CN101443313A - 喹啉衍生物及其作为农药的用途 - Google Patents
喹啉衍生物及其作为农药的用途 Download PDFInfo
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- CN101443313A CN101443313A CNA2007800174213A CN200780017421A CN101443313A CN 101443313 A CN101443313 A CN 101443313A CN A2007800174213 A CNA2007800174213 A CN A2007800174213A CN 200780017421 A CN200780017421 A CN 200780017421A CN 101443313 A CN101443313 A CN 101443313A
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- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract description 5
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title abstract 2
- 239000000575 pesticide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 303
- -1 hydroxy, cyano, amino Chemical group 0.000 claims abstract description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000000543 intermediate Substances 0.000 claims abstract description 32
- 241000238631 Hexapoda Species 0.000 claims abstract description 31
- 241000244206 Nematoda Species 0.000 claims abstract description 29
- 241001465754 Metazoa Species 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims abstract description 6
- 244000045947 parasite Species 0.000 claims abstract description 6
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 5
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 5
- 206010061217 Infestation Diseases 0.000 claims abstract description 4
- 208000015181 infectious disease Diseases 0.000 claims abstract description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 63
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 239000000460 chlorine Substances 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002689 soil Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 238000009395 breeding Methods 0.000 claims description 9
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- 230000000590 parasiticidal effect Effects 0.000 claims description 9
- 239000002297 parasiticide Substances 0.000 claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 239000000556 agonist Substances 0.000 claims description 6
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004327 boric acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 239000003467 chloride channel stimulating agent Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 230000010627 oxidative phosphorylation Effects 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- VSVKOUBCDZYAQY-UHFFFAOYSA-N 7-chloro-1,2-benzothiazole Chemical compound ClC1=CC=CC2=C1SN=C2 VSVKOUBCDZYAQY-UHFFFAOYSA-N 0.000 claims description 3
- 239000005653 Bifenazate Substances 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000005926 Pyridalyl Substances 0.000 claims description 3
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 claims description 3
- FOANIXZHAMJWOI-UHFFFAOYSA-N bromopropylate Chemical compound C=1C=C(Br)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Br)C=C1 FOANIXZHAMJWOI-UHFFFAOYSA-N 0.000 claims description 3
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 claims description 3
- 150000007857 hydrazones Chemical class 0.000 claims description 3
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims description 3
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 claims description 3
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 claims description 3
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012747 synergistic agent Substances 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- QHGUCRYDKWKLMG-QMMMGPOBSA-N (R)-octopamine Chemical compound NC[C@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-QMMMGPOBSA-N 0.000 claims description 2
- 239000005952 Aluminium phosphide Substances 0.000 claims description 2
- 229920002101 Chitin Polymers 0.000 claims description 2
- 229940118183 Chloride channel agonist Drugs 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 2
- QHGUCRYDKWKLMG-MRVPVSSYSA-N Octopamine Natural products NC[C@@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-MRVPVSSYSA-N 0.000 claims description 2
- PPNXXZIBFHTHDM-UHFFFAOYSA-N aluminium phosphide Chemical compound P#[Al] PPNXXZIBFHTHDM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
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- VCYZVXRKYPKDQB-UHFFFAOYSA-N ethyl 2-fluoroacetate Chemical compound CCOC(=O)CF VCYZVXRKYPKDQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
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- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 2
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- 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 claims description 2
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- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229940080817 rotenone Drugs 0.000 description 1
- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- JJSYXNQGLHBRRK-YSOSZROBSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-YSOSZROBSA-N 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000002453 shampoo Substances 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 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
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- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
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- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及式(I)的喹啉衍生物:R1、R2、R3各自独立地为卤素、羟基、氰基、氨基、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C4烷氧基-C1-C4烷氧基、C3-C7环烷基-C1-C4烷氧基、C(OH)(CF3)2、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C(Ra)=O、C(Ra)=NORb、C(=O)ORx或C(=O)NRxRy;Ra为氢或C1-C4烷基;Rb为氢、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C1-C4卤代烷基或C2-C4卤代链烯基;Rx、Ry各自独立地为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷基-S(=O)C1-C4烷基、C1-C4烷基-S(=O) 2C1-C4烷基、C3-C6环烷基、C1-C4烷基-C3-C6环烷基、C3-C6链烯基、C3-C6炔基;R4、R5、R6、R7各自独立地为氢、卤素、氰基、氨基、硝基、羟基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(=O)ORc;Rc为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基;m和n各自独立地为1、2、3、4或5;p为0、1、2、3、4或5;及其N-氧化物、对映异构体、非对映异构体和盐,本发明涉及制备化合物I的方法和中间体,和化合物(I)在防治昆虫、螨虫或线虫中的用途,一种通过使用化合物(I)而治疗、防治、预防或保护动物免受寄生虫侵染或感染的方 法。
Description
本发明涉及式I的喹啉衍生物:
R1、R2、R3各自独立地为卤素、羟基、氰基、氨基、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C4烷氧基-C1-C4烷氧基、C3-C7环烷基-C1-C4烷氧基、C(OH)(CF3)2、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C(Ra)=O、C(Ra)=NORb、C(=O)ORx或C(=O)NRxRy;
Ra为氢或C1-C4烷基;
Rb为氢、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C1-C4卤代烷基或C2-C4卤代链烯基;
Rx、Ry各自独立地为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷基-S(=O)C1-C4烷基、C1-C4烷基-S(=O)2C1-C4烷基、C3-C6环烷基、C1-C4烷基-C3-C6环烷基、C3-C6链烯基、C3-C6炔基;
R4、R5、R6、R7各自独立地为氢、卤素、氰基、氨基、硝基、羟基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(=O)ORc;
Rc为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基;
m和n各自独立地为1、2、3、4或5;
p为0、1、2、3、4或5;
及其N-氧化物、对映异构体、非对映异构体和盐。
另外,本发明涉及制备化合物I的方法,包含化合物I的杀虫组合物和通过使昆虫、螨虫或线虫或其食物供应源、栖息地或繁殖地与杀虫有效量的式I的化合物或其组合物接触而防治昆虫、螨虫或线虫的方法。
此外,本发明还涉及一种通过将杀虫有效量的式I化合物或其组合物施用于植物,或昆虫、螨虫或线虫在其中生长的土壤或水来保护生长中的植物免受昆虫、螨虫或线虫侵袭或侵染的方法。
本发明还提供一种治疗、防治、预防或保护动物免受寄生虫侵染或感染的方法,其包括向动物经口服、局部或肠胃外给药或施用杀寄生虫有效量的式I化合物或其组合物。
尽管目前可得到市售杀虫剂和杀螨剂,但由害虫引起的对生长中与已收获的作物的危害仍存在。因此,仍持续需要开发新的且更有效的杀虫剂。
因此本发明的目的为提供用于防治昆虫、螨虫或线虫且保护生长中的植物免受昆虫、螨虫和线虫侵袭或侵染的新杀虫组合物、新化合物和新方法。
我们发现这些目的由式I化合物或其组合物来实现。此外,我们发现了制备式I化合物的方法。
在WO 05/33081中描述了杀真菌性喹啉亚甲基氨基磺酰胺。未具体提及在磺酰胺基团上带有联苯基结构部分的喹啉亚甲基氨基磺酰胺。在申请中的申请US 60/662411尤其描述在磺酰胺基团上带有联苯基结构部分的特定杀虫性喹啉亚甲基氨基磺酰胺,其中该联苯基结构部分可在4位(如上编号)上被取代。未具体公开其中联苯基团带有超过1个取代基的化合物。
通常而言,式(I)的喹啉衍生物可由中间体(II)与代硼酸(boronicacid)(III)通过Suzuki偶联反应而获得,其中这些化合物中的变量具有如上文对式(I)的喹啉衍生物所定义的含义且L为离去基团:
例如在以下文献中所描述,该反应通常在20-180℃,优选40-120℃的温度下,在惰性有机溶剂中,在碱和催化剂,尤其是钯催化剂存在下进行:Synth.Commun.第11卷,第513页(1981);Acc.Chem.Res.第15卷,第178-184页,(1982);Chem.Rev.第95卷,第2457-2483页,(1995);OrganicLetters,第6卷(16),第2808页,(2004);"Metal catalyzed cross couplingreactions",第2版,Wiley,VCH 2005(De Meijere,Diederich编辑);"Handbook of organop alladium chemistry for organic synthesis"(Negishi编辑),Wiley,Interscience,New York,2002;"Handbook of functionalizedorganometallics",(P.Knochel编辑),Wiley,VCH,2005。
在化合物(II)中的合适的离去基团L为卤素,优选为氯、溴或碘;烷基羧酸根,苯甲酸根,烷基磺酸根,卤代烷基磺酸根或芳基磺酸根;最优选为氯。
合适的代硼酸为其中变量Ri和Rj具有氢或C1-C4烷基的含义,或Ri和Rj一起形成其碳原子可全部或部分被甲基取代的亚乙基或亚丙基桥的那些。
合适的催化剂为四(三苯基膦)钯(0);双(三苯基膦)氯化钯(II);双(乙腈)氯化钯(II);[1,1'-双(二苯基膦基)二茂铁]-氯化钯(II)配合物;双[双-(1,2-二苯基膦基)乙烷]钯(O);双(双-(1,2-二苯基膦基)丁烷]-氯化钯(II);乙酸钯(II);氯化钯(II);和乙酸钯(II)/三-邻甲苯基膦配合物或膦与Pd盐的混合物或膦与Pd的配合物,例如二亚苄基丙酮-钯与三叔丁基膦(或其四氟硼酸盐)、三环己基膦;或结合聚合物的Pd-三苯基膦催化剂体系。
合适的溶剂为脂族烃,例如戊烷、己烷、环己烷和石油醚;芳族烃,例如甲苯、邻二甲苯、间二甲苯和对二甲苯;醚,例如二异丙基醚、叔丁基甲醚、二噁烷、苯甲醚和四氢呋喃和二甲氧基乙烷;酮,例如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮;以及乙腈、二甲亚砜、二甲基甲酰胺和二甲基乙酰胺;尤其优选醚,例如四氢呋喃、二噁烷和二甲氧基乙烷。也可使用所提及溶剂的混合物或与水的混合物。
合适的碱通常为无机化合物,例如碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钙和氧化镁;碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾、碳酸铯和碳酸钙;以及碱金属碳酸氢盐,例如碳酸氢钠;碱金属醇盐和碱土金属醇盐,例如甲醇钠、乙醇钠、乙醇钾和叔丁醇钾;还有有机碱,例如叔胺,例如三甲胺、三乙胺、三异丙基乙胺和N-甲基哌啶、吡啶、被取代的吡啶(例如可力丁、卢剔啶和4-二甲基氨基吡啶),以及双环胺。尤其优选诸如碳酸钠、碳酸钾、碳酸铯、三乙胺和碳酸氢钠的碱。
该碱相对于1摩尔化合物(II)以1:1-1:10,优选1:1.5-1:5的摩尔比使用,代硼酸相对于1摩尔化合物(II)以1:1-1:5,优选1:1-1:2.5的摩尔比使用。在某些情况下,以相对于1摩尔化合物(II)为0.7:1-0.99:1的亚化学计量的量使用代硼酸对于易于纯化而言可能是有利的。
反应完成后,可通过使用例如将反应混合物加入水中,用有机溶剂萃取,浓缩萃取物等常规方法来分离式(I)化合物。需要的话,分离的化合物(I)可经由例如层析法、再结晶等技术来纯化。
也可将捕捉剂加入反应混合物中以通过结合副产物或未反应原料和简单过滤来除去那些副产物或未反应原料。对于细节参见"Synthesis andpurification catalog",Argonaut,2003及其中所引用的文献。
代硼酸或酯(III)可市购或可根据以下文献制备:"Science ofSynthesis",第6卷,Thieme,2005;WO 02/042275;Synlett 2003,(8)第1204页;J.Org.Chem.,2003,68,第3729页;Synthesis,2000,第442页;J.Org.Chem.,1995,60,第750页;或"Handbook offunctionalized organometallics",(P.Knochel编辑),Wiley,VCH,2005。
中间体(II)可通过磺酰氯(IV)与喹啉(V)在碱存在下反应而得到,其中在这些化合物中的变量具有如上文对式(I)的喹啉衍生物所定义的含义,且L和L1为离去基团:
该反应通常在-30℃至120℃,优选-10℃至100℃的温度下,在惰性有机溶剂中,在碱存在下进行(文献例如为:Lieb.Ann.Chem.P.641,1990)。
合适的溶剂为脂族烃,例如戊烷、己烷、环己烷和石油醚;芳族烃,例如甲苯、邻二甲苯、间二甲苯和对二甲苯;卤代烃,例如二氯甲烷、氯仿和氯苯;醚,例如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷、苯甲醚和四氢呋喃;腈,例如乙腈和丙腈;酮,例如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮;以及二甲亚砜、二甲基甲酰胺和二甲基乙酰胺;优选四氢呋喃、甲基叔丁基醚、二氯甲烷、氯仿、乙腈、甲苯或二甲基甲酰胺。也可使用所提及溶剂的混合物。
合适的碱通常为无机化合物,例如碱金属氢氧化物和碱土金属氢氧化物,例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙;碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钙和氧化镁;碱金属氢化物和碱土金属氢化物,例如氢化锂、氢化钠、氢化钾和氢化钙;碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钾和碳酸钙;以及碱金属碳酸氢盐,例如碳酸氢钠;此外为有机碱,例如叔胺,例如三甲胺、三乙胺、三异丙基乙胺和N-甲基哌啶、吡啶、被取代的吡啶(例如可力丁、卢剔啶和4-二甲基氨基吡啶),以及双环胺。尤其优选吡啶、三乙胺和碳酸钾。碱通常以等摩尔量、过量或合适的话作为溶剂使用。过量碱通常为相对于1摩尔化合物(V)为0.5-5摩尔当量。
原料通常以等摩尔量相互反应。
若磺酰氯(IV)不可市购,则其可根据本领域已知的程序获得。
喹啉(V)由文献已知或可市购(例如:4-亚甲基氨基喹啉:CAS号5632-13-3;6-氯-4-亚甲基氨基喹啉:CAS号859814-05-5;6-甲氧基-4-亚甲基氨基喹啉:CAS号708261-71-6;8-羟基-4-亚甲基氨基喹啉:CAS号33976-91-9;6-甲氧基-8-氯-4-亚甲基氨基喹啉:CAS号857207-07-9),或它们可由其中X如下所定义的喹啉前体(VI)在以下方案中通过还原而制备:
VIa:X=CH2NHOHV VId:X=C;HO
VIb:X=CN VIe:X=CH3
VIc:X=C(=O)NH2 VIf:X=Cl,Br
该还原方法例如可在如下文献中找到或对本领域熟练技术人员是已知的:Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Heterocycl.Chem.,1997,34(6),第1661-1667页;J.Chem.Soc.1954,第1165页;Heterocycles,41(4),第675-688页,1995;J.Org.Chem.,1982,47,第3153页;Heterocycles,1996,43(9),第1893-1900页;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994。
例如由如下文献所述,肟(VIa)可由相应醛(X=CHO;化合物(VId))或甲基衍生物(X=CH3;化合物(VIe))制备:Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994;Tetrahedron Lett.42(39),第6815-6818页,2001;或Heterocycles,29(9),第1741-1760页,1989。
醛(VId)可市购(例如,6-氯喹啉-4-醛、7-甲氧基喹啉-4-醛、喹啉-4-醛)或可如下列文献简述可由4-甲基喹啉合成:J.Org.Chem.51(4),第536-537页,1986,或如在以下文献中显示,由卤代衍生物(X=卤素,化合物(VIf))合成:Eur.J.Org.Chem.,2003,(8),第1576-1588页;Tetrahedron Lett.1999,40(19),第3719-3722页;Tetrahedron,1999,55(41),第12149-12156页。
甲基衍生物(VIe)可市购(例如,6-氯-4-甲基喹啉;6,8-二甲氧基喹啉)或可根据"Science of Synthesis",第15卷,Thieme,Stuttgart,2005合成。
例如在如下文献中描述,腈(VIb)可在有或无额外催化剂的情况下,由各卤素衍生物(VIf)(X=卤素,优选氯、溴或碘)通过与氰化物源反应来制备:Tetrahedron Lett.42(38),第6707-6710页,2001;Chem.Eur.J.,2003,9(8),第1828-1836页;Chem.Commun.(Cambridge),2004,(12),第1388-1389页;J.Organomet.Chem.2004,689(24),第4576-4583页;或J.Chem.Soc.Perk.T.,1(16),第2323-2326页,1999。或者,如在以下文献中概述,酰胺或肟可脱水成相应的腈(VIb):"Synthesis",Stuttgart,(10),第943-944页,1992;或其中引用的文献;或Heterocycl.Chem.1997,34(6),第1661-1667页。
4-卤代喹啉(VIf)可市购或可根据"Science of Synthesis",第15卷,Thieme,Stuttgart,2005或例如根据以下文献或其中的引文合成:4-氯-6,7-二甲氧基喹啉:Journal Med.Chem.48(5),第1359页,2005;4-氯-5,7-二氯喹啉:Indian,187817,2002年6月29日;4-氯-7-氯喹啉:Tetrahedron,60(13),第3017页,2004;4-氯-7-三氟甲基喹啉;Tetrahedron lett.,31(8),第1093页,1990;4-氯-7,8-二甲氧基喹啉:Tetrahedron,41(15),第3033页,1985;4-氯-8-甲氧基喹啉:Chem.Berichte 118(4),第1556页,1985;4-氯-(6或7或8)-碘喹啉、4-溴-(6或7或8)-碘喹啉、4-碘-(6或7或8)-碘喹啉:J.Med.Chem.,21(3),第268页,1978。
构建合适的前体或改变取代模式的其它方法可在"Synthesis",Stuttgart(1),第31-32页,1993;Tetrahedron,1993,49(24),第5315-5326页;"Methods in Science of Synthesis",Band 15,及其中引用的文献;Bioorg.Med.Chem.Lett.1997,7(23),第2935-2940页;J.Am.Chem.Soc.,1946,68,第1264页;或Org.Synth.1955,III,第272页中找到。
在相同情况下,就易于处理或纯化而言,在以一锅法(one pot)进行化合物(VI)至化合物(V)的还原和胺(V)与化合物(IV)的反应而不分离化合物(V)可能是有利的。
一些式II中间体是新的并显示杀虫活性。这些中间体也是本发明的主题。
式II.1的中间体尤其为本发明的主题:
其中L2为氯、溴或碘且其它变量如上对式I所定义,但不包括其中R4和R7为氢且R5和R6相同且选自氢、甲基、氟、氯、甲氧基和三氟甲氧基的化合物。
如果个别化合物I不可由上述途径获得,则其可通过衍生其它化合物I或经由所述合成途径的常规改变而制备。
式I化合物的制备可使其以异构体混合物(立体异构体、对映异构体)形式获得。需要的话,这些异构体混合物可经由常用于此的方法例如结晶或层析法,也可对光学活性吸附物进行拆分以得到纯异构体。
本发明的化合物I可以以生物活性可能不同的不同晶型存在。这些也是本发明的主题。
化合物I的可农用盐可以以常规方式,例如通过与所述阴离子的酸反应而形成。
在本说明书中和权利要求中,参考定义为具有如下含义的许多术语:
本文中使用的"盐"包括化合物I与如下化合物的加合物:马来酸、二马来酸、富马酸、二富马酸、甲烷次磺酸、甲烷磺酸和丁二酸。此外,包括在"盐"中的是例如可与如下化合物形成的那些盐:胺、金属、碱土金属碱或季铵碱,包括两性离子。作为成盐剂的合适的金属氢氧化物和碱土金属氢氧化物包括钡、铝、镍、铜、锰、钴、锌、铁、银、锂、钠、钾、镁或钙的盐。其它成盐剂包括氯化物、硫酸盐、乙酸盐、碳酸盐、氢化物和氢氧化物。所需要的盐包括化合物I与马来酸、二马来酸、富马酸、二富马酸和甲烷磺酸的加合物。
"卤素"应理解为指氟、氯、溴和碘。
本文中使用的术语"烷基"指具有1-6个碳原子的支化或未支化饱和烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。
本文中使用的术语"卤代烷基"指具有1-6个碳原子的直链或支化烷基(如上所述),其中这些基团中的一些或所有氢原子可被如上所述的卤原子替换,例如,C1-C2卤代烷基,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基;
类似地,"烷氧基"和"烷硫基"指在具有1-6个碳原子的直链或支化烷基(如上所述)的任何键处分别经由氧键或硫键键结的烷基。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、甲硫基、乙硫基、丙硫基、异丙硫基和正丁硫基。
类似地,"烷基亚磺酰基"和"烷基磺酰基"指在具有1-6个碳原子的直链或支化烷基(如上所述)的任何键处分别经由-S(=O)-或-S(=O)2-键键结的烷基。实例包括甲基亚磺酰基和甲基磺酰基。
本文中使用的术语"链烯基"指具有2-6个碳原子和在任意位置的双键的支化或未支化不饱和烃基,例如乙烯基、1-丙烯基、2-丙烯基、1-甲基-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基;1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基。
本文中使用的术语"炔基"指具有2-6个碳原子且含有至少一个叁键的支化或未支化不饱和烃基,例如乙炔基、丙炔基、1-丁炔基、2-丁炔基等。
类似地,"烯氧基"和"炔氧基"指在烯基的任何键处或在炔基不邻接叁键的碳原子的任意碳原子处经由氧键键结的具有2-6个碳原子的直链或支化烷基(如上所述),例如,烯丙氧基或炔丙氧基。
本文中使用的术语"环烷基"指单环3-7员饱和碳原子环,例如环丙基、环丁基、环戊基、环己基或环庚基。
关于式I化合物的意欲用途,尤其优选取代基的如下含义,在每种情况下单独或组合:
根据权利要求1的式I的喹啉衍生物,其中:
R1、R2、R3各自独立地为卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(Ra)=NORb,更优选氟、氯、溴、氰基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基或C1-C6卤代烷氧基;m和n各自独立地为1、2、3、4或5;且p为0、1、2、3、4或5。
根据权利要求1的式I的喹啉衍生物,其中R1、R2、R3各自独立地为氟、氯、溴、氰基、C1-C4烷基、C1-C6环烷基、C1-C4烷氧基、C2-C3链烯氧基、C2-C3炔氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基磺酰基、C1-C2卤代烷基磺酰基;且m、n和p的总和等于2或3。
根据权利要求1的式I的喹啉衍生物,其中R4、R5、R6、R7各自独立地为氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6烷硫基,优选氟、氯、溴、碘、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基或C1-C4烷硫基。
一种如下式I化合物,其中m、n和p的总和等于2或3。
一种如下式I化合物,其中在联苯基结构部分中标记为"2"的位置被氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基、二氟甲氧基或三氟甲氧基取代。
一种如下式I化合物,其中在联苯基结构部分中标记为"2"的位置被氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基、二氟甲氧基或三氟甲氧基取代,且m、n和p的总和等于2或3。
一种如下式I化合物,其中在联苯基结构部分中标记为"3"的位置被氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基、二氟甲氧基或三氟甲氧基取代。
一种如下式I化合物,其中在联苯基结构部分中标记为"3"的位置被氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基、二氟甲氧基或三氟甲氧基取代,且m、n和p的总和等于2或3。
一种如下式I.1化合物,其中联苯基结构部分具有如下方案中的取代模式,且R1和R2如上文对于式I化合物所定义:
一种如下式I.1化合物,其中联苯基结构部分具有上述取代模式,R1选自氟、氯、溴、甲基、甲氧基、三氟甲基、甲硫基、三氟甲硫基、二氟甲氧基和三氟甲氧基,且R2如上文对于式I化合物所定义。
一种如在前两段中定义的式I.1化合物,其带有另一个选自R3的取代基。
一种如下式I.2化合物,其中联苯基结构部分具有如下取代模式:
一种如下式I.2化合物,其具有另一个选自R3的取代基。
一种如下式I.3化合物,其中联苯基结构部分具有如下取代模式:
一种如下式I.3化合物,其具有另一个选自R3的取代基。
一种如下式I化合物,其中喹啉结构部分选自表A:
表A
*表示与骨架的键结位置
喹啉结构部分编号 | R4 | R5 | R6 | R7 |
Q-1 | H | H | H | H |
Q-2 | F | H | H | H |
Q-3 | H | F | H | H |
Q-4 | H | H | F | H |
Q-5 | H | H | H | F |
Q-6 | Cl | H | H | H |
Q-7 | H | Cl | H | H |
Q-8 | H | H | Cl | H |
Q-9 | H | H | H | Cl |
Q-10 | CH3 | H | H | H |
Q-11 | H | CH3 | H | H |
Q-12 | H | H | CH3 | H |
Q-13 | H | H | H | CH3 |
Q-14 | OCH3 | H | H | H |
Q-15 | H | OCH3 | H | H |
Q-16 | H | H | OCH3 | H |
Q-17 | H | H | H | OCH3 |
喹啉结构部分编号 | R4 | R5 | R6 | R7 |
Q-18 | CF3 | H | H | H |
Q-19 | H | CF3 | H | H |
Q-20 | H | H | CF3 | H |
Q-21 | H | H | H | CF3 |
Q-22 | OCF3 | H | H | H |
Q-23 | H | OCF3 | H | H |
Q-24 | H | H | OCF3 | H |
Q-25 | H | H | H | OCF3 |
Q-26 | Cl | Cl | H | H |
Q-27 | Cl | H | Cl | H |
Q-28 | Cl | H | H | Cl |
Q-29 | H | Cl | Cl | H |
Q-30 | H | Cl | H | Cl |
Q-31 | H | H | Cl | Cl |
Q-32 | F | F | H | H |
Q-33 | F | H | F | H |
Q-34 | F | H | H | F |
Q-35 | H | F | F | H |
Q-36 | H | F | H | F |
Q-37 | H | H | F | F |
Q-38 | CH3 | CH3 | H | H |
Q-39 | CH3 | H | CH3 | H |
Q-40 | CH3 | H | H | CH3 |
Q-41 | H | CH3 | CH3 | H |
Q-42 | H | CH3 | H | CH3 |
Q-43 | H | H | CH3 | CH3 |
Q-44 | OCH3 | OCH3 | H | H |
Q-45 | OCH3 | H | OCH3 | H |
Q-46 | OCH3 | H | H | OCH3 |
Q-47 | H | OCH3 | OCH3 | H |
Q-48 | H | OCH3 | H | OCH3 |
Q-49 | H | H | OCH3 | OCH3 |
Q-50 | CF3 | CF3 | H | H |
Q-51 | CF3 | H | CF3 | H |
Q-52 | CF3 | H | H | CF3 |
Q-53 | H | CF3 | CF3 | H |
Q-54 | H | CF3 | H | CF3 |
Q-55 | H | H | CF3 | CF3 |
对于它们的用途,尤其优选汇编于下表中的化合物I。此外,在表中对于取代基所提及的基团本身为所述取代基的特别优选的实施方案,而与其中提及它们的组合无关。
表1
其中Q表示Q-1,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表2
其中Q表示Q-2,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表3
其中Q表示Q-3,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表4
其中Q表示Q-4,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表5
其中Q表示Q-5,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表6
其中Q表示Q-6,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表7
其中Q表示Q-8,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表8
其中Q表示Q-10,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表9
其中Q表示Q-12,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表10
其中Q表示Q-14,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表11
其中Q表示Q-16,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表12
其中Q表示Q-18,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表13
其中Q表示Q-20,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表14
其中Q表示Q-22,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表15
其中Q表示Q-24,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表16
其中Q表示Q-27,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表17
其中Q表示Q-33,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表18
其中Q表示Q-39,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表19
其中Q表示Q-45,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表20
其中Q表示Q-51,p为零,且(R1)m和(R2)n的组合在每种情况下对应于表B中的一个组合编号的式IA化合物。
表21
其中Q表示Q-1,(R3)p为4-F,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表22
其中Q表示Q-1,(R3)p为4-Cl,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表23
其中Q表示Q-1,(R3)p为4-Br,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表24
其中Q表示Q-1,(R3)p为4-CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表25
其中Q表示Q-1,(R3)p为4-CH2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表26
其中Q表示Q-1,(R3)p为4-C(CH3)3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表27
其中Q表示Q-1,(R3)p为4-OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表28
其中Q表示Q-1,(R3)p为4-OCH2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表29
其中Q表示Q-1,(R3)p为4-CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表30
其中Q表示Q-1,(R3)p为4-CH(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表31
其中Q表示Q-1,(R3)p为4-CF(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表32
其中Q表示Q-1,(R3)p为4-C(OH)(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表33
其中Q表示Q-1,(R3)p为4-OCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表34
其中Q表示Q-1,(R3)p为4-OCHF2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表35
其中Q表示Q-1,(R3)p为4-SCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表36
其中Q表示Q-1,(R3)p为4-SO2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表37
其中Q表示Q-1,(R3)p为4-CN,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表38
其中Q表示Q-1,(R3)p为4-SCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表39
其中Q表示Q-1,(R3)p为4-SO2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表40
其中Q表示Q-1,(R3)p为4-OCF2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表41
其中Q表示Q-1,(R3)p为4-OCH2CHCH2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表42
其中Q表示Q-1,(R3)p为4-CH2CCH,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表43
其中Q表示Q-1,(R3)p为4-CH2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表44
其中Q表示Q-1,(R3)p为4-CH2CH2OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表45
其中Q表示Q-1,(R3)p为4-OC(CH3)3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表46
其中Q表示Q-1,(R3)p为4-OCH2-环C3H5,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表47
其中Q表示Q-1,(R3)p为5-F,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表48
其中Q表示Q-1,(R3)p为5-Cl,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表49
其中Q表示Q-1,(R3)p为5-Br,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表50
其中Q表示Q-1,(R3)p为5-CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表51
其中Q表示Q-1,(R3)p为5-OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表52
其中Q表示Q-1,(R3)p为5-CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表53
其中Q表示Q-1,(R3)p为5-OCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表54
其中Q表示Q-1,(R3)p为5-SCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表55
其中Q表示Q-1,(R3)p为5-OCHF2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表56
其中Q表示Q-5,(R3)p为4-F,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表57
其中Q表示Q-5,(R3)p为4-Cl,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表58
其中Q表示Q-5,(R3)p为4-Br,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表59
其中Q表示Q-5,(R3)p为4-CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表60
其中Q表示Q-5,(R3)p为4-CH2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表61
其中Q表示Q-5,(R3)p为4-C(CH3)3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表62
其中Q表示Q-5,(R3)p为4-OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表63
其中Q表示Q-5,(R3)p为4-OCH2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表64
其中Q表示Q-5,(R3)p为4-CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表65
其中Q表示Q-5,(R3)p为4-CH(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表66
其中Q表示Q-5,(R3)p为4-CF(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表67
其中Q表示Q-5,(R3)p为4-C(OH)(CF3)2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表68
其中Q表示Q-5,(R3)p为4-OCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表69
其中Q表示Q-5,(R3)p为4-OCHF2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表70
其中Q表示Q-5,(R3)p为4-SCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表71
其中Q表示Q-5,(R3)p为4-SO2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表72
其中Q表示Q-5,(R3)p为4-CN,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表73
其中Q表示Q-5,(R3)p为4-SCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表74
其中Q表示Q-5,(R3)p为4-SO2CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表75
其中Q表示Q-5,(R3)p为4-OCF2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表76
其中Q表示Q-5,(R3)p为4-OCH2CHCH2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表77
其中Q表示Q-5,(R3)p为4-CH2CCH,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表78
其中Q表示Q-5,(R3)p为4-CH2CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表79
其中Q表示Q-5,(R3)p为4-CH2CH2OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表80
其中Q表示Q-5,(R3)p为4-OC(CH3)3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表81
其中Q表示Q-5,(R3)p为4-OCH2-环C3H5,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-469至IA-1459中的一个组合编号的式IA化合物。
表82
其中Q表示Q-5,(R3)p为5-F,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表83
其中Q表示Q-5,(R3)p为5-Cl,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表84
其中Q表示Q-5,(R3)p为5-Br,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表85
其中Q表示Q-5,(R3)p为5-CH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表86
其中Q表示Q-5,(R3)p为5-OCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表87
其中Q表示Q-5,(R3)p为5-CF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表88
其中Q表示Q-5,(R3)p为5-OCF3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表89
其中Q表示Q-5,(R3)p为5-SCH3,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表90
其中Q表示Q-5,(R3)p为5-OCHF2,且(R1)m和(R2)n的组合在每种情况下对应于表B的选自IA-1至IA-702和IA-1379至IA-1459中的一个组合编号的式IA化合物。
表B中的编号*表示组合编号
表B
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1 | 2-F | 4-F | IA-2 | 2-F | 4-Cl |
IA-3 | 2-F | 4-Br | IA-4 | 2-F | 4-CH3 |
IA-5 | 2-F | 4-CH2CH3 | IA-6 | 2-F | 4-C(CH3)3 |
IA-7 | 2-F | 4-OCH3 | IA-8 | 2-F | 4-OCH2CH3 |
IA-9 | 2-F | 4-CF3 | IA-10 | 2-F | 4-CH(CF3)2 |
IA-11 | 2-F | 4-OC(CH3)3 | IA-12 | 2-F | 4-CF(CF3)2 |
IA-13 | 2-F | 4-OCF3 | IA-14 | 2-F | 4-OCHF2 |
IA-15 | 2-F | 4-SCF3 | IA-16 | 2-F | 4-SO2CF3 |
IA-17 | 2-F | 4-CN | IA-18 | 2-F | 4-SCH3 |
IA-19 | 2-F | 4-SO2CH3 | IA-20 | 2-F | 4-OCF2CF3 |
IA-21 | 2-F | 4-OCH2CHCH2 | IA-22 | 2-F | 4-OCH2CH2OCH3 |
IA-23 | 2-F | 4-OCH2CF3 | IA-24 | 2-F | 4-OCH2CCH |
IA-25 | 2-F | 4-OCH2-环-C3H5 | IA-26 | 2-F | 4-C(OH)(CF3)2 |
IA-27 | 2-Cl | 4-F | IA-28 | 2-Cl | 4-Cl |
IA-29 | 2-Cl | 4-Br | IA-30 | 2-Cl | 4-CH3 |
IA-31 | 2-Cl | 4-CH2CH3 | IA-32 | 2-Cl | 4-C(CH3)3 |
IA-33 | 2-Cl | 4-OCH3 | IA-34 | 2-Cl | 4-OCH2CH3 |
IA-35 | 2-Cl | 4-CF3 | IA-36 | 2-Cl | 4-CH(CF3)2 |
IA-37 | 2-Cl | 4-OC(CH3)3 | IA-38 | 2-Cl | 4-CF(CF3)2 |
IA-39 | 2-Cl | 4-OCF3 | IA-40 | 2-Cl | 4-OCHF2 |
IA-41 | 2-Cl | 4-SCF3 | IA-42 | 2-Cl | 4-SO2CF3 |
IA-43 | 2-Cl | 4-CN | IA-44 | 2-Cl | 4-SCH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-45 | 2-Cl | 4-SO2CH3 | IA-46 | 2-Cl | 4-OCF2CF3 |
IA-47 | 2-Cl | 4-OCH2CHCH2 | IA-48 | 2-Cl | 4-OCH2CH2OCH3 |
IA-49 | 2-Cl | 4-OCH2CF3 | IA-50 | 2-Cl | 4-OCH2CCH |
IA-51 | 2-Cl | 4-OCH2-环-C3H5 | IA-52 | 2-Cl | 4-C(OH)(CF3)2 |
IA-53 | 2-Br | 4-F | IA-54 | 2-Br | 4-Cl |
IA-55 | 2-Br | 4-Br | IA-56 | 2-Cl | 4-CH3 |
IA-57 | 2-Br | 4-CH2CH3 | IA-58 | 2-Br | 4-C(CH3)3 |
IA-59 | 2-Br | 4-OCH3 | IA-60 | 2-Br | 4-OCH2CH3 |
IA-61 | 2-Br | 4-CF3 | IA-62 | 2-Br | 4-CH(CF3)2 |
IA-63 | 2-Br | 4-OC(CH3)3 | IA-64 | 2-Br | 4-CF(CF3)2 |
IA-65 | 2-Br | 4-OCF3 | IA-66 | 2-Br | 4-OCHF2 |
IA-67 | 2-Br | 4-SCF3 | IA-68 | 2-Br | 4-SO2CF3 |
IA-69 | 2-Br | 4-CN | IA-70 | 2-Br | 4-SCH3 |
IA-71 | 2-Br | 4-SO2CH3 | IA-72 | 2-Br | 4-OCF2CF3 |
IA-73 | 2-Br | 4-OCH2CHCH2 | IA-74 | 2-Br | 4-OCH2CH2OCH3 |
IA-75 | 2-Br | 4-OCH2CF3 | IA-76 | 2-Br | 4-OCH2CCH |
IA-77 | 2-Br | 4-OCH2-环-C3H5 | IA-78 | 2-Br | 4-C(OH)(CF3)2 |
IA-79 | 2-CH3 | 4-F | IA-80 | 2-CH3 | 4-Cl |
IA-81 | 2-CH3 | 4-Br | IA-82 | 2-CH3 | 4-CH3 |
IA-83 | 2-CH3 | 4-CH2CH3 | IA-84 | 2-CH3 | 4-C(CH3)3 |
IA-85 | 2-CH3 | 4-OCH3 | IA-86 | 2-CH3 | 4-OCH2CH3 |
IA-87 | 2-CH3 | 4-CF3 | IA-88 | 2-CH3 | 4-CH(CF3)2 |
IA-89 | 2-CH3 | 4-OC(CH3)3 | IA-90 | 2-CH3 | 4-CF(CF3)2 |
IA-91 | 2-CH3 | 4-OCF3 | IA-92 | 2-CH3 | 4-OCHF2 |
IA-93 | 2-CH3 | 4-SCF3 | IA-94 | 2-CH3 | 4-SO2CF3 |
IA-95 | 2-CH3 | 4-CN | IA-96 | 2-CH3 | 4-SCH3 |
IA-97 | 2-CH3 | 4-SO2CH3 | IA-98 | 2-CH3 | 4-OCF2CF3 |
IA-99 | 2-CH3 | 4-OCH2CHCH2 | IA-100 | 2-CH3 | 4-OCH2CH2OCH3 |
IA-101 | 2-CH3 | 4-OCH2CF3 | IA-102 | 2-CH3 | 4-OCH2CCH |
IA-103 | 2-CH3 | 4-OCH2-环-C3H5 | IA-104 | 2-CH3 | 4-C(OH)(CF3)2 |
IA-105 | 2-OCH3 | 4-F | IA-106 | 2-OCH3 | 4-Cl |
IA-107 | 2-OCH3 | 4-Br | IA-108 | 2-OCH3 | 4-CH3 |
IA-109 | 2-OCH3 | 4-CH2CH3 | IA-110 | 2-OCH3 | 4-C(CH3)3 |
IA-111 | 2-OCH3 | 4-OCH3 | IA-112 | 2-OCH3 | 4-OCH2CH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-113 | 2-OCH3 | 4-CF3 | IA-114 | 2-OCH3 | 4-CH(CF3)2 |
IA-115 | 2-OCH3 | 4-OC(CH3)3 | IA-116 | 2-OCH3 | 4-CF(CF3)2 |
IA-117 | 2-OCH3 | 4-OCF3 | IA-118 | 2-OCH3 | 4-OCHF2 |
IA-119 | 2-OCH3 | 4-SCF3 | IA-120 | 2-OCH3 | 4-SO2CF3 |
IA-121 | 2-OCH3 | 4-CN | IA-122 | 2-OCH3 | 4-SCH3 |
IA-123 | 2-OCH3 | 4-SO2CH3 | IA-124 | 2-OCH3 | 4-OCF2CF3 |
IA-125 | 2-OCH3 | 4-OCH2CHCH2 | IA-126 | 2-OCH3 | 4-OCH2CH2OCH3 |
IA-127 | 2-OCH3 | 4-OCH2CF3 | IA-128 | 2-OCH3 | 4-OCH2CCH |
IA-129 | 2-OCH3 | 4-OCH2-环-C3H5 | IA-130 | 2-OCH3 | 4-C(OH)(CF3)2 |
IA-131 | 2-CF3 | 4-F | IA-132 | 2-CF3 | 4-Cl |
IA-133 | 2-CF3 | 4-Br | IA-134 | 2-CF3 | 4-CH3 |
IA-135 | 2-CF3 | 4-CH2CH3 | IA-136 | 2-CF3 | 4-C(CH3)3 |
IA-137 | 2-CF3 | 4-OCH3 | IA-138 | 2-CF3 | 4-OCH2CH3 |
IA-139 | 2-CF3 | 4-CF3 | IA-140 | 2-CF3 | 4-CH(CF3)2 |
IA-141 | 2-CF3 | 4-OC(CH3)3 | IA-142 | 2-CF3 | 4-CF(CF3)2 |
IA-143 | 2-CF3 | 4-OCF3 | IA-144 | 2-CF3 | 4-OCHF2 |
IA-145 | 2-CF3 | 4-SCF3 | IA-146 | 2-CF3 | 4-SO2CF3 |
IA-147 | 2-CF3 | 4-CN | IA-148 | 2-CF3 | 4-SCH3 |
IA-149 | 2-CF3 | 4-SO2CH3 | IA-150 | 2-CF3 | 4-OCF2CF3 |
IA-151 | 2-CF3 | 4-OCH2CHCH2 | IA-152 | 2-CF3 | 4-OCH2CH2OCH3 |
IA-153 | 2-CF3 | 4-OCH2CF3 | IA-154 | 2-CF3 | 4-OCH2CCH |
IA-155 | 2-CF3 | 4-OCH2-环-C3H5 | IA-156 | 2-CF3 | 4-C(OH)(CF3)2 |
IA-157 | 2-OCF3 | 4-F | IA-158 | 2-OCF3 | 4-Cl |
IA-159 | 2-OCF3 | 4-Br | IA-160 | 2-OCF3 | 4-CH3 |
IA-161 | 2-OCF3 | 4-CH2CH3 | IA-162 | 2-OCF3 | 4-C(CH3)3 |
IA-163 | 2-OCF3 | 4-OCH3 | IA-164 | 2-OCF3 | 4-OCH2CH3 |
IA-165 | 2-OCF3 | 4-CF3 | IA-166 | 2-OCF3 | 4-CH(CF3)2 |
IA-167 | 2-OCF3 | 4-OC(CH3)3 | IA-168 | 2-OCF3 | 4-CF(CF3)2 |
IA-169 | 2-OCF3 | 4-OCF3 | IA-170 | 2-OCF3 | 4-OCHF2 |
IA-171 | 2-OCF3 | 4-SCF3 | IA-172 | 2-OCF3 | 4-SO2CF3 |
IA-173 | 2-OCF3 | 4-CN | IA-174 | 2-OCF3 | 4-SCH3 |
IA-175 | 2-OCF3 | 4-SO2CH3 | IA-176 | 2-OCF3 | 4-OCF2CF3 |
IA-177 | 2-OCF3 | 4-OCH2CHCH2 | IA-178 | 2-OCF3 | 4-OCH2CH2OCH3 |
IA-179 | 2-OCF3 | 4-OCH2CF3 | IA-180 | 2-OCF3 | 4-OCH2CCH |
IA-181 | 2-OCF3 | 4-OCH2-环 | IA-182 | 2-OCF3 | 4-C(OH)(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
-C3H5 | |||||
IA-183 | 2-SCH3 | 4-F | IA-184 | 2-SCH3 | 4-Cl |
IA-185 | 2-SCH3 | 4-Br | IA-186 | 2-SCH3 | 4-CH3 |
IA-187 | 2-SCH3 | 4-CH2CH3 | IA-188 | 2-SCH3 | 4-C(CH3)3 |
IA-189 | 2-SCH3 | 4-OCH3 | IA-190 | 2-SCH3 | 4-OCH2CH3 |
IA-191 | 2-SCH3 | 4-CF3 | IA-192 | 2-SCH3 | 4-CH(CF3)2 |
IA-193 | 2-SCH3 | 4-OC(CH3)3 | IA-194 | 2-SCH3 | 4-CF(CF3)2 |
IA-195 | 2-SCH3 | 4-OCF3 | IA-196 | 2-SCH3 | 4-OCHF2 |
IA-197 | 2-SCH3 | 4-SCF3 | IA-198 | 2-SCH3 | 4-SO2CF3 |
IA-199 | 2-SCH3 | 4-CN | IA-200 | 2-SCH3 | 4-SCH3 |
IA-201 | 2-SCH3 | 4-SO2CH3 | IA-202 | 2-SCH3 | 4-OCF2CF3 |
IA-203 | 2-SCH3 | 4-OCH2CHCH2 | IA-204 | 2-SCH3 | 4-OCH2CH2OCH3 |
IA-205 | 2-SCH3 | 4-OCH2CF3 | IA-206 | 2-SCH3 | 4-OCH2CCH |
IA-207 | 2-SCH3 | 4-OCH2-环-C3H5 | IA-208 | 2-SCH3 | 4-C(OH)(CF3)2 |
IA-209 | 2-OCHF2 | 4-F | IA-210 | 2-OCHF2 | 4-Cl |
IA-211 | 2-OCHF2 | 4-Br | IA-212 | 2-OCHF2 | 4-CH3 |
IA-213 | 2-OCHF2 | 4-CH2CH3 | IA-214 | 2-OCHF2 | 4-C(CH3)3 |
IA-215 | 2-OCHF2 | 4-OCH3 | IA-216 | 2-OCHF2 | 4-OCH2CH3 |
IA-217 | 2-OCHF2 | 4-CF3 | IA-218 | 2-OCHF2 | 4-CH(CF3)2 |
IA-219 | 2-OCHF2 | 4-OC(CH3)3 | IA-220 | 2-OCHF2 | 4-CF(CF3)2 |
IA-221 | 2-OCHF2 | 4-OCF3 | IA-222 | 2-OCHF2 | 4-OCHF2 |
IA-223 | 2-OCHF2 | 4-SCF3 | IA-224 | 2-OCHF2 | 4-SO2CF3 |
IA-225 | 2-OCHF2 | 4-CN | IA-226 | 2-OCHF2 | 4-SCH3 |
IA-227 | 2-OCHF2 | 4-SO2CH3 | IA-228 | 2-OCHF2 | 4-OCF2CF3 |
IA-229 | 2-OCHF2 | 4-OCH2CHCH2 | IA-230 | 2-OCHF2 | 4-OCH2CH2OCH3 |
IA-231 | 2-OCHF2 | 4-OCH2CF3 | IA-232 | 2-OCHF2 | 4-OCH2CCH |
IA-233 | 2-OCHF2 | 4-OCH2-环-C3H5 | IA-234 | 2-OCHF2 | 4-C(OH)(CF3)2 |
IA-235 | 3-F | 4-F | IA-236 | 3-F | 4-Cl |
IA-237 | 3-F | 4-Br | IA-238 | 3-F | 4-CH3 |
IA-239 | 3-F | 4-CH2CH3 | IA-240 | 3-F | 4-C(CH3)3 |
IA-241 | 3-F | 4-OCH3 | IA-242 | 3-F | 4-OCH2CH3 |
IA-243 | 3-F | 4-CF3 | IA-244 | 3-F | 4-CH(CF3)2 |
IA-245 | 3-F | 4-OC(CH3)3 | IA-246 | 3-F | 4-CF(CF3)2 |
IA-247 | 3-F | 4-OCF3 | IA-248 | 3-F | 4-OCHF2 |
IA-249 | 3-F | 4-SCF3 | IA-250 | 3-F | 4-SO2CF3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-251 | 3-F | 4-CN | IA-252 | 3-F | 4-SCH3 |
IA-253 | 3-F | 4-SO2CH3 | IA-254 | 3-F | 4-OCF2CF3 |
IA-255 | 3-F | 4-OCH2CHCH2 | IA-256 | 3-F | 4-OCH2CH2OCH3 |
IA-257 | 3-F | 4-OCH2CF3 | IA-258 | 3-F | 4-OCH2CCH |
IA-259 | 3-F | 4-OCH2-环-C3H5 | IA-260 | 3-F | 4-C(OH)(CF3)2 |
IA-261 | 3-Cl | 4-F | IA-262 | 3-Cl | 4-Cl |
IA-263 | 3-Cl | 4-Br | IA-264 | 3-Cl | 4-CH3 |
IA-265 | 3-Cl | 4-CH2CH3 | IA-266 | 3-Cl | 4-C(CH3)3 |
IA-267 | 3-Cl | 4-OCH3 | IA-268 | 3-Cl | 4-OCH2CH3 |
IA-269 | 3-Cl | 4-CF3 | IA-270 | 3-Cl | 4-CH(CF3)2 |
IA-271 | 3-Cl | 4-OC(CH3)3 | IA-272 | 3-Cl | 4-CF(CF3)2 |
IA-273 | 3-Cl | 4-OCF3 | IA-274 | 3-Cl | 4-OCHF2 |
IA-275 | 3-Cl | 4-SCF3 | IA-276 | 3-Cl | 4-SO2CF3 |
IA-277 | 3-Cl | 4-CN | IA-278 | 3-Cl | 4-SCH3 |
IA-279 | 3-Cl | 4-SO2CH3 | IA-280 | 3-Cl | 4-OCF2CF3 |
IA-281 | 3-Cl | 4-OCH2CHCH2 | IA-282 | 3-Cl | 4-OCH2CH2OCH3 |
IA-283 | 3-Cl | 4-OCH2CF3 | IA-284 | 3-Cl | 4-OCH2CCH |
IA-285 | 3-Cl | 4-OCH2-环-C3H5 | IA-286 | 3-Cl | 4-C(OH)(CF3)2 |
IA-287 | 3-Br | 4-F | IA-288 | 3-Br | 4-Cl |
IA-289 | 3-Br | 4-Br | IA-290 | 3-Cl | 4-CH3 |
IA-291 | 3-Br | 4-CH2CH3 | IA-292 | 3-Br | 4-C(CH3)3 |
IA-293 | 3-Br | 4-OCH3 | IA-294 | 3-Br | 4-OCH2CH3 |
IA-295 | 3-Br | 4-CF3 | IA-296 | 3-Br | 4-CH(CF3)2 |
IA-297 | 3-Br | 4-OC(CH3)3 | IA-298 | 3-Br | 4-CF(CF3)2 |
IA-299 | 3-Br | 4-OCF3 | IA-300 | 3-Br | 4-OCHF2 |
IA-301 | 3-Br | 4-SCF3 | IA-302 | 3-Br | 4-SO2CF3 |
IA-303 | 3-Br | 4-CN | IA-304 | 3-Br | 4-SCH3 |
IA-305 | 3-Br | 4-SO2CH3 | IA-306 | 3-Br | 4-OCF2CF3 |
IA-307 | 3-Br | 4-OCH2CHCH2 | IA-308 | 3-Br | 4-OCH2CH2OCH3 |
IA-309 | 3-Br | 4-OCH2CF3 | IA-310 | 3-Br | 4-OCH2CCH |
IA-311 | 3-Br | 4-OCH2-环-C3H5 | IA-312 | 3-Br | 4-C(OH)(CF3)2 |
IA-313 | 3-CH3 | 4-F | IA-314 | 3-CH3 | 4-Cl |
IA-315 | 3-CH3 | 4-Br | IA-316 | 3-CH3 | 4-CH3 |
IA-317 | 3-CH3 | 4-CH2CH3 | IA-318 | 3-CH3 | 4-C(CH3)3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-319 | 3-CH3 | 4-OCH3 | IA-320 | 3-CH3 | 4-OCH2CH3 |
IA-321 | 3-CH3 | 4-CF3 | IA-322 | 3-CH3 | 4-CH(CF3)2 |
IA-323 | 3-CH3 | 4-OC(CH3)3 | IA-324 | 3-CH3 | 4-CF(CF3)2 |
IA-325 | 3-CH3 | 4-OCF3 | IA-326 | 3-CH3 | 4-OCHF2 |
IA-327 | 3-CH3 | 4-SCF3 | IA-328 | 3-CH3 | 4-SO2CF3 |
IA-329 | 3-CH3 | 4-CN | IA-330 | 3-CH3 | 4-SCH3 |
IA-331 | 3-CH3 | 4-SO2CH3 | IA-332 | 3-CH3 | 4-OCF2CF3 |
IA-333 | 3-CH3 | 4-OCH2CHCH2 | IA-334 | 3-CH3 | 4-OCH2CH2OCH3 |
IA-335 | 3-CH3 | 4-OCH2CF3 | IA-336 | 3-CH3 | 4-OCH2CCH |
IA-337 | 3-CH3 | 4-OCH2-环-C3H5 | IA-338 | 3-CH3 | 4-C(OH)(CF3)2 |
IA-339 | 3-OCH3 | 4-F | IA-340 | 3-OCH3 | 4-Cl |
IA-341 | 3-OCH3 | 4-Br | IA-342 | 3-OCH3 | 4-CH3 |
IA-343 | 3-OCH3 | 4-CH2CH3 | IA-344 | 3-OCH3 | 4-C(CH3)3 |
IA-345 | 3-OCH3 | 4-OCH3 | IA-346 | 3-OCH3 | 4-OCH2CH3 |
IA-347 | 3-OCH3 | 4-CF3 | IA-348 | 3-OCH3 | 4-CH(CF3)2 |
IA-349 | 3-OCH3 | 4-OC(CH3)3 | IA-350 | 3-OCH3 | 4-CF(CF3)2 |
IA-351 | 3-OCH3 | 4-OCF3 | IA-352 | 3-OCH3 | 4-OCHF2 |
IA-353 | 3-OCH3 | 4-SCF3 | IA-354 | 3-OCH3 | 4-SO2CF3 |
IA-355 | 3-OCH3 | 4-CN | IA-356 | 3-OCH3 | 4-SCH3 |
IA-357 | 3-OCH3 | 4-SO2CH3 | IA-358 | 3-OCH3 | 4-OCF2CF3 |
IA-359 | 3-OCH3 | 4-OCH2CHCH2 | IA-360 | 3-OCH3 | 4-OCH2CH2OCH3 |
IA-361 | 3-OCH3 | 4-OCH2CF3 | IA-362 | 3-OCH3 | 4-OCH2CCH |
IA-363 | 3-OCH3 | 4-OCH2-环-C3H5 | IA-364 | 3-OCH3 | 4-C(OH)(CF3)2 |
IA-365 | 3-CF3 | 4-F | IA-366 | 3-CF3 | 4-Cl |
IA-367 | 3-CF3 | 4-Br | IA-368 | 3-CF3 | 4-CH3 |
IA-369 | 3-CF3 | 4-CH2CH3 | IA-370 | 3-CF3 | 4-C(CH3)3 |
IA-371 | 3-CF3 | 4-OCH3 | IA-372 | 3-CF3 | 4-OCH2CH3 |
IA-373 | 3-CF3 | 4-CF3 | IA-374 | 3-CF3 | 4-CH(CF3)2 |
IA-375 | 3-CF3 | 4-OC(CH3)3 | IA-376 | 3-CF3 | 4-CF(CF3)2 |
IA-377 | 3-CF3 | 4-OCF3 | IA-378 | 3-CF3 | 4-OCHF2 |
IA-379 | 3-CF3 | 4-SCF3 | IA-380 | 3-CF3 | 4-SO2CF3 |
IA-381 | 3-CF3 | 4-CN | IA-382 | 3-CF3 | 4-SCH3 |
IA-383 | 3-CF3 | 4-SO2CH3 | IA-384 | 3-CF3 | 4-OCF2CF3 |
IA-385 | 3-CF3 | 4-OCH2CHCH2 | IA-386 | 3-CF3 | 4-OCH2CH2OCH3 |
IA-387 | 3-CF3 | 4-OCH2CF3 | IA-388 | 3-CF3 | 4-OCH2CCH |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-389 | 3-CF3 | 4-OCH2-环-C3H5 | IA-390 | 3-CF3 | 4-C(OH)(CF3)2 |
IA-391 | 3-OCF3 | 4-F | IA-392 | 3-OCF3 | 4-Cl |
IA-393 | 3-OCF3 | 4-Br | IA-394 | 3-OCF3 | 4-CH3 |
IA-395 | 3-OCF3 | 4-CH2CH3 | IA-396 | 3-OCF3 | 4-C(CH3)3 |
IA-397 | 3-OCF3 | 4-OCH3 | IA-398 | 3-OCF3 | 4-OCH2CH3 |
IA-399 | 3-OCF3 | 4-CF3 | IA-400 | 3-OCF3 | 4-CH(CF3)2 |
IA-401 | 3-OCF3 | 4-OC(CH3)3 | IA-402 | 3-OCF3 | 4-CF(CF3)2 |
IA-403 | 3-OCF3 | 4-OCF3 | IA-404 | 3-OCF3 | 4-OCHF2 |
IA-405 | 3-OCF3 | 4-SCF3 | IA-406 | 3-OCF3 | 4-SO2CF3 |
IA-407 | 3-OCF3 | 4-CN | IA-408 | 3-OCF3 | 4-SCH3 |
IA-409 | 3-OCF3 | 4-SO2CH3 | IA-410 | 3-OCF3 | 4-OCF2CF3 |
IA-411 | 3-OCF3 | 4-OCH2CHCH2 | IA-412 | 3-OCF3 | 4-OCH2CH2OCH3 |
IA-413 | 3-OCF3 | 4-OCH2CF3 | IA-414 | 3-OCF3 | 4-OCH2CCH |
IA-415 | 3-OCF3 | 4-OCH2-环-C3H5 | IA-416 | 3-OCF3 | 4-C(OH)(CF3)2 |
IA-417 | 3-SCH3 | 4-F | IA-418 | 3-SCH3 | 4-Cl |
IA-419 | 3-SCH3 | 4-Br | IA-420 | 3-SCH3 | 4-CH3 |
IA-421 | 3-SCH3 | 4-CH2CH3 | IA-422 | 3-SCH3 | 4-C(CH3)3 |
IA-423 | 3-SCH3 | 4-OCH3 | IA-424 | 3-SCH3 | 4-OCH2CH3 |
IA-425 | 3-SCH3 | 4-CF3 | IA-426 | 3-SCH3 | 4-CH(CF3)2 |
IA-427 | 3-SCH3 | 4-OC(CH3)3 | IA-428 | 3-SCH3 | 4-CF(CF3)2 |
IA-429 | 3-SCH3 | 4-OCF3 | IA-430 | 3-SCH3 | 4-OCHF2 |
IA-431 | 3-SCH3 | 4-SCF3 | IA-432 | 3-SCH3 | 4-SO2CF3 |
IA-433 | 3-SCH3 | 4-CN | IA-434 | 3-SCH3 | 4-SCH3 |
IA-435 | 3-SCH3 | 4-SO2CH3 | IA-436 | 3-SCH3 | 4-OCF2CF3 |
IA-437 | 3-SCH3 | 4-OCH2CHCH2 | IA-438 | 3-SCH3 | 4-OCH2CH2OCH3 |
IA-439 | 3-SCH3 | 4-OCH2CF3 | IA-440 | 3-SCH3 | 4-OCH2CCH |
IA-441 | 3-SCH3 | 4-OCH2-环-C3H5 | IA-442 | 3-SCH3 | 4-C(OH)(CF3)2 |
IA-443 | 3-OCHF2 | 4-F | IA-444 | 3-OCHF2 | 4-Cl |
IA-445 | 3-OCHF2 | 4-Br | IA-446 | 3-OCHF2 | 4-CH3 |
IA-447 | 3-OCHF2 | 4-CH2CH3 | IA-448 | 3-OCHF2 | 4-C(CH3)3 |
IA-449 | 3-OCHF2 | 4-OCH3 | IA-450 | 3-OCHF2 | 4-OCH2CH3 |
IA-451 | 3-OCHF2 | 4-CF3 | IA-452 | 3-OCHF2 | 4-CH(CF3)2 |
IA-453 | 3-OCHF2 | 4-OC(CH3)3 | IA-454 | 3-OCHF2 | 4-CF(CF3)2 |
IA-455 | 3-OCHF2 | 4-OCF3 | IA-456 | 3-OCHF2 | 4-OCHF2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-457 | 3-OCHF2 | 4-SCF3 | IA-458 | 3-OCHF2 | 4-SO2CF3 |
IA-459 | 3-OCHF2 | 4-CN | IA-460 | 3-OCHF2 | 4-SCH3 |
IA-461 | 3-OCHF2 | 4-SO2CH3 | IA-462 | 3-OCHF2 | 4-OCF2CF3 |
IA-463 | 3-OCHF2 | 4-OCH2CHCH2 | IA-464 | 3-OCHF2 | 4-OCH2CH2OCH3 |
IA-465 | 3-OCHF2 | 4-OCH2CF3 | IA-466 | 3-OCHF2 | 4-OCH2CCH |
IA-467 | 3-OCHF2 | 4-OCH2-环-C3H5 | IA-468 | 3-OCHF2 | 4-C(OH)(CF3)2 |
IA-469 | 2-F | 3-F | IA-470 | 2-F | 3-Cl |
IA-471 | 2-F | 3-Br | IA-472 | 2-F | 3-CH3 |
IA-473 | 2-F | 3-CH2CH3 | IA-474 | 2-F | 3-C(CH3)3 |
IA-475 | 2-F | 3-OCH3 | IA-476 | 2-F | 3-OCH2CH3 |
IA-477 | 2-F | 3-CF3 | IA-478 | 2-F | 3-CH(CF3)2 |
IA-479 | 2-F | 3-OC(CH3)3 | IA-480 | 2-F | 3-CF(CF3)2 |
IA-481 | 2-F | 3-OCF3 | IA-482 | 2-F | 3-OCHF2 |
IA-483 | 2-F | 3-SCF3 | IA-484 | 2-F | 3-SO2CF3 |
IA-485 | 2-F | 3-CN | IA-486 | 2-F | 3-SCH3 |
IA-487 | 2-F | 3-SO2CH3 | IA-488 | 2-F | 3-OCF2CF3 |
IA-489 | 2-F | 3-OCH2CHCH2 | IA-490 | 2-F | 3-OCH2CH2OCH3 |
IA-491 | 2-F | 3-OCH2CF3 | IA-492 | 2-F | 3-OCH2CCH |
IA-493 | 2-F | 3-OCH2-环-C3H5 | IA-494 | 2-F | 3-C(OH)(CF3)2 |
IA-495 | 2-Cl | 3-F | IA-496 | 2-Cl | 3-Cl |
IA-497 | 2-Cl | 3-Br | IA-498 | 2-Cl | 3-CH3 |
IA-499 | 2-Cl | 3-CH2CH3 | IA-500 | 2-Cl | 3-C(CH3)3 |
IA-501 | 2-Cl | 3-OCH3 | IA-502 | 2-Cl | 3-OCH2CH3 |
IA-503 | 2-Cl | 3-CF3 | IA-504 | 2-Cl | 3-CH(CF3)2 |
IA-505 | 2-Cl | 3-OC(CH3)3 | IA-506 | 2-Cl | 3-CF(CF3)2 |
IA-507 | 2-Cl | 3-OCF3 | IA-508 | 2-Cl | 3-OCHF2 |
IA-509 | 2-Cl | 3-SCF3 | IA-510 | 2-Cl | 3-SO2CF3 |
IA-511 | 2-Cl | 3-CN | IA-512 | 2-Cl | 3-SCH3 |
IA-513 | 2-Cl | 3-SO2CH3 | IA-514 | 2-Cl | 3-OCF2CF3 |
IA-515 | 2-Cl | 3-OCH2CHCH2 | IA-516 | 2-Cl | 3-OCH2CH2OCH3 |
IA-517 | 2-Cl | 3-OCH2CF3 | IA-518 | 2-Cl | 3-OCH2CCH |
IA-519 | 2-Cl | 3-OCH2-环-C3H5 | IA-520 | 2-Cl | 3-C(OH)(CF3)2 |
IA-521 | 2-Br | 3-F | IA-522 | 2-Br | 3-Cl |
IA-523 | 2-Br | 3-Br | IA-524 | 2-Cl | 3-CH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-525 | 2-Br | 3-CH2CH3 | IA-526 | 2-Br | 3-C(CH3)3 |
IA-527 | 2-Br | 3-OCH3 | IA-528 | 2-Br | 3-OCH2CH3 |
IA-529 | 2-Br | 3-CF3 | IA-530 | 2-Br | 3-CH(CF3)2 |
IA-531 | 2-Br | 3-OC(CH3)3 | IA-532 | 2-Br | 3-CF(CF3)2 |
IA-533 | 2-Br | 3-OCF3 | IA-534 | 2-Br | 3-OCHF2 |
IA-535 | 2-Br | 3-SCF3 | IA-536 | 2-Br | 3-SO2CF3 |
IA-537 | 2-Br | 3-CN | IA-538 | 2-Br | 3-SCH3 |
IA-539 | 2-Br | 3-SO2CH3 | IA-540 | 2-Br | 3-OCF2CF3 |
IA-541 | 2-Br | 3-OCH2CHCH2 | IA-542 | 2-Br | 3-OCH2CH2OCH3 |
IA-543 | 2-Br | 3-OCH2CF3 | IA-544 | 2-Br | 3-OCH2CCH |
IA-545 | 2-Br | 3-OCH2-环-C3H5 | IA-546 | 2-Br | 3-C(OH)(CF3)2 |
IA-547 | 2-CH3 | 3-F | IA-548 | 2-CH3 | 3-Cl |
IA-549 | 2-CH3 | 3-Br | IA-550 | 2-CH3 | 3-CH3 |
IA-551 | 2-CH3 | 3-CH2CH3 | IA-552 | 2-CH3 | 3-C(CH3)3 |
IA-553 | 2-CH3 | 3-OCH3 | IA-554 | 2-CH3 | 3-OCH2CH3 |
IA-555 | 2-CH3 | 3-CF3 | IA-556 | 2-CH3 | 3-CH(CF3)2 |
IA-557 | 2-CH3 | 3-OC(CH3)3 | IA-558 | 2-CH3 | 3-CF(CF3)2 |
IA-559 | 2-CH3 | 3-OCF3 | IA-560 | 2-CH3 | 3-OCHF2 |
IA-561 | 2-CH3 | 3-SCF3 | IA-562 | 2-CH3 | 3-SO2CF3 |
IA-563 | 2-CH3 | 3-CN | IA-564 | 2-CH3 | 3-SCH3 |
IA-565 | 2-CH3 | 3-SO2CH3 | IA-566 | 2-CH3 | 3-OCF2CF3 |
IA-567 | 2-CH3 | 3-OCH2CHCH2 | IA-568 | 2-CH3 | 3-OCH2CH2OCH3 |
IA-569 | 2-CH3 | 3-OCH2CF3 | IA-570 | 2-CH3 | 3-OCH2CCH |
IA-571 | 2-CH3 | 3-OCH2-环-C3H5 | IA-572 | 2-CH3 | 3-C(OH)(CF3)2 |
IA-573 | 2-OCH3 | 3-F | IA-574 | 2-OCH3 | 3-Cl |
IA-575 | 2-OCH3 | 3-Br | IA-576 | 2-OCH3 | 3-CH3 |
IA-577 | 2-OCH3 | 3-CH2CH3 | IA-578 | 2-OCH3 | 3-C(CH3)3 |
IA-579 | 2-OCH3 | 3-OCH3 | IA-580 | 2-OCH3 | 3-OCH2CH3 |
IA-581 | 2-OCH3 | 3-CF3 | IA-582 | 2-OCH3 | 3-CH(CF3)2 |
IA-583 | 2-OCH3 | 3-OC(CH3)3 | IA-584 | 2-OCH3 | 3-CF(CF3)2 |
IA-585 | 2-OCH3 | 3-OCF3 | IA-586 | 2-OCH3 | 3-OCHF2 |
IA-587 | 2-OCH3 | 3-SCF3 | IA-588 | 2-OCH3 | 3-SO2CF3 |
IA-589 | 2-OCH3 | 3-CN | IA-590 | 2-OCH3 | 3-SCH3 |
IA-591 | 2-OCH3 | 3-SO2CH3 | IA-592 | 2-OCH3 | 3-OCF2CF3 |
IA-593 | 2-OCH3 | 3-OCH2CHCH2 | IA-594 | 2-OCH3 | 3-OCH2CH2OCH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-595 | 2-OCH3 | 3-OCH2CF3 | IA-596 | 2-OCH3 | 3-OCH2CCH |
IA-597 | 2-OCH3 | 3-OCH2-环-C3H5 | IA-598 | 2-OCH3 | 3-C(OH)(CF3)2 |
IA-599 | 2-CF3 | 3-F | IA-600 | 2-CF3 | 3-Cl |
IA-601 | 2-CF3 | 3-Br | IA-602 | 2-CF3 | 3-CH3 |
IA-603 | 2-CF3 | 3-CH2CH3 | IA-604 | 2-CF3 | 3-C(CH3)3 |
IA-605 | 2-CF3 | 3-OCH3 | IA-606 | 2-CF3 | 3-OCH2CH3 |
IA-607 | 2-CF3 | 3-CF3 | IA-608 | 2-CF3 | 3-CH(CF3)2 |
IA-609 | 2-CF3 | 3-OC(CH3)3 | IA-610 | 2-CF3 | 3-CF(CF3)2 |
IA-611 | 2-CF3 | 3-OCF3 | IA-612 | 2-CF3 | 3-OCHF2 |
IA-613 | 2-CF3 | 3-SCF3 | IA-614 | 2-CF3 | 3-SO2CF3 |
IA-615 | 2-CF3 | 3-CN | IA-616 | 2-CF3 | 3-SCH3 |
IA-617 | 2-CF3 | 3-SO2CH3 | IA-618 | 2-CF3 | 3-OCF2CF3 |
IA-619 | 2-CF3 | 3-OCH2CHCH2 | IA-620 | 2-CF3 | 3-OCH2CH2OCH3 |
IA-621 | 2-CF3 | 3-OCH2CF3 | IA-622 | 2-CF3 | 3-OCH2CCH |
IA-623 | 2-CF3 | 3-OCH2-环-C3H5 | IA-624 | 2-CF3 | 3-C(OH)(CF3)2 |
IA-625 | 2-OCF3 | 3-F | IA-626 | 2-OCF3 | 3-Cl |
IA-627 | 2-OCF3 | 3-Br | IA-628 | 2-OCF3 | 3-CH3 |
IA-629 | 2-OCF3 | 3-CH2CH3 | IA-630 | 2-OCF3 | 3-C(CH3)3 |
IA-631 | 2-OCF3 | 3-OCH3 | IA-632 | 2-OCF3 | 3-OCH2CH3 |
IA-633 | 2-OCF3 | 3-CF3 | IA-634 | 2-OCF3 | 3-CH(CF3)2 |
IA-635 | 2-OCF3 | 3-OC(CH3)3 | IA-636 | 2-OCF3 | 3-CF(CF3)2 |
IA-637 | 2-OCF3 | 3-OCF3 | IA-638 | 2-OCF3 | 3-OCHF2 |
IA-639 | 2-OCF3 | 3-SCF3 | IA-640 | 2-OCF3 | 3-SO2CF3 |
IA-641 | 2-OCF3 | 3-CN | IA-642 | 2-OCF3 | 3-SCH3 |
IA-643 | 2-OCF3 | 3-SO2CH3 | IA-644 | 2-OCF3 | 3-OCF2CF3 |
IA-645 | 2-OCF3 | 3-OCH2CHCH2 | IA-646 | 2-OCF3 | 3-OCH2CH2OCH3 |
IA-647 | 2-OCF3 | 3-OCH2CF3 | IA-648 | 2-OCF3 | 3-OCH2CCH |
IA-649 | 2-OCF3 | 3-OCH2-环-C3H5 | IA-650 | 2-OCF3 | 3-C(OH)(CF3)2 |
IA-651 | 2-SCH3 | 3-F | IA-652 | 2-SCH3 | 3-Cl |
IA-653 | 2-SCH3 | 3-Br | IA-654 | 2-SCH3 | 3-CH3 |
IA-655 | 2-SCH3 | 3-CH2CH3 | IA-656 | 2-SCH3 | 3-C(CH3)3 |
IA-657 | 2-SCH3 | 3-OCH3 | IA-658 | 2-SCH3 | 3-OCH2CH3 |
IA-659 | 2-SCH3 | 3-CF3 | IA-660 | 2-SCH3 | 3-CH(CF3)2 |
IA-661 | 2-SCH3 | 3-OC(CH3)3 | IA-662 | 2-SCH3 | 3-CF(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-663 | 2-SCH3 | 3-OCF3 | IA-664 | 2-SCH3 | 3-OCHF2 |
IA-665 | 2-SCH3 | 3-SCF3 | IA-666 | 2-SCH3 | 3-SO2CF3 |
IA-667 | 2-SCH3 | 3-CN | IA-668 | 2-SCH3 | 3-SCH3 |
IA-669 | 2-SCH3 | 3-SO2CH3 | IA-670 | 2-SCH3 | 3-OCF2CF3 |
IA-671 | 2-SCH3 | 3-OCH2CHCH2 | IA-672 | 2-SCH3 | 3-OCH2CH2OCH3 |
IA-673 | 2-SCH3 | 3-OCH2CF3 | IA-674 | 2-SCH3 | 3-OCH2CCH |
IA-675 | 2-SCH3 | 3-OCH2-环-C3H5 | IA-676 | 2-SCH3 | 3-C(OH)(CF3)2 |
IA-677 | 2-OCHF2 | 3-F | IA-678 | 2-OCHF2 | 3-Cl |
IA-679 | 2-OCHF2 | 3-Br | IA-680 | 2-OCHF2 | 3-CH3 |
IA-681 | 2-OCHF2 | 3-CH2CH3 | IA-682 | 2-OCHF2 | 3-C(CH3)3 |
IA-683 | 2-OCHF2 | 3-OCH3 | IA-684 | 2-OCHF2 | 3-OCH2CH3 |
IA-685 | 2-OCHF2 | 3-CF3 | IA-686 | 2-OCHF2 | 3-CH(CF3)2 |
IA-687 | 2-OCHF2 | 3-OC(CH3)3 | IA-688 | 2-OCHF2 | 3-CF(CF3)2 |
IA-689 | 2-OCHF2 | 3-OCF3 | IA-690 | 2-OCHF2 | 3-OCHF2 |
IA-691 | 2-OCHF2 | 3-SCF3 | IA-692 | 2-OCHF2 | 3-SO2CF3 |
IA-693 | 2-OCHF2 | 3-CN | IA-694 | 2-OCHF2 | 3-SCH3 |
IA-695 | 2-OCHF2 | 3-SO2CH3 | IA-696 | 2-OCHF2 | 3-OCF2CF3 |
IA-697 | 2-OCHF2 | 3-OCH2CHCH2 | IA-698 | 2-OCHF2 | 3-OCH2CH2OCH3 |
IA-699 | 2-OCHF2 | 3-OCH2CF3 | IA-700 | 2-OCHF2 | 3-OCH2CCH |
IA-701 | 2-OCHF2 | 3-OCH2-环-C3H5 | IA-702 | 2-OCHF2 | 3-C(OH)(CF3)2 |
IA-703 | 2-F | 5-F | IA-704 | 2-F | 5-Cl |
IA-705 | 2-F | 5-Br | IA-706 | 2-F | 5-CH3 |
IA-707 | 2-F | 5-CH2CH3 | IA-708 | 2-F | 5-C(CH3)3 |
IA-709 | 2-F | 5-OCH3 | IA-710 | 2-F | 5-OCH2CH3 |
IA-711 | 2-F | 5-CF3 | IA-712 | 2-F | 5-CH(CF3)2 |
IA-713 | 2-F | 5-OC(CH3)3 | IA-714 | 2-F | 5-CF(CF3)2 |
IA-715 | 2-F | 5-OCF3 | IA-716 | 2-F | 5-OCHF2 |
IA-717 | 2-F | 5-SCF3 | IA-718 | 2-F | 5-SO2CF3 |
IA-719 | 2-F | 5-CN | IA-720 | 2-F | 5-SCH3 |
IA-721 | 2-F | 5-SO2CH3 | IA-722 | 2-F | 5-OCF2CF3 |
IA-723 | 2-F | 5-OCH2CHCH2 | IA-724 | 2-F | 5-OCH2CH2OCH3 |
IA-725 | 2-F | 5-OCH2CF3 | IA-726 | 2-F | 5-OCH2CCH |
IA-727 | 2-F | 5-OCH2-环-C3H5 | IA-728 | 2-F | 5-C(OH)(CF3)2 |
IA-729 | 2-Cl | 5-F | IA-730 | 2-Cl | 5-Cl |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-731 | 2-Cl | 5-Br | IA-732 | 2-Cl | 5-CH3 |
IA-733 | 2-Cl | 5-CH2CH3 | IA-734 | 2-Cl | 5-C(CH3)3 |
IA-735 | 2-Cl | 5-OCH3 | IA-736 | 2-Cl | 5-OCH2CH3 |
IA-737 | 2-Cl | 5-CF3 | IA-738 | 2-Cl | 5-CH(CF3)2 |
IA-739 | 2-Cl | 5-OC(CH3)3 | IA-740 | 2-Cl | 5-CF(CF3)2 |
IA-741 | 2-Cl | 5-OCF3 | IA-742 | 2-Cl | 5-OCHF2 |
IA-743 | 2-Cl | 5-SCF3 | IA-744 | 2-Cl | 5-SO2CF3 |
IA-745 | 2-Cl | 5-CN | IA-746 | 2-Cl | 5-SCH3 |
IA-747 | 2-Cl | 5-SO2CH3 | IA-748 | 2-Cl | 5-OCF2CF3 |
IA-749 | 2-Cl | 5-OCH2CHCH2 | IA-750 | 2-Cl | 5-OCH2CH2OCH3 |
IA-751 | 2-Cl | 5-OCH2CF3 | IA-752 | 2-Cl | 5-OCH2CCH |
IA-753 | 2-Cl | 5-OCH2-环-C3H5 | IA-754 | 2-Cl | 5-C(OH)(CF3)2 |
IA-755 | 2-Br | 5-F | IA-756 | 2-Br | 5-Cl |
IA-757 | 2-Br | 5-Br | IA-758 | 2-Cl | 5-CH3 |
IA-759 | 2-Br | 5-CH2CH3 | IA-760 | 2-Br | 5-C(CH3)3 |
IA-761 | 2-Br | 5-OCH3 | IA-762 | 2-Br | 5-OCH2CH3 |
IA-763 | 2-Br | 5-CF3 | IA-764 | 2-Br | 5-CH(CF3)2 |
IA-765 | 2-Br | 5-OC(CH3)3 | IA-766 | 2-Br | 5-CF(CF3)2 |
IA-767 | 2-Br | 5-OCF3 | IA-768 | 2-Br | 5-OCHF2 |
IA-769 | 2-Br | 5-SCF3 | IA-770 | 2-Br | 5-SO2CF3 |
IA-771 | 2-Br | 5-CN | IA-772 | 2-Br | 5-SCH3 |
IA-773 | 2-Br | 5-SO2CH3 | IA-774 | 2-Br | 5-OCF2CF3 |
IA-775 | 2-Br | 5-OCH2CHCH2 | IA-776 | 2-Br | 5-OCH2CH2OCH3 |
IA-777 | 2-Br | 5-OCH2CF3 | IA-778 | 2-Br | 5-OCH2CCH |
IA-779 | 2-Br | 5-OCH2-环-C3H5 | IA-780 | 2-Br | 5-C(OH)(CF3)2 |
IA-781 | 2-CH3 | 5-F | IA-782 | 2-CH3 | 5-Cl |
IA-783 | 2-CH3 | 5-Br | IA-784 | 2-CH3 | 5-CH3 |
IA-785 | 2-CH3 | 5-CH2CH3 | IA-786 | 2-CH3 | 5-C(CH3)3 |
IA-787 | 2-CH3 | 5-OCH3 | IA-788 | 2-CH3 | 5-OCH2CH3 |
IA-789 | 2-CH3 | 5-CF3 | IA-790 | 2-CH3 | 5-CH(CF3)2 |
IA-791 | 2-CH3 | 5-OC(CH3)3 | IA-792 | 2-CH3 | 5-CF(CF3)2 |
IA-793 | 2-CH3 | 5-OCF3 | IA-794 | 2-CH3 | 5-OCHF2 |
IA-795 | 2-CH3 | 5-SCF3 | IA-796 | 2-CH3 | 5-SO2CF3 |
IA-797 | 2-CH3 | 5-CN | IA-798 | 2-CH3 | 5-SCH3 |
IA-799 | 2-CH3 | 5-SO2CH3 | IA-800 | 2-CH3 | 5-OCF2CF3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-801 | 2-CH3 | 5-OCH2CHCH2 | IA-802 | 2-CH3 | 5-OCH2CH2OCH3 |
IA-803 | 2-CH3 | 5-OCH2CF3 | IA-804 | 2-CH3 | 5-OCH2CCH |
IA-805 | 2-CH3 | 5-OCH2-环-C3H5 | IA-806 | 2-CH3 | 5-C(OH)(CF3)2 |
IA-807 | 2-OCH3 | 5-F | IA-808 | 2-OCH3 | 5-Cl |
IA-809 | 2-OCH3 | 5-Br | IA-810 | 2-OCH3 | 5-CH3 |
IA-811 | 2-OCH3 | 5-CH2CH3 | IA-812 | 2-OCH3 | 5-C(CH3)3 |
IA-813 | 2-OCH3 | 5-OCH3 | IA-814 | 2-OCH3 | 5-OCH2CH3 |
IA-815 | 2-OCH3 | 5-CF3 | IA-816 | 2-OCH3 | 5-CH(CF3)2 |
IA-817 | 2-OCH3 | 5-OC(CH3)3 | IA-818 | 2-OCH3 | 5-CF(CF3)2 |
IA-819 | 2-OCH3 | 5-OCF3 | IA-820 | 2-OCH3 | 5-OCHF2 |
IA-821 | 2-OCH3 | 5-SCF3 | IA-822 | 2-OCH3 | 5-SO2CF3 |
IA-823 | 2-OCH3 | 5-CN | IA-824 | 2-OCH3 | 5-SCH3 |
IA-825 | 2-OCH3 | 5-SO2CH3 | IA-826 | 2-OCH3 | 5-OCF2CF3 |
IA-827 | 2-OCH3 | 5-OCH2CHCH2 | IA-828 | 2-OCH3 | 5-OCH2CH2OCH3 |
IA-829 | 2-OCH3 | 5-OCH2CF3 | IA-830 | 2-OCH3 | 5-OCH2CCH |
IA-831 | 2-OCH3 | 5-OCH2-环-C3H5 | IA-832 | 2-OCH3 | 5-C(OH)(CF3)2 |
IA-833 | 2-CF3 | 5-F | IA-834 | 2-CF3 | 5-Cl |
IA-835 | 2-CF3 | 5-Br | IA-836 | 2-CF3 | 5-CH3 |
IA-837 | 2-CF3 | 5-CH2CH3 | IA-838 | 2-CF3 | 5-C(CH3)3 |
IA-839 | 2-CF3 | 5-OCH3 | IA-840 | 2-CF3 | 5-OCH2CH3 |
IA-841 | 2-CF3 | 5-CF3 | IA-842 | 2-CF3 | 5-CH(CF3)2 |
IA-843 | 2-CF3 | 5-OC(CH3)3 | IA-844 | 2-CF3 | 5-CF(CF3)2 |
IA-845 | 2-CF3 | 5-OCF3 | IA-846 | 2-CF3 | 5-OCHF2 |
IA-847 | 2-CF3 | 5-SCF3 | IA-848 | 2-CF3 | 5-SO2CF3 |
IA-849 | 2-CF3 | 5-CN | IA-850 | 2-CF3 | 5-SCH3 |
IA-851 | 2-CF3 | 5-SO2CH3 | IA-852 | 2-CF3 | 5-OCF2CF3 |
IA-853 | 2-CF3 | 5-OCH2CHCH2 | IA-854 | 2-CF3 | 5-OCH2CH2OCH3 |
IA-855 | 2-CF3 | 5-OCH2CF3 | IA-856 | 2-CF3 | 5-OCH2CCH |
IA-857 | 2-CF3 | 5-OCH2-环-C3H5 | IA-858 | 2-CF3 | 5-C(OH)(CF3)2 |
IA-859 | 2-OCF3 | 5-F | IA-860 | 2-OCF3 | 5-Cl |
IA-861 | 2-OCF3 | 5-Br | IA-862 | 2-OCF3 | 5-CH3 |
IA-863 | 2-OCF3 | 5-CH2CH3 | IA-864 | 2-OCF3 | 5-C(CH3)3 |
IA-865 | 2-OCF3 | 5-OCH3 | IA-866 | 2-OCF3 | 5-OCH2CH3 |
IA-867 | 2-OCF3 | 5-CF3 | IA-868 | 2-OCF3 | 5-CH(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-869 | 2-OCF3 | 5-OC(CH3)3 | IA-870 | 2-OCF3 | 5-CF(CF3)2 |
IA-871 | 2-OCF3 | 5-OCF3 | IA-872 | 2-OCF3 | 5-OCHF2 |
IA-873 | 2-OCF3 | 5-SCF3 | IA-874 | 2-OCF3 | 5-SO2CF3 |
IA-875 | 2-OCF3 | 5-CN | IA-876 | 2-OCF3 | 5-SCH3 |
IA-877 | 2-OCF3 | 5-SO2CH3 | IA-878 | 2-OCF3 | 5-OCF2CF3 |
IA-879 | 2-OCF3 | 5-OCH2CHCH2 | IA-880 | 2-OCF3 | 5-OCH2CH2OCH3 |
IA-881 | 2-OCF3 | 5-OCH2CF3 | IA-882 | 2-OCF3 | 5-OCH2CCH |
IA-883 | 2-OCF3 | 5-OCH2-环-C3H5 | IA-884 | 2-OCF3 | 5-C(OH)(CF3)2 |
IA-885 | 2-SCH3 | 5-F | IA-886 | 2-SCH3 | 5-Cl |
IA-887 | 2-SCH3 | 5-Br | IA-888 | 2-SCH3 | 5-CH3 |
IA-889 | 2-SCH3 | 5-CH2CH3 | IA-890 | 2-SCH3 | 5-C(CH3)3 |
IA-891 | 2-SCH3 | 5-OCH3 | IA-892 | 2-SCH3 | 5-OCH2CH3 |
IA-893 | 2-SCH3 | 5-CF3 | IA-894 | 2-SCH3 | 5-CH(CF3)2 |
IA-895 | 2-SCH3 | 5-OC(CH3)3 | IA-896 | 2-SCH3 | 5-CF(CF3)2 |
IA-897 | 2-SCH3 | 5-OCF3 | IA-898 | 2-SCH3 | 5-OCHF2 |
IA-899 | 2-SCH3 | 5-SCF3 | IA-900 | 2-SCH3 | 5-SO2CF3 |
IA-901 | 2-SCH3 | 5-CN | IA-902 | 2-SCH3 | 5-SCH3 |
IA-903 | 2-SCH3 | 5-SO2CH3 | IA-904 | 2-SCH3 | 5-OCF2CF3 |
IA-905 | 2-SCH3 | 5-OCH2CHCH2 | IA-906 | 2-SCH3 | 5-OCH2CH2OCH3 |
IA-907 | 2-SCH3 | 5-OCH2CF3 | IA-908 | 2-SCH3 | 5-OCH2CCH |
IA-909 | 2-SCH3 | 5-OCH2-环-C3H5 | IA-910 | 2-SCH3 | 5-C(OH)(CF3)2 |
IA-911 | 2-OCHF2 | 5-F | IA-912 | 2-OCHF2 | 5-Cl |
IA-913 | 2-OCHF2 | 5-Br | IA-914 | 2-OCHF2 | 5-CH3 |
IA-915 | 2-OCHF2 | 5-CH2CH3 | IA-916 | 2-OCHF2 | 5-C(CH3)3 |
IA-917 | 2-OCHF2 | 5-OCH3 | IA-918 | 2-OCHF2 | 5-OCH2CH3 |
IA-919 | 2-OCHF2 | 5-CF3 | IA-920 | 2-OCHF2 | 5-CH(CF3)2 |
IA-921 | 2-OCHF2 | 5-OC(CH3)3 | IA-922 | 2-OCHF2 | 5-CF(CF3)2 |
IA-923 | 2-OCHF2 | 5-OCF3 | IA-924 | 2-OCHF2 | 5-OCHF2 |
IA-925 | 2-OCHF2 | 5-SCF3 | IA-926 | 2-OCHF2 | 5-SO2CF3 |
IA-927 | 2-OCHF2 | 5-CN | IA-928 | 2-OCHF2 | 5-SCH3 |
IA-929 | 2-OCHF2 | 5-SO2CH3 | IA-930 | 2-OCHF2 | 5-OCF2CF3 |
IA-931 | 2-OCHF2 | 5-OCH2CHCH2 | IA-932 | 2-OCHF2 | 5-OCH2CH2OCH3 |
IA-933 | 2-OCHF2 | 5-OCH2CF3 | IA-934 | 2-OCHF2 | 5-OCH2CCH |
IA-935 | 2-OCHF2 | 5-OCH2-环-C3H5 | IA-936 | 2-OCHF2 | 5-C(OH)(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-937 | 2-CH2CH3 | 5-F | IA-938 | 2-CH2CH3 | 5-Cl |
IA-939 | 2-CH2CH3 | 5-Br | IA-940 | 2-CH2CH3 | 5-CH3 |
IA-941 | 2-CH2CH3 | 5-CH2CH3 | IA-942 | 2-CH2CH3 | 5-C(CH3)3 |
IA-943 | 2-CH2CH3 | 5-OCH3 | IA-944 | 2-CH2CH3 | 5-OCH2CH3 |
IA-945 | 2-CH2CH3 | 5-CF3 | IA-946 | 2-CH2CH3 | 5-CH(CF3)2 |
IA-947 | 2-CH2CH3 | 5-OC(CH3)3 | IA-948 | 2-CH2CH3 | 5-CF(CF3)2 |
IA-949 | 2-CH2CH3 | 5-OCF3 | IA-950 | 2-CH2CH3 | 5-OCHF2 |
IA-951 | 2-CH2CH3 | 5-SCF3 | IA-952 | 2-CH2CH3 | 5-SO2CF3 |
IA-953 | 2-CH2CH3 | 5-CN | IA-954 | 2-CH2CH3 | 5-SCH3 |
IA-955 | 2-CH2CH3 | 5-SO2CH3 | IA-956 | 2-CH2CH3 | 5-OCF2CF3 |
IA-957 | 2-CH2CH3 | 5-OCH2CHCH2 | IA-958 | 2-CH2CH3 | 5-OCH2CH2OCH3 |
IA-959 | 2-CH2CH3 | 5-OCH2CF3 | IA-960 | 2-CH2CH3 | 5-OCH2CCH |
IA-961 | 2-CH2CH3 | 5-OCH2-环-C3H5 | IA-962 | 2-CH2CH3 | 5-C(OH)(CF3)2 |
IA-963 | 2-C(CH3)3 | 5-F | IA-964 | 2-C(CH3)3 | 5-Cl |
IA-965 | 2-C(CH3)3 | 5-Br | IA-966 | 2-C(CH3)3 | 5-CH3 |
IA-967 | 2-C(CH3)3 | 5-CH2CH3 | IA-968 | 2-C(CH3)3 | 5-C(CH3)3 |
IA-969 | 2-C(CH3)3 | 5-OCH3 | IA-970 | 2-C(CH3)3 | 5-OCH2CH3 |
IA-971 | 2-C(CH3)3 | 5-CF3 | IA-972 | 2-C(CH3)3 | 5-CH(CF3)2 |
IA-973 | 2-C(CH3)3 | 5-OC(CH3)3 | IA-974 | 2-C(CH3)3 | 5-CF(CF3)2 |
IA-975 | 2-C(CH3)3 | 5-OCF3 | IA-976 | 2-C(CH3)3 | 5-OCHF2 |
IA-977 | 2-C(CH3)3 | 5-SCF3 | IA-978 | 2-C(CH3)3 | 5-SO2CF3 |
IA-979 | 2-C(CH3)3 | 5-CN | IA-980 | 2-C(CH3)3 | 5-SCH3 |
IA-981 | 2-C(CH3)3 | 5-SO2CH3 | IA-982 | 2-C(CH3)3 | 5-OCF2CF3 |
IA-983 | 2-C(CH3)3 | 5-OCH2CHCH2 | IA-984 | 2-C(CH3)3 | 5-OCH2CH2OCH3 |
IA-985 | 2-C(CH3)3 | 5-OCH2CF3 | IA-986 | 2-C(CH3)3 | 5-OCH2CCH |
IA-987 | 2-C(CH3)3 | 5-OCH2-环-C3H5 | IA-988 | 2-C(CH3)3 | 5-C(OH)(CF3)2 |
IA-989 | 2-OCH2CH3 | 5-F | IA-990 | 2-OCH2CH3 | 5-Cl |
IA-991 | 2-OCH2CH3 | 5-Br | IA-992 | 2-OCH2CH3 | 5-CH3 |
IA-993 | 2-OCH2CH3 | 5-CH2CH3 | IA-994 | 2-OCH2CH3 | 5-C(CH3)3 |
IA-995 | 2-OCH2CH3 | 5-OCH3 | IA-996 | 2-OCH2CH3 | 5-OCH2CH3 |
IA-997 | 2-OCH2CH3 | 5-CF3 | IA-998 | 2-OCH2CH3 | 5-CH(CF3)2 |
IA-999 | 2-OCH2CH3 | 5-OC(CH3)3 | IA-1000 | 2-OCH2CH3 | 5-CF(CF3)2 |
IA-1001 | 2-OCH2CH3 | 5-OCF3 | IA-1002 | 2-OCH2CH3 | 5-OCHF2 |
IA-1003 | 2-OCH2CH3 | 5-SCF3 | IA-1004 | 2-OCH2CH3 | 5-SO2CF3 |
IA-1005 | 2-OCH2CH3 | 5-CN | IA-1006 | 2-OCH2CH3 | 5-SCH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1007 | 2-OCH2CH3 | 5-SO2CH3 | IA-1008 | 2-OCH2CH3 | 5-OCF2CF3 |
IA-1009 | 2-OCH2CH3 | 5-OCH2CHCH2 | IA-1010 | 2-OCH2CH3 | 5-OCH2CH2OCH3 |
IA-1011 | 2-OCH2CH3 | 5-OCH2CF3 | IA-1012 | 2-OCH2CH3 | 5-OCH2CCH |
IA-1013 | 2-OCH2CH3 | 5-OCH2-环-C3H5 | IA-1014 | 2-OCH2CH3 | 5-C(OH)(CF3)2 |
IA-1015 | 2-CH(CF3)2 | 5-F | IA-1016 | 2-CH(CF3)2 | 5-Cl |
IA-1017 | 2-CH(CF3)2 | 5-Br | IA-1018 | 2-CH(CF3)2 | 5-CH3 |
IA-1019 | 2-CH(CF3)2 | 5-CH2CH3 | IA-1020 | 2-CH(CF3)2 | 5-C(CH3)3 |
IA-1021 | 2-CH(CF3)2 | 5-OCH3 | IA-1022 | 2-CH(CF3)2 | 5-OCH2CH3 |
IA-1023 | 2-CH(CF3)2 | 5-CF3 | IA-1024 | 2-CH(CF3)2 | 5-CH(CF3)2 |
IA-1025 | 2-CH(CF3)2 | 5-OC(CH3)3 | IA-1026 | 2-CH(CF3)2 | 5-CF(CF3)2 |
IA-1027 | 2-CH(CF3)2 | 5-OCF3 | IA-1028 | 2-CH(CF3)2 | 5-OCHF2 |
IA-1029 | 2-CH(CF3)2 | 5-SCF3 | IA-1030 | 2-CH(CF3)2 | 5-SO2CF3 |
IA-1031 | 2-CH(CF3)2 | 5-CN | IA-1032 | 2-CH(CF3)2 | 5-SCH3 |
IA-1033 | 2-CH(CF3)2 | 5-SO2CH3 | IA-1034 | 2-CH(CF3)2 | 5-OCF2CF3 |
IA-1035 | 2-CH(CF3)2 | 5-OCH2CHCH2 | IA-1036 | 2-CH(CF3)2 | 5-OCH2CH2OCH3 |
IA-1037 | 2-CH(CF3)2 | 5-OCH2CF3 | IA-1038 | 2-CH(CF3)2 | 5-OCH2CCH |
IA-1039 | 2-CH(CF3)2 | 5-OCH2-环-C3H5 | IA-1040 | 2-CH(CF3)2 | 5-C(OH)(CF3)2 |
IA-1041 | 2-C(OH)(CF3)2 | 5-F | IA-1042 | 2-C(OH)(CF3)2 | 5-Cl |
IA-1043 | 2-C(OH)(CF3)2 | 5-Br | IA-1044 | 2-C(OH)(CF3)2 | 5-CH3 |
IA-1045 | 2-C(OH)(CF3)2 | 5-CH2CH3 | IA-1046 | 2-C(OH)(CF3)2 | 5-C(CH3)3 |
IA-1047 | 2-C(OH)(CF3)2 | 5-OCH3 | IA-1048 | 2-C(OH)(CF3)2 | 5-OCH2CH3 |
IA-1049 | 2-C(OH)(CF3)2 | 5-CF3 | IA-1050 | 2-C(OH)(CF3)2 | 5-CH(CF3)2 |
IA-1051 | 2-C(OH)(CF3)2 | 5-OC(CH3)3 | IA-1052 | 2-C(OH)(CF3)2 | 5-CF(CF3)2 |
IA-1053 | 2-C(OH)(CF3)2 | 5-OCF3 | IA-1054 | 2-C(OH)(CF3)2 | 5-OCHF2 |
IA-1055 | 2-C(OH)(CF3)2 | 5-SCF3 | IA-1056 | 2-C(OH)(CF3)2 | 5-SO2CF3 |
IA-1057 | 2-C(OH)(CF3)2 | 5-CN | IA-1058 | 2-C(OH)(CF3)2 | 5-SCH3 |
IA-1059 | 2-C(OH)(CF3)2 | 5-SO2CH3 | IA-1060 | 2-C(OH)(CF3)2 | 5-OCF2CF3 |
IA-1061 | 2-C(OH)(CF3)2 | 5-OCH2CHCH2 | IA-1062 | 2-C(OH)(CF3)2 | 5-OCH2CH2OCH3 |
IA-1063 | 2-C(OH)(CF3)2 | 5-OCH2CF3 | IA-1064 | 2-C(OH)(CF3)2 | 5-OCH2CCH |
IA-1065 | 2-C(OH)(CF3)2 | 5-OCH2-环-C3H5 | IA-1066 | 2-C(OH)(CF3)2 | 5-C(OH)(CF3)2 |
IA-1067 | 2-CF(CF3)2 | 5-F | IA-1068 | 2-CF(CF3)2 | 5-Cl |
IA-1069 | 2-CF(CF3)2 | 5-Br | IA-1070 | 2-CF(CF3)2 | 5-CH3 |
IA-1071 | 2-CF(CF3)2 | 5-CH2CH3 | IA-1072 | 2-CF(CF3)2 | 5-C(CH3)3 |
IA-1073 | 2-CF(CF3)2 | 5-OCH3 | IA-1074 | 2-CF(CF3)2 | 5-OCH2CH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1075 | 2-CF(CF3)2 | 5-CF3 | IA-1076 | 2-CF(CF3)2 | 5-CH(CF3)2 |
IA-1077 | 2-CF(CF3)2 | 5-OC(CH3)3 | IA-1078 | 2-CF(CF3)2 | 5-CF(CF3)2 |
IA-1079 | 2-CF(CF3)2 | 5-OCF3 | IA-1080 | 2-CF(CF3)2 | 5-OCHF2 |
IA-1081 | 2-CF(CF3)2 | 5-SCF3 | IA-1082 | 2-CF(CF3)2 | 5-SO2CF3 |
IA-1083 | 2-CF(CF3)2 | 5-CN | IA-1084 | 2-CF(CF3)2 | 5-SCH3 |
IA-1085 | 2-CF(CF3)2 | 5-SO2CH3 | IA-1086 | 2-CF(CF3)2 | 5-OCF2CF3 |
IA-1087 | 2-CF(CF3)2 | 5-OCH2CHCH2 | IA-1088 | 2-CF(CF3)2 | 5-OCH2CH2OCH3 |
IA-1089 | 2-CF(CF3)2 | 5-OCH2CF3 | IA-1090 | 2-CF(CF3)2 | 5-OCH2CCH |
IA-1091 | 2-CF(CF3)2 | 5-OCH2-环-C3H5 | IA-1092 | 2-CF(CF3)2 | 5-C(OH)(CF3)2 |
IA-1093 | 2-SCF3 | 5-F | IA-1094 | 2-SCF3 | 5-Cl |
IA-1095 | 2-SCF3 | 5-Br | IA-1096 | 2-SCF3 | 5-CH3 |
IA-1097 | 2-SCF3 | 5-CH2CH3 | IA-1098 | 2-SCF3 | 5-C(CH3)3 |
IA-1099 | 2-SCF3 | 5-OCH3 | IA-1100 | 2-SCF3 | 5-OCH2CH3 |
IA-1101 | 2-SCF3 | 5-CF3 | IA-1102 | 2-SCF3 | 5-CH(CF3)2 |
IA-1103 | 2-SCF3 | 5-OC(CH3)3 | IA-1104 | 2-SCF3 | 5-CF(CF3)2 |
IA-1105 | 2-SCF3 | 5-OCF3 | IA-1106 | 2-SCF3 | 5-OCHF2 |
IA-1107 | 2-SCF3 | 5-SCF3 | IA-1108 | 2-SCF3 | 5-SO2CF3 |
IA-1109 | 2-SCF3 | 5-CN | IA-1110 | 2-SCF3 | 5-SCH3 |
IA-1111 | 2-SCF3 | 5-SO2CH3 | IA-1112 | 2-SCF3 | 5-OCF2CF3 |
IA-1113 | 2-SCF3 | 5-OCH2CHCH2 | IA-1114 | 2-SCF3 | 5-OCH2CH2OCH3 |
IA-1115 | 2-SCF3 | 5-OCH2CF3 | IA-1116 | 2-SCF3 | 5-OCH2CCH |
IA-1117 | 2-SCF3 | 5-OCH2-环-C3H5 | IA-1118 | 2-SCF3 | 5-C(OH)(CF3)2 |
IA-1119 | 2-SO2CF3 | 5-F | IA-1120 | 2-SO2CF3 | 5-Cl |
IA-1121 | 2-SO2CF3 | 5-Br | IA-1122 | 2-SO2CF3 | 5-CH3 |
IA-1123 | 2-SO2CF3 | 5-CH2CH3 | IA-1124 | 2-SO2CF3 | 5-C(CH3)3 |
IA-1125 | 2-SO2CF3 | 5-OCH3 | IA-1126 | 2-SO2CF3 | 5-OCH2CH3 |
IA-1127 | 2-SO2CF3 | 5-CF3 | IA-1128 | 2-SO2CF3 | 5-CH(CF3)2 |
IA-1129 | 2-SO2CF3 | 5-OC(CH3)3 | IA-1130 | 2-SO2CF3 | 5-CF(CF3)2 |
IA-1131 | 2-SO2CF3 | 5-OCF3 | IA-1132 | 2-SO2CF3 | 5-OCHF2 |
IA-1133 | 2-SO2CF3 | 5-SCF3 | IA-1134 | 2-SO2CF3 | 5-SO2CF3 |
IA-1135 | 2-SO2CF3 | 5-CN | IA-1136 | 2-SO2CF3 | 5-SCH3 |
IA-1137 | 2-SO2CF3 | 5-SO2CH3 | IA-1138 | 2-SO2CF3 | 5-OCF2CF3 |
IA-1139 | 2-SO2CF3 | 5-OCH2CHCH2 | IA-1140 | 2-SO2CF3 | 5-OCH2CH2OCH3 |
IA-1141 | 2-SO2CF3 | 5-OCH2CF3 | IA-1142 | 2-SO2CF3 | 5-OCH2CCH |
IA-1143 | 2-SO2CF3 | 5-OCH2-环 | IA-1144 | 2-SO2CF3 | 5-C(OH)(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
-C3H5 | |||||
IA-1145 | 2-SO2CH3 | 5-F | IA-1146 | 2-SO2CH3 | 5-Cl |
IA-1147 | 2-SO2CH3 | 5-Br | IA-1148 | 2-SO2CH3 | 5-CH3 |
IA-1149 | 2-SO2CH3 | 5-CH2CH3 | IA-1150 | 2-SO2CH3 | 5-C(CH3)3 |
IA-1151 | 2-SO2CH3 | 5-OCH3 | IA-1152 | 2-SO2CH3 | 5-OCH2CH3 |
IA-1153 | 2-SO2CH3 | 5-CF3 | IA-1154 | 2-SO2CH3 | 5-CH(CF3)2 |
IA-1155 | 2-SO2CH3 | 5-OC(CH3)3 | IA-1156 | 2-SO2CH3 | 5-CF(CF3)2 |
IA-1157 | 2-SO2CH3 | 5-OCF3 | IA-1158 | 2-SO2CH3 | 5-OCHF2 |
IA-1159 | 2-SO2CH3 | 5-SCF3 | IA-1160 | 2-SO2CH3 | 5-SO2CF3 |
IA-1161 | 2-SO2CH3 | 5-CN | IA-1162 | 2-SO2CH3 | 5-SCH3 |
IA-1163 | 2-SO2CH3 | 5-SO2CH3 | IA-1164 | 2-SO2CH3 | 5-OCF2CF3 |
IA-1165 | 2-SO2CH3 | 5-OCH2CHCH2 | IA-1166 | 2-SO2CH3 | 5-OCH2CH2OCH3 |
IA-1167 | 2-SO2CH3 | 5-OCH2CF3 | IA-1168 | 2-SO2CH3 | 5-OCH2CCH |
IA-1169 | 2-SO2CH3 | 5-OCH2-环-C3H5 | IA-1170 | 2-SO2CH3 | 5-C(OH)(CF3)2 |
IA-1171 | 2-CN | 5-F | IA-1172 | 2-CN | 5-Cl |
IA-1173 | 2-CN | 5-Br | IA-1174 | 2-CN | 5-CH3 |
IA-1175 | 2-CN | 5-CH2CH3 | IA-1176 | 2-CN | 5-C(CH3)3 |
IA-1177 | 2-CN | 5-OCH3 | IA-1178 | 2-CN | 5-OCH2CH3 |
IA-1179 | 2-CN | 5-CF3 | IA-1180 | 2-CN | 5-CH(CF3)2 |
IA-1181 | 2-CN | 5-OC(CH3)3 | IA-1182 | 2-CN | 5-CF(CF3)2 |
IA-1183 | 2-CN | 5-OCF3 | IA-1184 | 2-CN | 5-OCHF2 |
IA-1185 | 2-CN | 5-SCF3 | IA-1186 | 2-CN | 5-SO2CF3 |
IA-1187 | 2-CN | 5-CN | IA-1188 | 2-CN | 5-SCH3 |
IA-1189 | 2-CN | 5-SO2CH3 | IA-1190 | 2-CN | 5-OCF2CF3 |
IA-1191 | 2-CN | 5-OCH2CHCH2 | IA-1192 | 2-CN | 5-OCH2CH2OCH3 |
IA-1193 | 2-CN | 5-OCH2CF3 | IA-1194 | 2-CN | 5-OCH2CCH |
IA-1195 | 2-CN | 5-OCH2-环-C3H5 | IA-1196 | 2-CN | 5-C(OH)(CF3)2 |
IA-1197 | 2-OCF2CF3 | 5-F | IA-1198 | 2-OCF2CF3 | 5-Cl |
IA-1199 | 2-OCF2CF3 | 5-Br | IA-1200 | 2-OCF2CF3 | 5-CH3 |
IA-1201 | 2-OCF2CF3 | 5-CH2CH3 | IA-1202 | 2-OCF2CF3 | 5-C(CH3)3 |
IA-1203 | 2-OCF2CF3 | 5-OCH3 | IA-1204 | 2-OCF2CF3 | 5-OCH2CH3 |
IA-1205 | 2-OCF2CF3 | 5-CF3 | IA-1206 | 2-OCF2CF3 | 5-CH(CF3)2 |
IA-1207 | 2-OCF2CF3 | 5-OC(CH3)3 | IA-1208 | 2-OCF2CF3 | 5-CF(CF3)2 |
IA-1209 | 2-OCF2CF3 | 5-OCF3 | IA-1210 | 2-OCF2CF3 | 5-OCHF2 |
IA-1211 | 2-OCF2CF3 | 5-SCF3 | IA-1212 | 2-OCF2CF3 | 5-SO2CF3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1213 | 2-OCF2CF3 | 5-CN | IA-1214 | 2-OCF2CF3 | 5-SCH3 |
IA-1215 | 2-OCF2CF3 | 5-SO2CH3 | IA-1216 | 2-OCF2CF3 | 5-OCF2CF3 |
IA-1217 | 2-OCF2CF3 | 5-OCH2CHCH2 | IA-1218 | 2-OCF2CF3 | 5-OCH2CH2OCH3 |
IA-1219 | 2-OCF2CF3 | 5-OCH2CF3 | IA-1220 | 2-OCF2CF3 | 5-OCH2CCH |
IA-1221 | 2-OCF2CF3 | 5-OCH2-环-C3H5 | IA-1222 | 2-OCF2CF3 | 5-C(OH)(CF3)2 |
IA-1223 | 2-OCH2CHCH2 | 5-F | IA-1224 | 2-OCH2CHCH2 | 5-Cl |
IA-1225 | 2-OCH2CHCH2 | 5-Br | IA-1226 | 2-OCH2CHCH2 | 5-CH3 |
IA-1227 | 2-OCH2CHCH2 | 5-CH2CH3 | IA-1228 | 2-OCH2CHCH2 | 5-C(CH3)3 |
IA-1229 | 2-OCH2CHCH2 | 5-OCH3 | IA-1230 | 2-OCH2CHCH2 | 5-OCH2CH3 |
IA-1231 | 2-OCH2CHCH2 | 5-CF3 | IA-1232 | 2-OCH2CHCH2 | 5-CH(CF3)2 |
IA-1233 | 2-OCH2CHCH2 | 5-OC(CH3)3 | IA-1234 | 2-OCH2CHCH2 | 5-CF(CF3)2 |
IA-1235 | 2-OCH2CHCH2 | 5-OCF3 | IA-1236 | 2-OCH2CHCH2 | 5-OCHF2 |
IA-1237 | 2-OCH2CHCH2 | 5-SCF3 | IA-1238 | 2-OCH2CHCH2 | 5-SO2CF3 |
IA-1239 | 2-OCH2CHCH2 | 5-CN | IA-1240 | 2-OCH2CHCH2 | 5-SCH3 |
IA-1241 | 2-OCH2CHCH2 | 5-SO2CH3 | IA-1242 | 2-OCH2CHCH2 | 5-OCF2CF3 |
IA-1243 | 2-OCH2CHCH2 | 5-OCH2CHCH2 | IA-1244 | 2-OCH2CHCH2 | 5-OCH2CH2OCH3 |
IA-1245 | 2-OCH2CHCH2 | 5-OCH2CF3 | IA-1246 | 2-OCH2CHCH2 | 5-OCH2CCH |
IA-1247 | 2-OCH2CHCH2 | 5-OCH2-环-C3H5 | IA-1248 | 2-OCH2CHCH2 | 5-C(OH)(CF3)2 |
IA-1249 | 2-OCH2CCH | 5-F | IA-1250 | 2-OCH2CCH | 5-Cl |
IA-1251 | 2-OCH2CCH | 5-Br | IA-1252 | 2-OCH2CCH | 5-CH3 |
IA-1253 | 2-OCH2CCH | 5-CH2CH3 | IA-1254 | 2-OCH2CCH | 5-C(CH3)3 |
IA-1255 | 2-OCH2CCH | 5-OCH3 | IA-1256 | 2-OCH2CCH | 5-OCH2CH3 |
IA-1257 | 2-OCH2CCH | 5-CF3 | IA-1258 | 2-OCH2CCH | 5-CH(CF3)2 |
IA-1259 | 2-OCH2CCH | 5-OC(CH3)3 | IA-1260 | 2-OCH2CCH | 5-CF(CF3)2 |
IA-1261 | 2-OCH2CCH | 5-OCF3 | IA-1262 | 2-OCH2CCH | 5-OCHF2 |
IA-1263 | 2-OCH2CCH | 5-SCF3 | IA-1264 | 2-OCH2CCH | 5-SO2CF3 |
IA-1265 | 2-OCH2CCH | 5-CN | IA-1266 | 2-OCH2CCH | 5-SCH3 |
IA-1267 | 2-OCH2CCH | 5-SO2CH3 | IA-1268 | 2-OCH2CCH | 5-OCF2CF3 |
IA-1269 | 2-OCH2CCH | 5-OCH2CHCH2 | IA-1270 | 2-OCH2CCH | 5-OCH2CH2OCH3 |
IA-1271 | 2-OCH2CCH | 5-OCH2CF3 | IA-1272 | 2-OCH2CCH | 5-OCH2CCH |
IA-1273 | 2-OCH2CCH | 5-OCH2-环-C3H5 | IA-1274 | 2-OCH2CCH | 5-C(OH)(CF3)2 |
IA-1275 | 2-OCH2CF3 | 5-F | IA-1276 | 2-OCH2CF3 | 5-Cl |
IA-1277 | 2-OCH2CF3 | 5-Br | IA-1278 | 2-OCH2CF3 | 5-CH3 |
IA-1279 | 2-OCH2CF3 | 5-CH2CH3 | IA-1280 | 2-OCH2CF3 | 5-C(CH3)3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1281 | 2-OCH2CF3 | 5-OCH3 | IA-1282 | 2-OCH2CF3 | 5-OCH2CH3 |
IA-1283 | 2-OCH2CF3 | 5-CF3 | IA-1284 | 2-OCH2CF3 | 5-CH(CF3)2 |
IA-1285 | 2-OCH2CF3 | 5-OC(CH3)3 | IA-1286 | 2-OCH2CF3 | 5-CF(CF3)2 |
IA-1287 | 2-OCH2CF3 | 5-OCF3 | IA-1288 | 2-OCH2CF3 | 5-OCHF2 |
IA-1289 | 2-OCH2CF3 | 5-SCF3 | IA-1290 | 2-OCH2CF3 | 5-SO2CF3 |
IA-1291 | 2-OCH2CF3 | 5-CN | IA-1292 | 2-OCH2CF3 | 5-SCH3 |
IA-1293 | 2-OCH2CF3 | 5-SO2CH3 | IA-1294 | 2-OCH2CF3 | 5-OCF2CF3 |
IA-1295 | 2-OCH2CF3 | 5-OCH2CHCH2 | IA-1296 | 2-OCH2CF3 | 5-OCH2CH2OCH3 |
IA-1297 | 2-OCH2CF3 | 5-OCH2CF3 | IA-1298 | 2-OCH2CF3 | 5-OCH2CCH |
IA-1299 | 2-OCH2CF3 | 5-OCH2-环-C3H5 | IA-1300 | 2-OCH2CF3 | 5-C(OH)(CF3)2 |
IA-1301 | 2-OCH2CH2-OCH3 | 5-F | IA-1302 | 2-OCH2CH2-OCH3 | 5-Cl |
IA-1303 | 2-OCH2CH2-OCH3 | 5-Br | IA-1304 | 2-OCH2CH2-OCH3 | 5-CH3 |
IA-1305 | 2-OCH2CH2-OCH3 | 5-CH2CH3 | IA-1306 | 2-OCH2CH2-OCH3 | 5-C(CH3)3 |
IA-1307 | 2-OCH2CH2-OCH3 | 5-OCH3 | IA-1308 | 2-OCH2CH2-OCH3 | 5-OCH2CH3 |
IA-1309 | 2-OCH2CH2-OCH3 | 5-CF3 | IA-1310 | 2-OCH2CH2-OCH3 | 5-CH(CF3)2 |
IA-1311 | 2-OCH2CH2-OCH3 | 5-OC(CH3)3 | IA-1312 | 2-OCH2CH2-OCH3 | 5-CF(CF3)2 |
IA-1313 | 2-OCH2CH2-OCH3 | 5-OCF3 | IA-1314 | 2-OCH2CH2-OCH3 | 5-OCHF2 |
IA-1315 | 2-OCH2CH2-OCH3 | 5-SCF3 | IA-1316 | 2-OCH2CH2-OCH3 | 5-SO2CF3 |
IA-1317 | 2-OCH2CH2-OCH3 | 5-CN | IA-1318 | 2-OCH2CH2-OCH3 | 5-SCH3 |
IA-1319 | 2-OCH2CH2-OCH3 | 5-SO2CH3 | IA-1320 | 2-OCH2CH2-OCH3 | 5-OCF2CF3 |
IA-1321 | 2-OCH2CH2-OCH3 | 5-OCH2CHCH2 | IA-1322 | 2-OCH2CH2-OCH3 | 5-OCH2CH2OCH3 |
IA-1323 | 2-OCH2CH2-OCH3 | 5-OCH2CF3 | IA-1324 | 2-OCH2CH2-OCH3 | 5-OCH2CCH |
IA-1325 | 2-OCH2CH2-OCH3 | 5-OCH2-环-C3H5 | IA-1326 | 2-OCH2CH2-OCH3 | 5-C(OH)(CF3)2 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1327 | 2-OC(CH3)3 | 5-F | IA-1328 | 2-OC(CH3)3 | 5-Cl |
IA-1329 | 2-OC(CH3)3 | 5-Br | IA-1330 | 2-OC(CH3)3 | 5-CH3 |
IA-1331 | 2-OC(CH3)3 | 5-CH2CH3 | IA-1332 | 2-OC(CH3)3 | 5-C(CH3)3 |
IA-1333 | 2-OC(CH3)3 | 5-OCH3 | IA-1334 | 2-OC(CH3)3 | 5-OCH2CH3 |
IA-1335 | 2-OC(CH3)3 | 5-CF3 | IA-1336 | 2-OC(CH3)3 | 5-CH(CF3)2 |
IA-1337 | 2-OC(CH3)3 | 5-OC(CH3)3 | IA-1338 | 2-OC(CH3)3 | 5-CF(CF3)2 |
IA-1339 | 2-OC(CH3)3 | 5-OCF3 | IA-1340 | 2-OC(CH3)3 | 5-OCHF2 |
IA-1341 | 2-OC(CH3)3 | 5-SCF3 | IA-1342 | 2-OC(CH3)3 | 5-SO2CF3 |
IA-1343 | 2-OC(CH3)3 | 5-CN | IA-1344 | 2-OC(CH3)3 | 5-SCH3 |
IA-1345 | 2-OC(CH3)3 | 5-SO2CH3 | IA-1346 | 2-OC(CH3)3 | 5-OCF2CF3 |
IA-1347 | 2-OC(CH3)3 | 5-OCH2CHCH2 | IA-1348 | 2-OC(CH3)3 | 5-OCH2CH2OCH3 |
IA-1349 | 2-OC(CH3)3 | 5-OCH2CF3 | IA-1350 | 2-OC(CH3)3 | 5-OCH2CCH |
IA-1351 | 2-OC(CH3)3 | 5-OCH2-环-C3H5 | IA-1352 | 2-OC(CH3)3 | 5-C(OH)(CF3)2 |
IA-1353 | 2-OCH2-环-C3H5 | 5-F | IA-1354 | 2-OCH2-环-C3H5 | 5-Cl |
IA-1355 | 2-OCH2-环-C3H5 | 5-Br | IA-1356 | 2-OCH2-环-C3H5 | 5-CH3 |
IA-1357 | 2-OCH2-环-C3H5 | 5-CH2CH3 | IA-1358 | 2-OCH2-环-C3H5 | 5-C(CH3)3 |
IA-1359 | 2-OCH2-环-C3H5 | 5-OCH3 | IA-1360 | 2-OCH2-环-C3H5 | 5-OCH2CH3 |
IA-1361 | 2-OCH2-环-C3H5 | 5-CF3 | IA-1362 | 2-OCH2-环-C3H5 | 5-CH(CF3)2 |
IA-1363 | 2-OCH2-环-C3H5 | 5-OC(CH3)3 | IA-1364 | 2-OCH2-环-C3H5 | 5-CF(CF3)2 |
IA-1365 | 2-OCH2-环-C3H5 | 5-OCF3 | IA-1366 | 2-OCH2-环-C3H5 | 5-OCHF2 |
IA-1367 | 2-OCH2-环-C3H5 | 5-SCF3 | IA-1368 | 2-OCH2-环-C3H5 | 5-SO2CF3 |
IA-1369 | 2-OCH2-环-C3H5 | 5-CN | IA-1370 | 2-OCH2-环-C3H5 | 5-SCH3 |
IA-1371 | 2-OCH2-环-C3H5 | 5-SO2CH3 | IA-1372 | 2-OCH2-环-C3H5 | 5-OCF2CF3 |
IA-1373 | 2-OCH2-环-C3H5 | 5-OCH2CHCH2 | IA-1374 | 2-OCH2-环-C3H5 | 5-OCH2CH2OCH3 |
IA-1375 | 2-OCH2-环 | 5-OCH2CF3 | IA-1376 | 2-OCH2-环-C3H5 | 5-OCH2CCH |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
-C3H5 | |||||
IA-1377 | 2-OCH2-环-C3H5 | 5-OCH2-环-C3H5 | IA-1378 | 2-OCH2-环-C3H5 | 5-C(OH)(CF3)2 |
IA-1379 | 2-F | 6-F | IA-1380 | 2-F | 6-Cl |
IA-1381 | 2-F | 6-Br | IA-1382 | 2-F | 6-CH3 |
IA-1383 | 2-F | 6-OCH3 | IA-1384 | 2-F | 6-CF3 |
IA-1385 | 2-F | 6-OCF3 | IA-1386 | 2-F | 6-SCH3 |
IA-1387 | 2-F | 6-OCHF2 | IA-1388 | 2-Cl | 6-F |
IA-1389 | 2-Cl | 6-Cl | IA-1390 | 2-Cl | 6-Br |
IA-1391 | 2-Cl | 6-CH3 | IA-1392 | 2-Cl | 6-OCH3 |
IA-1393 | 2-Cl | 6-CF3 | IA-1394 | 2-Cl | 6-OCF3 |
IA-1395 | 2-Cl | 6-SCH3 | IA-1396 | 2-Cl | 6-OCHF2 |
IA-1397 | 2-Br | 6-F | IA-1398 | 2-Br | 6-Cl |
IA-1399 | 2-Br | 6-Br | IA-1400 | 2-Br | 6-CH3 |
IA-1401 | 2-Br | 6-OCH3 | IA-1402 | 2-Br | 6-CF3 |
IA-1403 | 2-Br | 6-OCF3 | IA-1404 | 2-Br | 6-SCH3 |
IA-1405 | 2-Br | 6-OCHF2 | IA-1406 | 2-CH3 | 6-F |
IA-1407 | 2-CH3 | 6-Cl | IA-1408 | 2-CH3 | 6-Br |
IA-1409 | 2-CH3 | 6-CH3 | IA-1410 | 2-CH3 | 6-OCH3 |
IA-1411 | 2-CH3 | 6-CF3 | IA-1412 | 2-CH3 | 6-OCF3 |
IA-1413 | 2-CH3 | 6-SCH3 | IA-1414 | 2-CH3 | 6-OCHF2 |
IA-1415 | 2-OCH3 | 6-F | IA-1416 | 2-OCH3 | 6-Cl |
IA-1417 | 2-OCH3 | 6-Br | IA-1418 | 2-OCH3 | 6-CH3 |
IA-1419 | 2-OCH3 | 6-OCH3 | IA-1420 | 2-OCH3 | 6-CF3 |
IA-1421 | 2-OCH3 | 6-OCF3 | IA-1422 | 2-OCH3 | 6-SCH3 |
IA-1423 | 2-OCH3 | 6-OCHF2 | IA-1424 | 2-CF3 | 6-F |
IA-1425 | 2-CF3 | 6-Cl | IA-1426 | 2-CF3 | 6-Br |
IA-1427 | 2-CF3 | 6-CH3 | IA-1428 | 2-CF3 | 6-OCH3 |
IA-1429 | 2-CF3 | 6-CF3 | IA-1430 | 2-CF3 | 6-OCF3 |
IA-1431 | 2-CF3 | 6-SCH3 | IA-1432 | 2-CF3 | 6-OCHF2 |
IA-1433 | 2-SCH3 | 6-F | IA-1434 | 2-SCH3 | 6-Cl |
IA-1435 | 2-SCH3 | 6-Br | IA-1436 | 2-SCH3 | 6-CH3 |
IA-1437 | 2-SCH3 | 6-OCH3 | IA-1438 | 2-SCH3 | 6-CF3 |
IA-1439 | 2-SCH3 | 6-OCF3 | IA-1440 | 2-SCH3 | 6-SCH3 |
IA-1441 | 2-SCH3 | 6-OCHF2 | IA-1442 | 2-OCF3 | 6-F |
IA-1443 | 2-OCF3 | 6-Cl | IA-1444 | 2-OCF3 | 6-Br |
IA-1445 | 2-OCF3 | 6-CH3 | IA-1446 | 2-OCF3 | 6-OCH3 |
编号* | (R1)m | (R2)n | 编号* | (R1)m | (R2)n |
IA-1447 | 2-OCF3 | 6-CF3 | IA-1448 | 2-OCF3 | 6-OCF3 |
IA-1449 | 2-OCF3 | 6-SCH3 | IA-1450 | 2-OCF3 | 6-OCHF2 |
IA-1451 | 2-OCHF2 | 6-F | IA-1452 | 2-OCHF2 | 6-Cl |
IA-1453 | 2-OCHF2 | 6-Br | IA-1454 | 2-OCHF2 | 6-CH3 |
IA-1455 | 2-OCHF2 | 6-OCH3 | IA-1456 | 2-OCHF2 | 6-CF3 |
IA-1457 | 2-OCHF2 | 6-OCF3 | IA-1458 | 2-OCHF2 | 6-SCH3 |
IA-1459 | 2-OCHF2 | 6-OCHF2 | IA-1460 | 2-Cl | 4-C(CH3)=NOCH3 |
在本发明的式II的中间体中,变量具有如上文对式I化合物所述的相同的优选含义。
式I化合物尤其适于有效对抗以下害虫:
来自鳞翅目的昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotisypsilon)、黄地老虎(Agrotis segetum)、Alabama argillacea、黎豆夜蛾(Anticarsia gemmatalis)、Argyresthia conjugella、Autographa gamma、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、Cirphis unipuncta、苹果小卷蛾(Cydiapomonella)、Dendrolimus pini、Diaphania nitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetriabouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothiszea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantriacunea)、Hyponomeuta malinellus、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostegesticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、Orgyia pseudotsugata、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoeapityocampa、Tortrix viridana、粉纹夜蛾(Trichoplusia ni)和Zeirapheracanadensis,
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、Aphthona euphoridae、Athoushaemorrhoidalis、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、金花金龟(Cetonia aurata)、白菜籽龟象(Ceuthorrhynchusassimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnematibialis)、Conoderus vespertinus、石刁柏负泥虫(Crioceris asparagi)、Ctenicera ssp.、长角叶甲(Diabrotica longicornis)、Diabroticasemipunctata、Diabrotica 12-punctata、南美叶甲(Diabrotica speciosa)、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lema melanopus)、马铃薯叶甲(Leptinotarsadecemlineata)、Limonius californicus、稻水象甲(Lissorhoptrusoryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、梨树叶象(Phyllobius pyri)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia japonica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus granaria),
蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrephaludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anopheles gambiae)、Anophelesfreeborni、海南岛白踝按蚊(Anopheles leucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、螺旋蝇(C ochliomyia hominivorax)、高粱瘿蚊(Contarinia sorghicola)、嗜人瘤蝇蛆(Cordylobia anthropophaga)、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、斑蚊(Culex nigripalpus)、致倦库蚊(Culexquinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culisetamelanura、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia antique、麦地种蝇(Delia coarctata)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum)、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、Geomyza Tripunctata、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates spp.)、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、Leptoconops torrens、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、Mansonia titillanus、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscinastabulans)、羊狂蝇(Oestrus ovis)、Opomyza florum、欧洲麦秆蝇(Oscinellafrit)、天仙子泉蝇(Pegomya hysocyami)、葱蝇(Phorbia antiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbia coarctata)、银足白蛉(Phlebotomusargentipes)、Psorophora columbiae、胡萝卜茎蝇(Psila rosae)、Ps orophora discolor、Prosimulium mixtum、樱桃实蝇(Rhagoletiscerasi)、苹果实蝇(Rhagoletis pomonella)、赤尾麻蝇(Sarcophagahaemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanus lineola)、Tabanus similis、Tipula oleracea和欧洲大蚊(Tipulapaludosa),
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothripscorbetti)、Dichromothrips ssp.、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、金黄异白蚁(Heterotermes aureus)、黄肢散白蚁(Reticulitermesflavipes)、美小黑散白蚁(Reticulitermes virginicus)、欧洲散白蚁(Reticulitermes lucifugus)、Termes natalensis和台湾乳白蚁(Coptotermesformosanus),
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲大蠊(Periplaneta americana)、日本大蠊(Periplaneta japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
真正臭虫(半翅目(Hemiptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesmaquadrata)、Solubea insularis、Thyanta perditor、Acyrthosiphononobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、希奈德蚜(Aphisschneideri)、卷叶蚜(Aphis spiraecola)、接骨木蚜(Aphis sambuci)、豌豆蚜(Acyrthosiphon pisum)、茄无网蚜(Aulacorthum solani)、银叶粉虱(Bemisia argentifolii)、飞廉短尾蚜(Brachycaudus cardui)、李短尾蚜(Brachycaudus helichrysi)、桃短尾蚜(Brachycaudus persicae)、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorushorni、Cerosipha gossypii、草莓中瘤钉毛蚜(Chaetosiphon fragaefolii)、茶镳隐瘤蚜(Cryptomyzus ribis)、高加索冷杉椎球蚜(Dreyfusianordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphisradicola)、Dysaulacorthum pseudosolani、车前圆尾蚜(Dysaphisplantaginea)、梨西圆尾蚜(Dysaphis pyri)、蚕豆微叶蝉(Empoascafabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、巢莱修尾蚜(Megoura viciae)、Melanaphispyrarius、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzus cerasi、李瘤蚜(Myzus varians)、黑茶镳子衲长管蚜(Nasonovia ribis-nigri)、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、苹草缢管蚜(Rhopalosiphum insertum)、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、麦长管蚜(Sitobion avenae)、白粉虱(Trialeurodes vaporariorum)、桔二叉蚜(Toxoptera aurantiiand)、葡萄根瘤蚜(Viteus vitifolii)、温带臭虫(Cimex lectularius)、热带臭虫(Cimexhemipterus)、Reduvius senilis、Triatoma属和Arilus critatus。
蚂蚁、蜜蜂、黄蜂、锯蝇(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athaliarosae)、切叶蚁(Atta cephalotes)、Atta capiguara、Atta laevigata、Attarobusta、Atta sexdens、Atta texana、举腹蚁属(Crematogaster)、Hoplocampa minuta、Hoplocampa testudinea、小黄家蚁(Monomoriumpharaonis)、热带火蚁(Solenopsis geminate)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、红蚂蚁(Pogonomyrmex barbatus)、Pogonomyrmex californicus、Pheidolemegacephala、天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus)、大黄蜂(Vespula squamosa)、Paravespula vulgaris、Paravespulapennsylvanica、Paravespula germanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontusfloridanus和阿根廷蚁(Linepithema humile),
蟋蟀、蚱蜢、蝗虫(直翅目(Orthoptera)),例如居屋艾蟋(Achetadomestica)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、庭疾灶螽(Tachycinesasynamorus)、塞纳加尔小车蝗(Oedaleus senegalensis)、Zonozerusvariegatus、非洲蔗蝗(Hieroglyphus daganensis)、Kraussariaangulifera、意大利蝗(Calliptamus italicus)、澳洲草栖蝗(Chortoicetesterminifera)和褐色拟飞蝗(Locustana pardalina),
蜘蛛纲(Arachnoidea)),如蜘蛛(蜱螨目(Acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、Ambryommamaculatum、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentorsilvarum、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentorvariabilis)、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodesrubicundus、黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus)、Ornithodorus moubata、Ornithodorushermsi、Ornithodorus turicata、柏氏禽刺螨(Ornithonyssus bacoti)、Otobiusmegnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus sanguineus、Rhipicephalus appendiculatus、Rhipicephalusevertsi、人疥螨(Sarcoptes scabiei),瘿螨(Eriophyidae)属,如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨(Tarsonemidae)属,如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨(Tenuipalpidae)属,如紫红短须螨(Brevipalpus phoenicis);叶螨(Tetranychidae)属,如朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychuspacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和草地小爪螨(Oligonychus pratensis);蜘蛛目(Araneida),例如毒蜘蛛(Latrodectusmactans)和褐丝蛛(Loxosceles reclusa),
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),衣鱼、家衣鱼(缨尾目(Thysanura)),例如西洋衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
百足虫(唇足纲(Chilopoda)),例如Scutigera coleoptrata,
千足虫(倍足纲(Diplopoda)),例如Narceus属,
蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicola bovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus,
线虫,尤其是植物寄生线虫如根结线虫,北方根结线虫(Meloidogynehapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogynejavanica)和其它根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globodera rostochiensis)和其它球胞囊(Globodera)属;禾谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其它胞囊线虫(Heterodera)属;种子肿瘿线虫,粒线虫(Anguina)属;茎叶线虫,滑刃线虫(Aphelenchoides)属;刺线虫,杂草刺线虫(Belonolaimus longicaudatus)和其它针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchusxylophilus)和其它伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchusdestructor)、甘薯茎线虫(Ditylenchus dipsaci)和其它茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫,Heliocotylenchus multicinctus和其它Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;冠线虫,Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidorus elongatus和其它长针线虫属(Longidorus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、Pratylenchus goodeyi和其它根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholussimilis)和其它穿孔线虫属(Radopholus);肾形线虫,Rotylenchus robustus和其它盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorusprimitivus和其它毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、Tylenchorhynchus dubius和其它矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);以及其它植物寄生线虫;
配制剂以已知方式制备(对于评论例如参见,US 3,060,084、EP-A 707445(对于液体浓缩物),Browning,"Agglomeration",ChemicalEngineering,1967年12月4日,147-48,Perry's Chemical Engineer'sHandbook,第4版,McGraw-Hill,New York,1963,第8-57页以及下列文献:WO 91/13546、US 4,172,714、US 4,144,050、US 3,920,442、US5,180,587、US 5,232,701、US 5,208,030、GB 2,095,558、US 3,299,566、Klingman,Weed Control as a Science,John Wiley and Sons,Inc.,NewYork,1961,Hance等人,Weed Control Handbook,第8版,BlackwellScientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCH Verlag GmbH,Weinheim(Germany),2001,2.D.A.Knowles,Chemistry and Technology ofAgrochemical Formulations,Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7515-0443-8)),例如通过将活性化合物与适合农业化学品配制剂的助剂如溶剂和/或载体,需要的话乳化剂、表面活性剂和分散剂,防腐剂,消泡剂,防冻剂,以及任选的用于种子处理配制剂的着色剂和粘合剂混合而制备。
合适的溶剂的实例为水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
合适载体的实例为磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐)。
合适的乳化剂的实例为非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)。
分散剂的实例为木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂为木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质为中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮或水。
防冻剂例如甘油、乙二醇、丙二醇的和杀菌剂也可加入配制剂中。
合适的消泡剂例如为基于硅或硬脂酸镁的消泡剂。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或一起研磨来制备。
颗粒如涂敷颗粒、浸渍颗粒和均质颗粒可以通过使活性化合物与固体载体粘附而制备。固体载体实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。此时,活性化合物以90-100重量%,优选95-100重量%的纯度(根据NMR谱)使用。
式I化合物可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;它们应在每种情况下确保本发明活性化合物的最佳精细分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10重量%,优选0.01-1重量%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
以下为配制剂的实例:
1.用水稀释的产品,用于叶面施用。对于种子处理,该产品可经稀释或不经稀释施用于种子。
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。以此方式得到活性化合物含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。由此得到活性化合物含量为20重量%的配制剂。
C)乳油(EC)
将15重量份活性化合物溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。由此得到活性化合物含量为15重量%的配制剂。
D)乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(例如Ultraturrax)将该混合物加入30重量份水中并制成均相乳液。用水稀释得到乳液。由此得到活性化合物含量为25重量%的配制剂。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。由此得到活性化合物含量为20重量%的配制剂。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。由此得到活性化合物含量为50重量%的配制剂。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。由此得到活性化合物含量为75重量%的配制剂。
2.不经稀释而施用的产品,用于叶面施用。对于种子处理,这些产品可经稀释或不经稀释施用于种子。
H)可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的可撒粉产品。
I)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。由此得到活性化合物含量为0.5重量%的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的颗粒。
J)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
可以将各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性成分中,合适的话恰在紧临使用之前(桶混合)加入。这些试剂通常以1:10-10:1的重量比与本发明试剂混合。
式I化合物经由接触与摄取发生作用。
式I化合物也适于保护种子、植物繁殖体和秧苗的根和芽,优选种子防止土壤害虫,且也用于处理由于包括基因工程方法在内的育种而对除草剂或杀真菌剂或杀虫剂作用具有抗性的植物种子。
常规种子处理配制剂例如包括可流动浓缩物FS、溶液LS、用于干燥处理的粉末DS、水分散性粉末WS或用于浆料处理的颗粒、水溶性粉末SS和乳液ES。在播种之前,施用于种子,或者直接施用于种子上。
在植物播种前和植物出苗前,通过对种子进行喷雾或撒粉来进行式I化合物或含有其的配制剂的种子处理施用。
本发明也涉及包含,即涂有和/或含有式I化合物或包含其的组合物的植物繁殖产品,尤其是处理的种子。术语"涂有和/或含有"通常表示在施用时,活性成份大部分在繁殖产品的表面上,尽管取决于施用方法或多或少部分的成份可渗入繁殖产品中。当(再)种植该繁殖产品时,该繁殖产品可吸收活性成份。
种子以0.1g至10kg/100kg种子的量包含本发明化合物或含有其的组合物。
本发明的组合物还可以含有其它活性成分,例如其它农药,杀虫剂,除草剂,肥料如硝酸铵、尿素、钾碱和酸性磷酸盐,植物毒素和植物生长调节剂,安全剂和杀线虫剂。这些额外成分可以与上述组合物依次或结合使用,合适的话还在紧临使用前加入(桶混物)。例如可以在用其它活性成分处理之前或之后用本发明组合物喷雾植物。
可与本发明化合物一起使用的下列农药用来阐述可能的组合,而不施以任何限制:
A.1.有机(硫代)磷酸酯类:高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭克磷(ethoprophos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazophos)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、一六零五(parathion)、甲基一六零五(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、喹恶磷(quinalphos)、sulfotep(sulfotep)、嘧丙磷(tebupirimfos)、硫甲双磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion)
A.2.氨基甲酸酯类:涕灭威(aldicarb)、棉铃威(alanycarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、苯虫威(ethiofencarb)、双氧威(fenoxycarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、特氨叉威(thiofanox)、混杀威(trimethacarb)、二甲威(XMC)、灭杀威(xylylcarb)、唑蚜威(triazamate);
A.3.合成除虫菊酯类:氟锁草醚(acifluorfen)、丙烯除虫菊(allethrin)、d-顺-反丙烯除虫菊、d-反丙烯除虫菊、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊S-环戊烯基(bioallethrin S-cylclopentenyl)、右旋反灭虫菊酯(bioresmethrin)、乙氰菊脂(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯、(RS)氯氟氰菊酯(cyhalothrin)、λ-(RS)氯氟氰菊酯、γ-(RS)氯氟氰菊酯、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、辛体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氯苯菊酯(flumethrin)、T-氟氯苯菊酯(tau-flumethrin)、卤醚菊酯(halfenprox)、咪炔菊酯(imiprothrin)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、灭虫菊(resmethrin)、RU 15525、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin);ZXI8901
A.4.拟保幼激素(juvenile hormone mimics):蒙五一二(hydroprene)、蒙七七七(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb)、蚊蝇醚(pyriproxyfen);
A.5.烟碱受体激动剂/拮抗剂化合物:吡虫清(acetamiprid)、杀虫磺(bensultap)、巴丹(cartap hydrochloride)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、烟碱(nicotine)、艾克敌105(spinosad)(变构激动剂)、噻虫啉(thiacloprid)、硫环杀(thiocyclam)、杀虫双(thiosultap-sodium)和AKD1022。
A.6.GABA门控氯离子通道拮抗剂化合物:氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、acetoprole、乙虫清(ethiprole)、锐劲特(fipronil)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole)、式Γ1的苯基吡唑化合物:
A.7.氯离子通道活化剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin benzoate)、米尔螨素(milbemectin)、lepimectin;
A.8.METI I化合物:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim、鱼藤酮(rotenone);
A.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
A.10.氧化磷酸化去偶剂(Uncoupler):氟唑虫清(chlorfenapyr),二硝甲酚(DNOC);
A.11.氧化磷酸化抑制剂:唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
A.12.蜕皮干扰剂(Moulting disruptor):cryomazine、chromafenozide、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide);
A.13.增效剂:增效醚(piperonyl butoxide)、脱叶磷(tribufos);
A.14.钠通道阻断剂化合物:噁二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
A.15.熏蒸剂:甲基溴、氯化苦(chloropicrin)、磺酰氟(sulfuryl fluoride)
A.16.选择性进食阻断剂(Selective feeding blocker):氟铝酸钠(cryolite)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid);
A.17.螨虫生长抑制剂:四螨嗪(clofentezine)、噻螨酮(hexythiazox)、特苯噁唑(etoxazole);
A.18.甲壳素合成抑制剂:噻嗪酮(buprofezin)、双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);
A.19.类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、spirotetramat;
A.20.章鱼胺激动剂(octapaminergic agonist):虫螨脒(amitraz);
A.21.鱼尼汀(ryanodine)受体调节剂:氟虫酰胺(flubendiamide);
A.22.其它:磷化铝、amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、硼砂、溴螨酯(bromopropylate)、氰化物、cyenopyrafen、丁氟螨酯(cyflumetofen)、灭螨猛(chinomethionate)、开乐散(dicofol)、氟乙酸酯、膦、啶虫丙醚(pyridalyl)、pyrifluquinazon、硫、吐酒石(tartar emetic);
A.23.N-R'-2,2-二halo-1-R"环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙或N-R'-2,2-二(R"')丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)-腙,其中R'为甲基或乙基,halo为氯或溴,R"为氢或甲基且R"'为甲基或乙基;
A.24.邻氨基苯甲酰胺(anthranilamide):chloranthraniliprole,式Γ2化合物:
A.25.丙二腈化合物:CF3(CH2)2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)5CF2H、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)3CF3、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H、CF3CF2CH2C(CN)2CH2(CF2)3CF2H、2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)-丙二腈和CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF2CF3;
A.26.微生物干扰物(disruptor):苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.Israelensi)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subsp.Aizawai)、苏云金芽孢杆菌库斯克亚种(Bacillus thuringiensis subsp.Kurstaki)、苏云金芽胞杆菌拟步行甲亚种(Bacillus thuringiensis subsp.Tenebrionis);
组A的市售化合物可在The Pesticide Manual,第13版,British CropProtection Council(2003)和其它出版物中找到。
式Γ1的硫酰胺及其制备描述于WO 98/28279中。Lepimectin由AgroProject,PJB Publications Ltd,2004年11月已知。Benclothiaz及其制备描述于EP-A1 454621中。杀扑磷和对氧磷及其制备描述于Farm ChemicalsHandbook,第88卷,Meister Publishing Company,2001中。Acetoprole及其制备描述于WO 98/28277中。氰氟虫胺及其制备描述于EP-A1 462 456中。吡氟硫磷描述于Pesticide Science 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备描述于WO 98/45274和US 6335357中。Amidoflumet及其制备描述于US 6221890和JP 21010907中。Flufenerim及其制备描述于WO 03/007717和WO 03/007718中。AKD 1022及其制备描述于US6300348中。chloranthraniliprole描述于WO 01/70671、WO 03/015519和WO 05/118552中。式Γ2的邻氨基苯甲酰胺描述于WO 01/70671、WO04/067528和WO 05/118552中。Cyflumetofen及其制备描述于WO04/080180中。氨基喹唑啉酮化合物pyrifluquinazon描述于EP A 109 7932中。丙二腈化合物CF3(CH2)2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)5CF2H、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)3CF3、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H、CF3CF2CH2C(CN)2CH2(CF2)3CF2H、2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)-丙二腈和CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF2CF3描述于WO 05/63694中。
可以通过使目标寄生虫/害虫、其食物供应源、栖息地、繁殖地或其场所与杀虫有效量的式I化合物或其组合物接触而防治昆虫、螨虫或线虫。
“场所”是指其中害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
“杀虫有效量”通常指对生长获得可观察到的效果所需要活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
本发明化合物或组合物还可以预防性地施用于预期出现害虫的地方。
式I化合物还可以通过使生长的植物与杀虫有效量的式I化合物接触而用于保护植物以免被害虫侵袭或侵染。这里的“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物所在场所)。
在土壤处理或施用于害虫栖息地或巢穴的情况下,活性成分的施用量为0.0001-500g/100m2,优选0.001-20g/100m2。
对于在处理作物植株中的应用,本发明活性成分的施用率可以为0.1-4000g/公顷,理想的是25-600g/公顷,更理想的是50-500g/公顷。
式I化合物和包含它们的组合物还可以用于在包括温血动物(包括人)在内的动物和鱼中防治和预防侵袭和侵染。它们例如适于在哺乳动物如牛、绵羊、猪、骆驼、鹿、马、小猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿和驯鹿,以及产皮动物如貂、灰鼠和浣熊,禽类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和鳗鱼中防治和预防侵袭和侵染。
在温血动物和鱼类中的侵袭包括但不限于虱、叮咬虱、蜱、鼻蝇、羊蜱蝇(keds)、叮咬蝇、家蝇、蝇、蝇蛆幼虫、恙螨、蚋、蚊子和跳蚤。
式I化合物和包含它们的组合物适于内吸和/或非内吸防治体外和/或体内寄生虫。它们对所有或部分发育阶段有效。
可以预防和治疗方式进行给药。活性化合物的给药直接进行或以合适的制剂形式口服、局部/经皮或肠胃外进行。
对于温血动物的口服给药,可以将式I化合物配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,式I化合物可以在其饮用水中给药于动物。对于口服给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天,优选0.5-100mg/kg动物体重/天的式I化合物。
另外,式I化合物可以肠胃外给药于动物,例如通过腔内(intraruminal)、肌内、静脉内或皮下注射。式I化合物可以分散或溶于对于皮下注射而言生理上可接受的载体中。另外,可以将式I化合物配制成皮下给药用植入物。此外,式I化合物可以透皮给药于动物。对于肠胃外给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天的式I化合物。
式I化合物还可以浸洗液、粉剂、粉末、项圈、挂牌(medallions)、喷雾剂、香波、蘸点(spot-on)和喷淋配制剂形式以及以软膏或水包油或油包水乳液局部给药于动物。对于局部施用,浸洗液和喷雾剂通常含有0.5-5,000ppm,优选1-3,000ppm式I化合物。此外,式I化合物可以配制成动物,特别是四足动物如牛和绵羊用耳贴。
合适的制剂是:
-溶液,如口服溶液、稀释后口服给药用浓缩物、用于皮肤上或用于体腔内的溶液、喷淋配制剂、凝胶;
-口服或皮肤给药乳液和悬浮液;半固体制剂;
-其中将活性化合物在软膏基质中或在水包油或油包水乳液基质中加工的配制剂;
-固体制剂如粉末、预混物或浓缩物、颗粒、丸剂、片剂、大丸剂、胶囊;气雾剂和吸入剂,以及含有活性化合物的成型制品。
通常有利的是施用固体配制剂,其以10-300mg/kg,优选20-200mg/kg释放式I化合物。活性化合物还可以与增效剂或防治病原性体内寄生虫和体外寄生虫的其它活性化合物的混合物使用。
通常而言,式I化合物以杀寄生虫有效量施用,“杀寄生虫有效量”指对生长获得可观察到的效果所需的活性成分量,所述效果包括坏死、死亡、阻滞、预防和除去效果,破坏效果或目标生物体的出现和活动降低效果。对于用于本发明的各种化合物/组合物,杀寄生虫有效量可以变化。组合物的杀寄生虫有效量也可以根据盛行的条件如所需杀寄生虫效果和持续时间、目标种类、施用方式等而改变。
合成实施例
通过适当改变起始化合物,使用在以下合成实施例中显示的方案而得到其它化合物I。所得化合物与物理数据一起在下表1中列出。
产物通过偶联高效液相色谱法/质谱法(HPLC/MS),通过在CDCl3或d6-DMSO中的1H-NMR(400MHz)或其熔点来表征。HPLC柱:RP-18柱(来自Merck KgaA,德国的Chromolith Speed ROD)。洗脱:在40℃下,在5分钟内,用5:95-95:5的乙腈+0.1%三氟乙酸(TFA)/水。MS:Quadrupol电喷雾电离,80V(正模式)。
实施例1:2',5'-二氯-联苯基-4-磺酸(喹啉-4-基甲基)-酰胺(I-8)
步骤1:4-溴-N-喹啉-4-基-甲基-苯磺酰胺
将17.99g(70mmol)4-溴苯基-磺酰氯加入于100ml二氯甲烷中的9.29g(58.7mmol)喹啉-4-基-甲胺和8.91g(88.05mmol)三乙胺中,且在20-25℃下,将反应混合物搅拌16小时。加入水、收集沉淀且用水洗涤三次,得到15.9g标题化合物。1H-NMR(400MHz(d6-DMSO):δ[ppm]=8.8(m,1H);8.5(t,1H);8.2-8.0(m,2H);7.8-7.7(m,4H);7.6(m,1H);4.6(d,2H)。
步骤2:2',5'-二氯-联苯基-4-磺酸(喹啉-4-基-甲基)-酰胺(I-8)
将10ml四氢呋喃中的302mg(0.8mmol)4-溴-N-喹啉-4-基-甲基-苯磺酰胺(步骤1)、305mg(1.6mmol)2,5-二氯苯基代硼酸和0.8g(mmol)结合聚合物的四(三苯基膦)钯(0)加热至回流并维持2天,加入300mg N,N-二乙基氨基甲基聚苯乙烯(Nova Biochem,1.8nmol/g),并将混合物再搅拌4小时。过滤、用四氢呋喃洗涤和柱层析(用7:3的环己烷/乙酸乙酯洗脱剂)得到呈固体状的最终产物I-8228mg,熔点为124℃。
实施例2:制备2',4'-二(三氟甲基)联苯基-4-磺酸(8-氯-喹啉-4-基-甲基)-酰胺(I-22)
步骤1:制备8-氯-喹啉-4-甲腈
将Pd(OAc)2(0.28g,1.26mmol)、Na2CO3(2.94g,27.77mmol)、K4[Fe(CN)6]*3H2O(4.69g,11.11mmol)和4,8-二氯-喹啉(5.00g,25.25mmol)悬浮于N,N-二甲基乙酰胺(60ml)中并加热至120℃并维持3天。加入Pd(OAc)2(0.28g,1.26mmol)和K4[Fe(CN)6]*3H2O(2.35g,5.56mmol)并将反应混合物再搅拌8小时。冷却至20℃后,将混合物用乙酸乙酯稀释、过滤并将溶剂蒸发。柱层析纯化(SiO2,石油醚/乙酸乙酯95:5→90:10→80:20)得到8-氯-喹啉-4-甲腈(3.50g),[M+H]+:169.00;保留时间:2.098分钟。
步骤2:制备4-溴-N-(8-氯-喹啉-4-基甲基)苯-磺酰胺
将8-氯-喹啉-4-甲腈(1.50g,7.95mmol)溶解于四氢呋喃(10ml)中并加热至回流。逐滴加入BH3 *二甲硫配合物(0.88ml,8.75mmol)并将反应混合物搅拌1.5小时。冷却至约20℃后,将溶剂蒸发并将残留物溶于四氢呋喃(10ml)中。加入HCl水溶液(20%,5.22g,28.63mmol)并将混合物加热至回流并维持1.5小时。再次除去溶剂并将残留物溶于Et2O(10ml)中。加入NEt3(3.9ml,27.83mmol)并将混合物搅拌10分钟。随后,在0℃下逐滴加入4-溴苯磺酰氯(2.85g,11.13mmol)于Et2O(10ml)中的溶液并将反应混合物搅拌12小时。将混合物倾出并将残留物溶于乙酸乙酯和水中。将有机相分离并经Na2SO4干燥。柱层析纯化(SiO2,环己烷/乙酸乙酯100:0→0:100)得到4-溴-N-(8-氯-喹啉-4-基甲基)苯磺酰胺,熔点:185℃。
步骤3:制备2',4'-二(三氟甲基)联苯基-4-磺酸(8-氯-喹啉-4-基甲基)-酰胺(I-22)
与对实施例1的步骤2所描述的制备程序类似,使0.25g4-溴-N-(8-氯-喹啉-4-基甲基)苯-磺酰胺与0.175g二(三氟甲基)代硼酸反应得到0.15g标题化合物(I-22),熔点为184℃-185℃。
实施例3:制备式VIa和式Va的中间体
步骤1:在0℃下,将5.00g4,6,8-三甲基喹啉(VIe-1)(X=CH3,R5、R7=CH3,R4、R5=H)加入6.55g(0.06mol)叔丁醇钾于100ml四氢呋喃中的溶液中并在该温度下搅拌1.5小时。随后,逐滴加入9.00g(0.08mol)叔丁腈并将混合物搅拌16小时。加入水和甲基叔丁基醚、分离有机层并再次用甲基叔丁基醚萃取水层。
将合并的有机萃取物用盐水洗涤、经Na2SO4干燥并将溶剂蒸发,得到4.4g粗产物VIa-1。1H-NMR(d6-DMSO):δ[ppm]=11.8(s,1H),8.8(m,1H),8.2(s,1H),7.8(m,1H),7.7(m,1H),7.4(m,1H)。
步骤2:在1.1巴下,在4g阮内镍(Raney Nickel)存在下,将来自上述步骤的1.0g(0.005mol)粗产物VIa-1在200ml甲醇中氢化,过滤和蒸发后得到900mg标题化合物V-1。HPLC-MS:MS m/e[M+H+]=187.1,保留时间:1.16分钟。
实施例4:制备8-氟-4-亚甲基氨基喹啉:
步骤1:4-氰基-8-氟-喹啉(VIb-2):
将1.0g(0.0055mol)4-氯-8-氟喹啉、0.68g Na2CO3、0.58g K4[Fe(CN)6]、0.14g Pd-二亚苄基丙酮配合物和0.183g二(二苯基膦基)二茂铁在10ml N-甲基吡咯烷酮中加热至140℃并维持24小时,冷却并用20ml二氯甲烷稀释。过滤并用乙酸乙酯/环己烷=7/3层析得到0.998g 4-氰基-8-氟-喹啉VIb-2。HPLC-MS:m/e[M+H+]=173.0。
步骤2:8-氟-4-亚甲基氨基喹啉(V-2):
在0.06g 10%钯/活性碳和1.5ml饱和氨水存在下,将来自上述步骤的0.5g(0.0029mol)化合物VIb-2在100ml甲醇中氢化20小时,得到85mg胺V-2。
实施例5:制备4-溴-N-(6,8-二甲基-喹啉-4-基甲基)-苯磺酰胺(II-2):
由0.9g(0.005mol)二甲基-喹啉胺V-1、1.23(0.005mol)4-溴-磺酰氯和0.583g(0.0058mol)NEt3获得0.8g呈无色沉淀的标题化合物。1H-NMR:δ[ppm]=9.6(d,1H),8.5(m,1H),7.8-7.6(m,5H),7.4-7.3(m,2H),4.5(d,2H)2.7(s,3H),2.4(s,3H)。
实施例6:制备4-溴-N-(7-氟-喹啉-4-基甲基)-苯磺酰胺(II-3):
由1.23g(0.007mol)7-氟-喹啉胺、1.78g 4-溴-磺酰氯和0.85g(0.008mol)NEt3获得标题化合物。1H-NMR:δ[ppm]=8.8(d,1H),8.6(m,1H),8.2(m,1H),7.7-7.6(m,5H),7.6(m,1H),7.4(m,1H),4.5(d,2H)。
根据类似途径,获得4-溴-N-(7-氯-喹啉-4-基甲基)-苯磺酰胺(II-4),HPLC-MS 412.9 2.65分钟和4-溴-N-(8-氟-喹啉-4-基甲基)-苯磺酰胺(II-5),HPLC-MS:MS m/e[M+H+]=396.9,保留时间=2.67分钟。
实施例7:制备2',4'-二(三氟甲基)联苯基-4-磺酸(1-氧基-喹啉-4-基甲基)-酰胺(I-10的N-氧化物(R1、R2=2,4-(CF3)2,R4至R7为H)):
将50ml乙腈中的0.50g(0.001mol)化合物I-10用0.276g(0.0012mol)间氯过苯甲酸处理并在20-25℃下搅拌过夜。将沉淀滤出,用甲基-叔丁基醚洗涤并在真空中将挥发物除去。将粗产物溶解于50ml二氯甲烷中并用饱和NaHCO3溶液、盐水洗涤两次并经MgSO4干燥以得到157mg标题化合物。HPLC-MS:MS m/e[M+H+]=527.1,保留时间=3.39分钟。
II.评估对动物害虫的活性
1.对墨西哥棉铃象(Boll weevil/Anthonomus grandis)的活性
将活性化合物配制在1:3的DMSO:水中。将10-15个卵放置在被水中的2%琼脂和300ppm福尔马林(formaline)充满的微滴定盘中。用20μl测试溶液喷雾卵,将盘用刺穿箔密封并在24-26℃和75-85%湿度下,在白天/晚上循环下保持3-5天。根据在琼脂表面上的剩余未孵化卵或幼虫和/或由孵化幼虫引起的挖掘通道的量和深度来评估死亡率。重复测试2次。
在该测试中,在2500ppm下,化合物I-1、I-2、I-3、I-4、I-5、I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-19、I-20、I-27、I-28、I-29、I-30、I-33、I-37、I-38、I-39、I-40、I-41、I-42、I-43、I-46和II-5显示至少75%的死亡率。
2.对地中海实蝇(Mediterranean fruitfly/Ceratitis capitata)的活性
将活性化合物配制在1:3的DMSO:水中。将50-80个卵放置在被水中的0.5%琼脂和14%食物充满的微滴定盘中。用5μl测试溶液喷雾卵,将盘用刺穿箔密封并在27-29℃和75-85%湿度下,在荧光灯下保持6天。根据孵化幼虫的敏捷性来评估死亡率。重复测试2次。
在该测试中,在2500ppm下,化合物I-1、I-8、I-10、I-13、I-39和I-42显示至少75%的死亡率。
3.对烟芽夜蛾(Tobacco budworm/Heliothis virescens)的活性
将活性化合物配制在1:3的DMSO:水中。将15-25个卵放置在充满食物的微滴定盘中。用10μl测试溶液喷雾卵,将盘用刺穿箔密封并在27-29℃和75-85%湿度下,在荧光灯下保持6天。根据孵化幼虫的敏捷性和比较进食来评估死亡率。重复测试2次。
在该测试中,在2500ppm下,化合物I-1、I-4、I-6、I-8、I-10、I-13、I-14、I-15、I-17、I-19、I-20、I-35、I-36和I-50显示至少75%的死亡率。
4.对巢菜修尾蚜(Vetch aphid/Megoura viciae)的活性
将活性化合物配制在1:3的DMSO:水中。将豆叶片放置在充满0.8%琼脂和2.5ppm OPUSTM的微滴定盘中。用2.5μl测试溶液喷雾叶片并将5-8个蚜虫成虫放置在微滴定盘中,随后将这些微滴定盘封闭并在22-24℃和35-45%湿度下,在荧光灯下保持6天。根据所繁殖的活蚜虫来评估死亡率。重复测试2次。
在该测试中,在2500ppm下,与未处理对照为0%的死亡率相比,化合物I-1、I-8、I-10、I-14、I-15、I-32、I-46和I-50显示至少75%的死亡率。
5.棉蚜(Cotton aphid/aphis gossypii),混合生命阶段
在处理前,通过将由主蚜虫群落严重侵染的叶子放置在各子叶上,以使子叶阶段的棉花植株受侵染。将蚜虫转移过夜并将宿主叶子移出。随后,将受侵染的子叶在测试溶液中浸渍并搅动3秒钟并使其在通风橱中干燥。将测试植物保持在25℃和20-40%相对湿度和呈24小时光周期的荧光照明下。5天后,相对于在未处理的对照植物上的蚜虫死亡率,测定处理的植物上的蚜虫死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-3、I-4、I-5、I-6、I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-19、I-20、I-21、I-25、I-27、I-28、I-30、I-31、I-32、I-34、I-35、I-36、I-38、I-39、I-45、I-49和I-50显示至少80%的死亡率。
6.亚热带粘虫(Southern Armyworm/spodoptera eridania),第二龄至第三龄幼虫
将活性化合物配制成于35%丙酮和水中的10.000ppm溶液,需要的话将其用水稀释。
将莱豆(Sieva lima bean)叶(展开至第一真叶)在测试溶液中浸渍并搅动3秒钟并随后使其在通风橱中干燥。随后,将经处理的植物放置在25cm穿孔的拉链封闭塑料袋中,加入十只第二龄幼虫并将袋密封。4天后,观察死亡率、植物摄取和对幼虫生长的任何干扰。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-2、I-4、I-6、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-16、I-17、I-18、I-20、I-21、I-22、I-25、I-28、I-31、I-35、I-36、I-38、I-39、I-40、I-42和I-52显示至少80%的死亡率。
7.烟芽夜蛾
将两叶棉花植株用于生物测定。将切离的植物叶子浸渍在活性化合物的1:1丙酮/水稀释液中。叶子干燥后,将其分别放置在培氏培养皿底部上经水湿润的滤纸上。用5-7只幼虫侵染各培养皿并用盖子覆盖。各处理稀释重复4次。将测试培养皿保持在约27℃和60%湿度下。在处理施用后5天,评估各培养皿中活的和病态幼虫的数目并计算百分死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-35、I-36和I-50显示至少80%的死亡率。
8.科罗拉多马铃薯叶甲(Colorado Potato Beetle/Leptinotarsadecemlineata)
将马铃薯植株用于生物测定。将切离的植物叶子浸渍在活性化合物的1:1丙酮/水稀释液中。叶子干燥后,将其分别放置在培氏培养皿底部上经水湿润的滤纸上。用5-7只幼虫侵染各培养皿并用盖子覆盖。各处理稀释重复4次。将测试培养皿保持在约27℃和60%湿度下。在处理施用后5天,评估各培养皿中活的和病态幼虫的数目并计算百分死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-14、I-17、I-18、I-19、I-20、I-21、I-22、I-24、I-25、I-34、I-41、I-42、I-44、I-45和I-52显示至少75%的死亡率。
9.桃蚜(Green Peach Aphid/Myzus persicae)
将活性化合物配制在50:50的丙酮:水和100ppm KineticTM表面活性剂中。
通过将受侵染的叶切片放置在测试植物上而使在第二叶对阶段的胡椒植株(California Wonder品种)被约40只实验室饲养的蚜虫侵染。24小时后,除去叶切片。将完整植物的叶子浸渍在测试化合物的梯度溶液中并使其干燥。将测试植物保持在25℃、20-40%相对湿度和荧光灯(24小时光周期)下。5天后相对于对照植物上的蚜虫死亡率测试在经处理的植物上的蚜虫死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-4、I-6、I-8、I-9、I-10、I-11、I-12、I-14、I-15、I-19、I-20、I-21、I-26和I-31显示至少75%的死亡率。
10.银叶粉虱(Silverleaf whitefly/bemisia argentifolii)
将活性化合物配制在50:50的丙酮:水和100ppm KineticTM表面活性剂中。
使所选择的棉花植株生长至子叶态(每盆一株)。将子叶浸渍在测试溶液中以提供叶的完全覆盖并放置在通风良好的区域中以干燥。将具有经处理的秧苗的各盆放置在塑料杯中并引入10-12只粉虱成虫(大约为3-5日龄)。使用吸气器和与保留吸管尖端连接的0.6cm无毒聚乙烯塑管(Tygontubing)来收集昆虫。随后,将含有所收集的昆虫的尖端缓慢地插入含有经处理的植物的土壤中,使昆虫爬出尖端以到达叶进行进食。将杯子用可再使用的网罩盖(购自Tetko Inc.的150微米网目的聚酯筛PeCap)覆盖。将测试植物在储存室中在约25℃和20-40%相对湿度下保持3天,避免直接曝露于荧光灯(24小时光周期)中以防止热汇集在杯子内部。处理植物后3天评估死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-5、I-7、I-8、I-10、I-11、I-12、I-19、I-20、I-1、I-10和I-45显示至少70%的死亡率。
11.二点叶螨(2-spotted spider mite/tetranychus urticae,抗OP性植株)
将活性化合物配制在50:50的丙酮:水和100ppm KineticTM表面活性剂中。
通过在其上放置取自主群落的受侵染叶子(具有约100只螨虫)各一小片而使具有展开至7-12cm的初生叶的莱豆植物受侵染。这在处理前约2小时进行以使螨虫经由叶片移动至测试植物上产卵。除去用以转移螨虫的叶片。将新侵染的植物浸渍在测试溶液中并使其干燥。将测试植物保持在约25℃,20-40%相对湿度和荧光灯(24小时光周期)下。5天后,移出一片叶子并计算死亡率。
在该测试中,与未处理的对照相比,化合物I-46在300ppm下显示至少70%的死亡率。
12.对豇豆蚜虫(cowpea aphid/aphis craccivora)的活性
将活性化合物配制在50:50的丙酮:水中。记录害虫虫口后,对移植有100-150只各个阶段的蚜虫的盆栽豇豆植株进行喷雾。24小时、72小时和120小时后,记录虫口减少量。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-4、I-5、I-6、I-8、I-9、I-10、I-11、I-12、I-13、I-14、I-15、I-18、I-19、I-20、I-21、I-24、I-24、I-37、I-39、I-42和I-43显示至少80%的死亡率。
13.对菜蛾(diamond back moth/plutella xylostella)的活性
将活性化合物配制在50:50的丙酮:水和0.1体积% Alkamuls EL 620表面活性剂中。将甘蓝菜叶子的6cm叶圆片在测试溶液中浸渍3秒钟并使其在衬有湿润滤纸的皮氏盘中风干。将叶圆片用10只三龄幼虫接种并在25-27℃和50-60%湿度下保持3天。处理72小时后评估死亡率。
在该测试中,与未处理的对照相比,在300ppm下,化合物I-1、I-2、I-4、I-6、I-8、I-10、I-11、I-15、I-19、I-26、I-35、I-36和I-50显示至少75%的死亡率。
14.经由水处理对埃及伊蚊(yellowfever mosquitos/Aedes aegypti)的活性
将测试化合物(在丙酮中的1体积%)施用于在聚苯乙烯6孔塑料板中的9ml蒸馏水中。施用1ppm和10ppm的处理施用率。将1ml蒸馏水中的十只第四龄埃及伊蚊幼虫加入各孔中。将测试培养皿保持在22℃下并每日观察死亡率直至处理后5天。在6个孔中重复各处理。
在该测定中,5天后,化合物I-10在10ppm下产生52%的死亡率。3天后,化合物I-1在1ppm下产生100%死亡率。
15.经由白蚁滤纸诱饵对黄肢散白蚁(eastern subterraneantermites/Reticulitérmes flávipes)的活性。
对丙酮溶液中的4.25cm(直径)滤纸施加毒素处理(0.1重量%和0.3重量%测试化合物)。根据每片滤纸的平均重量106.5mg来计算处理水平(测试化合物%)。调节处理溶液以提供在213ml丙酮中的每片纸需要的毒素量(mg)。对于未处理的对照仅施用丙酮。使经处理的纸通风以蒸发丙酮、用0.25ml水湿润并放置在相应测试器皿(arena)中。
在100×15mm皮氏培养皿(将1茶匙细砂在各培养皿的底部上撒播成薄层)中进行白蚁诱饵生物测定。将另外0.25茶匙砂靠各培养皿的侧边堆放。将砂用2.7ml施用于所堆放的砂的水湿润。需要的话在整个生物测定过程中,将水加入培养皿中以保持高水分含量。生物测定的每个测试培养皿具有一张经处理的滤纸(在砂子上)和30只白蚁工蚁。在3个测试培养皿中重复各处理水平。将测试培养皿在约30℃和85%湿度下保持14天并每日观察死亡率。
在该测定中,14天后,化合物I-10在0.3重量%下产生86%的死亡率。7天后,化合物I-1在0.1重量%下产生99%的死亡率。
16.经由玻璃接触对举尾蚁(acrobat ant/Crematogaster sp.)、家蝇(house fly/Musca domestica)、埃及伊蚊的活性。
用0.44ml活性成份在丙酮中的溶液处理玻璃瓶(20ml闪烁管)。将各瓶打开盖滚动约10分钟以使活性成份完全涂覆在瓶上并使丙酮完全干燥。将六只昆虫或蜱放置在各瓶中,每处理施用率用5个瓶。将瓶保持在22℃下并在各个时间间隔观察处理效果。
在埃及伊蚊玻璃瓶测定中,24小时后,化合物I-10在10ppm下显示100%的死亡率,并48小时后,化合物I-1产生37%的死亡率。
在家蝇玻璃瓶测定中,24小时后,化合物I-10在10ppm下显示80%的死亡率,并48小时后,化合物I-1产生30%的死亡率。
在举尾蚁玻璃瓶测定中,2天后,化合物I-10在100ppm下显示86%的死亡率,并4天后,化合物I-1在100ppm下产生7%的死亡率。
17.经由土壤掺入对举尾蚁和黄肢散白蚁的活性
通过将储备溶液(活性物溶解于丙酮中)加入100g砂壤土中以得到1ppm、10ppm和100ppm的批料来制备土壤。将土壤瓶在瓶滚动器上滚动以充分混合并随后使其通风过夜,使丙酮蒸发掉。
在100×20mm皮氏培养皿中进行蚂蚁生物测定并且生物测定用1%琼脂(7ml)层,随后12.75g干燥处理的土壤准备。将用10%糖溶液浸泡的棉球(#2)加入在微量称量舟中的各培养皿中作为水分和食物来源。随后,用15只举尾蚁工蚁侵染各培养皿。每处理施用率重复三次。每天观察死亡率直至7天,在每次读数时,除去濒死和死亡蚂蚁。
在50×15mm皮氏培养皿中进行黄肢散白蚁生物测定并且生物测定用1%琼脂(2ml)层,随后2g干燥处理的土壤准备。将用1滴蒸馏水湿润的1cm2滤纸片加入各培养皿中作为纤维素食物来源。随后,用15只黄肢散白蚁工蚁侵染各培养皿。每处理施用率重复五次。每天观察死亡率直至7天,在每次读数时,除去濒死和死亡白蚁。
在举尾蚁土壤掺入测定中,3天后,化合物I-10在100ppm下显示100%的死亡率并在7天后,化合物I-1在100ppm下产生36%的死亡率。在白蚁土壤掺入测定中,9天后,化合物1-10在100ppm下显示84%的死亡率,9天后,化合物I-1在100ppm下产生95%的死亡率。
18.兰蓟马(Orchid thrips/dichromothrips corbetti)
用于生物测定的兰蓟马成虫由实验室条件下连续维持的群落获得。为了测试目的,将测试化合物在丙酮:水的1:1混合物加上0.01% Kinetic表面活性剂中稀释成500ppm浓度(化合物重量:稀释剂体积)。
通过使用花卉浸没技术来评估各化合物的蓟马效力。将塑料皮氏培养皿用作测试器皿。将单个完整兰花的所有花瓣浸渍在处理溶液中,经过约3秒钟并使其干燥2小时。将处理的花与10-15只成虫蓟马一起放置在单个皮氏培养皿中。随后,用盖子覆盖皮氏培养皿。将所有测试器皿保持在连续光照和约28℃的温度下并持续整个测定时间。4天后,对各花上和沿各皮氏培养皿内壁的活蓟马数进行计数。由预处理蓟马数外推蓟马死亡水平。
19.对跳甲(flea beetle/Phylotretta striolata)活性
用于生物测定的跳甲成虫由实验室条件下连续维持的群落获得。为测试目的,将测试化合物在丙酮:水的1:1混合物加上0.1% EL 620表面活性剂中稀释成300ppm浓度(化合物重量:稀释剂体积)。
使用唇瓣(lip-dip)浸渍技术来评估各化合物的活性。将衬有湿滤纸的玻璃皮氏培养皿(60×15mm)用作测试器皿。将所有叶圆片浸渍在处理溶液中,经过约3秒钟并使其干燥2小时。将各个处理的叶圆片放置在单个皮氏培养皿中并用10只成虫甲虫接种。随后,用盖子覆盖皮氏培养皿。将所有测试器皿保持在连续光照和约28℃的温度下并持续整个测定时间。3天后,观察死亡率百分数。
在300ppm下,以下化合物显示75%或更高的死亡率:I-32、I-34、I-37、I-42和I-50。
20.对二点黑尾叶蝉(rice green leaf hoppers/Nephotettix virescens)和稻飞虱(brown plant hoppers/Nilaparvata lugens)的活性
用于生物测定的叶蝉和稻飞虱成虫由实验室条件下连续维持的群落获得。为了测试目的,将测试化合物在丙酮:水的1:1混合物加上0.1% EL 620表面活性剂中稀释成300ppm浓度(化合物重量:稀释剂体积)。
使用叶面喷雾技术来评估稻飞虱活性。在施用前,将盆栽稻植株(2-3周龄,品种TN-1)清洁并干燥。在通风橱内使用DeVilbiss雾化器在25psi下,以5ml/株的喷雾体积处理所有植物。为确保喷雾分布均匀,将植物以旋转平台形式放置在通风橱内。随后,将处理植物放置在储存室内并使其干燥2小时。使用聚酯薄膜罩(4英寸直径×19英寸高),将各植物装入罩内并用10只成虫稻飞虱接种。将所有测试植物保持在连续光照和约28℃的温度下并持续整个测定时间。72小时后观察死亡率百分数。
在300ppm下,以下化合物显示对二点黑尾叶蝉的75%或更高的死亡率:I-32。
表I
编号 | (R1)m | (R2)n | (R3)p | R4 | R5 | R6 | R7 | 物理数据(熔点[℃];1H-NMR δ[ppm];MS m/e[M+H+],保留时间[min]) |
I-1 | 2-Cl | 4-Cl | - | H | H | H | H | 181-182;(CDCl3):8.8(m);8.1(m);7.8(m);7.7(m);7.7-7.5(m);7.4-7.2(m);5.3(t);4.7(d).[M+H+]:443.4;保留时间=3.07min |
I-2 | 3-CH3 | 5-CH3 | - | H | H | H | H | 193-194;(CDCl3):8.8(m);8.2(m);7.8(m);7.7-7.6(m);7.6(m);7.3(m),7.2(m);7.1(ps);5.7(t);4.6(d);2.4(s). |
I-3 | 3-OCH3 | 4-OCH3 | - | H | H | H | H | 190-192;(d6DMSO):8.8(m);8.4(s);8.2(psd);8.0(psd);7.9-7.8(m);7.8(m);7.7(m);7.5(m);7.3(m);7.1(m);4.6(s);3.8(s);3.7(s) |
I-4 | 3-F | 4-OCF3 | - | H | H | H | H | 131-132;(d6DMSO):8.8(s);8.5(s);8.2(m);8.0-7.8(m);7.8-7.7(m);7.5(m);7.4(m);4.6(s); |
I-5 | 2-CH3 | 3-CH3 | - | H | H | H | H | 149;(d6DMSO):8.8(m);8.5(s);8.2(m);8.0(m);7.8(m);7.7(m);7.6(m);7.5(m);7.3-7.2(m),7.1(m);4.6(s);2.3(s);2.1(s). |
I-6 | 2-Cl | 4-CF3 | - | H | H | H | H | 160;(d6DMSO):8.8(m); |
编号 | (R1)m | (R2)n | (R3)p | R4 | R5 | R6 | R7 | 物理数据(熔点[℃];1H-NMR δ[ppm];MS m/e[M+H+],保留时间[min]) |
8.1-8.0(m);7.9(m);7.7-7.4(m),7.4-7.3(m);4.6(d). | ||||||||
I-7 | 2-Cl | 3-Cl | - | H | H | H | H | 185;(d8THF):8.8(m);8.1-8.0(m);7.9(m);7.7(m);7.6-7.4(m);4.6(d). |
I-8 | 2-Cl | 5-Cl | - | H | H | H | H | 124;(d6DMSO):8.8(m);8.6(s);8.3(m);8.1-7.6(m);7.4(m);4.6(s). |
I-9 | 2-Cl | 4-OCH3 | - | H | H | H | H | 190;(d6DMSO):8.8(m),8.5(s);8.2(m);8.0(m);7.9(m);7.7(m);7.6-7.5(m);7.4(m),7.3(m),7.2(m),7.0(m);4.6(s);3.8(s). |
I-10 | 2-CF3 | 4-CF3 | - | H | H | H | H | 179;(d6DMSO):8.8(m);8.6(br);8.3-8.1(m),8.0(m);7.9(m);7.8-7.6(m);7.6(m);7.4(m);4.6(s);[M+H+]:511,5;保留时间=3,21min |
I-11 | 2-CF3 | 4-Cl | - | H | H | H | H | 192;(d8THF):8.7(m);8.1-8.0(m);7.9(m);7.8(m),7.7(m);7.5-7.3(m);4.6(m). |
I-12 | 2-CH3 | 4-OCH3 | - | H | H | H | H | 190;(d8THF):8.8(m);8.1-8.0(m);7.9(m);7.7(m);7.6-7.4(m);4.6(d). |
I-13 | 2-CF3 | 5-F | - | H | H | H | H | (d6DMSO):8.8(m);8.6(br);8.1(m);8.1-7.7(m);7.7(m);7.6(m);7.6-7.3(m);4.6(d). |
I-14 | 3-CH3 | 4-Cl | - | H | H | H | H | 162-163;(d8THF):8.8(m);8.1-8.0(m);7.9(m);7.8(m);7.7(m);7.5-7.4(m);7.4(m);7.2(m);4.6(d). |
I-15 | 2-CH3 | 4-Cl | - | H | H | H | H | 134-136;(d8THF):8.8(m); |
编号 | (R1)m | (R2)n | (R3)p | R4 | R5 | R6 | R7 | 物理数据(熔点[℃];1H-NMR δ[ppm];MSm/e[M+H+],保留时间[min]) |
8.1-8.0(m);7.9(m);7.7(m);7.5(m);7.4(m);7.4-7.3(m);7.3(m);7.2(m).4.6(d),2.2(s). | ||||||||
I-16 | 2-OCH3 | 4-Cl | H | H | H | H | 196-197;(d8THF):8.7(m);8.2-8.0(m);7.8(m);7.7-7.6(m);7.5(m);7.4-7.3(m);7.3(t);7.2(s);7.1(m);4.6(d);3.8(s). | |
I-17 | 3-CF3 | 5-CF3 | - | H | H | H | H | 183;(d6DMSO):8.8(m);8.5(br);8.4(pss);8.2(s);8.1(m);8.1-7.9(m);7.7(m);7.6(m);7.4(m,1H),4.6(d) |
I-18 | 2-Cl | 5-CF3 | - | H | H | H | H | (d8THF):8.8(m);8.1-8.0(m);7.9(m);7.8-7.7(m);7.7(m);7.6(m);7.5(m);7.4(m);4.6(s). |
I-19 | 3-F | 4-Cl | - | H | H | H | H | 158-159;(d8THF):8.7(d);8.1-8.0(m);7.9(m);7.8(m);7.7-7.5(m);7.3(m);4.6(s). |
I-20 | 3-CF3 | 4-Cl | - | H | H | H | H | 194-195;(d8THF):8.8(m);8.2(br s);8.1-7.5(m);7.4(m);4.6(s). |
I-21 | 3-Cl | 4-Cl | - | H | H | H | H | 93-98;(d8THF):8.8(m);8.1-8.0(m);7.9(m);7.8(m);7.7-7.6(m);7.5(m);7.4(m).4.6(d). |
I-22 | 2-CF3 | 4-CF3 | - | H | H | H | Cl | 184-185;(d8THF):8.8(m),8.2(br),8.1(m),7.9(m);7.8(m);7.6(m);7.6-7.4(m);4.6(d). |
I-23 | 5-NO2 | 4-Cl | H | H | H | H | 453.9;2.88min |
编号 | (R1)m | (R2)n | (R3)p | R4 | R5 | R6 | R7 | 物理数据(熔点[℃];1H-NMR δ[ppm];MSm/e[M+H+],保留时间[min]) |
I-24 | 2-Cl | 4-Cl | - | H | H | H | Cl | 478.0 |
I-25 | 2-F | 4-Br | - | H | H | H | H | 473.2;3.00min |
I-26 | 2-F | 4-Cl | - | H | H | H | H | 427.3;2.94min |
I-27 | 3-F | 4-OCH2CH3 | - | H | H | H | H | 437.1;2.78min |
I-28 | 3-Cl | 4-OCH3 | - | H | H | H | H | 439.0;2.74min |
I-29 | 3-Cl | 4-O(CH2)2CH3 | - | H | H | H | H | 467.1;3.18min |
I-30 | 2-Cl | 4-OCH2CH3 | - | H | H | H | H | 453.1;2.98min |
I-31 | 2-F | 4-Cl | 5-OCH3 | H | H | H | H | 457.0;2.90min |
I-32 | 2-Cl | 4-CH3 | - | H | H | H | H | 423.1;2.96min |
I-33 | 3-F | 4-OCH3 | - | H | H | H | H | 423.1;2.65min |
I-34 | 2-CH3 | 4-CH3 | - | H | H | H | H | 403.1;2.94min |
I-35 | 2-CH3 | 4-CH3 | 5-CH3 | H | H | H | H | 417.2;3.07min |
I-36 | 2-F | 5-CH3 | - | H | H | H | H | 407.1;2.81min |
I-37 | 3-F | 4-CH3 | - | H | H | H | H | 407.1;2.84min |
I-38 | 3-Cl | 4-CH3 | - | H | H | H | H | 423.1;3.02min |
I-39 | 2-F | 5-Cl | - | H | H | H | H | 427.0;2.81min |
I-40 | 3-CH3 | 4-OCH3 | - | H | H | H | H | 429.5;2.82min |
I-41 | 2-OCH3 | 3-OCH3 | - | H | H | H | H | 435.1;2.52min |
I-42 | 2-F | 5-Br | - | H | H | H | H | 471.0;2.87min |
I-43 | 2-OCH3 | 4-OCH3 | - | H | H | H | H | 435;2.72min |
I-44 | 2-Cl | 4-Cl | - | H | H | Cl | H | 479.0;3.56min |
I-45 | 2-Cl | 4-Cl | - | H | H | H | F | 461.0;3.55min |
I-46 | 2-CH3 | 4-CF(CF3)2 | - | H | H | H | H | 168-169;556.9;3.55min |
I-47 | 2-CF3 | 4-CF3 | - | H | CH3 | H | CH3 | 538.9/3.41 |
I-48 | 2-Cl | 4-Cl | - | H | CH3 | H | CH3 | 470.1/3.31 |
I-49 | 2-Cl | 4-Cl | - | H | H | F | H | 461.4/3.23 |
I-50 | 2-CF3 | 4-CF3 | - | H | H | F | H | 528.9/3.38 |
编号 | (R1)m | (R2)n | (R3)p | R4 | R5 | R6 | R7 | 物理数据(熔点[℃];1H-NMR δ[ppm];MSm/e[M+H+],保留时间[min]) |
I-51 | 2-F | 4-CHO | - | H | H | H | H | 420.9/2.42 |
I-52 | 2-F | 4-CN | - | H | H | H | H | 418.3/2.50 |
I-53 | 2-F | 5-CN | - | H | H | H | H | 418.3/2.47 |
Claims (16)
1.式I的喹啉衍生物:
其中
R1、R2、R3各自独立地为卤素、羟基、氰基、氨基、硝基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C4烷氧基-C1-C4烷氧基、C3-C7环烷基-C1-C4烷氧基、C(OH)(CF3)2、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C(Ra)=O、C(Ra)=NORb、C(=O)ORx或C(=O)NRxRy;
Ra为氢或C1-C4烷基;
Rb为氢、C1-C4烷基、C2-C4链烯基、C2-C4炔基、C1-C4卤代烷基或C2-C4卤代链烯基;
Rx、Ry各自独立地为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷硫基-C1-C4烷基、C1-C4烷基-S(=O)C1-C4烷基、C1-C4烷基-S(=O)2C1-C4烷基、C3-C6环烷基、C1-C4烷基-C3-C6环烷基、C3-C6链烯基、C3-C6炔基;
R4、R5、R6、R7各自独立地为氢、卤素、氰基、氨基、硝基、羟基、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基亚磺酰基、C1-C6卤代烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(=O)ORc;
Rc为氢、C1-C6烷基、C2-C6链烯基或C2-C6炔基;
m和n各自独立地为1、2、3、4或5;
p为0、1、2、3、4或5;
及其N-氧化物、对映异构体、非对映异构体和盐。
2.根据权利要求1的式I的喹啉衍生物,其中
R1、R2、R3各自独立地为卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基或C(Ra)=NORb;
m和n各自独立地为1、2、3、4或5;和
p为0、1、2、3、4或5。
3.根据权利要求1的式I的喹啉衍生物,其中R4、R5、R6、R7各自独立地为氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6卤代烷硫基。
6.如权利要求1-3中任一项所定义的式I化合物在对抗昆虫、螨虫或线虫中的用途。
7.一种通过使昆虫、螨虫或线虫或其食物供应源、栖息地、繁殖地或其场所与杀虫有效量的如权利要求1-3中任一项所定义的式I的化合物或其组合物接触而防治昆虫、螨虫或线虫的方法。
8.一种通过将杀虫有效量的如权利要求1-3中任一项所定义的式I化合物或其组合物施用于植物,或昆虫、螨虫或线虫在其中生长的土壤或水来保护生长中的植物免受昆虫、螨虫或线虫侵袭或侵染的方法。
9.根据权利要求7或8的方法,其中如权利要求1-3中任一项所要求的化合物或包含其的组合物以5-2000g/ha的量施用。
10.一种保护种子的方法,其包括使种子与杀虫有效量的如权利要求1-3中任一项所定义的式I化合物或包含该化合物的组合物接触。
11.根据权利要求10的方法,其中如权利要求1-3中任一项所定义的式I化合物或包含其的组合物以0.1g-10kg/100kg种子的量施用。
12.种子,其以0.1g-10kg/100kg种子的量包含如权利要求1-3中任一项所定义的式I化合物。
13.一种治疗、防治、预防或保护动物免受寄生虫侵染或感染的方法,其包括向动物经口服、局部或肠胃外给药或施用杀寄生虫有效量的如权利要求1-3中任一项所定义的式I化合物或其组合物或其可兽用盐。
14.一种制备用于治疗、防治、预防或保护动物免受寄生虫侵染或感染的组合物的方法,该组合物包含杀寄生虫有效量的如权利要求1-3中任一项所定义的式I化合物或其组合物或其可兽用盐。
15.包含杀虫或杀寄生虫有效量的如权利要求1-3中任一项所定义的式I化合物和可农用或可兽用载体的组合物。
16.协同增效杀虫混合物,其包含如权利要求1-3中任一项所定义的式I化合物和选自下列的农药:有机(硫代)磷酸酯、氨基甲酸酯、合成除虫菊酯、拟保幼激素、烟碱受体激动剂/拮抗剂化合物、GABA门控氯离子通道拮抗剂化合物、氯离子通道活化剂、METI I、II和III化合物、氧化磷酸化去偶剂、氧化磷酸化抑制剂、蜕皮干扰剂、增效剂、钠通道阻断剂化合物、熏蒸剂、选择性进食阻断剂、螨虫生长抑制剂、甲壳素合成抑制剂、类脂生物合成抑制剂、章鱼胺激动剂、鱼尼汀受体调节剂、磷化铝、amidoflumet、benclothiaz、苯螨特、联苯肼酯、硼砂、溴螨酯、氰化物、cyenopyrafen、丁氟螨酯、灭螨猛、开乐散、氟乙酸酯、膦、啶虫丙醚、pyrifluquinazon、硫、吐酒石;N-R′-2,2-二halo-1-R"环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙或N-R′-2,2-二-(R″′)丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙,其中R′为甲基或乙基,halo为氯或溴,R"为氢或甲基且R″′为甲基或乙基,chloranthraniliprole,式Γ2化合物:
CF3(CH2)2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)5CF2H、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H、CF3(CH2)2C(CN)2CH2(CF2)3CF3、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H、CF3CF2CH2C(CN)2CH2(CF2)3CF2H、2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)-丙二腈和CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF2CF3。
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CN103958476A (zh) * | 2011-11-28 | 2014-07-30 | 纳幕尔杜邦公司 | N-(4-喹啉基甲基)磺酰胺衍生物以及它们作为驱肠虫剂的用途 |
US8853339B2 (en) | 2009-08-07 | 2014-10-07 | Bridgestone Corporation | Method for producing copolymer |
CN110301441A (zh) * | 2019-07-09 | 2019-10-08 | 云南大学 | 氯喹防治根结线虫的新用途 |
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CN101247722A (zh) * | 2005-03-16 | 2008-08-20 | 巴斯福股份公司 | 用于对抗节肢动物门害虫的n-(4-吡啶基)甲基磺酰胺 |
WO2007122163A2 (en) * | 2006-04-20 | 2007-11-01 | Basf Se | Pesticidal mixtures |
BRPI0719051A2 (pt) | 2006-11-22 | 2013-11-05 | Basf Se | Compostos de pirimidilmetil-sulfonamida e os n-óxidos, os sais agricolamente aceitáveis e os sais aceitáveis na veterinária dos mesmos, processo para preparar os mesmos, composição agrícola, método para o tratamento de fungos nocivos fitopatogênicos, uso de compostos, seus n-óxidos e seus sais agricolamente aceitáveis e de composições, método para combater pragas de artrópode, e, semente. |
BRPI0820962A2 (pt) * | 2007-12-05 | 2015-07-14 | Basf Se | Compostos, processo para preparar compostos, composição agrícola, método para combater fungos fitopatogênicos nocivos, uso de compostos, e, sementes |
KR101256812B1 (ko) * | 2010-10-18 | 2013-04-22 | 전북대학교산학협력단 | 수도해충에 우수한 살충활성을 지니는 살충제 조성물 |
CN103619818A (zh) | 2011-06-20 | 2014-03-05 | 纳幕尔杜邦公司 | 用于治疗蠕虫感染的杂环化合物 |
WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
CN105473021B (zh) * | 2013-03-15 | 2018-01-19 | 智能专利有限责任公司 | 可穿戴设备及相关系统 |
BR102013031043B1 (pt) | 2013-12-02 | 2018-03-13 | Fundação Butantan | Uso de compostos químicos capazes de inibir a ação tóxica das esfingomielinases d do veneno de aranhas loxosceles e composição farmacêutica compreendendo os referidos compostos |
WO2018169045A1 (ja) * | 2017-03-17 | 2018-09-20 | Meiji Seikaファルマ株式会社 | 中気門亜目ダニ類の防除剤 |
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AU2002226346A1 (en) * | 2000-11-22 | 2002-06-03 | Basf Aktiengesellschaft | 2-aryl-5-trifluoromethylpyridines |
AU2004278095B2 (en) * | 2003-09-18 | 2010-06-24 | Basf Se | 4-piridinylmethylsulphonamide derivatives as fungicidal plant protection agents |
CN101247722A (zh) * | 2005-03-16 | 2008-08-20 | 巴斯福股份公司 | 用于对抗节肢动物门害虫的n-(4-吡啶基)甲基磺酰胺 |
US20080161187A1 (en) * | 2005-03-16 | 2008-07-03 | Basf Aktiengesellschaft | Biphenyl-N-(4-Pyridyl) Methylsulfonamides |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8853339B2 (en) | 2009-08-07 | 2014-10-07 | Bridgestone Corporation | Method for producing copolymer |
CN103958476A (zh) * | 2011-11-28 | 2014-07-30 | 纳幕尔杜邦公司 | N-(4-喹啉基甲基)磺酰胺衍生物以及它们作为驱肠虫剂的用途 |
CN110301441A (zh) * | 2019-07-09 | 2019-10-08 | 云南大学 | 氯喹防治根结线虫的新用途 |
CN110301441B (zh) * | 2019-07-09 | 2021-05-04 | 云南大学 | 氯喹防治根结线虫的新用途 |
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CA2645069A1 (en) | 2007-09-20 |
CR10303A (es) | 2008-12-01 |
MX2008011531A (es) | 2008-09-18 |
MA30377B1 (fr) | 2009-05-04 |
ZA200808722B (en) | 2009-12-30 |
AR063659A1 (es) | 2009-02-11 |
JP2009530239A (ja) | 2009-08-27 |
EA200801895A1 (ru) | 2009-04-28 |
EP2007727A1 (en) | 2008-12-31 |
TW200804286A (en) | 2008-01-16 |
ECSP088808A (es) | 2008-11-27 |
US20090029855A1 (en) | 2009-01-29 |
PE20080006A1 (es) | 2008-04-06 |
BRPI0709582A2 (pt) | 2011-07-19 |
KR20080105159A (ko) | 2008-12-03 |
AP2008004649A0 (en) | 2008-10-31 |
WO2007104726A1 (en) | 2007-09-20 |
AU2007224465A1 (en) | 2007-09-20 |
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