗綿蚜(Ceratovacuna lanigera)、沬蟬科(Cercopidae)、蠟蚧屬(Ceroplastes spp.)、草莓釘蚜(Chaetosiphon fragaefolii)、蔗黃雪盾蚧(Chionaspis tegalensis)、茶綠葉蟬(Chlorita onukii)、棉蝗(Chondracris rosea)、核桃黑斑蚜(Chromaphis juglandicola)、褐圓盾介殼蟲屬(Chrysomphalus aonidum)、褐圓介殼蟲(Chrysomphalus ficus)、玉米葉蟬(Cicadulina mbila)、Coccomytilus halli、介殼蟲屬(Coccus spp.)(例如扁堅介殼蟲(Coccus hesperidum)、長堅介殼蟲(Coccus longulus)、橘軟蠟蚧(Coccus pseudomagnoliarum)、黃綠介殼蟲(Coccus viridis))、黑茶藨隱瘤額蚜(Cryptomyzus ribis)、黃木蝨屬(Cryptoneossa spp.)、木蝨屬(Ctenarytaina spp.)、葉蟬屬(Dalbulus spp.)、Dialeurodes chittendeni、柑桔裸粉蝨(Dialeurodes citri)、柑橘木蝨(Diaphorina citri)、白背盾蚧屬(Diaspis spp.)、麥蚜屬(Diuraphis spp.)、棉蚜屬(Doralis spp.)、草履介殼蟲屬(Drosicha spp.)、圓尾蚜屬(Dysaphis spp.)(例如銹條蚜(Dysaphis apiifolia)、玫瑰蘋果蚜(Dysaphis plantaginea)、百合西圓尾蚜(Dysaphis tulipae)、嫡粉介殼蟲屬(Dysmicoccus spp.)、小綠葉蟬屬(Empoasca spp.)(例如西部馬鈴薯微葉蟬(Empoasca abrupta)、馬鈴薯小綠葉蟬(Empoasca fabae)、蘋果小綠葉蟬(Empoasca maligna)、索拉納小綠葉蝶(Empoasca solana)、Empoasca stevensi、蘋果棉蚜屬(Eriosoma spp.)(例如美洲榆綿蚜(Eriosoma americanum)、蘋果綿蚜(Eriosoma lanigerum)、梨根綿蚜(Eriosoma pyricola)、斑葉蟬屬(Erythroneura spp.)、Eucalyptolyma屬、褐木蝨屬(Euphyllura spp.)、雙葉殃葉蟬(Euscelis bilobatus)、粉絲介殼蟲屬(Ferrisia spp.)、單銳盾蟲屬(Fiorinia spp.)、角盾蚧(Furcaspis oceanica)、咖啡荒粉蚧(Geococcus coffeae)、盾木蝨屬(Glycaspis spp.)、銀合歡木蝨(Heteropsylla cubana)、頰木蝨(Heteropsylla spinulosa)、褐透翅尖頭大葉蟬(Homalodisca coagulata)、桃大尾蚜(Hyalopterus arundinis)、桃粉蚜(Hyalopterus pruni)、吹棉介殼蟲屬(Icerya spp.)(例如吹綿介殼蟲(Icerya purchasi))、片角葉蟬屬(Idiocerus spp.)、扁喙葉蟬屬(Idioscopus spp.)、斑飛蝨(Laodelphax striatellus)、蠟蚧屬(Lecanium spp.)(例如歐洲水果介殼蟲(Lecanium corni(=扁平球堅介殼蟲(Parthenolecanium corni)))、頓盾階屬(Lepidosaphes spp.)(例如榆蠣盾蚧(Lepidosaphes ulmi)、偽菜蚜(Lipaphis erysimi)、日本長片盾介殼蟲(Lopholeucaspis japonica)、斑衣蠟蟬(Lycorma delicatula)、長管蚜屬(Macrosiphum spp.)(例如馬鈴薯網管蚜(Macrosiphum euphorbiae))、紫斑長管蚜(Macrosiphum lilii)、薔薇長管蚜(Macrosiphum rosae)、二點葉蜂(Macrosteles facifrons)、沫蝶屬(Mahanarva spp.)、高粱蚜(Melanaphis sacchari)、角蟬屬(Metcalfiella spp.)、蛾錯蜂(Metcalfa pruinosa)、麥無網長管蚜(Metopolophium dirhodum)、黑緣平翅斑蚜(Monellia costalis)、Monelliopsis pecanis、瘤蚜屬(Myzus spp.)(例如冬蔥瘤額蚜(Myzus ascalonicus)、黑櫻桃蚜(Myzus cerasi)、女貞瘤額蚜(Myzus ligustri)、堇菜瘤蚜(Myzus ornatus)、桃蚜(Myzus persicae)、煙草蚜蟲(Myzus nicotianae))、萵苣蚜(Nasonovia ribisnigri)、黑尾葉蟬屬(Nephotettix spp.)(例如黑尾葉蟬(Nephotettix cincticeps)、黑條黑尾葉蟬(Nephotettix nigropictus)、Nettigoniclla spectra)、褐飛蝨(Nilaparvata lugens)、Oncometopia屬、狌蚧(Orthezia praelonga)、中華稻蝗(Oxya chinensis)、芽瘦木蝨屬(Pachypsylla spp.)、粉蝨(Parabemisia myricae)、木蝨屬(Paratrioza spp.)(例如番茄蝨(Paratrioza cockerelli))、黑星蚧屬(Parlatoria spp.)、癭棉蚜屬(Pemphigus spp.),例如囊柄癭綿蚜(Pemphigus bursarius)、甜菜多脈癭綿蚜(Pemphigus populivenae)、玉米飛蝨(Peregrinus maidis)、扁角飛蝨屬 (Perkinsiella spp.)、綿粉介殼蟲屬(Phenacoccus spp.)(例如美地綿粉介殼蟲(Phenacoccus madeirensis))、楊平翅棉蚜(Phloeomyzus passerinii)、蛇麻草蚜(Phorodon humuli)、根瘤蚜屬(Phylloxera spp.)(例如美核桃根瘤蚜(Phylloxera devastatrix)、薄殼山核桃瘤蚜(Phylloxera notabilis))、柑桔並盾介殼蟲(Pinnaspis aspidistrae)、粉介殼蟲屬(Planococcus spp.)(例如柑桔粉介殼蟲(Planococcus citri)、Prosopidopsylla flava、厚綠原綿介殼蟲(Protopulvinaria pyriformis)、桑介殼蟲(Pseudaulacaspis pentagona))、禾草粉蚧屬(Pseudococcus spp.)(例如柑桔栖粉介殼蟲(Pseudococcus calceolariae)、康氏粉介殼蟲(Pseudococcus comstocki)、長尾粉介殼蟲(Pseudococcus longispinus)、海粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni))、Psyllopsis屬、木蝨屬(Psylla spp.)(例如黃楊木蝨(Psylla buxi)、蘋木蝨(Psylla mali)、梨木蝨(Psylla pyri))、金小蜂屬(Pteromalus spp.)、棉蚧屬(Pulvinaria spp.)、短足蠟蟬屬(Pyrilla spp.)、圓蚧屬(Quadraspidiotus spp.)(例如胡桃圓盾蚧(Quadraspidiotus juglansregiae)、歐洲果圓蚧(Quadraspidiotus ostreaeformis)、梨齒盾介殼蟲(Quadraspidiotus perniciosus)、Quesada gigas、平粉介殼蟲屬(Rastrococcus spp.)、縊管蚜屬(Rhopalosiphum spp.)(例如玉米蚜(Rhopalosiphum maidis)、蘋草縊管蚜(Rhopalosiphum oxyacanthae)、稻麥蚜(Rhopalosiphum padi)、紅腹縊管蚜(Rhopalosiphum rufiabdominale))、硬介殼蟲屬(Saissetia spp.)(例如咖啡硬介殼蟲(Saissetia coffeae)、糖梳硬介殼蟲(Saissetia miranda)、黑光硬介殼蟲(Saissetia neglecta)、工脊硬介殼蟲(Saissetia oleae)、葡萄帶葉蟬(Scaphoideus titanus)、綠蚜(Schizaphis graminum)、刺圓盾介殼蟲(Selenaspidus articulatus)、牛鞭草蚜(Sipha flava)、麥長管蚜(Sitobion avenae)、白背飛蝨屬(Sogata spp.)、背飛蝨(Sogatella furcifera)、飛蝨屬(Sogatodes spp.)、沫蟬(Stictocephala festina)、梣粉蝨(Siphoninus phillyreae)、Tenalaphara malayensis、Tetragonocephela屬、胡桃黑蚜(Tinocallis caryaefoliae)、廣胸沫蜂屬(Tomaspis spp.)、聲蟲蚜屬(Toxoptera spp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus)、溫室粉蝨(Trialeurodes vaporariorum)、木蝨屬(Trioza spp.)(例如柿木蝨(Trioza diospyri))、小葉蟬屬(Typhlocyba spp.)、尖盾蚧屬(Unaspis spp.)、葡萄根瘤蚜(Viteus vitifolii)、斑葉蜂屬(Zygina spp.);
來自異翅亞目(Heteroptera)之亞目,例如蝽象屬(Aelia spp.)、南瓜緣蝽(Anasa tristis)、擬麗蜂屬(Antestiopsis spp.)、紅緣蝽屬(Boisea spp.)、土長蝽屬(Blissus spp.)、俊盲蜂屬(Calocoris spp.)、盲蝽(Campylomma livida)、異背長蝽屬(Cavelerius spp.)、臭蟲屬(Cimex spp.)(例如阿氏臭蟲(Cimex adjunctus)、熱帶臭蟲(Cimex hemipterus)、溫帶臭蟲(Cimex lectularius)、蝠臭蟲(Cimex pilosellus))、盲蝽屬(Collaria spp.)、綠盲蝽(Creontiades dilutus)、胡椒緣蝽(Dasynus piperis)、Dichelops furcatus、厚氏長棒網蜂(Diconocoris hewetti)、棉紅蝽屬(Dysdercus spp.)、美洲蝽屬(Euschistus spp.)(例如大豆褐蝽(Euschistus heros)、褐臭美洲蝽(Euschistus servus)、三色美洲蝽(Euschistus tristigmus)、單點美洲蝽(Euschistus variolarius))、菜蝽屬(Eurydema spp.)、扁盾蝽屬(Eurygaster spp.)、茶翅蝽(Halyomorpha halys)、錘盲蝽屬(Heliopeltis spp.)、具凹巨股長蝽(Horcias nobilellus)、稻緣蝽屬(Leptocorisa spp.)、異稻緣蝽(Leptocorisa varicornis)、西部喙緣蝽(Leptoglossus occidentalis)、葉喙緣蝽(Leptoglossus phyllopus)、麗盲蝽屬(Lygocoris spp.)(例如原麗盲蝽(Lygocoris pabulinus))、草盲蝽屬(Lygus spp.)(例如豆莢灰盲蝽(Lygus elisus)、雄性金星草盲椿(Lygus hesperus)、牧草盲蝽(Lygus lineolaris))、蔴漂長蝽(Macropes excavatus)、篩豆龜蝽(Megacopta cribraria)、盲椿象科(Miridae)、金光綠盲蝽(Monalonion atratum)、綠蝽屬(Nezara spp.)(例如稻綠蝽(Nezara viridula))、小長蝽屬(Nysius spp.)、稻蝽屬(Oebalus spp.)、蝽科(Pentomidae)、方背皮蝽(Piesma quadrata)、壁蝽屬(Piezodorus spp.)(例如蓋德擬壁蝽(Piezodorus guildinii))、雜盲蝽屬(Psallus spp.)、鱷梨網蝽(Pseudacysta persea)、紅獵蝽屬(Rhodnius spp.)、可可斑褐盲蝽(Sahlbergella singularis)、栗花椿象(Scaptocoris castanea)、黑蝽屬(Scotinophora spp.)、梨冠網蝽(Stephanitis nashi)、臭蟲屬(Tibraca spp.)、錐鼻蟲屬(Triatoma spp.);
來自膜翅目(Hymenoptera)之目,例如頂切葉蟻屬(Acromyrmex spp.)、殘青葉蜂屬(Athalia spp.)(例如短斑殘青葉蜂(Athalia rosae))、切葉蟻屬(Atta spp.)、巨山蟻屬(Camponotus spp.)、長黃胡蜂屬(Dolichovespula spp.)、松葉蜂屬(Diprion spp.)(例如類歐松葉蜂(Diprion similis))、長角葉蜂屬(Hoplocampa spp.)(例如庫氏長角葉蜂(Hoplocampa cookei)、長角葉蜂蘋果長角葉蜂(Hoplocampa testudinea))、毛山蟻屬(Lasius spp.)、阿根廷螞蟻(Linepithema humile)(阿根廷虹臭蟻(Iridiomyrmex humile))、小黃家蟻(Monomorium pharaonis)、黃山蟻屬(Paratrechina spp.)、黃胡蜂屬(Paravespula spp.)、箭蟻屬(Plagiolepis spp.)、樹蜂屬(Sirex spp.)(例如雲杉樹蜂(Sirex noctilio))、入侵紅火蟻(Solenopsis invicta)、酸臭蟻屬(Tapinoma spp.)、白跗節狡臭蟻(Technomyrmex albipes)、大樹蜂屬(Urocerus spp.)、胡蜂屬(Vespa spp.)(例如黃邊胡蜂(Vespa crabro))、小火蟻(Wasmannia auropunctata)、黑樹蜂屬(Xeris spp.);
來自等足目(Isopoda)之目,例如鼠婦(Armadillidium vulgare)、壁潮蟲(Oniscus asellus)、粗礪潮蟲(Porcellio scaber);
來自等翅目(Isoptera)之目,例如乳白蟻屬(Coptotermes spp.),例如家白蟻(Coptotermes formosanus)、堆角白蟻(Cornitermes cumulans)、堆沙白蟻屬(Cryptotermes spp.)、楹白蟻屬(Incisitermes spp.)、木白蟻屬(Kalotermes spp.)、甘蔗白蟻(Microtermes obesi)、象白蟻屬(Nasutitermes spp.)、土白蟻屬(Odontotermes spp.)、洞白蟻屬(Porotermes spp.)、散白蟻屬(Reticulitermes spp.),例如黃肢散白蟻(Reticulitermes flavipes)、西方散白蟻(Reticulitermes hesperus));
來自鱗翅目(Lepidoptera)之目,例如小蠟蛾(Achroia grisella)、桑劍紋夜蛾(Acronicta major)、捲葉蛾屬(Adoxophyes spp.)(例如茶姬捲葉蛾(Adoxophyes orana))、白斑煩夜蛾(Aedia leucomelas)、地老虎屬(Agrotis spp.)(例如黃地老虎(Agrotis segetum)、小地老虎(Agrotis ipsilon))、波紋夜蛾屬(Alabama spp.)(例如棉葉波紋夜蛾(Alabama argillacea))、臍橙螟(Amyelois transitella)、條麥蛾屬(Anarsia spp.)、夜蛾屬(Anticarsia spp.)(例如大豆夜蛾(Anticarsia gemmatalis)、黄螟屬(Argyroploce spp.)、丫紋夜蛾屬(Autographa spp.)、甘藍夜蛾(Barathra brassicae)、蘋髓尖蛾(Blastodacna atra)、秈弄蝶(Borbo cinnara)、棉潛蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、蛀褐夜蛾屬(Busseola spp.)、捲葉蛾屬(Cacoecia spp.)、茶細蛾(Caloptilia theivora)、菸捲蛾(Capua reticulana)、蘋果蠹蛾(Carpocapsa pomonella)、桃小食心蟲(Carposina niponensis)、冬尺蛾(Cheimatobia brumata)、螟屬(Chilo spp.)(例如七星稻螟(Chilo plejadellus)、二化螟(Chilo suppressalis))、蘋果舞蛾(Choreutis pariana)、色捲蛾屬(Choristoneura spp.)、錁紋夜蛾(Chrysodeixis chalcites)、葡萄果蠹蛾(Clysia ambiguella)、縱捲葉野螟屬(Cnaphalocerus spp.)、瘤野螟(Cnaphalocrocis medinalis)、雲捲蛾屬(Cnephasia spp.)、細蛾屬(Conopomorpha spp.)、球頸象屬(Conotrachelus spp.)、庫塔斯屬(Copitarsia spp.)、小捲蛾屬(Cydia spp.)(例如豌豆小捲蛾(Cydia nigricana))、蘋果蠹蛾(Cydia pomonella))、諾土德達拉卡(Dalaca noctuides)、絹野螟屬(Diaphania spp.)、棉鈴蟲屬(Diparopsis spp.)、小蔗螟(Diatraea saccharalis)、梢斑螟屬(Dioryctria spp.)(例如美洲松梢斑螟(Dioryctria zimmermani))、鑽夜蛾屬(Earias spp.)、射線對小捲蛾(Ecdytolopha aurantium)、南美玉米苗斑螟(Elasmopalpus lignosellus)、甘薯桿螟(Eldana saccharina)、粉斑螟屬(Ephestia spp.)(例如菸草粉斑螟(Ephestia elutella)、地中海粉斑螟(Ephestia kuehniella))、葉小捲蛾屬(Epinotia spp.)、蘋果褐捲蛾(Epiphyas postvittana)、松尺蛾屬(Erannis spp.)、灰紋捲蛾(Erschoviella musculana)、莢斑螟屬(Etiella spp.)、豔葉夜蛾屬(Eudocima spp.)、掠捲蛾屬(Eulia spp.)、葡萄與蘋果捲葉蛾(Eupoecilia ambiguella)、黃毒蛾屬(Euproctis spp.)(例如褐尾蛾(Euproctis chrysorrhoea))、切根蟲屬(Euxoa spp.)、褐夜蛾屬(Feltia spp.)、大蠟螟(Galleria mellonella)、細蛾屬(Gracillaria spp.)、小食心蟲屬(Grapholitha spp.)(例如桃折心蟲(Grapholita molesta)、蘋小果蠹(Grapholita prunivora)、蝕葉野螟屬(Hedylepta spp.)、夜蛾屬(Helicoverpa spp.)(例如番茄夜蛾(Helicoverpa armigera)、棉鈴蟲(Helicoverpa zea))、實夜蛾屬(Heliothis spp.)(例如煙芽夜蛾(Heliothis virescens))、褐織蛾(Hofmannophila pseudospretella)、斑螟屬(Homoeosoma spp.)、長捲蛾屬(Homona spp.)、櫻桃巢蛾(Hyponomeuta padella)、柿蔕蟲蛾(Kakivoria flavofasciata)、亮灰蝶屬(Lampides spp.)、夜蛾屬(Laphygma spp.)、梨小蠹螟(Laspeyresia molesta)、茄黃斑螟(Leucinodes orbonalis)、銀潛蛾屬(例如咖啡銀潛蛾)、潛葉細蛾屬(Lithocolletis spp.)(例如蘋果斑幕潛葉細蛾(Lithocolletis blancardella))、綠果冬夜蛾(Lithophane antennata)、花翅小蛾屬(Lobesia spp.)(例如葡萄花翅小蛾(Lobesia botrana))、豆白隆切根蟲(Loxagrotis albicosta)、毒蛾屬(Lymantria spp.)(例如舞毒蛾(Lymantria dispar))、潛蛾屬(Lyonetia spp.)(例如桃潛蛾(Lyonetia clerkella))、天幕毛蟲(Malacosoma neustria)、豆莢野螟(Maruca testulalis)、甘藍夜蛾(Mamestra brassicae)、稻暮眼蝶(Melanitis leda)、毛脛夜蛾屬(Mocis spp.)、Monopis obviella、黏夜蛾(Mythimna separata)、橡長角蛾(Nemapogon cloacellus)、水螟屬(Nymphula spp.)、Oiketicus屬、蠹野螟屬(Omphisa spp.)、尺蛾屬(Operophtera spp.)、巫夜蛾屬(Oria spp.)、瘤叢螟屬(Orthaga spp.)、玉米螟屬(Ostrinia spp.)(例如歐洲玉米螟(Ostrinia nubilalis))、松夜蛾(Panolis flammea)、稻弄蝶屬(Parnara spp.)、紅鈴蟲屬(Pectinophora spp.)(例如棉紅鈴蟲(Pectinophora gossypiella))、潛跳甲屬(Perileucoptera spp.)、茄麥蛾屬(Phthorimaea spp.)(例如馬鈴薯塊莖蛾(Phthorimaea operculella))、柑橘潛葉蛾(Phyllocnistis citrella)、小潛細蛾屬(Phyllonorycter spp.)(例如幕斑小潛細蛾(Phyllonorycter blancardella)、山楂小潛細蛾(Phyllonorycter crataegella))、白粉蝶屬(Pieris spp.)(例如紋白蝶(Pieris rapae))、荷蘭石竹小捲蛾(Platynota stultana)、印度穀螟(Plodia interpunctella)、金翅夜蛾屬(Plusia spp.)、小菜蛾(Plutella xylostella)(=小菜蛾(Plutella maculipennis))、Podesia屬(例如Podesia syringae) 、小白巢蛾屬(Prays spp.)、Prodenia屬、菸草天蛾(Protoparce spp.)、黏蟲屬(Pseudaletia spp.)(例如一星黏蟲(Pseudaletia unipuncta)、大豆尺夜蛾(Pseudoplusia includens)、歐洲玉蜀黍螟(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、禾螟屬(Schoenobius spp.)(例如三化螟(Schoenobius bipunctifer))、白禾螟屬(Scirpophaga spp.)(例如稻白禾螟(Scirpophaga innotata))、黃地老虎(Scotia segetum)、蛀莖夜蛾屬(Sesamia spp.)(例如稻蛀莖夜蛾(Sesamia inferens))、長須捲蛾屬(Sparganothis spp.)、灰翅夜蛾屬(Spodoptera spp.)(例如厄地那灰翅夜蛾(Spodoptera eradiana)、甜菜葉蛾(Spodoptera exigua)、草地夜蛾(Spodoptera frugiperda))、條狀黏蟲(Spodoptera praefica)、舉肢蛾屬(Stathmopoda spp.)、黃鵪菜屬(Stenoma spp.)、花生須峭麥蛾(Stomopteryx subsecivella)、透翅蛾屬(Synanthedon spp.)、安第斯馬鈴薯塊莖蛾(Tecia solanivora)、異舟蛾屬(Thaumetopoea spp.)、幹煞夜蛾(Thermesia gemmatalis)、木塞衣蛾(Tinea cloacella)、衣蛾(Tinea pellionella)、袋衣蛾(Tineola bisselliella)、捲葉蛾屬(Tortrix spp.)、毛氈衣蛾屬(Trichophaga tapetzella)、粉夜蛾屬(Trichoplusia spp.)(例如粉紋夜蛾(Trichoplusia ni))、三化螟(Tryporyza incertulas)、番茄斑潛蠅(Tuta absoluta)、灰蝶屬(Virachola spp.);
來自直翅目(Orthoptera)或跳躍亞目(Saltatoria)之目,例如家蟋蟀(Acheta domesticus)、Dichroplus屬、螻蛄屬(Gryllotalpa spp.)(例如歐洲螻蛄(Gryllotalpa gryllotalpa))、蔗蝗屬(Hieroglyphus spp.)、飛蝗屬(Locusta spp.)(例如東亞飛蝗(Locusta migratoria))、黑蝗屬(Melanoplus spp.)(例如赤地蚱蜢(Melanoplus devastator))、烏蘇裡擬寰螽(Paratlanticus ussuriensis)、沙漠蝗蟲(Schistocerca gregaria);
來自毛蝨目(Phthiraptera)之目,例如畜蝨屬(Damalinia spp.)、血蝨屬(Haematopinus spp.)、長齶蝨屬(Linognathus spp.)、蝨屬(Pediculus spp.)、葡萄根瘤蚜(Phylloxera vastatrix)、陰蝨(Phthirus pubis)、毛蝨屬(Trichodectes spp.);
來自囓蟲目(Psocoptera)之目,例如鱗齧蟲屬(Lepinotus spp.)、蝨囓屬(Liposcelis spp.);
來自隱翅目(Siphonaptera)之目,例如角葉蚤屬(Ceratophyllus spp.)、櫛頭蚤屬(Ctenocephalides spp.)(例如犬櫛頭蚤(Ctenocephalides canis)、貓櫛頭蚤(Ctenocephalides felis))、人蚤(Pulex irritans)、穿皮潛蚤(Tunga penetrans)、印度鼠蚤(Xenopsylla cheopis);
來自纓翅目(Thysanoptera)之目,例如玉米黃呆薊馬(Anaphothrips obscurus)、稻薊馬(Baliothrips biformis)、中斑圍孔薊馬(Chaetanaphothrips leeuweni)、鮮食葡萄鐮薊馬(Drepanothrips reuteri)、黃化恩薊馬(Enneothrips flavens)、花薊馬屬(Frankliniella spp.)(例如菸褐花薊馬(Frankliniella fusca)、西花薊馬(Frankliniella occidentalis)、梳缺花薊馬(Frankliniella schultzei)、美東花薊馬(Frankliniella tritici)、越橘花薊馬(Frankliniella vaccinii)、威廉期花薊馬(Frankliniella williamsi))、簡管薊馬屬(Haplothrips spp.)、陽薊馬屬(Heliothrips spp.)、溫室條籬薊馬(Hercinothrips femoralis)、卡薊馬屬(Kakothrips spp.)、腹鉤薊馬(Rhipiphorothrips cruentatus)、硬薊馬屬(Scirtothrips spp.)、豆塔薊馬(Taeniothrips cardamomi)、薊馬屬(Thrips spp.)(例如南黃薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci));
來自衣魚亞目(Zygentoma)(=纓尾目(Thysanura))之目,例如櫛衣魚屬(Ctenolepisma spp.)、普通衣魚(Lepisma saccharina)、盜火蟲(Lepismodes inquilinus)、斑衣魚(Thermobia domestica);
來自結閥綱(Symphyla)之綱,例如麼蚰屬(Scutigerella spp.)(例如白松蟲(Scutigerella immaculata);
來自軟體動物門之門,例如來自雙殼綱(Bivalvia)之綱,例如飾貝屬(Dreissena spp.);
以及來自腹足綱(Gastropoda)之綱,例如阿勇蛞蝓屬(Arion spp.)(例如愛特盧夫斯阿勇蛞蝓(Arion ater rufus))、雙臍螺屬(Biomphalaria spp.)、泡螺屬(Bulinus spp.)、野蛞蝓屬(Deroceras spp.)(例如光滑野蛞蝓(Deroceras laeve))、土蝸屬(Galba spp.)、椎實螺屬(Lymnaea spp.)、釘螺屬(Oncomelania spp.)、福壽螺屬(Pomacea spp.)、琥珀螺屬(Succinea spp.);
來自圓形動物門(Nematoda)之門的植物害蟲,即植物寄生線蟲,特別為野外墊刃線蟲屬(Aglenchus spp.)(例如居農野外墊刃線蟲(Aglenchus agricola))、粒線蟲屬(Anguina spp.)(例如小麥粒線蟲(Anguina tritici))、滑刃線蟲屬(Aphelenchoides spp.)(例如花生滑刃線蟲(Aphelenchoides arachidis)、草莓滑刃線蟲(Aphelenchoides fragariae))、刺線蟲屬(Belonolaimus spp.)(例如細小刺線蟲(Belonolaimus gracilis)、雜草刺線蟲(Belonolaimus longicaudatus)、諾頓剌線蟲(Belonolaimus nortoni))、傘滑刃線蟲屬(Bursaphelenchus spp.)(例如椰樹傘滑刃線蟲(Bursaphelenchus cocophilus)、荒漠傘滑刃線蟲(Bursaphelenchus eremus)、松材傘滑刃線蟲(Bursaphelenchus xylophilus))、壞死線蟲屬(Cacopaurus spp.)(例如癌疫壞死線蟲(Cacopaurus pestis))、小環線蟲屬(Criconemella spp.)(例如彎曲小環線蟲(Criconemella curvata)、刻線小環線蟲(Criconemella onoensis)、裝飾小環線蟲(Criconemella ornata)、如思木小環線蟲(Criconemella rusium)、薄葉小環線蟲(Criconemella xenoplax)(=異盤中環線蟲(Mesocriconema xenoplax)))、輪線蟲屬(Criconemoides spp.)(例如非尼艾輪線蟲(Criconemoides ferniae)、蝸諾昔輪線蟲(Criconemoides onoense)、蝸那土輪線蟲(Criconemoides ornatum))、莖線蟲屬(Ditylenchus spp.)(例如鱗球莖莖線蟲(Ditylenchus dipsaci))、錐線蟲屬(Dolichodorus spp.)、球胞囊線蟲屬(Globodera spp.)(例如馬鈴薯球胞囊線蟲(Globodera pallida)、馬鈴薯金線蟲(Globodera rostochiensis))、螺旋線蟲屬(Helicotylenchus spp.)(例如雙宮螺旋線蟲(Helicotylenchus dihystera))、半輪線蟲屬(Hemicriconemoides spp.)、鞘線蟲屬(Hemicycliophora spp.)、異皮線蟲屬(Heterodera spp.)(例如燕麥異皮線蟲(Heterodera avenae)、大豆異皮線蟲(Heterodera glycines)、甜菜異皮線蟲(Heterodera schachtii))、潛根線蟲屬(Hirschmaniella spp.)、紐帶線蟲屬(Hoplolaimus spp.)、長針線蟲屬(Longidorus spp.)(例如非洲長針線蟲 (Longidorus africanus))、根瘤線蟲屬(Meloidogyne spp.)(例如奇氏根瘤線蟲(Meloidogyne chitwoodi)、擬禾本科根瘤線蟲(Meloidogyne fallax)、北方根瘤線蟲(Meloidogyne hapla)、南方根瘤線蟲(Meloidogyne incognita)、瓢線蟲屬(Meloinema spp.)、假根瘤線蟲屬(Nacobbus spp.)、擬莖線蟲屬(Neotylenchus spp.)、擬長針線蟲屬(Paralongidorus spp.)、擬滑刃屬(Paraphelenchus spp.)、擬毛刺線蟲屬(Paratrichodorus spp.)(例如微小擬毛刺線蟲(Paratrichodorus minor))、短體線蟲屬(Pratylenchus spp.)(例如穿刺短體線蟲(Pratylenchus penetrans))、假海矛線蟲屬(Pseudohalenchus spp.)、平滑墊刃線蟲屬(Psilenchus spp.)、斑皮線蟲屬(Punctodera spp.)、五溝線蟲屬(Quinisulcius spp.)、穿孔線蟲屬(Radopholus spp.)(例如柑橘穿孔線蟲(Radopholus citrophilus)、香蕉穿孔線蟲(Radopholus similis))、腎型線蟲屬(Rotylenchulus spp.)、盤旋線蟲屬(Rotylenchus spp.)、盾線蟲屬(Scutellonema spp.)、亞粒線蟲屬(Subanguina spp.)、毛刺線蟲屬(Trichodorus spp.)(例如鈍毛刺線蟲(Trichodorus obtusus)、原始毛刺線蟲(Trichodorus primitives))、矮化線蟲屬(Tylenchorhynchus spp.)(例如飾環矮化線蟲(Tylenchorhynchus annulatus))、穿刺線蟲屬(Tylenchulus spp.)(例如半穿刺線蟲(Tylenchulus semipenetrans))、劍線蟲屬(Xiphinema spp.)(例如標記劍線蟲(Xiphinema index))。
式(I)化合物於某些濃度或施用率下亦可視需要地用作除草劑、安全劑、生長調節劑或改良植物性質之劑、用作殺微生物劑或殺配子劑,例如用作殺真菌劑、抗黴劑、殺細菌劑、殺病毒劑(包括對抗類病毒之劑),或用作對抗MLO(類黴漿菌有機體(mycoplasma-like organism))及RLO(類立克次體有機體(rickettsia-like organism))之劑。若適合的話,彼等亦可用作合成其他活性化合物之中間物或前驅物。
調配物
本發明進一步關於調配物及由其製備成殺蟲劑之使用形式(例如澆灌、滴注及噴灑液),其包含至少一種式(I)化合物。在一些情形下,使用形式包含其他殺蟲劑及/或改良作用之佐劑(諸如滲透劑),例如植物油(例如,菜籽油、葵花油)、礦物油(例如,石蠟油)、植物脂肪酸之烷酯(例如,菜籽油甲酯或大豆油甲酯)、或烷醇烷氧化物及/或擴散劑(例如烷基矽氧烷)及/或鹽(例如有機或無機銨或鏻鹽,例如硫酸銨或磷酸氫二銨)及/或滯留促進劑(例如磺醯基琥珀酸二辛酯或羥丙基膠豆聚合物)及/或保濕劑(例如甘油)及/或肥料(例如含銨-、鉀-或磷-之肥料)。
習知的調配物為例如:水溶性液體(SL)、乳化濃縮劑(EC)、水性乳液(EW)、懸浮濃縮劑(SC、SE、FS、OD)、水可分散性粒劑(WG)、粒劑(GR)及膠囊濃縮劑(CS);此等及其他可能的調配物類型係說明於例如FAO/WHO殺蟲劑規格聯合會議(FAO/WHO Joint Meeting on Pesticide Specifications,2004,ISBN:9251048576)所編製之Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers-173)。調配物除了一或多種式(I)化合物以外,可視需要包含其他的農化活性化合物。
此等較佳為包含助劑(例如增量劑、溶劑、自發性促進劑、載劑、乳化劑、分散劑、霜凍保護劑、殺生物劑、增稠劑及/或其他的助劑,例如佐劑)的調配物或使用形式。在此情況下的佐劑為增進調配物的生物作用之組分,而沒有本身具有任何生物作用的組分。佐劑之實例為促進滯留、擴散、附著於葉表面或滲透之劑。
此等調配物係以已知的方式製備,例如藉由將式(I)化合物與助劑(諸如,例如增量劑、溶劑及/或固體載劑及/或其他的助劑,諸如,例如界面活性劑)混合。調配物係在適當設備中或者在施用前或期間製造。
所使用的助劑可為適合於將特定性質(諸如某些物理、技術及/或生物性質)賦予式(I)化合物之調配物或由此等調配物所製備之使用形式(例如,備用殺蟲劑,諸如噴灑液或拌種產物)的物質。
適當增量劑為(例如)水、極性和非極性有機化學液體,例如來自下列類別:芳族和非芳族烴(諸如石蠟、烷基苯、烷基萘、氯苯)、醇和多元醇(若適當時,其亦可經取代、醚化與/或酯化)、酮(諸如丙酮、環己酮)、酯(包括脂肪和油)及(聚)醚、未取代及經取代的胺、醯胺、內醯胺(諸如N-烷基吡咯啶酮)和內酯、碸及亞碸(諸如二甲亞碸)、碳酸酯和腈。
若所使用的增量劑為水,則亦有可能使用例如有機溶劑作為輔助溶劑。基本上,適當的液體溶劑為:芳族烴(諸如二甲苯、甲苯或烷基萘)、氯化芳族烴或氯化脂族烴(諸如氯苯、氯乙烯或二氯甲烷)、脂族烴(諸如環己烷或石蠟,例如礦物油分餾物、礦物油和植物油)、醇(諸如丁醇或二醇)及其醚和酯、酮(諸如丙酮、甲基乙酮、甲基異丁酮或環己酮)、強極性溶劑(諸如二甲基甲醯胺和二甲亞碸)、碳酸酯諸如碳酸丙二酯、碳酸丁二酯、碳酸二乙酯或碳酸二丁酯、或腈諸如乙腈或丙腈。
原則上,可能使用所有適當溶劑。適當溶劑之實例為芳族烴(諸如二甲苯、甲苯或烷基萘)、氯化芳族烴或氯化脂族烴(諸如氯苯、氯乙烯或二氯甲烷)、脂族烴(諸如環己烷、石蠟、礦物油分餾物、礦物油和植物油)、醇(諸如甲醇、乙醇、異丙醇、丁醇或二醇)及其醚和酯、酮(諸如丙酮、甲基乙酮、甲基異丁酮或環己酮)、強極性溶劑(諸如二甲亞碸)、碳酸酯諸如碳酸丙二酯、碳酸丁二酯、碳酸二乙酯或碳酸二丁酯、或腈諸如乙腈或丙腈,以及水。
原則上,可能使用所有適當載劑。有用的載劑尤其包括:例如銨鹽及磨碎天然礦物(諸如高嶺土、黏土、滑石、白堊、石英、鎂鋁海泡石、蒙脫土或矽藻土)和磨碎合成礦物(諸如細碎的矽石、氧化鋁和天然或合成矽酸鹽)、樹脂、蠟及/或固體肥料。同樣地可使用該等載劑之混合物。用於粒劑之有用載劑包括:例如粉碎且分級之天然礦石(諸如方解石、大理石、浮石、海泡石、白雲石)及無機和有機粉末之合成顆粒,以及有機材料(諸如鋸屑、紙、椰子殼、玉米穗軸和菸草稈)之顆粒。
亦可使用液化氣體增量劑或溶劑。特別適合的增量劑或載劑為彼等在標準溫度下及在標準壓力下呈氣態的增量劑或載劑,例如霧劑推進劑,諸如鹵化烴,以及丁烷、丙烷、氮氣和二氧化碳。
具有離子或非離子性質之乳化劑及/或泡沫形成劑、分散劑或潤濕劑,或此等界面活性劑之混合物的實例為聚丙烯酸之鹽、木質素磺酸之鹽、酚磺酸或萘磺酸之鹽、環氧乙烷與脂肪醇或與脂肪酸或與脂肪胺、與經取代的酚(較佳為烷基酚或芳基酚)之聚縮物、磺酸基琥珀酸酯之鹽、牛磺酸衍生物(較佳為牛磺酸烷酯)、羥乙磺酸鹽衍生物、聚乙氧基化醇或酚之磷酸酯、多元醇之脂肪酸酯,及含硫酸根、磺酸根和磷酸根之化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、蛋白質水解物、木質素亞硫酸鹽廢液和甲基纖維素。若式(I)化合物中之一者及/或惰性載劑中之一者不溶於水中且當施用係發生在水中時,則界面活性劑的存在是有利的。
可能使用著色劑(諸如無機顏料,例如氧化鐵、氧化鈦和普魯士藍、及有機染料,諸如茜素染料、偶氮染料和金屬酞花青染料)、及營養素和微量營養素(諸如鐵、錳、硼、銅、鈷、鉬和鋅之鹽)作為調配物及由其所衍生之施用形式中的其他助劑。
另外的組分可為穩定劑(諸如低溫穩定劑)、防腐劑、抗氧化劑、光穩定劑或其他改良化學及/或物理穩定性之劑。亦可存在泡沫形成劑或消泡劑。
膠黏劑(諸如羧甲基纖維素)及呈粉末、顆粒或膠乳形式的天然和合成聚合物(諸如阿拉伯膠、聚乙烯醇和聚乙酸乙烯酯)、或者其他的天然磷脂(諸如腦磷脂和卵磷脂)及合成磷脂亦可以另外的助劑存在於調配物及由其所衍生之使用形式中。其他可能的助劑為礦物油與植物油。
視需要地,其他助劑可存在於調配物及由其所衍生之使用形式中。該等添加劑的實例包括香料、保護性膠體、黏合劑、黏著劑、增稠劑、觸變劑、滲透劑、滯留促進劑、穩定劑、螯合劑、錯合劑、保濕劑、擴散劑。通常,可將式(I)化合物與常用於調配目的之任何固體或液體添加劑組合。
有用的滯留促進劑包括所有彼等減少動態表面張力之物質,例如磺酸基琥珀酸二辛酯,或增加黏彈性之物質,例如羥丙基膠豆聚合物。
在本情況下適當滲透劑為所有彼等通常用於改良農化活性化合物滲透至植物中之物質。滲透劑在此情況下係以彼等自(通常為水性)施用液體及/或自噴灑塗層滲透至植物的角質層且因此增加活性化合物在角質層中的移動性之能力來定義。文獻(Baur et al., 1997, Pesticide Science 51, 131-152)中所述的方法可用於測定此性質。實例包括醇烷氧化物(諸如,椰子脂肪乙氧化物(10)或異十三基乙氧化物(12))、脂肪酸酯(例如,菜籽油甲酯或大豆油甲酯)、脂肪胺烷氧化物(例如,牛脂胺乙氧化物(15))、或銨及/或鏻鹽(例如,硫酸銨或磷酸氫二銨)。
調配物較佳地包含以調配物的重量為基準計介於0.00000001和98重量%之間的式(I)化合物,或特佳地,介於0.01重量%和95重量%之間的式(I)化合物,更佳為介於0.5重量%和90重量%之間的式(I)化合物。
式(I)化合物在由調配物製備之使用形式(特別為殺蟲劑)中之含量可在寬廣的範圍內改變。式(I)化合物在使用形式中之濃度以使用形式的重量為基準計通常介於0.00000001和95重量%之間的式(I)化合物,較佳為介於0.00001和1重量%之間。以適合於使用形式的習知方式使用化合物。
混合物
式(I)化合物亦可以與一或多種適當殺真菌劑、殺細菌劑、殺蟎劑、殺軟體動物劑、殺線蟲劑、殺昆蟲劑、微生物劑、有益物種、除草劑、肥料、驅鳥劑、植物強直劑(phytotonics)、滅菌劑、安全劑、化學傳訊素及/或植物生長調節劑之混合物使用,以因此例如擴增作用範圍、延長作用期間、增加作用率、防止排斥或防止抗性進化。此外,該等活性化合物組合可改良植物生長及/或對非生物因子(例如,高或低溫、乾旱或含升高的水量或土壤鹽度)之耐受性。亦可能改良開花和結果性能、最佳化發芽能力和根發育、促進收成和改良產率、影響成熟、改良收成產物之品質及/或營養價值、延長貯藏壽命及/或改良收成產物之加工性。
此外,式(I)化合物可與其他的活性化合物或化學傳訊素諸如引誘劑及/或驅鳥劑及/或植物活化劑及/或生長調節劑及/或肥料之混合物存在。同樣地,式(I)化合物可使用於改良植物性質,諸如,例如收成物質的生長、產率及品質。
在根據本發明一特殊實施態樣中,式(I)化合物係以與其他化合物(較佳為彼等如下所述者)之混合物存在於調配物或由此等調配物所製備之使用形式中。
若下述化合物中之一者可以不同互變異構物形式出現時,則亦包括此等形式,即使在各情形下未明確述及。此外,所有命名的混合伴體若彼等的官能基能夠的話,則可視需要與適當鹼或酸形成鹽。
殺昆蟲劑 / 殺蟎劑 / 殺線蟲劑
在本文中以彼等的俗名指定之活性化合物為已知且描述於(例如)“殺蟲劑手冊(The Pesticide Manual”第16版, British Crop Protection Council 2012)中或可在網際網路上找到(例如http://www.alanwood.net/Pesticide)。分類係根據在本專利申請案申請時的現行作用分類方案之IRAM模式(IRAC Mode of Action Classification Scheme)。
(1)乙醯膽鹼酯酶(AChE)抑制劑,較佳為胺基甲酸酯類,其選自棉鈴威(alanycarb)、得滅克(aldicarb)、免敵克(bendiocarb)、免扶克(benfuracarb)、佈嘉信(butocarboxim)、丁酮碸威(butoxycarboxim)、加保利(carbaryl)、加保扶(carbofuran)、丁基加保扶(carbosulfan)、愛芬克(ethiofencarb)、丁基滅必蝨(fenobucarb)、覆滅竝(formetanate)、扶線威(furathiocarb)、滅必蝨(isoprocarb)、滅賜克(methiocarb)、納乃得(methomyl)、治滅蝨(metolcarb)、歐殺滅(oxamyl)、比加普(pirimicarb)、安丹(propoxur)、硫敵克(thiodicarb)、硫伐隆(thiofanox)、唑蚜威(triazamate)、混殺威(trimethacarb)、XMC及滅爾蝨(xylylcarb)、或有機磷酸鹽類,其選自歐殺松(acephate)、亞滅松(azamethiphos)、谷速松(azinphos)-乙基、谷速松-甲基、硫線磷(cadusafos)、氯氧磷(chlorethoxyfos)、克芬松(chlorfenvinphos)、氯甲硫磷(chlormephos)、陶斯松(chlorpyrifos)-甲基、牛壁逃(coumaphos)、氰乃松(cyanophos)、滅賜松(demeton-S-methyl)、大利松(diazinon)、二氯松(dichlorvos)/DDVP、雙特松(dicrotophos)、大滅松(dimethoate)、甲基毒蟲畏(dimethylvinphos)、二硫松(disulfoton)、EPN、愛殺松(ethion)、普伏松(ethoprophos)、氨磺磷(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬殺松(fenthion)、福賽絕(fosthiazate)、飛達松(heptenophos)、依米賽松(imicyafos)、亞芬松(isofenphos)、水楊酸O-(甲氧胺基硫磷醯基)酯異丙酯、加福松(isoxathion)、馬拉松(malathion)、滅加松(mecarbam)、達馬松(methamidophos)、滅大松(methidathion)、美文松(mevinphos)、亞素靈(monocrotophos)、乃力松(naled)、歐滅松(omethoate)、滅多松(oxydemeton-methyl)、巴拉松(parathion)-甲基、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、益滅松(phosmet)、福賜米松(phosphamidon)、巴賽松(phoxim)、亞特松(pirimiphos-methyl)、佈飛松(profenofos)、撲達松(propetamphos)、普硫松(prothiofos)、白克松(pyraclofos)、必芬松(pyridaphenthion)、拜裕松(quinalphos)、硫特普(sulfotep)、丁嘧硫磷(tebupirimfos)、亞培松(temephos)、托福松(terbufos)、樂本松(tetrachlorvinphos)、硫滅松(thiometon)、三落松(triazophos)、三氯松(triclorfon)及繁米松(vamidothion)。
(2) GABA-閘控之氯離子通道阻斷劑,較佳為環二烯有機氯類,其選自克氯丹(chlordane)及安殺番(endosulfan)或苯基吡唑類(飛普洛類(fiproles)),例如乙蟲清(ethiprole)及芬普尼(fipronil)。
(3) 鈉通道調節劑,較佳為擬除蟲菊酯類(pyrethroids),其選自阿納寧(acrinathrin)、亞列寧(allethrin)、d-順-反亞列寧、d-反亞列寧、畢芬寧(bifenthrin)、百亞列寧(bioallethrin)、百亞列寧-s-環戊烯基異構物、百列滅寧(bioresmethrin)、乙氰菊酯(cycloprothrin)、賽扶寧(cyfluthrin)、β-賽扶寧、賽洛寧(cyhalothrin)、λ-賽洛寧、γ-賽洛寧、亞滅寧(cypermethrin)、α-亞滅寧、β-亞滅寧、θ-亞滅寧、ξ-亞滅寧、賽芬寧(cyphenothrin) [(1R)-反式異構物]、第滅寧(deltamethrin)、益避寧(empenthrin)[(EZ)-(1R) 異構物] 、益化利(esfenvalerate)、依芬寧(etofenprox)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、護賽寧(flucythrinate)、福滅寧(flumethrin)、福化利(τ-fluvalinate)、合芬寧(halfenprox)、依普寧(imiprothrin)、剋特寧(kadethrin)、莫弗洛寧(momfluorothrin)、百滅寧(permethrin)、酚丁滅蝨(phenothrin) [(1R)-反-異構物]、普亞列寧(prallethrin)、除蟲菊素(pyrethrine)(除蟲菊精(pyrethrum))、列滅寧(resmethrin)、氟矽菊酯(silafluofen)、七氟菊酯(tefluthrin)、治滅寧(tetramethrin)、治滅寧[(1R) 異構物]]、泰滅寧(tralomethrin)和拜富寧(transfluthrin)或DDT或甲氧滴滴涕(methoxychlor)。
(4) 菸鹼能乙醯膽鹼受體(nAChR)競爭調節劑,該較佳新菸鹼類,其選自亞滅培(acetamiprid)、可尼丁(clothianidin)、達特南(dinotefuran)、益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、噻蟲啉(thiacloprid)和賽速安(thiamethoxam)或尼古丁(nicotine)或氟啶蟲胺腈(sulfoxaflor)或氟吡呋喃酮(flupyradifurone)。
(5) 菸鹼能乙醯膽鹼受體(nAChR)別位調節劑,較佳為賜諾斯類(spinosyns),其選自賜諾特(spinetoram)和賜諾殺(spinosad)。
(6) 麩胺酸閘控之氯離子通道(GluCl)別位調節劑,較佳為阿維菌素(avermectins)/米貝黴素(milbemycins),其選自阿巴汀(abamectin)、因滅汀(emamectin benzoate)、雷皮菌素(lepimectin)和密滅汀(milbemectin)。
(7) 保幼激素模擬物,較佳為保幼激素類似物,其選自烯蟲乙酯(hydroprene)、烯蟲炔酯(kinoprene)和美賜平(methoprene)、或芬諾克(fenoxycarb)或百利普芬(pyriproxyfen)。
(8) 雜項非特異性(多位置)抑制劑,較佳為鹵烷類,其選自溴甲烷及其他鹵烷類;或氯化苦(chloropicrin);硫醯氟(sulphuryl fluoride)或硼砂(borax)或吐酒石或異氰酸甲酯產生劑,其選自邁隆(diazomet)和斯美地(metam)。
(9) 弦音器(Chordotonal organ) TRPV通道調節劑,其選自吡蚜酮(pymetrozine)或氟蟲吡喹(pyrifluquinazone)。
(10) 蟎生長抑制劑,其選自克芬蟎(clofentezine)、合賽多(hexythiazox)、氟蟎𠯤(diflovidazin)及依殺蟎(etoxazole)。
(11) 昆蟲腸膜之微生物干擾劑,其選自蘇力菌以色列亞種(Bacillus thuringiensis subspecies israelensis)、球形芽孢桿菌(Bacillus sphaericus)、蘇力菌鮎澤亞種(Bacillus thuringiensis subspecies aizawai)、蘇力菌庫斯克亞種(Bacillus thuringiensis subspecies kurstaki)、蘇力菌擬步行蟲亞種(Bacillus thuringiensis subspecies tenebrionis),及BT植物蛋白質,其選自Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb和Cry34Ab1/35Ab1。
(12) 粒腺體ATP合成酶之抑制劑,較佳為ATP干擾劑,其選自汰芬隆(diafenthiuron)或有機錫化合物,其選自亞環錫(azocyclotin)、錫蟎丹(cyhexatin)及芬佈賜(fenbutatin oxide)或毆蟎多(propargite)或得脫蟎(tetradifon)。
(13) 經由質子梯度干擾之氧化性磷酸化去偶合劑,其選自克凡派(Chlorfenapyr)、DNOC及氟蟲胺(sulfluramid)。
(14) 菸鹼能乙醯膽鹼受體通道阻斷劑,其選自免速達(bensultap)、培丹(cartap)鹽酸鹽、硫賜安(thiocylam)及殺蟲雙(thiosultap-sodium)。
(15) 第0型甲殼素生物合成之抑制劑其選自雙三氟蟲脲(bistrifluron)、克福隆(chlorfluazuron)、二福隆(diflubenzuron)、氟蟎脲(flucycloxuron)、氟芬隆(flufenoxuron)、六伏隆(hexaflumuron)、祿芬隆(lufenuron)、諾伐隆(novaluron)、諾伏隆(noviflumuron)、得福隆(teflubenzuron)及三伏隆(triflumuron)。
(16) 第1型甲殼素生物合成之抑制劑,例如布芬淨(buprofezin)。
(17) 脫皮干擾劑(特別是用於雙翅目(Diptera),即雙翅目昆蟲),其選自賽滅淨(cyromazine)。
(18) 蛻皮激素受體促效劑,其選自可芬諾(chromafenozide)、氯蟲醯肼(halofenozide)、滅芬諾(methoxyfenozide)及得芬諾(tebufenozide)。
(19) 章魚胺能受體促效劑,其選自三亞蟎(amitraz)。
(20) 粒腺體複合物III電子傳遞抑制劑,其選自海滅隆(hydramethylnone)或亞醌蟎(acequinocyl)及嘧蟎酯(fluacrypyrim)。
(21) 粒腺體複合物I電子傳遞抑制劑,較佳為METI殺蟎劑,其選自芬殺蟎(fenazaquin)、芬普蟎(fenpyroximate)、畢汰芬(pyrimidifen)、畢達本(pyridaben)、得芬瑞(tebufenpyrad)和脫芬瑞(tolfenpyrad)或魚藤酮(rotenone)(Derris)。
(22) 電壓依賴性鈉通道阻斷劑,其選自因得克(indoxacarb)或美氟綜(metaflumizone)。
(23) 乙醯基CoA羧酶之抑制劑,較佳為特窗酸和特密酸(tetramic acid)衍生物,其選自賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)及螺蟲乙酯(spirotetramat)。
(24) 粒腺體複合物IV電子傳遞抑制劑,較佳為膦類,其選自磷化鋁、磷化鈣、膦及磷化鋅或氰化物,其選自氰化鈣、氰化鉀和氰化鈉。
(25) 粒腺體複合物II電子傳遞抑制劑,較佳為β-酮腈衍生物,其選自腈吡蟎酯(cyenopyrafen)及賽芬蟎(cyflumetofen),及羧醯替苯胺類,其選自派福佈麥(pyflubumide)。
(28) 藍尼定(Ryanodine)受體調節劑,較佳為二醯胺類,其選自氯蟲醯胺(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)及氟蟲醯胺(flubendiamide),
(29) 弦音器調節劑(具有未定義的目標位置),其選自氟尼胺(flonicamid)。
(30) 其他活性化合物,其選自阿西諾派(Acynonapyr)、艾飛撲平(Afidopyropen)、阿佛拉那(Afoxolaner)、印楝素(Azadirachtin)、苯洛賽(Benclothiaz)、西脫蟎(Benzoximate)、聯苯肼酯(Bifenazate)、布洛苯胺(Broflanilide)、新殺蟎(Bromopropylate)、蟎離丹(Chinomethionat)、氯普亞列寧(Chloroprallethrin)、冰晶石(Cryolite)、環溴蟲醯胺(Cyclaniliprole)、環氧蟲啶(Cycloxaprid)、氯氟氰蟲醯胺(Cyhalodiamide)、二氯滅𠯤(Dicloromezotiaz)、大克蟎(Dicofol)、ε-甲氧苄氟菊酯(Metofluthrin)、ε-莫弗洛寧(Momfluthrin)、芬滅克(Flometoquin)、氟紮吲哚巾(Fluazaindolizine)、氟噻蟲碸(Fluensulfone)、嘧蟲胺(Flufenerim)、氟菌蟎酯(Flufenoxystrobin)、丁烯氟蟲腈(Flufiprole)、氟殺逢(Fluhexafon)、氟吡菌醯胺(Fluopyram)、福拉庇力敏(Flupyrimin)、氟拉蘭(Fluralaner)、氟米塔麥(Fluxametamide)、呋喃蟲醯肼(Fufenozide)、戊吡蟲胍(Guadipyr)、七扶寧(Heptafluthrin)、氯噻啉(Imidaclothiz)、依普同(Iprodione)、κ-畢芬寧(Bifenthrin)、κ-七氟菊酯(Tefluthrin)、羅提蘭(Lotilaner)、氯氟醚菊酯(Meperfluthrin)、歐殺諾非(oxazosulfyl)、哌蟲啶(Paichongding)、必達利(Pyridalyl)、必伏隆(Pyrifluquinazon)、嘧蟎胺(Pyriminostrobin)、螺蟎雙酯(Spirobudiclofen)、賜派地爾(Spiropidion)、四氟醚菊酯(Tetramethylfluthrin)、四尼利普洛(Tetraniliprole)、四氯查尼普洛(Tetrachlorantraniliprole)、泰夠蘭(Tigolaner)、替阿札芬(Tioxazafen)、硫氟肟醚(Thiofluoximate)、三氟米比瑞(Triflumezopyrim)和碘甲烷;另外以堅強桿菌(Bacillus firmus)為主之製劑(I-1582,BioNeem,Votivo)、以及下列化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(從WO2006/043635得知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(從WO2003/106457得知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]異菸鹼醯胺(從WO2006/003494得知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羥基-8-甲氧基-1,8-二氮雜螺[4.5]癸-3-烯-2-酮(從WO 2010052161得知)(CAS 1225292-17-0)、碳酸3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-側氧-1,8-二氮雜螺[4.5]癸-3-烯-4-基酯乙基酯(從EP 2647626得知)(CAS-1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(從WO2004/099160得知)(CAS 792914-58-0)、PF1364(從JP2010/018586得知)(CAS 1204776-60-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亞基]-1,1,1-三氟丙-2-酮(從WO2013/144213得知)(CAS 1461743-15-6)、N-[3-(苯甲基胺甲醯基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲醯胺(從WO2010/051926得知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基胺甲醯基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲醯胺(從CN103232431得知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異㗁唑基]-2-甲基-N-(順-1-氧負離子基-3-硫呾基)苯甲醯胺、4-[5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異㗁唑基]-2-甲基-N-(反 -1-氧負離子基-3-硫呾基)苯甲醯胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氫-5-(三氟甲基)-3-異㗁唑基]-2-甲基-N-(順-1-氧負離子基-3-硫呾基)苯甲醯胺(從WO 2013/050317 A1得知)(CAS 1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亞磺醯基]丙醯胺(從WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1得知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]胺基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亞磺醯基]-1H-吡唑-3-甲腈(從CN 101337937 A得知)(CAS 1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲胺基)硫酮基甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺、(Liudaibenjiaxuanan,從CN 103109816 A得知)(CAS 1232543-85-9);N-[4-氯-2-[[(1,1-二甲基乙基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-甲醯胺(從WO 2012/034403 A1得知)(CAS 1268277-22-0)、N-[2-(5-胺基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(從WO 2011/085575 A1得知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)嘧啶(從CN 101337940 A得知)(CAS 1108184-52-6);(2E)-和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亞乙基]-N-[4-(二氟甲氧基)苯基]肼甲醯胺(從CN 101715774 A得知)(CAS 1232543-85-9);3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯基-環丙烷甲酸酯(從CN 103524422 A得知)(CAS 1542271-46-4);(4aS)-7-氯-2,5-二氫-2-[[(甲氧羰基)[4-[(三氟甲基)硫基]苯基]胺基]羰基]茚并[1,2-e][1,3,4]㗁二𠯤-4a(3H)-甲酸甲酯(從CN 102391261 A得知)(CAS 1370358-69-2);6-去氧基-3-O-乙基-2,4-二-O-甲基-1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]胺甲酸酯]-α-L-哌喃甘露糖(從US 2014/0275503 A1得知)(CAS 1181213-14-8);8-(2-環丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基嗒𠯤-3-基)-3-氮雜雙環[3.2.1]辛烷(CAS 1253850-56-4)、(8-反側)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-嗒𠯤-3-基)-3-氮雜-雙環[3.2.1]辛烷(CAS 933798-27-7)、(8-同側)-8-(2-環丙基甲氧基-4-三氟甲基-苯氧基)-3-(6-三氟甲基-嗒𠯤-3-基)-3-氮雜雙環[3.2.1]辛烷(從WO 2007040280 A1、WO 2007040282 A1得知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫基]丙醯胺(從WO 2015/058021 A1、WO 2015/058028 A1得知)(CAS 1477919-27-9)和N-[4-(胺基硫酮基甲基)-2-甲基-6-[(甲胺基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲醯胺(從CN 103265527 A得知)(CAS 1452877-50-7)、5-(1,3-二㗁烷-2-基)-4-[[4-(三氟甲基)苯基]甲氧基]-嘧啶(從WO 2013/115391 A1得知)(CAS 1449021-97-9)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮雜螺[4.5]癸烷-2,4-二酮(從WO 2014/187846 A1得知)(CAS 1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-側氧-1,8-二氮雜螺[4.5]癸-3-烯-4-基-碳酸乙酯(得知WO 2010/066780 A1、WO 2011151146 A1得知)(CAS 1229023-00-0)、4-[(5S)-5-(3,5-二氯-4-氟苯基)-4,5-二氫-5-(三氟甲基)-3-異㗁唑基]-N-[(4R)-2-乙基-3-側氧-4異㗁唑啶基]-2-甲基-苯甲醯胺 (得知WO 2011/067272, WO2013/050302得知) (CAS 1309959-62-3)。
殺真菌劑
在本文中以彼等的俗名指定之活性成分為已知且描述於(例如)“殺蟲劑手冊(The Pesticide Manual”第16版, British Crop Protection Council 2012)中或可在網際網路中搜尋(例如http://www.alanwood.net/Pesticide)。
若彼等的官能基能夠的話,則類別(1)至(15)之所有殺真菌混合伴體可視需要地與適當鹼或酸形成鹽。若果適用,類別(1)至(15)之所有命名的混合伴體包括互變異構物形式。
1) 麥角固醇生物合成之抑制劑,例如(1.001) 環克座(cyproconazole)、(1.002) 待克利(difenoconazole)、(1.003)依普座(epoxiconazole)、(1.004) 環醯菌胺(fenhexamid)、(1.005)苯鏽啶(fenpropidin)、(1.006) 芬普福(fenpropimorph)、(1.007) 胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009) 護汰芬(flutriafole)、(1.010) 依滅列(imazalil)、(1.011) 依滅列硫酸鹽、(1.012) 種菌唑(ipconazole)、(1.013)滅特座(metconazole)、(1.014) 邁克尼(myclobutanil)、(1.015) 巴克素(paclobutrazol)、(1.016) 撲克拉(prochloraz)、((1.017)普克利(propiconazole)、(1.018) 丙硫菌唑(prothioconazole)、(1.019) 啶菌㗁唑(pyrisoxazole)、(1.020) 葚孢菌素(spiroxamine)、(1.021) 得克利(tebuconazole)、(1.022) 四克利(tetraconazole)、(1.023) 三泰隆(triadimenol)、(1.024) 三得芬(tridemorph)、(1.025) 滅菌唑(triticonazole)、(1.026)(1R,2S,5S)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.027)(1S,2R,5R)-5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.028)(2R)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.029)(2R)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031)(2S)-2-(1-氯環丙基)-4-[(1R)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032)(2S)-2-(1-氯環丙基)-4-[(1S)-2,2-二氯環丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-㗁唑-4-基](吡啶-3-基)甲醇、(1.035)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-㗁唑-4-基](吡啶-3-基)甲醇、(1.036) [3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-㗁唑-4-基](吡啶-3-基)甲醇、(1.037) 1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧五環烷-2-基}甲基)-1H-1,2,4-三唑、(1.038) 1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧五環烷-2-基}甲基)-1H-1,2,4-三唑、(1.039) 硫氰酸1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑-5-基酯、(1.040) 1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑-5-基 硫氰酸酯、(1.041) 1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑-5-基 硫氰酸酯、(1.042) 2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.043) 2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.044) 2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.045) 2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.046) 2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.047) 2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.048) 2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.049) 2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.050) 2-[1-(2,4-二氯苯基)-5-羥基-2,6,6-三甲基庚-4-基]-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.051) 2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052) 2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053) 2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054) 2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055) 2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.056) 2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.057) 2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.058) 2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-2,4-二氫-3H-1,2,4-三唑-3-硫酮、(1.059) 5-(4-氯苯甲基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)環戊醇、(1.060) 5-(烯丙硫基(allylsulfanyl))-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑、(1.061) 5-(烯丙硫基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑、(1.062) 5-(烯丙硫基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)氧𠰂-2-基]甲基}-1H-1,2,4-三唑、(1.063) N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]氫硫基(sulfanyl)}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.064) N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]氫硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.065) N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]氫硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.066) N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]氫硫基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.067) N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)氫硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.068) N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)氫硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.069) N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)氫硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.070) N'-(2,5-二甲基-4-{3-[(五氟乙基)氫硫基]苯氧基}苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.071) N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.072) N'-(4-{[3-(二氟甲氧基)苯基]氫硫基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.073) N'-(4-{3-[(二氟甲基)氫硫基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亞胺基甲醯胺、(1.074) N'-[5-溴-6-(2,3-二氫-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亞胺基甲醯胺、(1.075) N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亞胺基甲醯胺、(1.076) N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.077) N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.078) N'-{5-溴-6-[(順-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.079) N'-{5-溴-6-[反-4-異丙基環己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.080) N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亞胺基甲醯胺、(1.081) 美芬三康唑(Mefentrifluconazole)、(1.082) 伊芬三康唑(Ipfentrifluconazole)。
2) 於複合物I或II的呼吸鏈之抑制劑,例如(2.001) 苯并烯氟菌唑(benzovindiflupyr)、(2.002) 必殺芬(bixafen)、(2.003) 白克列(boscalid)、(2.004) 萎銹靈(carboxin)、(2.005) 氟吡菌醯胺(fluopyram)、(2.006) 福多寧(flutolanil)、(2.007) 氟唑菌醯胺(fluxapyroxad)、(2.008) 福拉比(furametpyr)、(2.009) 異丙噻菌胺(Isofetamid)、(2.010) 吡唑萘菌胺(isopyrazam)(反側-表異構物之鏡像異構物1R,4S,9S)、(2.011) 吡唑萘菌胺(反側-表異構物之鏡像異構物1S,4R,9R)、(2.012) 吡唑萘菌胺(反側-表異構物之消旋物1RS,4SR,9SR)、(2.013) 吡唑萘菌胺(同側-表異構物之消旋物1RS,4SR,9RS和反側-表異構物之消旋物1RS,4SR,9SR的混合物)、(2.014) 吡唑萘菌胺(同側-表異構物之鏡像異構物1R,4S,9R)、(2.015) 吡唑萘菌胺(同側-表異構物之鏡像異構物1S,4R,9S)、(2.016) 吡唑萘菌胺(同側-表異構物消旋物之1RS,4SR,9RS)、(2.017) 氟唑菌苯胺(penflufen)、(2.018) 吡噻菌胺(penthiopyrad)、(2.019) 吡福密芬(pydiflumetofen)、(2.020) 必拉氟密(Pyraziflumid)、(2.021) 環丙吡菌胺(sedaxane)、(2.022) 1,3-二甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-甲醯胺、(2.023) 1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.024) 1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.025) 1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)聯苯基-2-基]-1H-吡唑-4-甲醯胺、(2.026) 2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)苯甲醯胺、(2.027) 3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1H-吡唑-4-甲醯胺、(2.028) 3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.029) 3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1H-吡唑-4-甲醯胺、(2.030) 3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲醯胺、(2.031) 3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲醯胺、(2.032) 3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氫-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲醯胺、(2.033) 5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034) N-(2-環戊基-5-氟苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.035) N-(2-三級-丁基-5-甲基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.036) N-(2-三級-丁基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.037) N-(5-氯-2-乙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.038) N-(5-氯-2-異丙基苯甲基)-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.039) N-[(1R,4S)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-亞甲基萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.040) N-[(1S,4R)-9-(二氯亞甲基)-1,2,3,4-四氫-1,4-亞甲基萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.041) N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.042) N-[2-氯-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.043) N-[3-氯-2-氟-6-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.044) N-[5-氯-2-(三氟甲基)苯甲基]-N-環丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.045) N-環丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苯甲基]-1H-吡唑-4-甲醯胺、(2.046) N-環丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.047) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基-5-甲基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.048) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-硫代甲醯胺(carbothioamide)、(2.049) N-環丙基-3-(二氟甲基)-5-氟-N-(2-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.050) N-環丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-異丙基苯甲基)-1-甲基-1H-吡唑-4-甲醯胺、(2.051) N-環丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.052) N-環丙基-3-(二氟甲基)-N-(2-乙基-5-氟苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.053) N-環丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苯甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.054) N-環丙基-N-(2-環丙基-5-氟苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.055) N-環丙基-N-(2-環丙基-5-甲基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺、(2.056) N-環丙基-N-(2-環丙基苯甲基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲醯胺。
3) 於複合物III的呼吸鏈之抑制劑,例如(3.001) 辛唑嘧菌胺(ametoctradin)、(3.002) 安美速(amisulbrom)、(3.003) 亞托敏(azoxystrobin)、(3.004) 甲香菌酯(coumethoxystrobin)、(3.005) 丁香菌酯(coumoxystrobin)、(3.006) 賽座滅(cyazofamid)、(3.007) 醚菌胺(dimoxystrobin)、(3.008) 烯肟菌酯(enoxastrobin)、(3.009) 凡殺同(famoxadone)、(3.010) 咪唑菌酮(fenamidone)、(3.011) 氟菌蟎酯(flufenoxystrobin)、(3.012) 氟嘧菌酯(fuoxastrobin)、(3.013) 克收欣(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015) 肟醚菌胺(orysastrobin)、(3.016) 啶氧菌酯(picoxystrobin)、(3.017) 百克敏(pyraclostrobin)、(3.018) 唑胺菌酯(pyrametostrobin)、(3.0019) 唑菌酯(pyraoxystrobin)、(3.020) 三氟敏(trifloxystrobin)、(3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亞乙基]胺基}氧基)甲基]苯基}-2-(甲氧基亞胺基)-N-甲基乙醯胺、(3.022)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.023)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.024)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.025)(3S,6S,7R,8R)-8-苯甲基-3-[({3-[(異丁醯氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)胺基]-6-甲基-4,9-二側氧基-1,5-二氧雜環壬烷(dioxonan)-7-基 2-甲基丙酸酯、(3.026) 2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙醯胺、(3.027) N-(3-乙基-3,5,5-三甲基環己基)-3-甲醯胺基-2-羥基苯甲醯胺、(3.028)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亞胺基)-N,3-二甲基戊-3-烯醯胺、(3.029) {5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苯甲基}胺甲酸甲酯。
4) 有絲分裂及細胞分裂之抑制劑,例如(4.001) 多菌靈(carbendazim)、(4.002) 乙黴威(diethofencarb)、(4.003) 噻唑菌胺(ethaboxam)、(4.004) 氟吡菌胺(fluopicolide)、(4.005) 賓克隆(pencycuron)、(4.006) 腐絕(thiabendazole)、(4.007) 甲基多保淨(thiophanate-methyl)、(4.008) 座賽胺(zoxamide)、(4.009) 3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基嗒𠯤、(4.010) 3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基嗒𠯤、(4.011) 3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)嗒𠯤、(4.012) 4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013) 4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014) 4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015) 4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016) 4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017) 4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018) 4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019) 4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020) 4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021) 4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022) 4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基嗒𠯤、(4.023) N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024) N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025) N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5) 能夠具有多位作用之化合物,例如(5.001) 波爾多(bordeaux)混合物、(5.002) 四氯丹(captafol)、(5.003) 蓋普丹(captan)、(5.004) 四氯異苯腈(chlorothalonil)、(5.005) 氫氧化銅、(5.006) 環烷酸銅、(5.007) 氧化銅、(5.008) 氯氧化銅、(5.009) 硫酸銅(2+)、(5.010) 腈硫醌(dithianon)、(5.011)多寧(dodine)、(5.012) 福爾培(folpet)、(5.013) 鋅錳乃浦(mancozeb)、(5.014) 錳乃浦(maneb)、(5.015) 免得爛(metiram)、(5.016) 免得爛鋅(metiram zinc)、(5.017) 快得寧(oxine-copper)、(5.018) 甲基鋅乃浦(propineb)、(5.019) 硫和包括多硫化鈣之硫製劑、(5.020) 得恩地(thiram)、(5.021) 鋅乃浦(zineb)、(5.022) 益穗(ziram)、(5.023) 6-乙基-5,7-二側氧基-6,7-二氫-5H-吡咯并[3',4':5,6][1,4]二硫雜環己并(dithiino)[2,3-c][1,2]噻唑-3-甲腈。
6) 能夠誘發宿主防禦之化合物,例如(6.001) 阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、(6.002) 異噻菌胺(isotianil)、(6.003) 撲殺熱(probenazole)、(6.004) 噻醯菌胺(tiadinil)。
7) 胺基酸及/或蛋白質生物合成之抑制劑,例如(7.001) 賽普洛(cyprodinil)、(7.002) 嘉賜黴素(kasugamycin)、(7.003) 嘉賜黴素鹽酸鹽水合物、(7.004) 氧四環素(oxytetracycline)、(7.005) 派美尼(pyrimethanil)、(7.006) 3-(5-氟-3,3,4,4-四甲基-3,4-二氫異喹啉-1-基)喹啉。
8) ATP產生之抑制劑,例如 (8.001) 矽噻菌胺。
9) 細胞壁合成之抑制劑,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002) 達滅芬(dimethomorph)、(9.003) 氟嗎啉(flumorph)、(9.004) 丙森鋅(iprovalicarb)、(9.005) 雙炔醯菌胺(mandipropamid)、(9.006) 丁吡嗎啉(pyrimorph)、(9.007) 纈菌胺(valifenalate)、(9.008)(2E)-3-(4-三級-丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎福林-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-三級-丁基苯基)-3-(2-氯吡啶-4-基)-1-(嗎福林-4-基)丙-2-烯-1-酮。
10) 脂質及膜合成之抑制劑,例如(10.001)普拔克(propamocarb)、(10.002)普拔克鹽酸鹽、(10.003) 脫克松(tolclofos-methyl)。
11) 黑色素生物合成之抑制劑,例如(11.001)三環唑(tricyclazole),(11.002) {3-甲基-1-[(4-甲基苯甲醯)胺基]丁-2-基}胺基甲酸2,2,2-三氟乙酯。
12) 核酸合成之抑制劑,例如(12.001) 本達樂(benalaxyl)、(12.002) 本達樂-M(克拉昔(kiralaxyl))、(12.003) 滅達樂(metalaxyl)、(12.004) 滅達樂-M(滅芬散(mefenoxam))。
13) 訊號轉導之抑制劑,例如(13.001) 護汰寧(fludioxonil)、(13.002) 依普同(iprodione)、(13.003) 撲滅寧(procymidone)、(13.004) 丙氧喹啉(proquinazid)、(13.005) 快諾芬(quinoxyfen)、(13.006) 免克寧(vinclozolin)。
14) 能夠充當非偶合劑之化合物,例如(14.001) 扶吉胺(fluazinam)、(14.002) 敵蟎普(meptyldinocap)。
15) 其他化合物,例如(15.001) 脫落酸(Abscisic acid)、(15.002)苯噻硫氰(benthiazole)、(15.003)苯噻𠯤(bethoxazin)、(15.004) 卡巴西黴素(capsimycin)、(15.005) 香芹酮(carvone)、(15.006) 滅蟎猛(chinomethionat)、(15.007)硫雜靈(cufraneb)、(15.008) 環氟菌胺(cyflufenamid)、(15.009) 克絕(cymoxanil)、(15.010) 環丙磺醯胺(cyprosulfamide)、(15.011) 氟噻菌淨(flutianil)、(15.012) 福賽得(fosetyl-aluminium)、(15.013) 福賽得-鈣(fosetyl-calcium)、(15.014) 福賽得-鈉(fosetyl-sodium)、(15.015) 異硫氰酸甲酯、(15.016) 滅芬農(metrafenone)、(15.017) 米多黴素(mildiomycin)、(15.018) 納他黴素(natamycin)、(15.019) 二甲基二硫胺基甲酸鎳、(15.020) 酞菌酯(nitrothal-isopropyl)、(15.021) 歐莫克(oxamocarb)、(15.022) 氟噻唑吡乙酮(Oxathiapiprolin)、(15.023) 歐芬英(oxyfenthiin)、(15.024) 五氯酚(pentachlorophenol)及鹽、(15.025) 亞磷酸及其鹽、(15.026) 普拔克-乙膦酸鹽(propamocarb-fosetylate)、(15.027) 比芬酮(pyriofenone)(克芬酮(chlazafenone))、(15.028) 特布洛昆(tebufloquin)、(15.029) 克枯爛(tecloftalam)、(15.030) 甲磺菌胺(tolnifanide)、(15.031) 1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氫-1,2-㗁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.032) 1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氫-1,2-㗁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.033) 2-(6-苯甲基吡啶-2-基)喹唑啉、(15.034) 2,6-二甲基-1H,5H-[1,4]二硫雜環己并(dithiino)[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.035) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-㗁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.036) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-㗁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.037) 2-[3,5-雙(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氫-1,2-㗁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.038) 2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.039) 甲烷磺酸2-{(5R)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-㗁唑-5-基}-3-氯苯基酯、(15.040) 甲烷磺酸2-{(5S)-3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-㗁唑-5-基}-3-氯苯基酯、(15.041) 2-{2-[(7,8-二氟-2-甲基喹啉-3-基)氧基]-6-氟苯基}丙-2-醇、(15.042) 2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043) 甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-㗁唑-5-基}-3-氯苯基酯、(15.044) 甲烷磺酸2-{3-[2-(1-{[3,5-雙(二氟甲基)-1H-吡唑-1-基]乙醯基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氫-1,2-㗁唑-5-基}苯基酯、(15.045) 2-苯基酚及鹽、(15.046) 3-(4,4,5-三氟-3,3-二甲基-3,4-二氫異喹啉-1-基)喹啉、(15.047) 3-(4,4-二氟-3,3-二甲基-3,4-二氫異喹啉-1-基)喹啉、(15.048) 4-胺基-5-氟嘧啶-2-醇(互變異構形式:4-胺基-5-氟嘧啶-2(1H)-酮)、(15.049) 4-側氧基-4-[(2-苯基乙基)胺基]丁酸、(15.050) 5-胺基-1,3,4-噻二唑-2-硫醇、(15.051) 5-氯-N'-苯基-N'-(丙-2-炔-1-基噻吩-2-磺酸基(sulfono)醯肼、(15.052) 5-氟-2-[(4-氟苯甲基)氧基]嘧啶-4-胺、(15.053) 5-氟-2-[(4-甲基苯甲基)氧基]嘧啶-4-胺、(15.054) 9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氫-1,4-苯并氧雜氮呯、(15.055) {6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺甲酸丁-3-炔-1-基酯、(15.056) (2Z)-3-胺基-2-氰基-3-苯基丙烯酸乙酯、(15.057) 啡𠯤-1-甲酸、(15.058) 3,4,5-三羥基苯甲酸丙酯、(15.059) 喹啉-8-醇、(15.060) 喹啉-8-醇硫酸鹽(2:1)、(15.061) {6-[({[(1-甲基-1H-四唑-5-基)(苯基)亞甲基]胺基}氧基)甲基]吡啶-2-基}胺甲酸三級-丁酯、(15.062) 5-氟-4-亞胺基-3-甲基-1-[(4-甲基苯基)磺醯基]-3,4-二氫嘧啶-2(1H)-酮。
作為混合組分之生物殺蟲劑
式(I)化合物可與生物殺蟲劑組合。
生物殺蟲劑特別是包含細菌、真菌、酵母、植物萃取物和由微生物形成的產物,包括蛋白質和次級代謝物。
生物殺蟲劑包含細菌諸如形成孢子的細菌、定殖根的細菌和充當生物殺昆蟲劑、殺真菌劑或殺線蟲劑之細菌。
該等用作或可用作生物殺蟲劑之細菌的實例為:
芽孢枯草桿菌(Bacillus amyloliquefaciens),菌株FZB42(DSM 231179)、或蠟狀芽孢桿菌(Bacillus cereus),特別是蠟狀芽孢桿菌(B. cereus)菌株CNCM I-1562或堅固芽孢桿菌(Bacillus firmus),菌株I-1582(登錄號CNCM I-1582)或短小芽孢桿菌(Bacillus pumilus),特別是菌株GB34(登錄號ATCC 700814)及菌株QST2808(登錄號NRRL B-30087)、或枯草桿菌(Bacillus subtilis),特別是菌株GB03(登錄號ATCC SD-1397)、或枯草桿菌(Bacillus subtilis)菌株QST713(登錄號NRRL B-21661)或枯草桿菌(Bacillus subtilis)菌株OST 30002(登錄號NRRL B-50421) 蘇力菌(Bacillus thuringiensis),特別是蘇力菌以色列亞種(B. thuringiensis subspecies israelensis)(血清型 H-14)、菌株AM65-52(登錄號ATCC 1276)、或蘇力菌鮎澤亞種(B. thuringiensis subsp. aizawai),特別是菌株ABTS-1857(SD-1372)、或蘇力菌庫斯克亞種(B. thuringiensis subsp. kurstaki strain) 菌株HD-1、或蘇力菌擬步行蟲亞種(B. thuringiensis subsp. tenebrionis)菌株NB 176(SD-5428)、穿刺巴氏桿菌(Pasteuria penetrans)、巴氏桿菌屬(Pasteuria spp.)(腎狀腎形線蟲(Rotylenchulus reniformis)線蟲)-PR3(登錄號ATCC SD-5834)、細黃鏈黴菌(Streptomyces microflavus)菌株AQ6121(= QRD 31.013、NRRL B-50550)、鮮黃鏈黴菌(Streptomyces galbus)菌株AQ 6047(登錄號NRRL 30232)。
用作或可用作生物殺蟲劑之真菌和酵母的實例為:
巴氏蠶白僵菌(Beauveria bassiana),特別是菌株ATCC 74040、微坦盾殼黴(Coniothyrium minitans),特別是CON/M/91-8菌株(登錄號DSM-9660)、輪枝菌屬(Lecanicillium spp.),特別是菌株HRO LEC 12、臘蚧輪枝菌(Lecanicillium lecanii,以前稱為臘蚧輪刺孢菌(Verticillium lecanii)),特別是菌株KV01、黑殭菌(Metarhizium anisopliae),特別是菌株F52 (DSM3884/ ATCC 90448)、梅奇酵母(Metschnikowia fructicola),特別是菌株NRRL Y-30752、玫煙色擬青黴菌(Paecilomyces fumosoroseus)、(現:玫煙色棒束孢(Isaria fumosorosea)),特別是菌株IFPC 200613、或菌株Apopka 97 (登錄號ATCC 20874)、淡紫擬青黴菌(Paecilomyces lilacinus),特別是菌株淡紫擬青黴菌251 (AGAL 89/030550)、黃籃狀菌(Talaromyces flavus),特別是菌株V117b、深綠木黴(Trichoderma atroviride),特別是菌株SC1(登錄號CBS 122089)、哈茨木黴菌(Trichoderma harzianum),特別是哈茨木黴菌T39(登錄號CNCM I-952)。
用作或可用作生物殺蟲劑之病毒的實例為:
茶姬捲葉蛾(Adoxophyes orana)(夏季水果捲葉蛾)顆粒增殖病毒(GV)、蘋果蠹蛾(Cydia pomonella)(蘋果捲葉蛾)顆粒增殖病毒(GV)、蕃茄夜蛾(Helicoverpa armigera,棉鈴蟲)核多角體病毒(NPV)、甜菜葉蛾(Spodoptera exigua)(甜菜夜蛾)mNPV、草地夜蛾(Spodoptera frugiperda)(秋夜蛾) mNPV、海灰翅夜蛾(Spodoptera littoralis)(非洲棉葉蟲)NPV。
亦包括者為以‘接種物‘加至植物或植物部份或植物器官且由於彼等的特定性質而促進植物生長及健康的細菌和真菌。可提及之實例為:
農桿菌屬(Agrobacterium spp.)、莖瘤固氮根瘤菌(Azorhizobium caulinodans)、固氮螺旋菌屬(Azospirillum spp.)、固氮菌屬(Azotobacter spp.)、慢生根瘤菌屬(Bradyrhizobium spp.)、伯克氏菌屬(Burkholderia spp.),特別是洋蔥伯克氏菌(Burkholderia cepacia)(以前稱為蔥頭假單孢菌(Pseudomonas cepacia))、巨孢囊黴屬(Gigaspora spp.)或單孢巨孢囊霉(Gigaspora monosporum)、球囊黴屬(Glomus spp.)、蠟蘑屬(Laccaria spp.)、布氏乳酸桿菌(Lactobacillus buchneri)、類球囊黴屬(Paraglomus spp.)、彩色豆馬勃(Pisolithus tinctorus)、假單孢菌屬(Pseudomonas spp.)、根瘤菌屬(Rhizobium spp.),特別是三葉草根瘤菌(Rhizobium trifolii)、根鬚腹菌屬(Rhizopogon spp.)、硬皮馬勃屬(Scleroderma spp.)、黏蓋菌屬(Suillus spp.)、鏈黴菌屬(Streptomyces spp.)。
用作或可用作生物殺蟲劑之植物萃取物和由微生物形成的產物(包括蛋白質和次級代謝物)的實例為:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、黑肉桂 (Cassia nigricans)、苦皮藤(Celastrus angulatus)、土荊芥(Chenopodium anthelminticum)、甲殼素(chitin)、Armour-Zen、歐洲鱗毛蕨(Dryopteris filix-mas)、問荊(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(藜麥皂素萃取物)、除蟲菊/除蟲菊酯、苦木(Quassia amara)、櫟(Quercus)、皂樹皮(Quillaja)、Regalia、〝Requiem™ 殺昆蟲劑〞、魚藤酮、魚尼丁(ryania)/藍尼定(ryanodine)、康福利草(Symphytum officinale)、菊蒿(Tanacetum vulgare)、百里酚、Triact 70;TriCon、旱金蓮(Tropaeulum majus)、異株蕁麻(Urtica dioica)、藜蘆鹼(Veratrin)、槲寄生(Viscum album)、十字花科萃取物,特別是油菜籽粉或芥末粉。
作為混合組分的安全劑
式(I)化合物可與安全劑(例如解草酮(benoxacor)、解毒喹(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、環丙磺醯胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole)(-乙基)、解草啶(fenclorim)、解草胺(flurazole)、肟草安(fluxofenim)、解草㗁唑(furilazole)、異地芬(isoxadifen)(-乙基)、吡唑解草酯(mefenpyr)(-二乙基)、萘二甲酸酐、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基胺甲醯基)胺基]苯基}磺醯基)苯甲醯胺(CAS 129531-12-0)、4-(二氯乙醯基)-1-氧雜-4-氮雜螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙醯基)-1,3-㗁唑啶(CAS 52836-31-4)組合。
植物和植物部份
整株植物和植物部份可根據本發明處理。在此,植物係應理解為意指整株植物和植物部份,諸如所要及非所要野生植物或作物植物(包括天然存在的作物),例如穀類(小麥、稻米、黑小麥、大麥、黑麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、蕃茄、胡椒、黃瓜、甜瓜、胡蘿蔔、西瓜、洋蔥、萵苣、菠菜、韭菜、豆子、甘藍(例如包心菜)和其他蔬菜種類、棉花、煙草、油菜籽,以及為果實植物(具有果實蘋果、梨、柑橘和葡萄藤)。作物植物可為藉由習知的育種及優化方法、或藉由生物技術和基因工程方法、或該等方法之組合而可獲得的植物,包括基因轉殖植物且包括可受到或未受到品種財產權(varietal property right)保護的植物變種。植物係應理解為意指所有的發育階段,諸如種子、幼苗、幼(未成熟)植物到成熟植物。植物部份係應理解為意指植物在地上與地下的所有部份及組織,諸如芽、葉、花和根,給定的實例為葉、針葉、柄、莖、花、果實體、果實和種子,以及根、塊莖和根莖。植物的部份亦包括收成植物或收成植物部份及營養和生殖繁殖物質,例如幼苗、塊莖、根莖、插枝和種子。
根據本發明用式(I)化合物處理植物和植物部份係以習知處理方法(例如藉由浸漬、噴灑、蒸發、噴霧、散播、塗上、注射)直接進行或藉由使化合物作用於其周圍、環境或貯藏空間進行,及在繁殖材料的情況下,特別是在種子的情況下,亦藉由施用一或多層塗層進行。
如上文已提及者,根據本發明可能處理整株植物或其部份。在一較佳實施態樣中,處理野生植物種類及植物栽培品種、或彼等藉由習知的生物育種方法(諸如交配或原生質體融合)所獲得者,以及其部份。在另一較佳實施態樣中,處理藉由基因工程方法(若適當時,與習知的方法組合)所獲得的基因轉殖植物和植物栽培品種(基改生物)及其部份。術語“部份”或“植物的部份”或“植物部份”已於上文解釋。特佳者為使用本發明處理個別市售習知的栽培品種或彼等使用中的植物。植物栽培品種係理解為意指具有新性質(“性狀”)且已藉由習知的育種、藉由突變或藉由重組DNA技術而獲得的植物。彼等可為栽培品種、變種、生物型或基因型。
基因轉殖植物、種子處理和整合事件
欲根據本發明較佳處理之基因轉殖植物或植物栽培品種(藉由基因工程獲得者)包括所有透過基因改造而接受賦與這些植物特別有利的有用性質("性狀")之遺傳物質的植物。該等性質的實例為較佳的植物生長、對高或低溫之耐受性增加、對乾旱或水位或土壤鹽度的耐受性增加、開花性能提高,較易收成、加速熟成,產量較高、收穫產物之較高品質及/或較高營養價值、收穫產物之較佳儲存壽命及/或加工性。該等性質之其他且特別強調的實例為由於(例如)植物內所形成之毒素(特別是彼等由來自蘇力菌(Bacillus thuringiensis)之遺傳物質(例如由基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF以及其組合)於植物內所形成之毒素),植物對抗動物和微生物害蟲(諸如對抗昆蟲、蜘蛛綱動物、線蟲、蟎、蛞蝓和蝸牛)之抗性增加,此外由於(例如)後天性系統抗性(systemic acquired resistance)(SAR)、系統素(systemin)、植物防禦素、激發子(elicitors)以及抗性基因和對應表現之蛋白質和毒素,植物對抗植物病原性真菌、細菌及/或病毒之抗性增加、以及植物對某些除草活性化合物(例如咪唑啉酮、磺醯脲、嘉磷塞(glyphosate)或草胺膦(phosphinothricin))(例如"PAT"基因)之耐受性增加。賦予討論中的所要性狀之基因亦可彼此組合存在於基因轉殖植物中。所提及之基因轉殖植物的實例包括重要作物,諸如穀類(小麥、稻米、黑小麥、大麥、黑麥、燕麥)、玉米、大豆、馬鈴薯、甜菜、甘蔗、番茄、豌豆及其他類型蔬菜、棉花、菸草、油菜籽以及果實植物(具有蘋果、梨、柑橘與葡萄),且特別強調者為玉米、大豆、小麥、稻米、馬鈴薯、棉花、甘蔗、煙草和油菜籽。特別強調的性狀為植物對昆蟲、蜘蛛綱動物、線蟲及蛞蝓和蝸牛之抗性增加。
作物保護 - 處理類型
以式(I)化合物處理植物和植物部份係使用習知的處理方法(例如藉由浸漬、噴灑、霧化、灌溉、蒸發、撒粉、噴霧、撒佈、發泡、噴塗、散佈、注射、灑水(澆灌)、滴液灌溉)直接進行或藉由作用在其周圍、棲息處或貯藏空間來進行,及在繁殖物質之情形下,特別是在種子之情形下,此外呈用於乾式種子處理之粉末、用於液態種子處理之溶液、用於漿液處理之水溶性粉末、藉由包覆、藉由塗上一或多層等等來進行。此外可能以超低體積法施用式(I)化合物,或以施用形式或式(I)化合物本身注入土壤中。
植物之較佳直接處理為葉施用,亦即將式(I)化合物施用於葉子,其中處理頻率及施用率應根據討論中的害蟲之感染程度來調整。
在系統性活性化合物的情況下,式(I)化合物亦經由根系統進入植物。接著藉由式(I)化合物作用於植物棲息處來處理植物。此可例如藉由澆灌或藉由混合至土壤或營養液中達成,即以液體形式的式(I)化合物浸透植物之所在地(例如,土壤或水耕系統),或藉由土壤施用,亦即根據本發明之式(I)化合物以固體形式(例如,呈粒劑形式)引入植物之所在地達成,或藉由滴灌施用(通常也稱為“化學灌溉“),即在某段時間內從地表或地下滴灌管將根據本發明之式(I)化合物與不同量的水一起液體施用在植物附近的界定位置。在水稻作物的情況下,此亦可藉由將式(I)化合物以固體施用形式(例如,呈粒劑)計量供給至水稻田中而達成。
種子處理
藉由處理植物種子來控制動物害蟲是早已知道的且為不斷改良之標的。然而,種子的處理引起一系列總是無法以令人滿意的方式解決之問題。因此,希望開發出在貯藏期間、在播種之後或在植物出苗之後免除或至少顯著地減少額外施用殺蟲劑以保護種子及發芽植物之方法。此外希望將所使用的活性化合物之量最適化,以便對種子及發芽植物提供最佳保護而免於動物害蟲的攻擊,但是所使用的活性化合物不傷害植物本身。特別地,用於處理種子之方法亦應考慮到抗害蟲性或耐害蟲性基因轉殖植物的固有殺昆蟲或殺線蟲性質,以便以最少用量的殺蟲劑達成對種子及亦對發芽植物的最佳保護。
本發明因此特別亦關於一種藉由以式(I)化合物中之一者處理種子來保護種子及發芽植物免於害蟲攻擊之方法。用於保護種子及發芽植物免於害蟲攻擊之根據本發明方法此外包含一種其中以式(I)化合物及混合組分以一次操作同時處理或相繼處理種子之方法。亦包含一種其中於不同的時間以式(I)化合物及混合組分處理種子之方法。
本發明同樣關於式(I)化合物用於處理種子以保護種子及所得植物免於動物害蟲之用途。
此外,本發明關於已用根據本發明之式(I)化合物處理以使提供防止動物害蟲之種子。本發明亦關於已同時用式(I)化合物及混合組分處理之種子。本發明此外關於已在不同時間用式(I)化合物及混合組分處理之種子。在種子已於不同時間用式(I)化合物及混合組分處理之情形下,個別物質可存在於種子上之不同層中。在此,包含式(I)化合物及混合組分的層可視需要地以中間層分開。本發明亦有關其中式(I)化合物及混合組分已施用作為塗層的組成或作為除了塗層以外的另一層或更多層之種子。
此外,本發明關於在以式(I)化合物處理之後進行塗膜方法以防止在種子上的灰塵磨耗之種子。
系統性作用的式(I)化合物所碰到的優點之一為藉由處理種子,不只防止種子本身的動物害蟲,並亦在出苗之後,防止由其所產生之植物的動物害蟲。以此方式,可免除在播種時或不久之後對作物的立即處理。
藉由以式(I)化合物處理種子所必須考慮的另一優點為可提高經處理種子之發芽及出苗。
同樣被視為優點的是式(I)化合物特別也可用於基因轉殖種子。
此外,式(I)化合物可與傳訊技術(signalling technology)之組成物或化合物組合使用,其導致共生體(諸如(例如)根瘤菌、菌根及/或內生性細菌或真菌)更好的選殖,及/或導致最適化固氮作用。
式(I)化合物適合於保護在農業、溫室、林業或園藝中使用的任何植物品種之種子。特別地,此以下列種子的形式取得:穀類(例如小麥、大麥、黑麥、小米和燕麥)、玉米、棉花、大豆、稻米、馬鈴薯、向日葵、咖啡、菸草、油菜、油菜籽、甜菜(例如糖用甜菜和飼料甜菜)、花生、蔬菜類(例如番茄、黃瓜、豆子、十字花科蔬菜、洋蔥和萵苣)、果實植物、草皮及觀賞植物。穀類(諸如小麥、大麥、黑麥和燕麥)、玉米、大豆、棉花、油菜、油菜籽、蔬菜和稻米之種子的處理是特別重要的。
如上文已提及者,以式(I)化合物處理基因轉殖種子也是特別重要的。此以通常包含至少一種控制特別是具有殺昆蟲及/或殺線蟲性質之多肽的表現之異源基因的植物種子的形式取得。基因轉殖種子中的異源基因可源自諸如下列之微生物:桿菌(Bacillus)、根瘤菌(Rhizobium)、假單胞菌(Pseudomonas)、沙雷氏菌(Serratia)、木黴菌(Trichoderma)、棒狀桿菌(Clavibacter)、球囊黴(Glomus)、或黏帚黴菌(Gliocladium)。本發明係特別適合於處理包含至少一種源自桿菌屬之異源基因的基因轉殖種子。特佳的是源自蘇力菌之異源基因。
在本發明的情況下,式(I)化合物係施用至種子。較佳地,該種子係以其足夠穩定以在處理過程中避免損害的狀態下來處理。通常,種子可在採收和播種之間的任何時間點處理。通常使用的種子已經從植物中分離並已去除果實的穗軸、殼、柄、表皮、毛或果肉的種子。例如,可能使用已收成、清洗且乾燥至允許儲存之水分含量的種子。或者,亦可能使用在乾燥之後已用例如水處理且接著再乾燥(例如滲調處理(priming))之種子。在水稻種子的情況下,也可能使用已經在(例如)水中浸泡至稻米胚芽之某階段(雞胸期(pigeon breast stage))以刺激發芽及更均勻的出苗之種子。
當處理種子時,通常必須以種子發芽不會受到不利影響或不傷害所得植物之方式小心選擇式(I)化合物施用至種子的量及/或另外的添加劑之量。活性化合物在某些施用率下會呈現植物毒性作用之情形下必須特別確保如此。
通常,式(I)化合物係以適合的調配物施用至種子。用於種子處理的適當調配物及方法為熟習該項技術者已知的。
式(I)化合物可轉化成習知拌種調配物,諸如溶液、乳劑、懸浮液、粉末、泡沫劑、漿液或其他塗覆組成物,以及ULV調配物。
此等調配物係以習知方式藉由將式(I)化合物與習知添加劑(諸如,例如,習知增量劑以及溶劑或稀釋劑、著色劑、潤濕劑、分散劑、乳化劑、消泡劑、防腐劑、二次增稠劑、黏著劑、赤黴素、以及水)混合而製得。
可存在於根據本發明可使用之拌種調配物中的著色劑為習用於該等目的之所有著色劑。可能使用微溶於水中的顏料,或溶於水的染料。實例包括以羅丹明B、C.I.顏料紅色112號、與C.I.溶劑紅色1號名稱得知的染料。
可存在於根據本發明可使用之拌種調配物中的有用潤濕劑為促進潤濕且習用於活性農化活性化合物之調配物的所有物質。較佳者為使用烷基萘磺酸鹽,如二異丙基-或二異丁基萘磺酸鹽。
可存在於根據本發明可使用之拌種調配物中的有用分散劑及/或乳化劑為習用於農化成分之調配物的所有非離子、陰離子和陽離子分散劑。較佳者為使用非離子或陰離子分散劑、或非離子或陰離子分散劑之混合物。適當陰離子分散劑特別包括環氧乙烷/環氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚及其磷酸化或硫酸化衍生物。適當陰離子分散劑特別是木質磺酸鹽、聚丙烯酸鹽和芳基磺酸鹽/甲醛縮合物。
可存在於根據本發明可使用之拌種調配物中的消泡劑為習用於活性農化成分之調配物的所有泡沫抑制物質。較佳者為使用聚矽氧消泡劑與硬脂酸鎂。
可存在於根據本發明可使用之拌種調配物中的防腐劑為所有為了該等目的可用於農化組成物中之物質。
可存在於根據本發明可使用之拌種調配物中的二次增稠劑為所有為了該等目的可用於農化組成物中之物質。纖維素衍生物、丙烯酸衍生物、三仙膠、改質黏土及細粉狀矽氧為較佳。
可存在於根據本發明可使用之拌種調配物中的黏著劑為可用於拌種產品之所有習用黏合劑。聚乙烯基吡咯啶酮、聚乙酸乙烯酯、聚乙烯醇及泰勒膠(tylose)可提及為較佳。
可存在於根據本發明可使用之拌種調配物中的赤黴素較佳者為赤黴素A1、A3(=赤黴酸)、A4與A7;特佳使用赤黴酸。赤黴素為已知的(參見R. Wegler "Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel", vol. 2, Springer Verlag, 1970, pp. 401-412)。
根據本發明可用的拌種調配物可直接或事先以水稀釋之後用於處理各種廣泛不同種類的種子。例如,濃縮物或以水稀釋而可自其獲得的製劑可用於拌塗穀類(諸如小麥、大麥、黑麥、燕麥和黑小麥)之種子,以及玉米、稻米、油菜籽、豌豆、豆子、棉花、向日癸、大豆和甜菜之種子,或其他各種廣泛不同的蔬菜種子。根據本發明可用的拌種調配物,或其稀釋使用形式亦可用於拌塗基因轉殖植物之種子。
關於以根據本發明可用的拌種調配物或藉由添加水而自其製備的使用形式處理種子,習知可用於拌種的所有混合單元是有用的。具體地說,拌種中的程序為以分批或連續地操作將種子放入混合器中,添加特定所要量之拌種調配物(以其原樣子或事先以水稀釋之後),及混合一切,直到調配物均勻地分佈於種子上為止。若適當的話,此接著乾燥操作。
根據本發明可用的拌種調配物之施用率可在相當寬廣的範圍內改變。施用率係受調配物中式(I)化合物的特定含量及種子所支配。式(I)化合物之施用率通常為每公斤種子介於0.001和50克之間,較佳為每公斤種子介於0.01和15克之間。
動物健康
在動物健康領域中,亦即在獸醫領域中,式(I)化合物具有對抗動物寄生蟲(特別是體外寄生蟲或體內寄生蟲)的活性。術語體內寄生蟲特別包括蠕蟲及原生動物,諸如球蟲。體外寄生蟲典型且較佳地為節肢動物,尤其是昆蟲或蟎。
在獸醫領域中,在溫血動物中具有有利的毒性的式(I)化合物適合於控制出現在動物育種和畜牧業的家畜、育種動物、動物園動物、實驗室動物、實驗動物和家養動物中的寄生蟲。彼等具有對抗所有或特定發育階段之寄生蟲的活性。
農業家畜包括(例如)哺乳動物諸如綿羊、山羊、馬、驢、駱駝、水牛、兔、馴鹿、黇鹿,且特別是牛和豬;或家禽諸如火雞、鴨、鵝、且特別是雞;或魚或甲殼動物,例如於水產養殖中,或視情況可為昆蟲,諸如蜜蜂。
家養動物包括(例如)哺乳類動物,諸如倉鼠、天竺鼠、大鼠、小鼠、絨鼠、雪貂、或特別是狗、貓;籠中鳥;爬蟲類;兩棲類和觀賞魚。
根據一特定實施態樣,式(I)化合物係投予至哺乳動物。
根據另一特定實施態樣,式(I)化合物係投予至鳥類,亦即籠中鳥且特別是家禽。
藉由使用式(I)化合物控制動物寄生蟲,意欲減少或防止病症、死亡個案和性能降低(在肉、奶、羊毛、皮革、蛋、蜂蜜等等的情況下),使得可能更經濟和更簡單地飼育動物且可達成更好的動物福利。
如本文所用關於動物健康領域之術語“控制(control)或(controlling)”意指式(I)化合物將感染該等寄生蟲的動物中之個別寄生蟲的發生率有效地減少至無害程度。更具體地說,“控制(controlling)”,如本文所用,意指式(I)化合物有效地殺死個別寄生蟲、抑制其生長、或抑制其繁殖。
節肢動物包括但不限於:
來自蝨目(Anoplurida)之目,例如,血蝨屬(Haematopinus spp.)、長齶蝨屬(Linognathus spp.)、蝨屬(Pediculus spp.)、陰蝨屬(Phtirus spp.)、牛蝨屬(Solenopotes spp.);
來自食毛目(Mallophagida)及鈍角亞目(Amblycerina)與絲角亞目(Ischnocerina)之目,例如牛羽蝨屬(Bovicola spp.)、牛仔食蟲虻屬(Damalina spp.)、貓羽蝨屬(Felicola spp.)、勒蝨屬(Lepikentron spp.)、禽羽蝨屬(Menopon spp.)、毛蝨屬(Trichodectes spp.)、毛羽蝨屬(Trimenopon spp.)、巨毛蝨屬(Trinoton spp.)、畜蝨屬(Werneckiella spp.);
來自雙翅目(Diptera)以及長角亞目(Nematocerina)與短角亞目(Brachycerina)之目,例如,斑蚊屬(Aedes spp.)、瘧蚊屬(Anopheles spp.)、黄虻屬(Atylotus spp.)、蜂蝨蠅屬(Braula spp.)、麗蠅屬(Calliphora spp.)、金蠅屬(Chrysomyia spp.)、斑虻屬(Chrysops spp.)、家蚊屬(Culex spp.)、庫蠓屬(Culicoides spp.)、真蚋屬(Eusimulium spp.)、廁蠅屬(Fannia spp.)、馬蠅屬(Gasterophilus spp.)、舌蠅屬(Glossina spp.)、血蠅屬(Haematobia spp.)、麻虻屬(Haematopota spp.)、蝨蠅屬(Hippobosca spp.)、瘤虻屬(Hybomitra spp.)、齒股蠅屬(Hydrotaea spp.)、牛蠅屬(Hypoderma spp.)、鹿蝨蠅屬(Lipoptena spp.)、綠蠅屬(Lucilia spp.)、羅蛉屬(Lutzomyia spp.)、蜱蠅屬(Melophagus spp.)、莫蠅屬(Morellia spp.)、家蠅屬(Musca spp.)、短蚋屬(Odagmia spp.)、狂蠅屬(Oestrus spp.)、菲蠓屬(Philipomyia spp.)、白蛉屬(Phlebotomus spp.)、鼻狂蠅屬(Rhinoestrus spp.)、肉蠅屬(Sarcophaga spp.)、蚋屬(Simulium spp.)、廄蠅屬(Stomoxys spp.)、牛虻屬(Tabanus spp.)、大蚊屬(Tipula spp.)、維蚋屬(Wilhelmia spp.)、污蠅屬(Wohlfahrtia spp.);
來自蚤目(Siphonapterida)之目,例如,角葉蚤屬(Ceratophyllus spp.)、櫛頭蚤屬(Ctenocephalides spp.)、蚤屬(Pulex spp.)、潛蚤屬(Tunga spp.)、鼠蚤屬(Xenopsylla spp.);
來自異翅目(Heteropterida)之目,例如,臭蟲屬(Cimex spp.)、錐蝽屬(Panstrongylus spp.)、紅獵蝽屬(Rhodnius spp.)、獵蝽屬(Triatoma spp.);以及來自蠊目(Blattarida)之目的滋擾和衛生性害蟲。
此外,在節肢動物的情況下,可以實例而非限制之方式提及下列蜱蟎亞綱:
來自蜱蟎亞綱(Acari(Acarina))之亞綱及後氣門亞目(Metastigmata)之目,例如,來自軟蜱科(Argasidae)之科如銳緣蜱屬(Argas spp.)、鈍緣蜱屬(Ornithodorus spp.)、耳蜱屬(Otobius spp.),來自硬蜱科(Ixodidae)之科如大壁蝨屬(Amblyomma spp.)、革蜱屬(Dermacentor spp.)、血蜱屬(Haemophysalis spp.)、長鬚壁蝨屬(Hyalomma spp.)、硬蜱屬(Ixodes spp.)、扇頭壁蝨屬(Rhipicephalus(牛蜱屬(Boophilus spp))、扇頭蜱屬(多宿主蜱的原始屬);來自中氣門蟎目(mesostigmata)之目如刺皮蟎屬(Dermanyssus spp.)、禽刺蟎屬(Ornithonyssus spp.)、肺刺蟎屬(Pneumonyssus spp.)、耳蟎屬(Raillietia spp.)、胸孔蟎屬(Sternostoma spp.)、小蜂蟎屬(Tropilaelaps spp.)、瓦蟎屬(Varroa spp.);來自輻蟎亞目(Actinedida)(前氣門亞目(Prostigmata))之目,例如蟎屬(Acarapis spp.)、姬螯蟎屬(Cheyletiella spp.)、毛囊蟎屬(Demodex spp.)、牦蟎屬(Listrophorus spp.)、肉蟎屬(Myobia spp.)、新恙蟎屬(Neotrombiculla spp.)、禽螯蟎屬(Ornithocheyletia spp.)、瘡蟎屬(Psorergates spp.)、恙蟎屬(Trombicula spp.);及來自粉蟎亞目(Acaridida)(無氣門亞目(Astigmata))之目,例如粉蟎屬(Acarus spp.)、嗜木蟎屬(Caloglyphus spp.)、足癢蟎屬(Chorioptes spp.)、胞蟎屬(Cytodites spp.)、頸下蟎屬(Hypodectes spp.)、腳蟎屬(Knemidocoptes spp.)、雞雛蟎屬(Laminosioptes spp.)、痂蟎屬(Notoedres spp.)、耳癢蟎屬(Otodectes spp.)、癢蟎屬(Psoroptes spp.)、翅蟎屬(Pterolichus spp.)、疥蟎屬(Sarcoptes spp.)、疥癬恙蟲屬(Trixacarus spp.)、食酪蟎屬(Tyrophagus spp.)。
寄生性原生動物的實例包括但不限於:
鞭毛蟲綱(Mastigophora)(鞭毛蟲綱(Flagellata)),諸如:
後滴門(Metamonada):來自雙滴蟲目(Diplomonadida),例如梨形鞭毛蟲屬(Giardia spp.)、旋核鞭毛蟲屬(Spironucleus spp.)。
副基體綱(Parabasala):來自毛滴蟲目(Trichomonadida),例如,組織鞭毛蟲(Histomonas spp.)、五毛滴蟲屬(Pentatrichomonas spp.)、四毛滴蟲屬(Tetratrichomonas spp.)、滴蟲屬(Trichomonas spp.)、三毛滴蟲屬(Tritrichomonas spp.)。
眼蟲門(Euglenozoa):來自錐蟲科(Trypanosomatida),例如利什曼屬(Leishmania spp.)、錐蟲屬(Trypanosoma spp.)。
肉鞭毛蟲門(Sarcomastigophora)(根足綱(Rhizopoda))諸如內阿米巴科(Entamoebidae)(例如內阿米巴屬(Entamoeba spp.))、Centramoebidae(例如棘阿米巴屬(Acanthamoeba sp.))、Euamoebidae(例如哈氏阿米巴屬(Hartmanella sp.))。
囊泡蟲總門(Alveolata)諸如頂覆門(Apicomplexa)(孢子蟲綱(Sporozoa)):例如隱孢子蟲屬(Cryptosporidium spp.);來自艾美球蟲目(Eimeriida),例如貝諾孢子蟲屬(Besnoitia spp.)、囊等胞球蟲屬(Cystoisospora spp.)、艾美球蟲屬(Eimeria spp.)、哈蒙屬(Hammondia spp.)、同形球蟲屬(Isospora spp.)、新孢球蟲屬(Neospora spp.)、肉孢子蟲屬(Sarcocystis spp.)、弓蟲屬(Toxoplasma spp.);來自阿德雷德目(Adeleida),例如,肝簇蟲屬(Hepatozoon spp.)、真球蟲屬(Klossiella spp.);來自血孢子蟲目(Haemosporida),例如,住血白冠病孢子蟲屬(Leucocytozoon spp.)、瘧原蟲屬(Plasmodium spp.);來自梨形目(Piroplasmida),例如,焦蟲屬(Babesia spp.)、纖毛蟲屬(Ciliophora spp.)、Echinozoon屬、泰勒原蟲屬(Theileria spp.);來自Vesibuliferida,例如,纖毛蟲屬(Balantidium spp.)、布克斯頓纖毛蟲屬(Buxtonella spp.)。
微孢子蟲(Microspora)諸如腦胞內原蟲屬(Encephalitozoon spp.)、腸內微孢子蟲屬(Enterocytozoon spp.)、球孢子蟲屬(Globidium spp.)、孢子蟲屬(Nosema spp.),及此外,例如黏體動物屬(Myxozoa spp.)。
使人類或動物致病的蠕蟲包括(例如)棘頭動物門(acanthocephala)、線蟲(nematodes)、舌形動物門(pentastoma)及扁形動物門(platyhelmintha)(例如單殖目(monogenea)、絛蟲(cestodes)及吸蟲(trematodes))。
例示性蠕蟲包括但不限於:
單殖目(Monogenea):例如:指環蟲屬(Dactylogyrus spp.)、三代蟲屬(Gyrodactylus spp.)、同盤吸蟲屬(Microbothrium spp.)、多盤吸蟲屬(Polystoma spp.)、Troglocephalus spp.;
絛蟲:來自擬葉目(Pseudophyllidea)之目,例如:吸葉絛蟲屬(Bothridium spp.)、廣節裂頭絛蟲屬(Diphyllobothrium spp.)、大複殖門絛蟲屬(Diphlogonoporus spp.)、呦蟲屬(Ichthyobothrium spp.)、舌狀絛蟲屬(Ligula spp.)、裂頭絛蟲屬(Schistocephalus spp.)、螺旋絛蟲屬(Spirometra spp.)。
來自圓葉目(Cyclophyllida)之目,例如:德里絛蟲屬(Andyra spp.)、裸頭絛蟲屬(Anoplocephala spp.)、無卵黄腺絛蟲屬(Avitellina spp.)、伯特絛蟲屬(Bertiella spp.)、彩帶絛蟲屬(Cittotaenia spp.)、戴維絛蟲屬(Davainea spp.)、雙睾絛蟲屬(Diorchis spp.)、倍殖孔絛蟲屬(Diplopylidium spp.)、複孔絛蟲屬(Dipylidium spp.)、棘球絛蟲屬(Echinococcus spp.)、棘殼絛蟲屬(Echinocotyle spp.)、棘鳞絛蟲屬(Echinolepis spp.)、泡尾絛蟲屬(Hydatigera spp.)、膜殼絛蟲屬(Hymenolepis spp.)、喬耶絛蟲屬(Joyeuxiella spp.)、中殖孔絛蟲屬(Mesocestoides spp.)、蒙尼絛蟲屬(Moniezia spp.)、副裸頭絛蟲屬(Paranoplocephala spp.)、瑞列絛蟲屬(Raillietina spp.)、斯泰絛蟲屬(Stilesia spp.)、帶狀絛蟲屬(Taenia spp.)、曲子宮絛蟲屬(Thysaniezia spp.)、繸體絛蟲屬(Thysanosoma spp.)。
吸蟲:來自複殖目(Digenea)之目,例如:澳畢吸蟲屬(Austrobilharzia spp.)、短咽吸蟲屬(Brachylaima spp.)、杯殖吸蟲屬(Calicophoron spp.)、下彎吸蟲屬(Catatropis spp.)、支睪吸蟲屬(Clonorchis spp.)、肛瘤吸蟲屬(Collyriclum spp.)、殖盤吸蟲屬(Cotylophoron spp.)、環腸吸蟲屬(Cyclocoelum spp.)、雙腔吸蟲屬(Dicrocoelium spp.)、雙穴吸蟲屬(Diplostomum spp.)、棘隙吸蟲屬(Echinochasmus spp.)、棘緣吸蟲屬(Echinoparyphium spp.)、棘口吸蟲屬(Echinostoma spp.)、闊盤吸蟲屬(Eurytrema spp.)、肝吸蟲屬(Fasciola spp.)、擬片形吸蟲屬(Fasciolides spp.)、薑片蟲屬(Fasciolopsis spp.)、菲策吸蟲屬(Fischoederius spp.)、腹袋吸蟲屬(Gastrothylacus spp.)、巨血吸蟲屬(Gigantobilharzia spp.)、巨盤吸蟲屬(Gigantocotyle spp.)、異形吸蟲屬(Heterophyes spp.)、低頸吸蟲屬(Hypoderaeum spp.)、彩蚴吸蟲屬(Leucochloridium spp.)、後殖吸蟲屬(Metagonimus spp.)、次睾吸蟲屬(Metorchis spp.)、隱孔吸蟲屬(Nanophyetus spp.)、背孔吸蟲屬(Notocotylus spp.)、後睪吸蟲屬(Opisthorchis spp.)、鳥畢吸蟲屬(Ornithobilharzia spp.)、肺吸蟲屬(Paragonimus spp.)、副雙口吸蟲屬(Paramphistomum spp.)、斜睾吸蟲屬(Plagiorchis spp.)、莖雙穴吸蟲屬(Posthodiplostomum spp.)、前殖吸蟲屬(Prosthogonimus spp.)、血吸蟲屬(Schistosoma spp.)、毛畢屬(Trichobilharzia spp.)、鮭吸蟲屬(Troglotrema spp.)、盲腔吸蟲屬(Typhlocoelum spp.)。
線蟲:來自毛形線蟲亞目(Trichinellida)之目,例如:毛細線蟲屬(Capillaria spp.)、真鞘線蟲屬(Eucoleus spp.)、副毛細線蟲屬(Paracapillaria spp.)、旋毛蟲屬(Trichinella spp.)、毛體線蟲屬(Trichosomoides spp.)、鞭蟲屬(Trichuris spp.)。
來自墊刃目(Tylenchida)之目,例如:細絲鯰屬(Micronema spp.)、副類圓線蟲屬(Parastrongyloides spp.)、類圓線蟲屬(Strongyloides spp.)。
來自小桿圓蟲目(Rhabditida)之目,例如:貓圓線蟲屬(Aelurostrongylus spp.)、裂口屬(Amidostomum spp.)、鉤蟲屬(Ancylostoma spp.)、血管圓線蟲屬(Angiostrongylus spp.)、氣管線蟲屬(Bronchonema spp.)、仰口線蟲屬(Bunostomum spp.)、夏氏線蟲屬(Chabertia spp.)、古柏線蟲屬(Cooperia spp.)、類古柏線蟲屬(Cooperioides spp.)、環棘線蟲屬(Crenosoma spp.)、盅口線蟲屬(Cyathostomum spp.)、類圓線蟲屬(Cyclococercus spp.)、環齒口線蟲屬(Cyclodontostomum spp.)、杯環線蟲屬(Cylicocyclus spp.)、杯冠線蟲屬(Cylicostephanus spp.)、柱咽線蟲屬(Cylindropharynx spp.)、囊尾線蟲屬(Cystocaulus spp.)、網尾線蟲屬(Dictyocaulus spp.)、鹿圓線蟲屬(Elaphostrongylus spp.)、類絲蟲屬(Filaroides spp.)、球頭線蟲屬(Globocephalus spp.)、圖紋屬(Graphidium spp.)、輻首線蟲屬(Gyalocephalus spp.)、血矛線蟲屬(Haemonchus spp.)、螺旋線蟲屬(Heligmosomoides spp.)、豬圓線蟲屬(Hyostrongylus spp.)、馬什線蟲屬(Marshallagia spp.)、後圓線蟲屬(Metastrongylus spp.)、繆勒線蟲屬(Muellerius spp.)、鉤蟲屬(Necator spp.)、細頸線蟲(Nematodirus spp.)、新圓線蟲屬(Neostrongylus spp.)、日本圓線蟲屬(Nippostrongylus spp.)、尖柱線蟲屬(Obeliscoides spp.)、食管齒線蟲屬(Oesophagodontus spp.)、食道口線蟲屬(Oesophagostomum spp.)、盤尾絲蟲屬(Ollulanus spp.)、豬圓屬(Ornithostrongylus spp.)、奧斯勒屬(Oslerus spp.)、奧斯特線蟲屬(Ostertagia spp.)、副古柏線蟲屬(Paracooperia spp.)、副環棘線蟲屬(Paracrenosoma spp.)、副類絲蟲屬(Parafilaroides spp.)、副鹿圓線蟲屬(Parelaphostrongylus spp.)、肺尾線蟲屬(Pneumocaulus spp.)、肺圓蟲屬(Pneumostrongylus spp.)、盂口線蟲屬(Poteriostomum spp.)、原圓線蟲屬(Protostrongylus spp.)、尖尾線蟲亞屬(Spicocaulus spp.)、冠尾線蟲屬(Stephanurus spp.)、圓線蟲屬(Strongylus spp.)、比翼線蟲屬(Syngamus spp.)、背帶線蟲屬(Teladorsagia spp.)、盅口線蟲屬(Trichonema spp.)、毛圓線蟲屬(Trichostrongylus spp.)、三齒線蟲屬(Triodontophorus spp.)、短竇圓線蟲屬(Troglostrongylus spp.)、彎口線蟲屬(Uncinaria spp.)。
來自旋尾目(Spirurida)之目,例如:棘唇屬(Acanthocheilonema spp.)、異尖線蟲屬(Anisakis spp.)、禽蛔蟲屬(Ascaridia spp.)、蛔蟲屬(Ascaris spp.)、螺咽屬(Ascarops spp.)、無刺線蟲屬(Aspiculuris spp.)、貝利斯蛔蟲屬(Baylisascaris spp.)、布氏絲蟲屬(Brugia spp.)、Cercopithifilaria屬、毛體線蟲屬(Crassicauda spp.)、雙瓣絲蟲屬(Dipetalonema spp.)、心絲蟲屬(Dirofilaria spp.)、龍線蟲屬(Dracunculus spp.)、德斯線蟲屬(Draschia spp.)、蟯蟲屬(Enterobius spp.)、絲狀蟲屬(Filaria spp.)、顎口線蟲屬(Gnathostoma spp.)、筒線蟲屬(Gongylonema spp.)、麗線蟲屬(Habronema spp.)、異刺線蟲屬(Heterakis spp.)、光絲蟲屬(Litomosoides spp.)、羅阿絲蟲屬(Loa spp.)、蟠尾絲蟲屬(Onchocerca spp.)、尖尾線蟲屬(Oxyuris spp.)、副柔線蟲屬(Parabronema spp.)、副絲蟲屬(Parafilaria spp.)、副蛔屬(Parascaris spp.)、栓尾線蟲屬(Passalurus spp.)、泡翼線蟲屬(Physaloptera spp.)、Probstmayria屬、Pseudofilaria屬、腹腔絲蟲屬(Setaria spp.)、Skjrabinema屬、尾旋屬(Spirocerca spp.)、冠絲蟲屬(Stephanofilaria spp.)、圓線蟲屬(Strongyluris spp.)、管狀線蟲屬(Syphacia spp.)、吸吮線蟲屬(Thelazia spp.)、弓蛔線蟲屬(Toxascaris spp.)、弓首蛔蟲屬(Toxocara spp.)、吳策線蟲屬(Wuchereria spp.)。
棘頭動物門(Acantocephala):來自寡棘吻目(Oligacanthorhynchida)之目,例如:巨吻棘頭蟲屬(Macracanthorhynchus spp.)、前睪棘頭蟲屬(Prosthenorchis spp.);來自念珠目(Moniliformida)之目,例如:念珠棘頭蟲屬(Moniliformis spp.);
來自多形目(Polymorphida)之目,例如:細頸棘頭蟲屬(Filicollis spp.);來自棘吻目(Echinorhynchida)之目,例如棘頭蟲屬(Acanthocephalus spp.)、魚棘頭蟲屬(Echinorhynchus spp.)、似細吻棘頭蟲屬(Leptorhynchoides spp.)。
舌形動物門(Pentastoma):來自舌形蟲目(Porocephalida)之目,例如,舌形蟲屬(Linguatula spp.)。
在獸醫領域及動物飼養中,式(I)化合物之投予係藉由該項技術中通常已知的方法(諸如經腸、非經腸、經皮膚或經鼻)以適當製劑的形式進行。投予可預防性地、補救性預防地(metaphylactic)或治療性地進行。
因此,本發明之一個實施態樣關於用作為藥劑之式(I)化合物。
另一態樣關於用作為抗體內寄生蟲劑之式(I)化合物。
另一特定態樣關於用作為驅蟲劑(更特別是用作為殺線蟲劑、殺扁形動物劑(platyhelminthicidal agent)、殺棘頭蟲劑(acanthocephalicidal agent)或殺舌形蟲劑(pentastomicidal agent))之式(I)化合物。
另一特定態樣關於用作為抗原蟲劑之式(I)化合物。
另一態樣關於用作為抗體外寄生蟲劑(特別是殺節肢動物劑,更特別是殺昆蟲劑或殺蟎劑)之式(I)化合物。
本發明之其他態樣為獸醫調配物,其包含有效量的至少一種式(I)化合物及下列中之至少一者:醫藥上可接受之賦形劑(例如固態或液態稀釋劑)、醫藥上可接受之助劑(例如界面活性劑),特別是常用於獸醫調配物中的醫藥上可接受之賦形劑及/或醫藥上可接受之助劑。
本發明相關的態樣為一種製備如本文所述的獸醫調配物之方法,其包含混合至少一種式(I)化合物與醫藥上可接受之賦形劑及/或助劑(特別是與常用於獸醫調配物中的醫藥上可接受之賦形劑及/或助劑)的步驟。
本發明之另一特定態樣為選自根據上述態樣之殺體外寄生蟲及殺體內寄生蟲調配物的群組,更特別是選自驅蟲、抗原蟲及殺節肢動物調配物之群組,甚至更特別是選自殺線蟲、殺扇形動物、殺棘頭動物、殺舌形動物、殺昆蟲及殺蟎調配物之群組的獸醫調配物,以及彼等的製備方法。
另一態樣關於一種治療寄生蟲感染(特別是被選自本文所述的體外寄生蟲及體內寄生蟲之群組的寄生蟲感染)之方法,其係藉由將有效量的式(I)化合物施用至對其有需要的動物,特別是非人類動物。
另一態樣關於一種治療寄生蟲感染(特別是被選自本文所述的體外寄生蟲及體內寄生蟲之群組的寄生蟲感染)之方法,其係藉由將如本文所定義之獸醫調配物施用至對其有需要的動物,特別是非人類動物。
另一態樣關於式(I)化合物於治療動物(特別是非人類動物)中的寄生蟲感染(特別是被選自本文所述的體外寄生蟲及體內寄生蟲之群組的寄生蟲感染)之用途。
在本文之動物健康或獸醫領域的情況下,術語“治療”包括預防性、補救性預防(metaphylactic)或治療性治療。
在一特定實施態樣中,藉此提供用於獸醫領域的至少一種式(I)化合物與其他活性成分(特別是與殺體內及殺體外寄生蟲劑)之混合物。
在動物健康領域中,“混合物”不僅意指兩種(或更多種)不同的活性成分調配成共同的調配物且因此一起施用,且亦關於包含各活性成分的單獨調配物之產品。因此,若欲施用兩種以上的活性化合物時,可將所有的活性化合物調配成共同的調配物或可將所有的活性化合物調配成單獨調配物;同樣地可行的是混合形式,其中將一些活性化合物調配在一起及將一些活性化合物單獨調配。單獨調配物允許單獨或連續施用討論中的活性化合物。
在本文中以彼等的俗名指定之活性化合物為已知且描述於(例如)“殺蟲劑手冊(The Pesticide Manual”,見上)中或可在網際網路中搜尋(例如http://www.alanwood.net/Pesticide)。
來自作為混合伴體的殺體外寄生蟲劑之群組的例示性活性成分包括但不限於在上述詳列之殺昆蟲劑及殺蟎劑。依照上述根據現行作用分類方案之IRAM模式(IRAC Mode of Action Classification Scheme)的分類將可使用的其他活性成分列示於下:(1)乙醯膽鹼酯酶(AChE)抑制劑;(2) GABA-閘控之氯離子通道阻斷劑;(3)鈉通道調節劑;(4)菸鹼乙醯膽鹼受體(nAChR)競爭調節劑;(5) 菸鹼乙醯膽鹼受體(nAChR)別位調節劑;(6)麩胺酸閘控之氯離子通道(GluCl)別位調節劑;(7) 保幼激素模擬物;(8) 雜項非特異性(多位置)抑制劑;(9) 弦音器(Chordotonal organ)之調節劑;(10) 蟎生長抑制劑;(12) 粒腺體ATP合成酶之抑制劑,諸如ATP干擾劑;(13) 經由質子梯度干擾的氧化性磷酸化之去偶合劑;(14)菸鹼能乙醯膽鹼受體通道阻斷劑;(15) 第0型甲殼素生物合成之抑制劑;(16) 第1型甲殼素生物合成抑制劑;(17) 脫皮干擾劑(特別是用於雙翅目(Diptera),即雙翅目昆蟲);(18) 蛻皮激素受體促效劑;(19)章魚胺受體促效劑;(21) 粒腺體複合物I電子傳遞抑制劑;(25) 粒腺體複合物II電子傳遞抑制劑;(20) 粒腺體複合物III電子傳遞抑制劑;(22) 電壓依賴性鈉通道阻斷劑;(23)乙醯基CoA羧酶之抑制劑;(28) 藍尼定(Ryanodine)受體調節劑;
具有未知或非特異性作用模式之化合物,例如氟硝二苯胺(fentrifanil)、芬諾靈(fenoxacrim)、環普靈(cycloprene)、克氯苯(chlorobenzilate)、殺蟲脒(chlordimeform)、氟苯滅(flubenzimine)、地昔尼爾(dicyclanil)、磺胺蟎酯(amidoflumet)、蟎離丹(quinomethionate)、苯蟎噻(triarathene)、氯噻唑苯(clothiazoben)、殺蟎好(tetrasul)、油酸鉀、石油、惡蟲酮(metoxadiazone)、紅鈴蟲性誘素(gossyplure)、福特淨(flutenzine)、新殺蟎(bromopropylate)、冰晶石(cryolite);
來自其他類別之化合物,例如畜蟲威(butacarb)、敵蠅威(dimetilan)、除線威(cloethocarb)、磷蟲威(phosphocarb)、亞特松(pirimiphos)(-乙基)、巴拉松(parathion)(-乙基)、滅克松(methacrifos)、o-水楊酸異丙酯、三氯松(trichlorfon)、替夠拉那(tigolaner)、硫丙磷(sulprofos)、加護松(propaphos)、克線丹(sebufos)、必達松(pyridathion)、發硫磷(prothoate)、除線磷(dichlofenthion)、風吸磷(demeton-S-methylsulphon)、依殺松(isazofos)、苯腈磷(cyanofenphos)、得拉松(dialifos)、三硫磷(carbophenothion)、奧他硫松(autathiofos)、阿隆芬文松(aromfenvinfos)(-甲基)、谷速松(azinphos)(-乙基)、陶斯松(chlorpyrifos)(-乙基)、丁苯硫磷(fosmethilan)、碘硫磷(iodofenphos)、蔬果磷(dioxabenzofos)、福木松(formothion)、大福松(fonofos)、福拉松(flupyrazofos)、繁福松(fensulfothion)、益多松(etrimfos);
有機氯,例如毒殺芬(camphechlor)、靈丹(lindane)、飛佈達(heptachlor);或苯基吡唑,例如乙醯蟲腈(acetoprole)、比拉扶普(pyrafluprole)、比利普(pyriprole)、繁尼利普(vaniliprole)、維吉黴素(sisapronil);或異㗁唑啉,例如賽蘭(sarolaner)、阿佛拉那(afoxolaner)、羅提蘭(lotilaner)、氟拉蘭(fluralaner);
擬除蟲菊酯類(pyrethroids),例如(順式-、反式-),甲氧苄氟菊酯(metofluthrin)、普福寧(profluthrin)、氟芬普(flufenprox)、福布賽寧特(flubrocythrinate)、福芬普(fubfenprox)、芬福寧(fenfluthrin)、普垂芬布(protrifenbute)、必滅寧(pyresmethrin)、RU15525、環戊烯丙菊酯(terallethrin)、順式-列滅寧(cis-resmethrin)、氯氟醚菊酯(heptafluthrin)、百索美寧(bioethanomethrin)、百普美寧(biopermethrin)、芬比寧(fenpyrithrin)、順式-賽滅寧(cis-cypermethrin)、順式-百滅寧(permethrin)、氯氟氰菊(clocythrin)、賽洛寧(cyhalothrin)(λ-)、二氯炔戊菊酯(chlovaporthrin)或鹵化烴化合物(HCH);
新菸鹼類(neonicotinoid),例如硝蟲噻𠯤(nithiazine)
二氯滅齊(dicloromezotiaz)、三氟普靈(triflumezopyrim)
巨環內酯,例如奈馬克丁(nemadectin)、伊維菌素(ivermectin)、拉替菌素(latidectin)、莫西菌素(moxidectin)、塞拉菌素(selamectin)、依普菌素(eprinomectin)、多拉菌素(doramectin)、因滅汀(emamectin)苯甲酸鹽;米貝黴素(milbemycin)肟
烯蟲硫酯(triprene)、保幼醚(epofenonane)、二苯丙醚(diofenolan);
生物製劑、荷爾蒙或費洛蒙,例如天然產物,例如蘇力菌素(thuringiensin)、十二碳二烯醇(codlemone)或印度苦楝組分;
二硝基苯酚,例如白粉克(dinocap)、大脫蟎(dinobuton)、百蟎克(binapacryl);
苯甲醯脲,例如氟佐隆(fluazuron)、氟幼脲(penfluron);
脒衍生物,例如殺蟲脒(chlormebuform)、蟎蜱胺(cymiazole)、得米地曲(demiditraz);
蜂箱蜂瓦蟎殺蟎劑,例如有機酸類,例如甲酸、草酸。
來自作為混合伴體的殺體內寄生蟲劑之群組的例示性活性成分包括但不限於驅蠕蟲活性化合物及抗原蟲活性化合物。
驅蟲活性化合物包括但不限於下列的殺線蟲、殺白蟻及/或殺絛蟲活性化合物:
來自巨環內酯的類別,例如:依普菌素(eprinomectin)、阿巴汀(abamectin)、奈馬克丁(nemadectin)、莫西菌素(moxidectin)、多拉菌素(doramectin)、塞拉菌素(selamectin)、雷皮菌素(lepimectin)、拉替菌素(latidectin)、密滅汀(milbemectin)、伊維菌素(ivermectin)、因滅汀(emamectin)、米貝黴素(milbemycin);
來自苯并咪唑和前苯并咪唑的類別,例如:奧苯達唑(oxibendazole)、甲苯達唑(mebendazole)、三氯苯達唑(triclabendazole)、多保淨(thiophanate)、帕苯達唑(parbendazole)、奧芬達唑(oxfendazole)、奈托比胺(netobimin)、芬苯達唑(fenbendazole)、非班太爾(febantel)、腐絕(thiabendazole)、環苯達唑(cyclobendazole)、坎苯達唑(cambendazole)、阿苯達唑(albendazole)亞碸、阿苯達唑、氟苯達唑(flubendazole);
來自酯肽(depsipeptide)的類別,較佳環酯肽,特別是24-員環酯肽,例如:艾默德斯(emodepside)、PF1022A;
來自四氫嘧啶的類別,例如:莫侖太爾(morantel)、噻嘧啶(pyrantel)、奧克太爾(oxantel);
來自咪唑并噻唑的類別,例如:布他咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
來自胺苯基脒的類別,例如:阿米太爾(amidantel)、去醯基化阿米太爾(dAMD)、三苯雙脒(tribendimidine);
來自胺基乙腈的類別,例如:莫盤太爾(monepantel);
來自對郝青醯胺(paraherquamide)的類別,例如:對郝青醯胺、得曲恩特(derquantel);
來自柳醯胺苯的類別,例如:三溴沙侖(tribromsalan)、溴沙尼特(bromoxanide) 、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯氰碘柳胺(closantel)、氯硝柳胺(niclosamide)、羥氯柳苯胺(oxyclozanide)、雷複尼特(rafoxanide);
來自經取代的酚的類別,例如:硝碘酚腈(nitroxynil)、硫雙二氯酚(bithionole)、二碘硝酚(disophenol)、六氯酚(hexachlorophen)、聯硝氯酚(niclofolan)、美克芬崙(meniclopholan);
來自有機磷酸酯的類別,例如:三氯松(trichlorfon)、萘肽磷(naftalofos)、二氯松(dichlorvos)/DDVP、育畜磷(crufomate)、牛壁逃(coumaphos)、哈洛克酮(haloxon);
來自哌𠯤酮/喹啉的類別,例如:吡喹酮(praziquantel)、依西太爾(epsiprantel);
來自哌𠯤的類別,例如:哌𠯤、羥𠯤(hydroxyzine);
來自四環黴素的類別,例如:四環素、氯四環素、去氧羥四環素(doxycycline)、氧四環素(oxytetracycline)、吡甲四環素(rolitetracycline);
來自各種其他類別,例如:丁萘脒(bunamidine)、尼立達唑(niridazole)、雷瑣太爾(resorantel)、歐姆泛洛丁(omphalotin)、奧替普拉(oltipraz)、硝硫氰酯(nitroscanate)、硝碘酚腈(nitroxynil)、奥沙尼喹(oxamniquin)、米拉散(mirasan)、米拉西(miracil)、硫蒽酮(lucanthone)、海恩酮(hycanthon)、海托啉(hetolin)、吐根素(emetine)、乙胺𠯤(diethylcarbamazine)、二氯芬(dichlorophen)、地芬尼泰(diamfenetide)、氯硝西泮(clonazepam)、苄芬寧(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
抗原蟲活性化合物包括但不限於下列活性化合物:
來自三𠯤的類別,例如:地克朱利(diclazuril)、波那朱利(ponazuril)、勒崔朱利(letrazuril)、托曲朱利(toltrazuril);
來自聚醚離子載體的類別,例如:莫能黴素(monensin)、鹽黴素(salinomycin)、馬杜黴素(maduramicin)、甲基鹽黴素(narasin);
來自巨環內酯的類別,例如:米貝黴素(milbemycin)、紅黴素(erythromycin);
來自喹諾酮的類別,例如:恩諾沙星(enrofloxacin)、普多沙星(pradofloxacin);
來自奎寧的類別,例如:氯奎寧(chloroquin);
來自嘧啶的類別,例如:乙胺嘧啶(pyrimethamine);
來自磺醯胺的類別,例如:磺胺喹啉(sulfaquinoxaline)、甲氧苄啶(trimethoprim)、磺胺氯吡𠯤(sulfaclozin);
來自硫胺的類別,例如:氨丙啉(amprolium);
來自林可醯胺(lincosamines)的類別,例如:克林達黴素(clindamycin);
來自羰胺苯的類別,例如:雙咪苯脲(imidocarb);
來自硝基呋喃的類別,例如:硝呋替莫(nifurtimox);
來自喹唑啉酮生物鹼的類別,例如:鹵夫酮(halofuginone);
來自各種其他類別,例如:奧沙尼喹(oxamniquin)、巴龍黴素(paromomycin);
來自疫苗類別或來自微生物之抗原,例如:羅氏犬焦蟲(Babesia canis rossi)、盲腸型球蟲(Eimeria tenella)、早熟艾美球蟲(Eimeria praecox)、毒害艾美球蟲(Eimeria necatrix)、緩艾美球蟲(Eimeria mitis)、巨型艾美球蟲(Eimeria maxima)、布氏艾美球蟲(Eimeria brunetti)、堆形艾美球蟲(Eimeria acervulina)、佛氏犬焦蟲(Babesia canis vogeli)、嬰兒利什曼原蟲(Leishmania infantum)、犬焦蟲症(Babesia canis canis)、牛肺蟲(Dictyocaulus viviparus)。
所有命名之混合伴體,若彼等的官能基能夠的話,則視情況亦可與適當鹼或酸形成鹽。
病媒控制
式(I)化合物亦可用於病媒控制。就本發明的目的而言,病媒為能夠將病原體(諸如,例如:病毒、蠕蟲、單細胞生物與細菌)從儲體(植物、動物、人類、等等)傳染至宿主之節肢動物,特別是昆蟲或蛛形綱動物。該等病原體可機械式地(例如藉由非叮咬性蠅之沙眼)或注入(例如:藉由蚊子之瘧疾寄生蟲)傳染至宿主。
病媒及彼等所傳染之疾病或病原體的實例為:
1) 蚊子
- 瘧蚊(Anopheles):瘧疾(malaria)、絲蟲病(filariasis);
- 家蚊(Culex):日本腦炎、其他病毒性疾病、絲蟲病、其他蠕蟲之傳染;
- 斑蚊(Aedes):黃熱病、登革熱、其他病毒性疾病、絲蟲病;
- 蚋科(Simuliidae):蠕蟲(尤其是蟠尾絲蟲(Onchocerca volvulus))之傳染;
- 蛾蚋科(Psychodidae):利什曼體病(leishmamiasis)的傳染
2) 蝨:皮膚傳染病、流行性斑疹傷寒;
3) 蚤:鼠疫、地方性斑疹傷寒、絛蟲;
4) 蠅:昏睡症(錐蟲病);霍亂、其他細菌性疾病;
5) 蟎:蟎病(acariosis)、流行性斑疹傷寒、痘立克次體、兔熱病、聖路易斯腦炎(Saint Louis encephalitis)、蜱傳腦炎(TBE)、克里米亞-剛果出血熱、回歸熱;
6) 蜱:疏螺旋體病(borelliosis)諸如伯氏疏螺旋體(Borrelia burgdorferi sensu lato)、杜通氏螺旋體(Borrelia duttoni)、蜱傳性腦炎、Q熱(貝氏考克斯菌(Coxiella bumetii))、焦蟲症(犬焦蟲症(Babesia canis canis))、艾利希氏體症(ehrlichiosis)。
就本發明的意義而言之病媒的實例為能夠將植物病毒傳染至植物之昆蟲,例如:蚜蟲、蠅、葉蟬或薊馬。其他能夠傳染植物病毒之病媒為蜘蛛蟎、蝨、甲蟲和線蟲。
就本發明的意義而言之病媒的其他實例為能夠將病原體傳染至動物及/或人類的昆蟲和蜘蛛綱動物諸如蚊子,特別是斑蚊(Aedes)、瘧蚊(Anopheles),例如甘比亞瘧蚊(A. gambiae)、阿拉伯瘧蚊(A. arabiensis)、致死瘧蚊(A. funestus)、大劣瘧蚊(A. dirus)(瘧疾)與家蚊(Culex)、蛾蚋(psychodids)諸如白蛉(Phlebotomus)、羅蛉(Lutzomyia)、蝨、跳蚤、蠅、蟎、和蜱。
若式(I)化合物具有抗破壞性,則亦可能控制病媒。
式(I)化合物適合用於預防由病媒傳染的疾病及/或病原體。因此,本發明之另一態樣為式(I)化合物用於病媒控制之用途,例如用於農業、園藝、花園和休閒設施,且亦用於保護材料和儲藏產品。
工業材料的保護
式(I)化合物適合於護工業材料免受昆蟲(例如來自鞘翅目(Coleoptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鱗翅類(Lepidoptera)、嚙蟲目(Psocoptera)和衣魚目(Zygentoma))的攻擊或破壞。
工業材料在本文中係理解為意指無生命材料,諸如較佳為塑膠、黏著劑、膠水、紙張及紙板、皮革、木材、加工木製品及塗料組成物。本發明使用於保護木材是特佳的。
在另一實施態樣中,式(I)化合物係與至少一種其他的殺蟲劑及/或至少一種殺真菌劑一起使用。
在另一實施態樣中,式(I)化合物係以備用殺蟲劑存在,即彼等可不進一步修飾而施用於討論中的材料。適合的其他殺蟲劑或殺真菌劑特別是彼等以上提及者。
令人驚訝地,亦發現式(I)化合物可用於防止與鹽水或半鹹水進行接觸之物體(特別是船體、隔板、編網、建築物、繫泊和傳訊系統)被污塞。同樣地可能使用單獨或與其他活性化合物組合的式(I)化合物作為抗污塞劑。
控制衛生領域 中的動物害蟲
式(I)化合物適合於控制衛生領域中的動物害蟲。更具體地說,本發明可應用於居家領域、衛生領域及儲存產品之保護,尤其是用於控制在封閉空間(諸如公寓、廠房、辦公室、車廂、動物繁殖場)中所遇到的昆蟲、蛛形綱動物、蜱和蟎。為了控制動物害蟲,式(I)化合物係單獨或與其他活性化合物及/或助劑組合使用。彼等較佳地用於居家殺蟲劑產品中。式(I)化合物有效對抗敏感性及抗性物種,且對抗所有發育期。
此等害蟲包括例如來自蜘蛛綱、來自蠍目、蜘蛛目和盲珠目、來自唇足綱和倍足綱,來自昆蟲綱蜚蠊目,來自鞘翅目、革翅目、雙翅目、異翅亞目(Heteroptera)、膜翅目、等翅目、鱗翅目、毛蝨目、嚙蟲目、跳躍亞目或直翅目、隱翅目(Siphonaptera)和衣魚目、及來自軟甲亞綱(Malacostraca)等足目之害蟲。
彼等係以例如氣霧劑、無壓噴霧產品(例如泵及霧化器噴霧)、自動噴霧系統、噴霧器、發泡體、凝膠、具有由纖維素或塑膠所製成之蒸發片的蒸發器產品、液體蒸發器、凝膠和膜式蒸發器、推進劑驅動式蒸發器、無能源或被動式蒸發系統、防蟲紙、防蟲袋和防蟲膠,呈顆粒或細粉,用於散佈之誘餌或誘餌台使用。
縮寫和符號
AcOH: 乙酸
aq.: 水性
br.: 寬峰
d: 雙重峰
DCC: N,N’-二環己基碳二亞胺
DIPEA: N,N-二異丙基乙胺
DMF: N,N-二甲基甲醯胺
DMSO: 二甲亞碸
ee: 鏡像異構物超越量
eq.: 當量
ES: 電噴灑游離
Et
3N 三乙胺
EtOAc: 乙酸乙酯
hr(s) 小時
HATU: 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓-3-氧化物六氟磷酸鹽
HOBt: 1-羥基苯并三唑水合物
HPLC: 高效液相層析法
iPrOH: 異丙醇
J: 偶合常數
LCMS: 液相層析法-質譜法
m/z: 質量對電荷比
M: 體積莫耳濃度
m: 多重峰
MeCN 乙腈
MeOH: 甲醇
NaH
2PO
4磷酸二氫鈉
NaOH 氫氧化鈉
Na
2SO
4硫酸鈉
NH
4Cl 氯化銨
NMR: 核磁共振
q: 四重峰
r. t.: 室溫
R
t: 滯留時間
s: 單峰
sat.: 飽和
T: 溫度
t: 三重峰
T3P
®: 丙基膦酸酐
THF: 四氫呋喃
TMSOK 三甲基矽醇鉀
wt.: 重量
δ: 化學位移
λ: 波長
方法和 中間物 的說明
式I’化合物可如下列流程1中所示製備,其中R
1、R
2、R
3a、R
3b、R
4、Q
1、Q
2和Y係如前所定義及X表示OH或Cl。
流程 1
X = OH:使式(a)之唑化合物與式(b)之羧酸(X = OH)反應以形成式I’化合物。例如,將式(a)之唑、式(b)之羧酸(X = OH)、適當偶合劑(諸如T3P
®、HATU、DCC或HOBt)、適當鹼(諸如三乙胺或DIPEA)、在適當溶劑(諸如乙酸乙酯或DMF)中的混合物於範圍從約0至100℃的溫度下混合以提供式I’化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
X = Cl:使式(a)之唑化合物與式(b)之羧醯氯(X = Cl)反應以形成式I’化合物.例如,式(a)之唑、式(b)之羧醯氯(X = Cl)、適當鹼(諸如三乙胺或DIPEA)、在適當溶劑(諸如二氯甲烷或THF)中之混合物於範圍從約0至100℃的溫度下混合以提供式I’化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
式(b)之羧酸(X = OH)和式(b)之羧醯氯(X = Cl)為市售或可藉由熟習現有技術者已知的方法合成。
例如,用於實施例I-048和I-049的合成之羧酸可以類似於WO 2016198507、WO 2015084936、WO 2015148354、WO 2015148373使用如引用中所述類似的觸媒系統(由碘化銅(I)和(E,E)-N,N'-環己烷-1,2-二基雙[1-(吡啶-2-基)甲亞胺組成],關於後者參見US 20030236413)合成。
所需要的式(a)之唑化合物可如下列流程2中所示製備,其中R
1、R
3a、R
3b、R
4、Q
1、Q
2和Y係如前所述且LG為適當脫離基(亦參見WO 2017192385)。
流程 2
使式(c)之胺與式(d)之經取代的唑反應以形成式(a)化合物。例如,將式(d)之唑、式(c)之胺、適當鹼(諸如K
2CO
3、NaH或DIPEA)在適當溶劑(諸如乙腈或DMF)中之混合物於範圍從約20至120℃的溫度下混合,以提供式(a)化合物,接著可將其分離,且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。
或者,使式(d)之經取代的唑與氨反應以形成式(e)化合物。例如,將氨在適當溶劑(諸如甲醇)中之溶液及式(d)之經取代的唑在密封管中於範圍從0至25℃溫度下混合,以提供式(e)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如研磨)純化。將式(e)之經取代的唑、式(f)化合物、適當鹼(諸如K
2CO
3或DIPEA)在適當溶劑(諸如乙腈或DMF)中於範圍從約20至120℃的溫度下混合,以提供式(a)化合物,接著可將其分離,且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。
式(c)之胺和式(f)化合物為市售或可藉由熟習現有技術者已知的方法合成。所需要的式(d)之唑化合物可如下列流程3中所示製備,其中R
3a、R
3b、R
4、R
5、Q
1、Q
2和Y係如前所述,LG為適當脫離基(亦參見WO 2017192385)。
流程 3
使式(h)之醯胺與
N,N-二甲基醯胺二甲基縮醛(g)反應以形成式(i)化合物,接著使其與肼(j)在酸性條件下反應以形成式(d)化合物。例如,使式(h)化合物和式(g)之
N,N-二甲基醯胺二甲基縮醛在適當溶劑(諸如CH
2Cl
2)中於回流下反應以提供式(i)化合物。移除溶劑後,使式(i)化合物與經取代的肼(j)在適當溶劑(諸如1,4-二㗁烷、乙酸或該等溶劑之混合物)中於範圍從約20至100℃的溫度下反應以提供式(d)化合物,接著可將其分離,且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。
或者,使式(k)之羧酸衍生物與式(l)之胺和適當鹼(諸如三乙胺或DIPEA)在適當溶劑(諸如甲苯)中於範圍從約0至120℃的溫度下反應。接著可將所得化合物(m)分離且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。使所得式(m)之醯胺和五氯化磷在適當溶劑(諸如CH
2Cl
2)中於室溫(r.t.)下反應及接著在0℃下將三甲矽基加疊氮化物添至混合物並於室溫下攪拌混合物以提供式(d)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
式(g)之
N,N-二甲基醯胺縮醛、式(h)之醯胺、式(k)之羧酸衍生物和式(j)之肼為市售或可藉由熟習現有技術者已知的方法合成。
式I''a化合物可如下列流程4中所示製備,其中R
1、R
2、R
3a、R
3b、R
4、R
5和Y係如先前所定義。
流程 4
使式(n)之醯胺與式(g)之
N,N-二甲基醯胺二甲基縮醛反應以形成式(o)化合物,隨後使其與式(j)之經取代的肼在酸性條件下反應以形成式I''a化合物。例如,使式(n)化合物和式(g)之
N,N-二甲基醯胺二甲基縮醛在適當溶劑(諸如CH
2Cl
2)中於回流下反應以提供式(o)化合物。移除溶劑後,使式(o)化合物與式(j)之經取代的肼在適當溶劑(諸如1,4-二㗁烷、乙酸或該等溶劑之混合物)中於範圍從約20至100℃的溫度下反應。接著可將所得式I''a化合物分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
所需要的式(n)之醯胺可如下列流程5中所示製備,其中R
1、R
2、R
3、和Y係如前所述(亦參見WO 2017192385)。
流程 5
使式(p)之胺基醯胺與式(b)之羧酸反應以形成式(n)化合物。例如,將式(p)之胺基醯胺、羧酸(b)、適當偶合劑(諸如T3P®、HATU、DCC或HOBt)、適當鹼(諸如三乙胺或DIPEA)在適當溶劑(諸如乙酸乙酯或DMF)中之混合物於範圍從約0至100℃的溫度下混合,以提供式(n)化合物,接著可將其分離,且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。
或者,使式(q)之胺基酸與亞硫醯氯在適當溶劑(諸如MeOH)中於室溫下反應以提供式(r)之胺基酯。使所得胺基酯(r)與醛或酮、適當還原劑 (諸如三乙醯氧基硼氫化鈉)、脫水劑(諸如Na
2SO
4)在適當溶劑(諸如乙酸)中於室溫下反應以提供式(s)化合物。接著使所得式(s)之胺基酯與式(b)之羧酸、適當偶合劑(諸如T3P
®)、適當鹼(諸如DIPEA)在適當溶劑(諸如乙酸乙酯)中於約90℃下反應以提供式(t)之醯胺基酯,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。使所得式(t)之醯胺基酯與氮化鎂在密封管中在適當溶劑(諸如MeOH)中於約80℃下反應以提供式(n)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法或萃取)純化。
式(b)和(q)之化合物為市售。所需要的式(p)之胺基醯胺化合物為市售或可如下列流程6中所示製備,其中R
1、R
3a、R
3b、和Y係如前所述及LG為適當脫離基(亦參見WO 2017192385)。
式(c)和(h)之化合物為市售。
流程 6
使式(c)之胺與式(h)之醯胺反應以形成式(p)化合物。例如,將式(c)之胺、式(h)之醯胺、適當鹼(諸如K
2CO
3或DIPEA)在適當溶劑(諸如乙腈或DMF)中之混合物在25-80℃下混合以提供式(p)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
在另一種方法中,式I''a化合物可如下列流程7中所示製備,其中R
1、R
2、R
3a、R
3b、R
4、R
5和Y係如先前所定義。
流程 7
使式(u)之脒鹽酸鹽與式(v)之酸反應。例如,將式(u)之脒鹽酸鹽、羧酸(v)、適當偶合劑(諸如HATU、DCC或HOBt)、適當鹼(諸如三乙胺或DIPEA)在適當溶劑(諸如乙酸乙酯或DMF)中之混合物於範圍從約0至100℃的溫度下混合,以形成式(w)化合物,隨後使其與式(j)之經取代的肼在酸性條件下反應以形成式I''a化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
式(u)之脒鹽酸鹽、式(v)之羧酸衍生物和式(j)之肼為市售或可藉由該項技術人員已知的方法合成。
通式(ya)之亞碸(鋶化物(sulfine))和式(yb)之碸可如下列流程8中所示製備,其中Ar為苯基或雜芳基和R
x為C
1-C
6烷基、C
1-C
6鹵烷基、視需要地經取代的苯基或視需要地經取代的C
3-C
6環烷基。
流程 8
使式(x)之含氫硫基(sulfanyl)化合物與氧化劑(諸如3-氯過氧苯甲酸或氯化釕(III)與過碘酸鈉組合)反應以形成式(ya)或(yb)之化合物,取決於氧化劑之莫耳當量。式(ya)之亞磺醯基化合物係理解為形成光學異構物或不同組成的異構物混合物。使式(ya)之含亞磺醯基化合物與氧化劑(諸如3-氯過氧苯甲酸或氯化釕(III)與過碘酸鈉組合)反應以形成式(yb)之含碸化合物。
式(zb)化合物可如下列流程9中所示製備,其中E為H或C
1-C
6烷基、Hal為溴或碘,G為視需要地經取代的苯基或環丙基,及A*是氯、氟、三氟甲基或三氟甲氧基。
流程 9
使式(z)之含鹵素化合物與式(za)之硼酸反應以形成式(zb)化合物。例如,使式(z)之含鹵素化合物、硼酸(za)、適當觸媒(諸如[1,1’-雙(二苯膦基)二茂鐵]-二氯鈀(II)或乙酸鈀(II)與三環己基膦組合)、適當鹼(諸如碳酸銫、磷酸三鉀或碳酸氫鈉)在適當溶劑或溶劑混合物(諸如/含1,4-二㗁烷、乙醇、甲苯或水)中之混合物於範圍從約0至100℃的溫度下反應以提供式(zb)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。藉由用鹼金屬氫氧化物在適當溶劑或溶劑混合物(諸如/含四氫呋喃、乙醇或水)中於範圍從約0至100℃的溫度下處理,式(zb)化合物(其中E為C
1-C
6烷基)可轉化為式(zb)化合物(其中E為H)。
式(zf)化合物可如下列流程10中所示製備,其中Alk為C
1-C
6烷基和A為氯、氟或氰基。
流程 10
式(zc)之硼酸可藉由使用NaIO
4水解從已知的硼酸頻哪醇酯(WO 2011/023677、WO 2009/107391、WO 2010/069504)製備(Journal of Organic Chemistry, 79(1), 328-338, 2014)。
式(zc)之硼酸係反應至式(zd)之三氟甲硫基(trifluoromethylsulfanyl)化合物,其隨後與鹼氫氧化物反應以形成式(ze)之酸。接著將式(ze)化合物中之三氟甲硫基氧化以產生三氟甲磺醯基官能化的式(zf)化合物。
例如,使式(zc)之硼酸、三甲基(三氟甲基)矽烷、碳酸銀、磷酸三鉀、硫氰酸銅、1,10-啡啉、硫和4 Å分子篩之混合物在適當溶劑(諸如二甲基甲醯胺)中於範圍從約0至60℃的溫度下反應以提供式(zd)化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化(Angew. Chem. Int. Ed. 2012, 51, 2492 –2495)。使式(zd)之酯和鹼氫氧化物在含有例如水和四氫呋喃之適當溶劑混合物中於範圍從約0至100℃的溫度下反應以提供式(ze)之酸,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。使式(ze)之三氟甲硫基化合物、氯化釕(III)和過碘酸鈉,在含有例如二氯甲烷、乙腈和水之適當溶劑混合物中於範圍從約0至60℃的溫度下反應至式(zf)之三氟甲磺醯基化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
式(zj)化合物可如下列流程11中所示製備,其中R
1、R
3a、R
3b、R
4、R
5和Y係如先前所定義。
流程 11
使式(zg)之醯胺與式(g)之
N,N-二甲基醯胺二甲基縮醛反應以形成式(zh)化合物,其隨後與式(j)之經取代的肼在酸性條件下反應以形成式(zi)化合物。例如,使式(zg)化合物和式(g)之
N,N-二甲基醯胺二甲基縮醛在適當溶劑(諸如CH
2Cl
2)中於回流下反應以提供式(zh)化合物。移除溶劑後,使式(zh)化合物與式(j)之經取代的肼在適當溶劑(諸如1,4-二㗁烷、乙酸或該等溶劑之混合物)中於範圍從約20至80℃的溫度下反應。接著可將所得式(zi)化合物分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
將式(zi)之胺甲酸酯用酸處理以形成式(zj)之胺。例如,使式(zi)之胺甲酸酯和適當酸(諸如氯化氫或三氟乙酸)在適當溶劑(諸如二㗁烷)中或在三氟乙酸之情況下沒有另外的溶劑、於範圍從約0至80℃的溫度下反應。然後可以將所得的式(zj)之胺作為其鹼後處理的酸式鹽作為游離胺分離且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
所需要的式(zg)之醯胺和式(j)之肼為市售或可藉由本申請案中所述的方法或該項技術人員已知的方法合成。
式(zm)化合物可如下列流程12中所示製備,其中Alk為C
1-C
6烷基、Hal為碘或溴、Ra為C
1-C
6烷基、環丙基或視需要地經取代的苯基;及Rb為鹵素、C
1-C
6烷基或C
3-C
6環烷基。該苯基環可經最多兩個Rb取代基取代。
流程 12
使式(zk)之芳基鹵化物與式(zl)之亞磺酸鹽在銅催化下反應以形成式(zm)之碸。例如,使式(zk)化合物、式(zl)之亞磺酸鈉鹽、碘化銅(I)、脯胺酸和氫氧化鈉之混合物在適當溶劑(諸如二甲亞碸)中於範圍從40至140℃的溫度下反應。接著可將所得式(zm)分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。可藉由用鹼氫氧化物在適當溶劑或溶劑混合物(諸如/含四氫呋喃、乙醇或水)中於範圍從約0至100℃的溫度下處理將式(zm)之酯水解成羧酸。
所需要的芳基鹵化物(zk)和式(zl)之磺酸鹽為市售或或可藉由該項技術人員已知的方法合成。
式(zq)化合物可如下列流程13中所示製備,Hal為氟或氯,Rd為視需要地經取代的C
1-C
6烷基或視需要地經取代的C
3-C
6環烷基;及Rc為鹵素或在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基或C
1-C
4烷氧基。該苯基環可經最多兩個Rc取代基取代。
流程 13
使式(zn)之芳基鹵化物與式(zo)之硫醇鹽反應以形成式(zp)之硫醚,然後將其水解以形成式(zq)之羧酸。例如使式(zn)之鹵化物和式(zo)之硫醇鈉的混合物在適當溶劑(諸如N,N-二甲基甲醯胺)中於範圍從–20至50℃的溫度下反應。接著將所得式(zp)之腈在鹼性條件下使用例如氫氧化鈉水溶液在適當溶劑(諸如乙醇)中於範圍從40至100℃的溫度下或在酸性條件下在適當強酸(諸如硫酸或鹽酸,其為純的或用適當稀釋劑(諸如水)稀釋)中於範圍從40至100℃的溫度下水解。如果必要及需要的話,接著可使用該項技術中所熟知的技術(諸如層析法)將所得羧酸(zq)純化。
所需要的芳基鹵化物(zn)和式(zo)之硫醇鹽為市售或或可藉由該項技術人員已知的方法合成。
式I''b化合物可如下列流程14中所示製備,其中R
1、R
2、R
3a、R
3b、R
5和Y係如先前所定義。Bn為苯甲基和LG為氯離子或三氟甲磺醯基。
流程 14
將式(I''b)之經苯甲基保護的化合物去保護以形成式(I''c)之醇,接著用式(zr)之烷基化劑將其烷基化以形成式(I''d)之醚。例如,將式(I''b)之經苯甲基保護的化合物在適當觸媒(諸如鈀炭)存在下、在氫氛圍下、在適當溶劑(諸如甲醇)中於範圍從-20至50℃的溫度下去保護。接著用適當烷基化劑(諸如氯(二氟)甲烷(WO2016155884)或三氟甲烷磺酸二氟甲酯(WO2016046166))在適當鹼(諸如碳酸鉀或氫氧化鉀)存在下在適當溶劑(諸如乙腈或N,N-二甲基甲醯胺)中於範圍從-30至50℃的溫度下將所得式(I''b)之醇烷基化。如果必要且需要的話,接著使用該項技術中所熟知的技術(諸如層析法)將所得式(I''d)之醚進行純化。
所需要的式(I''b)之經苯甲基保護的化合物可如流程4中所示,使用可藉由該項技術人員已知的方法合成之肼製備(例如如J. Am. Chem. Soc. 2017, 139, 42, 14833-14836中所述)。
流程 15
流程15示出例如實施例I-091中所示之3-鹵烷基三唑的製備。在第一步驟,形成肼醯胺,如EP 1099695中所述。在第二步驟中,使(α
S)-1,3-二氫-α-甲基-1,3-二側氧基-2
H-異吲哚-2-乙醯氯(根據
Tetrahedron: Asymmetry,21(8), 936-942, 2010,從(α
S)-1,3-二氫-α-甲基-1,3-二側氧基-2H-異吲哚-2-乙酸(購自ABCR之Pht-Ala-OH)和草醯氯製備)與腙醯胺在鹼(如吡啶)存在下反應,如EP 1099695中所述。在第三步驟中,藉由與肼水合物在適當溶劑(如乙醇)中反應移除酞醯亞胺保護基團,如WO 2018086605中所述。在最後一步驟中,使所得的胺與羧酸反應以形成實施例化合物,例如I-091。例如,將胺、羧酸、適當偶合劑(諸如T3P
®、[
O-(7-氮雜苯并三唑-1-基)-
N,N,N′,N′-四甲基脲鎓-六氟磷酸鹽](HATU)、二環己基碳二亞胺(DCC)、1-乙基-3-(3-二甲胺基丙基)碳二亞胺(EDC)或羥基苯并三唑(HOBt)、適當鹼(諸如三乙胺或
N,N-二異丙基乙胺)在適當溶劑(諸如乙酸乙酯或
N,N-二甲基甲醯胺)中之混合物於範圍從約0至100℃的溫度下混合以提供實施例化合物,接著可將其分離,且如果必要及需要的話,使用該項技術中所熟知的技術(諸如層析法)純化。
式I''g和I''h化合物可如下列流程16中所示製備,其中R
1、R
2、R
3a、R
3b、R
5和Y係如先前所定義,T為如前所述的R
4且至少經一個-NO
2-基團取代,LG為適當脫離基和A表示視需要地經取代的C
1-C
6烷基、CO-C
1-C
6烷基、CO-C
3-C
6環烷基、CO-苯基、或SO
2C
1-C
6烷基。
流程16
在還原條件下,同樣用氫和鈀炭在適當溶劑(如THF或乙醇)(European Journal of Medicinal Chemistry, 158, 322-333;2018)中、用氯化錫(II)和HCl在適當溶劑(如乙醇)中(WO 2018085247)、用鐵粉和HCl在適當溶劑(如乙醇)中(WO 2017216293)或用鐵粉在乙酸和乙醇之混合物中,將式(I''e)之硝基化合物轉化成個別式(I''f)之胺基化合物。使所得胺基化合物(I''f)在適當鹼(諸如DIPEA或碳酸鉀)存在下與式(zs)之醯化、苯甲醯基化、磺化或烷基化試劑A-LG反應。若使用一當量的A-LG,則獲得式(I''g)化合物。二當量的A-LG產生式(I''h)化合物。如果必要且需要的話,接著使用該項技術中所熟知的技術(諸如層析法)將所得式(I''h)和(I''g)化合物純化。
式I''k化合物可如下列流程17中所示製備,其中R
1、R
2、R
3a、R
3b、R
5和Y係如先前所定義,其中T為如前所述的R
4且分別至少經一個–CO
2烷基-基團、-COOH或CON(E
1)E
2基團取代。E
1和E
2獨立地選自H和在各情況下視需要地經取代的C
1-C
6烷基、C
3-C
6環烷基、苯基或SO
2C
1-C
6烷基之群組。
流程 17
藉由熟習現有技術者已知的方法將式(I''i)之酯化合物皂化以獲得個別式(I''j)之羧酸化合物,接著與式(zt)胺的醯胺偶合步驟以獲得式(I''k)醯胺。
例如,式(zt)之胺、羧酸(I''j)、適當偶合劑(諸如T3P®、HATU、DCC或HOBt)、適當鹼(諸如三乙胺或DIPEA)在適當溶劑(諸如乙酸乙酯或DMF)中之混合物於範圍從約0至100℃的溫度下混合,以提供式(I''k)化合物,接著可將其分離,且如果必要及需要的話,可使用該項技術中所熟知的技術(諸如層析法)純化。
下列製備和使用例說明本發明而不是對其進行限制。
製備例 3- 氯 -N-( 環丙基甲基 )-5-( 甲磺醯基 )-N-{1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-003)
用0.30 mL (1.7 mmol)的N,N-二異丙基乙胺處理120 mg (491 µmol)的N-(環丙基甲基)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺和127 mg (541 µmol)的3-氯-5-(甲磺醯基)苯甲酸在5 mL的乙酸乙酯中之溶液並在室溫下攪拌10 min。添加0.60 mL (0.84 mmol)的T3P
®溶液(50 wt.%EtOAc溶液)並將反應混合物在室溫下攪拌過夜。加水,該等層分離並用乙酸乙酯萃取水層數次。將合併的有機層依次用水、NaHCO
3飽和水溶液和NH
4Cl飽和水溶液洗滌。將溶液用Na
2SO
4乾燥,過濾並在減壓下濃縮。藉由HPLC (H
2O / 乙腈)將殘餘物純化以提供125 mg的3-氯-N-(環丙基甲基)-5-(甲磺醯基)-N-{1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺。
1H-NMR(600.1 MHz, CD
3CN, 260 K): NMR峰列表:δ= 8.8859 (4.9); 8.8778 (5.0); 8.6382 (1.6); 8.6302 (1.6); 8.0865 (4.4); 8.0335 (1.4); 8.0142 (0.1); 7.9580 (2.7); 7.9433 (0.1); 7.9060 (0.1); 7.8124 (1.0); 7.7920 (0.1); 7.6327 (1.0); 7.5286 (1.4); 7.5206 (2.6); 7.5125 (1.4); 7.4498 (3.6); 7.4167 (0.5); 7.4088 (0.9); 7.4007 (0.5); 7.3889 (2.9); 6.3593 (0.4); 6.3477 (1.4); 6.3361 (1.5); 6.3246 (0.5); 6.0860 (0.2); 6.0749 (0.5); 6.0634 (0.5); 6.0517 (0.2); 3.8379 (0.3); 3.6910 (0.3); 3.6808 (0.3); 3.6675 (0.4); 3.6571 (0.4); 3.5278 (0.4); 3.5160 (0.4); 3.5040 (0.3); 3.4922 (0.3); 3.1910 (0.1); 3.1259 (0.4); 3.1151 (0.3); 3.0769 (16.0); 3.0244 (0.2); 2.9592 (0.1); 2.9111 (0.6); 2.9037 (0.4); 2.8995 (0.6); 2.8849 (1.3); 2.8733 (1.4); 2.8440 (1.3); 2.8345 (1.3); 2.8178 (0.6); 2.8083 (0.6); 2.3015 (0.1); 2.2910 (81.9); 2.2744 (0.2); 2.2645 (0.1); 2.2585 (0.1); 2.0800 (0.2); 2.0759 (0.4); 2.0718 (0.6); 2.0677 (0.4); 2.0636 (0.2); 1.9851 (1.2); 1.9770 (1.0); 1.9726 (1.7); 1.9692 (37.9); 1.9651 (74.7); 1.9609 (110.4); 1.9568 (76.7); 1.9527 (39.4); 1.9440 (0.9); 1.9348 (0.4); 1.9307 (0.3); 1.9268 (0.2); 1.9226 (0.2); 1.9182 (0.2); 1.9138 (0.2); 1.9096 (0.1); 1.8950 (0.1); 1.8916 (0.1); 1.8873 (0.1); 1.8831 (0.1); 1.8789 (0.1); 1.8748 (0.1); 1.8707 (0.1); 1.8622 (0.1); 1.8541 (0.3); 1.8500 (0.5); 1.8458 (0.7); 1.8417 (0.5); 1.8376 (0.3); 1.8232 (6.0); 1.8116 (6.1); 1.7615 (2.1); 1.7501 (2.1); 1.7134 (0.1); 1.7019 (0.1); 1.5085 (0.1); 1.3213 (0.2); 1.3132 (0.2); 1.3096 (0.2); 1.3006 (0.2); 1.2879 (0.2); 1.2766 (0.2); 1.2716 (0.2); 1.0585 (0.2); 1.0481 (0.3); 1.0378 (0.2); 0.8970 (0.2); 0.8858 (0.5); 0.8738 (0.2); 0.5974 (0.1); 0.5877 (0.2); 0.5837 (0.2); 0.5752 (0.5); 0.5643 (0.7); 0.5544 (0.6); 0.5418 (0.3); 0.5325 (0.1); 0.5107 (0.1); 0.4954 (0.4); 0.4817 (0.6); 0.4741 (0.6); 0.4681 (0.6); 0.4602 (0.4); 0.4523 (0.3); 0.4374 (0.1); 0.3496 (0.1); 0.3420 (0.2); 0.3336 (0.3); 0.3259 (0.4); 0.3209 (0.3); 0.3083 (0.3); 0.2991 (0.4); 0.2929 (0.7); 0.2851 (0.9); 0.2777 (0.8); 0.2702 (0.8); 0.2622 (1.1); 0.2528 (1.0); 0.2459 (0.9); 0.2398 (1.0); 0.2322 (0.7); 0.2254 (0.4); 0.2170 (0.2); 0.0967 (0.4); 0.0109 (0.2); 0.0054 (2.2); -0.0001 (84.9); -0.0057 (3.1); -0.0124 (1.5); -0.0265 (0.1); -0.0319 (0.1); -0.0376 (0.1); -0.0430 (0.1); -0.0580 (0.1); -0.0820 (0.1); -0.1002 (0.4); -0.1791 (0.3); -0.1875 (0.7); -0.1954 (1.0)。
ESI 質量 [m/z]:461.1 [M+H]
+ N-( 環丙基甲基 )-N-{1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3-[( 三氟甲基 ) 磺醯基 ] 苯甲醯胺的合成 ( 實施例 I-005)
用72 mg (0.33 mmol)的過碘酸鈉和接著用0.02 mg (0.1 µmol)的氯化釕(III)處理50 mg (111 µmol)的N-(環丙基甲基)-N-{1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-[(三氟甲基)氫硫基]苯甲醯胺、2 mL的二氯甲烷、2 mL的乙腈和4 mL的水之混合物。將反應混合物在室溫下攪拌1.5 h。添加水及二氯甲烷,該等層分離並用二氯甲烷萃取水層數次。將合併的有機層用Na
2SO
4乾燥,過濾並在減壓下濃縮以提供20 mg的N-(環丙基甲基)-N-{1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-[(三氟甲基)磺醯基]苯甲醯胺。
1H-NMR(600.1 MHz, CD
3CN, 260 K): NMR峰列表: δ= 9.0235 (0.2); 9.0154 (0.1); 8.9241 (0.4); 8.9161 (0.4); 8.9092 (0.3); 8.9011 (0.4); 8.8879 (0.9); 8.8764 (12.2); 8.8684 (12.2); 8.7211 (0.1); 8.7130 (0.1); 8.5912 (0.3); 8.5831 (0.5); 8.5723 (2.6); 8.5645 (2.6); 8.4517 (0.1); 8.3799 (0.1); 8.2586 (0.1); 8.2337 (0.1); 8.2199 (0.1); 8.1799 (0.2); 8.1638 (0.2); 8.1513 (0.1); 8.1383 (0.1); 8.1122 (3.6); 8.0990 (4.0); 8.0877 (11.2); 8.0726 (0.8); 8.0596 (0.6); 8.0393 (2.6); 8.0250 (1.0); 8.0122 (1.0); 7.9954 (0.1); 7.9814 (0.1); 7.9643 (0.1); 7.9586 (0.1); 7.9462 (0.2); 7.9321 (0.2); 7.9115 (1.8); 7.8855 (0.1); 7.8806 (0.1); 7.8713 (0.1); 7.8636 (0.1); 7.8547 (0.1); 7.7884 (2.8); 7.7754 (5.8); 7.7623 (3.3); 7.7223 (0.6); 7.7106 (1.6); 7.7034 (1.4); 7.6904 (1.3); 7.6755 (4.9); 7.6624 (3.7); 7.6295 (6.8); 7.6139 (0.1); 7.5380 (0.2); 7.5276 (0.3); 7.5165 (3.4); 7.5084 (6.4); 7.5004 (3.2); 7.4879 (0.2); 7.4743 (0.2); 7.4507 (0.5); 7.4369 (0.4); 7.3810 (0.9); 7.3734 (1.4); 7.3656 (0.7); 6.5009 (0.1); 6.4358 (0.1); 6.4239 (0.2); 6.4066 (1.2); 6.3951 (3.8); 6.3835 (3.8); 6.3719 (1.2); 6.2934 (0.1); 6.2818 (0.1); 6.1368 (0.1); 6.1334 (0.1); 6.0337 (0.3); 6.0227 (0.9); 6.0113 (0.9); 6.0002 (0.3); 5.9466 (0.1); 5.9354 (0.1); 5.6189 (0.1); 5.6035 (0.1); 5.4721 (9.8); 5.3607 (0.3); 5.3524 (0.5); 5.3443 (0.3); 5.3369 (0.1); 5.3189 (0.1); 3.7124 (0.1); 3.6988 (0.1); 3.6872 (0.6); 3.6767 (0.6); 3.6635 (0.7); 3.6531 (0.7); 3.5619 (0.1); 3.5496 (0.1); 3.5375 (0.1); 3.4961 (0.7); 3.4845 (0.7); 3.4722 (0.6); 3.4607 (0.6); 3.4443 (0.1); 3.4363 (0.1); 3.4337 (0.1); 3.4258 (0.1); 3.2372 (0.1); 3.2270 (0.1); 3.2162 (0.1); 3.1097 (0.1); 3.0986 (0.1); 3.0329 (0.5); 3.0220 (0.8); 3.0115 (0.5); 3.0015 (0.1); 2.9900 (0.2); 2.9792 (0.1); 2.9472 (0.1); 2.9183 (0.3); 2.9104 (0.3); 2.8935 (0.1); 2.8817 (0.1); 2.8719 (0.3); 2.8671 (0.3); 2.8612 (0.3); 2.8454 (9.0); 2.8349 (9.8); 2.8193 (0.4); 2.8088 (0.1); 2.8035 (0.1); 2.7934 (0.1); 2.7793 (0.1); 2.7300 (0.5); 2.6637 (0.6); 2.5973 (0.1); 2.3290 (0.1); 2.3232 (0.1); 2.3147 (0.2); 2.2914 (121.5); 2.2685 (0.2); 2.2560 (0.3); 2.2479 (0.1); 2.2427 (0.1); 2.1918 (0.1); 2.1103 (0.5); 2.0978 (1.0); 2.0851 (0.6); 2.0801 (0.4); 2.0760 (0.7); 2.0719 (1.0); 2.0678 (0.7); 2.0637 (0.4); 2.0497 (0.1); 2.0456 (0.1); 2.0324 (0.2); 2.0210 (0.6); 2.0114 (0.6); 2.0001 (0.4); 1.9925 (0.2); 1.9852 (1.6); 1.9771 (2.6); 1.9692 (61.6); 1.9651 (119.3); 1.9610 (175.6); 1.9569 (122.8); 1.9529 (63.2); 1.9354 (0.3); 1.9262 (0.2); 1.9229 (0.2); 1.9180 (0.2); 1.8958 (0.1); 1.8917 (0.1); 1.8870 (0.1); 1.8830 (0.1); 1.8780 (0.1); 1.8736 (0.1); 1.8687 (0.1); 1.8540 (0.5); 1.8501 (0.8); 1.8459 (1.2); 1.8418 (1.1); 1.8292 (15.8); 1.8176 (16.0); 1.7871 (0.2); 1.7838 (0.2); 1.7491 (3.9); 1.7377 (3.8); 1.7109 (0.2); 1.7000 (0.1); 1.6931 (0.1); 1.6813 (0.1); 1.6756 (0.1); 1.6602 (0.1); 1.6408 (0.1); 1.6271 (0.1); 1.6043 (0.1); 1.5882 (0.1); 1.5350 (0.2); 1.5249 (0.6); 1.5134 (0.6); 1.5001 (0.3); 1.4780 (0.1); 1.4701 (0.1); 1.4580 (0.1); 1.4486 (0.1); 1.4441 (0.1); 1.4279 (0.1); 1.4208 (0.1); 1.4108 (0.4); 1.4029 (0.2); 1.3906 (0.2); 1.3771 (0.1); 1.3630 (0.2); 1.3517 (0.2); 1.3408 (0.9); 1.3086 (0.8); 1.2826 (2.9); 1.2601 (9.1); 1.2169 (0.2); 1.2069 (0.2); 1.1912 (0.4); 1.1758 (0.2); 1.1598 (0.2); 1.1519 (0.1); 1.1420 (0.1); 1.1358 (0.1); 1.1246 (0.4); 1.1098 (0.1); 1.0974 (0.1); 1.0942 (0.1); 1.0852 (0.5); 1.0737 (1.6); 1.0617 (0.4); 1.0506 (0.6); 1.0463 (1.8); 1.0403 (1.6); 1.0294 (1.5); 1.0204 (0.9); 0.9820 (0.1); 0.9688 (0.2); 0.9578 (0.2); 0.9493 (0.2); 0.9452 (0.2); 0.9372 (0.2); 0.9327 (0.2); 0.9246 (0.3); 0.9168 (0.2); 0.9124 (0.2); 0.8927 (1.1); 0.8816 (2.2); 0.8697 (1.2); 0.8528 (0.5); 0.8404 (0.3); 0.8151 (0.1); 0.8045 (0.2); 0.7922 (0.1); 0.7816 (0.1); 0.7654 (0.1); 0.5550 (0.2); 0.5415 (0.7); 0.5320 (1.6); 0.5225 (2.2); 0.5121 (1.7); 0.4997 (0.9); 0.4890 (0.5); 0.4801 (0.6); 0.4641 (1.1); 0.4570 (1.5); 0.4434 (1.2); 0.4346 (0.7); 0.4222 (0.2); 0.3916 (0.1); 0.3844 (0.1); 0.3712 (0.1); 0.3638 (0.1); 0.3564 (0.1); 0.3392 (0.3); 0.3317 (0.5); 0.3236 (0.7); 0.3157 (0.8); 0.2837 (0.1); 0.2734 (0.2); 0.2602 (0.6); 0.2515 (1.0); 0.2451 (1.9); 0.2369 (2.6); 0.2299 (2.7); 0.2228 (2.4); 0.2150 (2.9); 0.2066 (2.4); 0.1995 (2.3); 0.1932 (2.5); 0.1842 (2.0); 0.1721 (1.0); 0.0970 (0.1); 0.0786 (0.2); 0.0243 (0.1); 0.0183 (0.1); 0.0054 (0.6); -0.0001 (19.3); -0.1005 (0.1); --0.2529 (0.8); -0.2613 (1.9); -0.2693 (2.7); -0.2772 (2.8); -0.2847 (2.1); -0.2926 (0.8); -0.4435 (0.9); -0.4514 (2.2); -0.4590 (2.8); -0.4670 (2.6); -0.4751 (1.8); -0.4833 (0.7)。
ESI 質量 [m/z]:481.1 [M+H]
+ 3- 氯 -5-( 環丙基胺甲醯基 ) 苯甲酸
將0.80 g (3.98 mmol)的5-氯異酞酸、1.82 g (4.78 mmol)的1-[雙(二甲基胺基)亞甲基]-1
H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)和0.83 mL(4.8 mL)的N,N-二異丙基乙胺在二氯甲烷中之溶液在室溫下攪拌10 min並接著用0.28 mL(4.0 mmol)的環丙胺處理。將混合物在室溫下攪拌過夜。在減壓下蒸發溶劑並藉由HPLC (H
2O / 乙腈)將殘餘物純化以提供286 mg的3-氯-5-(環丙基胺甲醯基)苯甲酸。
1H-NMR(400.2 MHz, d
6-DMSO): NMR峰列表; δ= 13.5637 (0.4); 8.7486 (4.5); 8.7384 (4.5); 8.6590 (0.4); 8.6491 (0.4); 8.3479 (8.7); 8.3442 (16.0); 8.3404 (9.1); 8.2041 (0.6); 8.2002 (0.3); 8.1020 (8.3); 8.0971 (12.8); 8.0928 (9.1); 8.0221 (9.5); 8.0184 (11.4); 8.0172 (11.0); 8.0133 (8.3); 7.9664 (1.2); 7.9626 (1.2); 3.3349 (4.9); 2.9095 (0.7); 2.8993 (2.1); 2.8895 (2.8); 2.8811 (4.6); 2.8709 (4.7); 2.8629 (2.8); 2.8528 (2.3); 2.8426 (0.9); 2.6789 (0.4); 2.6744 (0.6); 2.6698 (0.4); 2.5278 (1.6); 2.5230 (2.6); 2.5144 (35.4); 2.5099 (72.7); 2.5053 (95.3); 2.5007 (67.5); 2.4962 (31.8); 2.3368 (0.4); 2.3321 (0.6); 2.3276 (0.4); 2.0772 (5.6); 0.7363 (2.8); 0.7234 (6.7); 0.7181 (10.9); 0.7065 (9.2); 0.6996 (8.1); 0.6889 (4.3); 0.6683 (0.8); 0.6587 (0.7); 0.6501 (1.1); 0.6197 (4.2); 0.6093 (11.3); 0.6012 (9.3); 0.5993 (9.0); 0.5943 (6.9); 0.5915 (6.9); 0.5809 (3.0); 0.1459 (0.4); 0.0133 (0.3); 0.0079 (3.6); -0.0002 (107.9); -0.0086 (3.6); -0.1497 (0.4)。
ESI 質量 [m/z]:240.2 [M+H]
+ 4'- 氟 -5-( 三氟 甲基 )[ 聯苯 ]-3- 甲酸
將400 mg (1.48 mmol)的3-溴-5-(三氟甲基)苯甲酸、250 mg (1.78 mmol)的(4-氟苯基)硼酸、109 mg (140 µmol)的[1,1′-雙(二苯膦基)二茂鐵]-二氯鈀(II)、969 mg (2.97 mmol)的碳酸銫、3.1 mL的1,4-二㗁烷和0.75 mL的乙醇之混合物在80℃下加熱2 h。然後將反應混合物經矽藻土過濾,用乙醇洗滌。將濾液在減壓下濃縮,用1M HCl水溶液處理並用乙酸乙酯萃取幾次。將合併的有機層用鹽水洗滌,用Na
2SO
4乾燥並在減壓下濃縮。將殘餘物從二氯甲烷中再結晶,產生316 mg的4'-氟-5-(三氟甲基)[聯苯]-3-甲酸。
1H-NMR(400.2 MHz, d
6-DMSO): NMR峰列表: δ= 13.6540 (1.8); 8.4111 (10.5); 8.2400 (9.6); 8.1578 (10.0); 7.8932 (7.8); 7.8882 (3.7); 7.8798 (8.7); 7.8713 (9.3); 7.8630 (3.8); 7.8579 (8.3); 7.8503 (1.0); 7.3862 (1.0); 7.3785 (8.5); 7.3564 (16.0); 7.3393 (2.8); 7.3343 (7.7); 7.3269 (0.9); 4.0389 (0.5); 4.0211 (0.5); 3.3310 (18.2); 2.6778 (0.8); 2.6734 (1.0); 2.6693 (0.8); 2.5090 (131.2); 2.5046 (168.3); 2.5002 (125.9); 2.3357 (0.8); 2.3313 (1.0); 2.3271 (0.8); 1.9902 (2.0); 1.1940 (0.5); 1.1762 (1.1); 1.1584 (0.5); 0.1460 (0.5); 0.0077 (4.5); -0.0002 (100.7); -0.0083 (4.6); -0.1496 (0.5).。
ESI 質量 [m/z]:283.1 [M-H]
- 3- 環丙基 -5-( 三氟甲基 ) 苯甲酸甲酯
藉由用氬氣吹掃將1.00 g (3.53 mmol)的3-溴-5-(三氟甲基)苯甲酸甲酯、334 mg (3.88 mmol)的環丙基硼酸、891 mg (10.6 mmol)的NaHCO
3在8 mL的1,4-二㗁烷和4 mL的H
2O中之混合物除氣。添加129 mg (176 µmol)的[1,1′-雙(二苯膦基)二茂鐵]-二氯鈀(II)。將混合物在100℃下加熱10 h之前,藉由用氬氣吹掃將其再次除氣。在減壓下濃縮混合物。添加水和二氯甲烷,該等層分離並用二氯甲烷萃取水層數次。將合併的有機層用Na
2SO
4乾燥,過濾並在減壓下濃縮。藉由HPLC (H
2O / 乙腈)將殘餘物純化以提供23 mg的3-環丙基-5-(三氟甲基)苯甲酸甲酯。
1H-NMR(400.2 MHz, d
6-DMSO): NMR峰列表: δ= 7.9431 (2.1); 7.8956 (2.3); 7.7295 (2.1); 3.8896 (16.0); 3.8753 (0.6); 3.3255 (10.1); 2.5264 (0.4); 2.5129 (8.4); 2.5088 (16.6); 2.5043 (21.5); 2.4998 (15.6); 2.4956 (7.8); 2.2086 (0.6); 2.2002 (0.6); 2.1965 (0.4); 2.1877 (1.2); 2.1752 (0.7); 2.1667 (0.6); 1.0928 (0.7); 1.0813 (1.9); 1.0759 (2.0); 1.0650 (1.0); 1.0603 (2.0); 1.0549 (1.9); 1.0442 (0.8); 0.8501 (0.8); 0.8387 (2.3); 0.8340 (2.1); 0.8267 (2.0); 0.8216 (2.4); 0.8098 (0.7); 0.0078 (0.5); -0.0002 (13.4); -0.0082 (0.6)。
ESI 質量 [m/z]:245.1 [M]
+ 3- 氯 -5-[( 三氟甲基 ) 氫硫基 ] 苯甲酸 的合成 步驟 1 : [3- 氯 -5-( 甲氧基羰基 ) 苯基 ] 硼酸
將17.3 g (80.9 mmol)的過碘酸鈉和6.24 g (80.9 mmol)的乙酸銨加至12 g (40 mmol)的3-氯-5-(4,4,5,5-四甲基-1,3,2-二氧雜硼雜環戊烷(dioxaborolan)-2-基)苯甲酸甲酯在30 mL的丙酮和30 mL的H
2O中之懸浮液。將混合物在25℃下攪拌2 h並接著通過矽藻土過濾。蒸發濾液。將殘餘物用200 mL的乙酸乙酯稀釋,並用100 mL的H
2O洗滌。將有機相用鹽水洗滌,用無水Na
2SO
4乾燥,過濾並在真空中濃縮。將粗製產物與10 mL的石油醚在15℃下研磨20 min。過濾混合物,將殘餘物在減壓下乾燥以獲得7 g的呈白色固體之[3-氯-5-(甲氧基羰基)苯基]硼酸。
1H-NMR (400 MHz, CDCl
3): δ = 8.72 (s, 1H), 8.35 (s, 1H), 8.27 (s, 1H), 4.02 (s, 3H)。參考痕量 CHCl
3在7.25 ppm處之訊號。使用Varian 400MR NMR機器測量。
步驟 2 : 3- 氯 -5-[( 三氟甲基 ) 氫硫基 ] 苯甲酸甲酯
將在500 mL的DMF中之13 g (61 mmol)的[3-氯-5-(甲氧羰基)苯基]硼酸、43.1 g (303 mmol)的三甲基(三氟甲基)矽烷、33.4 g (121 mmol)的Ag
2CO
3、38.6 g (182 mmol)的K
3PO
4、762 mg (6.06 mmol)的CuSCN、2.2 g (12 mmol)的1,10-啡啉、46.7 g (1.46 mol)的硫和13 g的4 Å 分子篩在N
2下於25℃攪拌16 h。將混合物通過矽藻土過濾。將濾液用1.5 L的甲基三級丁基醚稀釋並用2 x 500 mL H
2O洗滌。將有機相用鹽水洗滌,用無水Na
2SO
4乾燥,過濾並在真空中濃縮。藉由MPLC在矽膠上(石油醚:乙酸乙酯 = 1 :0 ~ 20 :1)將粗製產物純化以獲得5.5 g呈淡黃色油之3-氯-5-[(三氟甲基)氫硫基]苯甲酸甲酯。
1H-NMR (400 MHz, CDCl
3): δ =8.20 (s, 1H), 8.10 – 8.15 (m, 1H), 7.83 (s, 1H), 3.96 (s, 3H)。參考痕量CHCl
3在7.25 ppm處之訊號。使用Varian 400MR NMR機器測量。
步驟 3 : 3- 氯 -5-[( 三氟甲基 ) 氫硫基 ] 苯甲酸
將5.5 g (20 mmol) 3-氯-5-[(三氟甲基)氫硫基]苯甲酸甲酯溶解在12 mL四氫呋喃和12 mL H
2O之混合物中。將1.63 g (40.6 mmol)的NaOH加至混合物,然後將其在25℃下攪拌2h。藉由添加40 mL 1 M HCl將混合物調整至pH 5並用150 mL乙酸乙酯萃取。將有機相用鹽水洗滌,用無水Na
2SO
4乾燥,過濾並在真空中濃縮。將粗製產物與50 mL石油醚在25℃下一起研磨15 min。過濾混合物,並在減壓下乾燥殘餘物以獲得3.0 g呈黃色固體之3-氯-5-(三氟甲基氫硫基)苯甲酸。
1H-NMR (400 MHz, CDCl
3): δ =11.28 (br s, 1H), 8.29 (s, 1H), 8.20 – 8.25 (m, 1H), 7.91 (s, 1H)。參考痕量CHCl
3在7.25 ppm處之訊號。使用Varian 400MR NMR機器測量。
ESI 質量 [m/z]:254.8 [M-H]
-
藉由LC-MS的測定係使用流動相乙腈和10mM碳酸氫銨水溶液進行;線性梯度從15%乙腈至90%乙腈,流率0.80 ml/min;儀器:Agilent 1200 & Agilent 6120。用於層析法之管柱為2.1*50mm Xbridge Shield RPC18 管柱 (5µm粒子)。檢測方法為二極體陣列(DAD)和蒸發光散射(ELSD)檢測以及負電噴灑游離。
3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[( 三氟甲基 ) 磺醯基 ] 苯甲醯胺的合成 ( 實施例 I-033) 步驟 1 : 3- 氯 -5-[( 三氟甲基 ) 磺醯基 ] 苯甲酸
將1 g (3.89 mmol)3-氯-5-[(三氟甲基)氫硫基]苯甲酸溶解在20 mL二氯甲烷、20 mL乙腈和20 mL的水之混合物中。將2.5 g (11.6 mmol)過碘酸鈉和0.81 mg (3.9 µmol)氯化釕(III)加至混合物,然後其在室溫下攪拌90 min。藉由加水稀釋混合物並用二氯甲烷萃取。將有機相以無水Na
2SO
4乾燥,過濾和在真空中濃縮以獲得1.2 g的呈無色固體之目標化合物。將粗製產物原樣使用於下一步驟中。
1H-NMR (400 MHz, d
6-DMSO): δ = 14.27 – 14.20 (br s, 1H), 8.51 (s, 1H), 8.49 (s, 1H), 8.38 (s, 1H)。
ESI 質量 [m/z]:287.0 [M-H]
- 步驟 2 : N-[(2S)-1- 胺基 -1- 側氧丙 -2- 基 ]-3- 氯 -5-[( 三氟甲基 ) 磺醯基 ] 苯甲醯胺
將1.2 g (來自步驟1的粗製物,4.15 mmol)溶解在20 mL二氯甲烷中,添加二滴DMF和0.43 mL(4.98 mmol)草醯氯。將混合物在室溫下攪拌5 h。在減壓下移除二氯甲烷和過量草醯氯並將剩餘的殘餘物用50 mL二氯甲烷稀釋及添加1.03 g (8.3 mmol) (2S)-2-胺基丙醯胺鹽酸鹽。在5分鐘內滴加2.31 mL(16 mmol)三乙胺。將混合物在室溫下攪拌1 h,以薄層層析法監測。將混合物在真空中濃縮,用水稀釋並用二氯甲烷萃取。將有機相用無水Na
2SO
4乾燥,過濾和在真空中濃縮。藉由層析法(梯度環己烷 / 乙酸乙酯)將剩餘的殘餘物純化以獲得1.1 g的呈無色固體之目標化合物。
1H NMR (400 MHz, d6-DMSO): δ = 9.13 - 9.11 (d, 1H, NH), 8.61 (s, 1H), 8.54 (s, 1H), 8.41 (s, 1H), 7.50 (br s, 1H from NH
2), 7.05 (br s, 1H from NH
2), 4.46 - 4.39 (m, 1H), 1.36 - 1.35 (d, 3H)。
ESI 質量 [m/z]:358.9 [M+H]
+ 步驟 3 : 3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[( 三氟甲基 ) 磺醯基 ] 苯甲醯 胺 ( 實施例 I-033)
將1.1 g (81.6 %純度,2.53 mmol)的N-[(2S)-1-胺基胺基-1-側氧丙-2-基]-3-氯-5-[(三氟甲基)磺醯基]苯甲醯胺溶解在20 mL二氯甲烷中。添加447 mg (3.75 mmol) N,N-二甲基甲醯胺二甲基縮醛,並將反應混合物回流90分鐘。在減壓下移除溶劑,並將剩餘的殘餘物溶解在20 mL二㗁烷和3 mL中乙酸之混合物中。添加336 mg (3.05 mmol) 2-肼基嘧啶。將反應混合物在50℃下攪拌過夜,在真空中濃縮並用水和乙酸乙酯稀釋。將分離的有機相用碳酸氫鈉水溶液洗滌,用無水Na
2SO
4乾燥,過濾和在真空中濃縮。藉由pHPLC將剩餘的殘餘物純化以獲得0.3 g 呈無色固體之3-氯-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-5-[(三氟甲基)磺醯基]苯甲醯胺。
1H-NMR (400 MHz, d6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:460.9 [M+H]
+ 3- 氯 -5-( 甲磺醯基 )-N-{1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-020)
將4.00 g (11.8 mmol) 2-[5-(1-溴乙基)-1H-1,2,4-三唑-1-基]嘧啶用40 mL的在甲醇中之氨溶液(7 M,0.3 mol)處理。將混合物在室溫下攪拌過夜。接著再添加20 mL的在甲醇中之氨溶液(7 M,0.14 mol)並繼續攪拌直至藉由HPLC分析觀察到起始材料完全轉化。在減壓下濃縮反應混合物且殘餘物未經進一步純化而使用。
將5 mL乙腈、365 mg (960 µmol) 1-[雙(二甲胺基)亞甲基]-1
H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)和0.19 mL (1.4 mmol) N,N-二異丙基乙胺加至136 mg (580 µmol) 3-氯-5-(甲磺醯基)苯甲酸。將混合物在室溫下攪拌1 h。接著添加來自前述步驟之200 mg的含有1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺之殘餘物。將反應混合物在室溫下攪拌過夜,然後藉由HPLC (H
2O / 乙腈)純化以提供64 mg的3-氯-5-(甲磺醯基)-N-{1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:407.1 [M+H]
+ (1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙胺鹽酸鹽的合成 步驟 1 : {(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 胺甲酸三級丁酯
將4.97 mL(37.5 mmol) N,N-二甲基甲醯胺二甲基縮醛加至4.78 g (25.3 mmol) N
2-(三級丁氧羰基)-L-丙胺醯胺在100 mL的CH
2Cl
2中之溶液。將溶液在回流下加熱2 h,之後在真空中移除溶劑。將殘餘物溶解在45 mL 1,4-二㗁烷和45 mL冰醋酸之混合物中。添加3.41 g (31 mmol) 2-肼基嘧啶並將混合物在50℃下攪拌45 min。在減壓下移除溶劑,添加NaHCO
3的飽和水溶液並將混合物用乙酸乙酯重複萃取。將合併的有機層用Na
2SO
4乾燥並在減壓下移除溶劑。藉由逆相層析法(H
2O / 乙腈)將殘餘物純化以提供4.51 g的{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}胺甲酸三級丁酯。
1H NMR (DMSO-d
6, 400 MHz): NMR峰列表: δ= 9.0011 (3.9); 8.9890 (3.9); 8.1196 (2.5); 7.6599 (2.2); 7.6477 (4.2); 7.6356 (2.1); 7.4658 (0.7); 7.4465 (0.7); 5.5270 (0.5); 5.5091 (0.7); 5.4910 (0.5); 3.3264 (15.3); 2.5262 (0.3); 2.5214 (0.6); 2.5127 (8.5); 2.5083 (17.6); 2.5037 (23.5); 2.4992 (17.0); 2.4948 (8.1); 2.0759 (10.4); 1.4486 (3.8); 1.4312 (3.5); 1.2827 (16.0); 1.0275 (0.9); -0.0002 (7.8)。
ESI 質量 [m/z]:235.2 [M-C
4H
8+H]
+ 步驟 2 : (1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙胺鹽酸鹽
將17 mL的HCl在1,4-二㗁烷中之4 M溶液加至2.0 g (6.9 mmol) {(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}胺甲酸三級丁酯在40 mL的1,4-二㗁烷中之溶液。將混合物在50℃下攪拌4 h並在室溫下過夜。在減壓下移除溶劑以提供1.74 g的含有(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽之殘餘物。此未經進一步純化而使用。
1H NMR (DMSO-d
6, 400 MHz): NMR 峰列表:δ= 9.0360 (15.7); 9.0238 (16.0); 8.7967 (0.4); 8.7061 (3.5); 8.3670 (13.0); 7.6975 (4.2); 7.6853 (8.0); 7.6731 (4.1); 5.3554 (0.4); 5.3411 (1.2); 5.3263 (1.5); 5.3108 (1.2); 5.2960 (0.5); 4.1434 (0.4); 4.1253 (0.8); 4.1107 (2.1); 4.0899 (0.4); 4.0210 (1.2); 3.8777 (0.9); 3.8698 (0.8); 3.8623 (0.9); 3.8418 (0.8); 3.8335 (0.7); 3.8212 (0.6); 3.7300 (0.3); 3.7252 (0.3); 3.7144 (0.5); 3.7104 (0.4); 3.7006 (0.6); 3.6806 (0.6); 3.6709 (0.4); 3.6668 (0.5); 3.5683 (5.6); 3.5139 (0.3); 3.5048 (1.1); 3.4994 (1.5); 3.4958 (1.6); 3.4903 (1.5); 3.4837 (0.4); 3.4742 (0.6); 3.4660 (0.9); 3.4486 (2.4); 3.4311 (2.4); 3.4136 (0.8); 3.3886 (3.4); 2.6770 (0.5); 2.6725 (0.6); 2.6681 (0.5); 2.5259 (1.8); 2.5212 (2.8); 2.5125 (38.7); 2.5081 (79.6); 2.5036 (104.8); 2.4990 (74.8); 2.4946 (35.9); 2.3350 (0.4); 2.3303 (0.6); 2.3260 (0.5); 1.6495 (14.5); 1.6327 (14.3); 1.5476 (0.6); 1.5305 (0.6); 1.2164 (0.8); 1.1985 (1.7); 1.1808 (0.8); 1.1400 (0.4); 1.0728 (2.4); 1.0554 (4.7); 1.0379 (2.3); -0.0001 (4.9)。
ESI 質量 [m/z]:191.2 [M+H]
+ 3- 氯 -N- 乙基 -5-( 甲磺醯基 )-N-{1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-040) 步驟 1 : N- 乙基 -1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙胺
將500 mg(1.86 mmol)的2-[5-(1-溴乙基)-1H-1,2,4-三唑-1-基]嘧啶(從WO 2017192385得知)溶解在30 mL乙腈中。接著添加775 mg (5.60 mmol)碳酸鉀和1.87 mL的乙胺在THF中之2
M溶液。將反應混合物加熱至回流二小時。冷卻後,將反應混合物經由Celite®過濾,用乙腈洗滌濾餅,在減壓下蒸發濾液,以獲得450 mg的目標化合物,其原樣使用於下一步驟中。
1H NMR (DMSO-d
6, 400 MHz): 9.00 – 8.99 (d, 2H), 8.14 (s, 1H), 7.66 – 7.64 (t, 1H), 4.67 – 4.57 (broad m, 1H), 2.34 – 2.31 (broad m, 2H), 2.04 (broad s, 1H, NH), 1.40 – 1.38 (d, 3H), 0.86 – 0.82 (t, 3H)。
ESI 質量 [m/z]:219.3 [M+H]
+ 步驟 2 : 3- 氯 -N- 乙基 -5-( 甲磺醯基 )-N-{1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 ( 實施例 I-040)
將449 mg (1.77 mmol)的N-乙基-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺溶解在20 mL乙腈中接著是0.462 mL (2.65 mmol)的DIPEA。向此反應混合物,滴加溶解在21 mL乙腈中之448 mg (1.77 mmol)的3-氯-5-(甲磺醯基)苯甲醯氯。將反應混合物在室溫下攪拌過夜,接著在減壓下蒸發溶劑。在藉由逆相層析法(H
2O / 乙腈)之純化之後獲得目標化合物。產率:470 mg (產率:61 %)。
1H NMR (DMSO-d
6, 400 MHz, 260K):參見表1中之NMR峰列表。
ESI 質量 [m/z]:435.1 [M+H]
+ 3- 氯 -5-( 乙磺醯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-044) 步驟 1 : 3- 氯 -5-( 乙磺醯基 ) 苯甲酸
藉由用氬氣吹掃將0.47 g(4.1 mmol) 脯胺酸和0.16 g (4.0 mmol)氫氧化鈉在24 mL二甲亞碸中之混合物除氣30 min。添加1.5 g (5.1 mmol) 3-氯-5-碘苯甲酸甲酯、4.7 g (40 mmol) 乙亞磺酸鈉和0.77 g (4.0 mmol) 碘化銅(I)和用氬氣將混合物再吹掃5 min。將混合物在120℃下攪拌3 h,冷卻至室溫並接著用4 mL的2 M氫氧化鈉水溶液處理。將其在室溫下進一步攪拌過夜,冷卻至10℃並用濃鹽酸酸化至pH 1。將水加至該混合物並用乙酸乙酯將其萃取。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用水洗滌兩次並用鹽水洗滌一次及接著用Na
2SO
4乾燥。在減壓下移除溶劑並藉由逆相層析法(H
2O / 乙腈)將殘餘物純化以提供1.00 g的3-氯-5-(乙磺醯基)苯甲酸。
1H NMR (DMSO-d
6, 400 MHz):NMR 峰列表:δ= 8.2775 (3.5); 8.2737 (6.8); 8.2698 (4.4); 8.2363 (3.4); 8.2325 (4.0); 8.2313 (5.4); 8.2277 (4.1); 8.2090 (4.8); 8.2046 (5.5); 8.1997 (3.0); 3.4891 (1.9); 3.4707 (6.7); 3.4523 (6.8); 3.4340 (2.1); 3.3298 (6.3); 2.5259 (0.6); 2.5212 (1.0); 2.5125 (17.2); 2.5080 (36.2); 2.5034 (48.0); 2.4988 (33.7); 2.4942 (15.6); 1.1402 (6.9); 1.1219 (16.0); 1.1034 (6.8); -0.0002 (5.1)。
ESI 質量 [m/z]:247.1 [M-H]
- 步驟 2 : 3- 氯 -5-( 乙磺醯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 ( 實施例 I-044)
將10 mL乙腈、936 mg (2.47 mmol) N,N,N′,N′-四甲基-O-(1H-苯并三唑-1-基)脲鎓六氟磷酸鹽(HBTU)和0.48 mL (3.7 mmol)
N,N-二異丙基乙胺加至369 mg (1.48 mmol)的3-氯-5-(乙磺醯基)苯甲酸。將混合物在室溫下攪拌1 h。接著添加280 mg (1.23 mmol)的(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽。在藉由逆相層析法(H
2O / 乙腈)將反應混合物純化以提供270 mg的3-氯-5-(乙磺醯基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺之前,將其在室溫下攪拌過夜。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:421.1 [M+H]
+ N-( 環丙基甲基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3-[( 三氟 - 甲基 ) 磺醯基 ] 苯甲醯胺的合成 ( 實施例 I-047)
將100 mg (0.44 mmol) (1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽在2.2 mL四氫呋喃中之溶液用31 µL (0.41 mmol)環丙基甲醛處理。5 min之後添加140 mg (0.66 mmol)三乙醯氧基硼氫化鈉並將混合物在室溫下攪拌過夜。將2 mL的NaHCO
3之飽和水溶液和2 mL乙酸乙酯加至混合物並繼續攪拌30 min。再添加10 mL飽和NaHCO
3水溶液並將混合物用乙酸乙酯重複萃取。將合併的有機層用Na
2SO
4乾燥和在減壓下移除溶劑以提供82 mg的含有(1S)-N-(環丙基甲基)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺之殘餘物。
將69 mg (0.26 mmol) 3-[(三氟甲基)磺醯基]苯甲酸、2.4 mL乙酸乙酯、0.15 mL (0.85 mmol)
N-乙基二異丙胺和0.29 mL (0.41 mmol)的T3P
®溶液(50 wt. % EtOAc溶液)加至在前述步驟中所得之殘餘物。將混合物在室溫下攪拌過夜。在減壓下移除溶劑並藉由層析法在矽石上(梯度環己烷 / 乙酸乙酯)和藉由逆相層析法(H
2O / 乙腈)將殘餘物純化以提供12 mg N-(環丙基甲基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-[(三氟甲基)磺醯基]苯甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:481.2 [M+H]
+ 3- 氯 -5-( 異丙磺醯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-051) 步驟 1 : 3- 氯 -5-( 異丙硫基 ) 苯甲腈
將1.00 g (6.42 mmol) 3-氯-5-氟苯甲腈和820 mg (8.35 mmol) 丙烷-2-硫醇鈉在20 mL的
N,N-二甲基甲醯胺中之溶液在室溫下攪拌過夜。將0.74 mL冰醋酸加至混合物並在減壓下移除揮發物。將水和乙酸乙酯加至殘餘物。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用鹽水洗滌並接著用Na
2SO
4乾燥。在減壓下移除溶劑並藉由逆相層析法(H
2O / 乙腈)將殘餘物純化以提供589 mg的3-氯-5-(異丙硫基)苯甲腈。
1H-NMR (400 MHz, d
6-DMSO):NMR 峰列表:δ= 7.8514 (1.3); 7.8469 (2.2); 7.8433 (1.7); 7.8148 (1.5); 7.8109 (2.7); 7.8075 (1.6); 7.7554 (1.7); 7.7508 (2.7); 7.7464 (1.4); 3.8055 (0.4); 3.7890 (1.0); 3.7724 (1.4); 3.7558 (1.0); 3.7393 (0.4); 3.3253 (10.3); 2.5215 (0.5); 2.5126 (6.3); 2.5082 (12.9); 2.5037 (17.1); 2.4991 (12.2); 2.4946 (5.8); 1.2767 (16.0); 1.2601 (15.5)。
步驟 2 : 3- 氯 -5-( 異丙硫基 ) 苯甲酸
將2.1 mL的氫氧化鈉之50%水溶液加至585 mg (2.76 mmol) 3-氯-5-(異丙硫基)苯甲腈在20 mL乙醇中之溶液。將混合物於回流下加熱45 min。然後在減壓下移除揮發物。加水,藉由添加1 M 鹽酸將pH調整至pH 1並用乙酸乙酯重複萃取混合物。將合併的有機層用鹽水洗滌並接著用Na
2SO
4乾燥。在減壓下移除溶劑以提供610 mg的3-氯-5-(異丙硫基)苯甲酸。
1H-NMR (400 MHz, d
6-DMSO):NMR 峰列表:δ= 7.7701 (1.6); 7.7662 (3.0); 7.7624 (2.1); 7.7195 (1.7); 7.7146 (2.5); 7.7110 (2.0); 7.6738 (1.9); 7.6691 (3.0); 7.6645 (1.5); 3.7020 (0.4); 3.6854 (1.1); 3.6688 (1.5); 3.6522 (1.1); 3.6356 (0.4); 2.5160 (3.1); 2.5115 (6.7); 2.5069 (9.1); 2.5023 (6.5); 2.4977 (3.1); 1.2786 (16.0); 1.2620 (15.4); -0.0002 (4.8)。
ESI 質量 [m/z]:231.1 [M+H]
+ 步驟 3 : 3- 氯 -5-( 異丙硫基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }- 苯甲醯胺 ( 實施例 I-046)
將15 mL乙腈、922 mg (2.43 mmol) N,N,N′,N′-四甲基-O-(1H-苯并三唑-1-基)脲鎓六氟磷酸鹽(HBTU)和0.47 mL (3.6 mmol)
N,N-二異丙基乙胺加至321 mg (1.39 mmol)的3-氯-5-(異丙硫基)苯甲酸。將混合物在室下攪拌1 h。接著添加315 mg (1.39 mmol)的(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽。在藉由逆相層析法(H
2O / 乙腈)將反應混合物純化以提供302 mg的3-氯-5-(異丙硫基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺之前,將其在室溫下攪拌過夜。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:403.2 [M+H]
+ 步驟 4 : 3- 氯 -5-( 異丙磺醯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }- 苯甲醯胺 ( 實施例 I-051)
將193 mg (70%純度,0.78 mmol) 3-氯過氧苯甲酸加至150 mg (0.37 mmol) 3-氯-5-(異丙硫基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺在2 mL CH
2Cl
2中在0℃下之溶液。將反應混合物在0℃下攪拌2 h,之後添加飽和NaHCO
3水溶液。分離該等層並將水層用CH
2Cl
2重複萃取。將合併的有機層用鹽水洗滌並接著用Na
2SO
4乾燥。在減壓下移除溶劑並藉由層析法在矽石上(環己烷 / 乙酸乙酯)將餘殘物純化以提供121 mg的3-氯-5-(異丙磺醯基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表。
ESI 質量 [m/z]:435.2 [M+H]
+ 3- 氯 -5- 環丙基 苯甲酸
藉由用氬氣吹掃將1.00 g (3.37 mmol) 3-氯-5-碘苯甲酸甲酯、375 mg (4.36 mmol) 環丙基硼酸、2.5 g (11.7 mmol) K
3PO
4、在20 mL甲苯和1 mL H
2O中的95 mg (0.33 mmol) 三環己膦之混合物除氣。添加38 mg (0.16 mmol) 乙酸鈀(II)。將混合物在100℃下加熱3 h和在室溫下過夜。再添加290 mg (3.37 mmol) 環丙基硼酸和38 mg (0.16 mmol)乙酸鈀(II)和將混合物於回流下加熱過夜。加水和乙酸乙酯,該等層分離並用乙酸乙酯萃取水層數次。將合併的有機層用Na
2SO
4乾燥,過濾並在減壓下濃縮。藉由層析法在矽石上(環己烷 / 乙酸乙酯)和逆相層析法(H
2O / 乙腈)將殘餘物純化以提供381 mg的3-氯-5-環丙基苯甲酸甲酯。
將378 mg (1.79 mmol) 3-氯-5-環丙基苯甲酸甲酯在6 mL甲醇中之溶液用5 mL的氫氧化鈉之1M水溶液處理。將混合物在室溫下攪拌過夜。然後在減壓下移除揮發物。加水,藉由添加1M鹽酸將pH調整至pH 1並用乙酸乙酯重複萃取混合物。將合併的有機層用Na
2SO
4乾燥並在減壓下移除溶劑以提供338 mg的3-氯-5-環丙基苯甲酸。
1H-NMR (400 MHz, d
6-DMSO):NMR峰列表:δ= 13.2677 (3.0); 7.6530 (8.9); 7.6483 (13.0); 7.6443 (10.4); 7.5890 (9.2); 7.5853 (16.0); 7.5815 (8.8); 7.3987 (9.2); 7.3941 (15.6); 7.3894 (8.5); 3.3324 (4.4); 2.6744 (0.4); 2.5279 (0.9); 2.5232 (1.4); 2.5145 (21.3); 2.5100 (43.8); 2.5055 (58.0); 2.5009 (41.7); 2.4964 (19.9); 2.3323 (0.4); 2.0807 (1.5); 2.0681 (3.2); 2.0597 (3.4); 2.0557 (2.2); 2.0472 (6.6); 2.0387 (2.2); 2.0346 (3.6); 2.0262 (3.5); 2.0136 (1.7); 1.0376 (4.0); 1.0263 (10.8); 1.0209 (10.9); 1.0170 (5.5); 1.0102 (5.6); 1.0053 (11.2); 0.9998 (10.4); 0.9893 (4.7); 0.9726 (0.4); 0.9519 (0.4); 0.8186 (0.4); 0.8055 (0.4); 0.7809 (5.0); 0.7699 (12.3); 0.7648 (12.0); 0.7575 (11.0); 0.7525 (13.4); 0.7409 (4.0); -0.0002 (11.0); -0.0084 (0.3)。
ESI 質量 [m/z]:197.2 [M+H]
+ 1-(4- 氟苯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3-( 三氟甲基 )-1H- 吡唑 -5- 甲醯胺的合成 ( 實施例 I-052) 步驟 1 : 1-(4- 氟苯基 )-3-(2- 呋喃基 )-5-( 三氟甲基 )-1H- 吡唑和 1-(4- 氟苯基 )-5-(2- 呋喃基 )-3-( 三氟甲基 )-1H- 吡唑
將2.1 mL (12 mmol)
N,N-二異丙基乙胺和1.18 g (7.3 mmol) (4-氟苯基)肼鹽酸鹽加至1.00 g (4.85 mmol) 4,4,4-三氟-1-(2-呋喃基)丁烷-1,3-二酮在15 mL乙醇中之溶液。在減壓下移除所有揮發物之前將混合物在室溫下攪拌過夜。將水和乙酸乙酯加至殘餘物。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用鹽水洗滌並用Na
2SO
4乾燥。在減壓下移除溶劑。將殘餘物溶解在15 mL四氫呋喃中。添加7 mL 3M鹽酸並將混合物在100℃下加熱3 h。然後在減壓下移除溶劑。將水和乙酸乙酯加至殘餘物。分離該等層並用乙酸乙酯重複萃取水層。將合併的有機層用鹽水洗滌並用Na
2SO
4乾燥。在減壓下移除溶劑並將殘餘物吸附在逆相矽膠上。藉由逆相層析法(H
2O / 乙腈)之純化提供812 mg的1-(4-氟苯基)-3-(2-呋喃基)-5-(三氟甲基)-1H-吡唑和1-(4-氟苯基)-5-(2-呋喃基)-3-(三氟甲基)-1H-吡唑之不可分離的混合物。
1H NMR (DMSO-d
6, 400 MHz):NMR峰列表:δ= 7.8066 (3.4); 7.8049 (3.4); 7.8024 (3.4); 7.7757 (10.1); 7.7715 (10.0); 7.6722 (2.0); 7.6600 (2.3); 7.6500 (2.7); 7.6380 (2.5); 7.6176 (0.9); 7.6092 (6.9); 7.6044 (3.2); 7.5970 (7.6); 7.5921 (5.3); 7.5870 (9.1); 7.5797 (3.9); 7.5749 (8.5); 7.5665 (1.0); 7.4735 (5.9); 7.4670 (3.4); 7.4452 (6.1); 7.4371 (9.2); 7.4314 (3.4); 7.4230 (4.4); 7.4154 (14.7); 7.3985 (2.8); 7.3935 (6.7); 7.3853 (0.8); 7.2688 (16.0); 6.9756 (3.1); 6.9672 (3.3); 6.6456 (2.3); 6.6410 (2.4); 6.6374 (2.3); 6.6331 (2.0); 6.5590 (6.2); 6.5545 (6.6); 6.5505 (6.8); 6.5462 (6.2); 6.2806 (9.5); 6.2719 (8.9); 3.3267 (119.8); 2.6714 (1.0); 2.5065 (133.8); 2.5025 (166.0); 2.4984 (121.6); 2.3291 (1.0); -0.0004 (25.2)。
ESI 質量 [m/z]:297.1 [M+H]
+ 步驟 2 : 1-(4- 氟苯基 )-3-( 三氟甲基 )-1H- 吡唑 -5- 甲酸和 1-(4- 氟苯基 )-5-( 三氟甲基 )-1H- 吡唑 -3- 甲酸
將777 mg (2.62 mmol)的前述步驟中所得之1-(4-氟苯基)-3-(2-呋喃基)-5-(三氟甲基)-1H-吡唑和1-(4-氟苯基)-5-(2-呋喃基)-3-(三氟甲基)-1H-吡唑之混合物溶解在8 mL乙腈、8 mL CH
2Cl
2和12 mL水的混合物中。將54 mg (0.26 mmol) 氯化釕(III)添加至此混合物,接著是2.81 g (13.1 mmol)過碘酸鈉。將反應混合物在室溫下攪拌5 h。添加20 mL的1M鹽酸並將混合物用矽藻土過濾,用乙酸乙酯和水洗滌。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用鹽水洗滌並用Na
2SO
4乾燥。在減壓下移除溶劑並將殘餘物吸附在逆相矽膠上。藉由逆相層析法(H
2O / 乙腈)之純化提供101 mg純度73 %之1-(4-氟苯基)-5-(三氟甲基)-1H-吡唑-3-甲酸,155 mg純度89 %之1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-甲酸和另一部分的139 mg純度98 %之1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-甲酸。
1-(4-氟苯基)-5-(三氟甲基)-1H-吡唑-3-甲酸:
1H NMR (DMSO-d
6, 400 MHz):NMR峰列表 δ= 13.4416 (1.2); 8.3160 (0.6); 7.7337 (0.4); 7.6983 (0.7); 7.6895 (6.2); 7.6775 (6.6); 7.6724 (4.4); 7.6672 (7.8); 7.6552 (7.4); 7.6462 (0.9); 7.6362 (2.4); 7.6307 (0.9); 7.6240 (2.5); 7.6190 (1.4); 7.6137 (2.9); 7.6071 (1.0); 7.6015 (2.7); 7.5366 (16.0); 7.5245 (0.5); 7.5120 (0.4); 7.4912 (4.6); 7.4827 (10.2); 7.4770 (3.0); 7.4701 (1.6); 7.4655 (3.6); 7.4610 (15.6); 7.4559 (3.4); 7.4515 (1.2); 7.4445 (2.6); 7.4389 (7.9); 7.4302 (0.6); 7.3893 (0.3); 7.3806 (2.9); 7.3751 (1.0); 7.3678 (0.5); 7.3588 (4.7); 7.3538 (1.1); 7.3422 (0.8); 7.3367 (2.3); 5.7562 (2.2); 3.3275 (47.8); 2.6807 (0.5); 2.6762 (1.0); 2.6717 (1.5); 2.6672 (1.1); 2.6625 (0.5); 2.5252 (4.4); 2.5204 (6.8); 2.5117 (86.0); 2.5073 (173.8); 2.5028 (227.5); 2.4982 (163.1); 2.4937 (78.4); 2.3386 (0.5); 2.3342 (1.0); 2.3296 (1.4); 2.3251 (1.0); 2.3204 (0.5); 0.0080 (0.8); -0.0002 (26.3); -0.0085 (0.9)。
ESI 質量 [m/z]:275.1 [M+H]
+1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-甲酸:
1H NMR (DMSO-d
6, 400 MHz):NMR峰列表 δ= 8.3156 (0.4); 7.6460 (0.8); 7.6373 (8.1); 7.6318 (2.9); 7.6251 (8.6); 7.6200 (4.9); 7.6147 (9.7); 7.6081 (3.4); 7.6026 (9.2); 7.5939 (1.0); 7.5005 (16.0); 7.3903 (1.1); 7.3816 (9.5); 7.3760 (2.9); 7.3687 (1.6); 7.3645 (3.3); 7.3597 (15.9); 7.3547 (3.3); 7.3432 (2.6); 7.3377 (7.8); 7.3289 (0.7); 5.7558 (8.6); 3.3341 (12.6); 2.6760 (0.7); 2.6714 (1.0); 2.6669 (0.7); 2.5249 (2.8); 2.5201 (4.4); 2.5114 (60.4); 2.5070 (122.2); 2.5025 (160.1); 2.4979 (115.0); 2.4935 (55.6); 2.3338 (0.7); 2.3293 (1.0); 2.3248 (0.7); 2.3202 (0.4); 0.0080 (0.5); -0.0002 (17.5); -0.0085 (0.6)。
ESI 質量 [m/z]:275.1 [M+H]
+ 步驟 3 : 1-(4- 氟苯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3-( 三氟甲基 )-1H- 吡唑 -5- 甲醯胺 ( 實施例 I-052)
將130 mg (0.47 mmol) 1-(4-氟苯基)-3-(三氟甲基)-1H-吡唑-5-甲酸、328 mg (0.86 mmol) 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-吡啶鎓氧化物六氟磷酸鹽(HATU)、0.17 mL (1.3 mmol)
N-乙基二異丙胺和2 mL乙腈之混合物在室溫下攪拌45 min。添加98 mg (0.43 mmol) (1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽並將混合物在室溫下攪拌過夜。然後將混合物用乙腈稀釋並吸附在逆相矽膠上。藉由逆相層析法(H
2O / 乙腈)之純化提供146 mg 1-(4-氟苯基)-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-(三氟甲基)-1H-吡唑-5-甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表
ESI 質量 [m/z]:447.2 [M+H]
+ 3- 氯 -5-(N- 甲氧基乙亞胺醯基 (ethanimidoyl))-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺的合成 ( 實施例 I-057) 步驟 1 : 3- 乙醯基 -N-[(2S)-1- 胺基 -1- 側氧丙 -2- 基 ]-5- 氯苯甲醯胺
將2.494 g (20 mmol) L-丙胺醯胺鹽酸鹽、0.994 g (5 mmol)的3-乙醯基-5-氯苯甲酸(市售)和2.62 mL(15 mmol) DIPEA溶解在18.6 mL DMF中。滴加4.4 mL (7.5 mmol)的T3P
®溶液(50 wt. %的EtOAc溶液)並將混合物在室溫下攪拌過夜。在減壓下移除溶劑,將剩餘的殘餘物溶解在15 mL水和3 mL飽和NaHCO
3水溶液並用15 mL EtOAc萃取。將水層用EtOAc再萃取三次,將合併的有機層用鹽水洗滌,用Na
2SO
4乾燥,過濾,及在減壓下蒸發以獲得360 mg (產率:26.7 %)的灰白色固體,將其原樣使用在下一步驟中。
1H-NMR (400 MHz, d
6-DMSO): 8.86 – 8.85 (d, 1H, NH), 8.38 (s, 1H), 8.21 (s, 1H), 8.10 (s, 1H), 7.45 (broad s, 1H, NH
2), 7.02 (broad s, 1H, NH
2), 4.45 – 4.40 (quint., 1H), 2.66 (s, 3H), 1.36 – 1.34 (d, 3H)。
ESI 質量 [m/z]:269.2 [M+H]
+ 步驟 2 : N-[(2S)-1- 胺基 -1- 側氧丙 -2- 基 ]-3- 氯 -5-(N- 甲氧基乙亞胺醯基 ) 苯甲醯胺
將360 mg (1.34 mmol)的3-乙醯基-N-[(2S)-1-胺基-1-側氧丙-2-基]-5-氯苯甲醯胺、134 mg (1.60 mmol)甲氧胺鹽酸鹽和0.224 mL (1.6 mmol) Et
3N溶解在15 mL乙腈中並回流48 h。在減壓下移除溶劑,將剩餘的殘餘物溶解於二氯甲烷中並用水洗滌。將水相用二氯甲烷萃取三次,將合併的有機層經Na
2SO
4乾燥,過濾,及在減壓下蒸發以獲得304 mg (產率:70.8 %)的灰白色固體,將其原樣使用在下一步驟中。
1H-NMR (400 MHz, d
6-DMSO): 8.73 – 8.71 (d, 1H, NH), 8.08 (s, 1H), 7.99 (s, 1H), 7.84 (s, 1H), 7.42 (broad s, 1H, NH
2), 7.00 (broad s, 1H, NH
2), 4.44 – 4.39 (quint., 1H), 3.32 (s, 3H), 2.21 (s, 3H), 1.34 – 1.32 (d, 3H)。
ESI 質量 [m/z]:298.1 [M+H]
+ 步驟 3 : 3- 氯 -5-(N- 甲氧基乙亞胺醯基 )-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 ( 實施例 I-057)
將304 mg (1.02 mmol)的N-[(2S)-1-胺基-1-側氧丙-2-基]-3-氯-5-(N-甲氧基乙亞胺醯基)苯甲醯胺和182 mg (1.53 mmol) N,N-二甲基甲醯胺二甲基縮醛溶解在20 mL二氯甲烷中並回流2 h。在減壓下移除溶劑,將剩餘的殘餘物用10 mL二㗁烷和1 mLHOAc之混合物溶解。添加137 mg (1.24 mmol)的2-肼基嘧啶並將反應混合物在50℃下攪拌過夜。在減壓下蒸發溶劑後,將殘餘物溶於二氯甲烷中,用飽和NaHCO
3水溶液洗滌,並將分離的有機相再次在真空中減少。藉由逆相層析法(H
2O / 乙腈)之純化提供148 mg (產率:35.2 %)的呈灰白色固體之目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:400.2 [M+H]
+ 3- 氯 -N-{(1R)-1-[1-(5- 氰吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ]-2- 甲氧基乙基 }-5-( 甲磺醯基 ) 苯甲醯胺的合成 ( 實施例 I-058) 步驟 1 : N-[3- 氯 -5-( 甲磺醯基 ) 苯甲醯基 ]-O- 甲基 -L- 絲胺酸
將1 g (8.39 mmol)的O-甲基-L-絲胺酸和3.22 mL (18.4 mmol) DIPEA溶解在50 mL二氯甲烷中。對此反應混合物,滴加溶解在20 mL二氯甲烷中之2.23 g (8.81 mmol)的3-氯-5-(甲磺醯基)苯甲醯氯。將反應混合物在室溫下攪拌過夜,隨後以水進行後處理。將水相用二氯甲烷萃取三次,將合併的有機層經Na
2SO
4乾燥,過濾和在減壓下蒸發。經由pHPLC純化後獲得622 mg的標題化合物且原樣使用在下一步驟中。
ESI 質量 [m/z]:334.0 [M+H]
+ 步驟 2 : N-[(2S)-1- 胺基 -3- 甲氧基 -1- 側氧丙 -2- 基 ]-3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺
將622 mg (1.85 mmol)的N-[3-氯-5-(甲磺醯基)苯甲醯基]-O-甲基-L-絲胺酸溶解在18.6 mL THF中。0.24 mL (1.85 mmol)氯甲酸異丁酯且隨後在-15℃下滴加0.204 mL (1.85 mmol) N-甲基嗎福林並將混合物在-15℃下攪拌15 min。在-15℃下滴加0.42 mL (2.68 mmol)氨(25% wt%之水溶液)。將溫度保持45分鐘,接著在室溫下用鹽水淬滅。將反應混合物用乙醚萃取三次,將合併的有機層經Na
2SO
4乾燥,過濾和在減壓下蒸發。獲得473 mg的目標化合物且原樣使用在下一步驟中。
ESI 質量 [m/z]:335.1 [M+H]
+ 步驟 3 : 3- 氯 -N-{(1R)-1-[1-(5- 氰吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ]-2- 甲氧基乙基 }-5-( 甲磺醯基 ) 苯甲醯胺 ( 實施例 I-058)
將248 mg (0.74 mmol)的N-[(2S)-1-胺基-3-甲氧基-1-側氧丙-2-基]-3-氯-5-(甲磺醯基)苯甲醯胺和132 mg (1.11 mmol) N,N-二甲基甲醯胺二甲基縮醛溶解在20 mL二氯甲烷中並回流2 h。在減壓下移除溶劑,將剩餘的殘餘物用10 mL二㗁烷和1 mL HOAc之混合物溶解。添加121 mg (0.90 mmol)的6-肼基菸鹼甲腈並將反應混合物在50℃下攪拌過夜。在減壓下蒸發溶劑後,將殘餘物溶解在二氯甲烷中,用飽和NaHCO
3水溶液洗滌,並將分離的有機相再次在真空中減少。藉由逆相層析法(H
2O / 乙腈)之純化提供77 mg (產率:19.6 %)的目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:461.2 [M+H]
+ 3- 氯 -5-[( 苯磺醯基 ) 胺基 ]-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 的合成 ( 實施 例 I-086) 步驟 1 : 3- 氯 -5-[( 苯磺醯基 ) 胺基 ] 苯甲酸甲酯
將1.0 g (5.65 mmol)苯磺醯氯和0.45 g (5.66 mmol) 吡啶加至0.52 g (2.83 mmol) 3-胺基-5-氯苯甲酸甲酯在氯仿(5 mL)中於0℃下之溶液並接著在室溫下攪拌反應混合物。轉化完成後,將混合物倒入冰水和飽和NH
4Cl水溶液之混合物中並用乙酸乙酯萃取。將合併的有機相用鹽水洗滌,乾燥並在減壓下移除溶劑。將剩餘的殘餘物以環己烷/乙酸乙酯梯度在矽膠上進行層析以提供0.66 g (純度:99.5%;產率:71.6 %)的目標化合物。
ESI 質量 [m/z]:326.0 [M+H]
+Rt = 1.24 min (儀器:LC-MS6)
步驟 2 : 3- 氯 -5-[( 苯磺醯基 ) 胺基 ] 苯甲酸
將0.66 g (2.03 mmol) 3-氯-5-[(苯磺醯基)胺基]苯甲酸甲酯在2 mL乙醇/THF (1:1)之混合物中的溶液用8.48 g (8.14 mmol)的氫氧化鈉之1M水溶液處理。將反應混合物在室溫下攪拌2 hrs。將混合物倒入冰水、乙酸乙酯和HCl 10%水溶液之混合物。分離該等層並將水層用乙酸乙酯重複萃取、用水和鹽水洗滌且最後乾燥。在減壓下移除溶劑以提供0.62 g (純度:97.0%;產率:94.0 %)的目標化合物。
ESI 質量 [m/z]:312.0 [M+H]
+Rt = 1.00 min (儀器:LC-MS7)
步驟 3 : 3- 氯 -5-[( 苯磺醯基 ) 胺基 ]-N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 ( 實施例 I-086)
將0.21 g ( 0.66 mmol) 3-氯-5-[(苯磺醯基)胺基]苯甲酸在5 二氯甲烷中之溶液用0.30 g (0.79 mmol) 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)和0.16 mL (0.92 mmol)
N,N-二異丙基乙胺處理並接著將混合物在室溫下攪拌30分鐘。其後將先前攪拌30分鐘的0.15 g (0.66 mmol) (1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽(1:1)和0.23 mL (1.32 mmol)
N,N-二異丙基乙胺在2.5 mL二氯甲烷中之溶液加至反應並將混合物在室溫下攪拌過夜。將混合物用飽和NaH
2PO
4水溶液處理並用二氯甲烷萃取。將合併的有機層乾燥且最後在壓力下減少揮發物。藉由逆相層析法(H
2O/乙腈)將殘餘物純化以提供36 mg (純度:95.5%;產率:11.0 %)的目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:484.1 [M+H]
+Rt = 0.97 min (儀器:LC-MS6)
3- 氯 -N-{(1S)-1-[1-(2- 嘧啶基 )-3-( 三氟甲基 )-1
H-1,2,4-
三唑 -5- 基 ] 乙基 }-5-( 甲磺醯基 ) 苯甲醯胺 的合成 ( 實施例 I-091) 步驟 1 : 2-[2- 嘧啶基 ] 醯肼 -2,2,2- 三氟 - 乙醯亞胺酸 (ethanimidic acid
)
將3.87 g (21 mmol) 2,2,2-三氟-乙醯亞胺酸乙酯(純度:76.5%)加至在甲醇(15 mL)中之1.65 g (15 mmol) 2-肼基-嘧啶,並將反應混合物在室溫下攪拌過夜。蒸發溶劑並接著將殘餘物與正己烷(30 mL)和乙酸乙酯(3 mL)一起攪拌。將褐色沉澱物分離並乾燥以獲得2.6 g (純度:94.6 %;產率:7.8 %) 2-[2-嘧啶基]醯肼-2,2,2-三氟-乙醯亞胺酸。
ESI 質量 [m/z]:206.0 [M+H]
+R
t= 0.233 min (儀器:LC-MS 7)
步驟 2 : 2-[(1S)-1-[3-( 三氟甲基 )-1-(2- 嘧啶基 )-1
H-1,2,4-
三唑 -5- 基 ) 乙基 ]-1
H-
異吲哚 -1,3(2H)- 二酮
將2.80g (11.78 mmol) (α
S)-1,3-二氫-α-甲基-1,3-二側氧基-2
H-異吲哚-2-乙醯氯(參見從(α
S)-1,3-二氫-α-甲基-1,3-二側氧基-2
H-異吲哚-2-乙酸(購自ABCR之Pht-Ala-OH)和草醯氯製備:
Tetrahedron : Asymmetry, 21(8), 936-942, 2010)加至在吡啶(40 mL)中之2.55 g (11.78 mmol) 2-[2-嘧啶基]醯肼-2,2,2-三氟-乙醯亞胺酸,並將反應混合物在室溫下攪拌過夜。接著加水(200 mL)並將混合物用二氯甲烷(200 mL)萃取。將有機相分離,乾燥並將溶劑蒸發。將剩餘的固體殘餘物以環己烷/丙酮梯度在矽膠上進行層析以提供1.65 g (純度:93.4%;產率:33.6 %)的呈無色固體之目標化合物。
ESI 質量 [m/z]:389.1 [M+H]
+R
t= 1.20 min (儀器:LC-MS 7)
步驟 3 : (α
S)-
甲基 -1-(2- 嘧啶基 )-1
H-1,2,4-
三唑 -5- 甲 烷 胺
將937.6 mg (10.30 mmol)肼水合物加至在乙醇(40 mL)中之1.6 g (4.12 mmol) 2-[(1
S)-1-[3-(三氟甲基)-1-(1-(2-嘧啶基)-1
H-1,2,4-三唑-5-基)乙基]-1
H-異吲哚-1,3(2
H)-二酮,並於回流下加熱反應混合物。30分鐘後,形成無色沉澱物。將反應混合物於回流下再攪拌並加熱1小時,添加丙酮(20 mL)並繼續再加熱30分鐘。將反應混合物濃縮並用乙醇處理固體殘餘物。然後,將溶劑蒸發以提供660 mg (純度:70 %;產率:43.4%) (α
S)-甲基-1-(2-嘧啶基)-1
H-1,2,4-三唑-5-甲烷胺,未經純化地將其用於
N-苯甲醯化反應(步驟4)。
ESI 質量 [m/z]:259.0 [M+H]
+R
t= 0.14 min (寬) (儀器:LC-MS 7)
步驟 4 : 3- 氯 -N-{(1S)-1-[1-(2- 嘧啶基 )-3-( 三氟甲基 )-1
H-1,2,4-
三唑 -5- 基 ] 乙基 }-5-( 甲磺醯基 ) 苯甲醯胺
將273.7 mg (0.72 mmol) [
O-(7-氮雜苯并三唑-1-基)-
N,N,N′,N′-四甲基脲鎓-六氟磷酸鹽] (HATU)加至在
N,N-二甲基甲醯胺(DMF)(5 mL)中之221.3 mg (0.60 mmol) (αS)-甲基-1-(2-嘧啶基)-1
H-1,2,4-三唑-5-甲烷胺、145.1 mg (0.60 mmol) 3-氯-5-(甲磺醯基)-苯甲酸、100.8 mg (0.78 mmol)
N,N-二異丙基乙胺(Hünig氏鹼),並將反應混合物在室溫下攪拌過夜。濃縮反應混合物並將固體殘餘物用二氯甲烷處理並接著用飽和NaHCO
3溶液和水萃取。將有機相分離,乾燥並將溶劑蒸發。將剩餘的固體殘餘物以環己烷/丙酮梯度在矽膠上進行層析以提供100 mg (純度:98.4%;產率:34.5 %)的目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:475.0 [M+H]
+R
t= 1.09 min (儀器:LC-MS 7)
3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[(2,2,2- 三氟乙基 ) 亞磺醯基 ] 苯甲醯胺 ( 實施例 I-092) 的合成 , 及 3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[(2,2,2- 三氟乙基 ) 磺醯基 ] 苯甲醯胺的合成 ( 實施例 I-093) 步驟 1 : 3- 氯 -5-[(2,2,2- 三氟乙基 ) 氫硫基 ] 苯甲腈
將0.74 mL (8.35 mmol) 2,2,2-三氟乙硫醇小心地加至310 mg (7.1 mmol) 氫化鈉 (55%礦物油懸浮液)在15 mL無水
N,N-二甲基甲醯胺中之懸浮液。在室溫下攪拌30分鐘後,添加1.00 g (6.42 mmol) 3-氯-5-氟苯甲腈。將混合物在室溫下攪拌5 hrs並接著藉由添加1 mL H
2O和1.1 mL冰醋酸淬滅。在減壓下移除揮發物。將水和乙酸乙酯加至殘餘物。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用鹽水洗滌並接著用Na
2SO
4乾燥。在減壓下移除溶劑並藉由逆相層析法(H
2O/乙腈)將殘餘物純化以提供1.40 g的3-氯-5-[(2,2,2-三氟乙基)氫硫基]苯甲腈。
1H-NMR (400 MHz, d
6-DMSO): 8.03 – 8.02 (m, 1H), 7.98 – 7.97 (m, 1H), 7.93 – 7.92 (m, 1H), 4.30 – 4.22 (q, 2H)。
ESI 質量 [m/z]:252.1 [M+H]
+ 步驟 2 : 3- 氯 -5-[(2,2,2- 三氟乙基 ) 氫 硫基 ] 苯甲酸
將800 mg (3.17 mmol) 3-氯-5-[(2,2,2-三氟乙基)氫硫基]苯甲腈、3.5 mL水和3.6 mL濃硫酸之混合物在100℃下加熱2天。添加水和乙酸乙酯。分離該等層並將水層用乙酸乙酯重複萃取。將合併的有機層用鹽水洗滌並接著用Na
2SO
4乾燥。在減壓下移除溶劑並藉由逆相層析法(H
2O/乙腈)將殘餘物純化以提供728 mg的3-氯-5-[(2,2,2-三氟乙基)氫硫基]苯甲酸。
1H-NMR (400 MHz, d
6-DMSO): 13.55 (s, 1H, COOH), 7.91 – 7.89 (m, 2H), 7.77 – 7.76 (m, 1H), 4.23 – 4.16 (q, 2H)。
ESI 質量 [m/z]:269.0 [M-H]
- 步驟 3 : 3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[(2,2,2- 三氟乙基 ) 氫硫基 ] 苯甲醯胺
將430 mg (1.58 mmol) 3-氯-5-[(2,2,2-三氟乙基)氫硫基]苯甲酸、1.05 g (2.77 mmol) 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)、0.53 mL(4.1 mmol)
N-乙基二異丙胺和5 mL乙腈之混合物在室溫下攪拌60分鐘。添加400 mg (90%純度,1.58 mmol) (1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙胺鹽酸鹽並將混合物在室溫下攪拌過夜。然後將混合物用乙腈稀釋並吸附在逆相矽膠上。藉由逆相層析法(H
2O/乙腈)之純化提供440 mg 3-氯-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-5-[(2,2,2-三氟乙基)氫硫基]苯甲醯胺。
1H-NMR(400.2 MHz, d
6-DMSO):NMR峰列表:9.1997 (1.6); 9.1816 (1.6); 8.9905 (10.8); 8.9783 (11.1); 8.1596 (8.2); 7.7896 (1.9); 7.7852 (4.2); 7.7807 (2.7); 7.7631 (2.8); 7.7593 (4.4); 7.7553 (2.2); 7.6735 (2.8); 7.6692 (3.9); 7.6652 (2.4); 7.6358 (3.0); 7.6236 (5.6); 7.6114 (2.8); 5.9856 (1.2); 5.9680 (2.0); 5.9503 (1.2); 5.7569 (0.9); 4.2048 (1.1); 4.1791 (3.4); 4.1534 (3.6); 4.1276 (1.2); 3.3240 (13.7); 2.6717 (0.4); 2.5254 (1.0); 2.5206 (1.5); 2.5120 (23.4); 2.5074 (48.5); 2.5029 (63.6); 2.4982 (44.4); 2.4936 (20.3); 2.3297 (0.4); 1.6339 (7.8); 1.6165 (7.7); 1.3975 (16.0); -0.0002 (8.5)。
ESI 質量 [m/z]:443.1 [M+H]
+ 步驟 4 : 3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[(2,2,2- 三氟乙基 ) 亞磺醯基 ] 苯甲醯胺 ( 實施例 I-092) 和 3- 氯 -N-{(1S)-1-[1-( 嘧啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-5-[(2,2,2- 三氟乙基 ) 磺醯基 ] 苯甲醯胺 ( 實施例 I-093)
將74 mg (70%純度,0.31 mmol) 3-氯過氧苯甲酸加至140 mg (0.31 mmol) 3-氯-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-5-[(2,2,2-三氟乙基)氫硫基]苯甲醯胺在2 mL CH
2Cl
2中於0°C之溶液。將反應混合物在0℃下攪拌2.5 hrs,其後添加飽和NaHCO
3水溶液。分離該等層並將水層用CH
2Cl
2重複萃取。在減壓下移除溶劑並藉由逆相層析法(H
2O/乙腈)將殘餘物純化以提供98 mg的3-氯-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-5-[(2,2,2-三氟乙基)亞磺醯基]苯甲醯胺(實施例I-092)和38 mg的3-氯-N-{(1S)-1-[1-(嘧啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-5-[(2,2,2-三氟乙基)磺醯基]苯甲醯胺(實施例I-093)。
實施例I-092
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:459.1 [M+H]
+
實施例I-093
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:475.1 [M+H]
+ 3- 氯 -5-(1- 氰環丙基 )-N-{(1S)-1-[1-(5- 氰吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 的合成 ( 實施例 I-119) 步驟 1 : 3- 氯 -5-(1- 氰環丙基 ) 苯甲酸甲酯
在25°C下將NaOH (4.58 g,114.49 mmol)和苯甲基(三甲基)氯化銨(10.32 g,68.69 mmol)一次全部加至3-氯-5-(氰甲基)苯甲酸甲酯(12 g,57.24 mmol)在1,2-二溴乙烷(150 mL)中之溶液。將混合物在65℃下攪拌12 hrs和之後用NH
4Cl (50 mL)之飽和水溶液稀釋並用EtOAc (50 mL)萃取。將水相用EtOAc (30 mL)萃取兩次。將合併的有機層經Na
2SO
4乾燥和過濾。在減壓下移除溶劑。藉由管柱層析法(矽膠,石油醚/EtOAc = 100/1至20/1)將殘餘物純化以產生呈黃色油之3-氯-5-(1-氰環丙基)苯甲酸甲酯(8.8 g,65%產率)。
步驟 2 : 3- 氯 -5-(1- 氰環丙基 ) 苯甲酸
在25°C下將TMSOK (6.71 g,52.28 mmol)一次全部加至3-氯-5-(1-氰環丙基)苯甲酸甲酯(8.8 g,37.34 mmol)在THF (100 mL)中之溶液。將混合物在25°C下攪拌12 hrs。用1M鹽酸將反應懸浮液調整至pH = 5至6。懸浮液的顏色變為橙色。用H
2O (15 mL)稀釋混合物。用EtOAc (50 mL)將水萃取三次。將合併的有機層經Na
2SO
4乾燥,過濾並在減壓下濃縮以產生呈淺黃色固體之3-氯-5-(1-氰環丙基)苯甲酸(5.05 g,61%產率)。
1H-NMR (400 MHz, MeOD): δ, 7.85 – 7.93 (m, 2H), 7.55 (t,
J=1.9 Hz, 1 H), 1.78 - 1.82 (m, 2 H), 1.55 - 1.59 (m, 2 H)。使用Varian 400MR NMR機器測量。
步驟 3 : 3- 氯 -5-(1- 氰環丙基 )-N-{(1S)-1-[1-(5- 氰吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 } 苯甲醯胺 ( 實施例 I-119)
將116.7mg (0.52 mmol) 3-氯-5-(1-氰環丙基)苯甲酸、363.1 mg (0.95 mmol) 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)、0.22 mL (1.67 mmol)
N-乙基二異丙胺和2 mL DMF之混合物在室溫下攪拌45 min。添加150 mg (0.47 mmol) 6-{5-[(1S)-1-胺乙基]-1H-1,2,4-三唑-1-基}菸鹼甲腈鹽酸鹽並將混合物在室溫下攪拌過夜。然後將混合物稀釋並吸附在逆相矽膠上。藉由逆相層析法(H
2O/乙腈)之純化提供164 mg的呈無色固體之目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中之NMR峰列表
ESI 質量 [m/z]:418.3 [M+H]
+ N-{(1S)-1-[1-(5- 氰吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3- 環丙基 -5- 氟 苯 硫代甲醯胺 (carbothioamide) 的合成 ( 實施例 I-120)
將70 mg (0.18 mmol) N-{(1S)-1-[1-(5-氰吡啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-環丙基-5-氟苯甲醯胺在2.4 mL甲苯中之溶液用70 mg (0.18 mmol) Lawesson氏試劑處理並接著在110℃下攪拌3 hrs。將反應混合物冷卻至室溫並添加飽和NaHCO
3水溶液。分離甲苯層並用乙酸乙酯重複萃取水相。將合併的有機相用飽和NaHCO
3水溶液洗滌並接著乾燥。在減壓下移除溶劑並藉由逆相層析法(H
2O/乙腈)將殘餘物純化以提供47 mg (純度:100%;產率:64.4%)的目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:393.1 [M+H]
+Rt = 1.36 min (儀器:LC-MS6)
6-(5-{(1S)-1-[3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺基 ] 乙基 }-1H-1,2,4- 三唑 -1- 基 )-N- 環丙基菸鹼醯胺 的合成 ( 實施例 I-129) 步驟 1 : 6-(5-{(1S)-1-[3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺基 ] 乙基 }-1H-1,2,4- 三唑 -1- 基 ) 菸鹼酸甲酯 ( 實施 例 I-122)
將1.58 g (5.18 mmol) N-[(2S)-1-胺基-1-側氧丙-2-基]-3-氯-5-(甲磺醯基)苯甲醯胺(中間物a*-002)溶解在50 mL二氯甲烷中。添加1.03 mL (7.77 mmol) N,N-二甲基甲醯胺二甲基縮醛並將混合物在40℃下攪拌2.5 hrs。移除溶劑,將剩餘的殘餘物溶解在50 mL乙酸中,添加1.13 g (6.74 mmol) 6-肼基菸鹼酸甲酯並將混合物在80℃下攪拌3 hrs。在減壓下移除揮發物並藉由矽膠層析法(環己烷 / EtOAc梯度)將剩餘的殘餘物純化以獲得1.88 g (78 %)的呈無色固體之實施例I-122。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:464.2 [M+H]
+Rt = 0.96 min (儀器:LC-MS3)
步驟 2 : 6-(5-{(1S)-1-[3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺基 ] 乙基 }- 1H-1,2,4- 三唑 -1- 基 ) 菸鹼酸 ( 實施例 I-126)
將1.78 g (3.83 mmol) 6-(5-{(1S)-1-[3-氯-5-(甲磺醯基)苯甲醯胺基]乙基}-1H-1,2,4-三唑-1-基)菸鹼酸甲酯懸浮在40 mL甲醇中。添加10.7 mL(10.7 mmol)的1M NaOH並將混合物在室溫下攪拌過夜。在減壓下移除甲醇並將剩餘的殘餘物用1N HCl酸化至pH 1。用EtOAc將混合物溶解,過濾不溶性固體材料並用水和EtOAc洗滌且在通風下乾燥以獲得1.21 g (70%)的呈無色固體之實施例I-126。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:450.2 [M+H]
+Rt = 0.74 min (儀器:LC-MS3)
步驟 3 : 6-(5-{(1S)-1-[3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺基 ] 乙基 }-1H-1,2,4- 三唑 -1- 基 )-N- 環丙基菸鹼醯胺 ( 實施例 I-129)
將110 mg (0.24 mmol) 6-(5-{(1S)-1-[3-氯-5-(甲磺醯基)苯甲醯胺基]乙基}-1H-1,2,4-三唑-1-基)菸鹼酸、185.4 mg (0.48 mmol) 1-[雙(二甲胺基)亞甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸鹽(HATU)、0.11 mL (0.85 mmol)
N-乙基二異丙胺和2 mL DMF之混合物在室溫下攪拌60 min。添加0.015 mL (0.22 mmol)環丙胺並將混合物在室溫下攪拌過夜。然後將混合物用乙腈稀釋並吸附在逆相矽膠上。藉由逆相層析法(H
2O/乙腈)之純化提供48 mg (39%)的呈無色固體之目標化合物。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:489.3 [M+H]
+Rt = 0.81 min (儀器:LC-MS3)
3- 氯 -N-[(1S)-1-(1-{5-[( 環丙羰基 ) 胺基 ] 吡啶 -2- 基 }-1H-1,2,4- 三唑 -5- 基 ) 乙基 ]-5-( 甲磺醯基 ) 苯甲醯胺的合成 ( 實施例 I-139) 步驟 1 : N-{(1S)-1-[1-(5- 胺吡啶 -2- 基 )-1H-1,2,4- 三唑 -5- 基 ] 乙基 }-3- 氯 -5-( 甲磺醯基 ) 苯甲醯胺 ( 實施例 I-135)
將1.49 g (26.6 mmol)鐵粉加至3.0 g (6.7 mmol) 3-氯-5-(甲磺醯基)-N-{(1S)-1-[1-(5-硝吡啶-2-基)-1H-1,2,4-三唑-5-基]乙基}苯甲醯胺在155 mL乙醇和15 mL乙酸的混合物中之溶液。將混合物在80℃下加熱1.5 h。在減壓下移除所有揮發物。將水、乙酸乙酯和NaHCO
3之飽和水溶液加至殘餘物。分離該等層並用乙酸乙酯萃取水層數次。將合併的有機層用鹽水洗滌,用Na
2SO
4乾燥,過濾並在減壓下濃縮以產生2.70 g的N-{(1S)-1-[1-(5-胺吡啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-氯-5-(甲磺醯基)苯甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:421.1 [M+H]
+ 步驟 2 : 3- 氯 -N-[(1S)-1-(1-{5-[( 環丙羰基 ) 胺基 ] 吡啶 -2- 基 }-1H-1,2,4- 三唑 -5- 基 ) 乙基 ]-5-( 甲磺醯基 ) 苯甲醯胺 ( 實施例 I-139)
將150 mg (0.35 mmol) N-{(1S)-1-[1-(5-胺吡啶-2-基)-1H-1,2,4-三唑-5-基]乙基}-3-氯-5-(甲磺醯基)苯甲醯胺在0.6 mL四氫呋喃中之溶液在0℃下用37 mg (0.35 mmol)環丙烷羰基氯和0.06 mL(0.4 mmol)三乙胺處理。將反應混合物在室溫下攪拌過夜。加水,該等層分離並用乙酸乙酯萃取水層數次。將合併的有機層用鹽水洗滌,用Na
2SO
4乾燥,過濾並在減壓下濃縮。藉由逆相層析法(H
2O / 乙腈)將殘餘物純化以提供97 mg的3-氯-N-[(1S)-1-(1-{5-[(環丙羰基)胺基]吡啶-2-基}-1H-1,2,4-三唑-5-基)乙基]-5-(甲磺醯基)苯甲醯胺。
1H-NMR (400 MHz, d
6-DMSO):參見表1中的NMR峰值列表。
ESI 質量 [m/z]:489.1 [M+H]
+ 化合物 之分析數據
在酸性層析條件下藉由LC-MS測定[M+H]
+或[M-H]
-係用每升乙腈1 ml甲酸和每升Millipore水0.9 ml甲酸作為溶析液進行。使用管柱 Zorbax Eclipse Plus C18 50 mm * 2.1 mm。管柱烘箱的溫度為55℃。
儀器:
LC-MS3:具有SQD2質譜儀和SampleManager自動取樣器之Waters UPLC。線性梯度0.0至1.70分鐘從10%乙腈至95 %乙腈,從1.70至2.40分鐘固定95%乙腈,流量0.85 ml/min。
LC-MS6 和 LC-MS7:Agilent 1290 LC、Agilent MSD、HTS PAL 自動取樣器。線性梯度0.0至1.80分鐘從10%乙腈至95%乙腈,從1.80至2.50分鐘固定95%乙腈,流量1.0 ml/min。
在中性層析條件下藉由LC-MS測定[M+H]
+係用含有79 mg/l碳酸銨的乙腈和Millipore水作為溶析液進行。
儀器:
LC-MS4:具有QDA 質譜儀和FTN 自動取樣器之Waters IClass Acquity (管柱 Waters Acquity 1.7 µm 50 mm * 2.1 mm,烘箱溫度45°C)。線性梯度0.0至2.10分鐘從10%乙腈至95%乙腈,從2.10至3.00分鐘固定95%乙腈,流量0.7 ml/min。
LC-MS5:具有MSD 質譜儀和HTS PAL自動取樣器之Agilent 1100 LC系統 (管柱:Zorbax XDB C18 1.8 µm 50 mm * 4.6 mm,烘箱溫度55°C)。線性梯度0.0至4.25分鐘從10%乙腈至95%乙腈,從4.25至5.80分鐘固定95%乙腈,流量2.0 ml/min。
在上述表和製備例中所報告的logP值係根據EEC directive 79/831 Annex V.A8藉由使用逆相層析管柱(C18)之HPLC(高效液相層析法)測定。溫度43℃。校正係利用已知logP值的未分支烷-2-酮類(具有3到16個碳原子)進行。
旋光度係使用Perkin Elmer型號341 旋光計在589 nm波長、10 cm光程及20℃溫度下測定。彼等係報告為比旋光度,包括所測化合物和所使用的溶劑之濃度「c」(g/100 mL)。
1H NMR數據之測定係用配置有1.7 mm TCI超冷探針之Bruker Avance III 400 Mhz,配置有5 mm 多核超冷探針之Bruker Avance III 600 Mhz或配置有5 mm TCI超冷探針之Bruker Avance NEO 600 Mhz,用四甲基矽烷作為參考(0.0)及溶劑CD
3CN、CDCl
3或D
6-DMSO進行。
所選實施例的NMR數據係以習知形式(δ值、多重峰分裂、氫原子數目)或以NMR峰列表列出。
NMR 峰列表 方法
所選實施例之
1H NMR數據係以
1H NMR峰列表之形式說明。對於各訊號峰,首先列出δ值(ppm)及接著在圓括弧中的訊號強度。不同訊號峰的δ值-訊號強度值對以分號彼此分開列示。
一實施例之峰列表因此採取下列形式:
δ
1(強度
1);δ
2(強度
2);……..;δ
i(強度
i);……;δ
n(強度
n)
在NMR光譜(以cm表示)之列印實例中尖銳訊號的強度係與訊號之高度有關且顯示訊號強度的真正比率。在寬訊號的情況下,可顯示數個峰或訊號的半高(middle)及彼等相較於光譜中最強訊號的相對強度。
為了校正
1H NMR光譜的化學位移,吾人使用四甲矽烷及/或溶劑的化學位移,特別是光譜在DMSO中測量的情況下。因此,四甲矽烷峰可但不一定會出現在NMR峰列表中。
1H NMR峰列表係類似於習知
1H NMR列印且因此通常含有在習知NMR判讀中所列示的所有峰。
此外,如同習知的
1H NMR列印,彼等可顯示溶劑訊號、標的化合物之立體異構物(其同樣由本發明提供)及/或雜質峰的訊號。
在溶劑及/或水之δ範圍內的化合物訊號之報告中,吾等的
1H NMR峰之列表顯示標準溶劑峰(例如在d
6-DMSO中之DMSO的峰)及水的峰,其通常平均具有高強度。
標的化合物之立體異構物的峰及/或雜質的峰通常具有平均比標的化合物(例如具有>90%的純度)更低的強度。
該等立體異構物及/或雜質可為特定製備方法之典型。彼等之峰因此可參考「副產物指紋」而幫助識別吾等之製備方法的再現性。
以已知的方法(MestreC、ACD模擬,但也有憑經驗評估之期望值)計算標的化合物之峰的熟習該項技術者若必要時可視需要使用附加的強度濾波器分離出標的化合物之峰。此分離可能類似於在習知
1H NMR判讀之考慮中的峰挑選。
1H NMR峰列表的更多細節可見於在Research Disclosure Database Number 564025。
下表1中所述的根據本發明之化合物同樣為根據本發明之較佳式(I)化合物,其係根據或類似於上述製備例獲得。
(I)
表1
1)‘260 K’表示測量在260K下進行。
2)所述質量對應於來自具有最高強度的[M+H]
+離子之同位素圖的峰。
#表示記錄[M-H]
-離子。
表2 (中間物)
1)‘260 K’表示測量在260K下進行。
2)所述質量對應於來自具有最高強度的[M+H]
+離子之同位素圖的峰。
#表示記錄[M-H]
-離子。
3)參考痕量CHCl
3在7.25 ppm處之訊號。
生物例 貓櫛頭蚤 (Ctenocephalides felis) – 體外接觸 試驗貓蚤成 蟲
實施例 | 結構 | NMR 峰列表 1) | ESI 質量 [m/z] 2) |
I-001 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8882 (3.5); 8.8802 (3.5); 8.8570 (0.1); 8.8489 (0.1); 8.5820 (1.1); 8.5741 (1.1); 8.0826 (3.3); 8.0321 (1.0); 7.9388 (1.1); 7.9257 (1.2); 7.8312 (0.4); 7.8185 (0.4); 7.7208 (0.7); 7.6292 (0.8); 7.6163 (1.7); 7.6033 (0.9); 7.5246 (1.0); 7.5165 (1.8); 7.5085 (1.0); 7.5012 (0.3); 7.4882 (0.5); 7.4754 (0.4); 7.4559 (0.5); 7.4411 (2.2); 7.4040 (1.3); 7.3913 (1.1); 7.3756 (0.3); 7.3677 (0.6); 7.3598 (0.3); 6.3835 (0.3); 6.3720 (1.1); 6.3605 (1.1); 6.3489 (0.4); 6.0869 (0.1); 6.0758 (0.4); 6.0644 (0.4); 6.0533 (0.1); 3.6669 (0.2); 3.6565 (0.2); 3.6433 (0.3); 3.6329 (0.3); 3.4706 (0.3); 3.4590 (0.3); 3.4471 (0.2); 3.4354 (0.2); 3.2626 (0.1); 3.1677 (0.1); 3.1291 (0.2); 3.1033 (0.1); 3.0978 (0.1); 3.0542 (16.0); 2.9368 (0.1); 2.8728 (0.3); 2.8611 (0.3); 2.8467 (1.1); 2.8349 (1.2); 2.8262 (1.1); 2.8168 (1.1); 2.8001 (0.4); 2.7906 (0.3); 2.3022 (11.0); 2.0805 (0.1); 2.0764 (0.1); 2.0723 (0.2); 2.0682 (0.1); 2.0641 (0.1); 1.9856 (0.2); 1.9775 (0.4); 1.9696 (9.8); 1.9655 (18.9); 1.9614 (27.6); 1.9573 (19.0); 1.9532 (9.6); 1.9445 (0.2); 1.9383 (0.1); 1.8544 (0.1); 1.8504 (0.2); 1.8463 (0.2); 1.8420 (0.3); 1.8326 (4.4); 1.8210 (4.5); 1.7774 (1.4); 1.7660 (1.4); 1.6565 (0.1); 1.6450 (0.1); 1.2597 (0.1); 1.0283 (0.2); 1.0180 (0.2); 1.0077 (0.2); 0.5828 (0.1); 0.5608 (0.4); 0.5512 (0.6); 0.5399 (0.5); 0.5184 (0.1); 0.4893 (0.1); 0.4749 (0.2); 0.4673 (0.3); 0.4612 (0.3); 0.4515 (0.4); 0.4434 (0.3); 0.4366 (0.3); 0.4293 (0.2); 0.4143 (0.1); 0.3269 (0.2); 0.3191 (0.3); 0.3113 (0.3); 0.3056 (0.2); 0.2729 (0.2); 0.2641 (0.3); 0.2578 (0.5); 0.2499 (0.7); 0.2430 (0.7); 0.2353 (0.5); 0.2287 (0.6); 0.2228 (0.7); 0.2158 (0.8); 0.2095 (0.9); 0.2017 (0.7); 0.1956 (0.4); 0.1866 (0.2); 0.0053 (0.1); -0.0001 (2.9); -0.0057 (0.1); -0.2168 (0.2); -0.2250 (0.5); -0.2330 (0.7); -0.2411 (0.8); -0.2483 (0.6); -0.2562 (0.2); -0.4070 (0.2); -0.4148 (0.6); -0.4221 (0.8); -0.4301 (0.7); -0.4382 (0.5); -0.4464 (0.2) | 427.3 | |
I-002 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 9.2407 (0.1); 9.0845 (2.5); 9.0810 (2.8); 9.0158 (0.8); 9.0130 (0.8); 8.8803 (5.1); 8.8722 (5.3); 8.7299 (0.9); 8.6226 (1.4); 8.6146 (1.5); 8.6065 (2.8); 8.6036 (3.0); 8.5852 (0.1); 8.5816 (0.1); 8.5781 (0.1); 8.1290 (0.8); 8.0950 (4.6); 8.0722 (0.1); 8.0472 (1.2); 7.9025 (1.5); 7.8992 (2.8); 7.8960 (1.8); 7.5181 (1.4); 7.5100 (2.7); 7.5020 (1.4); 7.4873 (0.1); 7.4134 (0.4); 7.4054 (0.7); 7.3974 (0.4); 6.4131 (0.4); 6.4015 (1.5); 6.3899 (1.6); 6.3783 (0.5); 6.0705 (0.2); 6.0591 (0.5); 6.0477 (0.5); 6.0363 (0.2); 3.6304 (0.3); 3.6196 (0.3); 3.6066 (0.4); 3.5959 (0.4); 3.4970 (0.4); 3.4855 (0.4); 3.4734 (0.3); 3.4619 (0.3); 3.2484 (0.1); 3.2396 (0.1); 3.2376 (0.1); 3.2012 (0.1); 3.1732 (0.4); 3.1681 (0.2); 3.1483 (0.1); 3.1337 (16.0); 3.0158 (0.1); 2.9411 (0.4); 2.9298 (0.4); 2.9148 (1.7); 2.9019 (2.4); 2.8912 (1.7); 2.8744 (0.4); 2.8648 (0.4); 2.3187 (0.1); 2.3153 (0.1); 2.2928 (45.2); 2.2601 (0.1); 2.1614 (0.1); 2.0924 (0.2); 2.0887 (0.1); 2.0801 (0.2); 2.0760 (0.3); 2.0719 (0.5); 2.0678 (0.3); 2.0637 (0.2); 2.0425 (0.1); 2.0113 (0.1); 2.0071 (0.1); 2.0030 (0.1); 1.9988 (0.1); 1.9946 (0.1); 1.9852 (1.2); 1.9771 (1.1); 1.9728 (1.8); 1.9693 (28.7); 1.9652 (56.0); 1.9610 (82.0); 1.9569 (56.9); 1.9528 (28.8); 1.9441 (0.3); 1.9366 (0.1); 1.9339 (0.1); 1.8542 (0.2); 1.8501 (0.4); 1.8459 (0.5); 1.8418 (0.4); 1.8306 (6.3); 1.8189 (6.3); 1.7936 (0.1); 1.7745 (1.9); 1.7630 (1.8); 1.3630 (0.1); 1.3515 (0.1); 1.2400 (0.1); 1.1574 (0.1); 1.1464 (0.1); 0.9749 (0.2); 0.9643 (0.3); 0.9545 (0.2); 0.6026 (0.1); 0.5932 (0.2); 0.5891 (0.2); 0.5806 (0.6); 0.5708 (0.7); 0.5601 (0.6); 0.5517 (0.3); 0.5473 (0.3); 0.5383 (0.1); 0.5211 (0.1); 0.5076 (0.1); 0.4668 (0.1); 0.4526 (0.2); 0.4444 (0.3); 0.4385 (0.4); 0.4292 (0.5); 0.4214 (0.4); 0.4142 (0.3); 0.4066 (0.2); 0.3919 (0.1); 0.3252 (0.1); 0.3172 (0.3); 0.3089 (0.4); 0.3029 (0.6); 0.2944 (0.6); 0.2880 (0.8); 0.2801 (1.0); 0.2722 (0.8); 0.2654 (0.6); 0.2578 (0.4); 0.2495 (0.4); 0.2407 (0.7); 0.2335 (0.7); 0.2271 (0.9); 0.2196 (0.6); 0.2134 (0.4); 0.2044 (0.2); 0.1758 (0.1); 0.1614 (0.3); 0.1557 (0.4); 0.1477 (0.3); 0.1401 (0.2); 0.1319 (0.1); 0.0968 (0.3); 0.0814 (0.1); 0.0419 (0.1); 0.0282 (0.1); 0.0227 (0.1); 0.0054 (2.0); -0.0001 (60.1); -0.0057 (1.8); -0.1001 (0.2); -0.1984 (0.3) | 428.2 | |
I-003 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8859 (4.9); 8.8778 (5.0); 8.6382 (1.6); 8.6302 (1.6); 8.0865 (4.4); 8.0335 (1.4); 8.0142 (0.1); 7.9580 (2.7); 7.9433 (0.1); 7.9060 (0.1); 7.8124 (1.0); 7.7920 (0.1); 7.6327 (1.0); 7.5286 (1.4); 7.5206 (2.6); 7.5125 (1.4); 7.4498 (3.6); 7.4167 (0.5); 7.4088 (0.9); 7.4007 (0.5); 7.3889 (2.9); 6.3593 (0.4); 6.3477 (1.4); 6.3361 (1.5); 6.3246 (0.5); 6.0860 (0.2); 6.0749 (0.5); 6.0634 (0.5); 6.0517 (0.2); 3.8379 (0.3); 3.6910 (0.3); 3.6808 (0.3); 3.6675 (0.4); 3.6571 (0.4); 3.5278 (0.4); 3.5160 (0.4); 3.5040 (0.3); 3.4922 (0.3); 3.1910 (0.1); 3.1259 (0.4); 3.1151 (0.3); 3.0769 (16.0); 3.0244 (0.2); 2.9592 (0.1); 2.9111 (0.6); 2.9037 (0.4); 2.8995 (0.6); 2.8849 (1.3); 2.8733 (1.4); 2.8440 (1.3); 2.8345 (1.3); 2.8178 (0.6); 2.8083 (0.6); 2.3015 (0.1); 2.2910 (81.9); 2.2744 (0.2); 2.2645 (0.1); 2.2585 (0.1); 2.0800 (0.2); 2.0759 (0.4); 2.0718 (0.6); 2.0677 (0.4); 2.0636 (0.2); 1.9851 (1.2); 1.9770 (1.0); 1.9726 (1.7); 1.9692 (37.9); 1.9651 (74.7); 1.9609 (110.4); 1.9568 (76.7); 1.9527 (39.4); 1.9440 (0.9); 1.9348 (0.4); 1.9307 (0.3); 1.9268 (0.2); 1.9226 (0.2); 1.9182 (0.2); 1.9138 (0.2); 1.9096 (0.1); 1.8950 (0.1); 1.8916 (0.1); 1.8873 (0.1); 1.8831 (0.1); 1.8789 (0.1); 1.8748 (0.1); 1.8707 (0.1); 1.8622 (0.1); 1.8541 (0.3); 1.8500 (0.5); 1.8458 (0.7); 1.8417 (0.5); 1.8376 (0.3); 1.8232 (6.0); 1.8116 (6.1); 1.7615 (2.1); 1.7501 (2.1); 1.7134 (0.1); 1.7019 (0.1); 1.5085 (0.1); 1.3213 (0.2); 1.3132 (0.2); 1.3096 (0.2); 1.3006 (0.2); 1.2879 (0.2); 1.2766 (0.2); 1.2716 (0.2); 1.0585 (0.2); 1.0481 (0.3); 1.0378 (0.2); 0.8970 (0.2); 0.8858 (0.5); 0.8738 (0.2); 0.5974 (0.1); 0.5877 (0.2); 0.5837 (0.2); 0.5752 (0.5); 0.5643 (0.7); 0.5544 (0.6); 0.5418 (0.3); 0.5325 (0.1); 0.5107 (0.1); 0.4954 (0.4); 0.4817 (0.6); 0.4741 (0.6); 0.4681 (0.6); 0.4602 (0.4); 0.4523 (0.3); 0.4374 (0.1); 0.3496 (0.1); 0.3420 (0.2); 0.3336 (0.3); 0.3259 (0.4); 0.3209 (0.3); 0.3083 (0.3); 0.2991 (0.4); 0.2929 (0.7); 0.2851 (0.9); 0.2777 (0.8); 0.2702 (0.8); 0.2622 (1.1); 0.2528 (1.0); 0.2459 (0.9); 0.2398 (1.0); 0.2322 (0.7); 0.2254 (0.4); 0.2170 (0.2); 0.0967 (0.4); 0.0109 (0.2); 0.0054 (2.2); -0.0001 (84.9); -0.0057 (3.1); -0.0124 (1.5); -0.0265 (0.1); -0.0319 (0.1); -0.0376 (0.1); -0.0430 (0.1); -0.0580 (0.1); -0.0820 (0.1); -0.1002 (0.4); -0.1791 (0.3); -0.1875 (0.7); -0.1954 (1.0) | 461.1 | |
I-004 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0075 (1.3); 8.9908 (14.0); 8.9787 (14.1); 8.7288 (6.2); 8.7167 (6.3); 8.3166 (0.8); 8.2715 (15.2); 8.2343 (5.1); 8.1865 (3.0); 8.1744 (2.9); 8.0920 (0.9); 8.0096 (1.7); 7.9930 (2.6); 7.9123 (0.4); 7.6873 (4.6); 7.6751 (8.9); 7.6630 (4.9); 7.6507 (0.5); 7.6103 (0.4); 7.5666 (1.2); 7.4133 (0.6); 7.3914 (0.7); 7.3647 (0.6); 7.3083 (0.4); 7.2708 (0.5); 7.2647 (0.4); 7.2496 (0.4); 7.2433 (0.4); 7.2023 (0.4); 6.6627 (0.3); 6.5048 (1.0); 5.9824 (0.4); 5.9656 (1.3); 5.9484 (1.3); 5.9309 (0.4); 5.3358 (0.4); 5.3241 (0.8); 5.3120 (0.5); 3.7163 (0.4); 3.6970 (0.5); 3.6593 (1.4); 3.6421 (1.4); 3.6237 (0.6); 3.6065 (0.6); 3.3252 (162.0); 2.9782 (1.4); 2.9624 (2.5); 2.9465 (2.2); 2.9304 (1.0); 2.9111 (1.3); 2.8004 (2.2); 2.7853 (2.3); 2.7609 (1.5); 2.7460 (1.4); 2.6761 (2.0); 2.6715 (3.0); 2.6670 (2.0); 2.6625 (1.0); 2.5878 (0.4); 2.5249 (9.5); 2.5114 (167.2); 2.5071 (328.6); 2.5026 (427.6); 2.4980 (311.9); 2.4937 (152.6); 2.3384 (0.9); 2.3339 (1.9); 2.3294 (2.6); 2.3250 (1.9); 2.1209 (0.4); 2.1052 (0.4); 2.0274 (0.9); 2.0089 (1.7); 1.9900 (1.6); 1.9738 (0.7); 1.9576 (0.4); 1.7773 (16.0); 1.7598 (16.0); 1.7099 (5.9); 1.6927 (5.8); 1.6255 (0.3); 1.6084 (0.4); 1.5705 (0.4); 1.4736 (0.6); 1.4553 (0.7); 1.4419 (0.5); 1.3880 (0.7); 1.3820 (1.1); 1.3647 (1.0); 1.3526 (0.7); 1.3451 (0.4); 1.3359 (1.6); 1.2984 (9.1); 1.2896 (2.4); 1.2809 (1.9); 1.2589 (13.4); 1.2494 (5.6); 1.2353 (13.8); 1.1883 (0.4); 1.1376 (0.3); 1.0984 (0.6); 1.0894 (0.6); 1.0723 (0.5); 1.0614 (0.6); 1.0455 (0.4); 1.0331 (0.4); 1.0185 (0.4); 0.9247 (0.5); 0.9053 (0.5); 0.8998 (0.4); 0.8878 (0.6); 0.8707 (1.5); 0.8541 (3.3); 0.8366 (1.4); 0.6939 (0.4); 0.6769 (0.8); 0.4756 (1.6); 0.4600 (1.7); 0.4413 (1.8); 0.4275 (2.7); 0.4175 (2.7); 0.4132 (2.9); 0.4081 (2.2); 0.3972 (2.1); 0.3930 (2.0); 0.3830 (0.8); 0.3271 (1.4); 0.2464 (0.8); 0.2340 (0.8); 0.2240 (1.8); 0.2122 (2.8); 0.2038 (4.1); 0.1937 (3.4); 0.1843 (3.7); 0.1677 (1.8); 0.1574 (2.0); 0.1542 (2.0); 0.1456 (1.5); 0.1419 (1.8); 0.1314 (0.4); 0.0079 (0.4); -0.0002 (12.0); -0.0086 (0.4); -0.2736 (0.7); -0.2855 (1.5); -0.2983 (1.8); -0.3087 (2.2); -0.4265 (1.6) | 469.1 | |
I-005 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 9.0235 (0.2); 9.0154 (0.1); 8.9241 (0.4); 8.9161 (0.4); 8.9092 (0.3); 8.9011 (0.4); 8.8879 (0.9); 8.8764 (12.2); 8.8684 (12.2); 8.7211 (0.1); 8.7130 (0.1); 8.5912 (0.3); 8.5831 (0.5); 8.5723 (2.6); 8.5645 (2.6); 8.4517 (0.1); 8.3799 (0.1); 8.2586 (0.1); 8.2337 (0.1); 8.2199 (0.1); 8.1799 (0.2); 8.1638 (0.2); 8.1513 (0.1); 8.1383 (0.1); 8.1122 (3.6); 8.0990 (4.0); 8.0877 (11.2); 8.0726 (0.8); 8.0596 (0.6); 8.0393 (2.6); 8.0250 (1.0); 8.0122 (1.0); 7.9954 (0.1); 7.9814 (0.1); 7.9643 (0.1); 7.9586 (0.1); 7.9462 (0.2); 7.9321 (0.2); 7.9115 (1.8); 7.8855 (0.1); 7.8806 (0.1); 7.8713 (0.1); 7.8636 (0.1); 7.8547 (0.1); 7.7884 (2.8); 7.7754 (5.8); 7.7623 (3.3); 7.7223 (0.6); 7.7106 (1.6); 7.7034 (1.4); 7.6904 (1.3); 7.6755 (4.9); 7.6624 (3.7); 7.6295 (6.8); 7.6139 (0.1); 7.5380 (0.2); 7.5276 (0.3); 7.5165 (3.4); 7.5084 (6.4); 7.5004 (3.2); 7.4879 (0.2); 7.4743 (0.2); 7.4507 (0.5); 7.4369 (0.4); 7.3810 (0.9); 7.3734 (1.4); 7.3656 (0.7); 6.5009 (0.1); 6.4358 (0.1); 6.4239 (0.2); 6.4066 (1.2); 6.3951 (3.8); 6.3835 (3.8); 6.3719 (1.2); 6.2934 (0.1); 6.2818 (0.1); 6.1368 (0.1); 6.1334 (0.1); 6.0337 (0.3); 6.0227 (0.9); 6.0113 (0.9); 6.0002 (0.3); 5.9466 (0.1); 5.9354 (0.1); 5.6189 (0.1); 5.6035 (0.1); 5.4721 (9.8); 5.3607 (0.3); 5.3524 (0.5); 5.3443 (0.3); 5.3369 (0.1); 5.3189 (0.1); 3.7124 (0.1); 3.6988 (0.1); 3.6872 (0.6); 3.6767 (0.6); 3.6635 (0.7); 3.6531 (0.7); 3.5619 (0.1); 3.5496 (0.1); 3.5375 (0.1); 3.4961 (0.7); 3.4845 (0.7); 3.4722 (0.6); 3.4607 (0.6); 3.4443 (0.1); 3.4363 (0.1); 3.4337 (0.1); 3.4258 (0.1); 3.2372 (0.1); 3.2270 (0.1); 3.2162 (0.1); 3.1097 (0.1); 3.0986 (0.1); 3.0329 (0.5); 3.0220 (0.8); 3.0115 (0.5); 3.0015 (0.1); 2.9900 (0.2); 2.9792 (0.1); 2.9472 (0.1); 2.9183 (0.3); 2.9104 (0.3); 2.8935 (0.1); 2.8817 (0.1); 2.8719 (0.3); 2.8671 (0.3); 2.8612 (0.3); 2.8454 (9.0); 2.8349 (9.8); 2.8193 (0.4); 2.8088 (0.1); 2.8035 (0.1); 2.7934 (0.1); 2.7793 (0.1); 2.7300 (0.5); 2.6637 (0.6); 2.5973 (0.1); 2.3290 (0.1); 2.3232 (0.1); 2.3147 (0.2); 2.2914 (121.5); 2.2685 (0.2); 2.2560 (0.3); 2.2479 (0.1); 2.2427 (0.1); 2.1918 (0.1); 2.1103 (0.5); 2.0978 (1.0); 2.0851 (0.6); 2.0801 (0.4); 2.0760 (0.7); 2.0719 (1.0); 2.0678 (0.7); 2.0637 (0.4); 2.0497 (0.1); 2.0456 (0.1); 2.0324 (0.2); 2.0210 (0.6); 2.0114 (0.6); 2.0001 (0.4); 1.9925 (0.2); 1.9852 (1.6); 1.9771 (2.6); 1.9692 (61.6); 1.9651 (119.3); 1.9610 (175.6); 1.9569 (122.8); 1.9529 (63.2); 1.9354 (0.3); 1.9262 (0.2); 1.9229 (0.2); 1.9180 (0.2); 1.8958 (0.1); 1.8917 (0.1); 1.8870 (0.1); 1.8830 (0.1); 1.8780 (0.1); 1.8736 (0.1); 1.8687 (0.1); 1.8540 (0.5); 1.8501 (0.8); 1.8459 (1.2); 1.8418 (1.1); 1.8292 (15.8); 1.8176 (16.0); 1.7871 (0.2); 1.7838 (0.2); 1.7491 (3.9); 1.7377 (3.8); 1.7109 (0.2); 1.7000 (0.1); 1.6931 (0.1); 1.6813 (0.1); 1.6756 (0.1); 1.6602 (0.1); 1.6408 (0.1); 1.6271 (0.1); 1.6043 (0.1); 1.5882 (0.1); 1.5350 (0.2); 1.5249 (0.6); 1.5134 (0.6); 1.5001 (0.3); 1.4780 (0.1); 1.4701 (0.1); 1.4580 (0.1); 1.4486 (0.1); 1.4441 (0.1); 1.4279 (0.1); 1.4208 (0.1); 1.4108 (0.4); 1.4029 (0.2); 1.3906 (0.2); 1.3771 (0.1); 1.3630 (0.2); 1.3517 (0.2); 1.3408 (0.9); 1.3086 (0.8); 1.2826 (2.9); 1.2601 (9.1); 1.2169 (0.2); 1.2069 (0.2); 1.1912 (0.4); 1.1758 (0.2); 1.1598 (0.2); 1.1519 (0.1); 1.1420 (0.1); 1.1358 (0.1); 1.1246 (0.4); 1.1098 (0.1); 1.0974 (0.1); 1.0942 (0.1); 1.0852 (0.5); 1.0737 (1.6); 1.0617 (0.4); 1.0506 (0.6); 1.0463 (1.8); 1.0403 (1.6); 1.0294 (1.5); 1.0204 (0.9); 0.9820 (0.1); 0.9688 (0.2); 0.9578 (0.2); 0.9493 (0.2); 0.9452 (0.2); 0.9372 (0.2); 0.9327 (0.2); 0.9246 (0.3); 0.9168 (0.2); 0.9124 (0.2); 0.8927 (1.1); 0.8816 (2.2); 0.8697 (1.2); 0.8528 (0.5); 0.8404 (0.3); 0.8151 (0.1); 0.8045 (0.2); 0.7922 (0.1); 0.7816 (0.1); 0.7654 (0.1); 0.5550 (0.2); 0.5415 (0.7); 0.5320 (1.6); 0.5225 (2.2); 0.5121 (1.7); 0.4997 (0.9); 0.4890 (0.5); 0.4801 (0.6); 0.4641 (1.1); 0.4570 (1.5); 0.4434 (1.2); 0.4346 (0.7); 0.4222 (0.2); 0.3916 (0.1); 0.3844 (0.1); 0.3712 (0.1); 0.3638 (0.1); 0.3564 (0.1); 0.3392 (0.3); 0.3317 (0.5); 0.3236 (0.7); 0.3157 (0.8); 0.2837 (0.1); 0.2734 (0.2); 0.2602 (0.6); 0.2515 (1.0); 0.2451 (1.9); 0.2369 (2.6); 0.2299 (2.7); 0.2228 (2.4); 0.2150 (2.9); 0.2066 (2.4); 0.1995 (2.3); 0.1932 (2.5); 0.1842 (2.0); 0.1721 (1.0); 0.0970 (0.1); 0.0786 (0.2); 0.0243 (0.1); 0.0183 (0.1); 0.0054 (0.6); -0.0001 (19.3); -0.1005 (0.1); --0.2529 (0.8); -0.2613 (1.9); -0.2693 (2.7); -0.2772 (2.8); -0.2847 (2.1); -0.2926 (0.8); -0.4435 (0.9); -0.4514 (2.2); -0.4590 (2.8); -0.4670 (2.6); -0.4751 (1.8); -0.4833 (0.7); | 481.1 | |
I-006 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 9.2302 (6.6); 9.2274 (6.7); 9.1826 (1.7); 8.9662 (1.9); 8.9087 (0.5); 8.9007 (0.5); 8.8787 (2.9); 8.8703 (3.8); 8.8654 (12.4); 8.8574 (12.6); 8.8275 (7.5); 8.8254 (7.6); 8.6277 (2.7); 8.6197 (2.8); 8.3294 (1.7); 8.1796 (0.4); 8.1376 (6.8); 8.1175 (1.5); 8.1002 (11.3); 8.0520 (2.4); 8.0396 (2.5); 7.5115 (1.0); 7.5064 (3.7); 7.4987 (6.7); 7.4907 (3.4); 7.4278 (0.8); 7.4200 (1.4); 7.4122 (0.8); 6.5577 (1.0); 6.5466 (1.0); 6.5358 (0.3); 6.4315 (1.2); 6.4199 (4.0); 6.4083 (4.0); 6.3967 (1.3); 6.0178 (0.3); 6.0063 (0.9); 5.9951 (1.0); 5.9841 (0.3); 5.4718 (1.0); 4.0126 (0.4); 3.6765 (0.4); 3.6651 (0.6); 3.6536 (0.5); 3.6472 (0.5); 3.6366 (0.6); 3.6231 (0.8); 3.6129 (0.7); 3.5180 (0.7); 3.5065 (0.8); 3.4942 (0.6); 3.4825 (0.5); 2.9753 (0.3); 2.9512 (1.3); 2.9391 (0.3); 2.9252 (9.0); 2.9150 (12.1); 2.8985 (0.4); 2.6633 (1.4); 2.2933 (196.3); 2.2680 (0.4); 2.2609 (0.4); 2.0791 (0.5); 2.0756 (0.8); 2.0715 (1.2); 2.0675 (0.8); 2.0633 (0.5); 1.9848 (1.4); 1.9761 (3.4); 1.9687 (76.1); 1.9647 (147.0); 1.9607 (213.5); 1.9566 (152.8); 1.9526 (80.3); 1.9335 (9.5); 1.9155 (0.4); 1.8537 (0.6); 1.8496 (1.0); 1.8455 (1.4); 1.8415 (1.2); 1.8287 (15.9); 1.8171 (16.0); 1.7445 (3.8); 1.7331 (3.7); 1.6784 (4.3); 1.6674 (4.4); 1.5403 (0.5); 1.5286 (0.5); 1.3405 (0.7); 1.3081 (0.3); 1.3040 (0.3); 1.2922 (0.4); 1.2823 (1.2); 1.2733 (1.6); 1.2612 (2.9); 1.2321 (7.1); 1.2273 (7.1); 1.2208 (7.2); 1.2159 (6.9); 0.9618 (0.7); 0.8808 (0.5); 0.8689 (0.3); 0.5943 (0.7); 0.5820 (1.6); 0.5724 (2.2); 0.5622 (1.7); 0.5504 (0.8); 0.4540 (0.6); 0.4395 (1.0); 0.4301 (1.0); 0.4160 (0.8); 0.4085 (0.6); 0.3218 (0.6); 0.3138 (0.8); 0.3044 (1.4); 0.2961 (1.5); 0.2893 (2.1); 0.2814 (2.7); 0.2745 (2.3); 0.2675 (1.7); 0.2589 (1.1); 0.2426 (1.1); 0.2338 (1.8); 0.2268 (2.0); 0.2203 (2.5); 0.2126 (1.8); 0.2064 (1.1); 0.1975 (0.7); 0.1615 (0.6); 0.1561 (0.8); 0.1481 (0.7); 0.1403 (0.5); -0.0004 (2.1) | 482.1 | |
I-007 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8814 (10.7); 8.8737 (11.2); 8.5786 (6.4); 8.5711 (6.7); 8.0847 (10.6); 8.0271 (6.1); 7.7796 (8.5); 7.6351 (4.9); 7.5179 (3.1); 7.5103 (5.7); 7.5026 (3.2); 7.3731 (1.9); 7.3656 (3.5); 7.3531 (5.1); 7.2899 (9.2); 7.2422 (4.0); 7.2105 (4.6); 7.1805 (8.8); 7.1514 (2.8); 6.3776 (1.3); 6.3662 (3.9); 6.3546 (4.0); 6.3433 (1.4); 6.1082 (0.8); 6.0972 (2.3); 6.0859 (2.4); 6.0751 (0.9); 5.4727 (6.8); 3.6771 (1.3); 3.6669 (1.4); 3.6537 (1.9); 3.6434 (1.9); 3.5426 (1.8); 3.5309 (1.9); 3.5191 (1.4); 3.5074 (1.3); 2.9230 (2.1); 2.9113 (2.2); 2.8969 (3.4); 2.8853 (3.4); 2.8126 (5.5); 2.8036 (6.9); 2.7937 (4.7); 2.7876 (5.7); 2.7780 (3.7); 2.6208 (0.5); 2.3084 (105.2); 2.0981 (0.5); 2.0853 (0.3); 2.0730 (0.6); 2.0198 (0.4); 2.0089 (0.3); 1.9851 (0.7); 1.9621 (89.4); 1.9606 (87.8); 1.8468 (0.7); 1.8164 (15.8); 1.8049 (16.0); 1.7567 (9.2); 1.7453 (9.0); 1.3067 (0.4); 1.2590 (3.0); 1.0581 (1.3); 1.0485 (1.6); 1.0386 (1.3); 0.8916 (0.5); 0.8808 (0.8); 0.8691 (0.5); 0.7670 (5.3); 0.7549 (7.2); 0.7443 (9.6); 0.7336 (8.5); 0.7093 (0.3); 0.6131 (5.2); 0.5723 (11.3); 0.4723 (2.7); 0.4583 (2.0); 0.3441 (1.4); 0.3354 (1.8); 0.3286 (2.1); 0.2943 (1.0); 0.2710 (4.7); 0.2645 (4.7); 0.2578 (3.8); 0.2493 (2.6); 0.2351 (2.6); 0.2283 (2.8); 0.2219 (3.0); 0.2142 (2.3); 0.1992 (0.9); 0.1771 (0.3); 0.1647 (0.3); 0.1539 (0.4); 0.1472 (0.4); 0.1378 (0.4); 0.1246 (0.5); 0.0968 (6.6); 0.0848 (1.0); 0.0656 (0.9); 0.0573 (1.0); 0.0475 (1.2); 0.0364 (2.0); -0.0001 (1003.2); -0.1002 (5.6); -0.1764 (0.7); -0.1839 (2.0); -0.1918 (2.8); -0.1995 (3.0); -0.2071 (2.2); -0.3887 (2.4); -0.3963 (3.0); -0.4040 (2.8); -0.4118 (1.9); -0.4195 (0.7) | 466.2 | |
I-008 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8858 (10.2); 8.8777 (11.8); 8.8690 (2.3); 8.6013 (0.7); 8.5932 (0.8); 8.5453 (4.6); 8.5375 (4.7); 8.0849 (2.0); 8.0751 (9.2); 8.0299 (0.9); 8.0196 (4.1); 7.9337 (1.2); 7.7617 (0.5); 7.5310 (2.9); 7.5230 (5.9); 7.5150 (4.1); 7.4686 (1.3); 7.4588 (0.6); 7.4142 (6.4); 7.3991 (0.4); 7.3913 (0.5); 7.3840 (0.3); 7.3599 (1.5); 7.3520 (2.5); 7.3444 (1.4); 7.2916 (1.2); 7.1941 (3.4); 7.1820 (2.8); 6.9747 (6.4); 6.9224 (2.6); 6.8511 (6.5); 6.3725 (1.2); 6.3614 (3.5); 6.3499 (3.5); 6.3386 (1.2); 6.1483 (0.6); 6.1372 (1.7); 6.1255 (1.8); 6.1138 (0.8); 6.1027 (0.3); 3.7401 (0.9); 3.7298 (1.0); 3.7163 (1.3); 3.7060 (1.3); 3.5349 (1.3); 3.5225 (1.4); 3.5113 (1.0); 3.4993 (1.0); 2.9251 (0.3); 2.9136 (0.3); 2.8988 (0.5); 2.8873 (0.5); 2.8620 (1.7); 2.8501 (1.7); 2.8358 (2.9); 2.8242 (3.3); 2.7989 (0.4); 2.7887 (0.4); 2.7636 (2.7); 2.7541 (2.8); 2.7372 (1.7); 2.7281 (1.6); 2.3199 (0.6); 2.2912 (562.0); 2.2665 (0.7); 2.2584 (0.8); 2.0977 (0.4); 2.0798 (1.3); 2.0756 (2.4); 2.0716 (3.5); 2.0675 (2.4); 2.0634 (1.3); 2.0071 (0.6); 1.9849 (4.8); 1.9688 (219.6); 1.9648 (416.4); 1.9607 (595.7); 1.9567 (418.5); 1.9526 (216.5); 1.9322 (1.7); 1.9170 (0.5); 1.9085 (0.4); 1.8984 (0.5); 1.8943 (0.5); 1.8907 (0.5); 1.8866 (0.4); 1.8536 (1.5); 1.8497 (2.8); 1.8456 (3.8); 1.8415 (3.2); 1.8375 (2.3); 1.8222 (14.5); 1.8108 (16.0); 1.8008 (3.5); 1.7553 (6.8); 1.7439 (6.7); 1.5047 (0.3); 1.3084 (0.5); 1.3021 (0.6); 1.2609 (4.0); 1.2424 (0.6); 1.0878 (1.2); 1.0772 (1.1); 1.0587 (0.7); 1.0379 (7.1); 1.0268 (7.4); 0.9901 (0.4); 0.8938 (0.5); 0.8819 (0.9); 0.8699 (0.5); 0.6964 (6.3); 0.6887 (6.3); 0.6710 (1.1); 0.6525 (1.6); 0.6283 (1.4); 0.6100 (0.6); 0.5469 (0.5); 0.5253 (2.0); 0.5141 (2.8); 0.5047 (2.9); 0.4933 (2.5); 0.4827 (1.8); 0.4760 (1.4); 0.3537 (0.8); 0.3448 (1.2); 0.3377 (1.5); 0.3010 (1.6); 0.2933 (1.4); 0.2865 (1.2); 0.2780 (1.4); 0.2699 (1.4); 0.2629 (2.0); 0.2549 (2.5); 0.2481 (2.3); 0.2406 (2.0); 0.2337 (2.4); 0.2267 (2.2); 0.2189 (2.3); 0.2127 (2.3); 0.2050 (1.6); 0.1900 (0.5); -0.0001 (5.8) | 457.2 | |
I-009 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.9038 (12.6); 8.8958 (12.6); 8.8752 (0.3); 8.6657 (7.4); 8.6577 (7.5); 8.6387 (7.2); 8.6307 (7.3); 8.0884 (10.0); 8.0811 (6.6); 8.0303 (6.6); 8.0201 (6.4); 7.6627 (5.4); 7.6589 (5.6); 7.6387 (3.4); 7.6348 (3.6); 7.5373 (2.0); 7.5306 (4.9); 7.5232 (6.6); 7.5154 (3.1); 7.4320 (2.1); 7.4236 (6.9); 7.4159 (2.2); 7.4115 (2.3); 7.4033 (3.8); 7.3953 (1.9); 7.3819 (3.9); 7.3781 (3.5); 7.2936 (3.6); 7.2897 (3.8); 7.2152 (3.4); 7.2115 (3.5); 7.0104 (0.3); 6.9806 (5.6); 6.9768 (5.8); 6.7777 (0.6); 6.7661 (2.0); 6.7544 (2.0); 6.7428 (0.6); 6.6507 (3.6); 6.6469 (3.8); 6.3954 (0.9); 6.3840 (2.9); 6.3725 (3.0); 6.3611 (1.0); 6.1431 (0.7); 6.1316 (2.2); 6.1201 (2.2); 6.1086 (0.7); 5.9389 (0.7); 5.9273 (2.2); 5.9158 (2.2); 5.9042 (0.7); 3.8724 (1.2); 3.8618 (1.2); 3.8488 (2.2); 3.8381 (2.1); 3.8285 (2.0); 3.8182 (1.9); 3.7746 (3.0); 3.7625 (2.9); 3.7512 (1.8); 3.7391 (1.7); 2.9914 (1.9); 2.9795 (1.9); 2.9652 (2.7); 2.9533 (2.7); 2.8568 (0.9); 2.8493 (2.7); 2.8403 (2.6); 2.8307 (2.1); 2.8207 (2.7); 2.8143 (2.0); 2.7960 (2.0); 2.7854 (2.0); 2.7698 (0.8); 2.7592 (0.8); 2.2937 (173.9); 2.0796 (0.3); 2.0756 (0.7); 2.0715 (1.0); 2.0675 (0.7); 2.0634 (0.4); 1.9848 (18.1); 1.9763 (3.6); 1.9687 (58.9); 1.9647 (113.2); 1.9606 (164.9); 1.9566 (118.0); 1.9526 (61.8); 1.8538 (0.4); 1.8496 (0.7); 1.8456 (1.0); 1.8415 (0.8); 1.8371 (0.6); 1.8265 (8.8); 1.8148 (8.8); 1.7955 (13.8); 1.7835 (16.0); 1.7692 (8.9); 1.7547 (0.4); 1.7426 (0.4); 1.7284 (8.7); 1.7169 (8.6); 1.2674 (0.5); 1.2590 (1.0); 1.2473 (1.1); 1.2360 (0.8); 1.2275 (0.4); 1.1902 (0.6); 1.1793 (0.7); 1.1696 (0.4); 1.1607 (0.8); 1.1493 (1.0); 1.1386 (0.8); 1.1301 (0.4); 0.5975 (0.3); 0.5921 (0.8); 0.5832 (1.2); 0.5780 (2.1); 0.5703 (1.9); 0.5640 (2.4); 0.5567 (1.8); 0.5496 (1.9); 0.5426 (1.6); 0.5358 (1.8); 0.5247 (1.5); 0.5192 (1.7); 0.5114 (2.0); 0.5044 (2.6); 0.4954 (2.6); 0.4865 (2.1); 0.4791 (1.4); 0.4706 (0.6); 0.4222 (0.6); 0.4146 (1.5); 0.4076 (2.0); 0.4001 (2.1); 0.3929 (2.3); 0.3862 (1.7); 0.3786 (0.8); 0.3716 (1.0); 0.3642 (1.9); 0.3574 (2.5); 0.3491 (2.3); 0.3436 (2.0); 0.3353 (1.6); 0.3234 (0.6); 0.3036 (0.4); 0.2948 (0.6); 0.2883 (1.0); 0.2806 (1.3); 0.2735 (1.2); 0.2667 (0.9); 0.2563 (0.9); 0.2477 (1.1); 0.2400 (1.2); 0.2335 (1.3); 0.2258 (1.0); 0.2195 (0.5); 0.2109 (0.4); 0.2028 (0.4); 0.1876 (1.4); 0.1797 (5.3); 0.1734 (2.2); 0.1663 (5.1); 0.1589 (1.3); 0.1438 (0.3); -0.0008 (1.9); -0.1766 (0.4); -0.1845 (1.0); -0.1927 (1.4) | 453.0 | |
I-010 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8877 (10.7); 8.8798 (10.9); 8.4298 (4.4); 8.4222 (4.4); 8.0879 (9.7); 8.0212 (3.8); 7.9780 (7.1); 7.8159 (3.1); 7.6340 (7.5); 7.6213 (9.5); 7.5863 (3.2); 7.5733 (5.1); 7.5414 (0.4); 7.5245 (7.1); 7.5118 (16.0); 7.4999 (14.4); 7.4687 (4.8); 7.4553 (11.0); 7.4251 (2.7); 7.2610 (7.0); 7.2243 (1.3); 7.2170 (2.3); 7.2094 (1.3); 6.4237 (1.2); 6.4123 (3.5); 6.4009 (3.6); 6.3894 (1.2); 6.2534 (0.6); 6.2425 (1.6); 6.2312 (1.6); 6.2195 (0.6); 3.7846 (0.9); 3.7746 (1.0); 3.7610 (1.2); 3.7508 (1.2); 3.5819 (1.1); 3.5707 (1.2); 3.5587 (1.0); 3.5471 (0.9); 2.9461 (1.8); 2.9347 (1.9); 2.9202 (3.0); 2.9085 (3.0); 2.8484 (2.9); 2.8391 (3.0); 2.8223 (1.8); 2.8131 (1.8); 2.2920 (255.9); 2.2596 (0.5); 2.0758 (1.1); 2.0718 (1.6); 2.0677 (1.2); 1.9850 (2.7); 1.9689 (101.5); 1.9650 (197.7); 1.9609 (288.0); 1.9569 (211.8); 1.9530 (113.5); 1.9185 (0.3); 1.8533 (14.8); 1.8418 (15.6); 1.8102 (0.4); 1.7813 (6.0); 1.7699 (5.8); 1.2604 (0.4); 1.1201 (1.0); 1.1106 (0.8); 0.5842 (1.6); 0.5748 (2.1); 0.5645 (1.8); 0.5416 (0.5); 0.5094 (1.9); 0.4952 (1.3); 0.3755 (0.8); 0.3594 (1.4); 0.3235 (1.4); 0.2803 (0.7); 0.2653 (1.8); 0.2571 (2.6); 0.2506 (2.5); 0.2414 (2.6); 0.2343 (2.6); 0.2257 (2.4); 0.2195 (2.5); 0.2115 (1.7); 0.1965 (0.6); -0.0001 (3.0) | 493.2 | |
I-011 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0428 (5.9); 9.0308 (6.0); 8.8655 (9.1); 8.8534 (9.2); 8.2697 (5.6); 8.1855 (8.4); 7.8423 (3.5); 7.8178 (4.9); 7.7835 (3.5); 7.6910 (1.7); 7.6790 (3.1); 7.6669 (1.8); 7.6437 (3.9); 7.6300 (5.3); 7.5836 (2.6); 7.5715 (4.8); 7.5595 (2.4); 7.5099 (5.0); 6.2877 (0.8); 6.2709 (2.9); 6.2535 (3.3); 6.2424 (2.2); 6.2255 (1.8); 6.2088 (0.6); 5.7578 (8.2); 4.2199 (1.7); 4.1796 (2.4); 4.0156 (2.4); 3.9754 (1.6); 3.7437 (11.4); 3.3265 (31.2); 3.1882 (0.3); 3.1614 (4.8); 3.1466 (4.6); 3.1205 (0.3); 3.0457 (0.9); 3.0298 (1.0); 3.0106 (1.4); 2.9944 (1.4); 2.9184 (1.4); 2.9017 (1.5); 2.8830 (0.9); 2.8660 (0.9); 2.6764 (0.7); 2.6721 (1.0); 2.6678 (0.7); 2.5076 (124.5); 2.5033 (158.7); 2.4989 (120.3); 2.3343 (0.8); 2.3300 (1.0); 2.3256 (0.8); 1.6206 (16.0); 1.6031 (15.0); 1.2347 (1.3); 0.7482 (1.1); 0.7352 (1.5); 0.7221 (1.2); 0.7026 (0.6); 0.4515 (0.4); 0.4374 (0.7); 0.4289 (1.4); 0.4166 (1.9); 0.4068 (2.0); 0.3953 (1.9); 0.3836 (2.3); 0.3713 (2.1); 0.3607 (2.3); 0.3504 (2.1); 0.3393 (1.5); 0.3166 (0.5); 0.2063 (0.6); 0.1944 (1.3); 0.1826 (1.8); 0.1706 (2.0); 0.1600 (1.4); 0.1470 (0.8); 0.0971 (3.1); 0.0769 (2.8); 0.0077 (2.3); -0.0001 (46.9); -0.0081 (3.0); -0.0380 (1.8); -0.0503 (2.4); -0.0612 (2.1); -0.0733 (1.9); -0.0852 (1.2); -0.0975 (0.5); -0.4153 (1.1); -0.4279 (1.3); -0.4402 (1.0) | 465.1 | |
I-012 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8832 (10.1); 8.8751 (10.2); 8.4293 (3.7); 8.4214 (3.7); 8.0876 (9.2); 8.0203 (3.3); 7.9481 (5.4); 7.7828 (2.4); 7.6550 (3.8); 7.6460 (4.5); 7.6407 (4.8); 7.6317 (4.2); 7.6088 (1.6); 7.5953 (2.0); 7.5863 (1.6); 7.5219 (1.9); 7.5040 (2.9); 7.4960 (5.4); 7.4879 (2.8); 7.4250 (2.0); 7.4037 (5.5); 7.2771 (5.6); 7.2624 (16.0); 7.2479 (5.6); 7.2260 (1.1); 7.2180 (1.9); 7.2100 (1.0); 6.4163 (0.9); 6.4047 (3.0); 6.3932 (3.0); 6.3815 (1.0); 6.2197 (1.2); 6.2085 (1.2); 3.7857 (0.7); 3.7756 (0.8); 3.7624 (0.9); 3.7520 (0.9); 3.5883 (0.9); 3.5767 (1.0); 3.5648 (0.8); 3.5529 (0.7); 3.0550 (0.7); 2.9426 (2.1); 2.9303 (1.5); 2.9157 (2.5); 2.9041 (2.5); 2.8458 (2.4); 2.8363 (2.5); 2.8196 (1.5); 2.8102 (1.4); 2.2921 (303.8); 2.0802 (0.6); 2.0761 (1.1); 2.0720 (1.7); 2.0679 (1.1); 2.0637 (0.6); 1.9929 (0.6); 1.9853 (39.7); 1.9771 (3.3); 1.9693 (102.4); 1.9652 (200.4); 1.9611 (294.3); 1.9570 (202.3); 1.9528 (102.3); 1.8793 (0.3); 1.8516 (12.5); 1.8460 (4.3); 1.8401 (12.6); 1.7779 (4.8); 1.7664 (4.7); 1.1240 (0.8); 0.5728 (1.5); 0.5120 (1.3); 0.3616 (1.0); 0.3288 (1.0); 0.2814 (0.5); 0.2664 (1.4); 0.2586 (1.9); 0.2516 (1.8); 0.2426 (1.7); 0.2347 (1.8); 0.2260 (1.7); 0.2196 (1.8); 0.2119 (1.3); 0.1969 (0.4); 0.0967 (1.4); 0.0054 (9.4); -0.0001 (312.2); -0.0057 (9.8); -0.1002 (1.4); -0.2063 (0.6); -0.2145 (1.4); -0.2225 (2.0); -0.2306 (2.2); -0.2376 (1.6); -0.2455 (0.7); -0.3760 (1.6); -0.3831 (2.1); -0.3911 (2.0); -0.3991 (1.3) | 511.1 | |
I-013 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.9065 (11.2); 8.8986 (16.0); 8.8914 (6.3); 8.5721 (5.5); 8.5640 (5.6); 8.5376 (5.2); 8.5295 (5.3); 8.0804 (9.9); 8.0705 (5.4); 8.0136 (7.2); 7.5347 (3.0); 7.5266 (5.9); 7.5187 (4.1); 7.5117 (3.2); 7.5036 (1.6); 7.4280 (3.2); 7.4146 (5.5); 7.3866 (2.3); 7.3743 (3.8); 7.3668 (2.2); 7.3589 (4.0); 7.3508 (2.2); 7.3362 (7.1); 7.3254 (7.9); 7.3178 (2.1); 7.3102 (5.4); 7.2976 (4.2); 7.2852 (1.9); 7.1556 (0.7); 7.1508 (0.8); 7.1406 (1.2); 7.1266 (2.5); 7.1138 (1.7); 7.0328 (1.0); 7.0204 (1.8); 7.0068 (1.0); 6.9343 (3.8); 6.9217 (3.5); 6.8892 (2.2); 6.8755 (1.9); 6.7603 (0.6); 6.7494 (2.1); 6.7389 (3.4); 6.7265 (1.6); 6.5226 (1.9); 6.5120 (1.7); 6.4923 (1.0); 6.4809 (3.0); 6.4694 (3.0); 6.4579 (1.0); 6.0875 (0.5); 6.0760 (1.6); 6.0645 (1.6); 6.0530 (0.5); 5.9301 (0.5); 5.9185 (1.6); 5.9069 (1.7); 5.8954 (0.6); 5.4713 (9.0); 3.9297 (1.0); 3.9194 (1.0); 3.9058 (1.2); 3.8956 (1.2); 3.8425 (0.8); 3.8324 (0.8); 3.8190 (1.3); 3.8088 (1.3); 3.7479 (1.4); 3.7358 (1.4); 3.7244 (0.8); 3.7123 (0.9); 3.7019 (1.3); 3.6898 (1.3); 3.6780 (1.0); 3.6660 (1.0); 2.9155 (1.6); 2.9033 (1.7); 2.8895 (3.2); 2.8773 (3.2); 2.8384 (2.8); 2.8292 (2.9); 2.8121 (1.7); 2.8032 (1.6); 2.7827 (1.9); 2.7717 (1.9); 2.7562 (1.8); 2.7457 (1.9); 2.7303 (0.6); 2.7197 (0.7); 2.2968 (182.4); 2.0966 (0.8); 2.0709 (1.0); 1.9843 (4.8); 1.9682 (60.9); 1.9642 (117.6); 1.9601 (167.8); 1.9560 (118.8); 1.9519 (60.9); 1.8447 (8.7); 1.8330 (7.8); 1.7871 (14.1); 1.7755 (14.2); 1.7669 (7.0); 1.7552 (6.8); 1.6991 (6.5); 1.6875 (6.4); 1.5127 (0.4); 1.5012 (0.6); 1.2560 (0.7); 1.2441 (0.8); 1.1175 (0.7); 0.5783 (0.7); 0.5642 (1.6); 0.5561 (2.0); 0.5480 (2.1); 0.5412 (1.8); 0.5339 (1.7); 0.5265 (1.3); 0.5196 (1.2); 0.5123 (1.0); 0.4972 (0.9); 0.4885 (1.0); 0.4821 (1.5); 0.4747 (1.8); 0.4672 (1.8); 0.4593 (1.2); 0.4058 (1.1); 0.3863 (1.5); 0.3782 (1.4); 0.3716 (0.9); 0.3191 (0.9); 0.3125 (1.1); 0.3039 (1.0); 0.2954 (1.1); 0.2870 (1.6); 0.2747 (2.4); 0.2661 (2.4); 0.2446 (0.7); 0.2252 (0.5); 0.2028 (1.1); 0.1951 (0.8); 0.1437 (0.5); 0.1284 (1.5); 0.1207 (2.0); 0.1130 (1.6); 0.0932 (1.1); 0.0844 (1.6); 0.0773 (1.8); 0.0709 (2.0); 0.0632 (1.4); 0.0480 (0.5); -0.1926 (0.8); -0.2006 (1.2); -0.2086 (1.2); -0.2166 (0.9); -0.3634 (0.6); -0.3716 (1.5); -0.3792 (2.1); -0.3874 (2.3); -0.3954 (1.7); -0.4039 (0.7); -0.4177 (1.0); -0.4255 (1.2); -0.4336 (1.2); -0.4417 (0.8); -0.5275 (0.7); -0.5356 (1.7); -0.5437 (2.2); -0.5517 (2.0); -0.5594 (1.4) | 383.2 | |
I-014 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 9.1747 (0.3); 9.0532 (0.4); 8.9085 (12.1); 8.8997 (14.4); 8.8902 (5.4); 8.6453 (0.9); 8.6251 (7.9); 8.6170 (6.9); 8.6048 (5.2); 8.5968 (4.5); 8.3583 (0.4); 8.0886 (9.7); 8.0758 (5.6); 8.0304 (6.3); 8.0121 (4.4); 7.9452 (0.8); 7.6020 (0.4); 7.5665 (0.6); 7.5359 (4.0); 7.5278 (6.4); 7.5201 (4.0); 7.5152 (3.5); 7.5073 (1.7); 7.4706 (0.9); 7.4589 (1.2); 7.4297 (6.4); 7.4156 (8.8); 7.4077 (6.3); 7.3929 (2.2); 7.3812 (1.2); 7.3669 (2.9); 7.3523 (4.4); 7.3475 (3.6); 7.3381 (8.6); 7.3238 (1.2); 7.2201 (3.8); 7.1252 (1.6); 7.1108 (1.6); 7.0628 (2.4); 7.0483 (1.9); 6.9813 (6.3); 6.8770 (2.8); 6.8627 (2.4); 6.7724 (0.7); 6.7609 (2.1); 6.7493 (1.9); 6.7373 (0.4); 6.6719 (3.9); 6.4326 (1.2); 6.4213 (3.2); 6.4098 (2.9); 6.3981 (0.6); 6.1015 (0.7); 6.0899 (1.9); 6.0785 (1.8); 6.0668 (0.4); 6.0001 (0.8); 5.9884 (2.4); 5.9771 (2.2); 5.9654 (0.5); 5.4730 (3.7); 5.2414 (0.4); 5.2298 (0.3); 3.8847 (1.4); 3.8743 (1.4); 3.8610 (2.1); 3.8503 (2.9); 3.8398 (1.0); 3.8262 (1.6); 3.8160 (1.5); 3.7560 (3.6); 3.7439 (3.6); 3.7323 (2.3); 3.7203 (2.2); 3.1342 (0.4); 3.0493 (0.4); 3.0310 (1.2); 2.9835 (2.0); 2.9715 (2.0); 2.9574 (2.9); 2.9455 (2.8); 2.8317 (2.8); 2.8226 (2.9); 2.8045 (5.5); 2.8000 (5.3); 2.7957 (4.6); 2.7790 (0.3); 2.7684 (0.4); 2.7272 (0.5); 2.2962 (181.6); 2.0772 (0.9); 2.0706 (1.2); 1.9855 (2.1); 1.9621 (240.1); 1.9614 (238.2); 1.9269 (1.4); 1.8949 (0.5); 1.8447 (1.6); 1.8303 (9.1); 1.8186 (9.2); 1.7889 (15.4); 1.7842 (12.2); 1.7776 (16.0); 1.7730 (11.5); 1.7236 (7.4); 1.7121 (7.6); 1.6500 (0.5); 1.6378 (0.5); 1.5082 (0.4); 1.4959 (0.4); 1.3843 (1.5); 1.3731 (1.4); 1.2614 (1.5); 1.2529 (1.1); 1.2416 (1.2); 1.2305 (0.9); 1.2203 (0.3); 1.1922 (1.1); 1.1812 (1.1); 1.1517 (0.6); 1.1412 (0.8); 1.1309 (0.6); 0.7992 (0.4); 0.5722 (0.5); 0.5650 (1.2); 0.5577 (1.6); 0.5507 (1.7); 0.5429 (1.9); 0.5351 (1.9); 0.5287 (1.8); 0.5199 (1.9); 0.5129 (1.4); 0.5049 (1.1); 0.4970 (1.1); 0.4883 (0.9); 0.4857 (0.9); 0.4789 (1.1); 0.4706 (1.3); 0.4629 (0.8); 0.4088 (1.0); 0.4014 (1.6); 0.3937 (1.7); 0.3871 (1.5); 0.3803 (0.8); 0.3534 (1.8); 0.3476 (1.9); 0.3410 (2.1); 0.3319 (1.3); 0.1677 (3.1); 0.1546 (2.4); 0.0969 (3.9); -0.0001 (1442.4); -0.0846 (6.1); -0.1002 (12.9); -0.1673 (3.1); -0.1759 (3.7); -0.1839 (4.1); -0.1920 (4.1); -0.1998 (3.7); -0.2076 (2.9); -0.2181 (2.4); -0.2262 (2.6); -0.2346 (2.6); -0.2423 (2.5); -0.2493 (2.3); -0.3160 (1.6); -0.3250 (1.6); -0.3355 (2.8); -0.3441 (3.5); -0.3517 (3.5); -0.3590 (3.5); -0.3658 (2.3); -0.4207 (1.5); -0.4297 (2.8); -0.4374 (4.5); -0.4449 (4.7); -0.4529 (4.6); -0.4612 (3.3); -0.5414 (1.1); -0.5530 (1.0); -0.6287 (0.9); -0.6476 (0.9); -0.6545 (0.8); -0.6638 (0.8); -0.6729 (0.8); -0.6894 (0.8); -0.6993 (0.8); -0.7397 (0.8); -0.7964 (0.7); -0.8304 (0.7); -0.8391 (0.6); -0.8801 (0.6); -0.8904 (0.6); -0.8992 (0.6); -0.9293 (0.6); -0.9403 (0.6); -0.9439 (0.6); -0.9494 (0.6); -0.9705 (0.6); -0.9857 (0.6); -1.0010 (0.5); -1.0205 (0.5); -1.0447 (0.5); -1.0512 (0.5); -1.0744 (0.5); -1.0958 (0.5); -1.1334 (0.5); -1.2053 (0.4); -1.2109 (0.4); -1.2264 (0.4); -1.2555 (0.4); -1.2604 (0.4); -1.2733 (0.4); -1.2883 (0.4); -1.3039 (0.4); -1.3260 (0.4); -1.3466 (0.4); -1.3590 (0.4); -1.3772 (0.4); -1.4025 (0.4); -1.4265 (0.3); -1.4391 (0.3); -1.4498 (0.3); -1.4562 (0.3); -1.4632 (0.3); -1.4780 (0.3) | 417.2 | |
I-015 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.9069 (4.4); 8.8986 (12.1); 8.8906 (8.2); 8.6411 (5.2); 8.6330 (5.2); 8.6101 (5.5); 8.6021 (5.6); 8.0852 (7.3); 8.0204 (7.9); 7.9431 (0.9); 7.5353 (3.3); 7.5293 (3.9); 7.5213 (7.9); 7.5060 (3.4); 7.4999 (4.3); 7.4860 (4.1); 7.4385 (1.4); 7.4305 (2.7); 7.4225 (1.4); 7.4157 (1.6); 7.4077 (3.0); 7.3997 (1.5); 7.3159 (3.2); 7.3021 (2.7); 7.1302 (2.2); 7.1162 (2.1); 6.9476 (2.6); 6.9339 (2.8); 6.9261 (4.1); 6.9122 (3.9); 6.7829 (0.5); 6.7715 (1.4); 6.7598 (1.4); 6.7484 (0.5); 6.4923 (2.7); 6.4786 (2.6); 6.4418 (0.8); 6.4305 (2.4); 6.4190 (2.4); 6.4075 (0.8); 6.1560 (0.6); 6.1447 (1.9); 6.1331 (2.0); 6.1218 (0.6); 5.9185 (0.5); 5.9072 (1.7); 5.8956 (1.7); 5.8840 (0.6); 5.4723 (4.8); 5.2388 (0.4); 5.2272 (0.4); 3.8922 (1.0); 3.8816 (1.0); 3.8681 (1.4); 3.8580 (1.6); 3.8522 (1.0); 3.8386 (1.7); 3.8283 (1.7); 3.7821 (1.7); 3.7700 (1.8); 3.7534 (1.5); 3.7416 (1.5); 3.7293 (1.0); 3.7174 (1.0); 3.1854 (0.3); 3.0327 (1.0); 2.9483 (1.3); 2.9363 (1.3); 2.9222 (2.3); 2.9102 (2.3); 2.8525 (2.2); 2.8434 (2.2); 2.8268 (1.8); 2.8171 (1.9); 2.8017 (1.4); 2.7898 (2.2); 2.7560 (1.3); 2.7454 (1.4); 2.7295 (0.7); 2.7194 (0.8); 2.6929 (0.7); 2.2961 (162.5); 2.2802 (0.9); 2.2693 (0.6); 2.0976 (1.0); 2.0854 (0.8); 2.0751 (1.0); 2.0649 (0.8); 2.0206 (0.3); 2.0108 (0.4); 1.9851 (1.0); 1.9618 (141.4); 1.9603 (138.5); 1.8447 (1.0); 1.8350 (6.1); 1.8232 (6.0); 1.7856 (16.0); 1.7741 (15.8); 1.7263 (7.4); 1.7147 (7.4); 1.3832 (1.6); 1.3719 (1.6); 1.2604 (2.9); 1.2453 (1.0); 1.2352 (0.5); 1.1913 (1.9); 1.1804 (2.2); 1.1696 (0.8); 1.1594 (0.4); 0.8925 (0.4); 0.8818 (0.8); 0.8701 (0.4); 0.5972 (0.6); 0.5892 (1.0); 0.5823 (1.6); 0.5750 (1.9); 0.5679 (2.1); 0.5603 (2.0); 0.5530 (2.5); 0.5387 (1.7); 0.5358 (1.7); 0.5326 (1.8); 0.5141 (1.7); 0.5085 (1.4); 0.4998 (1.6); 0.4926 (1.6); 0.4846 (1.2); 0.4771 (0.4); 0.4179 (1.6); 0.4093 (1.9); 0.3974 (3.3); 0.3711 (0.6); 0.3596 (0.5); 0.3509 (0.4); 0.3438 (0.4); 0.2896 (1.1); 0.2802 (1.7); 0.2679 (1.9); 0.2586 (1.4); 0.2481 (1.0); 0.2428 (1.0); 0.2342 (1.1); 0.2264 (1.2); 0.2183 (1.0); 0.2114 (0.8); 0.2036 (0.6); 0.1594 (0.4); 0.1507 (0.6); 0.1441 (1.1); 0.1357 (1.6); 0.1294 (1.5); 0.1209 (1.8); 0.1134 (1.9); 0.1049 (1.6); 0.0970 (9.4); 0.0784 (0.9); 0.0461 (0.7); 0.0375 (0.8); -0.0001 (1384.6); -0.0277 (1.2); -0.0345 (1.1); -0.0422 (1.0); -0.0507 (1.1); -0.0571 (0.9); -0.0655 (1.0); -0.0844 (0.9); -0.1000 (8.2); -0.1669 (0.4); -0.1747 (0.8); -0.1826 (1.0); -0.1904 (1.1); -0.1983 (0.8); -0.2065 (0.4); -0.2281 (0.4); -0.2361 (0.6); -0.2440 (0.5); -0.2515 (0.4); -0.3189 (0.5); -0.3267 (1.2); -0.3340 (1.8); -0.3419 (1.9); -0.3502 (1.5); -0.3584 (0.6); -0.3746 (0.3); -0.3829 (0.8); -0.3909 (1.1); -0.3987 (1.0); -0.4069 (0.7); -0.4630 (0.6); -0.4709 (1.4); -0.4791 (1.8); -0.4868 (1.6); -0.4942 (1.1); -0.5016 (0.4) | 453.0 | |
I-016 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.9118 (7.5); 8.9047 (16.0); 8.8968 (13.6); 8.6157 (7.1); 8.6076 (7.2); 8.5720 (8.4); 8.5639 (8.5); 8.0839 (11.5); 8.0785 (6.2); 8.0249 (6.5); 8.0126 (5.6); 7.5629 (3.4); 7.5606 (3.5); 7.5495 (3.9); 7.5471 (3.8); 7.5441 (2.0); 7.5417 (2.0); 7.5387 (2.2); 7.5341 (3.9); 7.5306 (6.2); 7.5279 (3.1); 7.5261 (7.4); 7.5226 (2.2); 7.5180 (3.6); 7.3879 (2.3); 7.3838 (2.1); 7.3798 (4.6); 7.3757 (3.9); 7.3717 (2.4); 7.3676 (2.0); 7.3534 (0.6); 7.3505 (0.6); 7.3441 (0.4); 7.3401 (0.5); 7.3371 (1.0); 7.3323 (2.6); 7.3265 (5.8); 7.3215 (7.2); 7.3191 (8.6); 7.3127 (2.4); 7.3084 (0.9); 7.3048 (5.0); 7.2916 (5.9); 7.2785 (3.4); 7.1801 (1.9); 7.1777 (1.9); 7.1667 (2.0); 7.1643 (2.0); 7.1039 (1.9); 7.1015 (1.9); 7.0911 (1.7); 7.0888 (1.7); 6.9167 (3.5); 6.9143 (3.6); 6.9040 (3.4); 6.9016 (3.3); 6.7718 (0.5); 6.7601 (1.7); 6.7564 (2.0); 6.7484 (1.7); 6.7435 (3.3); 6.7368 (0.5); 6.7304 (1.9); 6.4872 (2.0); 6.4848 (2.0); 6.4746 (1.9); 6.4722 (1.8); 6.4596 (0.8); 6.4481 (2.5); 6.4366 (2.5); 6.4251 (0.8); 6.1523 (0.6); 6.1407 (2.0); 6.1292 (2.0); 6.1176 (0.6); 5.9033 (0.5); 5.8917 (1.7); 5.8801 (1.7); 5.8684 (0.5); 5.4725 (1.4); 3.9193 (1.0); 3.9088 (1.0); 3.8954 (1.3); 3.8849 (1.3); 3.8490 (1.0); 3.8388 (1.0); 3.8255 (1.7); 3.8152 (1.7); 3.7699 (1.9); 3.7577 (1.9); 3.7463 (1.1); 3.7341 (1.1); 3.7276 (1.4); 3.7156 (1.4); 3.7037 (1.1); 3.6918 (1.1); 2.9273 (1.6); 2.9151 (1.6); 2.9012 (3.0); 2.8890 (3.0); 2.8501 (2.5); 2.8409 (2.5); 2.8309 (0.9); 2.8239 (1.4); 2.8201 (1.0); 2.8148 (1.3); 2.8048 (1.5); 2.7940 (1.5); 2.7482 (1.5); 2.7376 (1.5); 2.7221 (0.8); 2.7115 (0.8); 2.2927 (45.4); 2.0763 (0.5); 2.0722 (0.8); 2.0681 (0.5); 1.9855 (0.4); 1.9774 (1.5); 1.9696 (45.7); 1.9654 (89.0); 1.9613 (130.4); 1.9572 (89.2); 1.9531 (44.9); 1.9487 (1.2); 1.9444 (0.4); 1.8503 (0.6); 1.8462 (1.0); 1.8413 (8.2); 1.8295 (7.9); 1.7935 (13.9); 1.7820 (13.8); 1.7672 (7.1); 1.7556 (7.1); 1.7079 (8.5); 1.6963 (8.5); 1.2671 (0.5); 1.2641 (0.4); 1.2620 (0.4); 1.2561 (0.7); 1.2474 (0.4); 1.2448 (0.5); 1.1941 (0.6); 1.1831 (0.6); 1.1444 (0.6); 1.1404 (0.4); 1.1340 (0.7); 1.1323 (0.7); 1.1264 (0.4); 1.1221 (0.6); 0.5931 (0.5); 0.5870 (0.6); 0.5839 (0.7); 0.5792 (1.5); 0.5735 (1.2); 0.5709 (1.1); 0.5651 (1.6); 0.5594 (0.8); 0.5575 (0.8); 0.5509 (0.8); 0.5470 (0.6); 0.5445 (0.7); 0.5385 (1.0); 0.5362 (0.9); 0.5317 (1.2); 0.5233 (1.5); 0.5191 (1.0); 0.5158 (0.9); 0.5093 (1.7); 0.5021 (1.3); 0.5008 (1.3); 0.4944 (1.7); 0.4870 (1.8); 0.4802 (1.6); 0.4719 (0.6); 0.4651 (0.4); 0.4228 (0.5); 0.4145 (0.9); 0.4087 (0.9); 0.4057 (1.0); 0.4021 (1.1); 0.3954 (1.4); 0.3870 (1.5); 0.3808 (1.0); 0.3725 (0.5); 0.3431 (0.5); 0.3345 (1.0); 0.3283 (1.2); 0.3196 (1.0); 0.3128 (0.6); 0.3041 (0.3); 0.2986 (0.4); 0.2925 (0.6); 0.2903 (0.5); 0.2853 (1.3); 0.2821 (0.9); 0.2769 (1.8); 0.2721 (1.4); 0.2695 (1.5); 0.2637 (1.6); 0.2606 (1.2); 0.2561 (1.0); 0.2509 (0.6); 0.2471 (0.7); 0.2359 (0.5); 0.2285 (0.6); 0.2268 (0.6); 0.2222 (0.6); 0.2196 (0.6); 0.2134 (0.9); 0.2058 (0.6); 0.2000 (0.3); 0.1982 (0.3); 0.1533 (0.4); 0.1458 (0.5); 0.1441 (0.6); 0.1380 (1.2); 0.1307 (1.5); 0.1240 (1.2); 0.1223 (1.2); 0.1173 (0.9); 0.1154 (0.9); 0.1075 (1.5); 0.1001 (1.2); 0.0981 (1.3); 0.0936 (1.2); 0.0913 (1.4); 0.0849 (1.6); 0.0775 (1.2); 0.0715 (0.6); 0.0696 (0.5); 0.0622 (0.5); 0.0054 (4.2); -0.0001 (138.3); -0.0057 (4.0); -0.1002 (0.6); -0.2120 (0.7); -0.2200 (1.0); -0.2283 (1.1); -0.2358 (0.8); -0.2442 (0.4); -0.3370 (0.6); -0.3453 (1.2); -0.3524 (1.9); -0.3608 (1.9); -0.3689 (1.4); -0.3772 (0.7); -0.3850 (0.4); -0.3933 (0.8); -0.4009 (1.0); -0.4093 (1.0); -0.4173 (0.6); -0.4948 (0.6); -0.5029 (1.3); -0.5111 (1.8); -0.5192 (1.6); -0.5264 (1.1); -0.5347 (0.4) | 417.1 | |
I-017 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.8963 (14.2); 8.8937 (9.4); 8.8882 (14.6); 8.8856 (9.4); 8.6457 (10.4); 8.6376 (10.7); 8.6170 (8.9); 8.6090 (9.1); 8.0833 (11.8); 8.0744 (6.4); 8.0179 (8.4); 8.0133 (7.2); 7.5340 (6.4); 7.5308 (6.9); 7.5277 (4.3); 7.5195 (7.4); 7.5114 (4.2); 7.5093 (4.6); 7.5011 (2.0); 7.4512 (2.6); 7.4473 (3.6); 7.4433 (7.5); 7.4351 (2.5); 7.4314 (3.0); 7.4233 (5.6); 7.4152 (2.9); 7.4106 (5.1); 7.4073 (5.2); 7.3976 (0.4); 7.3765 (1.9); 7.3733 (1.8); 7.3628 (2.2); 7.3595 (2.1); 7.3426 (3.6); 7.3393 (3.7); 7.3317 (11.6); 7.3256 (4.1); 7.1689 (3.5); 7.1551 (3.1); 6.9598 (6.6); 6.9459 (9.2); 6.7822 (0.6); 6.7706 (1.9); 6.7651 (2.9); 6.7618 (3.2); 6.7592 (2.2); 6.7515 (3.1); 6.7482 (3.6); 6.5381 (5.3); 6.5244 (4.7); 6.4641 (0.9); 6.4526 (3.1); 6.4411 (3.1); 6.4296 (1.0); 6.0843 (0.7); 6.0728 (2.2); 6.0612 (2.3); 6.0496 (0.7); 5.9413 (0.8); 5.9297 (2.6); 5.9180 (2.6); 5.9064 (0.8); 5.4724 (6.3); 3.8983 (1.5); 3.8879 (1.6); 3.8745 (2.1); 3.8641 (2.1); 3.8524 (1.1); 3.8422 (1.2); 3.8289 (1.9); 3.8185 (1.9); 3.7612 (2.0); 3.7491 (2.0); 3.7376 (1.3); 3.7330 (2.2); 3.7255 (1.4); 3.7210 (2.3); 3.7092 (1.7); 3.6971 (1.7); 2.9332 (1.9); 2.9210 (1.9); 2.9071 (3.2); 2.8949 (3.2); 2.8378 (2.8); 2.8286 (2.9); 2.8163 (0.9); 2.8118 (1.8); 2.8027 (1.8); 2.7904 (2.0); 2.7794 (2.0); 2.7604 (1.9); 2.7499 (1.9); 2.7344 (0.7); 2.7239 (0.7); 2.2918 (51.8); 2.0803 (0.4); 2.0762 (0.7); 2.0721 (1.1); 2.0680 (0.7); 2.0639 (0.4); 1.9855 (3.4); 1.9813 (0.3); 1.9773 (1.8); 1.9695 (64.1); 1.9654 (125.8); 1.9613 (185.1); 1.9571 (127.6); 1.9530 (64.8); 1.9443 (1.1); 1.9404 (0.5); 1.9356 (0.3); 1.8544 (0.4); 1.8503 (0.7); 1.8462 (1.1); 1.8421 (0.9); 1.8379 (0.5); 1.8292 (8.5); 1.8175 (8.5); 1.7841 (11.4); 1.7778 (16.0); 1.7725 (12.3); 1.7663 (15.6); 1.7201 (9.3); 1.7085 (9.3); 1.3193 (0.3); 1.3083 (0.4); 1.3022 (0.4); 1.2913 (0.4); 1.2648 (0.5); 1.2565 (0.9); 1.2447 (1.0); 1.2339 (0.8); 1.2252 (0.4); 1.2206 (0.3); 1.1894 (0.8); 1.1851 (0.4); 1.1782 (1.2); 1.1649 (0.9); 1.1585 (0.6); 1.1543 (0.7); 0.5887 (0.4); 0.5831 (1.0); 0.5766 (1.1); 0.5739 (1.1); 0.5690 (1.8); 0.5646 (1.7); 0.5598 (2.0); 0.5556 (1.7); 0.5511 (2.4); 0.5437 (2.5); 0.5367 (2.6); 0.5306 (1.6); 0.5278 (1.6); 0.5229 (2.5); 0.5175 (1.5); 0.5126 (1.4); 0.5095 (1.5); 0.5034 (1.5); 0.4964 (1.3); 0.4909 (1.1); 0.4882 (1.5); 0.4822 (1.9); 0.4735 (1.7); 0.4667 (1.3); 0.4580 (0.6); 0.4182 (0.7); 0.4097 (1.6); 0.4035 (1.6); 0.4017 (1.6); 0.3976 (1.4); 0.3938 (2.0); 0.3897 (2.0); 0.3848 (2.2); 0.3808 (1.8); 0.3779 (1.7); 0.3726 (1.4); 0.3694 (1.0); 0.3645 (0.8); 0.3566 (0.5); 0.3082 (0.4); 0.3004 (0.8); 0.2945 (1.5); 0.2914 (1.3); 0.2861 (2.2); 0.2828 (1.8); 0.2780 (2.1); 0.2730 (1.9); 0.2698 (1.6); 0.2649 (1.2); 0.2556 (0.6); 0.2342 (0.7); 0.2250 (0.8); 0.2174 (0.8); 0.2112 (1.1); 0.2034 (0.8); 0.1975 (0.4); 0.1614 (0.5); 0.1526 (0.7); 0.1465 (1.4); 0.1387 (1.9); 0.1315 (1.9); 0.1235 (2.4); 0.1170 (2.4); 0.1084 (1.8); 0.1019 (1.9); 0.0947 (1.5); 0.0867 (0.6); 0.0793 (0.5); 0.0054 (5.8); -0.0001 (189.6); -0.0057 (5.9); -0.1002 (0.8); -0.1724 (0.4); -0.1806 (0.8); -0.1886 (1.2); -0.1968 (1.3); -0.2047 (0.9); -0.2130 (0.4); -0.3337 (0.6); -0.3417 (1.5); -0.3484 (2.2); -0.3567 (2.4); -0.3648 (1.7); -0.3731 (0.8); -0.4086 (0.4); -0.4170 (1.0); -0.4250 (1.2); -0.4330 (1.2); -0.4412 (0.8); -0.4495 (0.4); -0.4889 (0.7); -0.4970 (1.7); -0.5052 (2.2); -0.5132 (2.0); -0.5200 (1.3); -0.5280 (0.5) | 417.1 | |
I-018 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9632 (13.2); 8.9511 (13.5); 8.7285 (6.0); 8.7163 (6.1); 8.2657 (12.3); 8.2409 (5.0); 7.6591 (3.7); 7.6470 (7.2); 7.6348 (3.6); 7.5636 (1.6); 7.5514 (3.1); 7.5392 (1.6); 7.5326 (0.7); 7.5155 (1.4); 7.5114 (1.5); 7.4945 (2.7); 7.4775 (1.6); 7.4734 (1.6); 7.4566 (0.7); 7.3410 (0.6); 7.3369 (0.7); 7.3201 (1.2); 7.3030 (0.7); 7.2990 (0.7); 7.2823 (0.4); 7.1775 (2.7); 7.1558 (4.9); 7.1343 (2.4); 7.1184 (2.1); 7.0968 (3.8); 7.0753 (1.8); 6.7138 (0.9); 6.6923 (1.6); 6.6708 (0.8); 6.6206 (0.9); 6.6033 (3.4); 6.5859 (3.4); 6.5686 (0.9); 6.0424 (0.4); 6.0253 (1.2); 6.0080 (1.2); 5.9912 (0.3); 5.7579 (16.0); 3.7734 (0.5); 3.7573 (0.5); 3.7377 (1.3); 3.7217 (1.3); 3.7039 (1.4); 3.6864 (1.4); 3.6679 (0.5); 3.6505 (0.5); 3.3289 (85.5); 2.9222 (1.4); 2.9055 (1.5); 2.8830 (2.3); 2.8663 (2.3); 2.7669 (2.2); 2.7521 (2.2); 2.7277 (1.4); 2.7128 (1.4); 2.6766 (0.7); 2.6722 (0.9); 2.6677 (0.7); 2.5254 (3.2); 2.5118 (57.1); 2.5077 (111.3); 2.5032 (144.5); 2.4988 (106.4); 2.4946 (53.5); 2.3343 (0.6); 2.3300 (0.9); 2.3256 (0.6); 2.0759 (6.4); 1.7456 (13.4); 1.7282 (13.3); 1.7017 (5.3); 1.6844 (5.2); 1.0644 (0.4); 1.0469 (0.6); 1.0305 (0.4); 0.4921 (0.5); 0.4840 (0.6); 0.4795 (0.6); 0.4723 (1.0); 0.4664 (0.8); 0.4592 (1.0); 0.4523 (0.7); 0.4477 (0.9); 0.4366 (0.8); 0.4275 (0.6); 0.3518 (0.7); 0.3399 (1.3); 0.3277 (1.9); 0.3159 (1.8); 0.3093 (1.7); 0.2975 (0.9); 0.2799 (0.6); 0.2732 (0.6); 0.2683 (0.8); 0.2613 (0.9); 0.2493 (0.6); 0.2375 (0.4); 0.2248 (0.3); 0.2114 (0.5); 0.1882 (1.4); 0.1749 (4.2); 0.1544 (4.6); 0.1413 (1.1); 0.1182 (0.4); 0.0079 (3.8); -0.0001 (93.5); -0.0082 (3.6); -0.1494 (0.5); -0.2935 (0.6); -0.3048 (1.3); -0.3135 (1.4); -0.3254 (2.0); -0.3373 (1.4); -0.3406 (1.4); -0.4767 (1.5); -0.4798 (1.5); -0.4918 (1.9); -0.5032 (1.3); -0.5123 (1.2); -0.5243 (0.5) | 385.2 | |
I-019 | 1H-NMR(600.1 MHz, CD 3CN, 260 K): δ= 8.9092 (0.4); 8.9011 (0.5); 8.8719 (13.4); 8.8638 (13.1); 8.6337 (3.0); 8.6257 (2.9); 8.2626 (0.3); 8.1801 (0.4); 8.1463 (6.7); 8.0919 (11.9); 8.0774 (0.4); 8.0401 (4.4); 8.0268 (0.4); 7.8451 (1.9); 7.7364 (1.9); 7.6992 (7.2); 7.5945 (7.2); 7.5198 (3.7); 7.5117 (6.9); 7.5037 (3.5); 7.4297 (0.9); 7.4218 (1.6); 7.4140 (0.8); 6.3800 (1.3); 6.3685 (3.9); 6.3568 (3.9); 6.3453 (1.2); 6.0315 (0.4); 6.0195 (1.0); 6.0082 (1.0); 5.9967 (0.3); 5.4721 (10.5); 3.6955 (0.6); 3.6852 (0.6); 3.6719 (0.8); 3.6613 (0.8); 3.5385 (0.8); 3.5270 (0.8); 3.5148 (0.6); 3.5033 (0.6); 3.2206 (0.3); 2.9096 (1.0); 2.8983 (1.1); 2.8834 (4.3); 2.8713 (6.3); 2.8597 (4.2); 2.8430 (1.0); 2.8334 (0.9); 2.6637 (1.4); 2.3187 (0.5); 2.2901 (183.1); 2.0925 (0.4); 2.0800 (0.8); 2.0760 (1.4); 2.0719 (2.0); 2.0677 (1.4); 2.0637 (0.8); 2.0422 (0.4); 2.0379 (0.4); 2.0324 (0.4); 2.0233 (0.5); 2.0188 (0.5); 2.0151 (0.5); 2.0112 (0.6); 1.9994 (0.9); 1.9768 (7.1); 1.9692 (124.0); 1.9651 (233.3); 1.9610 (332.5); 1.9569 (225.5); 1.9528 (111.7); 1.9441 (0.9); 1.8540 (0.7); 1.8500 (1.4); 1.8459 (2.0); 1.8418 (1.5); 1.8376 (0.9); 1.8217 (16.0); 1.8100 (15.9); 1.7943 (0.6); 1.7823 (0.5); 1.7497 (0.4); 1.7303 (4.0); 1.7188 (3.8); 1.4157 (0.4); 1.3409 (0.6); 1.3050 (0.6); 1.2828 (1.1); 1.2749 (0.7); 1.2609 (2.5); 1.2441 (0.3); 1.2066 (0.4); 1.0616 (0.4); 1.0509 (0.7); 1.0410 (0.8); 1.0294 (0.6); 0.8814 (0.5); 0.5765 (0.6); 0.5642 (1.5); 0.5544 (2.0); 0.5435 (1.6); 0.5349 (0.8); 0.5199 (0.4); 0.5168 (0.4); 0.5061 (0.4); 0.5034 (0.4); 0.4922 (0.6); 0.4785 (1.2); 0.4714 (1.2); 0.4651 (1.2); 0.4587 (0.8); 0.4512 (0.5); 0.3405 (0.6); 0.3314 (0.7); 0.3234 (0.8); 0.3023 (0.8); 0.2933 (1.1); 0.2870 (2.0); 0.2795 (2.6); 0.2725 (2.4); 0.2651 (2.1); 0.2567 (1.9); 0.2513 (2.0); 0.2435 (2.4); 0.2358 (2.4); 0.2293 (2.5); 0.2218 (1.7); 0.2154 (1.0); 0.2063 (0.6); 0.0968 (0.7); 0.0052 (6.4); -0.0001 (147.2); -0.0057 (4.2); -0.1002 (0.7); -0.1976 (0.8); -0.2057 (1.8); -0.2138 (2.6); -0.2219 (2.7); -0.2294 (2.0); -0.2377 (0.8); -0.3728 (0.9); -0.3808 (2.1); -0.3886 (2.8); -0.3966 (2.5); -0.4045 (1.7); -0.4131 (0.6) | 515.0 | |
I-020 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4561 (2.7); 9.4382 (2.8); 8.9983 (15.6); 8.9861 (16.0); 8.3243 (0.3); 8.3166 (0.4); 8.2594 (0.3); 8.2375 (4.0); 8.2337 (7.8); 8.2299 (4.6); 8.1748 (12.9); 8.1443 (2.5); 8.1395 (7.5); 8.1349 (10.0); 8.1305 (7.1); 8.1258 (2.3); 7.6439 (4.2); 7.6318 (8.0); 7.6196 (4.1); 6.0444 (0.5); 6.0272 (2.1); 6.0097 (3.3); 5.9921 (2.1); 5.9746 (0.4); 3.3690 (0.4); 3.3572 (2.2); 3.3299 (113.6); 3.3137 (35.5); 2.6758 (1.1); 2.6714 (1.5); 2.6668 (1.1); 2.6623 (0.5); 2.5248 (4.3); 2.5200 (6.8); 2.5113 (91.1); 2.5069 (184.0); 2.5024 (241.4); 2.4978 (173.5); 2.4933 (83.2); 2.3381 (0.6); 2.3337 (1.1); 2.3292 (1.5); 2.3247 (1.1); 2.0750 (0.4); 1.6537 (12.8); 1.6363 (12.8); 0.1459 (0.9); 0.0080 (7.2); -0.0002 (210.9); -0.0085 (7.4); -0.1496 (0.9) | 407.1 | |
I-021 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 8.8212 (7.5); 8.6613 (6.0); 8.6448 (4.2); 8.3409 (0.4); 8.3294 (0.4); 8.0535 (16.0); 7.4612 (8.2); 7.3588 (4.0); 7.3236 (0.5); 7.0365 (5.3); 6.9590 (4.0); 6.8254 (5.3); 6.6102 (0.3); 6.5985 (0.6); 6.3509 (4.5); 6.3336 (14.8); 6.3162 (14.8); 6.2989 (4.6); 3.3108 (2.1); 3.2991 (2.1); 3.2530 (2.1); 3.2383 (2.2); 3.1303 (1.0); 3.1137 (0.4); 3.0939 (0.3); 3.0780 (0.3); 3.0473 (0.8); 2.9905 (1.1); 2.9400 (5.8); 2.5163 (2.0); 2.3306 (432.9); 2.1330 (0.6); 2.1268 (0.8); 2.1207 (0.6); 2.0019 (0.3); 1.9956 (0.4); 1.9896 (0.4); 1.9837 (0.8); 1.9775 (2.2); 1.9720 (50.3); 1.9659 (100.7); 1.9597 (147.8); 1.9535 (100.1); 1.9474 (50.2); 1.9407 (1.7); 1.9343 (0.8); 1.9282 (0.3); 1.8065 (10.2); 1.7947 (8.1); 1.7883 (8.2); 1.7726 (12.5); 1.7570 (10.4); 1.6513 (1.2); 1.6335 (1.2); 1.1851 (0.6); 1.1686 (0.6); 0.7519 (1.8); 0.5810 (2.2); 0.3130 (7.2); 0.2088 (1.6); 0.1826 (2.1); -0.1001 (3.8) | 389.1 | |
I-022 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 8.8323 (3.2); 8.7611 (1.8); 8.0706 (2.8); 7.4919 (8.4); 7.4798 (15.9); 7.4677 (8.0); 6.3900 (1.8); 3.7285 (0.7); 3.6435 (0.7); 2.9584 (1.6); 2.3767 (1.1); 2.3653 (0.7); 2.3534 (4.8); 2.3265 (638.4); 2.3047 (1.5); 2.2933 (1.2); 2.2832 (0.5); 2.1332 (0.4); 2.1270 (0.5); 2.1208 (0.4); 1.9930 (0.5); 1.9868 (0.8); 1.9843 (0.9); 1.9778 (1.7); 1.9722 (32.7); 1.9660 (65.4); 1.9598 (95.4); 1.9537 (65.6); 1.9475 (32.6); 1.9369 (0.4); 1.8249 (15.9); 1.8080 (16.0); 1.7887 (2.0); 1.7825 (1.1); 1.7763 (0.7); 1.1389 (0.6); 0.7432 (1.0); 0.4967 (1.4); 0.3501 (3.6); -0.0206 (1.1) | 459.0 | |
I-023 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 8.8577 (13.7); 8.8456 (13.9); 8.7878 (8.1); 8.7757 (8.2); 8.0817 (11.5); 8.0145 (6.4); 7.4930 (5.7); 7.4809 (11.1); 7.4688 (5.6); 6.7228 (14.2); 6.5710 (2.9); 6.5260 (0.9); 6.5086 (3.0); 6.4912 (3.0); 6.4737 (0.9); 6.2020 (0.6); 6.1847 (2.0); 6.1673 (2.0); 6.1500 (0.6); 3.8049 (1.0); 3.7891 (1.1); 3.7690 (1.6); 3.7532 (1.6); 3.6471 (1.7); 3.6292 (1.8); 3.6112 (1.2); 3.5933 (1.2); 3.2619 (0.4); 2.9703 (1.3); 2.9525 (1.3); 2.9313 (3.3); 2.9136 (3.3); 2.8856 (3.0); 2.8707 (3.1); 2.8467 (1.2); 2.8317 (1.2); 2.5161 (0.5); 2.3296 (131.9); 2.2984 (0.8); 1.9722 (12.7); 1.9660 (25.3); 1.9599 (37.3); 1.9537 (25.1); 1.9475 (12.7); 1.7837 (15.9); 1.7778 (9.9); 1.7662 (16.0); 1.7604 (9.6); 1.1346 (0.6); 1.1172 (0.8); 1.1010 (0.6); 0.5590 (0.4); 0.5462 (1.2); 0.5397 (1.0); 0.5226 (2.6); 0.5023 (3.0); 0.4848 (1.9); 0.4618 (0.4); 0.3713 (0.5); 0.3593 (2.8); 0.3545 (2.6); 0.3470 (2.6); 0.3424 (2.6); 0.3304 (0.4); 0.3223 (0.5); 0.3093 (0.5); 0.2995 (1.3); 0.2898 (1.8); 0.2865 (1.8); 0.2801 (3.4); 0.2702 (2.2); 0.2656 (1.7); 0.2604 (3.6); 0.2516 (1.6); 0.2415 (1.1); 0.2315 (0.4); 0.2188 (0.4); -0.1090 (0.6); -0.1212 (1.3); -0.1311 (1.3); -0.1441 (1.5); -0.1490 (1.3); -0.1541 (1.1); -0.1630 (0.7) | 423.1 | |
I-024 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.7911 (4.3); 8.7811 (4.3); 8.3108 (0.5); 8.2558 (16.0); 7.6034 (5.8); 7.5912 (11.1); 7.5791 (5.6); 7.4212 (2.2); 6.3944 (1.6); 6.3781 (1.6); 3.3361 (143.3); 3.2048 (0.7); 3.1884 (0.8); 3.1674 (2.9); 3.1502 (3.8); 3.1299 (2.3); 3.1078 (0.7); 3.0927 (0.6); 2.6784 (0.3); 2.6738 (0.5); 2.6693 (0.3); 2.5441 (0.9); 2.5272 (1.2); 2.5138 (28.0); 2.5094 (57.2); 2.5049 (75.5); 2.5003 (54.5); 2.4959 (26.5); 2.3362 (0.3); 2.3317 (0.4); 2.3272 (0.3); 2.0744 (15.4); 1.7808 (9.3); 1.7636 (9.2); 0.6367 (1.2); 0.6226 (1.7); 0.6093 (1.3); 0.5915 (0.6); 0.3038 (1.4); 0.2653 (1.0); 0.2524 (1.4); 0.2419 (1.6); 0.2321 (1.7); 0.2207 (1.3); 0.1986 (0.5); 0.1103 (0.9); 0.0977 (1.8); 0.0866 (2.7); 0.0739 (2.9); 0.0638 (2.0); 0.0509 (0.8); -0.0002 (1.3); -0.1997 (0.7); -0.2119 (1.8); -0.2226 (2.4); -0.2347 (2.3); -0.2464 (1.5); -0.2589 (0.6) | 423.1 | |
I-025 | 1H-NMR(400.6 MHz, CD 3CN, 260 K): δ= 8.7649 (3.5); 8.7528 (3.6); 8.5659 (9.9); 8.5538 (10.1); 8.0266 (8.9); 8.0214 (3.7); 7.4084 (1.0); 7.3963 (1.8); 7.3842 (1.0); 7.3737 (2.7); 7.3616 (5.1); 7.3495 (2.5); 7.0865 (5.7); 7.0851 (5.7); 6.8358 (2.2); 6.8346 (2.1); 6.7657 (0.7); 6.7487 (2.5); 6.7317 (2.5); 6.7147 (0.7); 6.3042 (0.9); 6.2868 (0.9); 3.9189 (15.6); 3.9174 (16.0); 3.8648 (6.2); 3.8634 (6.2); 3.2377 (1.5); 3.2354 (1.5); 3.2199 (2.0); 3.0822 (5.5); 3.0657 (5.3); 2.3392 (0.4); 2.2999 (115.2); 2.2712 (1.3); 1.9478 (0.4); 1.9421 (12.7); 1.9359 (25.2); 1.9298 (37.0); 1.9236 (25.4); 1.9175 (12.6); 1.9109 (0.4); 1.8616 (11.5); 1.8446 (11.5); 1.7584 (0.4); 1.7500 (4.3); 1.7325 (4.3); 0.6425 (0.4); 0.5598 (0.6); 0.5559 (0.6); 0.5519 (0.6); 0.5476 (0.5); 0.5432 (0.6); 0.5395 (1.1); 0.5358 (0.7); 0.5316 (0.6); 0.5270 (0.7); 0.5231 (0.7); 0.5193 (0.7); 0.5069 (0.4); 0.2445 (0.4); 0.2363 (0.5); 0.2307 (1.1); 0.2251 (0.6); 0.2166 (1.0); 0.2104 (1.4); 0.1950 (1.2); 0.1865 (1.2); 0.1815 (1.1); 0.1747 (1.9); 0.1712 (1.4); 0.1647 (1.4); 0.1606 (1.9); 0.1540 (1.4); 0.1512 (2.1); 0.1441 (0.9); 0.1406 (1.2); 0.1309 (1.0); 0.1182 (0.4); 0.1092 (0.5); 0.0897 (0.7); 0.0810 (0.6); 0.0769 (1.1); 0.0684 (1.0); 0.0642 (1.0); 0.0577 (0.8); 0.0528 (1.0); 0.0459 (0.8); 0.0413 (0.6); 0.0350 (0.4); -0.0549 (0.4); -0.0630 (0.4); -0.0745 (0.5); -0.0781 (0.5); -0.0866 (0.4); -0.0906 (0.4) | 421.15 | |
I-026 | 1H-NMR(400.6 MHz, CD 3CN, 260 K): δ= 8.8789 (4.8); 8.8668 (5.0); 8.7786 (6.5); 8.7665 (6.7); 8.6796 (3.1); 8.6674 (3.2); 8.0872 (6.5); 8.0769 (5.1); 7.9984 (1.5); 7.5007 (1.3); 7.4886 (2.5); 7.4765 (1.3); 7.4298 (2.0); 7.4177 (3.8); 7.4056 (2.2); 6.7405 (0.6); 6.7230 (1.9); 6.7054 (2.0); 6.6878 (0.6); 6.4072 (0.4); 6.3900 (1.4); 6.3727 (1.5); 6.3556 (0.5); 6.1994 (0.9); 6.1821 (0.9); 4.0705 (0.4); 3.8950 (0.6); 3.8506 (16.0); 3.7210 (12.1); 3.6921 (0.3); 3.3565 (0.9); 3.3427 (0.9); 3.3177 (1.1); 3.3037 (1.2); 3.2594 (1.0); 2.9622 (1.1); 2.9450 (2.0); 2.9347 (1.2); 2.9233 (1.0); 2.9060 (2.3); 2.8952 (1.6); 2.7463 (1.5); 2.7257 (1.6); 2.7071 (1.1); 2.6864 (1.1); 2.3434 (0.4); 2.3346 (0.5); 2.3305 (0.6); 2.2937 (256.4); 2.2652 (2.3); 2.0960 (0.4); 1.9467 (0.8); 1.9412 (22.8); 1.9350 (45.5); 1.9288 (67.6); 1.9227 (46.0); 1.9165 (23.3); 1.9008 (0.5); 1.8252 (8.1); 1.8075 (8.5); 1.7804 (1.1); 1.7698 (1.1); 1.7570 (6.8); 1.7396 (6.3); 1.7107 (0.4); 0.7623 (0.4); 0.7538 (0.8); 0.7418 (0.9); 0.7336 (0.9); 0.7217 (0.9); 0.7134 (0.5); 0.7014 (0.3); 0.5184 (0.7); 0.3695 (1.1); 0.3588 (1.1); 0.3467 (1.5); 0.3352 (1.7); 0.3250 (1.7); 0.3123 (1.5); 0.3027 (1.4); 0.2938 (1.2); 0.2811 (1.1); 0.2718 (1.2); 0.2608 (1.0); 0.2417 (2.4); 0.2246 (1.8); -0.0209 (0.4); -0.0334 (0.9); -0.0455 (1.3); -0.0578 (1.3); -0.0684 (0.9); -0.0808 (0.4) | 455.2 | |
I-027 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9325 (7.6); 8.9203 (7.8); 8.7866 (13.5); 8.7745 (13.7); 8.3088 (1.0); 8.2551 (12.0); 8.2403 (6.9); 8.1311 (0.6); 7.6289 (2.1); 7.6168 (4.1); 7.6050 (5.6); 7.5931 (7.0); 7.5809 (3.5); 6.4803 (7.9); 6.3727 (0.6); 6.3557 (2.6); 6.3428 (4.2); 6.3259 (3.9); 6.3089 (1.1); 6.2854 (4.8); 3.3465 (530.8); 3.2310 (0.9); 3.2146 (0.9); 3.1955 (3.7); 3.1794 (7.1); 3.1631 (3.8); 3.1446 (0.9); 3.1277 (1.7); 3.1100 (1.0); 3.0887 (1.8); 3.0710 (1.8); 3.0286 (1.7); 3.0131 (1.8); 2.9897 (0.9); 2.9745 (0.8); 2.6783 (0.7); 2.6738 (0.9); 2.6694 (0.7); 2.5440 (5.8); 2.5269 (2.7); 2.5134 (61.3); 2.5092 (120.4); 2.5048 (155.7); 2.5003 (112.3); 2.4960 (54.9); 2.4722 (27.0); 2.4117 (16.0); 2.3359 (0.7); 2.3315 (1.0); 2.3272 (0.7); 2.0731 (1.9); 1.8051 (13.8); 1.7880 (13.7); 1.7404 (8.3); 1.7230 (8.2); 0.6159 (0.8); 0.6021 (1.3); 0.5832 (1.7); 0.5655 (2.0); 0.5531 (1.2); 0.5491 (1.2); 0.5332 (0.6); 0.2847 (0.4); 0.2758 (0.8); 0.2614 (1.4); 0.2540 (2.1); 0.2395 (2.5); 0.2313 (3.2); 0.2248 (2.9); 0.2182 (3.8); 0.2102 (3.4); 0.1979 (3.9); 0.1878 (2.1); 0.1773 (1.7); 0.1648 (0.6); 0.1562 (0.8); 0.1451 (1.1); 0.1326 (1.7); 0.1243 (1.5); 0.1196 (1.5); 0.1095 (1.6); 0.0922 (0.7); -0.0002 (2.1); -0.0363 (0.4); -0.0483 (0.9); -0.0612 (1.1); -0.0725 (1.2); -0.0809 (0.9); -0.0918 (0.4); -0.2220 (0.8); -0.2283 (1.1); -0.2332 (1.6); -0.2407 (1.9); -0.2517 (2.3); -0.2635 (2.4); -0.2825 (1.2); -0.2953 (0.9); -0.3073 (0.4) | 354.2 | |
I-028 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9310 (8.7); 8.9188 (8.9); 8.7810 (15.7); 8.7689 (16.0); 8.3081 (1.1); 8.2492 (13.2); 8.2376 (7.7); 7.6280 (2.4); 7.6161 (8.6); 7.6041 (10.2); 7.5920 (4.1); 6.4594 (13.0); 6.3627 (0.6); 6.3458 (2.2); 6.3280 (3.0); 6.3098 (4.1); 6.2925 (3.7); 6.2755 (1.0); 6.2571 (7.9); 3.3491 (607.4); 3.2346 (0.6); 3.2179 (0.6); 3.1989 (4.4); 3.1918 (4.7); 3.1824 (4.7); 3.1752 (4.6); 3.1563 (0.6); 3.1396 (0.6); 3.1244 (0.9); 3.1067 (0.9); 3.0856 (1.8); 3.0680 (1.8); 3.0280 (1.7); 3.0127 (1.8); 2.9892 (0.9); 2.9740 (0.8); 2.6787 (0.7); 2.6741 (1.0); 2.6695 (0.7); 2.5443 (1.1); 2.5274 (2.6); 2.5140 (62.4); 2.5096 (126.6); 2.5051 (166.6); 2.5006 (120.0); 2.4961 (57.9); 2.3408 (0.3); 2.3365 (0.7); 2.3318 (1.0); 2.3275 (0.7); 2.2127 (0.7); 2.2000 (1.6); 2.1915 (1.7); 2.1790 (3.3); 2.1664 (2.0); 2.1579 (2.0); 2.1419 (2.0); 2.1293 (1.1); 2.1206 (1.0); 2.1082 (0.5); 2.0730 (4.1); 1.7942 (14.2); 1.7771 (14.2); 1.7300 (8.6); 1.7126 (8.6); 1.1497 (1.0); 1.1454 (1.2); 1.1388 (4.5); 1.1318 (5.1); 1.1259 (2.5); 1.1177 (4.8); 1.1107 (5.0); 1.1054 (1.8); 1.1006 (2.4); 1.0894 (3.1); 1.0828 (3.5); 1.0728 (1.8); 1.0684 (3.0); 1.0618 (3.1); 1.0522 (1.2); 0.9866 (0.4); 0.9691 (2.3); 0.9624 (3.2); 0.9569 (4.8); 0.9520 (5.6); 0.9457 (4.5); 0.9399 (3.5); 0.9333 (1.8); 0.9233 (0.5); 0.9153 (1.6); 0.9054 (3.5); 0.8991 (3.3); 0.8933 (3.4); 0.8869 (3.4); 0.8757 (0.9); 0.6240 (0.4); 0.6109 (1.0); 0.5943 (1.9); 0.5867 (1.7); 0.5744 (2.3); 0.5666 (1.4); 0.5618 (1.5); 0.5423 (0.6); 0.2823 (0.4); 0.2731 (0.9); 0.2604 (1.6); 0.2520 (2.3); 0.2388 (3.4); 0.2304 (3.4); 0.2183 (4.5); 0.2087 (3.4); 0.1987 (4.2); 0.1883 (2.2); 0.1783 (1.9); 0.1658 (0.6); 0.1573 (0.8); 0.1485 (1.2); 0.1359 (1.7); 0.1281 (1.5); 0.1230 (1.6); 0.1134 (1.6); 0.1103 (1.6); 0.1012 (1.0); 0.0961 (0.7); -0.0002 (1.8); -0.0424 (0.4); -0.0549 (0.9); -0.0679 (1.1); -0.0787 (1.2); -0.0870 (1.0); -0.0983 (0.4); -0.2068 (0.8); -0.2128 (1.1); -0.2180 (1.6); -0.2252 (1.9); -0.2357 (1.8); -0.2382 (1.8); -0.2481 (1.6); -0.2599 (1.2); -0.2702 (1.1); -0.2789 (1.3); -0.2910 (1.2); -0.3030 (0.8); -0.3154 (0.4) | 380.2 | |
I-029 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9234 (2.9); 8.9131 (3.0); 8.7614 (7.0); 8.7496 (7.0); 8.3087 (1.2); 8.2835 (7.1); 8.2657 (2.8); 7.6230 (7.9); 7.6109 (15.0); 7.5987 (7.5); 7.4080 (6.3); 7.2095 (2.4); 6.3329 (1.0); 6.3168 (1.1); 6.1585 (0.9); 6.1420 (2.4); 6.1251 (2.4); 6.1087 (0.8); 3.3479 (632.4); 3.1986 (0.4); 3.1549 (4.2); 3.1469 (4.3); 3.1402 (4.1); 3.1094 (1.0); 3.1013 (1.0); 3.0858 (1.6); 3.0694 (2.3); 2.6790 (0.7); 2.6744 (1.0); 2.6698 (0.7); 2.6654 (0.4); 2.5446 (1.1); 2.5278 (2.7); 2.5143 (62.1); 2.5100 (125.8); 2.5054 (165.0); 2.5009 (118.5); 2.4964 (57.2); 2.3367 (0.7); 2.3322 (1.0); 2.3276 (0.7); 2.0735 (16.0); 1.8397 (8.8); 1.8229 (9.1); 1.7346 (4.0); 1.7185 (3.8); 0.5874 (0.9); 0.5050 (1.6); 0.3200 (0.9); 0.2814 (0.7); 0.2559 (1.0); 0.2501 (1.1); 0.2375 (1.0); 0.2249 (1.2); 0.1873 (3.1); 0.1683 (3.1); 0.1482 (1.7); 0.1294 (1.8); 0.1223 (1.8); 0.0995 (1.7); 0.0079 (0.4); -0.0002 (4.4); -0.0086 (0.8); -0.0229 (0.9); -0.0331 (1.0); -0.2842 (3.5); -0.2966 (3.5); -0.3087 (2.4); -0.3199 (1.1) | 374.1 | |
I-030 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 9.1725 (2.8); 8.8398 (4.8); 8.8277 (5.3); 8.7807 (8.1); 8.6271 (8.7); 8.4540 (0.4); 8.3589 (2.0); 8.3472 (2.0); 8.0861 (14.6); 7.9280 (5.6); 7.6362 (5.3); 7.4566 (2.4); 7.4445 (4.9); 7.4191 (14.2); 6.6217 (1.0); 6.6098 (1.8); 6.5980 (1.0); 6.4479 (3.9); 6.3412 (3.5); 6.2706 (0.8); 3.5090 (0.6); 3.4929 (0.6); 3.4725 (0.7); 3.4571 (0.8); 3.3896 (0.6); 3.3723 (0.9); 3.3537 (0.6); 3.2588 (4.0); 3.1144 (16.0); 3.0977 (16.0); 3.0772 (9.4); 3.0602 (8.6); 2.9239 (0.3); 2.5205 (0.9); 2.3850 (5.1); 2.3596 (7.9); 2.3274 (746.7); 2.1950 (0.7); 2.1393 (0.9); 2.1331 (1.6); 2.1269 (2.1); 2.1208 (1.6); 2.1146 (0.9); 2.0963 (0.6); 2.0398 (1.2); 2.0037 (1.1); 1.9963 (1.2); 1.9899 (1.2); 1.9838 (2.0); 1.9775 (5.5); 1.9721 (112.5); 1.9660 (226.3); 1.9598 (332.9); 1.9537 (229.0); 1.9475 (119.1); 1.9347 (5.7); 1.9322 (5.5); 1.9261 (3.8); 1.9198 (3.0); 1.8726 (14.1); 1.8008 (4.9); 1.7946 (5.8); 1.7884 (7.0); 1.7823 (6.9); 1.7760 (7.0); 1.7442 (13.3); 1.7147 (9.0); 1.6967 (5.9); 1.5770 (0.5); 1.3764 (0.4); 1.2568 (1.3); 1.0766 (0.7); 0.8793 (0.5); 0.6099 (4.0); 0.5180 (4.2); 0.4010 (4.2); 0.3184 (2.1); 0.3051 (2.4); 0.2508 (5.0); 0.2397 (5.2); 0.2033 (6.4); 0.1810 (6.9); 0.0628 (9.9); -0.0034 (1.1); -0.0162 (0.9); -0.0257 (0.7) | 390.1 | |
I-031 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 9.0236 (0.3); 8.8364 (1.2); 8.5734 (0.6); 8.5583 (0.9); 8.5386 (1.1); 8.2277 (0.8); 8.0696 (0.7); 7.8659 (0.8); 7.7241 (0.9); 7.6840 (0.9); 7.6794 (0.9); 7.6719 (1.0); 7.4921 (1.4); 7.3984 (0.6); 6.4533 (0.5); 6.1818 (0.6); 6.1577 (0.5); 6.0495 (0.4); 3.9046 (2.7); 3.8709 (1.5); 3.8555 (1.1); 3.8170 (3.0); 3.6881 (0.4); 3.6779 (0.4); 3.6716 (1.0); 3.6614 (1.0); 3.6550 (1.3); 3.6449 (1.3); 3.6385 (1.0); 3.6283 (1.0); 3.6220 (0.4); 3.6118 (0.4); 3.3360 (0.5); 3.2629 (1.9); 3.1699 (0.7); 3.1590 (0.7); 3.1513 (2.0); 3.1404 (2.0); 3.1328 (2.0); 3.1219 (2.0); 3.1143 (0.8); 3.1035 (0.8); 3.0888 (0.4); 3.0348 (1.1); 3.0051 (1.8); 2.9712 (0.7); 2.9664 (0.6); 2.9528 (0.5); 2.9377 (0.4); 2.8922 (0.3); 2.8628 (0.8); 2.8558 (1.0); 2.7848 (0.7); 2.6143 (1.4); 2.4889 (9.3); 2.1326 (0.4); 2.1264 (0.5); 2.1203 (0.4); 1.9966 (0.3); 1.9904 (0.4); 1.9879 (0.3); 1.9841 (0.4); 1.9772 (0.8); 1.9716 (19.4); 1.9655 (39.2); 1.9593 (57.6); 1.9531 (39.3); 1.9469 (19.9); 1.9398 (1.0); 1.9381 (1.3); 1.9335 (0.4); 1.9321 (0.4); 1.8433 (2.8); 1.8123 (2.6); 1.8005 (2.3); 1.7942 (2.0); 1.7880 (1.7); 1.7819 (1.2); 1.7751 (1.0); 1.7574 (0.6); 1.3182 (3.1); 1.3078 (11.2); 1.2989 (16.0); 1.2911 (11.6); 1.2819 (13.9); 0.7042 (0.5); 0.5441 (0.4); 0.5325 (0.4); 0.5131 (0.5); 0.4388 (0.8); 0.1566 (0.8); 0.0556 (1.5); -0.0780 (0.6) | 353.2 | |
I-032 | 1H-NMR(400.6 MHz, CD3CN, 260 K): δ= 8.8248 (3.0); 8.7843 (0.9); 8.7809 (0.8); 8.7730 (0.7); 8.7697 (0.6); 8.6311 (2.4); 8.0438 (2.4); 7.5656 (0.4); 7.5544 (0.6); 7.5334 (2.5); 7.4638 (3.5); 7.2242 (3.4); 6.3893 (2.5); 3.8061 (1.4); 3.7795 (8.5); 3.7411 (16.0); 3.2821 (1.6); 3.2627 (1.8); 3.2515 (2.9); 3.0341 (2.3); 2.9486 (1.8); 2.9236 (2.0); 2.8814 (1.1); 2.8629 (0.7); 2.7955 (0.4); 2.6419 (0.7); 2.6174 (0.6); 2.3583 (13.1); 2.1393 (0.7); 2.1331 (0.8); 2.1270 (0.9); 2.1208 (0.8); 2.1147 (0.6); 2.0963 (0.5); 2.0161 (0.4); 2.0100 (0.4); 2.0042 (0.4); 1.9977 (0.4); 1.9909 (0.4); 1.9838 (0.7); 1.9776 (1.5); 1.9721 (26.6); 1.9660 (53.3); 1.9598 (77.5); 1.9537 (52.8); 1.9475 (26.6); 1.9409 (1.1); 1.9322 (0.7); 1.9259 (0.4); 1.8009 (8.7); 1.7887 (7.3); 0.7314 (1.0); 0.6335 (1.5); 0.3540 (0.8); 0.3324 (2.6); 0.3199 (4.1); 0.3117 (5.0); 0.2993 (5.1); 0.2916 (4.9); 0.1660 (1.1); -0.0906 (2.7) | 387.1 | |
I-033 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6384 (0.9); 9.6206 (0.9); 8.9936 (5.2); 8.9814 (5.3); 8.4694 (1.2); 8.4651 (2.2); 8.4609 (1.5); 8.3997 (3.0); 8.1847 (4.1); 7.6380 (1.4); 7.6259 (2.6); 7.6137 (1.3); 6.0409 (0.7); 6.0234 (1.1); 6.0059 (0.7); 5.7568 (1.8); 3.3283 (32.3); 2.5264 (0.5); 2.5130 (10.7); 2.5086 (22.1); 2.5041 (29.3); 2.4995 (21.1); 2.4951 (10.2); 2.0875 (16.0); 1.6661 (4.3); 1.6487 (4.3); 0.0079 (0.7); -0.0002 (20.7); -0.0085 (0.7) | 460.9 | |
I-034 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4401 (1.5); 9.4219 (1.5); 8.9620 (7.4); 8.9499 (7.5); 8.2666 (2.0); 8.2629 (3.6); 8.2592 (2.2); 8.1681 (1.9); 8.1636 (3.2); 8.1596 (2.2); 8.1356 (2.4); 8.1314 (3.3); 8.1268 (1.7); 7.5985 (2.0); 7.5863 (3.8); 7.5742 (1.9); 6.0359 (1.1); 6.0182 (1.6); 6.0005 (1.1); 3.3291 (25.0); 3.3183 (16.1); 2.5264 (0.7); 2.5130 (11.3); 2.5087 (21.8); 2.5042 (28.0); 2.4997 (20.4); 2.4954 (10.3); 2.3373 (16.0); 2.0767 (0.5); 1.6332 (6.0); 1.6158 (5.9); 0.0079 (0.6); -0.0002 (15.0); -0.0084 (0.7) | 421.2 | |
I-035 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5064 (4.0); 9.4890 (4.1); 9.0776 (7.0); 9.0757 (6.5); 9.0722 (7.4); 9.0704 (5.7); 8.5901 (4.9); 8.5846 (4.7); 8.5686 (5.3); 8.5631 (5.2); 8.2941 (5.7); 8.2905 (9.8); 8.2868 (5.8); 8.2550 (15.4); 8.2020 (5.4); 8.1979 (8.3); 8.1937 (5.5); 8.1524 (6.2); 8.1483 (8.5); 8.1437 (4.5); 8.0931 (7.5); 8.0716 (7.0); 8.0700 (5.8); 6.1431 (0.6); 6.1258 (2.7); 6.1085 (4.3); 6.0911 (2.8); 6.0739 (0.6); 3.3271 (96.5); 2.6775 (0.4); 2.6730 (0.6); 2.6685 (0.4); 2.5084 (69.8); 2.5039 (87.0); 2.4995 (62.5); 2.3351 (0.4); 2.3307 (0.6); 1.6533 (16.0); 1.6359 (15.9); 0.0078 (2.1); -0.0002 (44.8); -0.0083 (2.1) | 431.2 | |
I-036 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4626 (2.0); 9.4448 (2.1); 9.1061 (16.0); 8.2460 (2.9); 8.2424 (5.1); 8.2388 (3.1); 8.1820 (8.6); 8.1644 (2.6); 8.1600 (4.6); 8.1561 (3.3); 8.1421 (3.6); 8.1380 (4.6); 8.1334 (2.2); 5.9493 (1.4); 5.9318 (2.2); 5.9144 (1.4); 5.8969 (0.3); 3.3462 (0.5); 3.3263 (51.3); 3.3155 (23.1); 2.6719 (0.4); 2.5117 (25.0); 2.5076 (47.1); 2.5031 (59.4); 2.4986 (43.0); 2.4944 (21.4); 2.3298 (0.4); 2.0754 (0.6); 1.6504 (8.6); 1.6330 (8.5); 0.0077 (1.3); -0.0002 (28.7); -0.0083 (1.3) | 425.1 | |
I-037 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4626 (2.0); 9.4448 (2.1); 9.1061 (16.0); 8.2460 (2.9); 8.2424 (5.1); 8.2388 (3.1); 8.1820 (8.6); 8.1644 (2.6); 8.1600 (4.6); 8.1561 (3.3); 8.1421 (3.6); 8.1380 (4.6); 8.1334 (2.2); 5.9493 (1.4); 5.9318 (2.2); 5.9144 (1.4); 5.8969 (0.3); 3.3462 (0.5); 3.3263 (51.3); 3.3155 (23.1); 2.6719 (0.4); 2.5117 (25.0); 2.5076 (47.1); 2.5031 (59.4); 2.4986 (43.0); 2.4944 (21.4); 2.3298 (0.4); 2.0754 (0.6); 1.6504 (8.6); 1.6330 (8.5); 0.0077 (1.3); -0.0002 (28.7); -0.0083 (1.3) | 407.1 | |
I-038 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.4514 (1.5); 9.4395 (1.5); 9.1214 (16.0); 8.2545 (2.1); 8.2519 (3.9); 8.2494 (2.2); 8.1970 (6.4); 8.1650 (2.0); 8.1620 (3.3); 8.1592 (2.3); 8.1382 (2.3); 8.1353 (3.4); 8.1322 (1.7); 5.9919 (1.1); 5.9803 (1.8); 5.9687 (1.1); 3.3328 (0.3); 3.3131 (18.2); 3.3070 (41.3); 2.5226 (0.5); 2.5194 (0.6); 2.5164 (0.7); 2.5075 (14.7); 2.5045 (32.0); 2.5015 (44.7); 2.4985 (32.2); 2.4955 (14.9); 2.0722 (0.4); 1.6469 (6.6); 1.6352 (6.6); -0.0002 (2.8) | 441.1 | |
I-039 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9992 (0.6); 8.6941 (3.8); 8.6832 (3.7); 8.3156 (0.4); 8.2841 (8.4); 8.0634 (0.4); 7.9132 (2.6); 7.7788 (0.4); 7.7102 (8.4); 7.6827 (0.4); 7.5875 (2.7); 7.5395 (2.0); 6.0446 (1.3); 6.0287 (1.3); 5.7557 (16.0); 4.0560 (1.0); 4.0382 (3.1); 4.0204 (3.2); 4.0026 (1.4); 3.9655 (0.9); 3.9426 (0.9); 3.9286 (0.9); 3.9172 (0.8); 3.9033 (0.9); 3.8902 (0.9); 3.8820 (0.9); 3.4659 (0.4); 3.3245 (138.4); 3.2938 (30.4); 2.7340 (0.6); 2.7057 (0.7); 2.6807 (1.0); 2.6762 (1.3); 2.6716 (1.7); 2.6669 (1.4); 2.6625 (1.0); 2.6374 (0.8); 2.6273 (0.8); 2.6025 (0.7); 2.5251 (2.8); 2.5203 (4.0); 2.5117 (56.9); 2.5072 (118.7); 2.5026 (158.0); 2.4980 (112.1); 2.4935 (52.7); 2.3381 (0.4); 2.3339 (0.8); 2.3295 (1.1); 2.3248 (0.8); 2.3203 (0.5); 2.0865 (1.1); 2.0748 (0.5); 1.9891 (13.7); 1.7129 (9.9); 1.6958 (9.9); 1.3977 (4.3); 1.2350 (0.6); 1.1931 (3.8); 1.1753 (7.6); 1.1576 (3.7); 0.1460 (0.7); 0.0080 (5.4); -0.0002 (173.2); -0.0085 (5.5); -0.1496 (0.7) | 503.0 | |
I-040 | 1H-NMR(600.1 MHz, CD3CN, 260 K): δ= 8.8901 (5.0); 8.8821 (5.1); 8.5993 (3.5); 8.5913 (3.5); 8.0994 (4.6); 8.0579 (3.1); 7.9740 (1.4); 7.9713 (2.6); 7.9685 (1.5); 7.8145 (1.0); 7.8118 (1.8); 7.8091 (1.1); 7.6273 (1.5); 7.5294 (2.5); 7.5263 (2.8); 7.5177 (2.7); 7.5097 (1.4); 7.4986 (2.8); 7.4243 (1.4); 7.4009 (1.0); 7.3929 (1.8); 7.3848 (0.9); 6.4504 (0.4); 6.4387 (1.4); 6.4271 (1.4); 6.4154 (0.4); 6.0804 (1.0); 6.0689 (1.0); 3.8047 (0.5); 3.7932 (0.9); 3.7815 (0.9); 3.7733 (0.8); 3.7616 (0.9); 3.7501 (0.5); 3.2254 (0.6); 3.2133 (0.8); 3.1994 (0.9); 3.1873 (0.8); 3.0881 (13.8); 3.0725 (9.4); 3.0231 (0.8); 3.0110 (0.9); 2.9972 (0.7); 2.9850 (0.6); 2.3046 (16.0); 1.9866 (1.4); 1.9785 (0.8); 1.9742 (1.0); 1.9706 (7.3); 1.9665 (13.1); 1.9624 (19.3); 1.9583 (13.4); 1.9542 (6.8); 1.7377 (4.6); 1.7334 (6.4); 1.7262 (4.8); 1.7217 (6.3); 1.1524 (2.1); 1.1407 (4.4); 1.1289 (2.0); 0.6555 (2.9); 0.6436 (6.2); 0.6317 (2.8) | 435.1 | |
I-041 | 1H-NMR(600.1 MHz, CD3CN, 260 K): δ= 8.8918 (0.7); 8.8839 (0.7); 8.5935 (6.0); 8.5854 (6.1); 8.1000 (0.6); 8.0572 (5.4); 7.9902 (0.4); 7.8337 (1.8); 7.8311 (3.1); 7.8285 (2.0); 7.6435 (2.7); 7.6123 (0.5); 7.5754 (0.4); 7.5193 (0.4); 7.4893 (2.5); 7.3911 (1.6); 7.3830 (3.1); 7.3750 (1.6); 6.3337 (0.4); 6.3299 (0.3); 6.2368 (1.1); 6.2247 (1.6); 6.2131 (1.6); 6.2016 (0.5); 6.1448 (0.4); 6.1409 (0.3); 5.4730 (14.2); 4.2271 (0.4); 4.2228 (0.4); 4.2177 (0.4); 4.2134 (0.4); 4.2026 (0.7); 4.1931 (0.7); 4.1818 (0.4); 4.1782 (0.4); 4.1727 (0.7); 4.1646 (0.4); 4.1593 (0.4); 4.1393 (0.5); 4.1342 (0.5); 4.1257 (0.4); 4.1205 (0.4); 3.1132 (0.3); 3.0842 (2.1); 3.0718 (16.0); 2.3019 (6.0); 1.9863 (1.3); 1.9782 (0.8); 1.9740 (1.0); 1.9703 (7.2); 1.9662 (13.0); 1.9621 (19.1); 1.9580 (13.2); 1.9539 (6.8); 1.7637 (0.8); 1.7519 (0.9); 1.7179 (5.5); 1.7063 (5.5) | 471.2 | |
I-042 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4706 (2.6); 9.4527 (2.6); 8.9964 (15.4); 8.9843 (15.7); 8.3158 (4.3); 8.2036 (3.8); 8.1998 (7.6); 8.1961 (4.8); 8.1761 (12.8); 8.1566 (3.9); 8.1520 (6.7); 8.1481 (4.3); 8.1073 (4.3); 8.1029 (6.4); 8.0986 (3.4); 7.6417 (4.1); 7.6295 (7.9); 7.6174 (3.9); 6.0432 (0.4); 6.0264 (2.0); 6.0088 (3.1); 5.9913 (2.0); 5.9737 (0.4); 5.7562 (16.0); 3.3247 (140.3); 3.3009 (2.3); 3.0337 (0.6); 3.0217 (1.4); 3.0140 (1.5); 3.0092 (0.9); 3.0023 (2.8); 2.9902 (1.5); 2.9826 (1.4); 2.9704 (0.7); 2.6756 (1.2); 2.6710 (1.6); 2.6665 (1.2); 2.6621 (0.6); 2.5245 (4.9); 2.5195 (7.7); 2.5110 (97.6); 2.5066 (198.7); 2.5021 (261.0); 2.4975 (186.2); 2.4931 (89.1); 2.3379 (0.5); 2.3335 (1.1); 2.3289 (1.6); 2.3244 (1.2); 2.3200 (0.5); 1.6559 (13.1); 1.6385 (13.0); 1.6113 (0.5); 1.2124 (0.3); 1.1880 (1.7); 1.1800 (3.8); 1.1768 (3.8); 1.1716 (3.4); 1.1685 (3.9); 1.1601 (2.4); 1.1400 (0.5); 1.1287 (0.7); 1.1157 (0.8); 1.1088 (1.2); 1.0967 (3.5); 1.0892 (3.1); 1.0767 (3.4); 1.0718 (2.4); 1.0560 (0.6); 0.0078 (0.4); -0.0003 (11.3); -0.0086 (0.4) | 433.1 | |
I-043 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4616 (2.9); 9.4438 (2.9); 8.9854 (15.7); 8.9732 (16.0); 8.3163 (0.6); 8.2581 (3.8); 8.2543 (7.6); 8.2505 (4.8); 8.2164 (3.8); 8.2119 (6.7); 8.2077 (3.7); 8.1676 (13.0); 8.1582 (0.4); 8.1526 (0.6); 8.1450 (4.7); 8.1400 (2.1); 8.1323 (5.2); 8.1275 (3.1); 8.1226 (5.4); 8.1173 (5.5); 8.1131 (8.2); 8.1095 (8.1); 7.9671 (0.4); 7.9448 (0.4); 7.6250 (4.2); 7.6129 (8.0); 7.6007 (4.0); 7.5303 (0.6); 7.5225 (4.8); 7.5173 (1.6); 7.5004 (9.0); 7.4838 (1.9); 7.4784 (4.6); 7.4705 (0.4); 7.1652 (0.4); 7.1430 (0.4); 6.0192 (0.4); 6.0018 (2.2); 5.9843 (3.4); 5.9669 (2.2); 5.9495 (0.5); 5.7566 (2.0); 4.0558 (0.9); 4.0380 (2.9); 4.0202 (2.9); 4.0024 (1.0); 3.8390 (1.5); 3.3256 (188.6); 2.6761 (1.3); 2.6716 (1.8); 2.6670 (1.3); 2.6626 (0.6); 2.5250 (4.4); 2.5202 (7.0); 2.5115 (104.1); 2.5071 (215.8); 2.5026 (286.4); 2.4981 (203.2); 2.4936 (95.5); 2.3384 (0.6); 2.3338 (1.2); 2.3295 (1.7); 2.3249 (1.2); 1.9892 (12.5); 1.6448 (13.1); 1.6274 (13.1); 1.1929 (3.5); 1.1751 (6.9); 1.1573 (3.3); 0.1457 (0.7); 0.0078 (5.4); -0.0003 (166.6); -0.0086 (5.3); -0.1496 (0.7) | 487.2 | |
I-044 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4633 (2.1); 9.4453 (2.2); 8.9942 (14.3); 8.9820 (14.6); 8.3159 (0.4); 8.1928 (3.0); 8.1890 (6.6); 8.1851 (4.4); 8.1763 (11.1); 8.1679 (3.8); 8.1631 (5.3); 8.1592 (3.2); 8.0829 (3.6); 8.0785 (5.4); 8.0741 (3.1); 7.6385 (3.8); 7.6263 (7.3); 7.6142 (3.7); 6.0432 (0.4); 6.0260 (1.6); 6.0084 (2.6); 5.9909 (1.7); 5.9732 (0.4); 5.7563 (12.8); 3.4394 (1.8); 3.4211 (6.4); 3.4027 (6.4); 3.3843 (1.9); 3.3252 (156.6); 2.6803 (0.4); 2.6758 (0.9); 2.6712 (1.2); 2.6667 (0.9); 2.6622 (0.4); 2.5248 (3.6); 2.5201 (5.1); 2.5114 (70.2); 2.5069 (146.5); 2.5023 (194.1); 2.4977 (136.5); 2.4931 (63.6); 2.3382 (0.4); 2.3337 (0.8); 2.3291 (1.2); 2.3245 (0.9); 2.3199 (0.4); 1.6552 (10.3); 1.6378 (10.2); 1.1240 (6.9); 1.1056 (16.0); 1.0872 (6.6); 0.1459 (0.4); 0.0079 (3.0); -0.0002 (100.0); -0.0086 (3.0); -0.1497 (0.4) | 421.1 | |
I-045 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0424 (2.9); 9.0243 (3.0); 8.9883 (15.7); 8.9762 (16.0); 8.1614 (0.7); 8.1508 (12.8); 7.7165 (0.4); 7.6967 (0.4); 7.6357 (4.2); 7.6291 (0.7); 7.6235 (8.0); 7.6114 (4.0); 7.2808 (6.1); 7.2771 (10.4); 7.2617 (2.2); 7.2558 (2.4); 7.0973 (1.8); 7.0926 (2.6); 7.0880 (1.7); 7.0719 (1.9); 7.0678 (2.4); 5.9898 (0.6); 5.9723 (2.5); 5.9546 (3.7); 5.9369 (2.4); 5.9195 (0.5); 3.3265 (74.6); 2.6765 (0.5); 2.6719 (0.7); 2.6673 (0.5); 2.5252 (1.7); 2.5205 (2.5); 2.5117 (40.3); 2.5074 (84.0); 2.5029 (112.1); 2.4984 (80.3); 2.4940 (38.5); 2.3342 (0.5); 2.3296 (0.7); 2.3252 (0.5); 1.9970 (0.6); 1.9847 (1.2); 1.9762 (1.4); 1.9639 (2.5); 1.9515 (1.5); 1.9429 (1.4); 1.9307 (0.7); 1.6302 (14.4); 1.6214 (2.1); 1.6128 (14.3); 1.0126 (1.7); 1.0019 (4.5); 0.9962 (4.8); 0.9861 (2.5); 0.9810 (4.7); 0.9753 (4.6); 0.9653 (2.0); 0.7552 (2.0); 0.7449 (5.0); 0.7396 (5.0); 0.7326 (4.8); 0.7274 (5.2); 0.7164 (1.6); 0.0080 (1.8); -0.0002 (57.6); -0.0084 (1.9) | 353.2 | |
I-046 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1918 (1.2); 9.1740 (1.2); 8.9885 (6.0); 8.9763 (6.2); 8.1578 (5.1); 7.6355 (2.7); 7.6321 (3.3); 7.6276 (4.1); 7.6230 (5.7); 7.6112 (1.6); 7.5602 (1.7); 7.5559 (2.7); 7.5516 (1.5); 5.9771 (0.9); 5.9595 (1.4); 5.9419 (0.9); 3.6743 (0.4); 3.6578 (1.0); 3.6411 (1.4); 3.6245 (1.0); 3.6079 (0.4); 3.3281 (34.7); 2.5258 (0.7); 2.5210 (1.0); 2.5121 (15.7); 2.5078 (33.0); 2.5033 (44.3); 2.4987 (32.1); 2.4943 (15.6); 1.6294 (5.4); 1.6120 (5.3); 1.2679 (0.6); 1.2530 (16.0); 1.2365 (15.6); 0.0079 (0.3); -0.0002 (11.0); -0.0085 (0.4) | 403.2 | |
I-047 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0296 (0.4); 8.9668 (1.9); 8.7217 (0.4); 8.7106 (0.4); 8.3157 (0.8); 8.2511 (16.0); 8.1933 (2.2); 8.1773 (2.5); 7.8799 (1.6); 7.8648 (2.9); 7.8453 (2.2); 7.7984 (4.0); 7.7811 (2.5); 7.6369 (2.5); 6.3575 (0.8); 5.7559 (4.5); 5.3244 (0.3); 3.3253 (246.8); 2.8570 (1.4); 2.7329 (0.3); 2.6762 (1.7); 2.6716 (2.2); 2.6670 (1.7); 2.6625 (0.9); 2.5251 (7.4); 2.5203 (10.7); 2.5117 (121.2); 2.5072 (243.2); 2.5027 (317.5); 2.4981 (224.0); 2.4936 (104.5); 2.3386 (0.5); 2.3340 (1.2); 2.3295 (1.8); 2.3249 (1.2); 2.3204 (0.5); 2.0095 (0.6); 1.9905 (0.6); 1.7682 (8.0); 1.7531 (8.1); 1.4278 (0.4); 1.4097 (0.4); 1.2354 (4.4); 0.8709 (0.4); 0.8542 (1.2); 0.8365 (0.5); 0.4997 (0.8); 0.2089 (1.8); 0.1458 (1.0); 0.0080 (1.5); -0.0002 (42.1); -0.0085 (1.3); -0.3017 (0.8); -0.4709 (0.8) | 481.2 | |
I-048 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3002 (2.6); 9.2823 (2.6); 9.0007 (15.7); 8.9885 (16.0); 8.6185 (5.5); 8.6121 (5.4); 8.1889 (3.5); 8.1844 (5.4); 8.1803 (4.1); 8.1713 (12.4); 8.1602 (0.4); 8.0986 (3.8); 8.0937 (6.7); 8.0888 (3.5); 7.8124 (6.0); 7.8083 (5.9); 7.7181 (4.0); 7.7139 (6.0); 7.7099 (3.8); 7.6421 (4.3); 7.6299 (8.1); 7.6177 (4.1); 6.6022 (4.1); 6.5977 (4.7); 6.5961 (4.8); 6.5915 (4.0); 6.0400 (0.4); 6.0229 (2.0); 6.0053 (3.1); 5.9877 (2.0); 5.9703 (0.4); 5.7576 (4.7); 3.3289 (35.3); 2.6773 (0.3); 2.6729 (0.4); 2.5264 (1.3); 2.5216 (2.1); 2.5130 (26.5); 2.5085 (53.7); 2.5040 (70.2); 2.4994 (50.0); 2.4948 (23.6); 2.3308 (0.4); 2.3261 (0.3); 1.6577 (12.0); 1.6403 (11.9); -0.0002 (9.2) | 395.2 | |
I-049 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3933 (10.8); 9.3435 (2.2); 9.3256 (2.2); 9.0014 (12.8); 8.9893 (13.0); 8.2982 (10.8); 8.2102 (2.8); 8.2056 (4.8); 8.2018 (3.7); 8.1769 (3.8); 8.1719 (16.0); 8.1675 (3.3); 7.8513 (3.3); 7.8472 (5.2); 7.8432 (3.3); 7.6440 (3.5); 7.6318 (6.6); 7.6197 (3.3); 6.0431 (0.4); 6.0257 (1.7); 6.0082 (2.6); 5.9907 (1.7); 5.9734 (0.4); 5.7569 (3.9); 3.3279 (8.0); 3.0003 (0.3); 2.9866 (0.4); 2.9824 (0.4); 2.9743 (0.3); 2.9684 (0.4); 2.9538 (0.6); 2.6770 (0.4); 2.6726 (0.5); 2.6681 (0.4); 2.5429 (2.0); 2.5260 (1.4); 2.5212 (2.2); 2.5125 (29.0); 2.5081 (58.9); 2.5036 (77.3); 2.4990 (55.5); 2.4945 (26.8); 2.3350 (0.4); 2.3304 (0.5); 2.3259 (0.4); 2.1804 (2.4); 1.6580 (10.2); 1.6407 (10.2); 1.4977 (0.3); 1.2338 (0.4); 0.9887 (0.6); 0.9708 (1.3); 0.9529 (0.6); -0.0002 (9.7); -0.0085 (0.3) | 396.1 | |
I-050 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0852 (2.4); 9.0672 (2.4); 8.9890 (15.8); 8.9769 (16.0); 8.1530 (12.3); 7.6371 (4.3); 7.6250 (8.1); 7.6128 (4.1); 7.5261 (3.6); 7.5216 (5.7); 7.5174 (3.9); 7.3488 (3.1); 7.3450 (6.1); 7.3413 (3.6); 7.3113 (3.7); 7.3068 (5.7); 7.3025 (3.0); 5.9878 (0.4); 5.9706 (2.0); 5.9530 (3.1); 5.9353 (2.0); 5.9179 (0.4); 3.3263 (15.6); 2.5260 (0.7); 2.5213 (1.1); 2.5126 (18.8); 2.5082 (39.1); 2.5036 (52.0); 2.4990 (36.6); 2.4944 (17.0); 2.0764 (1.2); 1.9993 (0.6); 1.9865 (1.2); 1.9782 (1.3); 1.9743 (0.9); 1.9657 (2.5); 1.9571 (0.8); 1.9531 (1.4); 1.9448 (1.3); 1.9321 (0.7); 1.6277 (12.3); 1.6103 (12.2); 1.0088 (1.6); 0.9981 (3.9); 0.9925 (4.1); 0.9880 (2.1); 0.9822 (2.2); 0.9771 (4.0); 0.9714 (3.9); 0.9614 (1.8); 0.7568 (1.9); 0.7464 (4.3); 0.7410 (4.1); 0.7340 (4.1); 0.7288 (4.3); 0.7177 (1.4); -0.0002 (4.1) | 369.2 | |
I-051 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4752 (2.5); 9.4573 (2.6); 8.9916 (15.7); 8.9795 (16.0); 8.1928 (3.5); 8.1886 (6.0); 8.1842 (4.8); 8.1779 (12.7); 8.1664 (4.4); 8.1626 (7.4); 8.1588 (3.5); 8.0437 (4.0); 8.0394 (6.2); 8.0350 (3.4); 7.6351 (4.2); 7.6229 (8.2); 7.6108 (4.1); 6.0442 (0.4); 6.0269 (2.0); 6.0094 (3.1); 5.9918 (2.0); 5.9745 (0.4); 4.0562 (0.8); 4.0384 (2.6); 4.0206 (2.6); 4.0028 (0.9); 3.6102 (0.8); 3.5933 (2.1); 3.5762 (3.0); 3.5592 (2.2); 3.5422 (0.8); 3.3253 (60.0); 2.6766 (0.4); 2.6720 (0.6); 2.6676 (0.4); 2.5256 (1.4); 2.5208 (2.3); 2.5122 (35.3); 2.5077 (72.2); 2.5031 (94.8); 2.4985 (66.3); 2.4940 (30.3); 2.3345 (0.4); 2.3299 (0.6); 2.3255 (0.4); 1.9895 (11.5); 1.9098 (0.3); 1.6575 (12.1); 1.6401 (12.0); 1.3519 (1.0); 1.2991 (0.8); 1.2591 (1.2); 1.2342 (1.8); 1.2162 (0.4); 1.1933 (3.6); 1.1778 (15.9); 1.1757 (12.5); 1.1682 (15.8); 1.1608 (15.7); 1.1580 (7.7); 1.1512 (14.8); 0.8892 (0.3); 0.8537 (1.0); 0.8370 (0.9); -0.0002 (8.0) | 435.2 | |
I-052 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5221 (2.5); 9.5041 (2.6); 8.9684 (15.6); 8.9563 (16.0); 8.3160 (0.3); 8.2354 (12.5); 7.6427 (4.2); 7.6305 (8.0); 7.6184 (4.1); 7.4938 (0.4); 7.4851 (4.1); 7.4796 (1.5); 7.4730 (4.4); 7.4679 (2.6); 7.4625 (5.5); 7.4561 (1.8); 7.4505 (5.2); 7.4418 (0.6); 7.3616 (9.2); 7.3375 (0.6); 7.3289 (5.4); 7.3233 (1.5); 7.3161 (0.8); 7.3116 (1.7); 7.3072 (8.4); 7.3020 (1.7); 7.2906 (1.4); 7.2850 (4.0); 7.2763 (0.4); 5.9072 (0.4); 5.8898 (2.1); 5.8721 (3.2); 5.8545 (2.1); 5.8371 (0.4); 5.7564 (1.8); 3.3260 (117.6); 2.6898 (0.5); 2.6758 (0.7); 2.6713 (0.9); 2.6668 (0.7); 2.5249 (2.2); 2.5201 (3.2); 2.5114 (54.5); 2.5069 (112.9); 2.5024 (149.3); 2.4978 (105.4); 2.4933 (49.1); 2.3337 (0.7); 2.3292 (0.9); 2.3247 (0.7); 1.5704 (12.7); 1.5531 (12.7); -0.0002 (10.7) | 447.2 | |
I-053 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1950 (3.1); 9.1776 (3.1); 9.0571 (5.3); 9.0553 (6.0); 9.0516 (5.9); 9.0498 (5.8); 8.5818 (5.1); 8.5762 (4.8); 8.5603 (5.4); 8.5547 (5.4); 8.2380 (16.0); 8.0771 (6.2); 8.0753 (6.3); 8.0556 (5.9); 8.0538 (5.9); 7.4910 (7.2); 7.4874 (4.9); 7.4755 (4.1); 7.4728 (4.6); 7.4703 (4.1); 7.2728 (4.5); 6.0904 (0.5); 6.0731 (2.4); 6.0557 (3.7); 6.0383 (2.4); 6.0210 (0.5); 4.3321 (0.4); 3.3282 (48.4); 2.6777 (0.4); 2.6732 (0.6); 2.6686 (0.4); 2.5267 (1.6); 2.5221 (2.3); 2.5133 (32.6); 2.5088 (67.7); 2.5042 (88.9); 2.4996 (62.6); 2.4950 (29.3); 2.3357 (0.4); 2.3311 (0.6); 2.3265 (0.4); 2.0685 (0.7); 2.0559 (1.5); 2.0476 (1.5); 2.0436 (1.0); 2.0351 (3.0); 2.0264 (1.0); 2.0226 (1.6); 2.0141 (1.6); 2.0016 (0.8); 1.6415 (14.3); 1.6240 (14.2); 1.4770 (0.5); 1.2727 (0.4); 1.2332 (0.6); 1.0496 (1.9); 1.0385 (5.0); 1.0329 (5.3); 1.0289 (2.6); 1.0224 (2.6); 1.0175 (5.1); 1.0119 (5.1); 1.0016 (2.1); 0.7952 (2.2); 0.7846 (5.6); 0.7793 (5.6); 0.7722 (5.2); 0.7670 (6.1); 0.7555 (1.8); 0.1458 (0.4); 0.0080 (3.3); -0.0002 (112.0); -0.0086 (3.5); -0.1495 (0.4) | 443.2 | |
I-054 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1340 (3.0); 9.1166 (3.1); 9.0625 (5.7); 9.0606 (6.1); 9.0570 (6.2); 9.0551 (5.7); 8.5837 (5.4); 8.5781 (5.2); 8.5622 (5.8); 8.5567 (5.7); 8.3162 (0.4); 8.2315 (16.0); 8.0752 (6.5); 8.0733 (6.5); 8.0537 (6.2); 8.0518 (6.1); 7.5795 (4.7); 7.5750 (7.1); 7.5707 (5.1); 7.4043 (4.2); 7.4005 (7.7); 7.3968 (4.3); 7.3255 (4.5); 7.3211 (7.2); 7.3167 (3.9); 6.0759 (0.5); 6.0587 (2.4); 6.0413 (3.8); 6.0239 (2.4); 6.0067 (0.5); 5.7564 (0.8); 3.3246 (101.5); 2.6806 (0.4); 2.6760 (0.9); 2.6715 (1.3); 2.6669 (0.9); 2.6624 (0.4); 2.5250 (3.6); 2.5204 (5.2); 2.5116 (70.6); 2.5071 (145.8); 2.5025 (191.5); 2.4979 (133.6); 2.4933 (61.3); 2.3385 (0.4); 2.3339 (0.8); 2.3293 (1.2); 2.3247 (0.8); 2.3201 (0.4); 2.0750 (0.4); 2.0129 (0.7); 2.0002 (1.5); 1.9919 (1.6); 1.9879 (1.0); 1.9794 (3.1); 1.9709 (1.0); 1.9668 (1.7); 1.9584 (1.6); 1.9458 (0.8); 1.6256 (14.8); 1.6081 (14.7); 1.0166 (2.0); 1.0055 (5.2); 0.9999 (5.6); 0.9957 (2.6); 0.9895 (2.8); 0.9845 (5.6); 0.9789 (5.3); 0.9686 (2.3); 0.7685 (2.4); 0.7579 (5.8); 0.7526 (5.7); 0.7455 (5.4); 0.7403 (6.2); 0.7289 (1.9); 0.1459 (0.9); 0.0162 (0.3); 0.0141 (0.3); 0.0080 (7.5); -0.0002 (245.4); -0.0086 (7.3); -0.0127 (0.7); -0.1496 (0.9) | 393.1 | |
I-055 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5479 (3.2); 9.5304 (3.2); 9.0719 (5.5); 9.0702 (6.0); 9.0665 (6.0); 9.0647 (5.8); 8.5905 (5.0); 8.5850 (4.8); 8.5691 (5.3); 8.5635 (5.3); 8.2634 (6.2); 8.2532 (16.0); 8.2422 (10.5); 8.1831 (13.4); 8.1780 (3.7); 8.1660 (2.9); 8.1612 (8.0); 8.1568 (1.2); 8.1004 (6.3); 8.0986 (6.4); 8.0789 (5.9); 8.0771 (6.0); 6.1451 (0.5); 6.1278 (2.4); 6.1105 (3.8); 6.0930 (2.4); 6.0758 (0.5); 4.0395 (0.4); 4.0217 (0.4); 3.3282 (25.1); 2.6785 (0.4); 2.6739 (0.5); 2.6691 (0.4); 2.5274 (1.5); 2.5227 (2.1); 2.5140 (28.3); 2.5095 (58.0); 2.5049 (75.4); 2.5003 (53.2); 2.4958 (24.8); 2.3363 (0.3); 2.3319 (0.5); 2.3272 (0.3); 1.9906 (1.9); 1.6433 (14.6); 1.6260 (14.5); 1.1942 (0.5); 1.1763 (1.1); 1.1586 (0.5); 0.1459 (0.4); 0.0080 (3.4); -0.0002 (101.3); -0.0086 (3.1); -0.0120 (0.5); -0.1495 (0.4) | 451.1 | |
I-056 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5024 (2.4); 9.4844 (2.5); 9.0033 (15.6); 8.9911 (16.0); 8.2466 (5.2); 8.2255 (7.5); 8.1723 (12.0); 8.1425 (0.7); 8.1322 (9.8); 8.1272 (2.8); 8.1151 (2.5); 8.1104 (6.8); 8.1057 (1.0); 7.6464 (4.3); 7.6342 (8.2); 7.6221 (4.2); 6.0547 (0.4); 6.0375 (1.9); 6.0199 (3.0); 6.0023 (1.9); 5.9850 (0.4); 3.3343 (24.7); 2.5284 (0.9); 2.5237 (1.3); 2.5150 (17.3); 2.5106 (34.6); 2.5060 (44.5); 2.5014 (31.1); 2.4968 (14.4); 2.0778 (0.4); 1.6481 (11.7); 1.6308 (11.6); 0.0079 (1.8); -0.0002 (56.6); -0.0086 (1.9) | 427.2 | |
I-057 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2537 (0.9); 9.2357 (1.0); 8.9948 (6.9); 8.9827 (7.0); 8.1608 (4.8); 7.9251 (1.4); 7.9212 (2.8); 7.9174 (1.6); 7.8254 (0.8); 7.8205 (2.6); 7.8156 (3.2); 7.8113 (2.6); 7.8063 (0.8); 7.6399 (1.8); 7.6277 (3.5); 7.6156 (1.8); 5.9924 (0.7); 5.9749 (1.1); 5.9573 (0.7); 3.9466 (16.0); 3.3251 (7.8); 2.5255 (0.6); 2.5208 (1.0); 2.5121 (13.6); 2.5076 (28.1); 2.5030 (36.8); 2.4984 (25.9); 2.4938 (12.0); 2.1850 (14.8); 2.0756 (0.4); 1.6444 (4.5); 1.6269 (4.5); 0.0079 (1.5); -0.0002 (45.7); -0.0086 (1.4) | 400.2 | |
I-058 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5471 (2.7); 9.5288 (2.7); 9.1163 (4.8); 9.1111 (4.6); 8.6022 (3.0); 8.5968 (3.0); 8.5807 (3.3); 8.5753 (3.3); 8.3186 (6.5); 8.3152 (4.3); 8.2987 (10.3); 8.2263 (3.6); 8.2221 (5.7); 8.2183 (3.8); 8.1604 (3.8); 8.1561 (5.7); 8.1520 (3.3); 8.0997 (4.7); 8.0782 (4.3); 7.9532 (0.4); 6.4566 (0.9); 6.4427 (1.5); 6.4378 (1.9); 6.4243 (2.1); 6.4052 (0.9); 3.9319 (1.1); 3.9062 (3.0); 3.8856 (5.0); 3.8710 (3.2); 3.8591 (1.3); 3.8454 (0.9); 3.3407 (36.3); 3.3279 (86.9); 3.2787 (0.7); 2.8918 (2.9); 2.7323 (2.6); 2.6768 (0.5); 2.6723 (0.6); 2.5077 (74.5); 2.5034 (93.8); 2.4990 (69.1); 2.3344 (0.4); 2.3302 (0.6); 2.3258 (0.4); 2.0755 (16.0); 0.1460 (0.4); 0.0075 (4.0); -0.0002 (75.9); -0.0082 (4.0); -0.1496 (0.4) | 461.2 | |
I-059 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4985 (2.9); 9.4796 (3.0); 9.0227 (15.7); 9.0105 (16.0); 8.9372 (1.8); 8.9250 (1.8); 8.4465 (1.7); 8.2789 (4.2); 8.2752 (7.6); 8.2715 (4.5); 8.2192 (12.7); 8.1836 (3.9); 8.1791 (6.5); 8.1751 (4.5); 8.1473 (4.9); 8.1430 (6.7); 8.1385 (3.5); 8.1162 (0.5); 8.1119 (0.8); 8.1073 (0.5); 8.0183 (0.5); 8.0143 (0.8); 8.0097 (0.5); 7.9932 (0.6); 7.9894 (0.9); 7.9856 (0.4); 7.7046 (0.5); 7.6925 (1.0); 7.6803 (0.6); 7.6714 (4.3); 7.6592 (8.1); 7.6471 (4.2); 6.3425 (1.0); 6.3238 (2.3); 6.3086 (2.6); 6.2899 (1.0); 3.9325 (0.8); 3.9070 (4.1); 3.8984 (3.9); 3.8879 (4.6); 3.8836 (4.7); 3.8731 (1.0); 3.8579 (0.5); 3.4933 (0.3); 3.3264 (81.9); 3.3197 (75.8); 3.3031 (4.9); 3.2817 (0.3); 3.2632 (0.4); 2.6762 (0.7); 2.6717 (0.9); 2.6673 (0.6); 2.5251 (3.3); 2.5116 (56.2); 2.5073 (109.3); 2.5028 (139.6); 2.4982 (99.0); 2.4938 (47.2); 2.3340 (0.6); 2.3295 (0.9); 2.3251 (0.6); 0.1459 (0.4); 0.0080 (3.7); -0.0002 (88.8); -0.0084 (3.2); -0.1495 (0.4) | 437.1 | |
I-060 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2497 (0.4); 9.2318 (0.5); 8.9815 (2.8); 8.9693 (2.8); 8.1610 (2.3); 7.8900 (0.6); 7.8855 (1.0); 7.8811 (0.7); 7.8091 (0.7); 7.8053 (1.3); 7.8016 (0.7); 7.6677 (0.7); 7.6632 (1.1); 7.6589 (0.7); 7.6262 (0.8); 7.6141 (1.4); 7.6019 (0.7); 5.9906 (0.3); 5.9730 (0.5); 5.9554 (0.3); 5.7560 (2.5); 3.3263 (18.7); 2.5209 (0.4); 2.5122 (6.4); 2.5077 (13.5); 2.5031 (18.1); 2.4985 (13.0); 2.4940 (6.2); 1.6363 (2.1); 1.6189 (2.1); 1.2425 (16.0); -0.0002 (0.7) | 417.1 | |
I-061 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5687 (3.1); 9.5510 (3.2); 9.0057 (5.5); 9.0039 (6.1); 9.0002 (6.0); 8.9984 (5.8); 8.5692 (5.2); 8.5636 (5.0); 8.5477 (5.5); 8.5421 (5.5); 8.3271 (16.0); 8.3158 (0.6); 8.2359 (0.4); 8.0723 (6.3); 8.0705 (6.4); 8.0508 (5.8); 8.0489 (6.0); 7.5235 (0.5); 7.5148 (5.2); 7.5092 (1.9); 7.5027 (5.6); 7.4975 (3.2); 7.4922 (6.6); 7.4857 (2.3); 7.4801 (6.2); 7.4713 (0.8); 7.4632 (0.3); 7.4116 (11.1); 7.3346 (0.7); 7.3260 (6.4); 7.3202 (1.8); 7.3133 (1.0); 7.3088 (2.2); 7.3041 (10.0); 7.2990 (2.1); 7.2876 (1.8); 7.2820 (5.1); 7.2732 (0.4); 5.9977 (0.5); 5.9804 (2.4); 5.9629 (3.9); 5.9454 (2.5); 5.9282 (0.5); 5.7561 (0.8); 3.3250 (175.5); 2.6804 (0.6); 2.6758 (1.2); 2.6712 (1.7); 2.6666 (1.2); 2.6622 (0.6); 2.5247 (4.8); 2.5201 (7.0); 2.5114 (94.9); 2.5069 (195.2); 2.5023 (256.3); 2.4976 (179.6); 2.4931 (83.0); 2.3382 (0.5); 2.3337 (1.1); 2.3291 (1.6); 2.3245 (1.1); 2.3199 (0.5); 1.6057 (0.4); 1.5883 (0.6); 1.5708 (14.8); 1.5534 (14.7); 1.2340 (0.4); 0.1459 (0.8); 0.0080 (6.4); -0.0002 (205.6); -0.0086 (6.1); -0.1496 (0.8) | 471.2 | |
I-062 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0807 (5.5); 9.0789 (6.1); 9.0752 (6.0); 9.0734 (5.8); 9.0363 (3.2); 9.0180 (3.3); 8.5873 (5.0); 8.5817 (4.8); 8.5658 (5.4); 8.5603 (5.4); 8.3270 (0.4); 8.3159 (0.5); 8.2359 (16.0); 8.0796 (6.2); 8.0779 (6.3); 8.0581 (5.8); 8.0563 (5.9); 7.7068 (0.4); 7.6980 (3.9); 7.6859 (4.2); 7.6808 (2.7); 7.6756 (4.8); 7.6637 (4.6); 7.6549 (0.4); 7.4931 (0.8); 7.4846 (6.4); 7.4789 (2.2); 7.4682 (12.4); 7.4629 (10.3); 7.4578 (2.2); 7.4535 (0.8); 7.4464 (1.7); 7.4408 (5.2); 7.4322 (0.4); 6.1207 (0.5); 6.1034 (2.5); 6.0857 (3.8); 6.0680 (2.5); 6.0506 (0.5); 5.7562 (0.4); 3.3258 (193.5); 2.6805 (0.5); 2.6759 (1.1); 2.6714 (1.5); 2.6668 (1.1); 2.6622 (0.5); 2.5249 (4.7); 2.5202 (6.9); 2.5115 (89.7); 2.5070 (183.5); 2.5024 (240.6); 2.4978 (168.5); 2.4932 (77.9); 2.3382 (0.5); 2.3339 (1.0); 2.3292 (1.5); 2.3246 (1.1); 2.3202 (0.5); 1.6059 (14.6); 1.5886 (14.6); 1.5710 (0.5); 1.5535 (0.4); 0.1459 (0.7); 0.0161 (0.3); 0.0139 (0.4); 0.0080 (6.1); -0.0002 (187.3); -0.0086 (5.4); -0.1496 (0.7) | 471.2 | |
I-063 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4550 (2.4); 9.4373 (2.4); 9.4122 (0.4); 8.4873 (4.0); 8.4806 (4.1); 8.2737 (3.5); 8.2700 (6.6); 8.2662 (3.9); 8.1678 (3.6); 8.1627 (16.0); 8.1398 (4.2); 8.1355 (5.7); 8.1310 (2.8); 7.9784 (1.3); 7.9716 (1.2); 7.9562 (3.7); 7.9494 (3.8); 7.9332 (6.3); 7.9322 (6.3); 7.9111 (2.1); 7.5715 (2.8); 7.3890 (5.8); 7.2065 (2.9); 6.0004 (0.4); 5.9833 (1.8); 5.9659 (2.7); 5.9484 (1.8); 5.9309 (0.4); 5.7563 (0.4); 3.3255 (40.8); 3.3154 (29.1); 2.6765 (0.4); 2.6719 (0.6); 2.6673 (0.4); 2.5254 (2.0); 2.5206 (3.0); 2.5120 (36.6); 2.5075 (73.5); 2.5030 (95.4); 2.4984 (67.9); 2.4940 (32.4); 2.3343 (0.4); 2.3299 (0.6); 2.3252 (0.4); 1.6449 (10.3); 1.6275 (10.3); 1.2342 (0.5); 0.0080 (2.1); -0.0002 (65.2); -0.0085 (2.5) | 472.1 | |
I-064 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4745 (2.2); 9.4569 (2.3); 8.8398 (4.0); 8.8342 (3.9); 8.4567 (2.1); 8.4509 (2.0); 8.4354 (2.4); 8.4295 (2.3); 8.2778 (3.4); 8.2739 (6.5); 8.2701 (3.8); 8.2353 (11.0); 8.1683 (3.0); 8.1636 (5.3); 8.1597 (3.9); 8.1417 (4.0); 8.1373 (5.5); 8.1329 (2.6); 8.0559 (4.4); 8.0545 (4.5); 8.0346 (4.0); 8.0331 (4.1); 6.1354 (0.3); 6.1179 (1.6); 6.1006 (2.6); 6.0831 (1.6); 6.0661 (0.4); 3.3258 (66.7); 3.3123 (27.6); 2.6766 (0.5); 2.6719 (0.6); 2.6673 (0.4); 2.5255 (1.8); 2.5207 (2.8); 2.5121 (36.6); 2.5076 (74.7); 2.5030 (97.3); 2.4984 (68.6); 2.4938 (32.0); 2.3345 (0.4); 2.3299 (0.6); 2.3253 (0.4); 2.0755 (16.0); 1.6622 (9.8); 1.6448 (9.8); 0.0080 (2.4); -0.0002 (73.0); -0.0086 (2.3) | 506.1 | |
I-065 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3830 (3.2); 9.3652 (3.3); 9.0877 (5.7); 9.0859 (6.2); 9.0823 (6.2); 9.0804 (5.9); 9.0466 (7.8); 9.0410 (7.8); 8.9352 (7.8); 8.9301 (7.9); 8.5896 (5.3); 8.5840 (5.0); 8.5681 (5.6); 8.5625 (5.6); 8.4437 (4.4); 8.4383 (7.8); 8.4329 (4.1); 8.3164 (0.7); 8.2574 (16.0); 8.0989 (6.4); 8.0971 (6.4); 8.0774 (6.0); 8.0756 (6.1); 7.9493 (1.1); 7.9419 (10.6); 7.9366 (3.6); 7.9251 (3.5); 7.9198 (12.2); 7.9124 (1.2); 7.5512 (6.5); 7.5313 (5.8); 6.1735 (0.5); 6.1562 (2.3); 6.1387 (3.7); 6.1212 (2.4); 6.1036 (0.5); 3.3251 (155.8); 3.0357 (0.4); 2.9717 (0.5); 2.6807 (0.6); 2.6761 (1.3); 2.6716 (1.8); 2.6669 (1.3); 2.6625 (0.6); 2.5251 (5.2); 2.5204 (7.4); 2.5117 (99.5); 2.5072 (205.8); 2.5026 (271.4); 2.4980 (190.4); 2.4934 (88.1); 2.3385 (0.5); 2.3340 (1.2); 2.3294 (1.6); 2.3248 (1.2); 2.3203 (0.5); 1.6717 (14.2); 1.6543 (14.2); 1.3360 (2.0); 1.2985 (1.3); 1.2589 (2.0); 1.2497 (3.1); 1.2346 (1.6); 0.8533 (0.4); 0.1459 (0.6); 0.0080 (4.5); -0.0001 (158.1); -0.0085 (4.9); -0.1496 (0.6) | 480.2 | |
I-066 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2250 (3.1); 9.2076 (3.2); 9.0659 (5.6); 9.0640 (6.1); 9.0604 (6.2); 9.0584 (5.8); 8.5861 (5.3); 8.5806 (5.1); 8.5647 (5.7); 8.5591 (5.7); 8.3163 (0.4); 8.2359 (16.0); 8.0810 (6.4); 8.0791 (6.3); 8.0595 (6.0); 8.0576 (6.0); 7.5872 (2.8); 7.5835 (9.2); 7.5800 (11.4); 7.5760 (9.2); 7.5724 (3.2); 7.4614 (5.0); 7.4568 (8.7); 7.4523 (4.4); 6.0848 (0.5); 6.0675 (2.4); 6.0502 (3.7); 6.0328 (2.4); 6.0155 (0.5); 3.3242 (36.4); 2.6763 (0.7); 2.6717 (0.9); 2.6671 (0.7); 2.5708 (0.4); 2.5470 (0.8); 2.5298 (50.8); 2.5206 (4.3); 2.5118 (52.4); 2.5073 (109.4); 2.5027 (144.4); 2.4981 (101.4); 2.4935 (47.1); 2.3341 (0.6); 2.3295 (0.9); 2.3249 (0.6); 2.0994 (0.3); 1.6256 (14.4); 1.6082 (14.3); 0.1460 (0.3); 0.0080 (2.6); -0.0002 (91.8); -0.0085 (2.8); -0.1495 (0.3) | 399.1 | |
I-067 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6774 (3.2); 9.6602 (3.2); 9.0630 (5.3); 9.0614 (6.2); 9.0576 (5.8); 9.0558 (5.9); 8.5870 (4.9); 8.5814 (4.7); 8.5655 (5.3); 8.5599 (5.3); 8.5151 (4.5); 8.5106 (7.5); 8.5065 (5.5); 8.4460 (6.7); 8.4139 (3.8); 8.4099 (5.9); 8.3161 (0.6); 8.2647 (16.0); 8.0911 (6.0); 8.0894 (6.4); 8.0697 (5.7); 8.0679 (6.0); 6.1496 (0.5); 6.1326 (2.4); 6.1153 (3.8); 6.0980 (2.4); 6.0808 (0.5); 5.7566 (4.7); 3.3258 (147.6); 2.6810 (0.5); 2.6764 (1.0); 2.6719 (1.4); 2.6673 (1.0); 2.6629 (0.5); 2.5254 (4.0); 2.5207 (5.7); 2.5120 (81.0); 2.5075 (169.6); 2.5029 (225.0); 2.4983 (159.0); 2.4938 (74.2); 2.3389 (0.4); 2.3343 (1.0); 2.3297 (1.4); 2.3252 (1.0); 2.3208 (0.5); 1.9894 (0.4); 1.9807 (0.9); 1.9533 (1.0); 1.6627 (14.6); 1.6453 (14.6); 1.3975 (9.3); 0.1459 (0.5); 0.0080 (3.6); -0.0002 (124.3); -0.0086 (3.8); -0.1497 (0.5) | 485.0 | |
I-068 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.6043 (3.3); 9.5928 (3.4); 8.5576 (3.3); 8.5558 (3.5); 8.5495 (3.5); 8.5477 (3.4); 8.4740 (4.6); 8.4712 (7.6); 8.4684 (5.3); 8.4142 (7.2); 8.3881 (6.4); 8.1583 (14.1); 8.0897 (2.1); 8.0866 (2.1); 8.0762 (3.5); 8.0739 (3.5); 8.0636 (2.5); 8.0605 (2.5); 7.8587 (5.6); 7.8451 (5.1); 7.4931 (2.7); 7.4917 (2.8); 7.4836 (3.0); 7.4807 (2.9); 7.4793 (2.8); 7.4726 (2.7); 7.4712 (2.6); 6.0821 (0.5); 6.0703 (2.5); 6.0587 (3.9); 6.0470 (2.6); 6.0353 (0.6); 3.3063 (244.6); 3.2784 (0.8); 2.6156 (1.0); 2.6126 (1.7); 2.6096 (1.0); 2.5217 (1.9); 2.5186 (3.0); 2.5155 (3.1); 2.5065 (146.4); 2.5036 (306.6); 2.5006 (424.4); 2.4976 (327.3); 2.4947 (171.4); 2.3876 (2.4); 2.3846 (3.1); 2.3817 (2.4); 2.3405 (0.4); 2.3235 (0.4); 2.3186 (0.4); 2.0722 (1.4); 1.6560 (15.6); 1.6444 (16.0); 0.0052 (0.4); -0.0001 (14.2); -0.0056 (0.7) | 460.2 | |
I-069 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6468 (1.2); 9.6292 (1.2); 9.1202 (16.0); 8.4897 (1.7); 8.4853 (2.8); 8.4811 (2.1); 8.4255 (2.5); 8.4090 (1.5); 8.4048 (2.2); 8.2121 (5.9); 6.0091 (0.9); 5.9917 (1.4); 5.9742 (0.9); 3.3232 (33.6); 2.6717 (0.4); 2.5252 (1.1); 2.5205 (1.6); 2.5118 (23.1); 2.5073 (47.9); 2.5027 (63.7); 2.4981 (45.3); 2.4935 (21.2); 2.3295 (0.4); 1.6589 (5.5); 1.6415 (5.5); 0.0080 (0.7); -0.0002 (24.6); -0.0085 (0.7) | 495.1 | |
I-070 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3881 (1.1); 9.3731 (1.1); 9.0698 (2.9); 9.0644 (2.8); 8.5862 (2.4); 8.5807 (2.3); 8.5647 (2.6); 8.5592 (2.5); 8.2479 (7.6); 8.0853 (3.1); 8.0837 (3.2); 8.0637 (4.0); 8.0623 (3.8); 8.0599 (2.8); 8.0560 (1.4); 8.0453 (1.2); 8.0416 (2.4); 8.0379 (1.4); 7.9911 (1.6); 7.9862 (2.8); 7.9806 (1.5); 7.9059 (2.6); 7.9014 (3.8); 7.8972 (2.3); 6.1042 (1.0); 6.0869 (1.5); 6.0696 (1.0); 5.7563 (3.0); 3.3264 (66.8); 2.8170 (16.0); 2.6762 (0.4); 2.6717 (0.6); 2.6670 (0.4); 2.5252 (1.7); 2.5205 (2.5); 2.5118 (36.1); 2.5073 (74.1); 2.5027 (96.9); 2.4981 (67.6); 2.4936 (31.2); 2.3341 (0.4); 2.3296 (0.6); 2.3249 (0.4); 1.6436 (7.3); 1.6262 (7.3); 0.0080 (1.7); -0.0002 (53.8); -0.0086 (1.6) | 415.1 | |
I-071 | 1H-NMR(400.2 MHz, CD3CN): δ= 9.1810 (0.4); 8.9657 (1.2); 8.9079 (11.3); 8.8958 (11.5); 8.8800 (0.6); 8.8679 (0.5); 8.0425 (3.0); 8.0377 (6.2); 8.0328 (3.5); 7.9954 (9.7); 7.9799 (3.8); 7.9760 (5.3); 7.9714 (3.1); 7.9463 (0.8); 7.9409 (4.6); 7.9382 (5.5); 7.9256 (1.7); 7.9206 (7.0); 7.9169 (5.2); 7.7594 (0.3); 7.6904 (1.1); 7.6769 (1.1); 7.6421 (0.5); 7.6385 (0.4); 7.6264 (1.2); 7.6233 (0.8); 7.6139 (0.9); 7.6081 (3.5); 7.6027 (1.2); 7.5929 (1.7); 7.5896 (2.9); 7.5865 (1.8); 7.5710 (0.4); 7.5669 (0.3); 7.5490 (4.8); 7.5333 (3.7); 7.5297 (6.9); 7.5160 (1.2); 7.5120 (2.7); 7.4920 (3.6); 7.4799 (7.1); 7.4742 (4.1); 7.4697 (6.4); 7.4679 (5.8); 7.3441 (0.4); 7.3328 (0.6); 6.1430 (0.6); 6.1256 (2.0); 6.1077 (2.9); 6.0899 (2.0); 6.0722 (0.5); 3.4281 (0.7); 3.4106 (0.7); 2.4682 (0.4); 2.4635 (0.6); 2.4589 (0.4); 2.1552 (115.4); 2.1529 (114.8); 2.1194 (0.6); 2.1133 (0.9); 2.1071 (1.3); 2.1009 (0.9); 2.0947 (0.5); 1.9834 (0.4); 1.9717 (1.3); 1.9641 (3.3); 1.9579 (5.2); 1.9522 (72.0); 1.9460 (138.0); 1.9399 (195.7); 1.9337 (133.8); 1.9275 (68.4); 1.9145 (1.0); 1.7806 (0.4); 1.7745 (0.8); 1.7684 (1.1); 1.7622 (0.8); 1.7559 (0.4); 1.6625 (16.0); 1.6541 (1.5); 1.6452 (16.0); 1.3400 (0.5); 1.2850 (0.9); 1.2716 (1.6); 1.2612 (0.9); 1.2428 (0.4); 1.2036 (0.5); 1.1401 (0.9); 1.1225 (1.6); 1.1050 (0.8); 0.8817 (0.4); 0.1458 (2.3); 0.0374 (0.4); 0.0288 (0.6); 0.0215 (0.5); 0.0162 (0.9); 0.0080 (18.7); -0.0002 (537.6); -0.0086 (19.5); -0.1496 (2.4) | 448.0 | |
I-072 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.6186 (3.6); 9.6070 (3.8); 8.9561 (4.8); 8.9549 (4.8); 8.9536 (4.8); 8.4838 (2.9); 8.4799 (3.0); 8.4751 (5.0); 8.4722 (8.6); 8.4695 (8.4); 8.4657 (3.5); 8.4109 (7.3); 8.3960 (4.5); 8.3933 (6.6); 8.2562 (15.4); 8.0904 (5.1); 8.0760 (4.8); 6.1312 (0.6); 6.1197 (2.7); 6.1081 (4.2); 6.0965 (2.7); 6.0849 (0.6); 5.7532 (1.9); 4.0366 (0.4); 4.0249 (0.4); 3.3082 (102.8); 2.6172 (0.4); 2.6142 (0.7); 2.6111 (0.4); 2.5232 (0.9); 2.5201 (1.2); 2.5170 (0.8); 2.5081 (53.2); 2.5052 (115.5); 2.5021 (162.1); 2.4991 (124.1); 2.4962 (63.7); 2.3891 (0.8); 2.3861 (1.2); 2.3831 (0.9); 1.9888 (1.6); 1.6750 (15.6); 1.6634 (16.0); 1.1877 (0.4); 1.1758 (0.9); 1.1639 (0.5); -0.0001 (5.3) | 528.2 | |
I-073 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.6057 (1.8); 9.5940 (1.9); 8.6221 (3.3); 8.6178 (3.5); 8.4785 (2.4); 8.4758 (4.1); 8.4728 (2.8); 8.4192 (3.7); 8.3984 (2.1); 8.3956 (3.3); 8.2032 (2.5); 8.1989 (2.5); 8.1889 (10.6); 8.1843 (2.8); 7.8875 (3.8); 7.8730 (3.4); 6.0136 (1.4); 6.0020 (2.2); 5.9904 (1.4); 3.3077 (55.4); 2.6139 (0.4); 2.5229 (0.4); 2.5198 (0.5); 2.5168 (0.3); 2.5079 (27.2); 2.5049 (60.3); 2.5019 (85.5); 2.4988 (64.6); 2.4958 (32.0); 2.3889 (0.4); 2.3858 (0.6); 2.3828 (0.5); 2.0733 (16.0); 1.6494 (8.2); 1.6377 (8.4); -0.0001 (2.8) | 494.1 | |
I-074 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.6353 (1.1); 9.6239 (1.1); 9.1673 (2.6); 9.1650 (2.7); 8.7548 (2.6); 8.7505 (2.8); 8.6578 (1.9); 8.6554 (2.0); 8.6536 (1.9); 8.6512 (1.8); 8.4782 (1.6); 8.4752 (2.6); 8.4725 (1.9); 8.4252 (2.3); 8.3968 (1.3); 8.3939 (2.0); 8.3913 (1.1); 8.2707 (5.0); 5.9947 (0.9); 5.9831 (1.3); 5.9716 (0.9); 3.3084 (34.8); 2.5231 (0.7); 2.5200 (1.1); 2.5169 (1.2); 2.5081 (15.1); 2.5051 (32.7); 2.5020 (46.5); 2.4989 (35.3); 2.4959 (17.8); 2.3860 (0.3); 2.0735 (16.0); 1.6657 (5.4); 1.6541 (5.5); -0.0001 (2.1) | 461.1 | |
I-075 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6456 (3.2); 9.6282 (3.3); 8.8049 (5.6); 8.8031 (5.7); 8.7923 (5.8); 8.7904 (5.9); 8.4853 (4.4); 8.4810 (7.7); 8.4768 (5.3); 8.4147 (7.0); 8.4085 (5.9); 8.4033 (6.1); 8.3226 (5.7); 8.3196 (8.0); 8.3173 (6.1); 8.2498 (16.0); 7.9649 (5.6); 7.9615 (5.5); 7.9523 (5.4); 7.9489 (5.3); 6.0824 (0.5); 6.0652 (2.3); 6.0478 (3.7); 6.0304 (2.4); 6.0132 (0.5); 3.3235 (90.3); 2.6810 (0.3); 2.6764 (0.7); 2.6718 (1.0); 2.6673 (0.7); 2.6628 (0.3); 2.5253 (2.6); 2.5206 (4.0); 2.5119 (57.7); 2.5074 (118.8); 2.5029 (156.9); 2.4983 (111.0); 2.4937 (52.0); 2.3343 (0.7); 2.3297 (1.0); 2.3251 (0.7); 1.9893 (1.2); 1.6591 (14.3); 1.6417 (14.2); 1.3976 (15.5); 1.1934 (0.3); 1.1755 (0.7); 1.1577 (0.3); 0.0080 (1.7); -0.0002 (56.1); -0.0085 (1.6) | 485.2 | |
I-076 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5510 (1.8); 9.5327 (1.8); 8.5224 (3.8); 8.5090 (3.9); 8.3969 (3.2); 8.3931 (2.2); 8.3606 (2.7); 8.3567 (4.4); 8.3520 (2.7); 8.3330 (2.5); 8.3297 (3.7); 8.3155 (0.4); 8.2688 (8.8); 7.8128 (4.0); 7.8089 (4.2); 7.7049 (2.9); 7.7003 (2.6); 7.6914 (2.8); 7.6868 (2.6); 5.6247 (1.2); 5.6073 (1.9); 5.5898 (1.2); 4.0559 (1.2); 4.0381 (3.6); 4.0203 (3.6); 4.0025 (1.2); 3.3222 (60.4); 2.6757 (0.6); 2.6711 (0.9); 2.6665 (0.7); 2.5247 (2.3); 2.5200 (3.5); 2.5113 (51.8); 2.5068 (107.1); 2.5022 (141.6); 2.4976 (100.1); 2.4931 (46.6); 2.3336 (0.6); 2.3291 (0.9); 2.3244 (0.6); 1.9889 (16.0); 1.6421 (7.8); 1.6251 (7.8); 1.3978 (1.6); 1.2360 (0.4); 1.1931 (4.4); 1.1804 (0.3); 1.1753 (8.7); 1.1575 (4.2); 0.0080 (1.6); -0.0002 (55.1); -0.0086 (1.6) | 494.1 | |
I-077 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.7257 (3.3); 9.7091 (3.4); 8.5515 (4.7); 8.5472 (7.8); 8.5430 (5.9); 8.5010 (7.1); 8.4274 (3.7); 8.4233 (6.2); 8.3161 (0.5); 8.2178 (16.0); 7.7943 (8.5); 7.7856 (14.3); 7.7612 (14.7); 7.7525 (8.7); 6.1087 (0.5); 6.0915 (2.5); 6.0743 (3.9); 6.0571 (2.6); 6.0397 (0.5); 3.3232 (68.2); 2.6807 (0.4); 2.6762 (0.9); 2.6717 (1.3); 2.6671 (0.9); 2.6626 (0.4); 2.5252 (3.0); 2.5205 (4.4); 2.5117 (71.3); 2.5073 (149.2); 2.5027 (198.4); 2.4981 (141.2); 2.4936 (66.6); 2.3387 (0.4); 2.3341 (0.9); 2.3295 (1.2); 2.3249 (0.9); 2.3205 (0.4); 2.0752 (2.4); 1.6520 (15.9); 1.6345 (15.8); 1.2591 (0.3); 1.2341 (0.5); 0.0081 (0.5); -0.0001 (16.4); -0.0084 (0.5) | 466.1 | |
I-078 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5493 (3.2); 9.5313 (3.2); 8.6193 (0.4); 8.5642 (0.5); 8.5162 (8.3); 8.5099 (9.0); 8.4091 (5.9); 8.4053 (4.0); 8.3761 (5.3); 8.3721 (7.8); 8.3675 (4.7); 8.3281 (7.5); 8.3241 (5.2); 8.3157 (1.3); 8.3089 (2.4); 8.3060 (2.3); 8.3027 (2.3); 8.2998 (1.9); 8.2850 (1.9); 8.2787 (1.6); 8.2371 (16.0); 5.4058 (0.5); 5.3883 (2.4); 5.3707 (3.8); 5.3529 (2.4); 5.3355 (0.5); 3.3234 (271.5); 2.6800 (0.8); 2.6756 (1.8); 2.6711 (2.5); 2.6664 (1.8); 2.6619 (0.8); 2.5246 (6.2); 2.5199 (9.0); 2.5112 (141.5); 2.5067 (293.3); 2.5021 (388.8); 2.4975 (273.9); 2.4929 (126.9); 2.3380 (0.8); 2.3335 (1.7); 2.3289 (2.4); 2.3243 (1.7); 2.3199 (0.8); 2.0745 (7.4); 1.6426 (14.8); 1.6251 (14.8); 1.4350 (0.5); 1.4171 (0.5); 0.0081 (0.7); -0.0001 (26.3); -0.0085 (0.7) | 496.1 | |
I-079 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5519 (3.1); 9.5339 (3.2); 8.5087 (8.7); 8.5035 (10.0); 8.4467 (4.3); 8.4415 (3.6); 8.4233 (4.3); 8.4180 (4.1); 8.4096 (5.8); 8.3657 (4.7); 8.3616 (7.6); 8.3570 (5.1); 8.3390 (4.5); 8.3354 (6.7); 8.3156 (1.4); 8.2516 (16.0); 5.4506 (0.5); 5.4335 (2.4); 5.4158 (3.7); 5.3981 (2.4); 5.3805 (0.5); 4.0377 (0.6); 4.0200 (0.6); 3.3232 (263.4); 2.6800 (0.9); 2.6755 (1.9); 2.6709 (2.6); 2.6663 (1.9); 2.6617 (0.9); 2.5244 (6.6); 2.5197 (9.6); 2.5110 (145.7); 2.5065 (303.8); 2.5019 (404.0); 2.4973 (286.2); 2.4927 (133.8); 2.3378 (0.8); 2.3334 (1.8); 2.3287 (2.5); 2.3241 (1.8); 2.3195 (0.8); 2.0744 (2.7); 1.9888 (2.5); 1.6493 (14.5); 1.6318 (14.6); 1.2340 (0.6); 1.1928 (0.7); 1.1750 (1.4); 1.1572 (0.7); 0.0080 (0.7); -0.0002 (26.8); -0.0086 (0.8) | 512.1 | |
I-080 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5049 (0.6); 9.4870 (0.6); 8.9869 (3.8); 8.9747 (3.9); 8.2534 (0.9); 8.2492 (1.3); 8.2448 (0.9); 8.1757 (2.9); 8.1292 (0.9); 8.1254 (1.7); 8.1215 (0.9); 7.9579 (0.9); 7.9535 (1.4); 7.9490 (0.8); 7.6312 (1.0); 7.6190 (2.0); 7.6069 (1.0); 6.0260 (0.4); 6.0085 (0.7); 5.9909 (0.5); 5.7560 (1.3); 3.3309 (33.8); 2.5255 (0.5); 2.5207 (0.8); 2.5120 (13.2); 2.5075 (27.2); 2.5030 (35.6); 2.4984 (25.0); 2.4938 (11.6); 1.6564 (2.7); 1.6390 (2.7); 1.2480 (16.0); -0.0002 (9.7) | 449.1 | |
I-081 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4744 (3.3); 9.4571 (3.4); 8.3420 (3.9); 8.3229 (5.5); 8.3211 (6.0); 8.3155 (0.9); 8.3021 (6.5); 8.2739 (4.8); 8.2701 (9.4); 8.2663 (5.4); 8.2449 (16.0); 8.2040 (6.3); 8.2020 (7.1); 8.1830 (9.6); 8.1809 (7.7); 8.1784 (8.4); 8.1743 (5.5); 8.1445 (6.8); 8.1415 (8.6); 8.1366 (8.2); 8.1321 (4.4); 8.1257 (5.4); 8.1237 (5.0); 5.9855 (0.5); 5.9684 (2.5); 5.9511 (4.0); 5.9338 (2.5); 5.9165 (0.5); 5.7560 (6.0); 3.3248 (99.6); 3.3118 (42.2); 2.6762 (0.7); 2.6716 (1.0); 2.6671 (0.7); 2.5251 (2.5); 2.5204 (3.7); 2.5117 (55.2); 2.5072 (114.3); 2.5027 (151.0); 2.4981 (106.4); 2.4935 (49.2); 2.3340 (0.7); 2.3295 (0.9); 2.3249 (0.7); 1.6788 (15.3); 1.6615 (15.2); 0.0080 (0.3); -0.0001 (11.0) | 431.1 | |
I-082 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4147 (3.8); 9.3971 (3.8); 9.1006 (8.5); 9.0951 (8.7); 9.0886 (6.5); 9.0870 (7.0); 9.0832 (6.6); 9.0816 (6.3); 8.9736 (8.5); 8.9686 (8.5); 8.5900 (5.0); 8.5844 (4.8); 8.5685 (5.3); 8.5629 (5.2); 8.4941 (4.7); 8.4888 (8.1); 8.4835 (4.4); 8.3161 (0.7); 8.2604 (16.0); 8.0997 (6.7); 8.0982 (6.8); 8.0782 (6.2); 8.0767 (6.3); 8.0477 (6.8); 8.0274 (9.2); 7.9143 (9.5); 7.8936 (7.0); 6.1784 (0.6); 6.1611 (2.6); 6.1436 (4.2); 6.1262 (2.7); 6.1094 (0.5); 3.3238 (125.2); 2.6757 (1.4); 2.6713 (1.9); 2.6668 (1.4); 2.5246 (6.6); 2.5112 (117.5); 2.5069 (230.6); 2.5024 (298.0); 2.4979 (215.5); 2.4935 (105.1); 2.3337 (1.4); 2.3292 (1.8); 2.3248 (1.4); 2.0750 (0.5); 1.6779 (15.8); 1.6605 (15.8); 0.0079 (0.6); -0.0002 (16.5); -0.0084 (0.6) | 464.2 | |
I-083 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3856 (4.4); 9.3682 (4.4); 9.0832 (7.7); 9.0349 (8.1); 9.0307 (8.0); 8.9183 (8.4); 8.5872 (4.2); 8.5825 (4.2); 8.5656 (4.6); 8.5613 (4.4); 8.4226 (7.9); 8.3157 (0.7); 8.2561 (12.0); 8.0957 (6.4); 8.0744 (5.9); 7.8510 (10.0); 7.8300 (11.6); 7.6167 (11.8); 7.5958 (9.9); 7.5310 (0.6); 7.5138 (0.4); 6.1529 (2.9); 6.1353 (4.2); 6.1178 (2.8); 6.1013 (0.8); 3.4202 (0.4); 3.3234 (199.9); 3.2527 (0.5); 2.7465 (0.4); 2.6714 (3.5); 2.5022 (490.5); 2.3293 (3.2); 2.0743 (0.6); 1.6720 (16.0); 1.6547 (15.9); 1.2319 (0.3); -0.0002 (14.0) | 430.2 | |
I-084 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3751 (3.8); 9.3576 (3.8); 9.0843 (6.8); 9.0805 (6.5); 9.0789 (6.4); 9.0136 (8.2); 9.0080 (8.3); 8.9025 (8.4); 8.8975 (8.4); 8.5878 (4.8); 8.5823 (4.7); 8.5663 (5.2); 8.5608 (5.1); 8.4056 (4.7); 8.4003 (8.1); 8.3950 (4.5); 8.3157 (0.8); 8.2558 (15.5); 8.0970 (6.5); 8.0956 (6.8); 8.0756 (6.0); 8.0741 (6.3); 7.8704 (5.6); 7.8652 (2.7); 7.8570 (6.3); 7.8484 (6.8); 7.8402 (2.8); 7.8349 (6.1); 7.4032 (6.2); 7.3981 (2.2); 7.3810 (11.6); 7.3640 (2.0); 7.3588 (5.6); 6.1690 (0.7); 6.1519 (2.7); 6.1346 (4.2); 6.1171 (2.7); 6.0995 (0.6); 3.3241 (224.5); 2.6754 (1.8); 2.6710 (2.4); 2.6667 (1.8); 2.5409 (2.0); 2.5242 (9.1); 2.5108 (146.3); 2.5066 (282.9); 2.5021 (365.7); 2.4976 (267.2); 2.4934 (133.2); 2.3334 (1.7); 2.3289 (2.3); 2.3245 (1.7); 1.6710 (16.0); 1.6536 (16.0); 0.0077 (0.8); -0.0002 (19.0); -0.0084 (0.8) | 414.3 | |
I-085 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0269 (5.9); 8.9974 (1.0); 8.8686 (15.6); 8.8565 (16.0); 8.3156 (0.8); 8.0949 (4.0); 8.0905 (6.7); 8.0861 (4.1); 8.0329 (14.8); 7.8502 (4.4); 7.8464 (7.8); 7.8426 (4.4); 7.6894 (4.5); 7.6851 (6.5); 7.6808 (4.2); 7.5489 (4.1); 7.5367 (7.8); 7.5245 (3.9); 7.3747 (0.4); 5.7560 (0.6); 3.4093 (0.8); 3.3918 (2.2); 3.3744 (2.3); 3.3568 (1.1); 3.3535 (0.8); 3.3227 (171.9); 3.2950 (35.1); 2.6752 (1.7); 2.6707 (2.4); 2.6662 (1.8); 2.5241 (6.9); 2.5193 (10.7); 2.5107 (140.1); 2.5063 (282.2); 2.5018 (368.0); 2.4972 (262.8); 2.4927 (125.2); 2.3377 (0.8); 2.3331 (1.6); 2.3286 (2.3); 2.3240 (1.6); 1.7037 (2.4); 1.6909 (6.0); 1.6834 (6.5); 1.6717 (2.7); 1.4140 (1.1); 1.4053 (3.9); 1.3937 (10.1); 1.3860 (13.8); 1.3739 (4.8); 1.3365 (0.4); 1.1086 (2.2); 1.0911 (4.7); 1.0777 (1.7); 1.0736 (3.0); 1.0582 (0.6); 0.0081 (1.9); -0.0001 (59.2); -0.0084 (2.0) | 419.2 | |
I-086 | 1H-NMR(400.2 MHz, CD3CN): δ= 8.8793 (0.3); 8.8686 (12.1); 8.8564 (12.2); 8.2603 (1.3); 7.9799 (9.6); 7.7932 (0.6); 7.7881 (4.5); 7.7854 (5.4); 7.7823 (2.6); 7.7724 (1.7); 7.7674 (7.1); 7.7639 (5.4); 7.6384 (0.7); 7.6353 (1.4); 7.6322 (0.9); 7.6218 (1.0); 7.6167 (3.6); 7.6120 (1.3); 7.6012 (1.8); 7.5981 (3.1); 7.5949 (1.9); 7.5818 (1.0); 7.5646 (1.0); 7.5390 (1.0); 7.5343 (4.8); 7.5304 (2.2); 7.5175 (3.7); 7.5144 (6.6); 7.5003 (1.2); 7.4960 (2.6); 7.4942 (2.0); 7.4636 (3.7); 7.4515 (7.0); 7.4393 (3.5); 7.4192 (3.2); 7.4150 (5.5); 7.4110 (3.8); 7.3421 (3.7); 7.3372 (5.2); 7.3333 (4.1); 7.2748 (4.1); 7.2698 (6.7); 7.2649 (3.4); 6.0844 (0.5); 6.0670 (2.0); 6.0492 (2.9); 6.0313 (2.0); 6.0138 (0.5); 5.4471 (1.5); 4.0857 (1.0); 4.0679 (3.0); 4.0500 (3.0); 4.0322 (1.0); 2.6381 (1.0); 2.1526 (22.8); 2.1078 (0.4); 1.9721 (13.5); 1.9648 (1.0); 1.9585 (1.6); 1.9528 (20.1); 1.9467 (38.3); 1.9405 (54.8); 1.9343 (37.3); 1.9281 (19.0); 1.8480 (0.6); 1.7689 (0.3); 1.6232 (16.0); 1.6059 (15.9); 1.3720 (0.5); 1.2845 (0.5); 1.2760 (1.4); 1.2697 (1.5); 1.2214 (3.8); 1.2036 (7.6); 1.1857 (3.7); 0.8808 (0.4); 0.1457 (0.8); 0.0079 (6.8); -0.0002 (180.8); -0.0087 (5.7); -0.1497 (0.7) | 484.1 | |
I-087 | 1H-NMR(400.2 MHz, CD3CN): δ= 14.8224 (0.4); 11.6690 (0.5); 8.8990 (10.6); 8.8869 (10.6); 8.5569 (1.2); 8.5416 (0.8); 8.5136 (0.4); 7.9858 (8.6); 7.9087 (0.6); 7.8630 (2.6); 7.8585 (4.3); 7.8534 (2.7); 7.8100 (0.6); 7.7226 (4.4); 7.6443 (1.2); 7.6195 (1.3); 7.5874 (0.8); 7.5090 (0.7); 7.4862 (3.6); 7.4740 (6.1); 7.4617 (3.0); 7.3898 (4.8); 6.1182 (0.5); 6.1008 (2.1); 6.0830 (3.0); 6.0650 (2.1); 6.0485 (0.8); 4.4684 (0.4); 4.4302 (0.5); 3.6567 (0.4); 3.6409 (0.5); 3.1285 (0.6); 3.1111 (0.6); 2.8890 (1.6); 2.7715 (1.4); 2.7280 (16.0); 2.4695 (1.9); 2.4648 (2.9); 2.4600 (2.0); 2.3217 (0.5); 2.3103 (0.6); 2.2804 (0.5); 2.2496 (0.9); 2.2295 (1.0); 2.1600 (581.7); 2.1199 (3.4); 2.1136 (4.1); 2.1074 (4.6); 2.1013 (3.1); 2.0950 (2.1); 2.0771 (5.2); 2.0649 (35.3); 2.0064 (0.7); 1.9926 (0.8); 1.9643 (18.8); 1.9525 (231.1); 1.9464 (426.8); 1.9402 (590.8); 1.9340 (400.7); 1.9279 (204.2); 1.9064 (1.4); 1.8844 (0.7); 1.7972 (0.9); 1.7810 (1.3); 1.7749 (2.4); 1.7686 (3.4); 1.7626 (2.3); 1.7562 (1.2); 1.6454 (14.9); 1.6281 (15.0); 1.6151 (0.6); 1.5984 (0.7); 1.5102 (0.5); 1.4969 (0.5); 1.4908 (0.6); 1.4085 (1.7); 1.4012 (0.6); 1.3906 (1.7); 1.3508 (1.3); 1.3319 (3.9); 1.3137 (3.9); 1.2708 (5.9); 1.1996 (1.0); 1.1662 (0.5); 1.1585 (0.6); 1.1482 (0.5); 1.1321 (0.6); 1.1266 (0.5); 1.1101 (0.6); 1.0841 (0.5); 1.0272 (0.5); 0.9282 (0.6); 0.8815 (1.5); 0.8567 (1.2); 0.8405 (1.1); 0.8120 (0.5); 0.1546 (0.8); 0.1457 (7.9); 0.0530 (0.5); 0.0302 (2.4); 0.0080 (107.4); -0.0002 (1799.6); -0.0086 (72.7); -0.0388 (1.7); -0.0702 (0.7); -0.1025 (0.6); -0.1076 (0.8); -0.1498 (8.2); -2.3548 (0.5); -3.0454 (0.4) | 386.2 | |
I-088 | 1H-NMR(400.2 MHz, CD3CN): δ= 8.8936 (10.7); 8.8814 (10.8); 8.7707 (1.9); 7.9883 (9.0); 7.8620 (3.2); 7.8575 (5.5); 7.8532 (3.4); 7.7568 (4.0); 7.7530 (5.6); 7.7490 (3.5); 7.6709 (1.3); 7.6541 (1.4); 7.4810 (3.1); 7.4689 (5.9); 7.4568 (3.0); 7.3811 (3.8); 7.3771 (5.8); 7.3732 (3.7); 6.1231 (0.6); 6.1057 (2.1); 6.0877 (3.1); 6.0699 (2.1); 6.0523 (0.6); 5.4479 (3.4); 4.0859 (1.3); 4.0681 (4.0); 4.0503 (4.0); 4.0324 (1.4); 2.1673 (21.4); 2.1222 (0.3); 2.1152 (0.3); 2.1085 (0.3); 1.9726 (17.1); 1.9536 (11.3); 1.9475 (20.9); 1.9414 (28.7); 1.9352 (20.4); 1.9291 (11.2); 1.6774 (0.8); 1.6659 (1.6); 1.6576 (2.0); 1.6415 (16.0); 1.6243 (15.8); 1.2695 (1.2); 1.2216 (4.5); 1.2038 (8.7); 1.1860 (4.4); 0.9238 (1.3); 0.9184 (1.5); 0.9123 (4.0); 0.9052 (6.3); 0.9011 (4.4); 0.8975 (4.2); 0.8939 (5.2); 0.8861 (2.7); 0.8633 (1.2); 0.8495 (2.7); 0.8419 (5.1); 0.8345 (3.4); 0.8298 (3.3); 0.8223 (5.5); 0.8150 (3.1); 0.8103 (1.7); 0.8037 (1.3); 0.1459 (0.4); -0.0002 (83.7); -0.0079 (7.0); -0.1496 (0.5) | 412.2 | |
I-089 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4896 (3.1); 9.4721 (3.2); 8.9998 (4.1); 8.9981 (4.0); 8.9962 (4.1); 8.9939 (4.2); 8.5081 (2.5); 8.5021 (2.4); 8.4865 (2.8); 8.4804 (2.7); 8.2800 (4.7); 8.2761 (9.3); 8.2723 (5.4); 8.2467 (16.0); 8.1721 (4.1); 8.1673 (7.7); 8.1634 (5.6); 8.1461 (5.9); 8.1416 (7.8); 8.1372 (4.0); 8.1075 (4.7); 8.0860 (4.3); 6.1477 (0.5); 6.1305 (2.3); 6.1131 (3.6); 6.0956 (2.3); 6.0782 (0.5); 4.0565 (0.5); 4.0387 (1.6); 4.0209 (1.7); 4.0031 (0.6); 3.3462 (0.4); 3.3264 (57.0); 3.3162 (40.1); 2.6772 (0.5); 2.6726 (0.7); 2.6681 (0.5); 2.5261 (1.9); 2.5215 (2.7); 2.5127 (38.2); 2.5082 (79.2); 2.5037 (104.2); 2.4990 (72.8); 2.4944 (33.7); 2.3350 (0.4); 2.3305 (0.6); 2.3259 (0.4); 1.9898 (7.4); 1.6661 (13.9); 1.6487 (13.8); 1.3972 (0.7); 1.2352 (0.4); 1.1936 (2.0); 1.1758 (4.1); 1.1580 (2.0); 0.0080 (1.6); -0.0002 (52.5); -0.0086 (1.5) | 474.2 | |
I-090 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5110 (3.8); 9.4938 (3.8); 8.6856 (7.4); 8.6794 (7.4); 8.3161 (0.6); 8.2686 (5.1); 8.2621 (4.9); 8.2468 (6.0); 8.2398 (8.5); 8.2350 (10.4); 8.2312 (6.1); 8.1564 (4.8); 8.1518 (9.1); 8.1476 (5.8); 8.1250 (6.4); 8.1209 (8.5); 8.1165 (4.6); 7.9432 (8.0); 7.9214 (7.0); 5.9748 (0.6); 5.9575 (2.9); 5.9402 (4.6); 5.9229 (2.9); 5.9054 (0.6); 3.3263 (90.8); 3.3177 (45.7); 2.6814 (0.3); 2.6772 (0.7); 2.6726 (0.9); 2.6679 (0.7); 2.6635 (0.3); 2.5260 (3.0); 2.5212 (4.6); 2.5126 (55.6); 2.5081 (112.0); 2.5036 (145.2); 2.4990 (102.5); 2.4945 (48.3); 2.3348 (0.6); 2.3303 (0.9); 2.3258 (0.6); 2.0758 (5.0); 1.6816 (16.0); 1.6641 (15.9); 0.0080 (2.3); -0.0002 (67.4); -0.0085 (2.1) | 508.2 | |
I-091 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5384 (2.5); 9.5211 (2.5); 9.0504 (15.7); 9.0382 (16.0); 8.2236 (3.7); 8.2198 (6.9); 8.2160 (4.1); 8.1494 (3.1); 8.1447 (6.5); 8.1405 (4.6); 8.1315 (5.0); 8.1276 (5.6); 8.1229 (2.7); 7.9534 (0.5); 7.7417 (4.2); 7.7296 (7.9); 7.7174 (4.0); 6.0691 (0.4); 6.0519 (2.0); 6.0346 (3.1); 6.0172 (2.0); 6.0000 (0.4); 3.3250 (61.7); 3.3136 (31.1); 2.8918 (4.0); 2.7329 (3.2); 2.7317 (3.2); 2.6765 (0.6); 2.6719 (0.8); 2.6674 (0.6); 2.5255 (2.8); 2.5207 (4.7); 2.5121 (52.3); 2.5076 (103.6); 2.5030 (132.7); 2.4984 (92.5); 2.4939 (42.8); 2.3344 (0.6); 2.3298 (0.8); 2.3252 (0.6); 2.0868 (0.5); 1.7044 (10.7); 1.6870 (10.6); 1.3976 (3.1); 1.1198 (0.3); 0.0080 (2.6); -0.0002 (69.9); -0.0085 (2.1) | 475.2 | |
I-092 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3542 (2.8); 9.3362 (2.8); 8.9979 (15.7); 8.9858 (16.0); 8.3159 (0.5); 8.1720 (7.2); 8.1703 (8.5); 8.1254 (1.8); 8.1217 (3.4); 8.1180 (2.0); 8.1003 (2.3); 8.0967 (4.4); 8.0929 (2.6); 8.0138 (3.2); 8.0095 (6.2); 8.0056 (4.3); 7.9904 (5.2); 7.9863 (6.7); 7.9818 (3.4); 7.6429 (3.8); 7.6307 (7.3); 7.6185 (3.7); 6.0446 (0.4); 6.0271 (1.5); 6.0095 (2.3); 5.9919 (1.5); 5.9761 (0.3); 5.7560 (10.1); 4.3046 (0.6); 4.2935 (0.7); 4.2836 (0.5); 4.2777 (0.8); 4.2682 (1.5); 4.2568 (1.2); 4.2415 (1.8); 4.2300 (1.2); 4.2219 (1.3); 4.2158 (1.7); 4.2033 (0.6); 4.1955 (1.3); 4.1898 (1.6); 4.1799 (0.7); 4.1691 (0.5); 4.1632 (0.6); 4.1595 (0.6); 4.1537 (0.7); 3.3235 (114.1); 2.6799 (0.5); 2.6755 (1.1); 2.6710 (1.5); 2.6665 (1.1); 2.6620 (0.5); 2.5245 (4.7); 2.5198 (7.2); 2.5111 (89.7); 2.5066 (182.0); 2.5021 (236.9); 2.4975 (168.0); 2.4930 (79.6); 2.3380 (0.5); 2.3334 (1.0); 2.3289 (1.4); 2.3243 (1.0); 2.3200 (0.5); 1.7537 (0.4); 1.6526 (12.3); 1.6352 (12.3); 0.1459 (0.8); 0.0079 (6.9); -0.0001 (202.2); -0.0085 (6.7); -0.0177 (0.3); -0.1496 (0.8) | 459.1 | |
I-093 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4914 (2.6); 9.4736 (2.7); 8.9966 (15.7); 8.9844 (16.0); 8.2729 (3.3); 8.2691 (6.9); 8.2653 (4.7); 8.2523 (4.2); 8.2477 (6.2); 8.2438 (3.6); 8.1783 (12.4); 8.1650 (4.0); 8.1605 (6.4); 8.1561 (3.4); 7.6394 (4.3); 7.6273 (8.1); 7.6151 (4.1); 6.0510 (0.4); 6.0335 (2.0); 6.0160 (3.1); 5.9985 (2.0); 5.9809 (0.4); 5.7566 (6.8); 5.1388 (1.6); 5.1143 (4.9); 5.0896 (5.2); 5.0649 (1.8); 3.3244 (36.1); 2.6763 (0.6); 2.6717 (0.8); 2.6671 (0.6); 2.5251 (2.9); 2.5204 (4.7); 2.5117 (49.4); 2.5073 (99.4); 2.5027 (129.4); 2.4981 (92.0); 2.4936 (43.5); 2.3563 (1.0); 2.3341 (0.6); 2.3295 (0.8); 2.3250 (0.6); 1.7547 (0.8); 1.6591 (12.0); 1.6417 (11.9); 1.2400 (0.4); 0.1457 (0.4); 0.0078 (3.4); -0.0003 (91.7); -0.0086 (3.0); -0.1497 (0.3) | 475.1 | |
I-094 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3506 (2.5); 9.3326 (2.5); 8.9994 (15.6); 8.9872 (16.0); 8.8459 (3.0); 8.8437 (3.4); 8.8395 (3.4); 8.8373 (3.1); 8.3158 (0.8); 8.1928 (2.8); 8.1878 (5.2); 8.1841 (4.4); 8.1715 (15.7); 8.1662 (6.6); 8.1613 (2.9); 7.8499 (3.9); 7.8458 (5.9); 7.8418 (3.8); 7.6402 (4.2); 7.6280 (8.1); 7.6159 (4.1); 7.4098 (0.6); 7.4017 (0.4); 7.3961 (0.4); 7.3870 (0.6); 7.1097 (4.4); 7.1033 (4.4); 6.9934 (2.1); 6.0421 (0.4); 6.0248 (1.8); 6.0072 (2.9); 5.9897 (1.9); 5.9722 (0.4); 5.7559 (2.9); 3.3218 (77.2); 2.6800 (0.6); 2.6755 (1.4); 2.6709 (1.9); 2.6663 (1.4); 2.6619 (0.6); 2.5412 (0.7); 2.5244 (4.8); 2.5197 (7.1); 2.5110 (106.0); 2.5065 (219.5); 2.5020 (291.6); 2.4974 (207.3); 2.4928 (97.4); 2.4521 (0.6); 2.4355 (0.4); 2.3378 (0.6); 2.3334 (1.3); 2.3288 (1.8); 2.3242 (1.3); 2.3197 (0.6); 1.6603 (11.2); 1.6429 (11.2); 1.2568 (3.8); 1.2395 (3.8); 1.1613 (2.4); 1.1443 (2.3); 1.1069 (8.0); 1.0785 (8.1); 0.9143 (2.4); 0.8976 (2.3); 0.1458 (0.4); 0.0079 (2.7); -0.0002 (89.6); -0.0086 (2.7); -0.1495 (0.3) | 461.2 # | |
I-095 | 1H-NMR(600.1 MHz, CD3CN): δ= 9.2056 (5.4); 8.1732 (3.2); 8.0710 (2.9); 8.0509 (4.0); 8.0484 (3.8); 7.8814 (0.7); 7.8702 (0.7); 6.2048 (0.8); 6.1932 (1.2); 6.1815 (0.8); 3.2758 (1.6); 3.1333 (0.8); 3.1168 (1.0); 3.1009 (16.0); 2.1346 (2.2); 2.1281 (2.4); 2.0727 (0.8); 2.0543 (0.3); 2.0503 (0.5); 2.0463 (0.3); 1.9638 (1.8); 1.9556 (1.7); 1.9477 (17.5); 1.9436 (31.9); 1.9395 (46.0); 1.9354 (32.3); 1.9313 (16.8); 1.6943 (6.4); 1.6828 (6.4); 1.2703 (0.5); 1.2328 (0.4); 1.2219 (0.4); 1.1391 (0.4); 0.0052 (1.9); -0.0001 (41.5); -0.0053 (2.2) | 474.9 | |
I-096 | 1H-NMR(600.1 MHz, d 6-DMSO): δ= 9.43 (d, 1H), 8.81 (d, 2H), 8.21 (m,. 1H), 8.14 (m, 1H), 8.13 (m, 2H), 5.94 (m, 1H), 3.31 (s, 3H), 2.32 ( s, 3H), 1.63 (d, 3H) | 421.0 | |
I-097 | 1H-NMR(600.1 MHz, d 6-DMSO): δ= 9.65 (d, 1H), 9.41 (m, 2H), 8.49 (m, 1H), 8.42 (s, 1H), 8.41 (s, 1H), 8.27 (s, 1H), 6.09 (m, 1H), 1.67 (d, 3H) | 528.9 | |
I-098 | 1H-NMR(600.1 MHz, d 6-DMSO): δ= 9.4562 (4.1); 8.9168 (0.9); 8.9049 (0.9); 8.2334 (3.2); 8.0092 (2.0); 8.0064 (2.1); 7.4498 (2.1); 7.4470 (2.2); 6.0021 (0.6); 5.9904 (1.0); 5.9787 (0.6); 3.3324 (16.0); 2.5230 (0.5); 2.5200 (0.7); 2.5169 (0.7); 2.5050 (23.5); 2.5020 (32.1); 2.4991 (24.6); 2.0744 (2.8); 1.6188 (3.8); 1.6071 (3.8) | 402.9 | |
I-099 | 1H-NMR(600.1 MHz, CD3CN): δ= 8.7011 (6.6); 8.2650 (1.5); 8.2625 (4.2); 8.2594 (6.0); 8.1932 (1.7); 8.1905 (2.7); 8.0383 (0.8); 8.0264 (0.8); 7.9730 (6.1); 6.1091 (0.3); 6.0974 (1.3); 6.0856 (2.0); 6.0737 (1.4); 6.0620 (0.4); 4.6786 (0.3); 4.0664 (0.4); 4.0545 (0.4); 2.3485 (16.0); 2.2392 (0.5); 2.2385 (0.5); 2.2059 (2.2); 2.1777 (0.8); 1.9735 (2.1); 1.9674 (13.1); 1.9593 (0.4); 1.9551 (0.4); 1.9513 (2.9); 1.9472 (5.4); 1.9431 (7.7); 1.9390 (5.3); 1.9349 (2.6); 1.6725 (9.8); 1.6610 (9.8); 1.3730 (0.6); 1.2764 (0.9); 1.2685 (0.5); 1.2164 (0.6); 1.2046 (1.1); 1.1927 (0.5) | 475.0 | |
I-100 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0012 (12.6); 8.9974 (2.1); 8.9890 (12.9); 8.9853 (2.0); 8.7704 (1.8); 8.7516 (1.9); 8.3136 (0.8); 8.1575 (9.9); 8.1134 (0.9); 7.6525 (0.4); 7.6467 (3.5); 7.6404 (0.8); 7.6346 (6.6); 7.6284 (0.5); 7.6224 (3.4); 7.3785 (0.6); 7.2129 (6.2); 6.0251 (0.4); 6.0074 (1.6); 5.9894 (2.3); 5.9714 (1.6); 5.9540 (0.4); 4.4016 (0.4); 4.0650 (0.4); 4.0519 (1.6); 4.0140 (16.0); 4.0128 (16.0); 3.8869 (0.7); 3.8790 (0.7); 3.7244 (0.4); 3.7128 (0.4); 3.7021 (0.4); 3.3267 (146.0); 2.6811 (0.4); 2.6764 (0.8); 2.6718 (1.1); 2.6674 (0.8); 2.6627 (0.4); 2.5422 (3.8); 2.5254 (3.4); 2.5207 (5.1); 2.5120 (67.0); 2.5075 (137.1); 2.5029 (181.2); 2.4983 (132.9); 2.4938 (65.2); 2.3388 (0.4); 2.3343 (0.8); 2.3297 (1.1); 2.3252 (0.8); 2.0740 (0.5); 1.5915 (10.4); 1.5743 (10.4); 1.4824 (1.0); 1.4651 (1.0); 0.0080 (0.4); -0.0002 (14.6); -0.0085 (0.5) | 367.1 | |
I-101 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 17.0545 (0.3); 9.6374 (2.5); 9.6192 (2.6); 9.0034 (13.0); 8.9913 (13.5); 8.9777 (0.4); 8.7807 (0.3); 8.6946 (0.6); 8.6707 (0.7); 8.6592 (0.8); 8.6290 (1.2); 8.5946 (12.8); 8.5905 (13.4); 8.5135 (4.0); 8.5095 (6.5); 8.5054 (3.1); 8.4092 (0.5); 8.4052 (0.8); 8.3125 (12.6); 8.3029 (0.8); 8.2986 (0.7); 8.2835 (1.0); 8.2790 (0.9); 8.1863 (11.2); 7.9766 (0.4); 7.9572 (0.6); 7.8685 (0.4); 7.8577 (0.4); 7.6451 (3.7); 7.6330 (6.9); 7.6209 (3.4); 7.1990 (0.4); 7.0711 (0.3); 6.9445 (0.4); 6.7796 (0.5); 6.0950 (0.4); 6.0788 (1.9); 6.0609 (2.7); 6.0433 (1.8); 3.8041 (0.4); 3.7490 (0.4); 3.7027 (0.4); 3.6812 (0.4); 3.6508 (0.4); 3.6138 (0.4); 3.5784 (0.4); 3.5317 (0.6); 3.5121 (0.5); 3.4710 (0.6); 3.4299 (1.2); 3.4204 (1.9); 3.4063 (1.4); 3.3875 (6.3); 3.3603 (56.3); 3.3407 (17.0); 3.3241 (1850.4); 3.2543 (0.4); 3.2405 (0.4); 3.1852 (0.4); 3.0433 (0.5); 3.0239 (0.9); 2.9943 (0.4); 2.9592 (0.4); 2.9002 (0.3); 2.8362 (0.4); 2.7669 (0.5); 2.7470 (0.5); 2.7349 (0.5); 2.7119 (1.0); 2.6757 (11.9); 2.6712 (16.0); 2.6667 (11.4); 2.6620 (5.4); 2.5415 (155.6); 2.5247 (51.1); 2.5199 (78.5); 2.5111 (1031.6); 2.5068 (1994.3); 2.5023 (2533.7); 2.4977 (1815.4); 2.4933 (865.9); 2.3977 (0.6); 2.3678 (0.7); 2.3336 (11.6); | 451.0 | |
I-102 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0196 (15.8); 9.0074 (16.0); 8.7843 (0.7); 8.7722 (1.4); 8.7672 (2.3); 8.7565 (0.7); 8.7482 (2.2); 8.7085 (3.0); 8.7061 (3.1); 8.6909 (3.1); 8.6884 (3.1); 8.3130 (2.1); 8.1805 (11.2); 7.7649 (1.8); 7.7620 (3.1); 7.7593 (1.9); 7.7424 (2.0); 7.7397 (3.4); 7.7368 (2.0); 7.6515 (4.2); 7.6393 (8.0); 7.6271 (4.1); 7.5605 (0.3); 7.3028 (1.8); 7.3003 (2.0); 7.2859 (2.1); 7.2834 (2.2); 7.2806 (1.9); 7.2780 (1.8); 7.2636 (2.0); 7.2611 (2.0); 7.0491 (2.0); 7.0456 (2.1); 7.0318 (3.2); 7.0284 (3.2); 7.0146 (1.8); 7.0111 (1.7); 6.9429 (7.4); 6.9409 (7.6); 6.0950 (0.4); 6.0777 (1.8); 6.0596 (2.4); 6.0415 (1.8); 6.0239 (0.4); 3.3246 (263.2); 2.6808 (0.8); 2.6762 (1.7); 2.6716 (2.4); 2.6671 (1.7); 2.6625 (0.8); 2.5659 (0.3); 2.5420 (13.4); 2.5252 (7.4); 2.5205 (11.0); 2.5118 (139.5); 2.5073 (283.8); 2.5027 (373.3); 2.4981 (270.1); 2.4935 (130.4); 2.3387 (0.7); 2.3341 (1.6); 2.3295 (2.3); 2.3250 (1.6); 2.3205 (0.8); 2.0738 (4.0); 1.6236 (11.8); 1.6064 (11.8); 0.0081 (0.6); -0.0001 (21.4); -0.0085 (0.6) | 335.1 | |
I-103 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0147 (15.7); 9.0026 (16.0); 8.9901 (2.1); 8.9780 (2.1); 8.8219 (2.9); 8.8024 (2.9); 8.3130 (3.9); 8.2739 (0.4); 8.2542 (0.4); 8.2030 (13.2); 8.1592 (0.5); 8.1224 (3.6); 8.1041 (3.9); 8.1008 (4.0); 7.7423 (0.5); 7.7254 (0.6); 7.6937 (1.2); 7.6785 (4.3); 7.6610 (3.9); 7.6568 (5.4); 7.6445 (8.2); 7.6324 (4.3); 7.6175 (0.6); 7.4873 (0.4); 7.4650 (0.5); 7.4440 (3.0); 7.4261 (3.6); 7.4037 (2.4); 7.3807 (1.9); 7.2858 (1.5); 7.2348 (14.3); 6.1097 (0.5); 6.0920 (2.2); 6.0736 (3.0); 6.0557 (2.2); 6.0383 (0.5); 5.8445 (0.4); 4.4988 (0.6); 4.4875 (0.8); 4.4760 (0.6); 3.9088 (1.2); 3.8999 (1.3); 3.7717 (0.6); 3.7603 (0.7); 3.7479 (0.5); 3.4846 (0.5); 3.3251 (471.9); 2.7112 (0.4); 2.6803 (1.9); 2.6760 (4.0); 2.6715 (5.6); 2.6670 (4.1); 2.6626 (2.0); 2.6033 (0.4); 2.5420 (92.4); 2.5250 (16.9); 2.5203 (26.7); 2.5115 (341.6); 2.5072 (684.5); 2.5026 (896.2); 2.4980 (661.8); 2.4936 (328.8); 2.3686 (0.4); 2.3385 (1.8); 2.3340 (3.9); 2.3294 (5.5); 2.3249 (4.1); 2.3204 (2.0); 2.0737 (11.3); 1.6436 (14.0); 1.6263 (14.0); 1.4776 (2.0); 1.4603 (1.9); 0.0079 (1.2); -0.0002 (39.5); -0.0085 (1.2) | 403.1 | |
I-104 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3494 (2.5); 9.3308 (2.5); 9.0119 (15.8); 8.9998 (16.0); 8.9926 (1.1); 8.9804 (0.8); 8.3126 (5.0); 8.2242 (2.1); 8.2191 (2.4); 8.2039 (14.4); 8.0967 (0.3); 8.0660 (0.7); 7.6884 (2.2); 7.6838 (2.3); 7.6748 (2.3); 7.6701 (2.2); 7.6639 (4.5); 7.6517 (8.1); 7.6395 (4.2); 6.0477 (0.5); 6.0304 (2.0); 6.0127 (3.1); 5.9950 (2.1); 5.9781 (0.5); 3.9072 (0.6); 3.8981 (0.5); 3.7577 (0.3); 3.5061 (0.3); 3.4314 (0.4); 3.3908 (0.6); 3.3244 (853.0); 3.2769 (0.4); 2.6758 (4.7); 2.6713 (6.6); 2.6668 (4.9); 2.6623 (2.4); 2.5417 (36.6); 2.5248 (20.7); 2.5200 (32.3); 2.5113 (397.7); 2.5069 (800.2); 2.5024 (1050.5); 2.4978 (774.7); 2.4933 (385.9); 2.4290 (0.4); 2.3383 (2.1); 2.3338 (4.6); 2.3292 (6.4); 2.3246 (4.7); 2.3201 (2.3); 2.0733 (4.3); 1.6153 (13.1); 1.5980 (13.1); 1.4683 (0.8); 1.4514 (0.8); 1.2347 (0.4); 0.0081 (1.5); -0.0001 (47.6); -0.0083 (1.8) | 415.0 | |
I-105 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.9981 (3.1); 8.8512 (13.7); 8.8507 (13.8); 8.7343 (3.6); 8.7158 (3.7); 8.3124 (2.4); 8.1585 (4.1); 8.0898 (14.6); 7.8700 (0.6); 7.8612 (6.1); 7.8556 (2.2); 7.8494 (6.6); 7.8439 (3.7); 7.8383 (7.0); 7.8322 (2.3); 7.8265 (6.6); 7.8175 (0.6); 7.6419 (2.0); 7.3916 (0.6); 7.3826 (6.8); 7.3770 (2.0); 7.3704 (1.0); 7.3606 (10.0); 7.3507 (0.8); 7.3442 (1.9); 7.3385 (6.2); 7.3296 (0.5); 6.0234 (0.5); 6.0058 (2.4); 5.9880 (3.6); 5.9701 (2.4); 5.9526 (0.5); 3.3305 (308.5); 2.6811 (0.8); 2.6766 (1.8); 2.6719 (2.5); 2.6673 (1.8); 2.6628 (0.8); 2.5423 (26.8); 2.5255 (7.8); 2.5208 (11.7); 2.5121 (146.8); 2.5076 (298.0); 2.5030 (391.0); 2.4983 (281.8); 2.4938 (135.3); 2.3389 (0.8); 2.3344 (1.7); 2.3298 (2.4); 2.3252 (1.7); 2.3207 (0.8); 2.0736 (4.6); 1.6312 (16.0); 1.6138 (16.0); 0.0081 (0.7); -0.0001 (23.1); -0.0084 (0.7) | 379.1 | |
I-106 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0465 (0.8); 9.0445 (0.8); 9.0196 (16.0); 9.0074 (14.6); 8.8039 (2.0); 8.7847 (2.1); 8.3118 (2.7); 8.1836 (10.6); 7.8314 (3.6); 7.8299 (3.6); 7.8062 (4.5); 7.7828 (0.8); 7.6520 (3.8); 7.6398 (7.2); 7.6277 (3.6); 7.3708 (3.5); 7.3663 (3.3); 7.3571 (0.8); 7.3526 (0.9); 7.3471 (3.1); 7.3427 (3.0); 7.3336 (0.6); 7.3290 (0.6); 7.0355 (7.2); 7.0336 (7.1); 6.9113 (1.4); 6.9094 (1.4); 6.0925 (0.4); 6.0753 (1.7); 6.0573 (2.3); 6.0392 (1.7); 6.0216 (0.4); 3.3256 (431.0); 3.3022 (0.8); 3.1997 (5.2); 3.0261 (4.7); 2.6809 (1.0); 2.6765 (2.3); 2.6719 (3.2); 2.6673 (2.2); 2.6627 (1.0); 2.5422 (44.6); 2.5254 (10.0); 2.5207 (14.7); 2.5120 (185.8); 2.5075 (375.1); 2.5029 (491.4); 2.4982 (352.5); 2.4937 (167.6); 2.3389 (1.0); 2.3343 (2.2); 2.3297 (3.1); 2.3251 (2.2); 2.3205 (1.0); 2.0733 (2.0); 1.6192 (11.2); 1.6020 (11.2); 0.0080 (0.7); -0.0002 (24.9); -0.0085 (0.7) | 369.0 | |
I-107 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1559 (1.8); 9.1377 (1.8); 8.9985 (1.6); 8.9861 (16.0); 8.9739 (14.7); 8.3118 (1.5); 8.1514 (10.6); 8.1184 (1.0); 7.6526 (0.4); 7.6403 (4.6); 7.6281 (7.8); 7.6160 (3.8); 6.6128 (1.1); 6.4133 (11.3); 6.3842 (0.4); 5.9913 (0.4); 5.9739 (1.8); 5.9562 (2.8); 5.9384 (1.8); 5.9209 (0.4); 4.4477 (0.3); 4.4404 (0.3); 4.4365 (0.4); 4.4320 (0.3); 4.4249 (0.3); 4.2188 (0.7); 3.8808 (0.8); 3.8713 (0.8); 3.7242 (0.4); 3.7129 (0.5); 3.7018 (0.5); 3.3259 (228.4); 3.0462 (1.7); 2.9849 (1.5); 2.6810 (0.5); 2.6765 (1.0); 2.6719 (1.5); 2.6674 (1.1); 2.6628 (0.5); 2.5422 (32.8); 2.5255 (4.5); 2.5208 (6.8); 2.5121 (90.4); 2.5076 (184.3); 2.5029 (242.9); 2.4983 (175.3); 2.4938 (84.2); 2.3390 (0.5); 2.3344 (1.1); 2.3298 (1.6); 2.3252 (1.1); 2.3207 (0.5); 2.1911 (0.7); 2.1784 (1.3); 2.1697 (1.3); 2.1663 (0.9); 2.1573 (2.4); 2.1485 (0.8); 2.1449 (1.4); 2.1362 (1.2); 2.1238 (0.6); 2.0733 (1.3); 1.5922 (11.3); 1.5749 (11.3); 1.4867 (1.2); 1.4695 (1.1); 1.1181 (0.4); 1.1120 (0.5); 1.1025 (1.5); 1.0973 (0.7); 1.0913 (4.0); 1.0849 (4.4); 1.0818 (2.2); 1.0747 (2.0); 1.0703 (3.9); 1.0637 (3.9); 1.0538 (1.6); 0.9627 (0.4); 0.9530 (0.6); 0.9474 (0.5); 0.9405 (0.5); 0.9349 (0.6); 0.9107 (1.8); 0.9009 (4.3); 0.8945 (4.1); 0.8885 (4.1); 0.8822 (4.4); 0.8711 (1.2); -0.0001 (10.3) | 326.1 | |
I-108 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1565 (1.6); 9.1382 (1.6); 9.0017 (3.3); 8.9896 (3.3); 8.3448 (2.9); 8.3124 (2.4); 8.1581 (4.8); 7.9856 (1.4); 7.9637 (2.6); 7.9471 (2.9); 7.9256 (2.9); 7.8269 (2.2); 7.8226 (2.2); 7.8054 (1.6); 7.8011 (1.6); 7.6324 (1.2); 7.6266 (1.0); 7.6205 (2.4); 7.6093 (2.7); 7.6056 (2.1); 7.5975 (1.9); 7.5917 (3.5); 7.5857 (1.8); 7.5780 (1.5); 7.5740 (1.6); 7.5610 (0.6); 7.5571 (0.4); 6.0555 (1.2); 6.0378 (1.9); 6.0201 (1.2); 3.3386 (472.4); 2.6805 (1.0); 2.6761 (2.1); 2.6715 (3.0); 2.6669 (2.2); 2.6625 (1.0); 2.5419 (27.9); 2.5250 (9.4); 2.5203 (13.9); 2.5116 (174.0); 2.5071 (354.3); 2.5025 (467.2); 2.4979 (339.2); 2.4933 (163.9); 2.3385 (0.9); 2.3339 (2.0); 2.3293 (2.9); 2.3248 (2.1); 2.3202 (0.9); 2.0733 (16.0); 1.6788 (7.6); 1.6614 (7.6); -0.0001 (10.6) | 345.1 | |
I-109 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 8.8557 (1.7); 8.8375 (1.7); 8.8156 (10.6); 8.8140 (10.4); 8.3157 (0.4); 8.1147 (7.9); 7.9845 (5.2); 7.9801 (5.3); 7.4313 (5.4); 7.4270 (5.3); 5.9010 (0.3); 5.8835 (1.4); 5.8658 (2.1); 5.8481 (1.4); 3.3229 (52.7); 2.6755 (0.8); 2.6709 (1.1); 2.6664 (0.8); 2.6618 (0.4); 2.5244 (3.3); 2.5197 (5.0); 2.5110 (61.6); 2.5065 (125.2); 2.5020 (165.4); 2.4974 (119.9); 2.4929 (57.9); 2.3433 (16.0); 2.3288 (1.2); 2.3243 (0.8); 1.5892 (8.5); 1.5717 (8.5); 1.2583 (0.3); -0.0002 (5.8) | 349.1 | |
I-110 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.5461 (2.0); 9.5348 (2.1); 9.1065 (3.0); 9.1038 (3.0); 8.6355 (2.0); 8.6318 (2.0); 8.6212 (2.2); 8.6176 (2.1); 8.2477 (4.3); 8.2454 (2.6); 8.1548 (8.6); 8.1525 (8.1); 8.1272 (3.1); 8.1131 (2.9); 6.0723 (1.4); 6.0609 (2.1); 6.0494 (1.4); 3.4620 (0.4); 3.3911 (1067.5); 3.3301 (1.6); 3.3144 (20.3); 3.2964 (0.4); 2.6221 (0.4); 2.6193 (0.6); 2.6163 (0.4); 2.5280 (1.1); 2.5250 (1.4); 2.5220 (1.4); 2.5101 (67.0); 2.5072 (90.9); 2.5043 (68.6); 2.3941 (0.4); 2.3911 (0.6); 2.3881 (0.4); 2.0880 (1.6); 1.6929 (7.4); 1.6813 (7.4); 1.3977 (16.0); 1.2454 (0.6); 1.2343 (0.7); 1.2299 (0.7); 1.2186 (0.6); -0.0001 (4.4) | 499.0 | |
I-111 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3280 (1.9); 9.3098 (2.0); 9.0047 (11.5); 8.9981 (5.1); 8.9926 (16.0); 8.8504 (4.8); 8.8453 (4.9); 8.3510 (2.5); 8.3456 (4.6); 8.3402 (2.5); 8.1785 (9.0); 7.8658 (0.3); 7.8579 (3.2); 7.8527 (1.4); 7.8445 (3.5); 7.8358 (3.8); 7.8278 (1.4); 7.8224 (3.4); 7.8146 (0.4); 7.6444 (3.1); 7.6323 (5.8); 7.6201 (2.9); 7.4081 (0.4); 7.4002 (3.5); 7.3950 (1.1); 7.3833 (1.3); 7.3780 (6.6); 7.3728 (1.3); 7.3611 (1.0); 7.3559 (3.2); 6.0784 (0.3); 6.0610 (1.5); 6.0433 (2.4); 6.0256 (1.5); 6.0081 (0.3); 3.3317 (32.6); 2.5271 (0.9); 2.5223 (1.4); 2.5136 (17.3); 2.5092 (35.1); 2.5046 (46.3); 2.5000 (33.6); 2.4955 (16.2); 1.6773 (9.2); 1.6599 (9.2); -0.0002 (0.4) | 390.2 | |
I-112 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3415 (3.0); 9.3234 (3.1); 9.0206 (7.1); 9.0151 (7.2); 9.0055 (15.9); 8.9934 (16.0); 8.8690 (7.1); 8.8640 (7.1); 8.3752 (3.9); 8.3699 (6.8); 8.3645 (3.7); 8.1809 (13.0); 8.1705 (0.6); 7.8455 (1.2); 7.8390 (8.8); 7.8342 (3.1); 7.8223 (3.5); 7.8175 (10.9); 7.8110 (1.4); 7.6449 (4.3); 7.6327 (8.2); 7.6205 (5.5); 7.6135 (11.0); 7.6087 (3.4); 7.5968 (3.1); 7.5921 (9.0); 7.5855 (1.1); 6.0810 (0.5); 6.0637 (2.2); 6.0460 (3.4); 6.0284 (2.2); 6.0110 (0.5); 3.3376 (62.7); 2.5283 (1.1); 2.5148 (19.9); 2.5105 (38.4); 2.5060 (49.2); 2.5015 (35.7); 2.4971 (17.5); 2.0786 (1.1); 1.6799 (13.3); 1.6625 (13.2); -0.0002 (0.4) | 406.2 | |
I-113 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 8.8757 (6.0); 8.8730 (6.1); 8.3392 (4.0); 8.3355 (4.1); 8.3248 (4.4); 8.3211 (4.6); 8.0923 (6.1); 8.0780 (5.4); 8.0694 (0.3); 8.0450 (13.2); 8.0326 (1.0); 7.8205 (2.3); 7.8083 (2.3); 7.2612 (8.1); 7.2582 (11.1); 7.2477 (2.4); 7.2438 (2.7); 7.2415 (1.9); 6.9945 (2.0); 6.9913 (3.0); 6.9881 (2.0); 6.9776 (2.1); 6.9748 (2.6); 6.9714 (1.9); 6.1992 (0.6); 6.1875 (2.5); 6.1757 (3.9); 6.1639 (2.6); 6.1522 (0.6); 5.4729 (3.2); 2.3061 (18.1); 1.9867 (3.2); 1.9786 (2.0); 1.9744 (2.4); 1.9707 (17.0); 1.9666 (30.8); 1.9625 (44.9); 1.9584 (31.9); 1.9542 (17.5); 1.9462 (3.0); 1.9381 (1.7); 1.9323 (1.5); 1.9240 (0.7); 1.6684 (0.4); 1.6511 (16.0); 1.6395 (16.0); 1.0435 (1.1); 1.0393 (1.4); 1.0355 (5.3); 1.0320 (5.6); 1.0216 (5.3); 1.0181 (5.4); 1.0146 (1.5); 1.0103 (1.1); 0.7667 (0.4); 0.7557 (2.2); 0.7510 (3.5); 0.7480 (5.4); 0.7445 (4.7); 0.7399 (5.2); 0.7366 (3.5); 0.7320 (1.7); 0.7194 (0.3); -0.0001 (0.8) | 377.1 | |
I-114 | 1H-NMR(600.1 MHz, CD3CN, 260 K): δ= 8.8502 (3.8); 8.8491 (4.1); 8.8466 (4.2); 8.8454 (4.0); 8.2970 (3.4); 8.2933 (3.4); 8.2827 (3.8); 8.2790 (3.8); 8.0575 (4.6); 8.0564 (4.7); 8.0432 (4.0); 8.0420 (4.2); 8.0308 (0.3); 8.0137 (9.9); 8.0017 (0.3); 7.7519 (6.5); 7.7491 (6.8); 7.5521 (1.1); 7.5404 (1.2); 7.2794 (0.3); 7.2747 (6.6); 7.2718 (6.7); 6.1640 (0.5); 6.1523 (2.2); 6.1404 (3.2); 6.1285 (2.2); 6.1168 (0.6); 5.4470 (7.6); 2.1654 (0.7); 1.9666 (0.6); 1.9586 (0.3); 1.9544 (0.4); 1.9506 (3.2); 1.9465 (6.0); 1.9424 (8.8); 1.9383 (6.1); 1.9341 (3.2); 1.6302 (0.7); 1.6282 (0.7); 1.6215 (15.8); 1.6100 (16.0) | 359.0 | |
I-115 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1428 (2.6); 9.1245 (2.7); 8.9973 (15.7); 8.9852 (16.0); 8.9342 (0.4); 8.9221 (0.4); 8.1574 (12.7); 8.0285 (3.2); 8.0245 (5.5); 8.0206 (3.3); 7.8737 (0.3); 7.8513 (1.0); 7.8439 (8.8); 7.8387 (2.9); 7.8274 (5.1); 7.8219 (10.5); 7.8132 (2.8); 7.8092 (3.0); 7.7600 (2.7); 7.7436 (2.4); 7.7402 (3.2); 7.6363 (4.2); 7.6241 (8.1); 7.6120 (4.2); 7.6060 (0.4); 7.5841 (0.3); 7.5484 (3.2); 7.5290 (5.6); 7.5091 (3.9); 7.5033 (5.8); 7.4831 (5.1); 6.0543 (0.4); 6.0370 (2.0); 6.0193 (3.2); 6.0015 (2.0); 5.9840 (0.4); 3.3252 (52.0); 2.8912 (0.4); 2.7322 (0.3); 2.6760 (0.7); 2.6715 (0.9); 2.6669 (0.7); 2.5250 (2.4); 2.5202 (3.5); 2.5115 (53.8); 2.5071 (110.6); 2.5025 (146.3); 2.4979 (104.4); 2.4934 (49.0); 2.3340 (0.6); 2.3294 (0.9); 2.3248 (0.7); 1.6628 (12.6); 1.6454 (12.7); 1.6244 (0.4); 1.3975 (12.6); 0.1459 (1.5); 0.0253 (0.4); 0.0079 (11.7); -0.0002 (327.4); -0.0086 (11.3); -0.0205 (0.4); -0.1496 (1.5) | 455.3 | |
I-116 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3383 (2.8); 9.3201 (2.9); 9.0324 (6.2); 9.0269 (6.4); 9.0084 (15.7); 8.9963 (16.0); 8.8858 (6.4); 8.8807 (6.6); 8.3935 (3.6); 8.3881 (6.6); 8.3827 (3.6); 8.2166 (5.6); 8.1807 (13.0); 7.9382 (1.0); 7.9308 (8.9); 7.9257 (3.0); 7.9138 (3.5); 7.9089 (11.2); 7.9016 (1.2); 7.8945 (1.0); 7.8896 (2.7); 7.6480 (4.2); 7.6359 (8.0); 7.6237 (4.1); 7.5482 (5.8); 7.5280 (5.3); 7.3215 (1.5); 7.3022 (1.4); 6.0856 (0.4); 6.0684 (2.1); 6.0508 (3.3); 6.0331 (2.2); 6.0156 (0.5); 3.3354 (34.8); 2.5288 (0.8); 2.5238 (1.2); 2.5152 (17.5); 2.5108 (35.9); 2.5063 (47.5); 2.5017 (34.5); 2.4972 (16.7); 2.0785 (0.8); 1.6799 (12.8); 1.6625 (12.8); 0.1460 (0.5); 0.0079 (4.4); -0.0002 (112.0); -0.0086 (4.4); -0.1496 (0.5) | 456.2 | |
I-117 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5333 (3.9); 9.5160 (4.0); 9.3760 (9.4); 9.3729 (9.8); 9.2583 (9.9); 9.2551 (9.4); 8.3692 (16.0); 8.3118 (9.1); 8.3083 (5.6); 8.2244 (5.0); 8.2203 (8.2); 8.2164 (5.3); 8.1614 (5.4); 8.1572 (8.4); 8.1529 (4.5); 6.0957 (0.6); 6.0785 (2.7); 6.0612 (4.2); 6.0438 (2.7); 6.0269 (0.6); 3.3264 (163.6); 2.6757 (0.6); 2.6714 (0.9); 2.6670 (0.6); 2.5245 (2.6); 2.5068 (103.8); 2.5025 (135.6); 2.4981 (99.8); 2.3337 (0.6); 2.3293 (0.8); 2.3249 (0.6); 2.0747 (1.4); 1.6431 (15.8); 1.6258 (15.7); 0.1458 (1.3); 0.0077 (10.9); -0.0002 (257.8); -0.0084 (11.2); -0.1497 (1.3) | 432.2 | |
I-118 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6157 (1.4); 9.5982 (1.4); 8.5829 (2.9); 8.5755 (2.9); 8.4795 (2.0); 8.4753 (3.4); 8.4710 (2.3); 8.4100 (3.2); 8.4052 (2.7); 8.3989 (2.6); 8.3161 (0.4); 8.1667 (6.7); 8.0525 (0.8); 8.0450 (0.8); 8.0302 (1.3); 8.0228 (1.3); 8.0098 (1.1); 8.0023 (1.0); 7.9210 (1.7); 7.9112 (1.8); 7.8985 (1.2); 7.8887 (1.2); 5.9630 (1.0); 5.9456 (1.6); 5.9281 (1.0); 3.5685 (16.0); 3.3258 (109.9); 2.6807 (0.3); 2.6762 (0.6); 2.6714 (0.9); 2.6670 (0.6); 2.5249 (2.6); 2.5115 (53.3); 2.5071 (106.8); 2.5025 (139.6); 2.4979 (99.4); 2.4934 (46.6); 2.3339 (0.6); 2.3293 (0.8); 2.3249 (0.6); 1.9089 (5.2); 1.6511 (6.4); 1.6337 (6.4); 1.2982 (0.5); 1.2588 (0.8); 1.2345 (1.5); 0.1458 (1.4); 0.0079 (14.0); -0.0002 (318.4); -0.0086 (11.0); -0.1497 (1.4) | 478.1 | |
I-119 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2840 (2.3); 9.2666 (2.4); 9.0658 (4.3); 9.0615 (4.1); 9.0604 (4.2); 8.5864 (3.2); 8.5809 (3.2); 8.5650 (3.5); 8.5594 (3.5); 8.2418 (11.1); 8.0817 (4.5); 8.0614 (4.0); 8.0601 (4.2); 7.8059 (3.2); 7.8017 (5.4); 7.7976 (3.6); 7.7014 (3.4); 7.6974 (5.8); 7.6936 (3.4); 7.5266 (3.5); 7.5220 (6.2); 7.5174 (3.2); 6.1008 (0.4); 6.0835 (1.8); 6.0662 (2.8); 6.0487 (1.8); 6.0312 (0.4); 5.7561 (7.8); 3.3257 (96.8); 2.6759 (0.6); 2.6715 (0.8); 2.6670 (0.6); 2.5249 (2.1); 2.5201 (3.2); 2.5115 (44.9); 2.5071 (92.1); 2.5025 (121.9); 2.4980 (87.4); 2.4935 (41.4); 2.3339 (0.5); 2.3294 (0.7); 2.3249 (0.5); 1.8164 (1.9); 1.8038 (5.5); 1.7963 (5.9); 1.7848 (2.5); 1.7454 (0.3); 1.6727 (0.4); 1.6392 (10.7); 1.6347 (4.9); 1.6218 (16.0); 1.6147 (6.4); 1.6013 (2.1); 0.1458 (1.1); 0.0078 (9.0); -0.0002 (245.2); -0.0086 (8.7); -0.1497 (1.1) | 418.3 | |
I-120 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 9.2780 (1.8); 9.2670 (1.9); 8.8779 (5.9); 8.8750 (5.8); 8.3608 (4.0); 8.3571 (3.9); 8.3464 (4.4); 8.3427 (4.4); 8.0983 (6.1); 8.0839 (5.5); 8.0642 (12.8); 7.2442 (2.0); 7.2413 (2.8); 7.2379 (2.1); 7.2281 (2.0); 7.2254 (2.8); 7.2217 (2.0); 7.1775 (7.7); 6.9465 (2.1); 6.9438 (2.7); 6.9406 (1.9); 6.9298 (2.2); 6.9271 (2.7); 6.9238 (1.9); 6.5544 (0.6); 6.5429 (2.6); 6.5314 (4.0); 6.5199 (2.6); 6.5084 (0.6); 2.3029 (7.9); 1.9862 (16.2); 1.9781 (2.3); 1.9740 (3.1); 1.9702 (17.5); 1.9662 (31.8); 1.9620 (46.0); 1.9579 (31.7); 1.9538 (17.9); 1.9451 (1.8); 1.9391 (1.5); 1.9309 (0.7); 1.7892 (16.0); 1.7776 (16.0); 1.2726 (0.4); 1.2573 (0.6); 1.0455 (1.8); 1.0380 (5.3); 1.0345 (5.4); 1.0270 (2.7); 1.0241 (5.4); 1.0206 (5.2); 1.0134 (2.0); 0.7566 (2.0); 0.7491 (6.4); 0.7459 (5.6); 0.7411 (5.5); 0.7378 (6.5); 0.7301 (1.8); 0.0053 (0.7); -0.0001 (20.8); -0.0056 (0.7) | 393.1 | |
I-121 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 8.8014 (2.7); 8.3775 (1.4); 8.3743 (1.4); 8.3632 (1.6); 8.3601 (1.5); 8.3373 (2.0); 8.2805 (1.2); 8.2661 (1.2); 8.1155 (4.4); 8.0807 (2.4); 8.0631 (3.5); 8.0328 (1.6); 7.8978 (1.6); 7.8835 (1.5); 6.8608 (1.4); 6.8437 (1.4); 6.6308 (1.4); 6.6152 (2.2); 6.5966 (1.0); 6.5400 (0.8); 6.5265 (0.8); 6.4935 (1.8); 6.4223 (3.2); 6.3770 (0.5); 6.3654 (1.5); 6.3539 (1.5); 6.3426 (0.5); 6.2014 (0.4); 6.1900 (1.1); 6.1785 (1.1); 6.1670 (0.4); 4.0680 (2.3); 4.0561 (7.0); 4.0442 (7.0); 4.0323 (2.3); 3.7163 (0.6); 3.7061 (0.7); 3.6927 (0.9); 3.6823 (0.9); 3.5524 (0.8); 3.5406 (0.9); 3.5286 (0.7); 3.5170 (0.7); 2.8859 (0.4); 2.8736 (0.3); 2.8597 (1.8); 2.8483 (3.3); 2.8394 (1.8); 2.8229 (0.4); 2.2975 (49.5); 2.0805 (0.5); 2.0764 (0.9); 2.0723 (1.3); 2.0682 (0.9); 2.0641 (0.5); 1.9846 (39.0); 1.9776 (11.2); 1.9733 (14.4); 1.9696 (89.0); 1.9655 (158.1); 1.9614 (230.0); 1.9573 (158.4); 1.9532 (80.2); 1.9445 (1.2); 1.8867 (0.3); 1.8779 (0.7); 1.8718 (0.9); 1.8643 (1.2); 1.8546 (1.2); 1.8505 (1.6); 1.8464 (1.6); 1.8423 (1.3); 1.8382 (0.6); 1.8021 (6.1); 1.7905 (6.3); 1.7543 (4.6); 1.7427 (4.7); 1.7327 (1.1); 1.7169 (0.7); 1.2734 (0.4); 1.2611 (0.7); 1.2178 (8.0); 1.2059 (16.0); 1.1940 (8.0); 1.1113 (0.6); 1.1000 (0.9); 1.0869 (0.7); 1.0762 (0.6); 1.0221 (0.6); 1.0095 (5.4); 0.9957 (5.1); 0.9878 (1.1); 0.6355 (2.8); 0.6089 (0.5); 0.6013 (0.6); 0.5962 (0.6); 0.5876 (1.0); 0.5792 (1.0); 0.5699 (0.5); 0.5521 (1.4); 0.5448 (1.7); 0.5360 (1.2); 0.5136 (0.7); 0.5055 (0.8); 0.4994 (0.8); 0.4908 (0.9); 0.4854 (0.9); 0.4770 (0.8); 0.4695 (0.8); 0.4632 (0.6); 0.3493 (0.5); 0.3419 (0.7); 0.3336 (0.9); 0.3279 (0.8); 0.3005 (0.8); 0.2947 (0.9); 0.2869 (0.7); 0.2794 (0.4); 0.2694 (0.4); 0.2599 (0.5); 0.2532 (0.8); 0.2455 (1.0); 0.2386 (0.9); 0.2320 (0.7); 0.2231 (0.5); 0.2166 (0.5); 0.2081 (0.8); 0.2007 (0.8); 0.1948 (1.0); 0.1875 (0.7); 0.0967 (0.4); 0.0053 (3.2); -0.0001 (100.6); -0.0057 (3.3); -0.1002 (0.5); -0.1642 (0.3); -0.1724 (0.8); -0.1803 (1.1); -0.1881 (1.1); -0.1959 (0.8); -0.2041 (0.4); -0.3881 (0.4); -0.3960 (0.8); -0.4037 (1.1); -0.4116 (1.0); -0.4194 (0.7) | 431.1 | |
I-122 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4670 (1.3); 9.4495 (1.4); 9.0410 (2.3); 9.0395 (2.4); 9.0354 (2.5); 9.0339 (2.3); 8.5518 (1.8); 8.5461 (1.8); 8.5304 (2.0); 8.5247 (2.0); 8.3162 (0.4); 8.2613 (1.8); 8.2576 (3.4); 8.2538 (2.1); 8.2308 (6.1); 8.1650 (1.6); 8.1604 (3.0); 8.1564 (2.1); 8.1395 (2.3); 8.1352 (3.1); 8.1306 (1.5); 8.0364 (2.5); 8.0351 (2.4); 8.0151 (2.3); 8.0136 (2.3); 6.1327 (1.0); 6.1153 (1.5); 6.0978 (1.0); 3.9177 (16.0); 3.3236 (42.0); 3.3135 (16.1); 2.6757 (0.5); 2.6711 (0.7); 2.6665 (0.5); 2.5247 (1.9); 2.5199 (2.8); 2.5111 (39.1); 2.5067 (79.5); 2.5022 (104.8); 2.4976 (75.6); 2.4931 (36.4); 2.3336 (0.5); 2.3290 (0.6); 2.3245 (0.5); 1.6621 (5.6); 1.6448 (5.6); 0.1459 (0.8); 0.0080 (6.2); -0.0002 (178.7); -0.0085 (6.9); -0.0201 (0.3); -0.1497 (0.8) | 464.2 | |
I-123 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4556 (1.7); 9.4381 (1.7); 9.0776 (2.9); 9.0759 (3.1); 9.0722 (3.1); 9.0704 (2.8); 8.5806 (2.5); 8.5750 (2.3); 8.5591 (2.6); 8.5535 (2.6); 8.3394 (3.1); 8.3138 (1.7); 8.2525 (7.8); 8.1304 (3.0); 8.0909 (4.4); 8.0892 (5.0); 8.0856 (3.2); 8.0696 (3.1); 8.0678 (3.0); 7.8876 (2.6); 7.8822 (1.1); 7.8742 (2.9); 7.8654 (3.0); 7.8573 (1.2); 7.8520 (2.7); 7.3872 (2.9); 7.3822 (0.9); 7.3651 (5.4); 7.3483 (0.9); 7.3430 (2.6); 6.1499 (1.2); 6.1325 (1.8); 6.1152 (1.2); 3.8242 (0.3); 3.3296 (659.1); 2.6806 (0.8); 2.6763 (1.6); 2.6717 (2.3); 2.6670 (1.6); 2.6628 (0.8); 2.5621 (0.4); 2.5251 (7.2); 2.5203 (11.3); 2.5117 (134.9); 2.5072 (270.4); 2.5027 (353.9); 2.4981 (254.5); 2.4936 (120.9); 2.3386 (0.7); 2.3341 (1.6); 2.3295 (2.2); 2.3250 (1.6); 2.3205 (0.7); 1.9886 (0.4); 1.6800 (7.0); 1.6625 (7.0); 1.3981 (16.0); 1.2359 (2.4); 1.1757 (0.4); 0.8542 (0.5); 0.1459 (2.7); 0.0079 (25.7); -0.0002 (649.7); -0.0086 (24.6); -0.0328 (0.5); -0.1496 (2.8) | 481.2 | |
I-124 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1432 (0.4); 9.1252 (0.4); 8.9885 (2.2); 8.9763 (2.2); 8.1569 (1.8); 7.6757 (0.6); 7.6719 (1.0); 7.6680 (0.7); 7.6337 (0.6); 7.6215 (1.2); 7.6168 (0.7); 7.6122 (1.0); 7.6092 (1.1); 7.5473 (0.6); 7.5428 (1.0); 7.5383 (0.5); 5.9629 (0.5); 3.3229 (8.5); 2.5245 (0.6); 2.5111 (11.0); 2.5067 (21.5); 2.5022 (27.8); 2.4977 (20.4); 2.4934 (10.0); 1.6417 (1.9); 1.6243 (1.9); 1.2708 (16.0); 0.0079 (1.6); -0.0002 (37.0); -0.0085 (1.5) | 385.2 | |
I-125 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1484 (0.4); 9.1304 (0.4); 8.9900 (2.5); 8.9778 (2.6); 8.1583 (2.0); 7.7544 (0.6); 7.7503 (1.0); 7.7462 (0.7); 7.7141 (0.6); 7.7100 (1.1); 7.7061 (0.6); 7.6711 (0.7); 7.6667 (1.1); 7.6623 (0.5); 7.6355 (0.7); 7.6233 (1.3); 7.6112 (0.7); 5.9620 (0.5); 3.3275 (1.7); 2.5127 (3.8); 2.5082 (7.7); 2.5036 (10.1); 2.4990 (7.3); 2.4945 (3.5); 2.0760 (3.5); 1.6414 (1.9); 1.6240 (1.9); 1.2668 (16.0); 0.0079 (0.8); -0.0002 (19.4); -0.0086 (0.7) | 431.2 | |
I-126 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 13.6217 (1.4); 9.4748 (3.7); 9.4572 (3.8); 9.0148 (6.6); 9.0105 (6.6); 8.5268 (4.5); 8.5212 (4.3); 8.5055 (4.8); 8.4999 (4.8); 8.2759 (5.2); 8.2723 (9.1); 8.2686 (5.4); 8.2207 (16.0); 8.1685 (4.6); 8.1641 (8.0); 8.1602 (5.6); 8.1391 (5.9); 8.1349 (8.2); 8.1305 (4.1); 8.0145 (6.5); 7.9933 (6.0); 6.1559 (0.6); 6.1385 (2.5); 6.1211 (3.9); 6.1037 (2.5); 6.0862 (0.5); 3.3272 (9.9); 3.3161 (42.0); 2.6771 (0.6); 2.6725 (0.7); 2.6679 (0.6); 2.5258 (2.7); 2.5123 (47.5); 2.5080 (92.8); 2.5035 (119.9); 2.4990 (87.6); 2.4947 (43.4); 2.3348 (0.5); 2.3304 (0.7); 2.3258 (0.5); 1.6628 (14.5); 1.6455 (14.4); 0.1459 (0.5); 0.0078 (5.0); -0.0002 (118.3); -0.0085 (5.0); -0.1496 (0.6) | 450.2 | |
I-127 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.0999 (1.8); 9.7311 (0.5); 9.5257 (2.4); 9.5085 (2.4); 9.3731 (4.7); 9.3720 (4.9); 9.3663 (5.0); 9.3651 (4.7); 8.9482 (2.4); 8.9422 (2.4); 8.8570 (3.9); 8.8501 (3.7); 8.8344 (4.1); 8.8275 (4.0); 8.3159 (0.5); 8.2891 (4.0); 8.2843 (15.6); 8.2747 (1.3); 8.2678 (1.1); 8.2513 (1.1); 8.2444 (1.0); 8.2127 (3.6); 8.2081 (5.5); 8.2040 (3.8); 8.1616 (5.2); 8.1605 (5.2); 8.1514 (4.1); 8.1470 (6.0); 8.1424 (3.6); 8.1392 (5.2); 8.1379 (5.0); 6.6498 (0.6); 6.6265 (0.6); 6.1755 (0.4); 6.1586 (1.8); 6.1413 (2.8); 6.1239 (1.8); 6.1065 (0.4); 3.3450 (0.8); 3.3259 (118.8); 3.3196 (32.7); 2.6805 (0.4); 2.6760 (0.7); 2.6714 (1.0); 2.6668 (0.8); 2.6622 (0.3); 2.5250 (2.8); 2.5202 (4.2); 2.5116 (60.9); 2.5071 (124.5); 2.5025 (163.9); 2.4979 (115.6); 2.4933 (53.5); 2.3384 (0.3); 2.3338 (0.7); 2.3293 (1.0); 2.3247 (0.7); 2.0750 (2.5); 1.9891 (0.9); 1.9423 (16.0); 1.8323 (0.5); 1.6721 (10.8); 1.6547 (10.7); 1.1752 (0.5); 0.1460 (0.5); 0.0081 (4.3); -0.0001 (130.8); -0.0085 (3.9); -0.1495 (0.5) | 451.1 | |
I-128 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4780 (3.3); 9.4603 (3.4); 9.1970 (1.6); 9.1825 (3.3); 9.1678 (1.6); 9.0037 (5.9); 8.9993 (5.8); 8.9979 (5.7); 8.5027 (4.1); 8.4968 (3.9); 8.4813 (4.4); 8.4754 (4.5); 8.3163 (0.5); 8.2842 (4.8); 8.2804 (9.2); 8.2766 (5.5); 8.2137 (16.0); 8.1930 (0.5); 8.1828 (4.6); 8.1782 (7.7); 8.1742 (5.4); 8.1379 (5.6); 8.1335 (8.2); 8.1291 (4.4); 8.0135 (6.1); 7.9920 (5.7); 6.3021 (0.7); 6.2924 (1.4); 6.2826 (0.6); 6.1627 (1.5); 6.1529 (3.4); 6.1432 (1.6); 6.1323 (2.4); 6.1149 (3.7); 6.0974 (2.4); 6.0799 (0.5); 6.0232 (0.7); 6.0134 (1.6); 6.0037 (0.7); 3.7789 (1.0); 3.7689 (1.3); 3.7644 (1.2); 3.7544 (1.1); 3.7399 (2.2); 3.7299 (2.6); 3.7254 (2.5); 3.7154 (2.1); 3.7008 (1.2); 3.6906 (1.3); 3.6861 (1.3); 3.6762 (1.0); 3.3248 (43.5); 3.3145 (40.6); 2.6807 (0.4); 2.6761 (0.8); 2.6716 (1.1); 2.6671 (0.8); 2.6624 (0.4); 2.5251 (2.9); 2.5203 (4.6); 2.5117 (62.9); 2.5072 (128.2); 2.5026 (169.0); 2.4981 (121.4); 2.4935 (58.1); 2.3385 (0.4); 2.3340 (0.8); 2.3295 (1.1); 2.3249 (0.8); 2.3202 (0.4); 2.0752 (6.6); 1.6635 (13.5); 1.6461 (13.5); 1.2344 (1.4); 0.1459 (0.9); 0.0080 (8.0); -0.0001 (227.2); -0.0085 (8.0); -0.1496 (0.9) | 513.2 | |
I-129 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4741 (3.6); 9.4563 (3.7); 8.9431 (6.3); 8.9386 (6.3); 8.7435 (3.8); 8.7334 (3.7); 8.4389 (4.2); 8.4331 (3.9); 8.4176 (4.5); 8.4117 (4.4); 8.3162 (0.8); 8.2811 (5.2); 8.2774 (9.3); 8.2737 (5.5); 8.1994 (16.0); 8.1808 (4.9); 8.1763 (7.9); 8.1723 (5.4); 8.1382 (5.8); 8.1340 (8.4); 8.1295 (4.3); 7.9695 (6.5); 7.9482 (6.0); 6.1333 (0.6); 6.1164 (2.5); 6.0989 (3.9); 6.0814 (2.5); 6.0645 (0.6); 5.7564 (3.1); 3.3248 (173.5); 3.3166 (44.6); 2.9154 (0.6); 2.9056 (1.3); 2.8960 (1.8); 2.8875 (2.8); 2.8775 (2.7); 2.8691 (1.7); 2.8595 (1.2); 2.8494 (0.5); 2.7325 (0.4); 2.6897 (0.5); 2.6758 (1.6); 2.6712 (2.1); 2.6668 (1.6); 2.6623 (0.8); 2.5247 (7.0); 2.5197 (10.7); 2.5112 (128.1); 2.5068 (253.4); 2.5023 (328.3); 2.4978 (235.8); 2.4934 (113.1); 2.3336 (1.5); 2.3291 (2.0); 2.3245 (1.5); 1.6556 (14.8); 1.6383 (14.7); 0.7565 (1.5); 0.7435 (4.2); 0.7384 (6.2); 0.7264 (5.6); 0.7201 (4.8); 0.7090 (2.1); 0.6502 (0.4); 0.6210 (2.2); 0.6106 (6.5); 0.6034 (5.6); 0.5950 (4.6); 0.5825 (1.4); 0.1460 (1.9); 0.0080 (16.4); -0.0001 (432.7); -0.0085 (15.9); -0.1495 (1.9) | 489.2 | |
I-130 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6151 (8.0); 9.4761 (3.7); 9.4584 (3.8); 8.9702 (6.4); 8.9656 (6.4); 8.4736 (4.2); 8.4678 (4.0); 8.4522 (4.6); 8.4464 (4.5); 8.3163 (0.6); 8.2749 (5.2); 8.2712 (9.4); 8.2675 (5.6); 8.2170 (16.0); 8.1773 (4.9); 8.1728 (8.0); 8.1688 (5.4); 8.1381 (5.8); 8.1339 (8.3); 8.1294 (4.3); 8.0147 (6.6); 7.9934 (6.0); 6.1420 (0.6); 6.1249 (2.5); 6.1075 (4.0); 6.0899 (2.5); 6.0726 (0.5); 5.7564 (3.0); 3.3270 (157.4); 3.3149 (42.2); 2.8911 (1.7); 2.7320 (1.4); 2.6897 (0.6); 2.6758 (1.3); 2.6714 (1.8); 2.6669 (1.3); 2.5247 (6.2); 2.5112 (107.6); 2.5069 (212.8); 2.5024 (276.4); 2.4978 (199.5); 2.4934 (96.3); 2.3337 (1.2); 2.3292 (1.7); 2.3246 (1.2); 1.6578 (14.5); 1.6404 (14.4); 1.6181 (3.2); 1.6039 (7.3); 1.5968 (7.9); 1.5840 (3.4); 1.5439 (0.3); 1.3853 (0.3); 1.3456 (3.6); 1.3323 (7.4); 1.3255 (7.8); 1.3110 (2.8); 1.2735 (0.4); 1.2593 (0.4); 1.2437 (0.4); 0.1459 (1.5); 0.0079 (13.3); -0.0002 (347.3); -0.0085 (13.7); -0.1496 (1.5) | 514.2 | |
I-131 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4818 (3.1); 9.4641 (3.2); 9.4414 (1.6); 9.4259 (3.2); 9.4101 (1.5); 9.0236 (5.1); 9.0223 (5.3); 9.0179 (5.4); 9.0164 (5.0); 8.5233 (3.7); 8.5174 (3.5); 8.5019 (4.0); 8.4960 (4.0); 8.3163 (0.5); 8.2872 (4.5); 8.2834 (8.4); 8.2796 (4.9); 8.2186 (14.4); 8.1789 (4.3); 8.1743 (6.8); 8.1703 (4.8); 8.1371 (5.3); 8.1328 (7.3); 8.1283 (4.0); 8.0275 (5.5); 8.0262 (5.4); 8.0062 (5.1); 8.0047 (5.1); 6.1532 (0.4); 6.1360 (2.1); 6.1185 (3.3); 6.1010 (2.1); 6.0834 (0.5); 4.1965 (0.8); 4.1723 (2.7); 4.1564 (2.7); 4.1481 (2.9); 4.1322 (2.6); 4.1239 (1.1); 4.1079 (0.9); 3.3250 (36.1); 3.3137 (36.4); 2.6764 (0.6); 2.6719 (0.9); 2.6673 (0.7); 2.5253 (2.6); 2.5205 (4.1); 2.5119 (53.2); 2.5074 (107.0); 2.5029 (139.4); 2.4983 (99.4); 2.4938 (46.9); 2.3342 (0.6); 2.3297 (0.8); 2.3252 (0.6); 2.1376 (0.4); 2.0753 (16.0); 1.6662 (12.1); 1.6489 (12.1); 0.1459 (0.8); 0.0080 (6.9); -0.0002 (188.1); -0.0086 (6.5); -0.1496 (0.8) | 531.2 | |
I-132 | 1H-NMR(400.2 MHz, CD3CN): δ= 8.2913 (0.7); 8.0657 (2.3); 7.9058 (0.3); 6.6244 (0.5); 6.5930 (0.6); 6.5843 (0.6); 6.5124 (0.9); 3.7774 (0.6); 3.7733 (0.6); 2.1414 (21.2); 2.1134 (0.3); 2.1073 (0.5); 1.9643 (7.2); 1.9579 (2.2); 1.9524 (24.3); 1.9462 (46.4); 1.9400 (65.3); 1.9338 (44.6); 1.9277 (22.7); 1.9150 (0.4); 1.7809 (0.4); 1.7746 (0.5); 1.7685 (0.6); 1.7624 (0.6); 1.7559 (0.5); 1.7212 (16.0); 1.7037 (15.9); 1.3856 (0.4); 1.3219 (0.4); 1.3155 (0.3); 1.2689 (0.8); 1.1735 (1.0); 0.9913 (3.5); 0.9704 (3.2); 0.6296 (1.0); 0.6249 (1.0); 0.5947 (0.9); 0.1458 (1.1); 0.0191 (0.4); 0.0160 (0.4); 0.0079 (9.8); -0.0002 (245.8); -0.0086 (9.7); -0.1496 (1.1) | 405.3 | |
I-133 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3582 (2.2); 9.3400 (2.1); 8.2660 (3.1); 8.2625 (5.1); 8.2590 (3.3); 8.1475 (2.6); 8.1431 (4.8); 8.1393 (3.7); 8.1283 (3.8); 8.1242 (5.0); 8.1199 (2.5); 8.0225 (0.6); 8.0113 (8.3); 7.8022 (3.9); 7.7954 (3.8); 7.4132 (3.4); 7.3916 (4.0); 7.1311 (2.5); 7.1241 (2.4); 7.1095 (2.2); 7.1025 (2.1); 5.8060 (0.4); 5.7886 (1.5); 5.7708 (2.2); 5.7531 (1.4); 5.7355 (0.4); 5.6754 (7.2); 4.0560 (1.2); 4.0382 (3.8); 4.0205 (3.8); 4.0027 (1.3); 3.3285 (23.1); 3.3181 (23.0); 2.5075 (41.3); 2.5031 (53.6); 2.4988 (40.4); 2.3299 (0.4); 1.9895 (16.0); 1.9632 (0.3); 1.9435 (1.5); 1.9099 (0.7); 1.8331 (0.5); 1.8299 (0.5); 1.7863 (0.4); 1.6015 (0.7); 1.5833 (8.7); 1.5659 (8.3); 1.3363 (0.4); 1.2498 (0.3); 1.2352 (0.5); 1.1931 (4.4); 1.1753 (8.5); 1.1653 (0.7); 1.1575 (4.4); 1.1467 (0.5); 1.1306 (0.3); -0.0002 (3.6) | 421.2 | |
I-134 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4596 (3.4); 9.4419 (3.3); 8.6991 (3.4); 8.3162 (0.4); 8.2840 (6.6); 8.2187 (2.7); 8.1957 (16.0); 8.1343 (6.4); 7.9164 (4.9); 7.8955 (4.2); 6.1370 (1.9); 6.1196 (2.8); 6.1023 (1.8); 6.0869 (0.6); 5.7565 (4.0); 3.3233 (49.8); 3.3172 (33.0); 3.0083 (7.7); 2.8915 (0.4); 2.6712 (1.5); 2.5023 (198.0); 2.3296 (1.3); 1.6506 (11.6); 1.6335 (11.3); 0.5125 (2.4); 0.4115 (2.7); 0.1458 (0.7); -0.0002 (124.3); -0.1499 (0.7) | 503.2 | |
I-135 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4710 (2.5); 9.4533 (2.6); 8.9556 (4.7); 8.9501 (4.7); 8.7556 (1.9); 8.7442 (1.9); 8.4506 (2.8); 8.4448 (2.7); 8.4293 (3.0); 8.4235 (3.0); 8.2772 (6.2); 8.2739 (3.9); 8.2013 (10.3); 8.1928 (0.6); 8.1799 (3.2); 8.1759 (5.6); 8.1722 (3.8); 8.1364 (3.7); 8.1326 (5.6); 7.9791 (4.8); 7.9578 (4.5); 6.1371 (0.4); 6.1199 (1.8); 6.1025 (2.9); 6.0850 (1.9); 6.0671 (0.4); 3.3269 (92.6); 3.3154 (28.6); 3.0150 (0.3); 2.9126 (0.4); 2.8913 (0.6); 2.8314 (12.6); 2.8201 (12.6); 2.7316 (0.4); 2.6900 (1.1); 2.6761 (0.6); 2.6715 (0.9); 2.6672 (0.6); 2.5247 (2.6); 2.5070 (103.3); 2.5027 (134.6); 2.4982 (98.5); 2.3337 (0.6); 2.3295 (0.8); 2.3252 (0.6); 2.0750 (16.0); 1.6593 (10.7); 1.6419 (10.7); 0.1457 (0.7); 0.0077 (5.0); -0.0002 (143.5); -0.0085 (5.5); -0.1498 (0.7) | 463.1 | |
I-136 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5184 (1.7); 9.5009 (1.9); 9.4910 (16.0); 8.9765 (0.4); 8.2928 (2.1); 8.2892 (4.0); 8.2856 (2.6); 8.2719 (7.1); 8.2172 (2.1); 8.2128 (3.6); 8.2090 (2.4); 8.1555 (2.3); 8.1511 (3.7); 8.1469 (2.1); 6.0988 (1.1); 6.0814 (1.8); 6.0642 (1.2); 3.3551 (0.4); 3.3457 (0.3); 3.3252 (52.5); 3.2744 (1.1); 2.6754 (0.4); 2.6709 (0.5); 2.6664 (0.4); 2.5239 (1.5); 2.5064 (63.3); 2.5019 (83.6); 2.4975 (62.2); 2.3330 (0.4); 2.3288 (0.5); 2.3244 (0.4); 2.0756 (0.9); 1.6527 (6.6); 1.6353 (6.6); -0.0002 (9.5); -0.0084 (0.3) | 432.0 | |
I-137 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4850 (3.4); 9.4675 (3.6); 9.0375 (5.3); 9.0361 (5.7); 9.0318 (5.7); 9.0302 (5.5); 9.0159 (1.0); 9.0142 (1.0); 9.0104 (1.0); 9.0086 (1.0); 9.0012 (0.8); 8.9971 (0.7); 8.9952 (0.7); 8.5512 (4.2); 8.5453 (3.8); 8.5297 (4.6); 8.5238 (4.6); 8.5057 (0.8); 8.5001 (0.8); 8.4879 (0.6); 8.4821 (0.5); 8.4666 (0.6); 8.4607 (0.6); 8.3160 (1.0); 8.2861 (5.2); 8.2823 (9.4); 8.2785 (5.6); 8.2742 (1.3); 8.2703 (1.6); 8.2664 (1.0); 8.2546 (0.4); 8.2271 (15.2); 8.2206 (2.8); 8.2016 (2.2); 8.1931 (4.6); 8.1885 (7.4); 8.1845 (5.7); 8.1798 (1.4); 8.1755 (0.8); 8.1673 (0.8); 8.1625 (1.2); 8.1586 (0.9); 8.1419 (5.5); 8.1376 (8.9); 8.1331 (6.1); 8.0207 (5.3); 8.0159 (1.4); 7.9991 (5.0); 7.9947 (1.3); 7.9780 (0.8); 7.9567 (0.8); 7.7105 (0.4); 6.1552 (0.5); 6.1377 (2.6); 6.1202 (4.1); 6.1128 (0.9); 6.1028 (2.6); 6.0853 (0.6); 3.4895 (0.4); 3.3645 (23.2); 3.3347 (14.4); 3.3178 (49.7); 3.2524 (1.6); 3.1416 (0.4); 3.0247 (1.1); 2.8907 (0.4); 2.6897 (0.6); 2.6803 (0.7); 2.6757 (1.5); 2.6711 (2.1); 2.6666 (1.5); 2.6620 (0.7); 2.5971 (0.5); 2.5247 (5.6); 2.5200 (8.8); 2.5113 (123.2); 2.5068 (252.7); 2.5022 (334.2); 2.4976 (239.4); 2.4931 (113.6); 2.3382 (0.8); 2.3336 (1.6); 2.3290 (2.2); 2.3245 (1.6); 2.3198 (0.8); 2.0747 (3.1); 2.0089 (0.4); 1.9897 (0.4); 1.6604 (16.0); 1.6430 (16.0); 1.2725 (1.1); 1.2582 (1.6); 1.2424 (2.5); 1.2348 (2.4); 0.8540 (0.6); 0.1459 (1.9); 0.0214 (0.5); 0.0207 (0.5); 0.0177 (0.8); 0.0147 (1.0); 0.0080 (17.9); -0.0002 (501.8); -0.0086 (17.2); -0.0245 (0.5); -0.0289 (0.4); -0.1496 (2.0) | 527.2 | |
I-138 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.3814 (2.4); 9.3995 (1.4); 9.3816 (1.4); 8.6943 (2.4); 8.6884 (2.4); 8.2520 (2.6); 8.2480 (5.4); 8.2443 (2.6); 8.2323 (1.6); 8.2258 (1.6); 8.1360 (1.0); 8.1310 (4.2); 8.1278 (6.2); 8.1242 (4.2); 8.1193 (1.2); 8.1144 (7.2); 7.7789 (2.8); 7.7569 (2.6); 5.9533 (1.0); 5.9358 (1.6); 5.9182 (1.0); 3.3256 (31.5); 3.3131 (17.5); 2.6891 (0.4); 2.6756 (0.4); 2.6710 (0.6); 2.6664 (0.4); 2.5246 (1.6); 2.5199 (2.3); 2.5112 (34.4); 2.5067 (71.4); 2.5021 (94.5); 2.4975 (67.6); 2.4929 (32.2); 2.3335 (0.4); 2.3289 (0.6); 2.3243 (0.4); 2.1049 (16.0); 2.0756 (10.9); 1.6310 (5.8); 1.6136 (5.8); 0.0080 (0.4); -0.0002 (14.0); -0.0085 (0.4) | 463.1 | |
I-139 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.6368 (4.7); 9.3984 (2.7); 9.3806 (2.8); 8.7140 (5.0); 8.7085 (4.9); 8.7075 (4.9); 8.2611 (3.4); 8.2540 (6.5); 8.2499 (8.3); 8.2460 (4.7); 8.2390 (3.7); 8.2324 (3.6); 8.1331 (2.0); 8.1281 (8.3); 8.1249 (11.6); 8.1215 (8.4); 8.1154 (15.2); 7.7757 (5.3); 7.7534 (4.9); 5.9699 (0.4); 5.9526 (1.9); 5.9351 (3.0); 5.9175 (1.9); 5.9000 (0.4); 3.3276 (57.6); 3.3119 (33.8); 2.6761 (0.5); 2.6716 (0.7); 2.6669 (0.6); 2.5251 (2.1); 2.5204 (3.0); 2.5117 (43.6); 2.5072 (90.5); 2.5026 (119.2); 2.4979 (84.3); 2.4934 (39.3); 2.3339 (0.5); 2.3294 (0.7); 2.3248 (0.5); 1.8366 (0.5); 1.8210 (1.6); 1.8059 (2.1); 1.7905 (1.7); 1.7748 (0.6); 1.6304 (10.8); 1.6130 (10.8); 0.8659 (9.1); 0.8515 (16.0); 0.0080 (0.4); -0.0002 (14.7); -0.0086 (0.4 | 489.1 | |
I-140 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4392 (1.2); 9.4212 (1.2); 8.6163 (2.2); 8.6152 (2.4); 8.6100 (2.4); 8.6087 (2.3); 8.2936 (1.8); 8.2897 (3.4); 8.2859 (2.0); 8.1855 (2.8); 8.1823 (3.0); 8.1787 (3.4); 8.1636 (2.1); 8.1571 (2.1); 8.1440 (2.1); 8.1397 (3.0); 8.1351 (1.6); 7.8516 (2.6); 7.8503 (2.6); 7.8297 (2.3); 7.8283 (2.3); 6.0154 (0.9); 5.9978 (1.4); 5.9802 (0.9); 5.7590 (3.7); 3.3256 (30.6); 3.3233 (18.6); 3.3096 (0.5); 2.6712 (0.4); 2.5248 (1.1); 2.5201 (1.5); 2.5114 (24.4); 2.5069 (51.2); 2.5023 (68.0); 2.4977 (48.8); 2.4931 (23.3); 2.3284 (16.0); 1.6176 (5.1); 1.6002 (5.1); -0.0002 (10.6); -0.0086 (0.3) | 454.2 | |
I-141 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.5968 (5.7); 9.5208 (3.0); 9.5032 (3.1); 9.1139 (4.8); 9.1126 (5.1); 9.1082 (5.1); 9.1067 (4.9); 8.5850 (3.6); 8.5791 (3.4); 8.5636 (3.8); 8.5577 (3.9); 8.3061 (4.6); 8.3023 (8.8); 8.2984 (5.1); 8.2811 (0.4); 8.2287 (16.0); 8.2117 (4.6); 8.2070 (7.0); 8.2030 (4.9); 8.1919 (0.7); 8.1802 (0.4); 8.1469 (5.4); 8.1425 (7.7); 8.1380 (4.5); 8.1292 (0.5); 8.0580 (5.4); 8.0566 (5.5); 8.0367 (5.2); 8.0352 (5.2); 7.8327 (0.4); 7.8240 (4.3); 7.8185 (1.7); 7.8114 (4.8); 7.8063 (2.7); 7.8011 (5.1); 7.7941 (1.8); 7.7885 (4.8); 7.7797 (0.4); 7.2664 (0.5); 7.2577 (5.5); 7.2520 (1.6); 7.2448 (0.8); 7.2403 (1.9); 7.2354 (8.8); 7.2305 (1.9); 7.2260 (0.7); 7.2187 (1.6); 7.2130 (5.2); 7.2041 (0.4); 6.1873 (0.5); 6.1697 (2.0); 6.1522 (3.2); 6.1347 (2.1); 6.1176 (0.4); 5.7590 (7.4); 3.3264 (140.3); 3.3194 (40.7); 2.6759 (1.7); 2.6711 (1.8); 2.6665 (1.2); 2.6620 (0.6); 2.5247 (4.9); 2.5200 (7.2); 2.5112 (99.8); 2.5067 (206.6); 2.5021 (272.6); 2.4975 (193.4); 2.4929 (90.3); 2.3381 (0.5); 2.3336 (1.2); 2.3290 (1.7); 2.3244 (1.2); 2.3200 (0.5); 1.6854 (11.8); 1.6679 (12.1); 1.6484 (0.8); 1.2469 (1.5); 1.2341 (3.2); 1.2186 (1.1); 1.2059 (0.6); 1.1937 (0.6); 1.1895 (0.6); 1.1772 (0.4); 0.8536 (0.6); 0.0081 (1.0); -0.0001 (33.6); -0.0085 (0.9) | 543.1 | |
I-142 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4897 (1.2); 9.4719 (1.2); 9.0452 (2.2); 9.0434 (2.4); 9.0397 (2.4); 9.0379 (2.2); 8.5487 (2.0); 8.5432 (1.9); 8.5272 (2.1); 8.5216 (2.1); 8.3165 (1.9); 8.3126 (3.6); 8.3088 (2.1); 8.2227 (1.9); 8.2181 (2.8); 8.2141 (1.9); 8.1537 (2.2); 8.1493 (3.1); 8.1448 (1.7); 8.0312 (2.5); 8.0293 (2.4); 8.0096 (2.4); 8.0078 (2.3); 6.1272 (1.0); 6.1097 (1.5); 6.0921 (1.0); 5.7591 (4.1); 3.9284 (0.8); 3.3680 (0.7); 3.3283 (20.2); 3.3265 (19.6); 2.5253 (0.8); 2.5206 (1.2); 2.5119 (17.8); 2.5074 (36.4); 2.5028 (47.7); 2.4981 (33.7); 2.4936 (15.6); 2.3476 (16.0); 2.3344 (0.4); 2.3296 (0.4); 1.6297 (5.2); 1.6123 (5.2); -0.0002 (7.8) | 445.2 | |
I-143 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4432 (2.2); 9.4254 (2.2); 8.6009 (4.6); 8.5935 (4.7); 8.3163 (1.0); 8.2603 (3.3); 8.2565 (6.5); 8.2527 (3.8); 8.1612 (3.4); 8.1574 (16.0); 8.1528 (4.6); 8.1399 (4.5); 8.1356 (5.7); 8.1310 (2.7); 8.0624 (1.4); 8.0549 (1.3); 8.0419 (1.8); 8.0401 (2.2); 8.0326 (2.1); 8.0197 (2.0); 8.0122 (1.8); 7.9255 (2.7); 7.9158 (2.8); 7.9029 (2.0); 7.8934 (2.0); 5.9694 (0.4); 5.9520 (1.7); 5.9346 (2.7); 5.9171 (1.7); 5.8993 (0.4); 3.3242 (134.4); 3.3168 (31.5); 2.6799 (0.7); 2.6755 (1.6); 2.6709 (2.2); 2.6663 (1.6); 2.6617 (0.8); 2.5244 (5.9); 2.5197 (8.5); 2.5110 (125.8); 2.5065 (263.0); 2.5019 (350.4); 2.4973 (250.5); 2.4928 (118.1); 2.3378 (0.6); 2.3333 (1.5); 2.3288 (2.1); 2.3242 (1.5); 2.3199 (0.7); 1.6385 (10.4); 1.6211 (10.3); 0.0081 (1.1); -0.0001 (38.8); -0.0084 (1.1) | 424.1 | |
I-144 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4557 (3.0); 9.4380 (3.1); 8.6464 (5.9); 8.6450 (6.6); 8.6400 (6.6); 8.6385 (6.5); 8.3157 (0.6); 8.2712 (4.8); 8.2674 (9.6); 8.2635 (5.6); 8.2212 (5.4); 8.2147 (5.1); 8.1993 (6.1); 8.1928 (6.1); 8.1814 (16.0); 8.1656 (4.4); 8.1608 (7.8); 8.1569 (6.1); 8.1431 (6.4); 8.1388 (8.0); 8.1342 (4.1); 7.8991 (7.0); 7.8976 (7.2); 7.8773 (6.2); 7.8758 (6.5); 6.0297 (0.5); 6.0126 (2.3); 5.9951 (3.7); 5.9776 (2.3); 5.9602 (0.5); 4.0381 (0.7); 4.0203 (0.8); 3.3268 (171.0); 3.3188 (43.5); 2.6807 (0.4); 2.6762 (0.8); 2.6716 (1.1); 2.6670 (0.8); 2.6627 (0.4); 2.5252 (2.8); 2.5205 (4.1); 2.5118 (63.4); 2.5073 (133.6); 2.5027 (178.7); 2.4980 (127.4); 2.4935 (59.8); 2.3386 (0.4); 2.3341 (0.8); 2.3295 (1.1); 2.3249 (0.8); 2.3206 (0.4); 1.9893 (3.5); 1.6400 (14.0); 1.6226 (13.9); 1.2497 (0.3); 1.2355 (0.5); 1.1932 (1.0); 1.1753 (2.0); 1.1576 (1.0); -0.0001 (6.1) | 440.0 | |
I-145 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4051 (1.0); 9.3872 (1.0); 8.2525 (3.4); 8.2485 (3.4); 8.2449 (3.5); 8.1356 (5.1); 8.1319 (4.8); 8.0992 (4.7); 7.7535 (1.5); 7.7312 (2.5); 7.6681 (1.7); 7.6606 (1.6); 7.6458 (1.0); 7.6383 (1.1); 5.8959 (0.7); 5.8784 (1.1); 5.8608 (0.7); 5.7571 (0.7); 3.9554 (1.2); 3.8859 (16.0); 3.7314 (0.4); 3.6726 (0.8); 3.3256 (7.2); 3.3177 (12.1); 2.5255 (0.5); 2.5208 (0.8); 2.5121 (11.5); 2.5076 (24.0); 2.5030 (31.9); 2.4984 (22.8); 2.4939 (10.8); 1.9099 (1.2); 1.6265 (4.3); 1.6091 (4.4); -0.0002 (1.1) | 436.1 | |
I-146 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5372 (2.1); 9.5198 (2.1); 9.2270 (5.7); 9.2242 (5.6); 9.0386 (5.5); 9.0245 (5.7); 8.3213 (3.4); 8.3175 (6.5); 8.3136 (3.7); 8.2775 (10.7); 8.2306 (3.4); 8.2261 (5.1); 8.2220 (3.5); 8.1574 (3.7); 8.1530 (5.5); 8.1485 (3.0); 8.0063 (4.0); 8.0032 (4.0); 7.9923 (3.9); 7.9892 (3.8); 6.2734 (0.3); 6.2565 (1.6); 6.2391 (2.6); 6.2217 (1.6); 6.2044 (0.4); 5.7572 (16.0); 4.0385 (0.9); 4.0207 (1.0); 4.0029 (0.3); 3.3277 (42.9); 2.6726 (0.4); 2.5261 (1.1); 2.5213 (1.7); 2.5127 (22.8); 2.5082 (46.2); 2.5036 (60.4); 2.4990 (42.2); 2.4944 (19.2); 2.3304 (0.4); 2.0762 (6.8); 1.9899 (4.3); 1.9096 (1.4); 1.6696 (10.1); 1.6522 (10.0); 1.1934 (1.2); 1.1756 (2.4); 1.1578 (1.2); -0.0002 (2.3) | 407.1 | |
I-147 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.5544 (3.2); 9.5374 (3.3); 8.3386 (5.2); 8.3348 (10.0); 8.3310 (5.8); 8.3159 (1.3); 8.2438 (5.2); 8.2391 (8.1); 8.2351 (5.4); 8.2086 (16.0); 8.1652 (5.6); 8.1607 (8.4); 8.1563 (4.7); 7.8031 (9.3); 7.7943 (14.2); 7.7635 (14.3); 7.7548 (9.2); 6.0950 (0.5); 6.0777 (2.6); 6.0605 (4.0); 6.0432 (2.6); 6.0260 (0.5); 4.0376 (0.7); 4.0199 (0.7); 3.3316 (46.8); 3.3236 (138.1); 2.6800 (0.9); 2.6755 (1.9); 2.6709 (2.6); 2.6663 (1.9); 2.6617 (0.9); 2.5245 (6.8); 2.5197 (10.6); 2.5110 (151.8); 2.5065 (314.8); 2.5019 (417.8); 2.4973 (297.9); 2.4928 (139.9); 2.3379 (0.8); 2.3334 (1.8); 2.3287 (2.5); 2.3242 (1.8); 2.3196 (0.8); 2.0746 (0.8); 1.9889 (3.1); 1.6407 (15.9); 1.6232 (15.9); 1.2495 (0.6); 1.2362 (1.1); 1.1928 (1.0); 1.1750 (1.9); 1.1572 (0.9); 0.0080 (0.4); -0.0002 (14.6); -0.0086 (0.4) | 412.1 | |
I-148 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4745 (3.4); 9.4568 (3.4); 8.8182 (6.0); 8.8055 (6.1); 8.3245 (8.6); 8.3164 (0.6); 8.2623 (4.8); 8.2586 (9.1); 8.2549 (5.3); 8.2405 (16.0); 8.1655 (3.9); 8.1611 (8.0); 8.1571 (5.7); 8.1457 (6.0); 8.1415 (8.1); 8.1371 (3.5); 7.9744 (5.0); 7.9712 (4.9); 7.9618 (4.8); 7.9585 (4.7); 6.0708 (0.6); 6.0535 (2.6); 6.0361 (4.0); 6.0186 (2.6); 6.0016 (0.5); 4.0559 (0.4); 4.0380 (1.4); 4.0203 (1.4); 4.0024 (0.5); 3.3259 (86.4); 3.3197 (43.5); 2.6762 (0.8); 2.6716 (1.1); 2.6672 (0.8); 2.5250 (2.9); 2.5200 (4.4); 2.5115 (66.5); 2.5071 (135.0); 2.5026 (177.0); 2.4981 (125.8); 2.4937 (59.2); 2.3338 (0.8); 2.3294 (1.1); 2.3250 (0.8); 1.9893 (5.8); 1.9037 (0.4); 1.6483 (15.2); 1.6309 (15.1); 1.1930 (1.5); 1.1752 (3.1); 1.1574 (1.5); -0.0001 (4.5) | 431.1 | |
I-149 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1942 (0.8); 9.1773 (0.8); 8.3158 (0.6); 8.1858 (4.1); 7.7968 (2.4); 7.7880 (3.8); 7.7589 (3.9); 7.7502 (2.5); 7.6429 (1.3); 7.6385 (2.0); 7.6342 (1.4); 7.4643 (1.2); 7.4606 (2.1); 7.4570 (1.2); 7.3428 (1.2); 7.3383 (2.0); 7.3340 (1.1); 6.0231 (0.7); 6.0058 (1.0); 5.9885 (0.7); 3.3255 (222.9); 2.6799 (0.5); 2.6755 (1.1); 2.6709 (1.6); 2.6663 (1.1); 2.6618 (0.5); 2.5244 (3.8); 2.5197 (5.6); 2.5110 (87.9); 2.5065 (183.4); 2.5019 (243.7); 2.4973 (173.3); 2.4928 (81.4); 2.3379 (0.5); 2.3334 (1.1); 2.3288 (1.5); 2.3241 (1.1); 2.3198 (0.5); 2.0157 (0.4); 2.0073 (0.4); 1.9948 (0.9); 1.9823 (0.5); 1.9741 (0.4); 1.6115 (4.2); 1.5940 (4.2); 1.3978 (16.0); 1.0229 (0.4); 1.0121 (1.4); 1.0064 (1.5); 1.0023 (0.7); 0.9960 (0.7); 0.9910 (1.5); 0.9854 (1.5); 0.9752 (0.6); 0.7848 (0.6); 0.7746 (1.5); 0.7722 (1.2); 0.7690 (1.4); 0.7620 (1.5); 0.7570 (1.5); 0.7458 (0.5); -0.0002 (8.6) | 374.2 | |
I-150 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 11.7091 (2.4); 9.4277 (3.5); 9.4101 (3.6); 8.8125 (6.3); 8.8064 (6.2); 8.3573 (4.0); 8.3508 (3.8); 8.3351 (4.5); 8.3286 (4.4); 8.3163 (0.5); 8.2525 (4.8); 8.2487 (9.0); 8.2450 (5.4); 8.1569 (16.0); 8.1414 (3.5); 8.1367 (8.5); 8.1328 (7.2); 8.1291 (7.6); 8.1249 (8.4); 8.1203 (3.2); 7.9125 (6.6); 7.8904 (6.0); 6.0246 (0.5); 6.0074 (2.4); 5.9900 (3.7); 5.9725 (2.4); 5.9552 (0.5); 3.3263 (91.2); 3.3091 (40.3); 2.6761 (0.9); 2.6716 (1.2); 2.6670 (0.9); 2.6626 (0.4); 2.5249 (3.8); 2.5115 (74.2); 2.5071 (147.7); 2.5026 (193.0); 2.4981 (138.4); 2.4937 (66.1); 2.3340 (0.9); 2.3295 (1.2); 2.3248 (0.8); 2.0752 (0.6); 1.9093 (0.4); 1.6489 (13.8); 1.6315 (13.7); 0.0081 (1.3); -0.0001 (32.7); -0.0084 (1.1) | 517.2 | |
I-151 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3855 (3.0); 9.3674 (3.1); 8.5394 (8.2); 8.5332 (8.8); 8.3490 (1.8); 8.3429 (1.6); 8.3280 (2.2); 8.3251 (2.3); 8.3220 (2.2); 8.3190 (1.9); 8.3160 (1.3); 8.3042 (1.8); 8.2979 (1.6); 8.2270 (16.0); 8.1608 (3.8); 8.1570 (9.0); 8.1532 (6.2); 8.1443 (5.8); 8.1396 (8.4); 8.1355 (4.2); 8.0540 (5.3); 8.0495 (7.2); 8.0453 (4.5); 5.3864 (0.5); 5.3689 (2.2); 5.3512 (3.5); 5.3335 (2.3); 5.3156 (0.5); 3.3274 (280.4); 3.3102 (41.5); 2.6803 (0.6); 2.6758 (1.2); 2.6712 (1.6); 2.6666 (1.2); 2.6623 (0.6); 2.5247 (4.2); 2.5200 (6.5); 2.5113 (95.0); 2.5068 (197.3); 2.5022 (261.4); 2.4976 (185.2); 2.4931 (86.3); 2.3382 (0.5); 2.3337 (1.1); 2.3291 (1.6); 2.3245 (1.1); 2.3200 (0.5); 1.6316 (13.8); 1.6140 (13.8); 0.0080 (1.0); -0.0002 (32.8); -0.0085 (0.9) | 442.2 | |
I-152 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.2865 (0.7); 9.4279 (1.0); 9.4100 (1.0); 8.3482 (1.7); 8.3468 (1.8); 8.3419 (1.8); 8.3402 (1.7); 8.2709 (1.5); 8.2671 (2.8); 8.2632 (1.6); 8.1627 (1.3); 8.1580 (2.3); 8.1540 (1.7); 8.1369 (2.0); 8.1298 (5.6); 7.8843 (0.8); 7.8778 (0.6); 7.8623 (2.0); 7.8558 (2.0); 7.8372 (2.4); 7.8359 (2.5); 7.8154 (0.9); 7.8138 (0.9); 5.9681 (0.7); 5.9505 (1.1); 5.9329 (0.7); 3.3296 (16.5); 3.3174 (12.0); 3.0898 (13.0); 2.5260 (0.5); 2.5211 (0.8); 2.5125 (9.9); 2.5080 (20.0); 2.5035 (26.0); 2.4989 (18.3); 2.4943 (8.4); 2.0754 (16.0); 1.6385 (4.0); 1.6211 (3.9); 1.2345 (0.7); -0.0002 (6.0) | 499.2 | |
I-153 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.7622 (4.9); 9.4133 (2.5); 9.3955 (2.6); 8.6754 (4.2); 8.6691 (4.3); 8.2505 (5.7); 8.2407 (2.5); 8.2341 (2.2); 8.2185 (2.5); 8.2120 (2.5); 8.1366 (5.9); 8.1305 (15.8); 7.8362 (4.6); 7.8142 (4.2); 5.9936 (0.4); 5.9764 (1.6); 5.9589 (2.6); 5.9413 (1.7); 5.9237 (0.4); 3.9942 (16.0); 3.3306 (44.0); 3.3141 (25.4); 2.8312 (0.4); 2.6677 (0.7); 2.5075 (53.5); 2.5035 (68.7); 2.4994 (52.2); 2.3305 (0.4); 1.6385 (9.5); 1.6211 (9.4); -0.0002 (56.0); -0.0082 (2.3) | 488.2 | |
I-154 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.4380 (5.8); 9.4095 (2.6); 9.3915 (2.7); 8.7403 (5.2); 8.7346 (5.0); 8.3159 (0.8); 8.2552 (4.2); 8.2531 (4.8); 8.2491 (10.6); 8.2454 (4.7); 8.2333 (3.7); 8.2267 (3.7); 8.1740 (0.5); 8.1418 (3.1); 8.1370 (7.0); 8.1318 (16.0); 8.1269 (5.8); 8.1227 (6.8); 8.1180 (2.9); 7.9428 (0.3); 7.8204 (5.4); 7.7982 (4.9); 5.9981 (0.4); 5.9809 (1.9); 5.9633 (3.0); 5.9457 (1.9); 5.9281 (0.4); 3.3273 (257.5); 3.3109 (35.5); 2.6803 (0.8); 2.6758 (1.8); 2.6712 (2.4); 2.6667 (1.7); 2.6622 (0.8); 2.5247 (7.2); 2.5200 (10.4); 2.5113 (140.6); 2.5068 (288.5); 2.5022 (378.6); 2.4976 (267.2); 2.4931 (124.8); 2.3382 (0.8); 2.3336 (1.7); 2.3290 (2.4); 2.3244 (1.7); 2.3199 (0.8); 1.7673 (0.5); 1.7467 (3.0); 1.7376 (12.1); 1.7286 (12.1); 1.7195 (3.1); 1.6991 (0.5); 1.6343 (11.1); 1.6169 (11.0); 1.2697 (0.4); 1.2179 (0.3); 0.1459 (1.8); 0.0080 (14.1); -0.0002 (444.0); -0.0085 (13.8); -0.0208 (0.5); -0.1496 (1.8) | 514.2 | |
I-155 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 8.3856 (7.1); 8.3826 (7.4); 8.2804 (4.4); 8.2769 (4.2); 8.2661 (4.6); 8.2626 (4.4); 8.0716 (13.7); 7.8681 (6.9); 7.8538 (6.4); 6.8546 (8.4); 6.7962 (2.4); 6.6056 (2.3); 6.3773 (1.6); 6.3656 (4.8); 6.3539 (4.8); 6.3423 (1.5); 4.7334 (0.5); 4.7175 (1.6); 4.7071 (1.1); 4.7015 (1.9); 4.6914 (2.6); 4.6860 (1.0); 4.6754 (2.6); 4.6594 (0.9); 4.6129 (0.8); 4.5980 (2.6); 4.5830 (2.8); 4.5718 (2.0); 4.5569 (1.8); 4.5419 (0.6); 4.0681 (1.4); 4.0562 (4.1); 4.0443 (4.2); 4.0324 (1.4); 2.3012 (9.1); 2.1187 (0.4); 2.0770 (0.3); 2.0729 (0.5); 2.0688 (0.3); 2.0598 (0.4); 1.9848 (20.2); 1.9782 (5.2); 1.9740 (5.9); 1.9702 (33.8); 1.9661 (58.8); 1.9620 (86.1); 1.9579 (59.9); 1.9538 (30.8); 1.8551 (0.4); 1.8511 (0.5); 1.8469 (0.6); 1.8428 (0.5); 1.7483 (15.6); 1.7366 (16.0); 1.7238 (2.1); 1.7158 (2.5); 1.7084 (1.9); 1.7026 (1.5); 1.6943 (0.8); 1.2179 (4.8); 1.2060 (9.5); 1.1941 (4.8); 1.0343 (0.6); 1.0160 (6.3); 1.0127 (6.6); 1.0021 (6.2); 0.9988 (6.5); 0.9809 (0.8); 0.6104 (1.7); 0.6015 (2.2); 0.5949 (2.4); 0.5712 (0.3); 0.5416 (2.1); 0.5364 (2.0); 0.5271 (1.5) | 475.1 | |
I-156 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 8.7988 (2.1); 8.7962 (2.1); 8.3772 (1.3); 8.3736 (1.9); 8.3632 (1.3); 8.3600 (1.3); 8.2681 (0.5); 8.2539 (0.6); 8.1277 (3.8); 8.0899 (2.0); 8.0754 (3.3); 8.0358 (0.7); 7.9654 (2.3); 7.9339 (0.8); 7.9196 (0.8); 7.7854 (1.0); 7.6280 (1.0); 7.4745 (2.3); 7.3977 (0.9); 7.3482 (2.5); 6.3896 (0.4); 6.3782 (1.2); 6.3666 (1.2); 6.3552 (0.4); 6.1410 (0.6); 6.1297 (0.6); 4.0663 (2.5); 4.0544 (7.5); 4.0425 (7.5); 4.0306 (2.5); 3.6838 (0.4); 3.6732 (0.4); 3.5831 (0.4); 3.5718 (0.4); 3.0814 (11.2); 3.0510 (4.5); 2.8869 (1.6); 2.8805 (1.7); 2.8755 (1.9); 2.8714 (1.7); 2.2962 (34.3); 2.0964 (3.0); 2.0749 (0.5); 2.0709 (0.7); 2.0668 (0.5); 1.9831 (41.8); 1.9761 (7.4); 1.9680 (48.6); 1.9640 (84.1); 1.9599 (122.9); 1.9559 (86.2); 1.9518 (44.6); 1.8526 (0.3); 1.8490 (0.5); 1.8448 (0.7); 1.8408 (0.6); 1.8367 (0.3); 1.8223 (4.9); 1.8107 (5.0); 1.7571 (2.1); 1.7456 (2.1); 1.2162 (8.1); 1.2043 (16.0); 1.1924 (8.0); 1.0754 (0.3); 0.5577 (0.5); 0.5476 (0.6); 0.5368 (0.5); 0.4989 (0.4); 0.4923 (0.4); 0.4856 (0.5); 0.4790 (0.5); 0.4725 (0.4); 0.4653 (0.4); 0.3417 (0.4); 0.3340 (0.4); 0.3278 (0.3); 0.2872 (0.4); 0.2791 (0.6); 0.2723 (0.9); 0.2647 (1.1); 0.2572 (0.9); 0.2499 (0.6); 0.2414 (0.4); 0.2386 (0.4); 0.2302 (0.6); 0.2229 (0.6); 0.2163 (0.7); 0.2087 (0.5); -0.0016 (0.4); -0.1811 (0.6); -0.1892 (0.8); -0.1972 (0.9) | 485.2 | |
I-157 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 9.0327 (16.0); 8.4548 (5.9); 8.4540 (6.0); 8.4510 (6.2); 8.4501 (5.8); 7.8325 (4.7); 7.8297 (7.4); 7.8267 (4.9); 7.8011 (3.0); 7.7972 (3.0); 7.7860 (3.2); 7.7822 (3.1); 7.6933 (4.7); 7.6908 (8.6); 7.6883 (4.7); 7.4471 (4.7); 7.4441 (8.3); 7.4411 (4.6); 6.7266 (0.9); 2.9490 (0.6); 2.8797 (7.0); 2.2990 (65.2); 2.2665 (0.5); 2.0807 (0.3); 2.0766 (0.6); 2.0725 (0.8); 2.0684 (0.6); 1.9986 (0.9); 1.9903 (2.1); 1.9859 (31.8); 1.9778 (10.1); 1.9737 (10.2); 1.9699 (57.1); 1.9658 (98.9); 1.9617 (145.3); 1.9575 (99.3); 1.9534 (50.6); 1.9489 (1.3); 1.9447 (0.5); 1.8507 (0.6); 1.8466 (0.8); 1.8425 (0.6); 1.6434 (0.4); 1.6280 (9.5); 1.6163 (9.4); 1.0757 (1.3); 1.0732 (1.2); 1.0680 (5.3); 1.0648 (5.5); 1.0596 (2.4); 1.0571 (2.1); 1.0541 (5.4); 1.0508 (5.3); 1.0458 (1.4); 1.0434 (1.5); 0.7685 (0.5); 0.7646 (0.4); 0.7567 (2.8); 0.7516 (3.0); 0.7487 (6.1); 0.7450 (5.2); 0.7408 (6.1); 0.7375 (3.2); 0.7326 (2.3); 0.7207 (0.3) | 407.2 | |
I-158 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 10.6833 (7.3); 9.4272 (3.4); 9.4094 (3.5); 8.9091 (6.3); 8.9035 (6.1); 8.4466 (3.9); 8.4400 (3.7); 8.4244 (4.3); 8.4179 (4.2); 8.3162 (1.0); 8.2696 (4.8); 8.2659 (9.1); 8.2621 (5.4); 8.1553 (4.4); 8.1506 (7.7); 8.1467 (5.8); 8.1392 (16.0); 8.1237 (5.7); 8.1194 (7.9); 8.1149 (4.1); 8.0932 (5.0); 8.0879 (2.2); 8.0795 (5.6); 8.0710 (6.0); 8.0627 (2.2); 8.0573 (5.4); 8.0497 (0.6); 7.9524 (1.2); 7.8574 (6.3); 7.8352 (6.0); 7.4402 (5.5); 7.4350 (1.8); 7.4180 (10.6); 7.4010 (1.7); 7.3958 (5.3); 7.2766 (0.3); 7.2541 (0.6); 6.0225 (0.5); 6.0052 (2.3); 5.9877 (3.6); 5.9702 (2.3); 5.9526 (0.5); 3.3262 (194.2); 3.3081 (39.6); 3.2623 (0.5); 3.1453 (0.4); 2.8911 (8.4); 2.7321 (7.0); 2.7311 (7.2); 2.6759 (1.7); 2.6713 (2.3); 2.6667 (1.7); 2.6621 (0.8); 2.5248 (7.2); 2.5200 (10.8); 2.5113 (141.6); 2.5069 (287.7); 2.5023 (375.5); 2.4977 (268.6); 2.4933 (128.8); 2.3383 (0.8); 2.3337 (1.6); 2.3292 (2.3); 2.3246 (1.6); 2.3202 (0.8); 2.0749 (1.0); 1.6548 (13.2); 1.6374 (13.1); 0.1459 (0.8); 0.0079 (6.8); -0.0002 (207.1); -0.0085 (6.8); -0.1495 (0.8) | 543.1 | |
I-159 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.1139 (1.2); 9.0960 (1.2); 9.0284 (2.2); 9.0267 (2.3); 9.0230 (2.4); 9.0212 (2.1); 8.5414 (1.9); 8.5358 (1.8); 8.5199 (2.0); 8.5143 (2.0); 8.0164 (2.4); 8.0147 (2.3); 7.9949 (2.2); 7.9931 (2.1); 7.6057 (1.7); 7.6014 (2.7); 7.5970 (1.8); 7.4270 (1.6); 7.4234 (2.8); 7.4198 (1.6); 7.3291 (1.6); 7.3248 (2.7); 7.3204 (1.5); 6.0602 (1.0); 6.0428 (1.5); 6.0251 (1.0); 4.0380 (0.6); 4.0202 (0.5); 3.3262 (51.1); 2.6760 (0.4); 2.6715 (0.5); 2.6669 (0.4); 2.5251 (1.4); 2.5204 (2.0); 2.5116 (28.6); 2.5072 (59.3); 2.5026 (78.4); 2.4980 (55.5); 2.4935 (25.8); 2.3374 (16.0); 2.3250 (0.5); 2.0029 (0.6); 1.9944 (0.6); 1.9892 (2.8); 1.9820 (1.2); 1.9694 (0.6); 1.9612 (0.6); 1.6044 (5.5); 1.5870 (5.4); 1.2342 (0.4); 1.1931 (0.7); 1.1753 (1.4); 1.1575 (0.7); 1.0181 (0.6); 1.0072 (1.9); 1.0016 (2.0); 0.9975 (0.9); 0.9914 (0.9); 0.9862 (2.0); 0.9807 (2.0); 0.9706 (0.7); 0.7720 (0.9); 0.7616 (2.0); 0.7593 (1.7); 0.7561 (1.9); 0.7492 (2.0); 0.7444 (2.0); 0.7330 (0.7); -0.0002 (6.7) | 407.3 | |
I-160 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 9.1666 (0.4); 9.1550 (0.4); 9.0552 (0.7); 9.0544 (0.7); 9.0517 (0.7); 9.0508 (0.7); 8.5739 (0.6); 8.5702 (0.5); 8.5596 (0.6); 8.5559 (0.6); 8.2349 (1.7); 8.0696 (0.7); 8.0688 (0.7); 8.0554 (0.7); 8.0545 (0.7); 7.7163 (0.6); 7.7137 (1.0); 7.7111 (0.6); 7.6725 (0.6); 7.6696 (0.9); 7.6669 (0.6); 7.5624 (0.6); 7.5594 (1.0); 7.5564 (0.5); 6.0511 (0.5); 4.0357 (0.4); 4.0238 (0.4); 3.3091 (35.4); 2.5218 (0.4); 2.5188 (0.4); 2.5157 (0.4); 2.5068 (10.8); 2.5038 (22.6); 2.5008 (31.0); 2.4978 (22.9); 2.4949 (10.9); 1.9880 (1.9); 1.6390 (1.9); 1.6274 (1.9); 1.3980 (0.3); 1.2794 (16.0); 1.1868 (0.5); 1.1749 (1.0); 1.1631 (0.5); -0.0001 (1.8) | 409.2 | |
I-161 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6492 (3.3); 9.6318 (3.4); 9.0777 (5.9); 9.0758 (6.4); 9.0722 (6.4); 9.0702 (6.1); 8.6235 (6.5); 8.5881 (5.7); 8.5826 (5.4); 8.5667 (6.0); 8.5611 (6.0); 8.4814 (5.7); 8.3981 (5.6); 8.3967 (5.6); 8.3128 (1.7); 8.2604 (16.0); 8.0942 (6.8); 8.0923 (6.7); 8.0727 (6.2); 8.0708 (6.4); 6.1740 (0.5); 6.1569 (2.4); 6.1396 (3.8); 6.1222 (2.4); 6.1048 (0.5); 3.3751 (41.7); 3.3144 (246.9); 2.6795 (1.2); 2.6749 (2.6); 2.6703 (3.6); 2.6657 (2.6); 2.6612 (1.2); 2.5239 (10.4); 2.5192 (15.1); 2.5105 (192.1); 2.5059 (393.4); 2.5013 (530.3); 2.4967 (389.4); 2.4921 (187.4); 2.3375 (1.1); 2.3328 (2.4); 2.3282 (3.4); 2.3236 (2.4); 2.3190 (1.1); 2.0729 (1.2); 1.6743 (14.2); 1.6569 (14.2); 0.1460 (1.6); 0.0081 (13.7); -0.0002 (445.3); -0.0085 (13.4); -0.0194 (0.5); -0.1495 (1.6) | 465.2 | |
I-162 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.0102 (5.6); 9.0084 (6.2); 9.0047 (6.6); 9.0028 (6.6); 8.9869 (2.8); 8.9726 (1.4); 8.5050 (4.7); 8.4994 (4.5); 8.4835 (5.1); 8.4779 (5.0); 8.3158 (1.2); 8.2394 (4.5); 8.2356 (8.4); 8.2318 (5.2); 8.2250 (16.0); 8.1458 (4.3); 8.1412 (7.7); 8.1369 (5.0); 8.1092 (5.2); 8.1052 (6.8); 8.1006 (3.9); 8.0392 (5.8); 8.0375 (5.8); 8.0177 (5.3); 8.0159 (5.4); 3.7736 (1.4); 3.7569 (4.1); 3.7418 (4.6); 3.7260 (2.0); 3.5949 (3.9); 3.5785 (6.9); 3.5611 (2.6); 3.3274 (509.9); 2.6802 (0.9); 2.6758 (2.0); 2.6712 (2.8); 2.6667 (2.0); 2.6622 (0.9); 2.5247 (8.9); 2.5199 (13.4); 2.5113 (168.8); 2.5068 (343.5); 2.5023 (450.2); 2.4977 (321.6); 2.4932 (153.1); 2.3380 (0.9); 2.3336 (2.0); 2.3291 (2.8); 2.3246 (2.0); 0.1459 (1.3); 0.0080 (10.8); -0.0001 (323.8); -0.0085 (11.0); -0.1496 (1.3) | 431.1 | |
I-163 | 1H-NMR(600.4 MHz, d 6-DMSO): δ= 10.6902 (5.8); 9.4349 (3.3); 9.4233 (3.5); 8.7287 (5.4); 8.7244 (5.5); 8.2874 (3.0); 8.2831 (2.9); 8.2727 (3.2); 8.2684 (3.3); 8.2155 (3.6); 8.2131 (7.2); 8.2108 (4.8); 8.1287 (3.3); 8.1256 (6.3); 8.1229 (4.1); 8.0836 (4.0); 8.0807 (6.3); 8.0782 (4.0); 7.8063 (5.5); 7.7917 (5.3); 5.9021 (0.5); 5.8907 (2.2); 5.8791 (3.5); 5.8675 (2.3); 5.8558 (0.5); 3.3103 (82.9); 3.3040 (33.9); 2.6168 (0.4); 2.6138 (0.6); 2.6108 (0.5); 2.5227 (1.0); 2.5198 (1.4); 2.5167 (1.4); 2.5047 (71.2); 2.5018 (100.3); 2.4988 (77.1); 2.3887 (0.4); 2.3857 (0.6); 2.3827 (0.4); 2.0861 (16.0); 1.8250 (0.6); 1.8139 (1.5); 1.8095 (0.9); 1.8045 (2.4); 1.8002 (1.0); 1.7953 (1.4); 1.7931 (1.4); 1.7839 (0.7); 1.6683 (11.9); 1.6567 (12.0); 0.8893 (0.4); 0.8787 (1.8); 0.8740 (6.7); 0.8680 (7.6); 0.8607 (15.1); -0.0001 (0.7) | 557.1 | |
I-164 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4131 (1.3); 9.3952 (1.3); 8.3156 (0.5); 8.2772 (2.0); 8.2735 (3.5); 8.2697 (2.1); 8.2454 (1.9); 8.2393 (1.8); 8.1606 (1.9); 8.1560 (3.0); 8.1520 (2.2); 8.1276 (2.4); 8.1232 (3.3); 8.1187 (1.8); 8.1117 (5.8); 7.8251 (0.8); 7.8185 (0.8); 7.8031 (1.5); 7.7966 (1.5); 7.7594 (2.1); 7.7376 (1.0); 5.9608 (0.9); 5.9433 (1.3); 5.9258 (0.8); 4.0556 (1.5); 4.0378 (4.0); 4.0200 (4.0); 4.0023 (1.6); 3.8546 (0.7); 3.8511 (0.8); 3.8018 (0.8); 3.7985 (0.8); 3.7725 (0.8); 3.6694 (0.7); 3.6657 (0.7); 3.6463 (0.7); 3.5931 (0.5); 3.5087 (0.4); 3.4824 (0.4); 3.3921 (1.0); 3.3701 (0.6); 3.3564 (0.4); 3.3425 (0.4); 3.3346 (0.5); 3.3290 (0.8); 3.3110 (15.6); 3.2771 (0.5); 3.2664 (0.3); 3.2594 (0.5); 3.2487 (0.3); 3.2436 (0.4); 3.2261 (0.4); 3.1165 (0.5); 3.1046 (0.5); 3.0983 (0.5); 3.0863 (0.5); 2.7774 (4.7); 2.7390 (8.6); 2.6897 (0.4); 2.6735 (9.1); 2.6351 (4.6); 2.6243 (0.6); 2.5249 (4.0); 2.5200 (6.3); 2.5114 (68.3); 2.5070 (136.0); 2.5025 (176.1); 2.4979 (125.0); 2.4934 (59.0); 2.3384 (0.4); 2.3339 (0.8); 2.3293 (1.0); 2.3248 (0.8); 2.3203 (0.4); 2.2914 (0.6); 1.9889 (16.0); 1.9799 (0.3); 1.9620 (1.4); 1.9089 (0.6); 1.6249 (5.2); 1.6076 (5.2); 1.2443 (0.5); 1.2352 (0.7); 1.1929 (5.1); 1.1751 (10.3); 1.1573 (5.1); 1.1096 (0.5); 1.0918 (0.9); 1.0740 (0.4); 1.0127 (0.6); 0.9950 (0.7); 0.1459 (0.5); 0.0079 (4.6); -0.0002 (129.1); -0.0085 (4.6); -0.1496 (0.6) | 553.1 | |
I-165 | 1H-NMR(600.1 MHz, CD3CN, 260K): δ= 8.8223 (0.8); 8.8190 (0.8); 8.3722 (0.5); 8.3687 (0.5); 8.3579 (0.5); 8.3542 (0.5); 8.2881 (0.8); 8.2714 (0.5); 8.2678 (0.4); 8.1192 (1.7); 8.0806 (1.8); 8.0648 (0.8); 7.8997 (0.6); 7.8856 (0.6); 7.1249 (0.9); 6.9138 (0.9); 6.8939 (0.8); 6.7695 (0.4); 6.6870 (1.0); 6.5936 (0.4); 6.4763 (0.5); 6.4648 (0.5); 6.1780 (0.4); 6.1664 (0.4); 2.2903 (29.8); 2.0800 (0.4); 2.0761 (0.7); 2.0720 (0.8); 2.0677 (0.7); 2.0634 (0.7); 1.9854 (4.6); 1.9773 (3.7); 1.9730 (5.1); 1.9694 (49.8); 1.9653 (92.5); 1.9612 (136.4); 1.9571 (94.9); 1.9530 (49.1); 1.9446 (1.4); 1.9357 (0.6); 1.9320 (0.4); 1.9008 (0.4); 1.8944 (0.3); 1.8866 (0.5); 1.8542 (0.3); 1.8502 (0.6); 1.8461 (0.8); 1.8420 (0.6); 1.8379 (0.3); 1.7415 (1.8); 1.7351 (0.5); 1.7299 (1.8); 1.7066 (2.0); 1.6949 (2.0); 1.0131 (0.6); 1.0033 (0.9); 0.9997 (1.3); 0.9896 (0.8); 0.9861 (0.7); 0.6605 (0.8); 0.6576 (0.8); 0.6523 (0.8); 0.6493 (0.8); 0.5643 (0.5); 0.5574 (0.4); 0.0968 (1.1); 0.0690 (13.2); 0.0053 (7.1); -0.0001 (226.7); -0.0055 (8.8); -0.0197 (0.6); -0.0233 (0.4); -0.0259 (0.6); -0.0290 (0.3); -0.1001 (1.2); -0.3567 (16.0) | 493.2 | |
I-166 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4742 (2.9); 9.4568 (2.9); 9.1700 (6.8); 9.1671 (7.0); 8.7639 (6.3); 8.7575 (7.2); 8.6712 (4.6); 8.6677 (5.1); 8.6649 (4.7); 8.6613 (4.2); 8.3142 (0.8); 8.2630 (16.0); 8.2564 (4.9); 8.1629 (3.4); 8.1583 (6.7); 8.1544 (4.9); 8.1389 (4.8); 8.1346 (6.7); 8.1300 (3.3); 6.0031 (0.5); 5.9858 (2.2); 5.9685 (3.4); 5.9511 (2.2); 5.9337 (0.5); 3.3232 (241.0); 3.3152 (43.0); 2.6755 (1.3); 2.6709 (1.8); 2.6665 (1.3); 2.6615 (0.7); 2.5244 (5.4); 2.5196 (8.2); 2.5109 (100.6); 2.5065 (203.5); 2.5019 (273.3); 2.4974 (205.3); 2.4930 (102.7); 2.3379 (0.6); 2.3333 (1.2); 2.3288 (1.8); 2.3243 (1.3); 2.0738 (0.4); 1.6576 (13.0); 1.6402 (13.0); 0.1459 (0.8); 0.0080 (6.0); -0.0002 (184.4); -0.0085 (6.6); -0.1496 (0.8) | 407.1 | |
I-167 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 11.9576 (0.3); 9.7724 (0.4); 9.4649 (3.4); 9.4473 (3.5); 8.8634 (4.9); 8.8505 (5.0); 8.3211 (0.5); 8.3082 (0.5); 8.2730 (4.8); 8.2691 (9.5); 8.2653 (5.7); 8.2438 (16.0); 8.1547 (3.0); 8.1498 (8.7); 8.1458 (8.2); 8.1440 (9.3); 8.1397 (8.6); 8.1349 (3.4); 8.1271 (6.8); 8.1255 (6.4); 7.9030 (3.5); 7.9007 (3.5); 7.8901 (3.4); 7.8878 (3.3); 7.2261 (0.6); 6.9739 (0.3); 6.1130 (0.5); 6.0958 (2.5); 6.0783 (3.9); 6.0608 (2.5); 6.0435 (0.5); 4.0392 (0.8); 4.0214 (0.8); 3.3458 (0.9); 3.3236 (35.6); 3.3163 (41.6); 2.6775 (0.4); 2.6728 (0.6); 2.6681 (0.4); 2.5264 (1.8); 2.5217 (2.6); 2.5129 (31.4); 2.5084 (64.5); 2.5038 (87.6); 2.4992 (65.6); 2.4947 (32.2); 2.3352 (0.4); 2.3307 (0.5); 2.3262 (0.4); 2.0874 (1.3); 1.9898 (3.4); 1.9795 (4.3); 1.9421 (4.5); 1.9103 (11.7); 1.6624 (14.6); 1.6450 (14.7); 1.1940 (0.9); 1.1762 (1.8); 1.1584 (0.9); 0.0081 (2.3); -0.0002 (72.7); -0.0085 (2.3) | 474.2 | |
I-168 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.4437 (2.8); 9.4259 (2.8); 8.5768 (2.7); 8.5750 (2.7); 8.5724 (2.9); 8.5647 (2.8); 8.5629 (2.8); 8.5602 (2.7); 8.3146 (0.5); 8.2681 (4.3); 8.2644 (7.2); 8.2606 (3.9); 8.1603 (4.2); 8.1560 (7.3); 8.1514 (16.0); 8.1342 (4.9); 8.1301 (6.5); 8.1254 (2.8); 8.1060 (1.7); 8.1013 (1.6); 8.0869 (3.0); 8.0823 (2.8); 8.0668 (2.2); 8.0621 (2.0); 7.8687 (4.7); 7.8483 (3.9); 7.5103 (2.4); 7.5081 (2.1); 7.4981 (2.4); 7.4959 (2.4); 7.4917 (2.4); 7.4795 (2.2); 7.4773 (1.9); 6.0849 (0.5); 6.0677 (2.0); 6.0501 (3.2); 6.0326 (2.0); 6.0154 (0.4); 3.3226 (111.6); 2.6756 (1.1); 2.6711 (1.4); 2.6667 (1.0); 2.6624 (0.5); 2.5243 (6.0); 2.5110 (93.9); 2.5066 (173.2); 2.5021 (219.2); 2.4976 (157.4); 2.4933 (74.8); 2.3379 (0.5); 2.3334 (1.1); 2.3289 (1.4); 2.3245 (1.0); 2.3201 (0.4); 2.0740 (0.4); 1.9466 (0.6); 1.9001 (0.6); 1.6483 (12.3); 1.6309 (12.1); 0.1462 (0.6); 0.0079 (7.1); -0.0002 (141.2); -0.0085 (4.5); -0.0137 (0.4); -0.1492 (0.6) | 406.2 | |
I-169 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2218 (2.5); 9.2039 (2.6); 8.5670 (2.6); 8.5643 (2.7); 8.5625 (2.5); 8.5566 (2.4); 8.5548 (2.8); 8.5522 (2.7); 8.5503 (2.4); 8.3162 (0.4); 8.1400 (12.2); 8.1041 (1.7); 8.0994 (1.7); 8.0837 (2.7); 8.0805 (2.6); 8.0791 (2.7); 8.0649 (2.2); 8.0602 (2.2); 7.8599 (4.8); 7.8394 (4.1); 7.7703 (3.7); 7.7661 (6.0); 7.7620 (4.2); 7.6602 (3.8); 7.6561 (6.4); 7.6523 (4.0); 7.5130 (4.0); 7.5082 (8.3); 7.5043 (5.3); 7.4951 (2.2); 7.4928 (2.4); 7.4887 (2.3); 7.4863 (2.2); 7.4764 (2.1); 7.4741 (2.1); 6.0421 (0.4); 6.0249 (2.0); 6.0073 (3.1); 5.9898 (2.0); 5.9722 (0.4); 4.0557 (1.2); 4.0379 (3.6); 4.0201 (3.6); 4.0023 (1.2); 3.3291 (235.5); 2.6759 (0.9); 2.6715 (1.2); 2.6670 (0.9); 2.5249 (3.9); 2.5202 (5.7); 2.5115 (74.0); 2.5071 (152.1); 2.5025 (200.7); 2.4980 (145.3); 2.4935 (70.4); 2.3385 (0.4); 2.3339 (0.9); 2.3294 (1.2); 2.3249 (0.9); 2.3202 (0.4); 1.9891 (16.0); 1.8114 (2.1); 1.7991 (6.1); 1.7916 (6.6); 1.7803 (2.8); 1.7407 (0.4); 1.6623 (0.5); 1.6356 (12.2); 1.6182 (12.9); 1.6114 (7.6); 1.6038 (6.5); 1.5908 (2.3); 1.3975 (2.9); 1.2493 (0.4); 1.2369 (0.5); 1.1929 (4.3); 1.1751 (8.6); 1.1573 (4.2); 0.1458 (0.6); 0.0079 (4.6); -0.0002 (146.1); -0.0086 (5.1); -0.1497 (0.6) | 393.3 | |
I-170 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2142 (2.5); 9.1965 (2.6); 8.6280 (4.7); 8.6226 (4.7); 8.6216 (4.6); 8.2105 (3.6); 8.2040 (3.4); 8.1887 (4.0); 8.1822 (4.0); 8.1662 (11.5); 7.8852 (5.2); 7.8842 (5.2); 7.8633 (4.5); 7.8623 (4.6); 7.7690 (3.4); 7.7648 (5.5); 7.7606 (3.9); 7.6678 (3.5); 7.6638 (6.0); 7.6599 (3.6); 7.5193 (3.6); 7.5147 (6.4); 7.5101 (3.3); 5.9902 (0.4); 5.9729 (1.8); 5.9554 (2.8); 5.9379 (1.8); 5.9205 (0.4); 5.7527 (8.4); 3.3186 (5.7); 2.5264 (0.8); 2.5217 (1.2); 2.5130 (13.9); 2.5085 (28.3); 2.5039 (38.6); 2.4993 (28.9); 2.4948 (14.3); 1.9897 (0.4); 1.8142 (1.9); 1.8018 (5.6); 1.7943 (6.0); 1.7828 (2.6); 1.7434 (0.4); 1.6649 (0.4); 1.6313 (10.7); 1.6269 (4.8); 1.6139 (16.0); 1.6067 (6.6); 1.5934 (2.1); 0.0080 (1.1); -0.0002 (33.5); -0.0085 (1.1) | 427.2 | |
I-171 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2443 (3.6); 9.2268 (3.6); 9.1602 (8.5); 9.1569 (8.7); 8.7587 (8.0); 8.7524 (9.0); 8.6618 (5.9); 8.6582 (6.4); 8.6555 (6.1); 8.6518 (5.3); 8.2521 (15.6); 7.7652 (4.9); 7.7609 (8.1); 7.7569 (5.6); 7.6541 (5.1); 7.6501 (8.7); 7.6463 (5.3); 7.5178 (5.2); 7.5132 (9.2); 7.5087 (4.8); 5.9645 (0.6); 5.9471 (2.6); 5.9298 (4.2); 5.9123 (2.7); 5.8948 (0.6); 5.7552 (0.3); 3.3236 (59.4); 2.6766 (0.4); 2.6721 (0.6); 2.6677 (0.4); 2.5257 (1.7); 2.5211 (2.5); 2.5122 (33.3); 2.5078 (68.1); 2.5032 (93.4); 2.4987 (71.3); 2.4942 (35.8); 2.3347 (0.4); 2.3301 (0.6); 2.3256 (0.4); 1.8109 (2.8); 1.7988 (7.7); 1.7912 (8.5); 1.7799 (3.6); 1.7399 (0.5); 1.6614 (0.8); 1.6461 (15.7); 1.6287 (16.0); 1.6226 (5.9); 1.6103 (8.6); 1.6027 (7.9); 1.5901 (3.2); 1.2501 (0.4); 1.2357 (0.6); 0.0081 (2.2); -0.0002 (71.2); -0.0085 (2.6) | 394.3 | |
I-172 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2548 (3.4); 9.2372 (3.5); 8.9804 (4.3); 8.9785 (4.2); 8.9766 (4.3); 8.9744 (4.5); 8.4988 (2.6); 8.4928 (2.6); 8.4771 (2.9); 8.4711 (2.8); 8.2338 (16.0); 8.0946 (4.8); 8.0731 (4.4); 7.7734 (4.5); 7.7691 (7.2); 7.7651 (5.3); 7.6780 (4.6); 7.6738 (8.0); 7.6700 (5.0); 7.5165 (4.8); 7.5119 (8.8); 7.5073 (4.6); 6.1056 (0.5); 6.0883 (2.3); 6.0708 (3.6); 6.0534 (2.3); 6.0359 (0.5); 3.3246 (36.7); 2.6735 (0.4); 2.5271 (1.2); 2.5224 (1.8); 2.5137 (21.9); 2.5091 (45.2); 2.5045 (62.4); 2.4999 (47.2); 2.4954 (23.1); 2.3314 (0.4); 1.8120 (2.6); 1.8000 (7.0); 1.7924 (7.7); 1.7811 (3.3); 1.7411 (0.4); 1.6556 (13.6); 1.6382 (13.6); 1.6211 (4.0); 1.6090 (7.7); 1.6013 (7.0); 1.5887 (2.8); 0.0081 (1.7); -0.0002 (53.2); -0.0085 (1.6) | 461.3 | |
I-173 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.3612 (6.9); 9.3555 (6.9); 9.3544 (6.7); 9.3018 (3.5); 9.2845 (3.6); 8.8517 (5.3); 8.8448 (5.1); 8.8291 (5.6); 8.8222 (5.6); 8.3141 (0.4); 8.2703 (16.0); 8.1540 (7.2); 8.1531 (7.4); 8.1316 (6.8); 8.1305 (7.0); 7.8185 (4.8); 7.8144 (7.8); 7.8102 (5.5); 7.7144 (5.0); 7.7103 (8.5); 7.7064 (5.2); 7.5215 (5.1); 7.5168 (9.3); 7.5122 (4.9); 6.1390 (0.5); 6.1218 (2.6); 6.1045 (4.0); 6.0871 (2.6); 6.0696 (0.5); 4.0384 (0.7); 4.0206 (0.7); 3.3244 (166.1); 2.6763 (0.6); 2.6717 (0.9); 2.6671 (0.6); 2.5252 (2.6); 2.5205 (3.8); 2.5118 (47.6); 2.5073 (98.1); 2.5027 (133.4); 2.4981 (100.3); 2.4936 (49.7); 2.3341 (0.6); 2.3296 (0.8); 2.3250 (0.6); 1.9891 (3.3); 1.8127 (2.7); 1.8004 (7.8); 1.7928 (8.4); 1.7815 (3.6); 1.7419 (0.5); 1.6595 (15.2); 1.6421 (15.2); 1.6311 (4.5); 1.6187 (8.3); 1.6113 (7.9); 1.5982 (2.9); 1.1933 (0.9); 1.1755 (1.8); 1.1577 (0.9); 0.1459 (0.4); 0.0080 (3.1); -0.0002 (98.8); -0.0085 (3.2); -0.1497 (0.4) | 438.2 | |
I-174 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.2250 (2.5); 9.2070 (2.6); 8.9923 (15.6); 8.9801 (16.0); 8.1610 (12.0); 7.9154 (0.4); 7.8109 (0.5); 7.7434 (3.7); 7.7392 (5.9); 7.7351 (4.2); 7.6433 (4.0); 7.6392 (10.6); 7.6355 (4.3); 7.6269 (8.2); 7.6147 (4.2); 7.5546 (0.5); 7.5126 (4.0); 7.5080 (7.0); 7.5034 (3.7); 6.0090 (0.4); 5.9915 (2.0); 5.9739 (3.0); 5.9562 (2.0); 5.9387 (0.4); 3.3187 (8.9); 2.6762 (0.4); 2.6716 (0.5); 2.6670 (0.4); 2.5419 (0.5); 2.5251 (1.6); 2.5203 (2.3); 2.5117 (30.8); 2.5072 (62.9); 2.5026 (83.6); 2.4980 (61.4); 2.4935 (30.1); 2.3341 (0.4); 2.3294 (0.5); 2.3249 (0.4); 1.8255 (0.5); 1.8179 (0.6); 1.8084 (2.3); 1.7971 (5.5); 1.7893 (6.3); 1.7782 (2.9); 1.7374 (0.3); 1.6589 (0.6); 1.6415 (12.2); 1.6241 (12.2); 1.6196 (5.4); 1.6109 (3.7); 1.6075 (6.3); 1.6018 (4.3); 1.5993 (5.1); 1.5879 (2.5); 1.4177 (0.9); 1.3996 (0.9); 0.0080 (1.6); -0.0002 (50.7); -0.0085 (1.8) | 394.2 | |
I-175 | 1H-NMR(400.2 MHz, d 6-DMSO): δ= 9.6625 (3.5); 9.6453 (3.6); 9.0583 (5.8); 9.0566 (6.4); 9.0528 (6.5); 9.0511 (6.2); 8.5839 (5.0); 8.5784 (4.9); 8.5625 (5.3); 8.5569 (5.4); 8.3896 (7.3); 8.3222 (6.5); 8.3037 (7.9); 8.3003 (7.6); 8.2622 (16.0); 8.0904 (6.5); 8.0888 (6.6); 8.0689 (5.9); 8.0673 (6.1); 6.1507 (0.6); 6.1334 (2.5); 6.1161 (4.0); 6.0988 (2.5); 6.0815 (0.5); 5.7545 (3.7); 3.3546 (0.7); 3.3267 (267.7); 2.6814 (0.4); 2.6769 (0.7); 2.6725 (1.0); 2.6678 (0.7); 2.6635 (0.4); 2.5258 (3.2); 2.5211 (4.7); 2.5124 (55.1); 2.5080 (111.5); 2.5034 (148.3); 2.4988 (110.5); 2.4944 (55.3); 2.3348 (0.6); 2.3302 (0.9); 2.3256 (0.7); 1.6664 (15.0); 1.6490 (15.0); 1.2343 (0.9); 0.1459 (0.3); 0.0080 (2.4); -0.0002 (75.5); -0.0084 (2.9); -0.1497 (0.3) | 469.2 |
實施例 | 結構 | NMR 1) | ESI 質量 [m/z] 2) |
a*-001 | 1 H NMR(400 MHz, d 6-DMSO): δ = 9.13 - 9.11 (d, 1H, NH), 8.61 (s, 1H), 8.54 (s, 1H), 8.41 (s, 1H), 7.50 (br s, 1H from NH 2), 7.05 (br s, 1H from NH 2), 4.46 - 4.39 (m, 1H), 1.36 - 1.35 (d, 3H). | 358.9 | |
a*-002 | 1 H NMR(400 MHz, d 6-DMSO): δ = 8.92 (d, 1H), 8.37 (t, 1H), 8.30 (t, 1H), 8.14 (t, 1H), 7.47 (br s, 1H), 7.04 (br s, 1H), 4.46 – 4.39 (m, 1H), 3.34 (s, 3H), 1.35 (d, 3H). | 305.1 | |
a*-003 | 1 H NMR(400 MHz, d 6-DMSO): δ = 8.72 (d, 1H), 7.90 (t, 1H), 7.79 (t, 1H), 7.53 (t, 1H), 7.42 (br s, 1H), 7.01 (br s, 1H), 4.42 – 4.38 (m, 1H), 1.83 – 1.80 (m, 2H), 1.66 – 1.63 (m, 2H), 1.34 (d, 3H). | 292.2 | |
b*-001 | 1 H NMR (400 MHz, CDCl 3): δ =11.28 (br s, 1H), 8.29 (s, 1H), 8.20 – 8.25 (m, 1H), 7.91 (s, 1H). 3) | 254.8 # | |
b*-002 | 1 H NMR (400 MHz, CDCl 3): δ =8.20 (s, 1H), 8.10 – 8.15 (m, 1H), 7.83 (s, 1H), 3.96 (s, 3H). 3) | ||
b*-003 | 1 H NMR (400 MHz, d 6-DMSO): δ =14.27 – 14.20 (br s, 1H), 8.51 (s, 1H), 8.49 (s, 1H), 8.38 (s, 1H). | 287.0 # | |
b*-004 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.76 (br s, 1H), 8.03 (s, 1H), 7.98 – 7.95 (m, 1H), 7.93 – 7.89 (m, 1H). | 239.1 # | |
c*-001 | 1 H NMR (400 MHz, Varian machine, MeOD): δ = 7.89 (s, 1H), 7.88 (s, 1H), 7.54 (s, 1 H), 1.78 - 1.82 (m, 2 H), 1.55 - 1.59 (m, 2 H). | 220.1 # | |
d*-001 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.92 (br s, 1H), 8.27 (t, J=1.6 Hz, 1H), 8.25 – 8.20 (m, 2H), 3.13 – 3.05 (m, 1H), 1.25 – 1.05 (m, 4 H). | 259.1 # | |
d*-002 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.90 (br s, 1H), 8.27 (t, J=1.4 Hz, 1H), 8.23 (t, J=1.0 Hz, 1H), 8.21 (t, J=1.8 Hz, 1H), 3.46 (q, J=7.2 Hz 2H), 1.12 (t, J=7.2 Hz 3H). | 247.1 # | |
d*-003 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.94 (br s, 1H), 8.34 (t, J=1.4 Hz, 1H), 8.32 – 8.30 (m, 1H), 8.22 – 8.14 (m, 3H), 7.53 – 7.45 (m, 2H). | 313.0 # | |
d*-004 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.55 (br s, 1H), 7.97 – 7.92 (m, 2H), 7.79 (t, J=1.8 Hz, 1H), 1.27 (s, 9H). | 243.1 # | |
d*-005 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.50 (br s, 1H), 7.77 (t, J=1.6 Hz, 1H), 7.72 (t, J=1.8 Hz, 1H), 7.67 (t, J=1.8 Hz, 1H), 3.67 (sep, J=6.8 Hz 1H), 1.27 (d, J=6.8 Hz 6H). | 229.1 # | |
d*-006 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.55 (br s, 1H), 7.94 – 7.88 (m, 2H), 7.77 (t, J=1.6 Hz, 1H), 4.20 (q, J=10.3 Hz 2H). | 269.0 # | |
e*-001 | 1 H NMR (400 MHz, d 6-DMSO): δ = 13.37 (br s, 1H), 7.65 (t, J=1.6 Hz, 1H), 7.58 – 7.54 (m, 1H), 7.34 (br s, 1H), 2.14 – 2.05 (m, 1H), 1.10 – 1.00 (m, 2H), 0.85 – 0.75 (m, 2 H). | 245.1 # |
將9 mg化合物溶解在1 ml丙酮中並以丙酮稀釋至所欲濃度。將250 μl試驗溶液填充至25 ml玻璃試管中且藉由在搖動裝置上轉動及傾斜而均勻分布在內壁上(以30 rpm經2 h)。以900 ppm之化合物濃度、44,7 cm
2之內表面及均勻的分布,達成5µg/cm²之劑量。
在溶劑蒸發之後,將各試管裝滿5-10隻貓蚤(
貓櫛頭蚤)成蟲,以穿孔蓋封閉且在室溫及相對濕度下以水平位置培育。在48小時後測定效力。將貓蚤敲擊至該管底部且在45-50℃之加熱板上培育最多5分鐘。不能夠向上爬以躲避熱之不動或以不協調方式移動的貓蚤標記為死亡或瀕死。
若以5 µg/cm²之化合物濃度監測到至少80%之效力,則化合物顯示對抗
貓櫛頭蚤的良好效力。100%之效力意指所有的跳蚤死亡或瀕死;0%之效能意指沒有跳蚤死亡或瀕死。
此試驗中,例如,下列來自製備例之化合物於5 µg/cm² (= 500 g/ha)的施用率下顯示100%之良好效力:I-002、I-003、I-007、I-019、I-020、I-021、I-024、I-025、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-042、I-044、I-045、I-046、I-050、I-057、I-066、I-069、I-070、I-089、I-091、I-095。
在此試驗中,例如,下列來自製備例之化合物在5 µg/cm² (= 500g/ha)的施用率下顯示90%之良好活性:I-005、I-006、I-041、I-043、I-067、I-068、I-073、I-074、I-075、I-098。
在此試驗中,例如,下列來自製備例之化合物在5 µg/cm² (= 500g/ha)的施用率下顯示80%之良好活性:I-001、I-051、I-054、I-059、I-092。
血色扇頭壁蝨 (Rhipicephalus sanguineus) – 使用 棕狗蜱成蟲之體外接觸試驗
將9 mg化合物溶解在1 ml丙酮中並以丙酮稀釋至所欲濃度。將250 μl試驗溶液填充至25 ml玻璃試管中且藉由在搖動裝置上轉動及傾斜而均勻分布在內壁上(以30 rpm經2 h)。以900 ppm之化合物濃度、44,7 cm
2之內表面及均勻的分布,達成5µg/cm²之劑量。
在溶劑蒸發之後,將各試管裝滿5-10隻棕狗蜱(
血色扇頭壁蝨)成蟲,以穿孔蓋封閉且在室溫及相對濕度下以水平位置培育。在48小時後測定效力。將狗蜱敲擊至該管底部且在45-50℃之加熱板上培育最多5分鐘。不能夠向上爬以躲避熱之不動或以不協調方式移動的狗蜱標記為死亡或瀕死。
若以5 µg/cm²之化合物濃度監測到至少80%之效力,則化合物顯示對抗
血色扇頭壁蝨的良好效力。100%之效力意指所有的蜱死亡或瀕死;0%之效能意指沒有蜱死亡或瀕死。
在此試驗中,例如,下列來自製備例之化合物在5 µg/cm² (= 500g/ha)的施用率下顯示100%之良好活性:I-001、I-003、I-040、I-045、I-053。
在此試驗中,例如,下列來自製備例之化合物在5 µg/cm² (= 500g/ha)的施用率下顯示80%之良好活性:I-002、I-004、I-006、I-021、I-034、I-036、I-037、I-042、I-066。
微小扇頭蜱 (Boophilus microplus) - 注射試驗溶劑: 二甲基亞碸
為了製造活性化合物的適當製劑,將10 mg的活性化合物溶解在0.5 ml的溶劑中且將濃縮物以溶劑稀釋至所欲濃度。
將1 µl的化合物溶液注入5隻飽血之雌蜱(
微小扇頭蜱)成蟲的腹部。將蜱轉移至複製盤中且在氣候室內培育。
在7天之後監測受精卵的產卵。將看不出受精的卵儲存在氣候室內,直到約42天後孵化為止。100%之效力意指所有的卵都是無精的;0 %意指所有的卵都是受精的。
在此試驗中,例如,下列來自製備例之化合物在20 µg/動物的施用率下顯示100%之良好活性:I-001、I-002、I-003、I-006、I-019、I-020、I-024、I-025、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-048、I-049、I-050、I-051、I-052、I-068、I-069、I-070、I-072、I-073、I-074、I-075、I-076、I-077。
在此試驗中,例如,下列來自製備例之化合物在20 µg/動物的施用率下顯示80%之良好活性:I-021、I-067、I-080。
微小扇頭蜱 (Boophilus microplus) - 浸漬試驗試驗動物: 牛蜱(微小扇頭蜱)Parkhurst品系,SP-抗藥性
溶劑: 二甲亞碸
為了製造活性化合物的適當製劑,將10 mg的活性化合物溶解在0.5 ml的溶劑中,且將濃縮物以水稀釋至所欲濃度。
將此化合物溶液吸移至試管內。將8-10隻飽血的雌牛蜱(
微小扇頭蜱)成蟲轉移至有孔的試管內。將試管浸漬在化合物溶液中直到牛蜱完全濕掉。當液體流掉後,將蜱轉移至塑膠盤中的濾紙上並儲存在氣候室內。
在7天之後監測受精卵的產卵。將看不出受精的卵儲存在氣候室內,直到約42天後孵化為止。100%之效力意指所有的卵都是無精的;0 %意指所有的卵都是受精的。
在此試驗中,例如,下列來自製備例之化合物在100 ppm的施用率下顯示100 %之良好活性:I-020、I-034、I-035、I-037、I-038、I-042、I-044、I-046。
在此試驗中,例如,下列來自製備例之化合物在100 ppm的施用率下顯示90%之良好活性:I-036、I-050。
貓櫛頭蚤 (Ctenocephalides felis) - 口服試驗溶劑: 二甲亞碸
為了製造活性化合物的適當製劑,將10 mg的活性化合物溶解在0.5 ml的溶劑中,且將濃縮物以牛血稀釋至所欲濃度。
將約20隻未餵食的貓蚤(
貓櫛頭蚤)成蟲放入跳蚤室中。將底端用封口膜(parafilm)封閉的血室充滿供有化合物溶液的牛血且放在跳蚤室之紗布覆蓋的頂部,以使貓蚤能夠吸食該血。將血室加熱至37℃,而將貓蚤室保持在室溫下。
2天後,測定以%計的死亡率。100%意指所有的貓蚤已被殺死;0%意指沒有任何貓蚤被殺死。
在此試驗中,例如,下列來自製備例之化合物在100 ppm的施用率下顯示100%之良好活性:I-001、I-002、I-003、I-004、I-006、I-007、I-009、I-010、I-012、I-019、I-020、I-021、I-024、I-025、I-028、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-048、I-049、I-050、I-051、I-052、I-053、I-054、I-057、I-058、I-059、I-060、I-066、I-067、I-068、I-069、I-070、I-071、I-072、I-073、I-074、I-075、I-076、I-080、I-081、I-088、I-089、I-090、I-091。
在此試驗中,例如,下列來自製備例之化合物在100 ppm的施用率下顯示90%之良好活性:I-056、I-077。
黃瓜條葉甲 (Diabrotica balteata) – 噴灑試驗溶劑: 78.0 重量份丙酮
1.5 重量份的二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合,且將濃縮物以含有1000 ppm的乳化劑濃度的水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將浸泡過的小麥種子(小麥(
Triticum aestivum))放在裝有瓊脂和一些水的多孔板中且培育1天以發芽(每孔5顆種子)。以含有所欲濃度的活性成分之試驗溶液噴灑發芽的小麥種子。之後,各單元以10-20隻帶斑黄瓜葉甲(banded cucumber beetle)(
黃瓜條葉甲)的幼蟲感染。
在7天之後測定以%計的效力。100%意指所有苗都如未處理之未感染對照組生長;0%意指沒有苗生長。
在此試驗中,例如,下列來自製備例之化合物在160 µg/孔的施用率下顯示100%之良好活性:I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-011、I-012、I-014、I-016、I-019、I-020、I-024、I-025、I-026、I-028、I-033、I-034、I-035、I-036、I-037、I-039、I-040、I-041、I-042、I-043、I-044、I-045、I-048、I-049、I-051、I-053、I-054、I-060、I-063、I-064、I-066、I-067,I-068、I-069、I-070、I-072、I-073、I-074、I-075、I-077、I-078、I-079、I-089、I-090、I-091、I-092、I-093、I-094、I-095、I-097、I-098、I-099、I-100、I-104、I-107、I-113、I-114、I-115、I-117、I-118、I-119、I-120、I-121、I-123、I-124、I-125。
在此試驗中,例如,下列來自製備例之化合物在160 µg/孔的施用率下顯示80%之良好活性:I-050、I-057。
桃蚜 (Myzus persicae) – 口服試驗溶劑: 100 重量份丙酮
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合,且將濃縮物以水稀釋至所欲濃度。
將50 µl化合物溶液裝入微量滴定板中並添加150 µl IPL41昆蟲培養基(33% + 15%糖),以獲得每孔200 µl之總體積。之後將該等板用封口膜(parafilm)密封,綠桃蚜(
桃蚜)的混合群可通過該封口膜吮吸化合物製劑。
在5天之後測定以%計的死亡率。100%意指所有的蚜蟲已被殺死及0%意指沒有蚜蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物在20 ppm的施用率下顯示100%之良好活性:I-001、I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-012、I-019、I-020、I-024、I-025。
在此試驗中,例如,下列來自製備例之化合物在4 ppm的施用率下顯示100%之良好活性:I-007、I-008、I-009、I-019、I-020、I-024、I-033、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-043、I-044、I-046、I-048、I-050、I-051、I-057、I-063、I-067、I-069、I-070、I-074、I-075、I-080、I-090、I-091、I-092、I-095、I-096、I-097、I-099、I-117、I-119。
在此試驗中,例如,下列來自製備例之化合物在4 ppm的施用率下顯示90%之良好活性:I-003、I-005、I-006、I-066、I-068、I-086、I-093、I-118。
桃蚜 (Myzus persicae) – 噴灑試驗溶劑: 78.0 重量份丙酮
1.5 重量份二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合,且將濃縮物以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將受到所有齡的綠桃蚜(桃蚜(
Myzus persicae))感染之大白菜(Chinese cabbage)(山東白菜(
Brassica pekinensis))葉圓盤以所欲濃度之活性成分的製劑噴灑。
在5天之後測定以%計的死亡率。100%意指所有的蚜蟲已被殺死及0%意指沒有蚜蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示100%之良好活性:I-036、I-039、I-041、I-044、I-045、I-046、I-050、I-070、I-092、I-099、I-121、I-124、I-125。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示90%之良好活性:I-034、I-035、I-037、I-040、I-042、I-043、I-057、I-066、I-073、I-074、I-075、I-091、I-095、I-096、I-100、I-114、I-118、I-119。
稻綠蝽 (Nezara viridula) – 噴灑試驗溶劑: 78.0 重量份的丙酮
1.5 重量份的二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合,且將濃縮物以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將以南方綠椿象(southern green stink bug)(
稻綠蝽)感染的大麥植物(大麥(
Hordeum vulgare))以含有所欲濃度之活性成分的試驗溶液噴灑。
在4天後,測定以%計的死亡率。100%意指所有的椿象已被殺死;0%意指沒有椿象被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示100%之良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I-008、I-016、I-019、I-020、I-025、I-033、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-049、I-050、I-051、I-057、I-060、I-063、I-066、I-067、I-068、I-069、I-070、I-073、I-074、I-075、I-078、I-080、I-089、I-090、I-091、I-092、I-093、I-095、I-096、I-097、I-098、I-099、I-100、I-104、I-107、I-110、I-117、I-118、I-119、I-120、I-121、I-124、I-125。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示90%之良好活性:I-109、I-113。
褐飛蝨 (Nilaparvata lugens) – 噴灑試驗溶劑: 78.0 重量份的丙酮
1.5 重量份的二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合,且將濃縮物以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將稻米植物(稻(
Oryza sativa))以所欲濃度之活性成分的製劑噴灑且以褐飛蝨(brown planthopper)(褐飛蝨(
Nilaparvata lugens))之幼蟲感染植物。
在4天後測定以%計之死亡率。100%意指所有的稻飛蝨已被殺死及0%意指沒有飛蝨被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示100%之良好活性:I-001、I-003、I-004、I-005、I-006、I-008、I-018、I-019、I-020、I-024、I-025、I-033、I-034、I-037、I-039、I-040、I-041、I-042、I-043、I-044、I-049、I-050、I-059、I-092、I-100、I-111、I-118、I-120。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示90%之良好活性:I-045、I-046。
辣根猿葉甲 (Phaedon cochleariae) - 噴灑試驗溶劑: 78.0 重量份的丙酮
1.5 重量份的二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合並以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將大白菜(
山東白菜)葉圓盤以所欲濃度之活性成分的製劑噴灑。一旦乾燥,以芥菜甲蟲幼蟲(
辣根猿葉甲)感染該等葉圓盤。
7天之後,測定以%計之死亡率。100%意指所有的甲蟲幼蟲已被殺死及0%意指沒有甲蟲幼蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示100%之良好活性:I-001、I-003、I-004、I-005、I-006、I-008、I-009、I-010、I-012、I-016、I-019、I-020、I-024、I-026、I-028。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示83%之良好活性:I-025。
草地夜蛾 ( Spodoptera frugiperda) – 噴灑試驗溶劑: 78.0 重量份丙酮
1.5 重量份的二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合並以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將玉米(玉蜀黍(
Zea mays))之葉段以所欲濃度之活性成分的製劑噴灑。一旦乾燥,以秋夜盜蛾(
草地夜蛾)之幼蟲感染該等葉段。
7天之後,測定以%計之死亡率。100%意指所有的毛蟲已被殺死及0%意指沒有毛蟲被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示100%之良好活性:I-005、I-008、I-009、I-012、I-019、I-033、I-035、I-036、I-038、I-040、I-043、I-045、I-046、I-050、I-051、I-053、I-054、I-057、I-063、I-064、I-066、I-067、I-068、I-069、I-070、I-072、I-073、I-074、I-075、I-077、I-078、I-079、I-089、I-090、I-095、I-096、I-097、I-099、I-100、I-104、I-106、I-110、I-113、I-117、I-118、I-119、I-120、I-121、I-123、I-125。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示83%之良好活性:I-004、I-034、I-037、I-042、I-044、I-091、I-094、I-098。
二點葉蟎 (Tetranychus urticae)- 噴灑試驗 OP- 抗性溶劑: 78.0 重量份丙酮
1.5 重量份二甲基甲醯胺
乳化劑: 烷基芳基聚乙二醇醚
為了製造活性化合物的適當製劑,將1重量份活性化合物與所述量的溶劑混合並以含有1000 ppm的乳化劑濃度之水稀釋至所欲濃度。藉由以含有乳化劑的水稀釋製備其他試驗濃度。
將受到所有齡的二點葉蟎(
二點葉蟎)感染的四季豆(菜豆(
Phaseolus vulgaris))葉圓盤以所欲濃度之活性成分的製劑噴灑。
在6天後,測定以%計之死亡率。100%意指所有的蜘蛛蟎已被殺死及0%意指沒有蜘蛛蟎被殺死。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示95%之良好活性:I-006、I-008。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示90%之良好活性:I-040、I-042、I-056、I-112。
在此試驗中,例如,下列來自製備例之化合物在500 g/ha的施用率下顯示80%之良好活性:I-005。
埃及斑蚊 (Aedes aegypti)試驗(AEDSAE表面處理&接觸分析)
溶劑:丙酮+2000 ppm油菜籽油甲酯(RME)
為了製造含有足夠活性成分的溶液,必須將試驗化合物溶解在溶劑混合物(於 2 mg/mL之丙酮/ RME 2000 ppm)中。將此溶液移液到釉面磚上且在丙酮蒸發後,將埃及斑蚊種品系 MONHEIM的成蚊放在乾燥的表面上。曝露時間為30分鐘。
與處理過之表面接觸24小時後,測定以百分比(%)計之死亡率。100%死亡率意指所有的試驗昆蟲死亡,而0%意指沒有一隻昆蟲死亡。
在此試驗中下列化合物-實施例-編號在20 mg/m
2之表面濃度下顯示90-100%之效力:I-001、I-019、I-024、I-025、I-034、I-035、I-036、I-037、I-038、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-048、I-049、I-050、I-053、I-054、I-057、I-063、I-066、I-067、I-068、I-069、I-070、I-073、I-074、I-075、I-077、I-078、I-089、I-091、I-092、I-093、I-098、I-100、I-104。
在此試驗中下列化合物-實施例-編號在4 mg/m
2之表面濃度下顯示80-100%之效力:I-001、I-019、I-034、I-035、I-036、I-037、I-038、I-040、I-041、I-042、I-043、I-044、I-045、I-049、I-050、I-053、I-054、I-057、I-063、I-066、I-067、I-068、I-069、I-070、I-073、I-075、I-078、I-089、I-091、I-092、I-093、I-100、I-104。
熱帶家蚊 (Culex quinquefasciatus))試驗(CULXFA表面處理&接觸分析)
溶劑:丙酮+2000 ppm油菜籽油甲酯(RME)
為了製造含有足夠活性成分的溶液,必須將試驗化合物溶解在溶劑混合物(於 2 mg/mL之丙酮/ RME 2000 ppm)中。將此溶液移液到釉面磚上且在丙酮蒸發後,將熱帶家蚊種品系P00的成蚊放在乾燥的表面上。曝露時間為30分鐘。
與處理過之表面接觸24小時後,測定以百分比(%)計之死亡率。100%死亡率意指所有的試驗昆蟲死亡,而0%意指沒有一隻昆蟲死亡。
在此試驗中下列化合物-實施例-編號在20 mg/m
2之表面濃度下顯示80-100%之效力:I-001、I-019、I-025、I-034、I-035、I-036、I-037、I-038、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-049、I-050、I-057、I-063、I-066、I-067、I-068、I-069、I-070、I-073、I-074、I-075、I-078、I-089、I-091、I-092、I-093、I-098、I-100、I-104、I-107。
在此試驗中下列化合物-實施例-編號在4 mg/m
2之表面濃度下顯示80-100%之效力:I-019、I-034、I-035、I-036、I-037、I-038、I-040、I-041、I-042、I-043、I-044、I-045、I-050、I-063、I-066、I-067、I-068、I-069、I-070、I-073、I-075、I-078、I-089、I-091、I-092、I-093、I-100、I-104。
不吉瘧蚊 (Anopheles funestus)試驗(ANPHFU表面處理&接觸分析)
溶劑:丙酮+2000ppm油菜籽油甲酯(RME)
為了製造含有足夠活性成分的溶液,必須將試驗化合物溶解在溶劑混合物(於 2 mg/mL之丙酮/ RME 2000 ppm)中。將此溶液移液到釉面磚上且在丙酮蒸發後,將不吉瘧蚊種品系FUMOZ-R(Hunt等人,Med Vet Entomol.2005 Sep;19(3):271-5)的成蚊放在乾燥的表面上。曝露時間為30分鐘。
與處理過之表面接觸24小時後,測定以百分比(%)計之死亡率。100%死亡率意指所有的試驗昆蟲死亡,而0%意指沒有一隻昆蟲死亡。
在此試驗中下列化合物-實施例-編號在20 mg/m
2之表面濃度下顯示85-100%之效力:I-001、I-024、I-025、I-041、I-042、I-045、I-049、I-066、I-068、I-070、I-073、I-078、I-091、I-100。
在此試驗中下列化合物-實施例-編號在4 mg/m
2之表面濃度下顯示85-100%之效力:I-001、I-024、I-025、I-034、I-041、I-045、I-049、I-066、I-068、I-070、I-092、I-093、I-100。
家蠅 (Musca domestica)試驗(MUSCDO表面處理&接觸分析)
溶劑:丙酮+2000 ppm油菜籽油甲酯(RME)
為了製造含有足夠活性成分的溶液,必須將試驗化合物溶解在溶劑混合物(於 2 mg/mL之丙酮/ RME 2000 ppm)中。將此溶液移液到釉面磚上且在丙酮蒸發後,將家蠅種品系WHO-N的成蠅放在乾燥的表面上。曝露時間為30分鐘。
與處理過之表面接觸24小時後,測定以百分比(%)計之死亡率。100%死亡率意指所有的試驗昆蟲死亡,而0%意指沒有一隻昆蟲死亡。
在此試驗中下列化合物-實施例-編號在20 mg/m
2之表面濃度下顯示80-100%之效力:I-019、I-025、I-035、I-040、I-042、I-043、I-045、I-050、I-053、I-054、I-066、I-067、I-068、I-069、I-070、I-073、I-074、I-075、I-078、I-100、I-104。
在此試驗中下列化合物-實施例-編號在4 mg/m
2之表面濃度下顯示80-100%之效力:I-019、I-035、I-042、I-045、I-050、I-053、I-054、I-068、I-069、I-100、I-104。
德國蜚蠊 (Blattella germanica)試驗(BLTTGE表面處理&接觸分析)
溶劑:丙酮+2000 ppm油菜籽油甲酯(RME)
為了製造含有足夠活性成分的溶液,必須將試驗化合物溶解在溶劑混合物(於 2 mg/mL之丙酮/ RME 2000 ppm)中。將此溶液移液到釉面磚上且在丙酮蒸發後,將德國蜚蠊種品系PAULINIA的成年動物放在乾燥的表面上。曝露時間為30分鐘。
與處理過之表面接觸24小時後,測定以百分比(%)計之死亡率。100%死亡率意指所有的試驗昆蟲死亡,而0%意指沒有一隻昆蟲死亡。
在此試驗中下列化合物-實施例-編號在20 mg/m
2之表面濃度下顯示80-100%之效力:I-035、I-036、I-037。
Claims (8)
- 如請求項2之化合物,其中A為氯。
- 如請求項4之化合物,其中A為氯。
- 如請求項4之化合物,其中L為S或SO2。
- 如請求項4之化合物,其中L為SO2。
- 一種化合物,其係選自3-環丙基-5-(三氟甲氧基)苯甲酸和3-環丙基-5-(三氟甲氧基)苯甲酸甲酯。
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