CN1280277C - 含非芳族杂环的肼无脊椎害虫防治剂 - Google Patents
含非芳族杂环的肼无脊椎害虫防治剂 Download PDFInfo
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- CN1280277C CN1280277C CNB028102592A CN02810259A CN1280277C CN 1280277 C CN1280277 C CN 1280277C CN B028102592 A CNB028102592 A CN B028102592A CN 02810259 A CN02810259 A CN 02810259A CN 1280277 C CN1280277 C CN 1280277C
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- Prior art keywords
- alkyl
- carbonyl
- formula
- compound
- phenyl
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 title description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 238000000034 method Methods 0.000 claims abstract description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 239000007787 solid Substances 0.000 claims abstract description 9
- 239000003085 diluting agent Substances 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 871
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 854
- 229910052799 carbon Inorganic materials 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 61
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 230000000975 bioactive effect Effects 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 22
- 150000003839 salts Chemical class 0.000 abstract description 22
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 abstract description 10
- 150000001204 N-oxides Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 5244
- -1 heterocycle hydrazine class compounds Chemical class 0.000 description 99
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 29
- 239000002253 acid Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 29
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 28
- 150000001721 carbon Chemical group 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- 125000003368 amide group Chemical group 0.000 description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- 239000003513 alkali Substances 0.000 description 18
- 125000000304 alkynyl group Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000004414 alkyl thio group Chemical group 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
- 239000002516 radical scavenger Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 238000006352 cycloaddition reaction Methods 0.000 description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 7
- 238000006073 displacement reaction Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 150000003217 pyrazoles Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000005864 Sulphur Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 150000001263 acyl chlorides Chemical class 0.000 description 6
- 235000008504 concentrate Nutrition 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 150000003851 azoles Chemical class 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 230000002902 bimodal effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000003880 polar aprotic solvent Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000005815 base catalysis Methods 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
- 125000000232 haloalkynyl group Chemical group 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000002769 thiazolinyl group Chemical group 0.000 description 3
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- 238000012546 transfer Methods 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical class NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 238000013459 approach Methods 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012434 nucleophilic reagent Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- JHGAGJCUHXJCPF-UHFFFAOYSA-N 2-amino-3-methyl-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(C)=C1N JHGAGJCUHXJCPF-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UOHBMRODJBFDPN-UHFFFAOYSA-N C(C)(C)(C)O.[Li] Chemical compound C(C)(C)(C)O.[Li] UOHBMRODJBFDPN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 101100379079 Emericella variicolor andA gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- ZQILHGZZALSESY-UHFFFAOYSA-N [PH5].C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound [PH5].C1(=CC=CC=C1)C1=CC=CC=C1 ZQILHGZZALSESY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- NJXXWBJAOFKNIR-UHFFFAOYSA-N hexa-1,4-diyne Chemical compound CC#CCC#C NJXXWBJAOFKNIR-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
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Abstract
本发明提供式I的化合物、其N-氧化物和农业上适用的盐,其中A和B独立地为O或S;J是任选被取代的5元或6元非芳族杂环;K与两个相邻键接的碳原子一起形成苯环或5元或6元杂芳环,各环任选被取代;和R1、R2和R3如公开文件所定义。还公开了防治无脊椎害虫的方法,包括用生物有效量的式I化合物、其N-氧化物或该化合物适当的盐(例如以本文所述的组合物形式)接触无脊椎动物或其环境。本发明还涉及一种防治无脊椎害虫的组合物,该组合物含生物有效量的式I化合物、其N-氧化物或该化合物适当的盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加成分。
Description
发明背景
本发明涉及一些杂环肼类化合物、其N-氧化物、适当的盐和组合物,及其用于防治农业和非农业环境中的无脊椎害虫的方法。
无脊椎害虫的防治对于实现高农作物产率是极为重要的。无脊椎害虫对农作物生长和储藏造成的损失会造成生产力的显著降低,由此导致消费者成本增加。林业、温室作物、观赏植物、苗圃作物、贮藏品和纤维产品、家畜、家庭,和公众卫生与动物健康领域内的无脊椎害虫防治也是非常重要的。市场上可买到适用上述目的的许多产品,但仍需要更有效的、较低成本的、较低毒性的、环境较安全的或具有不同的作用模式的新化合物。
NL9202078公开了式i的N-酰基邻氨基苯甲酸衍生物作为杀虫剂
其中,特别是,X是直接的键(direct bond);Y是H或C1-C6烷基;Z是NH2,NH(C1-C3烷基)或N(C1-C3烷基)2;和R1至R9彼此独立地是H、卤素、C1-C6-烷基、苯基、羟基、C1-C6烷氧基或C1-C7酰氧基。
WO01/070671公开了式ii的N-酰基邻氨基苯甲酸衍生物作为杀节肢动物剂
其中特别是,A和B彼此独立地是O或S;J是任选被取代的苯环、5元或6元杂芳环、萘环系统或芳族8、9或10元稠合杂双环系统;R1和R3彼此独立地是H或任选被取代的C1-C6烷基;R2是H或C1-C6烷基;每个R4独立地是H、C1-C6烷基、C1-C6卤代烷基、卤素或CN;和n是1-4。
发明概述
本发明涉及式I的化合物及其N-氧化物或其农业上适用的盐
其中
A和B独立地是O或S;
J是任选被取代的5元或6元非芳族杂环;
K与两个相邻键接的碳原子一起形成苯环或5-或6-元杂芳环,每个环任选被取代;
R1是H;C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团均任选被取代;C2-C6烷基羰基;C2-C6烷氧基羰基;C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
R2是H,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,C1-C4烷氧基,C1-C4烷基氨基,C2-C8二烷基氨基,C3-C6环烷基氨基,C2-C6烷氧基羰基或C2-C6烷基羰基;
R3是H;G;C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,各基团均任选被取代;或
R2和R3与其相连的氮原子一起形成含2-6个碳原子和任选的一个另外的氮、硫或氧原子的环,并且该环可任选被取代;和
G是任选被取代的5-或6-元非芳族碳环或杂环,任选含一个或多个选自C(=O)、SO或S(O)2的环节(ring member)。
本发明还涉及防治无脊椎害虫的方法,包括用生物有效量的式I化合物、其N-氧化物或该化合物适当的盐(例如以本文所述的组合物形式)接触无脊椎害虫或其环境。本发明还涉及这样的方法,该方法将无脊椎害虫或其环境与生物有效量的式I化合物、其N-氧化物或其适当的盐,或含该化合物、其N-氧化物或其适当的盐和生物有效量的至少一种另外的化合物或试剂的、用于防治无脊椎害虫的组合物接触。
本发明还涉及一种防治无脊椎害虫的组合物,该组合物含生物有效量的式I化合物、其N-氧化物或该化合物适当的盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加成分。本发明还涉及一种组合物,该组合物含生物有效量的式I化合物、其N-氧化物或该化合物适当的盐和有效量的至少一种另外的生物活性化合物或试剂。
发明详述
如上所述,J是任选被取代的5-或6-元非芳族杂环。关于这些J基团的术语“任选被取代的”指未被取代或有至少一个不消除生物活性的非氢取代基的J基团。任选被取代的J基团(其中所述环任选被一至7个R5取代)的实例包括展示(Exhibit)1所示例的环,其中m是1-7的整数,R5如下所述。如同环中的碳原子一样,需要取代以配其化合价的氮原子被氢或R5取代。虽然(R5)m基团示于J-1至J-35结构中,但应注意到由于R5是任选的取代基,因此其不必需存在。还应注意到当R5取代基是H时,相当于R5取代基相连的原子是未被取代的。应注意当J基团上的连接点解释为不固定的时,J基团可通过置换氢原子经由J基团的任何可用的碳原子或氮原子连接到式I的剩余部分。应注意J-3和J-4是J-19的子集,其中连接到式I其余部分的点是固定的。应注意在J-5中,X是O或S,且当X是O时,J-5是J-29的子集,其中连接到式I其余部分的点是固定的,且当X是S时,J-5是J-30的子集,其中连接到式I其余部分的点是固定的。J-17和J-22的优选连接点是在_唑啉J-17和噻唑啉J-22的标为4或5的位置上。
展开1
当连接到J时,任选的R5取代基的实例包括那些,其中每个R5独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN,CO2H,CONH2,NO2,羟基,C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基、C3-C6三烷基甲硅烷基或W;
(R5)2当与相邻的碳原子连接时,与所述碳原子合为-OCF2O-、-CF2CF2O-或-OCF2CF2O-;和
每个W独立地是苯基、苯甲基、苯甲酰基、苯氧基、5-或6-元杂芳环、萘环体系或芳族8-、9-或10-元稠合杂双环体系,各环或环体系任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基或C3-C6三烷基甲硅烷基。
如上所述,K与两个相邻键接的碳原子一起形成苯环或5元或6元杂芳环,各环任选被取代。关于这些K基团的术语“任选被取代的”指未被取代或有至少一个不消除生物活性的非氢取代基的K基团。任选被取代的苯环(K-38)和芳族杂环(K-1至K-37)(其中所述环任选被一至四个R4取代)的实例包括展示2所示例示的环体系,其中n是1-4的整数,R4如下所述。如同环中的碳原子一样,需要取代以配其化合价的氮原子被氢或R4取代。虽然(R4)n基团示于K-1至K-38结构中,但应注意到由于R4是任选的取代基,因此其不必需存在。应注意一些K基团可仅被小于三个R4基团取代(例如K-7至K-10、K-15、K-16、K-20、K-21、K-23、K-24、K-26和K-27可仅被一个R4取代)。在例举的K基团中,较高的右键通过可用的连接碳原子连接到式I的NR1(=A)J部分的氮原子,较低的右键通过可用的连接碳原子连接到式I的C(=B)NR2R3部分的碳原子上。波状线表示K环连接到下文式Ia所示的式I的剩余部分。
展示2
优选的K环包括任选被取代的噻吩、异_唑、异噻唑、吡唑、吡啶、嘧啶和苯环。更优选的K环包括K-1、K-14、K-15、K-18、K-23、K-28、K-29、K-30、K-31、K-33和K-38。最优选的K环是K-28、K-31、K-33和K-38。
当连接到K时,任选的R4取代基的实例包括那些,其中:
每个R4独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN,NO2,羟基,C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、NH2、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、或C3-C6三烷基甲硅烷基;或
每个R4独立地是苯基、苯甲基或苯氧基,各基团任选被一至三个取代基取代,所述取代基选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基和C3-C6三烷基甲硅烷基。
如上所述,R1(除了别的以外)是C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团任选被取代。关于这些R1基团的术语“任选被取代的”指未被取代或有至少一个不消除生物活性的非氢取代基的R1基团。任选被取代的R1基团的实例包括任选被一个或多个取代基取代的R1基团,所述取代基独立地选自卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基。重要的是任选被一个至五个取代基取代的R1基团,所述取代基独立地选自上述基团。
如上所述,R3(除了别的以外)是C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,各基团任选被取代。关于这些R3基团的术语“任选被取代的”指未被取代或有至少一个不消除生物活性的非氢取代基的R3基团。任选被取代的R3基团的实例包括任选被一个或多个取代基取代的R3基团,所述取代基选自卤素、G、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C6烷氧基羰基、C2-C6烷基羰基、C3-C6三烷基甲硅烷基或苯基、苯氧基或5-元或6-元杂芳环,各环任选被一个至三个取代基取代,所述取代基独立地选自R6;C1-C4烷基氨基;C2-C8二烷基氨基;C3-C6环烷基氨基;C2-C6烷氧基羰基或C2-C6烷基羰基。重要的是任选被一个至五个取代基取代的R3基团,所述取代基独立地选自上述基团。
如上所述,R2和R3与其相连的氮原子一起形成含2-6个碳原子和任选的一个另外的氮、硫或氧原子的环,并且该环可任选被取代。关于所述环的术语“任选被取代的”指未被取代或有至少一个不消除生物活性的非氢取代基的环。所述任选被取代的环的实例包括任选被1-4个取代基取代的环,所述取代基独立地选自R7,其中每个R7独立地是C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基。
如上所述,G是5-或6-元非芳族碳环或杂环,任选含一个或两个选自C(=O)、SO或S(O)2的环节,且任选被1-4个取代基取代,所述取代基选自C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基。关于这些G基团的术语“任选被取代的”指未被取代或有至少一个不会消除未取代的类似物具有的杀节肢动物活性的非氢取代基的G基团。应注意当G基团上的连接点解释为不固定的时,G基团可通过置换氢原子经由G基团的任何可用的碳原子连接到式I的剩余部分。任选的取代基可通过置换氢原子连接到任何可用的碳原子上。作为G的5-或6-元非芳族碳环的实例包括示为展示3的G-1至G-8的环,其中所述环可任选被1-4个取代基取代,所述取代基选自C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基。作为G的5-或6-元非芳族杂环的实例包括示为展示3的G-9至G-38的环,其中所述环可任选被1-4个取代基取代,所述取代基选自C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基。应注意当G包含选自G-31至G-34、G-37和G-38的环时,Q1选自O、S或N。应注意当G是G-11、G-13、G-14、G-16、G-23、G-24、G-30至G-34、G-37和G-38和Q1是N时,该氮原子可通过被H或C1-C2烷基取代以满足其化学价。
展示3
在上述叙述中,“芳族”表示每个环原子基本处于同一平面并且有垂直于环平面的p轨道,其中的(4n+2)π电子在n是0或正整数时与环缔合(associated)服从休克尔规则。术语“芳族环体系”表示完全不饱和的碳环和杂环,其中多环体系的至少一个环是芳族的。芳族碳环或环体系包括全芳族碳环和多环体系中至少一个环是芳族的(例如苯基和萘基)的碳环。术语“非芳族碳环”表示全饱和碳环以及部分或全不饱和碳环,该环不满足休克尔规则。关于环或环体系的术语“杂”指其中至少一个环原子不是碳并且可以含有1-4个杂原子的环或环体系,所述杂原子独立地选自氮、氧和硫,条件是每个环含不多于4个氮原子、不多于2个氧原子和不多于2个硫原子。术语“杂芳环或环体系”和“芳族稠合杂双环体系”包括全芳族杂环和多环体系中至少一个环是芳环的杂环(这里的芳环表明满足休克尔规则)。术语“非芳族杂环或环体系”表示全饱和的杂环以及部分或全不饱和的杂环,环体系中的任何环均不满足休克尔规则。杂环或环体系可通过置换任何可用的碳或氮上的氢经由所述碳或氮连接。
术语“烷基”在单独或复合词如“烷硫基”或“卤代烷基”中使用时均包括直链或支链烷基,如甲基、乙基、正丙基、异丙基、或不同的丁基、戊基或己基异构体。“烯基”包括直链或支链链烯如1-丙烯基、2-丙烯基、和不同的丁烯基、戊烯基和己烯基异构体。“烯基”还包括多烯如1,2-丙二烯和2,4-己二烯。“炔基”包括直链或支链炔基如1-丙炔基、2-丙炔基和不同的丁炔基、戊炔基和己炔基异构体。“炔基”还包括由多个三键构成的部分如2,5-己二炔基。“烷氧基”包括例如甲氧基、乙氧基、正丙氧基、异丙氧基和不同的丁氧基、戊氧基和己氧基异构体。“烷硫基”包括支链或直链烷硫基部分如甲硫基、乙硫基,和不同的丙硫基和丁硫基异构体。“环烷基”包括例如环丙基、环丁基、环戊基和环己基。
术语“卤素”在单独或复合词如“卤代烷基”中使用时均包括氟、氯、溴或碘。此外,当用于复合词如“卤代烷基”时,所述烷基可以是部分或全部被相同或不同的卤素原子取代。“卤代烷基”的实例包括F3C、ClCH2、CF3CH2和CF3CCl2。术语“卤代烯基”、“卤代炔基”、“卤代烷氧基”等与术语“卤代烷基”类似地定义。“卤代烯基”的实例包括(Cl)2C=CHCH2和CF3CH2CH=CHCH2。“卤代炔基”的实例包括HC≡CCHCl、CF3C≡C、CCl3C≡C和FCH2C≡CCH2。“卤代烷氧基”的实例包括CF3O、CCl3CH2O、HCF2CH2CH2O和CF3CH2O。
“烷基羰基”的实例包括C(O)CH3、C(O)CH2CH2CH3和C(O)CH(CH3)2。“烷氧基羰基”的实例包括CH3OC(=O)、CH3CH2OC(=O)、CH3CH2CH2OC(=O)、(CH3)2CHOC(=O)和不同的丁氧基-或戊氧基羰基异构体。“烷基氨基羰基”的实例包括CH3NHC(=O)、CH3CH2NHC(=O)、CH3CH2CH2NHC(=O)、(CH3)2CHNHC(=O)和不同的丁基氨基-或戊基氨基羰基异构体。“二烷基氨基羰基”的实例包括(CH3)2NC(=O)、(CH3CH2)2NC(=O)、CH3CH2(CH3)NC(=O)、CH3CH2CH2(CH3)NC(=O)和(CH3)2CHN(CH3)C(=O)。
取代基中碳原子的总数用“Ci-Cj”前缀表示,其中i和j是1-6的数字。例如,C1-C3烷基磺酰基表示甲基磺酰基至丙基磺酰基;C2烷氧基烷基表示CH3OCH2。
在上述叙述中,当式I的化合物含杂环时,所有的取代基均通过置换任何可用的碳原子或氮原子上的氢经由所述碳原子或氮原予连接于此环。
当一个基团含有一个可以为氢的取代基,例如R3,那么当此取代基为氢时,可认为这相当于所述基团未被取代。
当化合物被具有表示所述取代基的数目可以大于1的下标的取代基取代时,则所述取代基(当其多于1时)独立地选自已定义的取代基。此外,当下标表示一个范围,例如(R)i-j,则取代基的数目可以选自介于i和j间的整数,包括i和j。
术语“任选被一至三个取代基取代”等表示该基团上一至三个空位可以被取代。当基团含可以为氢的取代基时,例如R1或R5,则当此取代基为氢时,认为这相当于所述基团未被取代。
本发明的化合物可以存在一个或多个立体异构体。各种立体异构体包括对映异构体、非对映异构体、阻转异构体(atropisomer)和几何异构体。本领域技术人员能意识到当一种立体异构体相对于其他立体异构体富集或与其他立体异构体分离时,该立体异构体可能更有活性和/或可能显示有益效果。此外,技术人员知道如何分离、富集和/或选择性制备所述立体异构体。因此,本发明的化合物可以以立体异构体混合物、单一的立体异构体或光学活性形式存在。
本发明包含选自式I的化合物、其N-氧化物和农业上适用的盐的化合物。本领域技术人员会意识到由于氮需要一个可用的未共享电子对以氧化成氧化物,因此不是所有含氮的杂环都能形成N-氧化物;本领域技术人员能认出能形成N-氧化物那些含氮杂环。本领域技术人员还认可叔胺能形成N-氧化物。制备杂环和叔胺的N-氧化物的制备方法是本领域技术人员熟知的,包括用过氧酸如过乙酸和间-氯过苯甲酸(MCPBA)、过氧化氢、烷基氢过氧化物如叔丁基氢过氧化物、过硼酸钠和双环氧乙烷类如二甲基双环氧乙烷氧化杂环和叔胺。这些N-氧化物制备方法已被详尽地描述并且综述于文献中,见例如:T.L.Gilchristin Comprehensive Organic Synthesis,第7卷,第748-750页,S.V.Ley,Ed.,Pergamon Press;M.Tisler and B.Stanovnik in ComprehensiveHteerocyclic Chemistry,第3卷,第18-19页,A.J.Boulton and A.McKillop,Eds.,Pergamon Press;M.R.Grimmett and B.R.T.Keene inAdvances in Heterocyclic Chemsitry,第43卷,第139-151页,A.R.Katritzky,Ed.,Academic Press;M.Tisler and B.Stanovnik in Advancesin Heterocyclie Chemistry,第9卷,第285-291页,A.R.Katritzky andA.J.Boulton,Eds.,Academic Press;和G.W.H.Cheeseman和E.S.G.Werstiuk in Advances in Heterocyclic Chemistry,第22卷,第390-392页,A.R.Katritzky and A.J.Boulton,Eds.,Academic Press。
本发明化合物的盐包括与无机或有机酸如氢溴酸、氢氯酸、硝酸、磷酸、硫酸、乙酸、丁酸、延胡索酸、乳酸、顺丁烯二酸、丙二酸、草酸、丙酸、水杨酸、酒石酸、4-甲苯磺酸或戊酸形成的酸加成盐。当化合物含酸性基团如羧酸或苯酚时,本发明化合物的盐还包括与有机碱(例如吡啶、氨或三乙基胺)或无机碱(例如钠、钾、锂、钙、镁或钡的氢化物、氢氧化物或碳酸盐)形成的盐。
因为成本、合成的容易性和/或生物效力的原因,优选的化合物是:
优选1:示例为式Ia的式I化合物:
其中
A和B独立地是O或S;
J是
K与两个键合原子一起形成苯环或5-或6-元杂芳环,各环任选被1-4个R4取代;
X是O或S;
R1是H;或C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团任选被一个或多个取代基取代,所述取代基独立地选自卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
R1是C2-C6烷基羰基,C2-C6烷氧基羰基,C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
R2是H,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,C1-C4烷氧基、C1-C4烷基氨基,C2-C8二烷基氨基,C3-C6环烷基氨基,C2-C6烷氧基羰基或C2-C6烷基羰基;
R3是H;G;C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,各基团均任选被一个或多个取代基取代,所述取代基独立地选自卤素、G、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C6烷氧基羰基、C2-C6烷基羰基、C3-C6三烷基甲硅烷基,或苯基、苯氧基或5-或6-元杂芳环,各环任选被一至三个取代基取代,所述取代基选自R6;C1-C4烷基氨基;C2-C8二烷基氨基;C3-C6环烷基氨基;C2-C6烷氧基羰基或C2-C6烷基羰基;或
R2和R3与其相连的氮原子一起形成含2-6个碳原子和任选的一个另外的氮、硫或氧原子的环,该环可任选被1-4个选自R7的取代基取代;
G是5-或6-元非芳族碳环或杂环,任选含一个或两个选自C(=O)、SO或S(O)2的环节并且任选被1-4个选自R7的取代基取代;
每个R4独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、NH2、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、或C3-C6三烷基甲硅烷基;或
每个R4独立地是苯基、苯甲基或苯氧基,各基团任选被一至三个选自R6的取代基取代;
每个R5独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN、CO2H、CONH2、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基、C3-C6三烷基甲硅烷基或W;
(R5)2当与相邻的碳原子连接时,与所述碳原子合为-OCF2O-、-CF2CF2O-或-OCF2CF2O-;
每个W独立地是苯基、苯甲基、苯甲酰基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环体系,各环任选被一至三个选自R6的取代基取代;
每个R6独立地是C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基或C3-C6三烷基甲硅烷基;
每个R7独立地是C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基;
m是1-7的整数;和
n是1-3的整数。
优选2.优选1中的化合物,其中K与两个键接原子一起形成任选被1-3个R4取代的苯环。
优选3.优选1中化合物,其中K与两个键接原子一起形成任选被1-3个R4取代的噻吩、吡唑、异_唑、吡啶或嘧啶。
优选4.优选的2或优选3中化合物,其中
A和B都是O;
n是1或2;
R1是H,C1-C4烷基,C2-C4烯基,C2-C4炔基、C3-C6环烷基,C2-C6烷基羰基或C2-C6烷氧基羰基;
R2是H,C1-C4烷基,C2-C4烯基,C2-C4炔基,C3-C6环烷基,C2-C6烷基羰基或C2-C6烷氧基羰基;
R3是H;或C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团均任选被一个或多个取代基取代,所述取代基选自卤素、CN、C1-C2烷氧基、C1-C2烷硫基、C1-C2烷基亚磺酰基和C1-C2烷基磺酰基;
R4基团之一在两个键接原子的两个邻位之一连接到K环,并且所述R4是C1-C4烷基、C1-C4卤代烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
每个R5独立地是H、C1-C4烷基、C1-C4卤代烷基、卤素、CN、NO2、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C2-C4烷氧基羰基;和一个R5是任选的W;和
W是苯环或5-或6-元杂芳环,各环任选被一至三个独立地选自R6的取代基取代。
更优选的W基团可独立地是苯基、吡唑、咪唑、三唑、吡啶或嘧啶,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤素或CN。上述优选的W基的实例包括在展示4中示为W-1至W-19的环,其中每个R6选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代炕氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤素和CN,q是1-3的整数。如同环中的碳原子一样,需要取代以配其化合价的氮原子被氢或R6取代。尽管(R6)q基团示于结构W-1至W-19中,但应注意到由于R6是任选取代基,因此其并不需存在。应注意到一些W基仅可被少于3个R6基团取代(例如W-5、W-6、W-10、W-12和W-13可被不多于两个R6取代)。应注意R6可通过置换氢原子连接于W基的任何可用的碳原子或氮原子上。特别优选的W基包括W-1和W-14。
展示4
优选5.优选4中化合物,其中
J是J-36;
R1是H;
R2是H或CH3;
R3是H;或C1-C4烷基,C1-C4烯基或C1-C4炔基,各基团任选被卤素、CN、OCH3、S(O)pCH3取代;
每个R4独立地是CH3、CF3、CN或卤素,并且一个R4基团在相邻于NR1C(=A)J部分的原子上连接于K环;
R5是H,C1-C4烷基,C1-C4卤代烷基,或W;
W是
V是N,CH,CF,CCl,CBr或CI;
每个R6和R8独立地是H,C1-C6烷基,C3-C6环烷基,C1-C6卤代烷基,卤素,CN,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C4卤代烷硫基;
m是1或2;和
p是0、1或2。
应注意J-36是J-1的子集,R8是R5的子集。
优选6.优选5中化合物,其中V是N。
优选7.优选5中化合物,其中V是CH、CF、CCl或CBr。
优选8.优选4中化合物,其中
J是J-37;
R1是H;
R2是H或CH3;
R3是H;或C1-C4烷基,C1-C4烯基或C1-C4炔基,各基团任选被卤素、CN、OCH3、S(O)pCH3取代;
每个R4独立地是CH3、CF3、CN或卤素,并且一个R4基团在相邻于NR1C(=A)J部分的原子上连接于K环;
R5是H,C1-C4烷基,C1-C4卤代烷基,或W;
W是
V是N,CH,CF,CCl,CBr或CI;
R6独立地是H,C1-C6烷基,C3-C6环烷基,C1-C6卤代烷基,卤素,CN,C1-C4烷氧基,C1-C4卤代烷氧基或C1-C4卤代烷硫基;
R9是H,C1-C6烷基,C1-C6卤代烷基,C3-C6烯基,C3-C6卤代烯基,C3-C6炔基或C3-C6卤代炔基;
m是1或2;和
p是0、1或2。
注意J-37是J-2的子集,R9是R5的子集。
最优选的是选自下列化合物的式I化合物:
1-(2-氯苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-三氟甲基)-1H-吡唑-5-甲酰胺(carboxamide),
1-(2-氯苯基)-4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]1H-吡唑-3-羧酸甲酯,
4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]-1-(2-甲基苯基)-1H-吡唑-3-羧酸甲酯,
4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-1-(2-甲基苯基)-3-(三氟甲基)-1H-吡唑-5-甲酰胺,
1-(2-氟苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺,
N-[2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-4,5-二氢-1-(2-甲基苯基)-3-(三氟甲基)-1H-吡唑-5-甲酰胺,和
1-(2,6-二氟苯基)-4,5-二氢-N-[2-甲基-6-[[1-甲基乙基)氨基]羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺。
本发明还涉及一种防治无脊椎害虫的组合物,含有生物有效量的式I化合物、其N-氧化物或其适宜的盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加成分。本发明还涉及一种含生物有效量的式I化合物、其N-氧化物或其适宜的盐和有效量的至少一种另外的生物活性化合物或试剂的组合物。本发明优选组合物是含上述优选化合物的那些组合物。
本发明还涉及一种防治无脊椎害虫的方法,包括用生物有效量的式l化合物、其N-氧化物或其适宜的盐(例如以本文所述的组合物形式)接触无脊椎害虫或其环境。本发明还涉及下述方法,其中用生物有效量的式I化合物、其N-氧化物或其适宜的盐,或含该化合物、其N-氧化物或其适宜的盐和生物有效量的至少一种另外的防治无脊椎害虫的化合物或试剂的组合物接触无脊椎害虫或其环境。优选的用法是包含上述优选化合物的那些方法。
重要的是式I化合物、及其N-氧化物或农业上适用的盐
其中
A和B独立地是O或S;
J是任选被取代的5-或6-元非芳族杂环;
K与两个相邻键接的碳原子一起形成苯环或5元或6元杂芳环,各环任选被取代;
R1是H;C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团均任选被取代;C2-C6烷基羰基;C2-C6烷氧基羰基;C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
R2是H,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,C1-C4烷氧基,C1-C4烷基氨基,C2-C8二烷基氨基,C3-C6环烷基氨基,C2-C6烷氧基羰基或C2-C6烷基羰基;
R3是H;G;C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,各基团均任选被取代;或
R2和R3与其相连的氮原子一起形成含2-6个碳原子和任选的一个另外的氮、硫或氧原子的环,并且该环可任选被取代;和
G是任选被取代的5-或6-元非芳族碳环或杂环,任选含一个或两个选自C(=O)、SO或S(O)2的环节。
此外还有因成本、合成的容易性和/或生物效力原因而重要的化合物:
精选物A.示为式Ia的式I化合物
其中
A和B独立地是O或S;
J是
或
K与两个键接原子一起形成苯环或5-或6-元杂芳环,各环任选被1-4个R4取代;
X是O或S;
R1是H;或C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团任选被一个或多个取代基取代,所述取代基选自卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
R1是C2-C6烷基羰基,C2-C6烷氧基羰基,C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
R2是H,C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,C1-C4烷氧基、C1-C4烷基氨基,C2-C8二烷基氨基,C3-C6环烷基氨基,C2-C6烷氧基羰基或C2-C6烷基羰基;
R3是H;G;C1-C6烷基,C2-C6烯基,C2-C6炔基,C3-C6环烷基,各基团均任选被一个或多个取代基取代,所述取代基选自卤素、G、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C6烷氧基羰基、C2-C6烷基羰基、C3-C6三烷基甲硅烷基,或苯基、苯氧基或5-或6-元杂芳环,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基或C3-C6三烷基甲硅烷基;C1-C4烷氧基;C1-C4烷基氨基;C2-C8二烷基氨基;C3-C6环烷基氨基;C2-C6烷氧基羰基或C2-C6烷基羰基;或
R2和R3与其相连的氮原子一起形成含2-6个碳原子和任选的一个另外的氮、硫或氧原子的环,该环可任选被1-4个取代基取代,所述取代基选自C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基;
G是5-或6-元非芳族碳环或杂环,任选含一个或两个选自C(=O)、SO或S(O)2的环节并且任选被1-4个取代基取代,所述取代基选自C1-C2烷基、卤素、CN、NO2和C1-C2烷氧基;
每个R4独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、或C3-C6三烷基甲硅烷基;或
每个R4独立地是苯基、苯甲基或苯氧基,各基团任选被一至三个取代基取代,所述取代基选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基和C3-C6三烷基甲硅烷基;
每个R5独立地是H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、卤素、CN、CO2H、CONH2、NO2、羟基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基、C3-C6三烷基甲硅烷基或W;
(R5)2当与相邻的碳原子连接时,与所述碳原子合为-OCF2O-、-CF2CF2O-或-OCF2CF2O-;
每个W独立地是苯基、苯甲基、苯甲酰基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环体系,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基或C3-C6三烷基甲硅烷基;
m是1-7;和
n是1-3。
精选物B.精选物A的化合物,其中K与两个键接原子一起形成任选被1-3个R4取代的苯环。
精选物C.精选物A的化合物,其中K与两个键接原子一起形成任选被1-3个R4取代的噻吩、吡唑、异_唑、吡啶或嘧啶。
精选物D.精选物B或精选物C的化合物,其中
A和B都是O;
n是1-2;
R1是H,C1-C4烷基,C2-C4烯基,C2-C4炔基、C3-C6环烷基,C2-C6烷基羰基或C2-C6烷氧基羰基;
R2是H,C1-C4烷基,C2-C4烯基,C2-C4炔基,C3-C6环烷基,C2-C6烷基羰基或C2-C6烷氧基羰基;
R3是C1-C6烷基,C2-C6烯基,C2-C6炔基或C3-C6环烷基,各基团均任选被一个或多个取代基取代,所述取代基选自卤素、CN、C1-C2烷氧基、C1-C2烷硫基、C1-C2烷基亚磺酰基和C1-C2烷基磺酰基;
R4基团之一在两个键接原子的两个邻位之一连接到K环,并且所述R4是C1-C4烷基、C1-C4卤代烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基或C1-C4卤代烷基磺酰基;
每个R5独立地是H、C1-C4烷基、C1-C4卤代烷基、卤素、CN、NO2、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C2-C4烷氧基羰基;和一个R5是任选的W;和
W是苯环或5-或6-元杂芳环,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C3-C6(烷基)环烷基氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基、C3-C8二烷基氨基羰基或C3-C6三烷基甲硅烷基。
精选物E.精选物D的化合物,其中
J是J-1;
R1和R2都是H;
R3是C1-C4烷基,C2-C4烯基或C2-C4炔基,各基团均任选被卤素、CN、OCH3、S(O)pCH3取代;
每个R4独立地是CH3、CF3、OCF3、OCHF2、S(O)pCF3、S(O)pCHF2CN或卤素;
每个R5独立地是H、卤素、C1-C4烷基、CF3、CHF2、CH2CF3、S(O)pCF3、S(O)pCHF2、S(O)pCH2CF3、S(O)pCF2CHF2或CN;和一个R5是任选的W;
W是苯基、吡唑、咪唑、三唑、吡啶或嘧啶环,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤素或CN;
m是1-2;和
n是0、1或2。
精选物F.精选物E的化合物,其中W是任选被C1-C4烷基、C1-C4卤代烷基、卤素或CN取代的苯基。
精选物G.精选物E的化合物,其中W是吡唑、咪唑、三唑、吡啶或嘧啶,各环任选被C1-C4烷基、C1-C4卤代烷基、卤素或CN取代。
精选物H.精选物D的化合物,其中
J是J-2;
R1和R2都是H;
R3是C1-C4烷基,C2-C4烯基或C2-C4炔基,各基团均任选被卤素、CN、OCH3、S(O)pCH3取代;
每个R4独立地是CH3、CF3、OCF3、OCHF2、S(O)pCF3、S(O)pCHF2、CN或卤素;
每个R5独立地是H、卤素、C1-C4烷基、CF3、S(O)pCF3、S(O)pCHF2、S(O)pCH2CF3、S(O)pCF2CHF2或CN;和一个R5是任选的W;
W是苯基、吡唑、咪唑、三唑、吡啶或嘧啶环,各环任选被一至三个取代基取代,所述取代基独立地选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤素或CN;
m是1-2;和
p是0、1或2。
式I的化合物可通过如方案1-28所述的下列方法和变化方法中的一种或多种制备。下文式1-59化合物中A、B、J、K、V、W、X、R1、R2、R3、R4、R5、m、n和q的定义如上所述。式Ib-Ie的化合物是式I化合物的不同子集,式1化合物也是式I化合物的子集。式1a-c、2a-g、9a-b、11a、12a、13a、14a-c、26a-c、42a-c和51a-d的化合物分别是式1、2、9、11、12、13、14、26、42和51化合物的不同子集。在这些方案中,除非另有说明,R10是C1-C4烷基。
典型方法示于方案1中,包括在除酸剂的存在下用式3的酰基氯偶合式2的邻位氨基羧酸酰胺,得到式Ib化合物。典型的除酸剂包括胺碱如三乙基胺、二异丙基乙基胺和吡啶;其他除酸剂包括氢氧化物如氢氧化钠和氢氧化钾和碳酸盐如碳酸钠和碳酸钾。在某些情况下,使用聚合物-载体的除酸剂如聚合物-结合的二异丙基乙基胺和聚合物-结合的二甲基氨基吡啶是有益的。在随后的步骤中,使用各种标准的硫代转移剂包括五硫化磷和Lawesson’s试剂可以将式Ib的酰胺转化成式Ic的硫代酰胺。
方案1
在方案2中,制备式Ib化合物的备选方法包括在脱水偶合剂如二环己基碳化二亚胺(DCC)的存在下用式4的酸偶合式2的酰胺。聚合物载体的试剂如聚合物结合的环己基碳化二亚胺在此是有益的。由于关于此类型反应的合成文献很多,方案1和2的合成方法仅是可用于通过用酸或酸等效物偶合胺制备式I化合物的有益方法的代表性实例。
方案2
本领域技术人员同样能认识到式3的酰氯可通过许多公知的方法用式4的酸制备。
式Id化合物的制备方法包括通过类似于方案1所述的方法用式3的酰氯偶合式5的邻-氨基羧酸酯(其中R10是C1-C4烷基),接着将酯基转化成酰胺官能团。此转化可通过用式7的胺进行胺化作用来实现。示于方案3中的路易斯酸如三甲基铝能促进此反应。
方案3
作为选择,可如方案4所示通过用碱如氢氧化钠水溶液进行皂化,得到式8的酸,接着通过类似于方案2所述的方法用式7的胺脱水偶合,从而将酯6转化成式Id的酰胺。
方案4
重要的化合物是K为任选被取代的苯环的式I化合物。典型方法详述于方案5,包括在除酸剂的存在下用式3的酰氯偶合式2a的邻氨基苯甲酸酰胺,得到式Ie的化合物(式I化合物的子集)。典型的除酸剂包括胺碱如三乙基胺、二异丙基乙基胺和吡啶;其他除酸剂包括氢氧化物如氢氧化钠和氢氧化钾和碳酸盐如碳酸钠和碳酸钾。在某些情况下,使用聚合物-载体的除酸剂如聚合物-结合的二异丙基乙基胺和聚合物-结合的二甲基氨基吡啶是有益的。在随后的步骤中,使用各种标准的硫代转移剂包括五硫化磷和Lawesson’s试剂可将式Ie的酰胺转化成式If的硫代酰胺(式I的子集)。
方案5
在方案6中,制备式Ie化合物的备选方法包括在脱水偶合剂如二环己基碳化二亚胺(DCC)的存在下用式4的酸偶合式2a的邻氨基苯甲酸酰胺。聚合物载体的试剂如聚合物结合的环己基碳化二亚胺在此又是有益的。由于关于此类型反应的合成文献很多,方案5和6的合成方法仅是可用于制备式I化合物的方法的代表性实例。
方案6
式2a的邻氨基苯甲酸酰胺通常可由相应的式9的2-硝基苯甲酰胺类通过硝基的催化加氢获得(方案7)。典型方法包括在金属催化剂如碳载钯或氧化铂的存在下在羟基溶剂如乙醇和异丙醇中用氢还原,得到式2b的化合物(式2a化合物,其中R1是H)。这些方法详细记载于化学文献。R1取代基如烷基、被取代的烷基等通常在此阶段通过已知方法包括直接烷基化或通过一般优选的胺还原性烷基化方法引入。通常采用的方法是在还原剂如氰基硼氢化钠的存在下将苯胺2b与醛结合,产生式2c化合物(式2a化合物,其中R1是烷基、烯基、炔基或其被取代的衍生物)。
方案7
式9a的中间体酰胺易于由市售的式10的2-硝基苯甲酸类制备(方案8)。形成酰胺的典型方法适用于此。这些方法包括使用例如DCC用式7的胺直接脱水偶合式10的酸,和将酸转化成活化形式如酰氯或酸酐,随后用胺偶合形成式9a的酰胺。氯甲酸乙酯是特别适用于此类包含酸活化的反应的试剂。关于此类反应的化学文献很多。通过使用市售的硫代转移剂如五硫化磷和Lawesson’s试剂能容易地将式9a的酰胺转化成式9b的硫代酰胺。
方案8
式2d和2e的中间体邻-氨基羧酸酰胺也能分别由式11和12的酸酐制备(方案9)。典型步骤包括在室温至100℃温度范围内在极性非质子传递溶剂如吡啶和二甲基甲酰胺中用酸酐化合等摩尔量的胺7。通过用已知的烷基化试剂R1-Lg(其中Lg是离去基团如卤素、磺酸烷基或芳基酯或硫酸烷基酯)碱催化烷基化式11的酸酐,得到式12的烷基取代的中间体,从而引入R1取代基如烷基和被取代的烷基。
式11的酸酐可通过描述于Coppola,Synthesis,1980,505和Fabis等,Tetrahedron,1998,10789中的方法制得。
方案9
式2f和2g的中间体邻氨基苯甲酸酰胺也能由式11a和12a的靛红酸酐制备(方案10)。典型步骤包括在室温至100℃温度范围内在极性非质子传递溶剂如吡啶或二甲基甲酰胺中用靛红酸酐化合等摩尔量的胺7。通过用已知的烷基化试剂R1-Lg(其中Lg是离去基团如卤素、磺酸烷基或芳基酯或OSO2OR1)碱催化烷基化式11a的靛红酸酐,得到式12a的烷基取代的中间体,从而引入R1取代基如烷基和被取代的烷基。
方案10
式Ig化合物(式I化合物,其中A是O,B是O,R1是H)的制备方法包括胺7与式13的杂环稠合_嗪酮反应(方案11)。典型步骤包括胺7与_嗪酮在溶剂如四氢呋喃或吡啶中在室温至溶剂回流温度的温度范围内化合。_嗪酮类详细记载于化学文献中并可通过已知方法得到,所述已知方法包含用酰氯偶合邻-氨基羧酸。关于杂环稠合_嗪酮类的合成和化学参见Jakobsen等,Biorganic and Medicinal Chemistry,2000,8,2803-2812和其中所引文献。
方案11
式Ih化合物(式I化合物,其中A是O,B是O,R1是H,K是任选被取代的苯基)的制备方法包括胺7与式13a的苯并_嗪酮反应(方案12)。典型步骤包括胺与苯并_嗪酮在溶剂如四氢呋喃或吡啶中在室温至溶剂回流温度的温度范围内化合。苯并_嗪酮类详细记载于化学文献中并可通过已知方法得到,所述已知方法包含用酰氯偶合邻-氨基苯甲酸或靛红酸酐。关于苯并_嗪酮类的合成和化学参见Jakobsen等,Biorganic and Medicinal Chemistry,2000,8,2095-2103和其中所引文献。还可参见Coppola,J.Heterocyclic Chemistry,1999,36,563-588。
方案12
特殊的J-基团(及其前体)的制备方法概述于方案13-28。在这些方案中,Z是连接J的任何基团,该基团能被化学转化而得到式I化合物。例如Z可以是CO2H(并且Z-J对应于式4),CO2(C1-C4烷基),CN或CH2OH。其中Z是CO2(C1-C4烷基)或CN的Z-J化合物可通过水解转化成式4化合物。关于将酯或腈转化成相应的羧酸的文献很多。其中Z是CH2OH的化合物Z-J可通过氧化转化成式4化合物。为将这些化合物转化成式4的化合物,有许多氧化方法可利用,一种选择(精选物)可见于Comprehensive Organic Transformations,Larock,R.C.,VCHPublishers,Inc.,1989。Z还可以是对应于展示5中归纳的上述中间体的其他基团。
展示5
一些Z-J化合物的典型制备方法示例于方案13,包含用式14的链烯环加成式15或16的化合物,得到式17化合物。
方案13
式18或19化合物的环加成作用分别得到式20和21的化合物(方案14)。
方案14
环加成作用可以是2+4型如杂-狄尔斯-阿尔德反应(见例如Waldmann,H,Synthesis,1994,6,535)或可以是2+3型如多种1,3-偶极环加成之一种(见1,3-Dipolarcycloaddition Chemistry,Padwa,A,Ed.,J.Wiley&Sons,1983)。
某些式14a或14b化合物可通过采用与上述方案1、2、5和6中所述类似的方法用式22的丙烯酸或式23的酰基氯处理式2或2a化合物制备(方案15)。式14c化合物的制备可通过用式23化合物处理式5化合物,接着采用与方案3和4所述类似的方法用式7的胺进一步处理。
方案15
作为选择,如方案16所示,一些式Z-J化合物的制备可通过用例如式26的乙醛酰或醛基(aldehydo)衍生物环加成式27或28的化合物,分别得到式29和30的化合物。
方案16
作为选择,式33化合物(Z-J化合物的子集)可通过用式31的肟环加成式32的链烯来制备(方案17)。通常,环加成是通过用卤化剂如N-氯琥珀酰亚胺(NCS)处理式31的肟,接着在式32链烯的存在下用适宜的碱如三乙基胺处理来完成的。
方案17
有些式26a或26b化合物可通过采用与方案1、2、5和6所述类似的方法用式34的水合乙醛酸或式35的水合乙醛酸酰氯处理式2或2a的化合物来制备(方案18)。式26c化合物可通过用式35化合物处理式5化合物,接着采用与方案4类似的方法用式7的胺进一步处理来制备。
方案18
有些式Z-J化合物(式40和42)也可通过如方案19所示分别用C1单元(式26)或C2单元(式41)环化式38的酰肼或式39的硫代酰肼来制备。
方案19
有些式42化合物可由式38或39化合物来制备,通过用式43的表卤代醇类处理可得到式42a化合物(方案20)。氧化式42a化合物,得到式42b化合物,该化合物是式4酸的子集。
方案20
一些式45的式Z-J化合物也可通过还原式44的芳族杂环来制备(方案21)。
方案21
式31的肟可通过在本领域技术人员公知的许多条件下用羟胺缩和式26化合物而获得(方案22)。
方案22
一些式47的杂环酸(式4的子集)可通过式46的非芳族杂环的锂化(例如使用丁基锂在四甲基亚乙基二胺(TMEDA)的存在下)和用二氧化碳处理(方案23)制得。
方案23
一些式51的杂环酸可经方案24-25所示反应顺序制备。
如方案24所示,在碱和溶剂的存在下用R10是C1-C4烷基的式49化合物(可以使用其延胡索酸酯或马来酸酯或混合物)处理式48化合物。碱一般是金属醇盐如甲醇钠、甲醇钾、乙醇钠、乙醇钾、叔丁醇钾、叔丁醇锂等。相对式48化合物应使用大于0.5当量碱,优选0.9-1.3当量。应使用大于1.0当量的式49化合物,优选1.0-1.3当量。可使用极性质子和极性非质子传递有机溶剂,如醇类、乙腈、四氢呋喃、N,N-二甲基甲酰胺、二甲基亚砜等。优选溶剂是醇类如甲醇和乙醇。特别优选该醇与构成延胡索酸酯或马来酸酯和醇盐碱的醇是相同的。反应的进行通常是通过在溶剂中混合式48化合物和碱。混合物可以被加热或冷却至需要的温度,在一段时间内添加式49化合物。通常反应温度介于0℃和所用溶剂的沸点之间。反应可在大于大气压的条件下进行以便提高溶剂的沸点。温度一般优选大约30-90℃。加料时间应在传热许可的情况下可以尽可能地快。一般加料时间介于1分钟和2小时之间。最佳反应温度和加料时间随式48和式49化合物的特性而变。加料后,将反应混合物在反应温度下保持一段时间。根据反应温度,需要的保持时间可以是0-2小时。一般保持时间是10-60分钟。然后可通过添加有机酸如乙酸等或无机酸如盐酸、硫酸等使反应物料酸化。根据反应条件和分离方式,可制备其中R11是H的式50化合物或R11是C1-C4烷基的式50化合物。例如,当反应混合物中有水时,R11是C1-C4烷基的式50化合物可原位水解成R11是H的式50化合物。需要的产物一式50化合物可通过本领域技术人员已知的方法如结晶、萃取或蒸馏分离。
方案24
在下一步骤中,如方案25中的步骤1所示,通常在溶剂的存在下用卤化剂处理式50化合物。可用的卤化剂包括三卤氧化磷、三卤化磷、五卤化磷、亚硫酰二氯、二卤代三烷基正膦、二卤代二苯基正膦、草酰氯和光气。优选的是三卤氧化磷和五卤化磷。为了获得完全转化,应使用至少0.33当量三卤氧化磷对式50化合物,优选0.33-1.2当量。为了获得完全转化,应使用至少0.20当量五卤化磷对式50化合物,优选约0.20-1.0当量。对于此反应而言,R11是C1-C4烷基的式50化合物是优选的。
此卤化反应的典型溶剂包括卤代烷烃如二氯甲烷、氯仿、氯丁烷等,芳族溶剂如苯、二甲苯、氯苯等,醚如四氢呋喃、对-二氧杂环己环、二乙醚等,和极性非质子传递溶剂如乙腈、N,N-二甲基甲酰胺等。有机碱如三乙基胺、吡啶、N,N-二甲基苯胺等可任选添加。添加催化剂如N,N-二甲基甲酰胺也是任选的。优选方法是溶剂为乙腈且不使用碱。通常,当使用乙腈溶剂时,碱或催化剂都不需要。优选方法是通过在乙腈中混合式50化合物进行的。然后在适当的时间内添加卤化剂,随后将混合物保持在需要的温度下直至反应完成。反应温度通常介于20℃和乙腈的沸点间,反应时间一般少于2小时。然后用无机碱如碳酸氢钠、氢氧化钠等,或有机碱如乙酸钠中和反应物料。需要的产物-式51化合物可通过本领域技术人员已知的方法包括结晶、萃取和蒸馏分离。
方案25
式51a化合物中的卤素可被亲核试剂(Nuc)如C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基或C1-C4卤代烷硫基的钠盐或钾盐置换(方案25中步骤3)。这些置换可在溶剂如醚类如四氢呋喃、对-二氧杂环己环、二乙醚等,和极性非质子传递溶剂如乙腈、N,N-二甲基甲酰胺等中进行。反应温度一般介于20℃和溶剂的沸点间。
式51a或式51c的化合物(其中R11是C1-C4烷基),一种酯,可分别水解成式51b或式51d的羧酸化合物(其中R11是H)(方案25中的步骤2或步骤4)。这些水解可由酸、金属离子和酶催化。作为能用于催化这些水解的酸的实例应注意碘代三甲基硅烷(参见Advanced OrganicChemistry,第三版,Jerry March,John Wiley & Sons,Inc.New York,1985,第334-338页可查看这些方法的综述)。对于式51化合物的水解不建议采用碱催化的水解方法,该方法可导致分解。羧酸可通过本领域技术人员已知的方法包括结晶、萃取和蒸馏分离。
一些式55的杂环酸可经方案26-28所示反应顺序制备。
如方案26所示,式53化合物可通过在适宜的有机溶剂中用适宜的碱处理式52化合物来制备。适宜的碱的实例包括(但不限于)氢化钠、叔丁醇钾、dimsyl sodium(CH3SOCH2 -Na+)、碱金属(如锂、钠或钾)碳酸盐或氢氧化物、四烷基(如甲基、乙基或丁基)氟化铵或氢氧化物,或2-叔丁基亚胺基-2-二乙基氨基-1,3-二甲基-全氢-1,3,2-diazaphosphonine。适宜的有机溶剂的实例包括(但不限于)丙酮、乙腈、四氢呋喃、二氯甲烷、二甲基亚砜、或N,N-二甲基甲酰胺。环化反应通常在大约0-120℃温度范围内进行。溶剂、碱、温度和加料时间的影响都是相互依赖的,反应条件的选择对使副产品的形成减少到最小很重要。优选的碱是氟化四丁基铵。然后用适宜的酸(例如乙酸)使反应中形成的中间体式53(其中M+是源于碱的适宜的抗衡离子)质子化,产生式54a化合物,其中R12是H。本领域技术人员知道中间体如53能通过添加适宜的烷基化试剂烷基化,产生式54b化合物,其中R12是C1-C4烷基。作为选择,式54b化合物可在单独的化学步骤中使用适宜的碱和烷基化试剂由式54a化合物制得。适宜的烷基化试剂包括C1-C4卤代烷(例如碘乙烷)、硫酸酯(例如二甲基硫酸酯)和磺酸酯(例如对-甲苯磺酸甲酯)。
式54b化合物的裂解可得到式55化合物。此转化可由碱、亲核试剂、金属离子和酶催化。一些裂解方法包括在溶剂如N,N-二甲基甲酰胺或吡啶中用氯化锂或碘化锂处理,在甲苯中用碘化镁处理,和在二甲基亚砜或水中用叔丁醇钾处理。酯裂解方法综述于Greene,T.W.;Wuts,P.G.M.Protective Groups in Organic Synthesis,第2版;Wiley:New York,1991。对于式54b化合物的水解不建议采用酸催化的水解方法,该方法可导致分解。羧酸可通过本领域技术人员已知的方法包括结晶、萃取和蒸馏分离。
方案26
式52化合物可通过在除酸剂如三乙基胺的存在下在适宜的有机溶剂中用式57化合物处理式56化合物来制备。适宜的有机溶剂的实例包括(但不限于)二氯甲烷和四氢呋喃。该反应通常在介于约0-100℃间的温度下进行。方案27阐明了此转化。
方案27
如方案28所示,式56的腙化合物可通过在溶剂如水、甲醇或乙酸中用式59化合物处理式58肼化合物而制备。本领域技术人员认可,根据式56腙的分子取代模式,此反应可能需要任选酸的催化,还可能需要高温。
方案28
公认上述制备式I化合物的一些试剂和反应条件可能不兼容中间体中存在的某些官能团。在这些情况下,在合成中并入保护/去保护顺序或官能团互变将有助于获得需要的产物。保护基的使用和选择对化学合成领域的技术人员来说是显而易见的(见例如Greene,T.W.;Wuts,P.G.M.Protective Groups in Organic Synthesis,第2版;Wiley:New York,1991)。本领域技术人员能认可在一些情况下,在导入任一方案中描述的特定试剂后,可能必需进行未详细描述的额外的常规合成步骤以完成式I化合物的合成。本领域技术人员也能认可为制备式1化合物,可能必需以不同于上述特定顺序的顺序进行上述方案中例举的多个步骤的结合。
本领域技术人员还能认可式I化合物和本文所述的中间体可进行各种亲电子、亲核、自由基、有机金属的氧化和还原反应以添加取代基或改变已有的取代基。
无需进一步详细阐明,相信本领域技术人员利用上述描述能最全面程度地应用本发明。因此,下列实施例应看作仅仅是说明性的,并非以任何方式限制所公开的内容。除了色谱溶剂混合物或另有说明以外,百分数是重量百分数。除非另有说明,色谱溶剂混合物的份数和百分数是体积份数和体积百分数。1H NMR谱记录的是距四甲基硅烷的ppm低磁场;s是单峰,d是双峰,t是三重峰,q是四重峰,m是多重峰,dd是双峰的双峰,dt是三重峰的双峰,br s是宽单峰。
实施例1
制备1-(2-氯苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-三氟甲基)-1H-吡唑-5-甲酰胺
步骤A:3-甲基-N-(1-甲基乙基)-2-硝基苯甲酰胺的制备
将含3-甲基-2-硝基苯甲酸(2.00g,11.0mmol)和三乙基胺(1.22g,12.1mmol)的25ml二氯甲烷溶液冷却至10℃。仔细地添加氯甲酸乙酯,形成固体沉淀。将反应混合物搅拌30分钟后,添加异丙基胺(0.94g,16.0mmol),得到均匀溶液。将反应混合物再搅拌1小时,倒入水中,用乙酸乙酯萃取。有机提出物用水洗,过硫酸镁干燥,减压蒸发,得到1.96克标题化合物白色固体,熔点126-128℃。
1H NMR(CDCl3)δ1.24(d,6H),2.38(s,3H),4.22(m,1H),5.80(br s,1H),7.4(m,3H)。
步骤B:制备2-氨基-3-甲基-N-(1-甲基乙基)苯甲酰胺
在345kPa(50磅/平方英寸)下在40ml乙醇中将步骤A中的2-硝基苯甲酰胺(1.70g,7.6mmol)经5%Pd炭氢化。当氢气吸收停止,将反应混合物过Celite_过滤,用乙醚洗Celite_。滤出液减压蒸发,得到1.41g标题化合物固体,熔点149-151℃
1H NMR(CDCl3)δ1.24(dd,6H),2.16(s,3H),4.25(m,1H),5.54(br s,2H),5.85(brs,1H),6.59(t,1H),7.13(d,1H),7.17(d,1H)。
步骤C:制备3-甲基-N-(1-甲基乙基)-2-[(1-氧代-2-丙烯基)氨基]苯甲酰胺
向步骤B的标题化合物(0.93g,4.8mmol)的二氯甲烷(10ml)溶液中添加三乙基胺(0.876ml,6.2mmol),将混合物冷却至0℃。然后添加烯丙酰氯(0.433ml,5.3mmol),并将混合物升温至环境温度,搅拌过夜。然后添加二甲基氨基吡啶(1.0g,7.7mmol),接着添加烯丙酰氯(0.475ml,5.8mmol)。将混合物在环境温度下搅拌0.5小时,用1N盐酸稀释,并用二氯甲烷萃取两次。将有机提出物干燥(MgSO4)和浓缩,得到步骤C产物(0.62g),为白色固体。
1H NMR(CDCl3)δ:9.1(bs,1H);7.4-7.1(m,3H),6.5-6.3(m,2H),6.1-6.0(bd,1H),5.8-5.7(m,1H),4.3-4.1(m,1H),2.25(s,3H),1.20(d,6H)。
步骤D:制备N-(2-氯苯基)-2,2,2-三氟乙烷腙酸
向0℃的2-氯苯基肼(1.65g,11.6mmol)的四氢呋喃(40ml)溶液中添加三氟乙酸酐(1.8ml,12.8mmol)。令混合物逐步升温至环境温度,搅拌过夜。将混合物浓缩,再溶解于乙醚中,并用NaHCO3饱和溶液洗两次。将混合物干燥(MgSO4)和浓缩,得到步骤D的标题化合物,为浅橙色固体(2.77g)。
1H NMR(CDCl3)δ:7.32(dd,1H);7.20(s,1H),6.91(td,1H),6.86(dd,1H),6.49(s,1H)。
步骤E:用N-(2-氯苯基)-2-,2,2-三氟乙烷腙酸制备4-甲基苯磺酸酐
向步骤D的标题化合物(2.77g,11.6mmol)的乙酸乙酯(20ml)溶液中添加4-甲基吗啉(1.4ml,12.8mmol),接着添加对-甲苯磺酰氯(2.43g,12.8mmol)。将混合物在环境温度下搅拌过夜,然后用乙醚稀释,用1N盐酸洗两次,干燥(MgSO4)和浓缩。残余物用己烷研制,产生步骤E的标题化合物,为白色固体。
1H NMR(CDCl3)δ:9.0-8.9(bs,1H),8.0-7.9(d,2H),7.6-7.5(d,1H);7.5-7.4(d,2H),7.4-7.2(m,2H),7.0-6.9(t,1H),2.50(s,3H)。
步骤F:制备1-(2-氯苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-三氟甲基)-1H-吡唑-5-甲酰胺
向步骤C的标题化合物(0.24g,0.98mmol)的乙酸乙酯(15ml)溶液中添加4-甲基吗啉(0.267ml,2.45mmol)和步骤E的化合物(0.421g,1.08mmol),将混合物加热回流24小时。将混合物冷却,用二氯甲烷稀释,用水洗,干燥(MgSO4)和浓缩。残余物通过快速柱色谱(5%,然后10%,然后20%乙酸乙酯的甲苯溶液)纯化,产生实施例1的标题化合物,本发明的一种化合物,为白色固体(21mg)。
1H NMR(CDCl3)δ:9.4(bs,1H),7.6-7.5(d,1H),7.4-7.1(m,6H),5.8(bd,1H),5.4(dd,1H),4.3-4.1(m,1H),3.6-3.4(m,2H),1.84(s,3H),1.3-1.2(m,6H)。
实施例2
制备1-(2-氯苯基)-4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]-1H-吡唑-3-羧酸甲酯
步骤A:制备(2E)-[(2-氯苯基)亚肼基]乙酸甲酯
向乙醛酸甲酯(6.8g,77mmol)的甲醇(150ml)溶液中添加2-氯苯基肼盐酸化物(12.5g,77mmol),并将混合物加热回流过夜,冷却和浓缩。残余物再溶解于甲苯中并浓缩,得到步骤A的标题化合物。
1H NMR(CDCl3)δ:12.6(bs,1H),7.7-7.6(d,1H),7.4-7.3(d,1H),7.3-7.2(m,1H),7.0-6.9(m,1H),6.77(s,1H),3.84(s,3H)。
步骤B:制备(2Z)-溴[(2-氯苯基)亚肼基]乙酸甲酯
向步骤A标题化合物(16.5g,77mmol)的四氢呋喃(150ml)溶液中添加N-溴代琥珀酰亚胺(13.7g,77mmol),并将混合物在环境温度下搅拌2小时。混合物浓缩并用己烷萃取,再将己烷溶液浓缩,得到步骤B的标题化合物(16g),为橙色固体。
1H NMR(CDCl3)δ:8.93(bs,1H),7.63(dd,1H),7.34(dd,1H),7.28(m,1H),6.98(m,1H),3.95(s,3H)。
步骤C:制备1-(2-氯苯基)-4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]-1H-吡唑-3-甲酸甲酯
向含实施例1步骤C的产物(1.0g,4.1mmol)和实施例2步骤B的产物(2.4g,8.2mmol)的乙酸乙酯(50ml)溶液中添加4-甲基吗啉(1.1ml,12.3mmol),将混合物加热回流2小时。再加入一定量的4-甲基吗啉(1.1ml,12.3mmol),接着添加步骤B的产物(2.4g,8.2mmol),将反应混合物加热回流过夜。将混合物在环境温度下搅拌2天,用乙酸乙酯稀释,用1N盐酸洗,干燥(MgSO4)和浓缩。残余物通过快速柱色谱(10%,然后20%,然后30%乙酸乙酯的甲苯溶液)纯化,产生实施例2的标题化合物,本发明的一种化合物(22mg),为灰白色固体(21mg)。
1H NMR(CDCl3)δ:9.4-9.3(bs,1H),7.6(d,1H),7.4-7.3(d,1H),7.3-7.0(m,5H),5.8(d,1H),5.5(dd,1H),4.2-4.1(m,1H),3.89(s,3H),3.7-3.4(m,2H),1.81(s,3H),1.3-1.2(m,6H)。
实施例3
制备4-(2-氯苯基)-5,6-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-2-(三氟甲基)-4H-1,3,4-_二嗪-5-甲酰胺
步骤A:制备4-(2-氯苯基)-5,6-二氢-2-(三氟甲基)-4H-1,3,4-_二嗪-5-甲醇
向实施例1步骤D的标题化合物(9.0g,37.7mmol)的N,N-二甲基甲酰胺(100ml)溶液中添加碳酸钾(7.8g,56.6mmol)和表溴醇(5.6ml,45.3mmol),并将混合物在90℃加热1小时。然后冷却混合物,用乙醚稀释,用水洗两次。将溶液干燥(MgSO4)、浓缩和通过快速柱色谱(硅胶,20%乙醚的石油醚溶液)纯化,产生步骤A的标题化合物(2.4g),其中混杂等摩尔量的区域异构体,为橙色油。
1H NMR(CDCl3)δ7.5-7.2(m,3H),7.2-7.1(m,1H),4.72(dd,1H),4.60(dd,1H),4.2-3.7(2xm,2H),3.7(m,1H)。
步骤B:制备4-(2-氯苯基)-5,6-二氢-2-(三氟甲基)-4H-1,3,4-_二嗪-5-甲酸
向步骤A的标题化合物(2.1g,7.1mmol)的二氯甲烷(30ml)溶液中添加干燥的粉状4_分子筛(9g)和氯铬酸吡啶鎓(1.54g,7.1mmol),并将混合物在环境温度下搅拌过夜。然后将混合物通过硅胶垫过滤,用乙醚洗,和浓缩。残余物通过快速柱色谱(硅胶,20%、然后40%乙醚的石油醚溶液)纯化,得到1.1g无色油。然后将此物质溶解于叔丁醇(35ml)和水(35ml)中。然后添加含2-甲基-2-丁烯(1.0M的四氢呋喃溶液,35ml)、磷酸二氢钠(3.16g,26.4mmol)和氯酸钠(2.9g,32.0mmol)的溶液,并将混合物在环境温度下搅拌过夜。将混合物用二氯甲烷萃取两次,干燥(MgSO4),浓缩和通过快速柱色谱(硅胶,40%乙醚的石油醚溶液,然后乙醚,然后10%甲醇的二氯甲烷溶液)纯化,得到步骤B的标题化合物(58mg),为无色油。
1H NMR(CDCl3)δ7.6-7.5(d,1H),7.4-7.2(m,2H),7.1(t,1H),5.6-5.0(bs,1H),4.9(s,1H),4.8(d,1H),4.6(m,1H)。
步骤C:制备4-(2-氯苯基)-5,6-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-2-(三氟甲基)-4H-1,3,4-_二嗪-5-甲酰胺
向步骤B的标题化合物(58mg,0.19mmol)的二氯甲烷(10ml)溶液中加两滴N,N-二甲基甲酰胺,接着添加草酰氯(20μl,0.23mmol),将混合物在环境温度下搅拌45分钟。然后浓缩混合物,再溶解于二氯甲烷(10ml)中。然后添加实施例1步骤B的标题化合物(36mg,0.19mmol),接着添加N,N-二甲基氨基吡啶(2mg,0.02mmol)和三乙基胺(40μl,0.29mmol),将混合物在环境温度下搅拌过夜。之后添加碳酸氢钠的饱和溶液,将混合物通过Celite_筒过滤、浓缩和通过快速柱色谱(硅胶,20%、然后40%、然后60%乙醚的石油醚溶液)纯化,产生实施例3的标题化合物(8mg),为白色固体。
1H NMR(CDCl3)δ:9.6(s,1H),7.6-7.1(m,7H),5.9-5.8(d,1H),5.0-4.9(dd,1H),4.8-4.7(m,1H),4.3(dd,1H),4.2-4.1(m,1H),2.10(s,3H),1.3-1.2(m,6H)。
通过本文上述工艺加上本领域已知方法,可制备表1-13中的下列化合物。表中使用下列缩写:t表示叔,s表示仲,i表示异,Me表示甲基,Et表示乙基,Pr表示丙基,i-Pr表示异丙基,t-Bu表示叔丁基。
表1
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HHHHMeHHHHMeHHHHMe | ClClClClClBrBrBrBrBrClClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | ClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIII | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIII | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCIClClClClClClCl | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3FFFFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | BrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHEtHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2F3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | BrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIlIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | BrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | ClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | BrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | ClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIIIIIIIlIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
表2
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
Cl | CF3 | CH3 | H | Me | H | Cl | CF3 | Cl | H | Me | H |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClCl | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClCl | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHEtHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIII | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIII | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OOH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBr | OCH2CF3OCH2CF3OCH2CF3 | FFF | CF3CF3CF3 | i-Prt-BuMe | HHMe | BrBrBr | OCH2CF3OCH2CF3OCH2CF3 | BrBrBr | CF3CF3CF3 | i-Prt-BuMe | HHMe |
表3
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | BrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | BrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | ClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | ClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIIIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClCl | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3F | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClH | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClCl | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClH | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHEtH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeIIHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | BrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | BrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIlIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMe |
表4
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMe | HHHHMeHHHHMe | ClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClCl | HHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMe | HHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH2CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | BrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClCl | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBr | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHH | i-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBr | ClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHH | i-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHEtHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | BrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | BrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | BrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | ClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | ClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | ClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | ClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
表5
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Pri-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIlIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClCl | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClCl | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHEtHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeBti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-EluMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CP3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrClClClClClBrBrBrBrBr | BrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HHMeHHHHMeHHHHMe | BrBrBrClClClClClBrBrBrBrBr | BrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HHMeHHHHMeHHHHMe |
表6
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHH | ClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | ClClClClClClClClClClClClClCl | HHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3Cl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMelEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIIIlIIIIIIIIIIIIIIIIIIIII | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHEtHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
表7
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeECi-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CCF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IlIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClCl | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClClClClClCl | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClHHHHH | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHEtHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFF | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | ClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrClClClClClBrBrBrBrBr | BrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Pri-BuMe | HHMeHHHHMeHHHHMe | BrBrBrClClClClClBrBrBrBrBr | BrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HHMeHHHHMeHHHHMe |
表8
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHH | ClClClClClBrBrBrBrBrClClClCl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClCl | ClClClClClClClClClClClClClCl | HHHHHHHHHHHHHH | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3Cl | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | HHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | ClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrCl | ClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHFFFFFFFFFFF | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | ClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFClClClClClClClCl | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBrBrBrBr | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrII | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CF3CH3CH3 | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | IIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3 | ICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | ICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | CH3CH3CH3CH3CH3CH3CH3CH3CH3FFFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBr | OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBrBrBrBr | ClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3ClClClClClHHHHHHHHHHHHHHHHHHHHHHHHHHHH | Eti-Prt-BuMen-Prn-Bus-Bui-BuEtMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHEtHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | BrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClCl | BrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHFFFFFFFFFFFFFFFFFFFFFFFFF | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH | BrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClCl | BrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClClClBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | FFFFFFFFFFFFFFFClClClClClClClClClClClClClClClClClClClClClCl | MeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEt | HHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH | ClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBr | BrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | ClClClClClClClClClClClClClClClClClClBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | i-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-Bu | HHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH | BrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBr | ClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClClClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrIIIIIIIIIIIIIIII | MeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMe | MeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | FFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFFF | IIIIIIIIIIIIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH | BrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBrClClCl | ClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3ClClCl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | IIIIIIIIIIlIIIIIIIIIIIIICF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | Eti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Pr | HHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMeHHH |
R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 | R6(a) | R5(a) | R4(a) | R4(b) | R3 | R2 |
ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | FFFFFFFFFFFFFFFFFFFFFFFFFFF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe | ClClBrBrBrBrBrClClClClClBrBrBrBrBrClClClClClBrBrBrBrBr | ClClClClClClClBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | t-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMeMeEti-Prt-BuMe | HMeHHHHMeHHHHMeHHHHMeHHHHMeHHHHMe |
表9
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHBrBrBrH | i-Pri-Pri-Prt-But-But-BuMeMeMeEtEtEti-Pri-Pri-Prt-But-But-Bui-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CClCClCFCClCClCFCClCClCFCClCClCFCClCClCFCClCClCFCClCClCFCClCClCFCCl | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFN |
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
ClFMeClF | CF3CF3CF3CF3CF3 | MeMeMeMeMe | MeMeMeMeMe | HHHHH | i-Pri-Pri-Pri-Pri-Pr | CClCFCHCHCH | ClFMeClF | CF3CF3CF3CF3CF3 | HHMeMeMe | ClClMeMeMe | HHHHH | CH2C≡CHCH2C≡CHi-Pri-Pri-Pr | NNNNN |
表10
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-BuMe | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCH | MeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHBrBrBrBrBrBrBrBrBrH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCH |
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R3 | V | |
ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeEtEtEtEtEtEtEtEtEti-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-Bu | CHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN | ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeMeMeMeMeMeMeHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | CHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN |
表11
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-BuMeMeMeMeMeMeMe | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFN | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHBrBrBrBrBrBrBrBrBrHHHHHHH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFN |
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeEtEtEtEtEtEtEtEtEti-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-Bu | NNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN | ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | NNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN |
表12
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-BuMeMeMeMeMeMeMe | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFN | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMe | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHMeMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHBrBrBrBrBrBrBrBrBrHHHHHHH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFN |
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(B) | R3 | V |
ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeEtEtEtEtEtEtEtEtEti-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-Bu | NNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN | ClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | NNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN |
表13
X是O
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-BuMeMeMeMeMeMe | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCF | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHMeMeMeMeMeMe | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHBrBrBrBrBrBrBrBrBrHHHHHH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCF |
X是O
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeEtEtEtEtEtEtEtEtEti-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-Bu | NNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | MeMeMeHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeClClClClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | NNNCHCHCHCClCC1CFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNN |
X是S
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClF | CF3CF3CF3 | HHH | MeMeMe | HHH | i-Pri-Pri-Pr | CHCHCH | MeClF | CF3CF3CF3 | HHH | MeMeMe | HHH | CH2C≡CHCH2C≡CHCH2C≡CH | CHCHCH |
X是S
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3BrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-BuMeMeMeMeMeMeMeMeMeEtEtEtEtEtEtEtEtEti-Pri-Pri-Pr | CClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCCCCCFNNNCHCHCH | MeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCO2MeCF3CF3CF3 | HHHHHHHHHHHHHHHMeMeMeMeMeMeMeMeMeHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeClClCl | HHHHHHBrBrBrBrBrBrBrBrBrHHHHHHHHHHHHHHHHHHHHH | CH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHi-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pri-Pr | CClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCHCClCClCFNNNCHCHCH |
X是S
R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V | R6 | R5(a) | R5(b) | R4(a) | R(b) | R3 | V |
MeClFMeClFMeClFMeClFMeClF | BrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHH | MeMeMeMeMeMeClClClClClClClClCl | HHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-Prt-But-But-But-But-But-But-But-But-Bu | CClCClCFNNNCHCHCHCClCClCFNNN | MeClFMeClFMeClFMeClFMeClF | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | HHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClCl | HHHHHHHHHHHHHHH | i-Pri-Pri-Pri-Pri-Pri-PrCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CHCH2C≡CH | CClCClCFNNNCHCHCHCClCClCFNNN |
制剂/应用
本发明的化合物通常可用作与农业上适用的载体的制剂或组合物,所述载体包括至少一种液体稀释剂、固体稀释剂或表面活性剂。选择的制剂或组合物成分要与活性成分的物理性能、施用方式和环境因素如土壤类型、湿度和温度相一致。有用的制剂包括液体制剂如可任选被稠化成凝胶的溶液(包括乳油)、悬浮剂、乳剂(包括微乳剂和/或悬乳剂)等等。有用制剂还包括固体制剂如可具水分散性(“可湿性”)或水溶性粉尘剂、粉剂、颗粒剂、丸剂、片剂、膜剂等等。活性成分可以被(微)胶囊化,和进一步形成悬浮剂或固体制剂;作为选择,活性成分的整个制剂可以被胶囊化(或“涂外涂层”)。包胶囊能控制或延迟活性成分的释放。可喷雾制剂可稀释于适宜的介质中,以大约一至几百升/公顷的喷雾体积应用。高浓度组合物主要用作中间体以进一步配制。
制剂一般含在下列大致范围内的有效量的活性成分、稀释剂和表面活性剂,并且合计达100重量%。
重量百分数 | |||
活性成分 | 稀释剂 | 表面活性剂 | |
水分散性和水溶性颗粒剂、片剂和粉剂 | 5-90 | 0-94 | 1-15 |
悬浮剂、导剂、溶液(包括乳油) | 5-50 | 40-95 | 0-15 |
粉尘剂 | 1-25 | 70-99 | 0-5 |
颗粒剂和丸剂 | 0.01-99 | 5-99.99 | 0-15 |
高浓度组合物 | 90-99 | 0-10 | 0-2 |
典型的固体稀释剂描述于Watkins等,Handbook of Insecticide DustDiluents and Carriers,第二版,Dorland Books,Caldwell,新泽西。典型的液体稀释剂描述于Marsden,Solvent Guide,第二版,Interscience,纽约,1950。McCutcheon’s Detergents and Emulsifiers Annual,AlluredPubl.Corp.,Ridgewood,新泽西,以及Sisely and Wood,Encyclopediaof Surface Active Agents,Chemical Publ.Co.,Inc.,纽约,1964列出了表面活性剂和推荐用途。所有制剂都可含少量添加剂以减少泡沫、结块、腐蚀、微生物生长等,或增稠剂以增加粘度。
表面活性剂包括例如聚乙氧基化醇、聚乙氧基化烷基酚、聚乙氧基化脱水山梨醇脂肪酸酯、磺基琥珀酸二烷基酯、烷基硫酸盐、烷基苯磺酸盐、有机硅酮、N,N-二烷基牛磺酸盐、木质素磺酸盐、萘磺酸盐甲醛缩和物、聚羧酸酯和聚氧乙烯/聚氧丙烯嵌段共聚物。固体稀释剂包括例如粘土如膨润土、蒙脱土、硅镁土和高岭土、淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠和碳酸氢钠、和硫酸钠。液体稀释剂包括例如水、N,N-二甲基甲酰胺、二甲基亚砜、N-烷基吡咯烷酮、乙二醇、聚丙二醇、烷属烃、烷基苯、烷基萘、橄榄油、蓖麻油、亚麻籽油、桐油、芝麻油、玉米油、花生油、棉籽油、大豆油、菜籽油和椰子油、脂肪酸酯、酮如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮、和醇如甲醇、环己醇、癸醇和四氢糠醇。
溶液包括乳油可以通过简单地混合各成分制备。粉尘剂和粉剂可通过混合和通常在如锤式粉碎机或流体动力磨中研磨来制备。悬浮剂通常通过湿磨法制备;见例如US3060084。颗粒剂和丸剂可通过将活性物质喷到预成型的颗粒载体上或造块法制备。见Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,第147-48页,Perry’s Chemical Engineer’s Handbook,第四版,McGraw-Hill,纽约,1963,第8-57页及其后内容,和PCT出版物WO91/13546。丸剂可如US4172714中所述制备。水分散性和水溶性粒剂可如US4144050、US3920442和DE3246493中教导的制备。片剂可如US5180587、US5232701和US5208030中教导的制备。膜剂如GB2095558和US3299566中教导的制备。
关于制剂领域的更多信息见T.S.Woods,“The Formulator’sToolbox-Product Forms for Modern Agriculture”in Pesticide Chemistryand Bioscience,The Food-Environment Challenge,T.Brooks and T.R.Roberts,Eds.,Proceedings of the 9th International Congress on PesticideChemistry,The Royal Society of Chemistry,剑桥,1999,第120-133页。还可见US3235361第6栏第16行至第7栏第19行和实施例10-41;US3309192第5栏第43行至第7栏第62行和实施例8、12、15、39、4l、52、53、58、132、138-140、162-164、166、167和169-182;US2891855第3栏第66行至第5栏第17行和实施例1-4;Klingman,Weed Controlas a Science,John Wiley and Sons,Inc.,纽约,1961,第81-96页;和Hance等人,Weed Control Handbook,第八版,Blackwell ScientificPublications,牛津,1989。
在下列实施例中,所有的百分数都是重量百分数,所有制剂都是以常规方式制备的。化合物编号指在索引表A中的化合物。
实施例A
可湿性粉剂
化合物1 65.0%
十二烷基苯酚聚乙二醇醚 2.0%
木质素磺酸钠 4.0%
硅铝酸钠 6.0%
蒙脱土(煅烧过的) 23.0%
实施例B
颗粒剂
化合物 110.0%
硅镁土颗粒(低挥发份,0.71/0.30mm;U.S.S.号25-50筛) 90.0%
实施例C
挤出丸剂
化合物1 25.0%
无水硫酸钠 10.0%
粗木质素磺酸钙 5.0%
烷基萘磺酸钠 1.0%
钙/镁膨润土 59.0%
实施例D
乳油
化合物1 20.0%
油溶性磺酸盐和聚氧乙烯醚的混合物 10.0%
异佛尔酮 70.0%
实施例E
颗粒剂
化合物1 0.5%
纤维素 2.5%
乳糖 4.0%
玉米粉 93.0%
本发明化合物的特征在于有利的代谢和/或土壤残留模式和显示出防治农业和非农业无脊椎害虫的活性。(在本公开内容范围内,“无脊椎害虫防治”意思是抑制无脊椎害虫发育(包括死亡率),从而使摄食或害虫造成的其他毁坏或损失显著降低;相关的表达有类似的定义)。本公开内容中提到的术语“无脊椎害虫”包括经济上重要的节肢动物、腹足动物和线虫害虫。术语“节肢动物”包括昆虫、螨、蜘蛛、蝎子、蜈蚣、倍足纲节动物、球潮虫和综合纲(symphylans)。术语“腹足动物”包括蜗牛、蛞蝓和其他柄眼目。术语“线虫”包括所有的蠕虫,如:蛔虫、犬心丝虫和植食性线虫(线虫纲)、吸虫(Tematoda)、棘头纲、和绦虫(绦虫纲)。本领域技术人员会认可不是所有的化合物对所有害虫都是同样有效的。本发明化合物显示对经济上重要的农业和非农业害虫有活性。术语“农学的”指大田作物如粮食和纤维的生产,并且包括谷类作物(例如小麦、燕麦、大麦、黑麦、稻和玉米)、豆类、蔬菜作物(例如莴苣、卷心菜、西红柿、菜豆)、马铃薯、甘薯、葡萄、棉花和乔性果树(例如仁果、核果和柑橘类水果)的栽培。术语“非农学的”指其他园艺的(例如未生长在大田的森林、温室、苗圃或观赏植物)、公共(人)和动物健康、家用和商用建筑、家庭、和储藏产品应用或害虫。因为无脊椎害虫防治谱和经济重要性,通过防治无脊椎害虫保护农业作物棉花、玉米、豆、稻、蔬菜作物、马铃薯、甘薯、葡萄和乔性果树(免于无脊椎害虫造成的伤害或毁坏)是本发明的优选实施方案。农业或非农业害虫包括鳞翅目幼虫,如夜蛾科的粘虫、地老虎、尺蠖和heliothines(例如秋夜蛾(Spodoptera fugiperda J.E.Smith),甜菜夜蛾(Spodoptera exigus Hübner),小地老虎(Agrotis ipsilon Hufnagel),粉纹夜蛾(Trichoplusia ni Hübner),美洲烟夜蛾(Heliothis virescensFabricius));螟蛾科的钻心虫、鞘蛾、结网毛虫、coneworms、卷心菜虫和雕叶虫(例如欧洲玉米螟(Ostrinia nubilalis Hübner),脐橙螟(Amyelois transitella Walker),玉米根草螟(Crambus caliginosellusClemens),苍螟(Herpetogramma licarsis Walker));卷蛾科的卷叶虫、食心虫、seed worms和fruit worms(例如苹果小卷蛾(Cydia pomonellaLinnaeus),葡萄小食心虫(Endopiza viteana Clemens),梨小食心虫(Grapholita molesta Busck));和许多其他经济上重要的鳞翅目(例如小菜蛾(Plutella xylostella Linnaeus),红铃麦蛾(Pectinophora gossypiellaSaunders),舞毒蛾日本亚种(Lymantria dispar Linnaeus));蜚蠊目的若虫和成虫,包括小蠊科和蜚蠊科的蟑螂(例如东方蜚蠊(Blatta orientalisLinnaeus),亚洲小蠊(Blatella asahinai Mizukubo),德国小蠊(Blattellagermanica Linnaeus),长须蜚蠊(Supella longipalpa Fabricius),美洲大蠊(Periplaneta americana Linnaeus),褐斑大蠊(Periplaneta brunneaBurmeister),马得拉蜚蠊(Leucophaea maderae Fabricius));鞘翅目的食叶幼虫和成虫,包括长角象科、豆象科和象虫科的象鼻虫(例如棉铃象(Anthonomus grandis Boheman),稻水象(Lissorhoptrus oryzophilusKuschel),谷象(Sitophilus grannarius Linnaeus),米象(Sitophilus oryzaeLinnaeus));叶甲科的跳甲、黄守瓜、食根虫、叶甲、potato beetles和潜叶虫(例如马铃薯叶甲(Leptinotarsa decemlineata Say),玉米根叶甲(Diabrotica virgifera virgifera LeConte));金龟子科的金龟子和其他甲虫(例如日本弧丽金龟(Popillia japomica Newman)和欧洲鳃角金龟(Rhizotrogus majalis Razoumowsky));皮蠹科的地毯圆皮蠹;叩甲科的叩甲;小蠹科的小蠹虫和拟步甲科的粉甲虫。此外农业和非农业害虫包括:革翅目的成虫和幼虫,包括球螋科的蠖螋(例如欧洲球螋(Forficula auricularia Linnaeus),椰实蠖螋(Chelisoches morioFabricius));半翅目和同翅目的成虫和若虫,如盲蝽科的盲蝽,蝉科的蝉,叶蝉科的叶蝉(例如小绿叶蝉属),蜡蝉总科和飞虱科的飞虱,角蝉科的角蝉,木虱科的木虱,粉虱科的粉虱,蚜科的蚜虫,根瘤蚜科的根瘤蚜,粉蚧科的粉蚧,蚧科、盾蚧科和珠蚧科的介壳虫,网蝽科的网蝽,蝽科的蝽象,长蝽科的长蝽(例如土长蝽属)和其他实蝽,沫蝉科的沫蝉,缘蝽科的南瓜缘蝽,和红蝽科的红蝽和棉蝽象。还包括螨目的成虫和幼虫,如叶螨科的蛛螨和红蜘蛛(例如苹果红蜘蛛(Panonychusulmi Koch),荨麻叶螨(Tetranychus urticae Koch),麦克旦尼氏叶螨(Tetranychus mcdanieli McGregor)),细须螨科的flat mites(例如桔短须螨(Brevipalpus lewisi McGregor)),瘿螨科的锈螨和芽螨及其他食叶螨和对人和动物健康重要的螨,即表皮螨科的尘螨,蠕形螨科的腺囊螨,甘螨科的谷螨,蜱目的蜱(例如鹿蜱(Ixodes scapularis Say),Australianparalysis tick(Ixodes holocyclus Neumann),美洲犬蜱(Dermacentorvariabilis Say),美洲花蜱(Amblyomma americanum Linnaeus)和瘁螨科、蒲螨和疥螨科的马瘁螨和疥螨;直翅目的成虫和未成熟个体,包括蚱蜢、蝗虫和蟋蟀(例如蚱蜢(例如迁飞黑蝗(Melanoplus sanguinipesFabricius),特异黑蝗(M.differentialis Thomas)),美洲蚱蜢(例如Schistocerca americana Drury),沙漠蝗(Schistocerca gregariaForskal),飞蝗(Locusta migratoria Linnaeus),家蟋蟀(Acheta domesticusLinnaeus),蝼蛄(Gryllotalpa属));双翅目的成虫和未成熟个体,包括潜叶虫、蠓、果蝇(实蝇科)、麦杆蝇(例如Oscinella frit Linnaeus),soilmaggots,家蝇(例如Musca domestica Linnaeus),小家蝇(例如Fanniacanicularis Linnaeus,F.femoralis Stein),厩螯蝇(例如Stomoxyscalcitrans Linnaeus),秋家蝇,角蝇,丽蝇(例如Chrysomya属,Phormia属),和其他蝇状害虫,牛虻(例如虻属),肤蝇(例如胃蝇属,狂蝇属),牛皮蝇(例如皮蝇属),鹿虻(例如斑虻属),羊蜱蝇(例如Melophagusovinus Linnaeus)和其他短角组,蚊子(例如伊蚊属,按蚊属,库蚊属),黑蝇(例如原蚋属,蚋属),蠓,白蛉和其他长角组;缨翅目的成虫和未成熟个体,包括棉蓟马(Thrips tabaci Lindeman)和其他食叶蓟马;膜翅目昆虫害虫,包括蚂蚁(例如锈色大黑蚁(Camponotus ferrugineusFabricius),黑木工蚁(Camponotus pennsylvanicus De Geer),厨蚁(Monomorium pharaonis Linnaeus),小火蚁(Wasmannia auropunctataRoger),火蚁(Solenopsis geminata Fabricius),外引红火蚁(Solenopsisinvicta Buren),阿根廷蚁(Iridomyrmex humilis Mayr),家褐蚁(Paratrechina longicornis Latreille),铺道蚁(Tetramorium caespitumLinnaeus),玉米田蚁(Lasius alienus F_rster),香家蚁(Tapinoma sessileSay),蜜蜂(包括木蜂),胡蜂,黄蜂;等翅目昆虫害虫,包括黄胸散白蚁(Reticulitermes flavipes Koller),西方犀白蚁(Reticulitermes hesperusBanks),台湾家白蚁(Coptotermes formosanus Shiraki),泛美楹白蚁(Incisitermes immigrans Snyder)和其他经济上重要的白蚁;缨尾目的虫害如西洋衣鱼(Lepisma saccharina Linnaeus)和家衣鱼(Thermobiadomestica Packard);食毛目的虫害,包括头虱(Pediculus humanuscapitis De Geer),体虱(Pediculus humanus humanus Linnaeus),鸡体虱(Menacanthus stramineus Nitszch),狗羽虱(Trichodectes canis DeGeer),鸡姬虱(Goniocotes gallinae De Geer),绵羊牛毛虱(Bovicola ovisSchrank),牛盲虱(Haematopinus eurysternus Nitzsch),长鼻牛虱(Linognathus vituli Linnaeus)和侵袭人和动物的其他吸吮和咀嚼寄生虱;Siphonoptera目虫害,包括东方鼠蚤(Xenopsylla cheopisRothschild),猫蚤(Ctenocephalides felis Bouche),狗蚤(Ctenocephalidescanis Curtis),鸡蚤(Ceratophyllus gallinae Schrank),禽毒蚤(Echidnophaga gallinacea Westwood),人蚤(Pulex irritans Linnaeus)和折磨哺乳动物和鸟类的其他蚤。其他节肢害虫包括:蜘蛛目的蜘蛛,如褐平甲蛛(Loxosceles reclusa Gertsch&Mulaik)和红斑蛛(Latrodecrus mactans Fabricius),和蛐延目的蜈蚣,如家蚰蜒(Scutigeracoleoptrata Linnaeus)。本发明化合物还对线虫纲、绦虫纲、吸虫纲和棘头纲的成员有活性,其中包括经济上重要的圆形目、粉螨目、尖尾目、小杆线虫目、旋尾目和刺嘴目的成员,如包括(但不限于)经济上重要的农业害虫(即根结属的根癌线虫,短体属的根斑线虫,毛刺属的黄麻根瘤线虫等)和动物及人健康害虫(即经济上重要的吸虫、绦虫和蛔虫,如马的普通圆形线虫(Strongylus vulgaris)、狗的犬弓首蛔虫(Toxocara canis)、绵羊的捻转血茅线虫(Haemonchus contortus)、狗的犬恶丝虫(Dirofilaria immitis Leidy)、马的叶状裸头绦虫(Anoplocephalaperfoliata)、反刍动物的肝片形吸虫(Fasciola hepatica)等)。
本发明化合物对下列害虫表现出特别高的活性:鳞翅目(例如Alabama argillacea Hübner(棉叶波纹夜蛾),Archips argyrospilaWalker(果树黄卷蛾),A.Rosana Linnaeus(玫瑰黄卷蛾)和其他黄卷蛾属品种,Chilo suppressalis Walker(二化螟),Cnaphalocrosis medinalisGuenee(稻纵卷叶野螟),Crambus caliginosellus Clemens(玉米根草螟),Crambus teterrellus Zincken(早熟禾草螟),Cydia pomonella Linnaeus(苹果皮小卷蛾),Earias insulana Boisduval(Spiny bollworm),Earias vittellaFabricius(棉斑实蛾),Helicoverpa armigera Hübner(棉铃虫),Helicoverpa zea Boddie(谷实夜蛾),Heliothis virescens Fabricius(烟芽夜蛾),Herpetogramma licarsisalis Walker(苍螟),Lobesis botrana Denis&Schiffermüller(葡萄小食心虫),Pectinophora gossypiella Saunders(红铃麦蛾),Phyllocnistis citrella Stainton(柑橘叶潜蛾),Pieris brassicaeLinnaeus(欧洲粉螟),Pieris rapae Linnaeus(菜粉蝶),Plutella xylostellaLinnaeus(小菜蛾),Spodoptera exigus Hübner(贪夜蛾),Spodoptera lituraFabricius(斜纹贪夜蛾),Spodoptera frugiperda J.E.Smith(秋夜蛾),Trichoplusia ni Hübner(甘蓝粉纹夜蛾)和Tuta absoluta Meyrick(tomatoleafminer))。本发明化合物还对同翅目的害虫有商业上显著的活性,其中包括:Acythisiphon pisum Harris(豌豆蚜),Aphis craccivora Koch(豆蚜),Aphis fabae Scopoli(豆卫矛蚜),Aphis gossypti Glover(棉蚜),Aphispomi De Geer(苹果蚜),Aphis spiraecola Patch(异绣线菊蚜),Aulacorthum solani Kaltenbach(土豆沟无网蚜),Chaetosiphonfragaefolii Cockerell(草莓钉蚜),Diuraphis noxiaKurdjumov/Mordvilko(Russian wheat aphid),Dysaphis plantagineaPaaserini(车前西圆尾蚜),Eriosoma lanigerum Hausmann(苹果绵蚜),Hyalopterus pruni Geoffroy(梅大尾蚜),Lipaphis erysimi Kaltenbach(萝卜蚜),Metopolophium dirrhodum Walker(麦无网蚜),Macrosipumeuphorbiae Thomas(马铃薯长管蚜),Myzus persicae Sulzer(桃蚜),Nasonovia ribisnigri Mosley(莴苣衲长管蚜),瘿绵蚜属(根蚜和瘿蚜),Rhopalosiphum maidis Fitch(玉米缢管蚜),Rhopalosiphum padiLinnaeus(禾谷缢管蚜),Schizaphis graminum Rondani(麦二叉蚜),Sitobion avenae Fabricius(麦长管蚜),Therioaphis maculata Buckton(苜蓿斑翅蚜),Toxoptera aurantti Boyer de Fonscolombe(橘声蚜),和Toxoptera citricida Kirkaldy(褐橘声蚜);球蚜属;Phyllobxera devastatrixPergande(美洲山核桃根瘤蚜);Bemisia tabaci Gennadius(甘薯粉虱),Bemisia argentifolii Bellows & Perring(银叶粉虱),Dialeurodes citriAshmead(柑橘粉虱)和Trialeurodes vaporariorum Westwood(温室粉虱);Empoasca fabae Harris(马铃薯叶蝉),Laodelphax striatellusFallen(灰飞虱),Macrolestes quadrilineatus Forbes(紫莞叶蝉),Nephotettix cunticeps Uhler(黑尾叶蝉),Nephotettix nigropictus St_l(二条黑尾叶蝉),Nilaparvata lugens St_l(褐飞虱),Peregrinus maidisAshmead(玉米花翅飞虱),Sogatella furcifera Horvath(白背飞虱),Sogatodes orizicola Muir(美洲稻飞虱),Typhlocyba pomaria McAtee(苹白小叶蝉),Erythroneoura属(葡萄二星斑叶蝉);Magicidadaseptendecim Linnaeus(晚秀蝉);Icerya purchasi Maskell(澳洲吹绵蚧),Quadraspidiotus perniciosus Comstock(梨笠圆盾蚧);Planococcus citriRisso(橘臀纹粉蚧);粉蚧属(其他粉蚧复合体);Caeopsylla pyricolaFoerster(梨黄木虱),Trioza diospyri Ashmead(柿个木虱)。这些化合物还对半翅目害虫有活性,其中包括:Acrosternum hilare Say(喜绿蝽),Anasa tristis De Geer(南瓜缘蝽),Blissus leucopterus Leucopterus Say(麦长蝽),Corythuca gossypii Fabricius(棉网蝽),Cyrtopeltis modestaDistant(tomato bug),Dysdercu suturellus Herrich-Sch_ffer(棉蝽象),Euchistus servus Say(褐臭蝽),Euchistus variolarius Palisot deBeauvois(一点褐蝽),红腺长蝽属(实蝽复合体),Leptoglossus corculusSay(松籽喙缘蝽),Lygus lineolaris Palisot de beauvois(美国牧草长蝽),Nezara viridula Linnaeus(稻绿蝽),Oebalus pugnax Fabricius(美洲稻缘蝽),Oncopeltus fasciatus Dallas(大马利筋长蝽),Pseudatomoscelisseriatus Reuter(棉跳盲蝽)。本发明化合物可防治的其他昆虫目包括缨翅目(例如Frankliniella occidentalis Pergande(西花蓟马),Scirthothripscitri Moulton(橘硬蓟马),Sericothrips variabilis Beach(大豆蓟马)和Thrips tabaci Lindeman(烟蓟马);和鞘翅目(例如Leptinotarsadecemlineata Say(马铃薯叶甲),Epilachna varivestis Mulsant(墨西哥豆瓢虫)和叩头虫、Athous或Limonius属的wireworms)。
本发明化合物还可与一种或多种其他生物活性化合物或试剂混合形成多成分农药,得到更广谱的农业应用,所述其他生物活性化合物或试剂包括杀虫剂、杀真菌剂、杀线虫剂、杀细菌剂、杀螨剂、生长调节剂如促根剂、化学绝育剂、化学信息素、驱避剂、引诱剂、外激素、取食刺激剂、其他生物活性化合物或昆虫致病性细菌、病毒或真菌。因此,本发明组合物还可含生物有效量的至少一种额外的生物活性化合物或试剂。本发明化合物可与其配制成制剂的所述生物活性化合物或试剂的实例是:杀虫剂如阿维菌素(abamectin),乙酰甲胺磷,啶虫脒,阿维菌素(avermectin),艾扎丁,保棉磷,联苯菊酯,联苯肼酯,噻嗪酮,克百威,氟唑虫清,氟啶脲,毒死蜱,甲基毒死蜱,chromafenozide,噻虫胺,氟氯氰菊酯,高效氟氯氰菊酯,氯氟氰菊酯,高效氯氟氰菊酯,氯氰菊酯,灭蝇胺,溴氰菊酯,丁醚脲,二嗪磷,除虫脲,乐果,_茂醚,阿维菌素(emamectin),硫丹,S-氰戊菊酯,ethiprole,苯硫威,苯氧威,甲氰菊酯,唑螨酯,氰戊菊酯,氟虫腈,flonicamid,氟氰戊菊酯,氟胺氰菊酯,氟虫脲,地虫硫磷,特丁苯酰肼,氟铃脲,吡虫啉,_二唑虫,异柳磷,虱螨脲,马拉硫磷,四聚乙醛,甲胺磷,杀扑磷,灭多威,烯虫酯,甲氧滴滴涕,久效磷,甲氧苯酰肼,硝虫噻嗪,双苯氟脲,杀线威,对硫磷,甲基对硫磷,氯菊酯,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,抗蚜威,丙溴磷,吡蚜酮,pyridalyl,吡丙醚,鱼藤酮,艾克敌105,硫丙磷,虫酰肼,氟苯脲,七氟菊酯,特丁硫磷,杀虫畏,噻虫啉,阿克泰,硫双威,杀虫双,四溴菊酯,敌百虫和杀铃脲;杀真菌剂如噻二唑素,腈嘧菌酯,苯菌灵,灭瘟素,波尔多液(碱式硫酸铜),糠菌唑,氯环丙酰胺,敌菌丹,克菌丹,多菌灵,地茂散,百菌清,王铜,铜盐,cyflufenamid,霜脲氰,环丙唑醇,嘧菌环胺,(S)-3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺(RH7281),diclocymet(S-2900),哒菌酮,氯硝胺,苯醚甲环唑,(S)-3,5-二氢-5-甲基-2-(甲硫基)-5-苯基-3-(苯基氨基)-4H-咪唑-4-酮(RP407213),烯酰吗啉,dimoxystrobin,烯唑醇,甲基烯唑醇,多果定,敌瘟磷,氧唑菌,_唑酮菌,咪唑菌酮,氯苯嘧啶醇,腈苯唑,fencaramid(SZX0722),拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,氟啶胺,咯菌腈,flumetover(RPA403397),氟喹唑,氟硅唑,氟酰胺,粉唑醇,灭菌丹,三乙膦酸铝,呋霜灵,furametapyr(S-82658),己唑醇,种菌唑,异稻瘟净,异菌脲,稻瘟灵,春雷霉素,亚胺菌,代森锰锌,代森锰,mefenoxam,灭锈胺,甲霜灵,叶菌唑,叉胺苯酰胺/苯氧菌胺(SSF-126),腈菌唑,甲胂铁铵(甲烷胂酸铁),恶霜灵,戊菌唑,戊菌隆,烯丙苯噻唑,咪鲜胺,霜霉威,丙环唑,啶斑肟,唑菌胺酯,嘧霉胺,咯喹酮,喹氧灵,螺_茂胺,硫,戊唑醇,四氟醚唑,噻菌灵,溴氟唑菌,甲基硫菌灵,福美双,tiadinil,三唑酮,三唑醇,三环唑,trifloxystrobin,灭菌唑,有效霉素和乙烯菌核利;杀线虫剂如涕灭威,杀线威和苯线磷;杀细菌剂如链霉素;杀螨剂如双甲脒,灭满猛,乙酯杀螨醇,三环锡,三氯杀螨醇,除螨灵,特苯_唑,喹螨醚,苯丁锡,甲氰菊酯,唑螨酯,噻螨酮,炔螨特,哒螨灵和吡螨胺;和生物制剂如苏云金芽孢杆菌,包括aizawai和kurstaki亚种,苏云金杆菌δ内毒素,杆状病毒,和昆虫致病性细菌、病毒和真菌。本发明化合物及其组合物可施用于被遗传转化成能表达无脊椎害虫毒性蛋白(如苏云金芽孢杆菌毒素)的植物。本发明无脊椎害虫防治化合物外部施用的影响可以与所表达的毒素蛋白质协同作用。
关于这些农业保护剂一般可参考是The Pesticide Manual,第12版,C.D.S.Tomlin编,Brithsih Crop Protection Council,Farnham,Surrrey,U.K.,2000。
优选与本发明化合物混合的杀虫剂和杀螨剂包括拟除虫菊酯如氟氰菊酯,氯氟氰菊酯,氟氯氰菊酯,高效氟氯氰菊酯,S-氰戊菊酯,fenvalerate和四溴菊酯;氨基甲酸酯类如苯硫威,灭多威,杀线威和硫双威;新烟碱类似物如噻虫胺,吡虫啉和噻虫啉;神经元钠通道阻断剂如_二唑虫;杀虫大环内酯如艾克敌105,abamectin,avermectin和emamectin;γ-氨基丁酸(GABA)拮抗剂如硫丹,ethiprole和氟虫腈;杀虫脲类如氟虫脲和杀铃脲;保幼激素仿造物如苯虫醚和吡丙醚;吡蚜酮;和双甲脒。优选与本发明化合物混合的生物制剂包括素云集芽孢杆菌和苏云金芽孢杆菌δ内毒素以及天然存在的和遗传改性的病毒杀虫剂,其中包括杆状病毒科的成员,以及昆虫致病性真菌。
最优选的混合物包括本发明化合物与氯氟氰菊酯的混合物;本发明化合物与高效氟氯氰菊酯的混合物;本发明化合物与S-氰戊菊酯的混合物;本发明化合物与灭多威的混合物;本发明化合物与吡虫啉的混合物;本发明化合物与噻虫啉的混合物;本发明化合物与_二唑虫的混合物;本发明化合物与阿维菌素(abamectin)的混合物;本发明化合物与硫丹的混合物;本发明化合物与ethiprole的混合物;本发明化合物与氟虫腈的混合物;本发明化合物与氟虫脲的混合物;本发明化合物与吡丙醚的混合物;本发明化合物与吡蚜酮的混合物;本发明化合物与双甲脒的混合物;本发明化合物与苏云金芽孢杆菌的混合物和本发明化合物与苏云金芽孢杆菌δ内毒素的混合物。
在一些情况下,与具有相似的防治谱但不同的作用模式的其他无脊椎害虫防治化合物或试剂组合对于抗药性处理是特别有利的。因此,本发明组合物可以还含有生物有效量的至少一种具有相似的防治谱但不同的作用模式的另外的无脊椎害虫防治化合物或试剂。用生物有效量的本发明化合物接触遗传改性成表达植物保护化合物(例如蛋白质)的植物或植物所在地也能提供更广谱的植物保护并且对于抗药性处理是有利的。
在农业和非农业应用中防治无脊椎害虫是通过将本发明的一种或多种化合物以有效量施用到害虫的环境中,其中包括感染的农业和/或非农业位点、需保护的区域,或直接施用于需防治的害虫上。因此,本发明还包括防治在农业和/或非农业应用中的无脊椎害虫的方法,包括用生物有效量的本发明一种或多种化合物,或用含至少一种上述化合物的组合物或含至少一种上述化合物和有效量的至少一种另外的生物活性化合物或试剂的组合物接触无脊椎害虫或其环境。适宜的含本发明化合物和有效量的至少一种另外的生物活性化合物或试剂的组合物的实例包括其中另外的生物活性化合物或试剂与本发明化合物存在于同一颗粒上或存在于与本发明化合物分离的颗粒上的组合物。
优选的接触方法是通过喷雾。作为可替代方式,含本发明化合物的颗粒组合物可被施用于植物叶片或土壤。
本发明的化合物也可通过用含本发明化合物的组合物接触植物被植物吸收而有效输送,所述组合物以土壤浇灌液体制剂、颗粒制剂施用到土壤、育苗箱处理或移植体浸渍的方式施用。化合物通过将含本发明化合物的组合物局部施用到感染位点也是有效的。其他接触方法包括通过直接和滞留喷雾、飞机喷雾、凝胶、拌种、微胶囊化、内吸、饵、耳标、丸剂、烟雾发生器、烟熏剂、气雾剂、粉尘剂等施用本发明的化合物或组合物。还可将本发明化合物渗透到用于制造无脊椎动物防治装置(例如捕虫网)的材料中。
本发明的化合物可掺入被无脊椎动物食用的饵中或装置如捕捉阱等中。含0.01-5%活性成分、0.05-10%保水剂和40-99%植物粉的颗粒或饵在极低的用量下,特别是在活性成分经摄食而非直接接触致死剂量下能有效防治土壤昆虫。
本发明化合物可以其纯物质状态施用,但最经常施用的是含一种或多种化合物和适宜的载体、稀释剂和表面活性剂,以及根据预期的最终用途可能结合食物的制剂。优选的施用方法包括喷雾本发明化合物的水分散体或精炼油溶液。结合喷雾油、喷雾浓缩油、粘展剂、助剂、其他溶剂和增效剂如增效醚往往能增强化合物效力。
有效防治所需用量(即“生物有效量”)取决于下述因素如需防治的无脊椎动物的种类、害虫的生活周期、虫态、其大小、位置、年中时间、作物或动物寄主、摄食行为、交配行为、环境湿度、温度等。在正常环境下,大约0.01-2kg活性成分/公顷的用量就足以防治农业生态系统中的害虫,但低至0.0001kg/公顷可能就足以或也可能需要多达8kg/公顷。对于非农业应用来说,有效用量可能从大约1.0到50mg/平方米变动,但低至0.1mg/平方米可能就足够或也可能需要多达150mg/平方米。本领域技术人员能容易地确定达到预期的无脊椎害虫防治水平必需的生物有效量。
下列实验证明了本发明化合物对特定害虫的防治效力。“防治效力”代表抑制节肢动物发育(包括死亡),致使摄食显著降低。然而,本发明化合物提供的害虫防治保护并不限于这些品种。见化合物说明索引表A-C。下列缩写用于下面的索引表中:t是叔,i是异,Me是甲基,Et是乙基,Pr是丙基,i-Pr是异丙基,Bu是丁基。缩写“Ex.”代表“实施例”,之后的数字表示该化合物是在哪个实施例中制备的。
索引表A
化合物 | R3 | R4 | R5(a) | R5(b) | (R6)q | 1H NMR |
1(Ex.1) | i-Pr | Me | H | CF3 | 2-Cl | * |
2(Ex.2) | i-Pr | Me | H | CO2Me | 2-Cl | * |
3 | i-Pr | Me | H | CO2Me | 2-Me | * |
4 | i-Pr | Me | H | CF3 | 2-Me | * |
5 | i-Pr | Me | H | CF3 | 2-F | * |
6 | t-Bu | Me | H | CF3 | 2-Me | * |
7 | i-Pr | Me | Me | CF3 | 2-Cl | * |
8 | i-Pr | Me | H | CF3 | 2,6-F2 | * |
*H1NMR数据见索引表C
索引表B
化合物 | R3 | R4 | R5 | R6 | 1H NMR |
B1(Ex.3) | i-Pr | Me | CF3 | 2-Cl | * |
*H1NMR数据见索引表C
索引表C
化合物编号 | 1H NMR数据(除非另有说明为CDCl3溶液)a |
12345678B1 | 9.4(bs,1H),7.6-7.5(d,1H),7.4-7.1(m,6H),5.8(bd,1H),5.4(dd,1H),4.3-4.1(m,1H),3.6-3.4(m,2H),1.84(s,3H),1.3-1.2(m,6H).9.4-9.3(bs,1H),7.6(d,1H),7.4-7.3(d,1H),7.3-7.0(m,5H),5.8(d,1H),5.5(dd,1H),4.2-4.1(m,1H),3.89(s,3H),3.7-3.4(m,2H),1.81(s,3H),1.3-1.2(m,6H).两个异构体:9.5+9.3-9.2(2xbs,1H),7.3-7.0(m,7H),5.8(bm,1H),5.1-5.0(m,1H),4.1-4.0(m,1H),3.87(s,3H),3.7-3.5(m,1H),3.5-3.3(m,1H),2.5(2xs,3H),2.0-1.9+1.87(2xs,3H),1.3-1.1(m,6H).(DMSO-d6)9.81(s,1H),8.1-8.0(m,1H),7.3-6.9(m,7H),5.3(m,1H),4.0-3.9(m,1H),3.6(m,1H),1.79(s,3H),1.1(m,6H).(DMSO-d6)9.85(s,1H),8.1-8.0(d,1H),7.4-6.9(m,7H),5.5-5.4(m,1H),4.0-3.9(m,1H),3.7(m,1H),3.5-3.3(m,1H),2.07(s,3H),1.11(d,3H),1.06(d,3H).(DMSO-d6)9.3-9.2(s,1H),7.4-7.0(m,7H),5.8(d,1H),5.1-5.0(m,1H),3.6-3.3(m,2H),1.88(s,3H),1.40(s,9H).10.0-9.9(s,1H),7.5-7.1(m,7H),5.9(d,1H),4.2-4.1(m,1H),3.7(d,1H),3.3-3.2(d,1H),2.27(s,3H),1.50(s,3H),1.3-1.2(m,6H).9.3(s,1H),7.3-7.2(m,3H),7.0(m,3H),5.8(d,1H),5.0-4.9(dd,1H),4.1(m,1H),3.7-3.4(Abd,2H),2.10(s,3H),1.3-1.1(m,6H).9.6(s,1H),7.6-7.1(m,7H),5.9-5.8(d,1H),5.0-4.9(dd,1H),4.8-4.7(m,1H),4.3(dd,1H),4.2-4.1(m,1H),2.10(s,3H),1.3-1.2(m,6H). |
a H1NMR数据是距四甲基硅烷的低磁场ppm。连接符号特指(s)-单峰,(d)-双重峰,(t)-三重峰,(q)-四重峰,(m)-多重峰,(dd)-双重峰的双峰,(dt)-三重峰的双峰,(br s)-宽单峰。
本发明的生物实施例
试验A
用由内装12-14-天-龄萝卜的小型敞开式容器构成的试验装置评价对菜蛾(Plutella xylostella)的防治。预先用有10-15只新生幼虫的一块昆虫食物进行感染,使用取样器从有许多幼虫生长的一片硬化的昆虫食物上取出一块,并将含幼虫和食物的块转移到试验装置中。当食物块变干,幼虫移动到试验植物上。
除非另外指出,用含10%丙酮、90%水的溶液和含烷芳基聚氧乙烯、游离脂肪酸、二元醇和异丙醇的300ppm X-77_Spreader Lo-FoamFormula非离子表面活性剂(Loveland Industries,Inc.)将试验化合物配成制剂。通过每个试验装置上方1.27cm(0.5英寸)处安置的具1/8JJ定制机身的SUJ2雾化喷嘴(Spraying Systems Co.)喷施1ml化合物液体制剂。在这些试验中的所有实验化合物以250ppm(或更低)浓度喷洒并且重复三次。喷洒完配制后的试验化合物后,令每个试验装置干燥1小时,然后在顶部盖一个黑色有滤网的罩。将试验装置在25℃、70%相对湿度的生长室内放6天。然后根据被吃掉的叶片目测评价植物摄食损失。
在试验化合物中,下列化合物提供了极高水平的植物保护(0-1、10%或更低的摄食损失等级):1*、3、4*、5*、6*、7*、8**。
试验B
用由内装4-5-天-龄玉米的小型敞开式容器构成的试验装置评价对秋夜蛾(Spodoptera frugiperda)的防治。预先用有10-15只1-天-龄幼虫的一块昆虫食物进行感染(使用取样器)。
将试验化合物配成制剂并如试验A所述以250ppm(或更低)浓度喷洒。所有施用重复三次。喷洒后,令试验装置保持在生长室中,然后根据如试验A所述目测评价植物摄食损失等级。
在试验化合物中,下列化合物提供了极高水平的植物保护(10%或更低的摄食损失):1*、4**、5*。
试验C
用由内装6-7-天龄棉花的小型敞开式容器构成的试验装置评价对美洲烟夜蛾(Heliothis virescens)的防治。预先用有8只2-天-龄幼虫的一块昆虫食物进行感染(使用取样器)。
将试验化合物配成制剂并如试验A所述以250ppm(或更低)浓度喷洒。所有施用重复三次。喷洒后,令试验装置保持在生长室中,然后根据如试验A所述目测评价植物摄食损失等级。
在试验化合物中,下列化合物提供了极高水平的植物保护(20%或更低的摄食损失):1*、4**、5*、6*。
试验D
用由内装4-5-天-龄玉米的小型敞开式容器构成的试验装置评价对甜菜夜蛾(Spodoptera exigua)的防治。预先用有10-15只1-天-龄幼虫的一块昆虫食物进行感染(使用取样器)。
将试验化合物配成制剂并如试验A所述以250ppm(或更低)浓度喷洒。所有施用重复三次。喷洒后,令试验装置保持在生长室中,然后根据如试验A所述目测评价植物摄食损失等级。
在试验化合物中,下列化合物提供了极高水平的植物保护(20%或更低的摄食损失):1*、4*、5*、6*。
*试验在50ppm浓度下进行,**试验在10ppm浓度下进行。
Claims (9)
3.权利要求2所述化合物,其中V是N。
4.权利要求2所述化合物,其中V是CH、CF、CCl或CBr。
5.权利要求1所述化合物,其选自下组:
1-(2-氯苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-三氟甲基)-1H-吡唑-5-甲酰胺,
1-(2-氯苯基)-4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]1H-吡唑-3-羧酸甲酯,
4,5-二氢-5-[[[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]氨基]羰基]-1-(2-甲基苯基)-1H-吡唑-3-羧酸甲酯,
4,5-二氢-N-[2-甲基-6[[(1-甲基乙基)氨基]羰基]苯基]-1-(2-甲基苯基)-3-(三氟甲基)-1H-吡唑-5-甲酰胺,
1-(2-氟苯基)-4,5-二氢-N-[2-甲基-6-[[(1-甲基乙基)氨基]羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺,
N-[2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-4,5-二氢-1-(2-甲基苯基)-3-(三氟甲基)-1H-吡唑-5-甲酰胺,和
1-(2,6-二氟苯基)-4,5-二氢-N-[2-甲基-6-[[1-甲基乙基])氨基]羰基]苯基]-3-(三氟甲基)-1H-吡唑-5-甲酰胺。
6.一种防治无脊椎害虫的方法,包括用生物有效量的权利要求1所述化合物接触无脊椎害虫或其环境。
7.权利要求6所述方法,还包含用于防治无脊椎害虫的生物有效量的至少一种另外的化合物或试剂。
8.一种防治无脊椎害虫的组合物,含生物有效量的权利要求1所述化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的附加成分。
9.权利要求8所述组合物,还含有有效量的至少一种另外的生物活性化合物或试剂。
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DE102004035134A1 (de) | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern |
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