CN101014604A - 6-苯基-7-氨基三唑并嘧啶、其制备方法及其在防治有害真菌中的用途以及包含它们的组合物 - Google Patents
6-苯基-7-氨基三唑并嘧啶、其制备方法及其在防治有害真菌中的用途以及包含它们的组合物 Download PDFInfo
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- CN101014604A CN101014604A CNA2005800301050A CN200580030105A CN101014604A CN 101014604 A CN101014604 A CN 101014604A CN A2005800301050 A CNA2005800301050 A CN A2005800301050A CN 200580030105 A CN200580030105 A CN 200580030105A CN 101014604 A CN101014604 A CN 101014604A
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- 238000000034 method Methods 0.000 title claims description 14
- QYWAEMPKWXJKLS-UHFFFAOYSA-N 6-phenyltriazolo[4,5-d]pyrimidin-7-amine Chemical class C1=NC2=NN=NC2=C(N)N1C1=CC=CC=C1 QYWAEMPKWXJKLS-UHFFFAOYSA-N 0.000 title abstract 2
- 244000053095 fungal pathogen Species 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 131
- 239000001257 hydrogen Substances 0.000 claims abstract description 131
- -1 halocycloalkenyl Chemical group 0.000 claims abstract description 121
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 110
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 51
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 28
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 25
- 239000001301 oxygen Substances 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 5
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 321
- 239000000460 chlorine Substances 0.000 claims description 283
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 155
- 229910052801 chlorine Inorganic materials 0.000 claims description 139
- 239000011737 fluorine Substances 0.000 claims description 63
- 229910052731 fluorine Inorganic materials 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229940084434 fungoid Drugs 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 3
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 3
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 2
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 52
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 17
- 235000013339 cereals Nutrition 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- 241000894006 Bacteria Species 0.000 description 16
- 240000007594 Oryza sativa Species 0.000 description 16
- 235000007164 Oryza sativa Nutrition 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 240000008042 Zea mays Species 0.000 description 13
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
- 235000005822 corn Nutrition 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 229940031815 mycocide Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 150000003851 azoles Chemical class 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000080 wetting agent Substances 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 235000021536 Sugar beet Nutrition 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 235000014787 Vitis vinifera Nutrition 0.000 description 6
- 240000006365 Vitis vinifera Species 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000010410 dusting Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000000160 oxazolidinyl group Chemical group 0.000 description 6
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- 229920000742 Cotton Polymers 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 241000228453 Pyrenophora Species 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
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- 150000003839 salts Chemical class 0.000 description 5
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 3
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 239000010985 leather Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 229920000257 metiram Polymers 0.000 description 1
- HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
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- 239000012875 nonionic emulsifier Substances 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
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- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000007592 spray painting technique Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- YWGZBLRRLREJIR-UHFFFAOYSA-N triazole-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CN=N1 YWGZBLRRLREJIR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(I)的6-苯基-7-氨基三唑并嘧啶,其中各取代基如下所定义:R1为氢、烷基、卤代烷基、环烷基、卤代环烷基、链烯基、卤代链烯基、环烯基、卤代环烯基、炔基、卤代炔基或苯基、萘基,或包含1-4个选自O、N或S的杂原子的5或6员饱和、部分不饱和或芳族杂环;R2为烷基、卤代烷基、环烷基、卤代环烷基、链烯基、卤代链烯基、环烯基、卤代环烯基、炔基、卤代炔基或苯基、萘基,或包含1-4个选自O、N或S的杂原子的5或6员饱和、部分不饱和或芳族杂环;R3、R4、R5、R6、R7为氢或在R2下提到的基团之一,R4还可以与R3或R6一起形成5或6员饱和或不饱和环,该环除了碳原子外还可以另外包含1-3个选自O、N和S的杂原子作为环成员;R2与R3、R4与R5、R6与R7各自可以一起形成可以被1-3个选自O、N和S的杂原子间隔的C2-C5亚烷基、亚链烯基或亚炔基链而形成螺基;p为0或1;L为卤素、烷基、卤代烷基、烷氧基、氰基、硝基、氨基、烷基氨基、二烷基氨基、烷基羰基氨基、C(O)-R、S(O)n-R,其中n为0、1或2;R为氢、烷基、卤代烷基、烷氧基、链烯氧基、炔氧基、氨基、烷基氨基、二烷基氨基;m为1、2、3、4或5;X为卤素、氰基、烷基、烷氧基、链烯氧基、炔氧基或卤代烷氧基,Y为氧或硫;X为氢、烷基、卤代烷基、环烷基、烷基羰基、环烷基羰基、链烯基、卤代链烯基、环烯基、炔基、卤代炔基、苯基、萘基、包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环;或Z与R4或R6一起还可以形成5或6员环,该环除了碳原子和Y以外还可以另外包含1或2个选自O、N和S的杂原子作为环成员;基团R1-R7、X和R可以根据说明书被取代。本发明还涉及生产所述化合物的方法、包含它们的组合物以及它们在防治植物致病性真菌中的用途。
Description
本发明涉及式I的6-苯基-7-氨基三唑并嘧啶:
其中各取代基如下所定义:
R1为氢、C1-C12烷基、C1-C12卤代烷基、C3-C6环烷基、C3-C8卤代环烷基、C2-C12链烯基、C2-C12卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C12炔基、C2-C12卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R2为C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C2-C8链烯基、C2-C8卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C8炔基、C2-C8卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R3、R4、R5、R6、R7为氢或在R2下提到的基团之一;
R4与R3或R6一起还可以形成5或6员饱和或不饱和环,该环除了碳原子外还可以另外包含1-3个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
R2与R3、R4与R5、R6与R7在每种情况下还可以一起为氧而形成羰基以及一起形成可以被1-3个选自O、N和S的杂原子间隔的C2-C5亚烷基或亚链烯基或亚炔基链而形成螺基;
R1-R7在每种情况下可以带有1-4个相同或不同的基团Ra:
Ra为卤素、氰基、硝基、羟基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基羰基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧羰基、C1-C6烷硫基、C1-C6烷基氨基、二C1-C6烷基氨基、C2-C8链烯基、C2-C8卤代链烯基、C3-C8环烯基、C2-C6链烯氧基、C3-C6卤代链烯氧基、C2-C6炔基、C2-C6卤代炔基、C3-C6炔氧基、C3-C6卤代炔氧基、C3-C6环烷氧基、C3-C6环烯氧基、氧基-C1-C3亚烷氧基、苯基、萘基、包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环,
其中这些脂族、脂环族或芳族基团本身可以部分或完全被卤代或可以带有1-3个基团Rb:
Rb为卤素、氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫羰基、烷基、卤代烷基、链烯基、链烯氧基、炔氧基、烷氧基、卤代烷氧基、烷硫基、烷基氨基、二烷基氨基、甲酰基、烷基羰基、烷基磺酰基、烷基次磺酰基(alkylsulfoxyl)、烷氧羰基、烷基羰氧基、烷基氨基羰基、二烷基氨基羰基、烷基氨基硫羰基、二烷基氨基硫羰基,其中这些基团中的烷基包含1-6个碳原子且这些基团中的上述链烯基或炔基包含2-8个碳原子;
和/或带有1-3个下列基团:
环烷基、环烷氧基、杂环基、杂环氧基,其中环状体系包含3-10个环成员;芳基、芳氧基、芳硫基、芳基-C1-C6烷氧基、芳基-C1-C6烷基、杂芳基、杂芳氧基、杂芳硫基,其中芳基优选包含6-10个环成员且杂芳基包含5或6个环成员,其中环状体系可以部分或完全被卤代或可以被烷基或卤代烷基取代;
p为0或1;
L为卤素、C1-C4烷基、C1-C2卤代烷基、C1-C4烷氧基、氰基、硝基、氨基、C1-C4烷基氨基、二(C1-C4)烷基氨基、C1-C4烷基羰基氨基、C(O)-R、S(O)n-R;
R为氢、C1-C4烷基、C1-C2卤代烷基、C1-C4烷氧基、C2-C4链烯氧基、C2-C4炔氧基、氨基、C1-C4烷基氨基、二(C1-C4)烷基氨基;其中基团R可以被1-3个基团Rb取代;
n为0、1或2;
m为1、2、3、4或5;
X为卤素、氰基、C1-C4烷基、C1-C4烷氧基、C2-C4链烯氧基、C2-C4炔氧基或C1-C2卤代烷氧基,
Y为氧或硫;
Z为氢、C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C8烷基羰基、C1-C8烷氧羰基、(C=O)NRARB、C3-C8链烯氧羰基、C3-C8炔氧羰基、C3-C6环烷基羰基、C2-C8链烯基、C2-C8卤代链烯基、C3-C8环烯基、C2-C6炔基、C2-C6卤代炔基、C3-C6环烷氧羰基、C3-C6环烯氧羰基、C1-C8烷基亚磺酰基、C1-C8烷硫基、C1-C8烷基磺酰基、苯基、萘基、包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环;或
Z与R5或R7一起还可以形成5或6员饱和或不饱和环,该环除了碳原子和Y以外还可以另外包含1或2个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
基团Z可以部分或完全被卤代或带有1-3个基团Rb;
RA、RB独立地为氢、C1-C8烷基、C2-C8链烯基、C2-C8炔基、C3-C6环烷基或C3-C6环烯基;
RA和RB可以与它们所连接的氮原子一起形成5或6员饱和、部分不饱和或芳族环,该环除了碳原子外还可以包含1-3个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra。
此外,本发明涉及制备这些化合物的方法和中间体、包含它们的组合物及其在防治植物病原性有害真菌中的用途。
6-苯基-7-氨基三唑并嘧啶以一般方式由EP-A 71792已知。具有包含羟基或醚基的7-氨基取代基的6-苯基-7-氨基三唑并嘧啶公开于EP-A 550113、US 5 993 996、US 6 117 865、US 6 297 251和WO 98/46607中。已知这些化合物适于防治有害真菌。
本发明化合物与上述申请所公开的化合物的不同在于7-氨基的具体实施方案,其在α-碳原子上是支化的。
在许多情况下,已知化合物的活性并不令人满意。基于此,本发明的目的是提供具有改进活性和/或更宽活性谱的化合物。
我们发现这由开头所定义的化合物实现。此外,我们还发现了它们的制备方法和中间体、包含它们的组合物和使用化合物I防治有害真菌的方法。
本发明化合物可以通过不同途径得到。有利的是它们通过使式II的7-二卤代三唑并嘧啶与其中各变量如对式I所定义的式III的胺反应而制备。
该反应有利地在0-70℃,优选10-35℃下,优选在惰性溶剂如醚类,例如二烷、乙醚或尤其是四氢呋喃,卤代烃如二氯甲烷,或芳烃如甲苯存在下进行[参见WO-A 98/46608]。
优选使用碱,如叔胺,例如三乙胺或无机胺,如碳酸钾;还可以将过量的式III胺用作碱。
通过使用由EP-A 550 113和EP-A 770 615已知的5,7-二卤代三唑并嘧啶,因此可以得到其中X为卤素,优选氯的式I的5-卤代三唑并嘧啶。它们形成本发明的优选主题。其他5,7-二卤代三唑并嘧啶可以类似于所引用的文献得到。
取决于式I中基团Z的实施方案,可能有利的是使II与合适的式IIIa的羟基胺或巯基胺(Z=氢)反应并在形成的式Ia的7-羟基-或7-巯基氨基三唑并嘧啶阶段通过醚化或酯化引入基团Z。
为此,使式Ia的7-羟基-或7-巯基氨基三唑并嘧啶与烷基化或酰基化试剂Z-L反应,其中L为可亲核置换的基团。本领域熟练技术人员通常熟知适于醚化或酯化的反应条件[参见Organikum,VEB Deutscher Verlagder Wissenschaften,Berlin(1981)]。
式III和IIIa的胺由文献已知、可以通过已知方法制备或可以市购。
其中X为氰基、C1-C6烷氧基或C1-C2卤代烷氧基的式I化合物可以有利方式通过使其中X为卤素,优选氯的化合物I与化合物M-X’(式IV)反应而得到。取决于要引入的X’的含义,化合物IV为无机氰化物、醇盐或卤代醇盐。该反应有利地在惰性溶剂存在下进行。式IV中的阳离子M不太重要;出于实际的原因,通常优选铵、四烷基铵或碱金属或碱土金属盐。
I(X=卤素)+M-X′ → I(X=X′)
IV
反应温度通常为0-120℃,优选10-40℃[参见J.Heterocycl.Chem.,12,(1975),861-863]。
合适的溶剂包括醚类,如二烷、乙醚和优选四氢呋喃,卤代烃类如二氯甲烷和芳烃类如甲苯。
其中X为C1-C4烷基的式I化合物可以经由下列合成途径以有利方式得到:
其中X1为C1-C4烷基或C1-C4卤代烷基的5-烷基-7-卤代三唑并嘧啶与胺III或IIIa的反应在上面进一步描述的条件下进行。式V化合物由WO03/093271已知或可以按照所引用的文献制备。
或者还可以由其中X尤其为氯的化合物I和式VI的丙二酸酯制备其中X为C1-C4烷基的式I化合物。在式VI中,X”为氢或C1-C3烷基且R为C1-C4烷基。将它们转化成式VII化合物并脱羧得到化合物I[参见US5,994,360]。
丙二酸酯VI由文献已知[J.Am.Chem.Soc.,
64(1942),2714;J.Org.Chem.,
39(1974),2172;Helv.Chim.Acta,
61(1978),1565],或者它们可以按照所引用的文献制备。
酯VII的随后水解在通常为常规的条件下进行;取决于各种结构单元,化合物VII的碱或酸性水解可能是有利的。在酯水解的条件下,可能已经完全或部分脱羧成I。
脱羧通常在20-180℃,优选50-120℃的温度下在惰性溶剂中,合适的话在酸存在下进行。
合适的酸是盐酸、硫酸、磷酸、甲酸、乙酸、对甲苯磺酸。合适的溶剂是水,脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如乙醚、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,腈如乙腈和丙腈,酮如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺;特别优选该反应在盐酸或乙酸中进行。还可以使用所述溶剂的混合物。
其中X为C1-C4烷基的式I化合物还可以通过将式I的5-卤代三唑并嘧啶与式VIII的有机金属试剂偶联而得到。在该方法的一个实施方案中,该反应在过渡金属催化如Ni或Pd催化下进行。
I(X=Hal)+My(-X″)y → I(X=C1-C4烷基)
VllI
在式VIII中,M为Y价金属离子,如B、Zn或Sn,且X″为C1-C3烷基。该反应例如可以类似于下列方法进行:J.Chem.Soc.Perkin Trans.1(1994),1187,同上,1(1996),2345;WO 99/41255;Aust.J.Chem.,
43(1990),733;J.Org.Chem.,
43(1978),358;J.Chem.Soc.Chem.Commun.(1979),866;Tetrahedron Lett.,
34(1993),8267;同上,
33(1992),413。
以常规方式后处理反应混合物,例如通过与水混合、分离各相并且合适的话层析提纯粗产物。某些中间体和终产物以无色或浅棕色粘稠油形式得到,它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则还可以通过重结晶或浸煮进行提纯。
若个别化合物I不能通过上述途径获得,则可以通过衍生其它化合物I而制备它们。
若合成得到异构体的混合物,则通常不必进行分离,因为在某些情况下各异构体可以在为了应用的后处理过程中或在施用过程中(例如在光、酸或碱的作用下)相互转化。这类转化也可以在使用后发生,例如在处理植物时,在处理的植物中或在待防治的有害真菌中。
在上式所给符号的定义中,使用通常为下列取代基的代表的集合性术语:
卤素:氟、氯、溴和碘;
烷基:具有1-4、1-6或1-8个碳原子的饱和直链或支化烃基,例如C1-C6烷基,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;
卤代烷基:具有1-2、1-4或1-6个碳原子的直链或支化烷基(如上所述),
其中这些基团中的部分或所有氢原子可以被上述卤原子替代;尤其是C1-C2卤代烷基,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-溴乙基、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、五氟乙基或1,1,1-三氟丙-2-基;
链烯基:具有2-4、2-6或2-8个碳原子和一根或两根在任意位置的双键的
不饱和直链或支化烃基,例如C2-C6链烯基,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;
卤代链烯基:具有2-8个碳原子和一根或两根在任意位置的双键的不饱和直链或支化烃基(如上所述),其中这些基团中的部分或所有氢原子可以被上述卤原子,尤其是氟、氯和溴替代;
炔基:具有2-4、2-6或2-8个碳原子和一根或两根在任意位置的叁键的直链或支化烃基,例如C2-C6炔基,如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基;
环烷基:具有3-6或3-8个碳环成员的单环或双环饱和烃基,例如C3-C8环烷基,如环丙基、环丁基、环戊基、环己基、环庚基和环辛基;包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环:
-含有1-3个氮原子和/或1个氧或硫原子或1或2个氧和/或硫原子的5或6员杂环基,例如2-四氢呋喃基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、2-吡咯烷基、3-吡咯烷基、3-异唑烷基、4-异唑烷基、5-异唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-唑烷基、4-唑烷基、5-唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、2-咪唑烷基、4-咪唑烷基、2-吡咯啉-2-基、2-吡咯啉-3-基、3-吡咯啉-2-基、3-吡咯啉-3-基、2-哌啶基、3-哌啶基、4-哌啶基、1,3-二烷-5-基、2-四氢吡喃基、4-四氢吡喃基、2-四氢噻吩基、3-六氢哒嗪基、4-六氢哒嗪基、2-六氢嘧啶基、4-六氢嘧啶基、5-六氢嘧啶基和2-哌嗪基;
-含有1-4个氮原子或1-3个氮原子和1个硫或氧原子的5员杂芳基:除了碳原子外可以含有1-4个氮原子或1-3个氮原子和1个硫或氧原子作为环成员的5员杂芳基,例如2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基和1,3,4-三唑-2-基;
-含有1-3个或1-4个氮原子的6员杂芳基:除了碳原子外还可含有1-3个或1-4个氮原子作为环成员的6员杂芳基,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基和2-吡嗪基;
亚烷基:3-6个CH2基团的二价非支化链,例如CH2、CH2CH2、CH2CH2CH2、CH2CH2CH2CH2和CH2CH2CH2CH2CH2;
氧基亚烷基:具有2-4个CH2基团的二价非支化链,其中一根价键均经由氧原子连接于骨架上,例如OCH2CH2、OCH2CH2CH2和OCH2CH2CH2CH2;
氧基亚烷氧基:具有1-3个CH2基团的二价非支化链,其中两根价键经由氧原子连接于骨架上,例如OCH2O、OCH2CH2O和OCH2CH2CH2O。
本发明范围包括具有手性中心的式I化合物的(R)-和(S)-异构体以及外消旋体。
考虑到式I的三唑并嘧啶的意欲用途,特别优选取代基的下列含义,在每种情况下单独或组合:
优选其中R1为氢或C1-C4烷基,如氢或甲基或乙基,尤其是氢的化合物I。
此外,优选其中R2为C1-C8烷基或C3-C6环烷基,尤其是C1-C6烷基或C3-C6环烷基,优选甲基、乙基、异丙基、异丁基、叔丁基、仲戊基、环丙基或环戊基,尤其是叔丁基的化合物I。
同样优选其中R3为氢、C1-C8烷基或C3-C6环烷基,尤其是氢、C1-C6烷基或C3-C6环烷基,优选氢、甲基、乙基、正丙基或异丙基的化合物I。若R3为烷基,则R3优选具有与R2相同的含义。
在式I化合物的其他实施方案中,R2和R3一起形成C3-C6亚烷基,尤其是C3-C4亚烷基。
在式I化合物的其他实施方案中,R4、R5、R6和R7各自为氢或C1-C4烷基,尤其是氢、甲基或乙基,尤其是氢。
在式I化合物的其他实施方案中,R4和R5和/或R6和R7在每种情况下一起形成C3-C6亚烷基、C3-C6氧基亚烷基或C2-C5氧基亚烷氧基,尤其是C3-C4亚烷基。
在式I化合物的优选实施方案中,指数p为0。
在式I化合物的另一优选实施方案中,Y为氧。
在式I化合物的其他实施方案中,Z为单价基团。
在式I化合物的优选实施方案中,Z为C1-C4烷基或C1-C4烷基羰基,尤其是甲基、乙基、正丙基、异丙基、乙酰基、丙-1-酮基或丁-1-酮基。
优选其中X为卤素、C1-C4烷基、氰基或C1-C4烷氧基,如氯、溴、甲基、氰基、甲氧基或乙氧基,尤其是氯的化合物I。
在化合物I的其他实施方案中,至少一个基团L位于三唑并嘧啶骨架的连接点的邻位,尤其是氯、氟或甲基。
此外,特别优选其中被Lm取代的苯基为基团A的化合物I:
其中#为三唑并嘧啶骨架的连接点,以及
L1为氟、氯、CH3或CF3;
L2、L4相互独立地为氢或氟;
L3为氢、氟、氯、CN、CH3、OCH3、NH2、NHCH3、N(CH3)2、C(O)NH2或C(O)CH3;和
L5为氢、氟、氯或CH3。
特别优选其中Lm为下列取代组合之一的化合物I:2-氟-6-氯、2,6-二氟、2,6-二氯、2-氟-6-甲基、2,4,6-三氟、2,6-二氟-4-甲氧基、2-氯-4-甲氧基、五氟、2-甲基-4-氟、2-三氟甲基、2-甲氧基-6-氟、2-氯、2-氟、2,4-二氟、2-氟-4-氯、2-氯-4-氟、2-氯-5-氟、2,3-二氟、2,5-二氟、2,3,4-三氟、2-甲基、2,4-二甲基、2-甲基-4-氯、2-甲基-5-氟、2-氟-4-甲基、2,6-二甲基、2,4,6-三甲基、2,6-二氟-4-甲基、2-三氟甲基-4-氟、2-三氟甲基-5-氟或2-三氟甲基-5-氯。
本发明的进一步优选实施方案涉及式I.1化合物:
其中各变量如上所定义。
本发明的其他实施方案涉及式I.2化合物:
其中各变量如上所定义。
本发明的其他实施方案涉及其中Z为经由羰基连接的基团的式I和I.1化合物。
这些化合物尤其对应于式I.3:
其中各变量根据式I所定义且Z如下所定义:氢、C1-C8烷基、C1-C8烷氧基、C3-C6环烷基、C3-C8链烯氧基、C3-C8炔氧基、C3-C6环烷氧基、C3-C6环烯氧基、NRARB、包含1-4个选自O、N或S的杂原子的5-10员饱和、部分不饱和或芳族杂环;基团Z可以部分或完全被卤代或带有1-3个基团Rb。
尤其考虑到它们的应用,优选汇编在下表中的化合物I。此外,对表中取代基所提到的基团本身为所述取代基的特别优选实施方案,与其中提到它们的组合无关。
除了表1-64中提到的化合物之外,其中X为氰基、甲基或甲氧基的对应衍生物也形成优选的主题。
表1
其中X为氯,Lm为2-氟-6-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表2
其中X为氯,Lm为2,6-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表3
其中X为氯,Lm为2,6-二氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表4
其中X为氯,Lm为2-氟-6-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表5
其中X为氯,Lm为2,4,6-三氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表6
其中X为氯,Lm为2,6-二氟-4-甲氧基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表7
其中X为氯,Lm为五氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表8
其中X为氯,Lm为2-甲基-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表9
其中X为氯,Lm为2-三氟甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表10
其中X为氯,Lm为2-甲氧基-6-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表11
其中X为氯,Lm为2-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表12
其中X为氯,Lm为2-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表13
其中X为氯,Lm为2,4-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表14
其中X为氯,Lm为2-氟-4-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表15
其中X为氯,Lm为2-氯-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表16
其中X为氯,Lm为2,3-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表17
其中X为氯,Lm为2,5-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表18
其中X为氯,Lm为2,3,4-三氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表19
其中X为氯,Lm为2-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表20
其中X为氯,Lm为2,4-二甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表21
其中X为氯,Lm为2-甲基-4-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表22
其中X为氯,Lm为2-氟-4-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表23
其中X为氯,Lm为2,6-二甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表24
其中X为氯,Lm为2,4,6-三甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表25
其中X为氯,Lm为2,6-二氟4-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表26
其中X为氯,Lm为2-三氟甲基-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表27
其中X为氯,Lm为2-三氟甲基-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表28
其中X为氯,Lm为2-三氟甲基-5-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表29
其中X为氯,Lm为2-氯-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表30
其中X为氯,Lm为2-氯-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表31
其中X为氯,Lm为2-甲基-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表32
其中X为氯,Lm为2-氯-4-甲氧基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表33
其中X为氯,Lm为2-氟-6-氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表34
其中X为氯,Lm为2,6-二氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表35
其中X为氯,Lm为2,6-二氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表36
其中X为氯,Lm为2-氟-6-甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表37
其中X为氯,Lm为2,4,6-三氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表38
其中X为氯,Lm为2,6-二氟-4-甲氧基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表39
其中X为氯,Lm为五氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表40
其中X为氯,Lm为2-甲基-4-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表41
其中X为氯,Lm为2-三氟甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表42
其中X为氯,Lm为2-甲氧基-6-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表43
其中X为氯,Lm为2-氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表44
其中X为氯,Lm为2-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表45
其中X为氯,Lm为2,4-二氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表46
其中X为氯,Lm为2-氟-4-氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表47
其中X为氯,Lm为2-氯-4-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表48
其中X为氯,Lm为2,3-二氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表49
其中X为氯,Lm为2,5-二氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表50
其中X为氯,Lm为2,3,4-三氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表51
其中X为氯,Lm为2-甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表52
其中X为氯,Lm为2,4-二甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表53
其中X为氯,Lm为2-甲基-4-氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表54
其中X为氯,Lm为2-氟-4-甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表55
其中X为氯,Lm为2,6-二甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表56
其中X为氯,Lm为2,4,6-三甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表57
其中X为氯,Lm为2,6-二氟-4-甲基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表58
其中X为氯,Lm为2-三氟甲基-4-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表59
其中X为氯,Lm为2-三氟甲基-5-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表60
其中X为氯,Lm为2-三氟甲基-5-氯,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表61
其中X为氯,Lm为2-氯-4-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表62
其中X为氯,Lm为2-氯-5-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表63
其中X为氯,Lm为2-甲基-5-氟,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表64
其中X为氯,Lm为2-氯-4-甲氧基,R1为甲基,R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表A的一行的式I.1化合物
表65
其中X为氯,Lm为2-氟-6-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表66
其中X为氯,Lm为2,6-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表67
其中X为氯,Lm为2,6-二氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表68
其中X为氯,Lm为2-氟-6-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表69
其中X为氯,Lm为2,4,6-三氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表70
其中X为氯,Lm为2,6-二氟-4-甲氧基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表71
其中X为氯,Lm为五氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表72
其中X为氯,Lm为2-甲基-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表73
其中X为氯,Lm为2-三氟甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表74
其中X为氯,Lm为2-甲氧基-6-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表75
其中X为氯,Lm为2-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表76
其中X为氯,Lm为2-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表77
其中X为氯,Lm为2,4-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表78
其中X为氯,Lm为2-氟-4-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表79
其中X为氯,Lm为2-氯-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表80
其中X为氯,Lm为2,3-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表81
其中X为氯,Lm为2,5-二氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表82
其中X为氯,Lm为2,3,4-三氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表83
其中X为氯,Lm为2-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表84
其中X为氯,Lm为2,4-二甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表85
其中X为氯,Lm为2-甲基-4-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表86
其中X为氯,Lm为2-氟-4-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表87
其中X为氯,Lm为2,6-二甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表88
其中X为氯,Lm为2,4,6-三甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表89
其中X为氯,Lm为2,6-二氟-4-甲基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表90
其中X为氯,Lm为2-三氟甲基-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表91
其中X为氯,Lm为2-三氟甲基-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表92
其中X为氯,Lm为2-三氟甲基-5-氯,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表93
其中X为氯,Lm为2-氯-4-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表94
其中X为氯,Lm为2-氯-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表95
其中X为氯,Lm为2-甲基-5-氟,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表96
其中X为氯,Lm为2-氯-4-甲氧基,R1、R4和R5为氢且R2、R3、Y和Z的组合对每一化合物而言对应于表B的一行的式I.3化合物
表A
序号 | R2 | R3 | Y | Z |
A-1 | CH3 | H | O | H |
A-2 | CH3 | H | O | CH3 |
A-3 | CH3 | H | O | CH2CH3 |
A-4 | CH3 | H | O | CH2CH2CH3 |
A-5 | CH3 | H | O | CH2CH2CH2CH3 |
A-6 | CH3 | H | O | CH(CH3)CH2CH3 |
A-7 | CH3 | H | O | CH2CH2(CH3)2 |
A-8 | CH3 | H | O | C(CH3)3 |
A-9 | CH3 | H | O | CH(CH3)2 |
A-10 | CH3 | H | O | C(O)CH3 |
序号 | R2 | R3 | Y | Z |
A-11 | CH3 | H | O | C(O)CH2CH3 |
A-12 | CH3 | H | O | C(O)CH2CH2CH3 |
A-13 | CH3 | H | O | C(O)CH2CH2CH2CH3 |
A-14 | CH3 | H | O | C(O)CH(CH2CH3)2 |
A-15 | CH3 | H | O | C(O)CH(CH2F)2 |
A-16 | CH3 | H | O | C(O)CH2CH2C6H5 |
A-17 | CH3 | H | O | C(O)C6H5 |
A-18 | CH3 | H | O | C(O)(4-OCH3-C6H4) |
A-19 | CH3 | H | O | C(O)(4-Cl-C6H4) |
A-20 | CH3 | H | O | C(O)(4-Cl-C6H4) |
A-21 | CH3 | H | O | C(O)(4-吡啶基) |
A-22 | CH3 | H | O | C(O)(2-CH2CH3-C6H4) |
A-23 | CH3 | H | O | C(O)(2-CH3-C6H4) |
A-24 | CH3 | H | O | C(O)(3-CH3-C6H4) |
A-25 | CH3 | H | O | C(O)(4-CH3-C6H4) |
A-26 | CH3 | CH3 | O | H |
A-27 | CH3 | CH3 | O | CH3 |
A-28 | CH3 | CH3 | O | CH2CH3 |
A-29 | CH3 | CH3 | O | CH2CH2CH3 |
A-30 | CH3 | CH3 | O | CH(CH3)2 |
A-31 | CH3 | CH3 | O | CH2CH2CH2CH3 |
A-32 | CH3 | CH3 | O | CH(CH3)CH2CH3 |
A-33 | CH3 | CH3 | O | CH2 CH2(CH3)2 |
A-34 | CH3 | CH3 | O | C(CH3)3 |
A-35 | CH3 | CH3 | O | C(O)CH3 |
A-36 | CH3 | CH3 | O | C(O)CH2CH3 |
A-37 | CH3 | CH3 | O | C(O)CH2CH2CH3 |
A-38 | CH3 | CH3 | O | C(O)CH2CH2CH2CH3 |
A-39 | CH3 | CH3 | O | C(O)CH(CH2CH3)2 |
A-40 | CH3 | CH3 | O | C(O)CH(CH2F)2 |
A-41 | CH3 | CH3 | O | C(O)CH2CH2C6H5 |
A-42 | CH3 | CH3 | O | C(O)C6H5 |
A-43 | CH3 | CH3 | O | C(O)(4-OCH3-C6H4) |
序号 | R2 | R3 | Y | Z |
A-44 | CH3 | CH3 | O | C(O)(4-Cl-C6H4) |
A-45 | CH3 | CH3 | O | C(O)(4-CH-C6H4) |
A-46 | CH3 | CH3 | O | C(O)(4-吡啶基) |
A-47 | CH3 | CH3 | O | C(O)(2-CH2CH3-C6H4) |
A-48 | CH3 | CH3 | O | C(O)(2-CH3-C6H4) |
A-49 | CH3 | CH3 | O | C(O)(3-CH3-C6H4) |
A-50 | CH3 | CH3 | O | C(O)(4-CH3-C6H4) |
A-51 | CH2CH3 | H | O | H |
A-52 | CH2CH3 | H | O | CH3 |
A-53 | CH2CH3 | H | O | CH2CH3 |
A-54 | CH2CH3 | H | O | CH2CH2CH3 |
A-55 | CH2CH3 | H | O | CH(CH3)2 |
A-56 | CH2CH3 | H | O | CH2CH2CH2CH3 |
A-57 | CH2CH3 | H | O | CH(CH3)CH2CH3 |
A-58 | CH2CH3 | H | O | CH2CH2(CH3)2 |
A-59 | CH2CH3 | H | O | C(CH3)3 |
A-60 | CH2CH3 | H | O | C(O)CH3 |
A-61 | CH2CH3 | H | O | C(O)CH2CH3 |
A-62 | CH2CH3 | H | O | C(O)CH2CH2CH3 |
A-63 | CH2CH3 | H | O | C(O)CH2CH2CH2CH3 |
A-64 | CH2CH3 | H | O | C(O)CH(CH2CH3)2 |
A-65 | CH2CH3 | H | O | C(O)CH(CH2F)2 |
A-66 | CH2CH3 | H | O | C(O)CH2CH2C6H5 |
A-67 | CH2CH3 | H | O | C(O)C6H5 |
A-68 | CH2CH3 | H | O | C(O)(4-OCH3-C6H4) |
A-69 | CH2CH3 | H | O | C(O)(4-Cl-C6H4) |
A-70 | CH2CH3 | H | O | C(O)(4-Cl-C6H4) |
A-71 | CH2CH3 | H | O | C(O)(4-吡啶基) |
A-72 | CH2CH3 | H | O | C(O)(2-CH2CH3-C6H4) |
A-73 | CH2CH3 | H | O | C(O)(2-CH3-C6H4) |
A-74 | CH2CH3 | H | O | C(O)(3-CH3-C6H4) |
A-75 | CH2CH3 | H | O | C(O)(4-CH3-C6H4) |
A-76 | CH2CH3 | CH2CH3 | O | H |
序号 | R2 | R3 | Y | Z |
A-77 | CH2CH3 | CH2CH3 | O | CH3 |
A-78 | CH2CH3 | CH2CH3 | O | CH2CH3 |
A-79 | CH2CH3 | CH2CH3 | O | CH2CH2CH3 |
A-80 | CH2CH3 | CH2CH3 | O | CH(CH3)2 |
A-81 | CH2CH3 | CH2CH3 | O | CH2CH2CH2CH3 |
A-82 | CH2CH3 | CH2CH3 | O | CH(CH3)CH2CH3 |
A-83 | CH2CH3 | CH2CH3 | O | CH2CH2(CH3)2 |
A-84 | CH2CH3 | CH2CH3 | O | C(CH3)3 |
A-85 | CH2CH3 | CH2CH3 | O | C(O)CH3 |
A-86 | CH2CH3 | CH2CH3 | O | C(O)CH2CH3 |
A-87 | CH2CH3 | CH2CH3 | O | C(O)CH2CH2CH3 |
A-88 | CH2CH3 | CH2CH3 | O | C(O)CH2CH2CH2CH3 |
A-89 | CH2CH3 | CH2CH3 | O | C(O)CH(CH2CH3)2 |
A-90 | CH2CH3 | CH2CH3 | O | C(O)CH(CH2F)2 |
A-91 | CH2CH3 | CH2CH3 | O | C(O)CH2CH2C6H5 |
A-92 | CH2CH3 | CH2CH3 | O | C(O)C6H5 |
A-93 | CH2CH3 | CH2CH3 | O | C(O)(4-OCH3-C6H4) |
A-94 | CH2CH3 | CH2CH3 | O | C(O)(4-Cl-C6H4) |
A-95 | CH2CH3 | CH2CH3 | O | C(O)(4-Cl-C6H4) |
A-96 | CH2CH3 | CH2CH3 | O | C(O)(4-吡啶基) |
A-97 | CH2CH3 | CH2CH3 | O | C(O)(2-CH2CH3-C6H4) |
A-98 | CH2CH3 | CH2CH3 | O | C(O)(2-CH3-C6H4) |
A-99 | CH2CH3 | CH2CH3 | O | C(O)(3-CH3-C6H4) |
A-100 | CH2CH3 | CH2CH3 | O | C(O)(4-CH3-C6H4) |
A-101 | CH2CH2CH3 | H | O | H |
A-102 | CH2CH2CH3 | H | O | CH3 |
A-103 | CH2CH2CH3 | H | O | CH2CH3 |
A-104 | CH2CH2CH3 | H | O | CH2CH2CH3 |
A-105 | CH2CH2CH3 | H | O | CH(CH3)2 |
A-106 | CH2CH2CH3 | H | O | CH2CH2CH2CH3 |
A-107 | CH2CH2CH3 | H | O | CH(CH3)CH2CH3 |
A-108 | CH2CH2CH3 | H | O | CH2CH2(CH3)2 |
A-109 | CH2CH2CH3 | H | O | C(CH3)3 |
序号 | R2 | R3 | Y | Z |
A-110 | CH2CH2CH3 | H | O | C(O)CH3 |
A-111 | CH2CH2CH3 | H | O | C(O)CH2 CH3 |
A-112 | CH2CH2CH3 | H | O | C(O)CH2CH2CH3 |
A-113 | CH2CH2CH3 | H | O | C(O)CH2CH2CH2CH3 |
A-114 | CH2CH2CH3 | H | O | C(O)CH(CH2CH3)2 |
A-115 | CH2CH2CH3 | H | O | C(O)CH(CH2F)2 |
A-116 | CH2CH2CH3 | H | O | C(O)CH2CH2C6H5 |
A-117 | CH2CH2CH3 | H | O | C(O)C6H5 |
A-118 | CH2CH2CH3 | H | O | C(O)(4-OCH3-C6H4) |
A-119 | CH2CH2CH3 | H | O | C(O)(4-Cl-C6H4) |
A-120 | CH2CH2CH3 | H | O | C(O)(4-Cl-C6H4) |
A-121 | CH2CH2CH3 | H | O | C(O)(4-吡啶基) |
A-122 | CH2CH2CH3 | H | O | C(O)(2-CH2CH3-C6H4) |
A-123 | CH2CH2CH3 | H | O | C(O)(2-CH3-C6H4) |
A-124 | CH2CH2CH3 | H | O | C(O)(3-CH3-C6H4) |
A-125 | CH2CH2CH3 | H | O | C(O)(4-CH3-C6H4) |
A-126 | CH2CH2CH3 | CH2CH2CH3 | O | H |
A-127 | CH2CH2CH3 | CH2CH2CH3 | O | CH3 |
A-128 | CH2CH2CH3 | CH2CH2CH3 | O | CH2CH3 |
A-129 | CH2CH2CH3 | CH2CH2CH3 | O | CH2CH2CH3 |
A-130 | CH2CH2CH3 | CH2CH2CH3 | O | CH(CH3)2 |
A-131 | CH2CH2CH3 | CH2CH2CH3 | O | CH2CH2CH2CH3 |
A-132 | CH2CH2CH3 | CH2CH2CH3 | O | CH(CH3)CH2CH3 |
A-133 | CH2CH2CH3 | CH2CH2CH3 | O | CH2CH2(CH3)2 |
A-134 | CH2CH2CH3 | CH2CH2CH3 | O | C(CH3)3 |
A-135 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH3 |
A-136 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH2CH3 |
A-137 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH2CH2CH3 |
A-138 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH2CH2CH2CH3 |
A-139 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH(CH2CH3)2 |
A-140 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH(CH2F)2 |
A-141 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)CH2CH2C6H5 |
A-142 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)C6H5 |
序号 | R2 | R3 | Y | Z |
A-143 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(4-OCH3-C6H4) |
A-144 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(4-Cl-C6H4) |
A-145 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(4-Cl-C6H4) |
A-146 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(4-吡啶基) |
A-147 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(2-CH2CH3-C6H4) |
A-148 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(2-CH3-C6H4) |
A-149 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(3-CH3-C6H4) |
A-150 | CH2CH2CH3 | CH2CH2CH3 | O | C(O)(4-CH3-C6H4) |
A-151 | CH(CH3)2 | H | O | H |
A-152 | CH(CH3)2 | H | O | CH3 |
A-153 | CH(CH3)2 | H | O | CH2CH3 |
A-154 | CH(CH3)2 | H | O | CH2CH2CH3 |
A-155 | CH(CH3)2 | H | O | CH(CH3)2 |
A-156 | CH(CH3)2 | H | O | CH2CH2CH2CH3 |
A-157 | CH(CH3)2 | H | O | CH(CH3)CH2CH3 |
A-158 | CH(CH3)2 | H | O | CH2CH2(CH3)2 |
A-159 | CH(CH3)2 | H | O | C(CH3)3 |
A-160 | CH(CH3)2 | H | O | C(O)CH3 |
A-161 | CH(CH3)2 | H | O | C(O)CH2CH3 |
A-162 | CH(CH3)2 | H | O | C(O)CH2CH2CH3 |
A-163 | CH(CH3)2 | H | O | C(O)CH2CH2CH2CH3 |
A-164 | CH(CH3)2 | H | O | C(O)CH(CH2CH3)2 |
A-165 | CH(CH3)2 | H | O | C(O)CH(CH2F)2 |
A-166 | CH(CH3)2 | H | O | C(O)CH2CH2C6H5 |
A-167 | CH(CH3)2 | H | O | C(O)C6H5 |
A-168 | CH(CH3)2 | H | O | C(O)(4-OCH3-C6H4) |
A-169 | CH(CH3)2 | H | O | C(O)(4-Cl-C6H4) |
A-170 | CH(CH3)2 | H | O | C(O)(4-Cl-C6H4) |
A-171 | CH(CH3)2 | H | O | C(O)(4-吡啶基) |
A-172 | CH(CH3)2 | H | O | C(O)(2-CH2CH3-C6H4) |
A-173 | CH(CH3)2 | H | O | C(O)(2-CH3-C6H4) |
A-174 | CH(CH3)2 | H | O | C(O)(3-CH3-C6H4) |
A-175 | CH(CH3)2 | H | O | C(O)(4-CH3-C6H4) |
序号 | R2 | R3 | Y | Z |
A-176 | CH(CH3)2 | CH(CH3)2 | O | H |
A-177 | CH(CH3)2 | CH(CH3)2 | O | CH3 |
A-178 | CH(CH3)2 | CH(CH3)2 | O | CH2CH3 |
A-179 | CH(CH3)2 | CH(CH3)2 | O | CH2CH2CH3 |
A-180 | CH(CH3)2 | CH(CH3)2 | O | CH(CH3)2 |
A-181 | CH(CH3)2 | CH(CH3)2 | O | CH2CH2CH2CH3 |
A-182 | CH(CH3)2 | CH(CH3)2 | O | CH(CH3)CH2CH3 |
A-183 | CH(CH3)2 | CH(CH3)2 | O | CH2CH2(CH3)2 |
A-184 | CH(CH3)2 | CH(CH3)2 | O | C(CH3)3 |
A-185 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH3 |
A-186 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH2CH3 |
A-187 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH2CH2CH3 |
A-188 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH2CH2CH2CH3 |
A-189 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH(CH2CH3)2 |
A-190 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH(CH2F)2 |
A-191 | CH(CH3)2 | CH(CH3)2 | O | C(O)CH2CH2C6H5 |
A-192 | CH(CH3)2 | CH(CH3)2 | O | C(O)C6H5 |
A-193 | CH(CH3)2 | CH(CH3)2 | O | C(O)(4-OCH3-C6H4) |
A-194 | CH(CH3)2 | CH(CH3)2 | O | C(O)(4-Cl-C6H4) |
A-195 | CH(CH3)2 | CH(CH3)2 | O | C(O)(4-Cl-C6H4) |
A-196 | CH(CH3)2 | CH(CH3)2 | O | C(O)(4-吡啶基) |
A-197 | CH(CH3)2 | CH(CH3)2 | O | C(O)(2-CH2CH3-C6H4) |
A-198 | CH(CH3)2 | CH(CH3)2 | O | C(O)(2-CH3-C6H4) |
A-199 | CH(CH3)2 | CH(CH3)2 | O | C(O)(3-CH3-C6H4) |
A-200 | CH(CH3)2 | CH(CH3)2 | O | C(O)(4-CH3-C6H4) |
A-201 | C(CH3)3 | H | O | H |
A-202 | C(CH3)3 | H | O | CH3 |
A-203 | C(CH3)3 | H | O | CH2CH3 |
A-204 | C(CH3)3 | H | O | CH2CH2CH3 |
A-205 | C(CH3)3 | H | O | CH(CH3)2 |
A-206 | C(CH3)3 | H | O | CH2CH2CH2CH3 |
A-207 | C(CH3)3 | H | O | CH(CH3)CH2CH3 |
A-208 | C(CH3)3 | H | O | CH2CH2(CH3)2 |
序号 | R2 | R3 | Y | Z |
A-209 | C(CH3)3 | H | O | C(CH3)3 |
A-210 | C(CH3)3 | H | O | C(O)CH3 |
A-211 | C(CH3)3 | H | O | C(O)CH2CH3 |
A-212 | C(CH3)3 | H | O | C(O)CH2CH2CH3 |
A-213 | C(CH3)3 | H | O | C(O)CH2CH2CH2CH3 |
A-214 | C(CH3)3 | H | O | C(O)CH(CH2CH3)2 |
A-215 | C(CH3)3 | H | O | C(O)CH(CH2F)2 |
A-216 | C(CH3)3 | H | O | C(O)CH2CH2C6H5 |
A-217 | C(CH3)3 | H | O | C(O)C6H5 |
A-218 | C(CH3)3 | H | O | C(O)(4-OCH3-C6H4) |
A-219 | C(CH3)3 | H | O | C(O)(4-Cl-C6H4) |
A-220 | C(CH3)3 | H | O | C(O)(4-Cl-C6H4) |
A-221 | C(CH3)3 | H | O | C(O)(4-吡啶基) |
A-222 | C(CH3)3 | H | O | C(O)(2-CH2CH3-C6H4) |
A-223 | C(CH3)3 | H | O | C(O)(2-CH3-C6H4) |
A-224 | C(CH3)3 | H | O | C(O)(3-CH3-C6H4) |
A-225 | C(CH3)3 | H | O | C(O)(4-CH3-C6H4) |
A-226 | CH(CH2CH3)2 | H | O | H |
A-227 | CH(CH2CH3)2 | H | O | CH3 |
A-228 | CH(CH2CH3)2 | H | O | CH2CH3 |
A-229 | CH(CH2CH3)2 | H | O | CH2CH2CH3 |
A-230 | CH(CH2CH3)2 | H | O | CH(CH3)2 |
A-231 | CH(CH2CH3)2 | H | O | CH2CH2CH2CH3 |
A-232 | CH(CH2CH3)2 | H | O | CH(CH3)CH2CH3 |
A-233 | CH(CH2CH3)2 | H | O | CH2CH2(CH3)2 |
A-234 | CH(CH2CH3)2 | H | O | C(CH3)3 |
A-235 | CH(CH2CH3)2 | H | O | C(O)CH3 |
A-236 | CH(CH2CH3)2 | H | O | C(O)CH2CH3 |
A-237 | CH(CH2CH3)2 | H | O | C(O)CH2CH2CH3 |
A-238 | CH(CH2CH3)2 | H | O | C(O)CH2CH2CH2CH3 |
A-239 | CH(CH2CH3)2 | H | O | C(O)CH(CH2CH3)2 |
A-240 | CH(CH2CH3)2 | H | O | C(O)CH(CH2F)2 |
A-241 | CH(CH2CH3)2 | H | O | C(O)CH2CH2C6H5 |
序号 | Ru2 | R3 | Y | Z |
A-242 | CH(CH2CH3)2 | H | O | C(O)C6H5 |
A-243 | CH(CH2CH3)2 | H | O | C(O)(4-OCH3-C6H4) |
A-244 | CH(CH2CH3)2 | H | O | C(O)(4-Cl-C6H4) |
A-245 | CH(CH2CH3)2 | H | O | C(O)(4-Cl-C6H4) |
A-246 | CH(CH2CH3)2 | H | O | C(O)(4-吡啶基) |
A-247 | CH(CH2CH3)2 | H | O | C(O)(2-CH2CH3-C6H4) |
A-248 | CH(CH2CH3)2 | H | O | C(O)(2-CH3-C6H4) |
A-249 | CH(CH2CH3)2 | H | O | C(O)(3-CH3-C6H4) |
A-250 | CH(CH2CH3)2 | H | O | C(O)(4-CH3-C6H4) |
A-251 | c-C3H5 | H | O | H |
A-252 | c-C3H5 | H | O | CH3 |
A-253 | c-C3H5 | H | O | CH2CH3 |
A-254 | c-C3H5 | H | O | CH2CH2CH3 |
A-255 | c-C3H5 | H | O | CH(CH3)2 |
A-256 | c-C3H5 | H | O | CH2CH2CH2CH3 |
A-257 | c-C3H5 | H | O | CH(CH3)CH2CH3 |
A-258 | c-C3H5 | H | O | CH2CH2(CH3)2 |
A-259 | c-C3H5 | H | O | C(CH3)3 |
A-260 | c-C3H5 | H | O | C(O)CH3 |
A-261 | c-C3H5 | H | O | C(O)CH2CH3 |
A-262 | c-C3H5 | H | O | C(O)CH2CH2CH3 |
A-263 | c-C3H5 | H | O | C(O)CH2CH2CH2CH3 |
A-264 | c-C3H5 | H | O | C(O)CH(CH2CH3)2 |
A-265 | c-C3H5 | H | O | C(O)CH(CH2F)2 |
A-266 | c-C3H5 | H | O | C(O)CH2CH2C6H5 |
A-267 | c-C3H5 | H | O | C(O)C6H5 |
A-268 | c-C3H5 | H | O | C(O)(4-OCH3-C6H4) |
A-269 | c-C3H5 | H | O | C(O)(4-Cl-C6H4) |
A-270 | c-C3H5 | H | O | C(O)(4-Cl-C6H4) |
A-271 | c-C3H5 | H | O | C(O)(4-吡啶基) |
A-272 | c-C3H5 | H | O | C(O)(2-CH2CH3-C6H4) |
A-273 | c-C3H5 | H | O | C(O)(2-CH3-C6H4) |
A-274 | c-C3H5 | H | O | C(O)(3-CH3-C6H4) |
序号 | R2 | R3 | Y | Z |
A-275 | c-C3H5 | H | O | C(O)(4-CH3-C6H4) |
A-276 | c-C3H5 | CH3 | O | H |
A-277 | c-C3H5 | CH3 | O | CH3 |
A-278 | c-C3H5 | CH3 | O | CH2CH3 |
A-279 | c-C3H5 | CH3 | O | CH2CH2CH3 |
A-280 | c-C3H5 | CH3 | O | CH(CH3)2 |
A-281 | c-C3H5 | CH3 | O | CH2CH2CH2CH3 |
A-282 | c-C3H5 | CH3 | O | CH(CH3)CH2CH3 |
A-283 | c-C3H5 | CH3 | O | CH2CH2(CH3)2 |
A-284 | c-C3H5 | CH3 | O | C(CH3)3 |
A-285 | c-C3H5 | CH3 | O | C(O)CH3 |
A-286 | c-C3H5 | CH3 | O | C(O)CH2CH3 |
A-287 | c-C3H5 | CH3 | O | C(O)CH2CH2CH3 |
A-288 | c-C3H5 | CH3 | O | C(O)CH2CH2CH2CH3 |
A-289 | c-C3H5 | CH3 | O | C(O)CH(CH2CH3)2 |
A-290 | c-C3H5 | CH3 | O | C(O)CH(CH2F)2 |
A-291 | c-C3H5 | CH3 | O | C(O)CH2CH2C6H5 |
A-292 | c-C3H5 | CH3 | O | C(O)C6H5 |
A-293 | c-C3H5 | CH3 | O | C(O)(4-OCH3-C6H4) |
A-294 | c-C3H5 | CH3 | O | C(O)(4-Cl-C6H4) |
A-295 | c-C3H5 | CH3 | O | C(O)(4-Cl-C6H4) |
A-296 | c-C3H5 | CH3 | O | C(O)(4-吡啶基) |
A-297 | c-C3H5 | CH3 | O | C(O)(2-CH2CH3-C6H4) |
A-298 | c-C3H5 | CH3 | O | C(O)(2-CH3-C6H4) |
A-299 | c-C3H5 | CH3 | O | C(O)(3-CH3-C6H4) |
A-300 | c-C3H5 | CH3 | O | C(O)(4-CH3-C6H4) |
A-301 | c-C5H9 | H | O | H |
A-302 | c-C5H9 | H | O | CH3 |
A-303 | c-C5H9 | H | O | CH2CH3 |
A-304 | c-C5H9 | H | O | CH2CH2CH3 |
A-305 | c-C5H9 | H | O | CH(CH3)2 |
A-306 | c-C5H9 | H | O | CH2CH2CH2CH3 |
A-307 | c-C5H9 | H | O | CH(CH3)CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-308 | c-C5H9 | H | O | CH2CH2(CH3)2 |
A-309 | c-C5H9 | H | O | C(CH3)3 |
A-310 | c-C5H9 | H | O | C(O)CH3 |
A-311 | c-C5H9 | H | O | C(O)CH2CH3 |
A-312 | c-C5H9 | H | O | C(O)CH2CH2CH3 |
A-313 | c-C5H9 | H | O | C(O)CH2CH2CH2CH3 |
A-314 | c-C5H9 | H | O | C(O)CH(CH2CH3)2 |
A-315 | c-C5H9 | H | O | C(O)CH(CH2F)2 |
A-316 | c-C5H9 | H | O | C(O)CH2CH2C6H5 |
A-317 | c-C5H9 | H | O | C(O)C6H5 |
A-318 | c-C5H9 | H | O | C(O)(4-OCH3-C6H4) |
A-319 | c-C5H9 | H | O | C(O)(4-Cl-C6H4) |
A-320 | c-C5H9 | H | O | C(O)(4-Cl-C6H4) |
A-321 | c-C5H9 | H | O | C(O)(4-吡啶基) |
A-322 | c-C5H9 | H | O | C(O)(2-CH2CH3-C6H4) |
A-323 | c-C5H9 | H | O | C(O)(2-CH3-C6H4) |
A-324 | c-C5H9 | H | O | C(O)(3-CH3-C6H4) |
A-325 | c-C5H9 | H | O | C(O)(4-CH3-C6H4) |
A-326 | c-C5H9 | CH3 | O | H |
A-327 | c-C5H9 | CH3 | O | CH3 |
A-328 | c-C5H9 | CH3 | O | CH2CH3 |
A-329 | c-C5H9 | CH3 | O | CH2CH2CH3 |
A-330 | c-C5H9 | CH3 | O | CH(CH3)2 |
A-331 | c-C5H9 | CH3 | O | CH2CH2CH2CH3 |
A-332 | c-C5H9 | CH3 | O | CH(CH3)CH2CH3 |
A-333 | c-C5H9 | CH3 | O | CH2CH2(CH3)2 |
A-334 | c-C5H9 | CH3 | O | C(CH3)3 |
A-335 | c-C5H9 | CH3 | O | C(O)CH3 |
A-336 | c-C5H9 | CH3 | O | C(O)CH2CH3 |
A-337 | c-C5H9 | CH3 | O | C(O)CH2CH2CH3 |
A-338 | c-C5H9 | CH3 | O | C(O)CH2CH2CH2CH3 |
A-339 | c-C5H9 | CH3 | O | C(O)CH(CH2CH3)2 |
A-340 | c-C5H9 | CH3 | O | C(O)CH(CH2F)2 |
序号 | R2 | R3 | Y | Z |
A-341 | c-C5H9 | CH3 | O | C(O)CH2CH2C6H5 |
A-342 | c-C5H9 | CH3 | O | C(O)C6H5 |
A-343 | c-C5H9 | CH3 | O | C(O)(4-OCH3-C6H4) |
A-344 | c-C5H9 | CH3 | O | C(O)(4-Cl-C6H4) |
A-345 | c-C5H9 | CH3 | O | C(O)(4-Cl-C6H4) |
A-346 | c-C5H9 | CH3 | O | C(O)(4-吡啶基) |
A-347 | c-C5H9 | CH3 | O | C(O)(2-CH2CH3-C6H4) |
A-348 | c-C5H9 | CH3 | O | C(O)(2-CH3-C6H4) |
A-349 | c-C5H9 | CH3 | O | C(O)(3-CH3-C6H4) |
A-350 | c-C5H9 | CH3 | O | C(O)(4-CH3-C6H4) |
A-351 | -CH2CH2- | O | H | |
A-352 | CH2CH2 | O | CH3 | |
A-353 | CH2CH2 | O | CH2CH3 | |
A-354 | CH2CH2 | O | CH2CH2CH3 | |
A-355 | CH2CH2 | O | CH(CH3)2 | |
A-356 | CH2CH2 | O | CH2CH2CH2CH3 | |
A-357 | CH2CH2 | O | CH(CH3)CH2CH3 | |
A-358 | CH2CH2 | O | CH2CH2(CH3)2 | |
A-359 | CH2CH2 | O | C(CH3)3 | |
A-360 | CH2CH2 | O | C(O)CH3 | |
A-361 | CH2CH2 | O | C(O)CH2CH3 | |
A-362 | CH2CH2 | O | C(O)CH2CH2CH3 | |
A-363 | CH2CH2 | O | C(O)CH2CH2CH2CH3 | |
A-364 | CH2CH2 | O | C(O)CH(CH2CH3)2 | |
A-365 | CH2CH2 | O | C(O)CH(CH2F)2 | |
A-366 | CH2CH2 | O | C(O)CH2CH2C6H5 | |
A-367 | CH2CH2 | O | C(O)C6H5 | |
A-368 | CH2CH2 | O | C(O)(4-OCH3-C6H4) | |
A-369 | CH2CH2 | O | C(O)(4-Cl-C6H4) | |
A-370 | CH2H2 | O | C(O)(4-Cl-C6H4) | |
A-371 | CH2CH2 | O | C(O)(4-吡啶基) | |
A-372 | CH2CH2 | O | C(O)(2-CH2CH3-C6H4) | |
A-373 | CH2CH2 | O | C(O)(2-CH3-C6H4) |
序号 | R2 | R3 | Y | Z |
A-374 | CH2CH2 | O | C(O)(3-CH3-C6H4) | |
A-375 | CH2CH2 | O | C(O)(4-CH3-C6H4) | |
A-376 | -CH2CH2CH2CH2- | O | H | |
A-377 | -CH2CH2CH2CH2- | O | CH3 | |
A-378 | -CH2CH2CH2CH2- | O | CH2CH3 | |
A-379 | -CH2CH2CH2CH2- | O | CH2CH2CH3 | |
A-380 | -CH2CH2CH2CH2- | O | CH(CH3)2 | |
A-381 | -CH2CH2CH2CH2- | O | CH2CH2CH2CH3 | |
A-382 | -CH2CH2CH2CH2- | O | CH(CH3)CH2CH3 | |
A-383 | -CH2CH2CH2CH2- | O | CH2CH2(CH3)2 | |
A-384 | -CH2CH2CH2CH2- | O | C(CH3)3 | |
A-385 | -CH2CH2CH2CH2- | O | C(O)CH3 | |
A-386 | -CH2CH2CH2CH2- | O | C(O)CH2CH3 | |
A-387 | -CH2CH2CH2CH2- | O | C(O)CH2CH2CH3 | |
A-388 | -CH2CH2CH2CH2- | O | C(O)CH2CH2CH2CH3 | |
A-389 | -CH2CH2CH2CH2- | O | C(O)CH(CH2CH3)2 | |
A-390 | -CH2CH2CH2CH2- | O | C(O)CH(CH2F)2 | |
A-391 | -CH2CH2CH2CH2- | O | C(O)CH2CH2C6H5 | |
A-392 | -CH2CH2CH2CH2- | O | C(O)C6H5 | |
A-393 | -CH2CH2CH2CH2- | O | C(O)(4-OCH3-C6H4) | |
A-394 | -CH2CH2CH2CH2- | O | C(O)(4-Cl-C6H4) | |
A-395 | -CH2CH2CH2CH2- | O | C(O)(4-Cl-C6H4) | |
A-396 | -CH2CH2CH2CH2- | O | C(O)(4-吡啶基) | |
A-397 | -CH2CH2CH2CH2- | O | C(O)(2-CH2CH3-C6H4) | |
A-398 | -CH2CH2CH2CH2- | O | C(O)(2-CH3-C6H4) | |
A-399 | -CH2CH2CH2CH2- | O | C(O)(3-CH3-C6H4) | |
A-400 | -CH2CH2CH2CH2- | O | C(O)(4-CH3-C6H4) | |
A-401 | CH3 | H | S | H |
A-402 | CH3 | H | S | CH3 |
A-403 | CH3 | H | S | CH2CH3 |
A-404 | CH3 | H | S | CH2CH2CH3 |
A-405 | CH3 | H | S | CH(CH3)2 |
A-406 | CH3 | H | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-407 | CH3 | H | S | CH(CH3)CH2CH3 |
A-408 | CH3 | H | S | CH2CH2(CH3)2 |
A-409 | CH3 | H | S | C(CH3)3 |
A-410 | CH3 | H | S | C(S)CH3 |
A-411 | CH3 | H | S | C(S)CH2CH3 |
A-412 | CH3 | CH3 | S | H |
A-413 | CH3 | CH3 | S | CH3 |
A-414 | CH3 | CH3 | S | CH2CH3 |
A-415 | CH3 | CH3 | S | CH2CH2CH3 |
A-416 | CH3 | CH3 | S | CH(CH3)2 |
A-417 | CH3 | CH3 | S | CH2CH2CH2CH3 |
A-418 | CH3 | CH3 | S | CH(CH3)CH2CH3 |
A-419 | CH3 | CH3 | S | CH2CH2(CH3)2 |
A-420 | CH3 | CH3 | S | C(CH3)3 |
A-421 | CH3 | CH3 | S | C(S)CH3 |
A-422 | CH3 | CH3 | S | C(S)CH2CH3 |
A-423 | CH2CH3 | H | S | H |
A-424 | CH2CH3 | H | S | CH3 |
A-425 | CH2CH3 | H | S | CH2CH3 |
A-426 | CH2CH3 | H | S | CH2CH2CH3 |
A-427 | CH2CH3 | H | S | CH(CH3)2 |
A-428 | CH2CH3 | H | S | CH2CH2CH2CH3 |
A-429 | CH2CH3 | H | S | CH(CH3)CH2CH3 |
A-430 | CH2CH3 | H | S | CH2CH2(CH3)2 |
A-431 | CH2CH3 | H | S | C(CH3)3 |
A-432 | CH2CH3 | H | S | C(S)CH3 |
A-433 | CH2CH3 | H | S | C(S)CH2CH3 |
A-434 | CH2CH3 | CH2CH3 | S | H |
A-435 | CH2CH3 | CH2CH3 | S | CH3 |
A-436 | CH2CH3 | CH2CH3 | S | CH2CH3 |
A-437 | CH2CH3 | CH2CH3 | S | CH2CH2CH3 |
A-438 | CH2CH3 | CH2CH3 | S | CH(CH3)2 |
A-439 | CH2CH3 | CH2CH3 | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-440 | CH2CH3 | CH2CH3 | S | CH(CH3)CH2CH3 |
A-441 | CH2CH3 | CH2CH3 | S | CH2CH2(CH3)2 |
A-442 | CH2CH3 | CH2CH3 | S | C(CH3)3 |
A-443 | CH2CH3 | CH2CH3 | S | C(S)CH3 |
A-444 | CH2CH3 | CH2CH3 | S | C(S)CH2CH3 |
A-445 | CH2CH2CH3 | H | S | H |
A-446 | CH2CH2CH3 | H | S | CH3 |
A-447 | CH2CH2CH3 | H | S | CH2CH3 |
A-448 | CH2CH2CH3 | H | S | CH2CH2CH3 |
A-449 | CH2CH2CH3 | H | S | CH(CH3)2 |
A-450 | CH2CH2CH3 | H | S | CH2CH2CH2CH3 |
A-451 | CH2CH2CH3 | H | S | CH(CH3)CH2CH3 |
A-452 | CH2CH2CH3 | H | S | CH2CH2(CH3)2 |
A-453 | CH2CH2CH3 | H | S | C(CH3)3 |
A-454 | CH2CH2CH3 | H | S | C(S)CH3 |
A-455 | CH2CH2CH3 | H | S | C(S)CH2CH3 |
A-456 | CH2CH2CH3 | CH2CH2CH3 | S | H |
A-457 | CH2CH2CH3 | CH2CH2CH3 | S | CH3 |
A-458 | CH2CH2CH3 | CH2CH2CH3 | S | CH2CH3 |
A-459 | CH2CH2CH3 | CH2CH2CH3 | S | CH2CH2CH3 |
A-460 | CH2CH2CH3 | CH2CH2CH3 | S | CH(CH3)2 |
A-461 | CH2CH2CH3 | CH2CH2CH3 | S | CH2CH2CH2CHx |
A-462 | CH2CH2CH3 | CH2CH2CH3 | S | CH(CH3)CH2CH3 |
A-463 | CH2CH2CH3 | CH2CH2CH3 | S | CH2CH2(CH3)2 |
A-464 | CH2CH2CH3 | CH2CH2CH3 | S | C(CH3)3 |
A-465 | CH2CH2CH3 | CH2CH2CH3 | S | C(S)CH3 |
A-466 | CH2CH2CH3 | CH2CH2CH3 | S | C(S)CH2CH3 |
A-467 | CH(CH3)2 | H | S | H |
A-468 | CH(CH3)2 | H | S | CH3 |
A-469 | CH(CH3)2 | H | S | CH2CH3 |
A-470 | CH(CH3)2 | H | S | CH2CH2CH3 |
A-471 | CH(CH3)2 | H | S | CH(CH3)2 |
A-472 | CH(CH3)2 | H | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-473 | CH(CH3)2 | H | S | CH(CH3)CH2CH3 |
A-474 | CH(CH3)2 | H | S | CH2CH2(CH3)2 |
A-475 | CH(CH3)2 | H | S | C(CH3)3 |
A-476 | CH(CH3)2 | H | S | C(S)CH3 |
A-477 | CH(CH3)2 | H | S | C(S)CH2CH3 |
A-478 | CH(CH3)2 | CH(CH3)2 | S | H |
A-479 | CH(CH3)2 | CH(CH3)2 | S | CH3 |
A-480 | CH(CH3)2 | CH(CH3)2 | S | CH2CH3 |
A-481 | CH(CH3)2 | CH(CH3)2 | S | CH2CH2CH3 |
A-482 | CH(CH3)2 | CH(CH3)2 | S | CH(CH3)2 |
A-483 | CH(CH3)2 | CH(CH3)2 | S | CH2CH2CH2CH3 |
A-484 | CH(CH3)2 | CH(CH3)2 | S | CH(CH3)CH2CH3 |
A-485 | CH(CH3)2 | CH(CH3)2 | S | CH2CH2(CH3)2 |
A-486 | CH(CH3)2 | CH(CH3)2 | S | C(CH3)3 |
A-487 | CH(CH3)2 | CH(CH3)2 | S | C(S)CH3 |
A-488 | CH(CH3)2 | CH(CH3)2 | S | C(S)CH2CH3 |
A-489 | C(CH3)3 | H | S | H |
A-490 | C(CH3)3 | H | S | CH3 |
A-491 | C(CH3)3 | H | S | CH2CH3 |
A-492 | C(CH3)3 | H | S | CH2CH2CH3 |
A-493 | C(CH3)3 | H | S | CH(CH3)2 |
A-494 | C(CH3)3 | H | S | CH2CH2CH2CH3 |
A-495 | C(CH3)3 | H | S | CH(CH3)CH2CH3 |
A-496 | C(CH3)3 | H | S | CH2CH2(CH3)2 |
A-497 | C(CH3)3 | H | S | C(CH3)3 |
A-498 | C(CH3)3 | H | S | C(S)CH3 |
A-499 | C(CH3)3 | H | S | C(S)CH2CH3 |
A-500 | CH(CH2CH3)2 | H | S | H |
A-501 | CH(CH2CH3)2 | H | S | CH3 |
A-502 | CH(CH2CH3)2 | H | S | CH2CH3 |
A-503 | CH(CH2CH3)2 | H | S | CH2CH2CH3 |
A-504 | CH(CH2CH3)2 | H | S | CH(CH3)2 |
A-505 | CH(CH2CH3)2 | H | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-506 | CH(CH2CH3)2 | H | S | CH(CH3)CH2CH3 |
A-507 | CH(CH2CH3)2 | H | S | CH2CH2(CH3)2 |
A-508 | CH(CH2CH3)2 | H | S | C(CH3)3 |
A-509 | CH(CH2CH3)2 | H | S | C(S)CH3 |
A-510 | CH(CH2CH3)2 | H | S | C(S)CH2CH3 |
A-511 | c-C3H5 | H | S | H |
A-512 | c-C3H5 | H | S | CH3 |
A-513 | c-C3H5 | H | S | CH2CH3 |
A-514 | c-C3H5 | H | S | CH2CH2CH3 |
A-515 | c-C3H5 | H | S | CH(CH3)2 |
A-516 | c-C3H5 | H | S | CH2CH2CH2CH3 |
A-517 | c-C3H5 | H | S | CH(CH3)CH2CH3 |
A-518 | c-C3H5 | H | S | CH2CH2(CH3)2 |
A-519 | c-C3H5 | H | S | C(CH3)3 |
A-520 | c-C3H5 | H | S | C(S)CH3 |
A-521 | c-C3H5 | H | S | C(S)CH2CH3 |
A-522 | c-C3H5 | CH3 | S | H |
A-523 | c-C3H5 | CH3 | S | CH3 |
A-524 | c-C3H5 | CH3 | S | CH2CH3 |
A-525 | c-C3H5 | CH3 | S | CH2CH2CH3 |
A-526 | c-C3H5 | CH3 | S | CH(CH3)2 |
A-527 | c-C3H5 | CH3 | S | CH2CH2CH2CH3 |
A-528 | c-C3H5 | CH3 | S | CH(CH3)CH2CH3 |
A-529 | c-C3H5 | CH3 | S | CH2CH2(CH3)2 |
A-530 | c-C3H5 | CH3 | S | C(CH3)3 |
A-531 | c-C3H5 | CH3 | S | C(S)CH3 |
A-532 | c-C3H5 | CH3 | S | C(S)CH2CH3 |
A-533 | c-C5H9 | H | S | H |
A-534 | c-C5H9 | H | S | CH3 |
A-535 | c-C5H9 | H | S | CH2CH3 |
A-536 | c-C5H9 | H | S | CH2CH2CH3 |
A-537 | c-C5H9 | H | S | CH(CH3)2 |
A-538 | c-C5H9 | H | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-539 | c-C5H9 | H | S | CH(CH3)CH2CH3 |
A-540 | c-C5H9 | H | S | CH2CH2(CH3)2 |
A-541 | c-C5H9 | H | S | C(CH3)3 |
A-542 | c-C5H9 | H | S | C(S)CH3 |
A-543 | c-C5H9 | H | S | C(S)CH2CH3 |
A-544 | c-C5H9 | CH3 | S | H |
A-545 | c-C5H9 | CH3 | S | CH3 |
A-546 | c-C5H9 | CH3 | S | CH2CH3 |
A-547 | c-C5H9 | CH3 | S | CH2CH2CH3 |
A-548 | c-C5H9 | CH3 | S | CH(CH3)2 |
A-549 | c-C5H9 | CH3 | S | CH2CH2CH2CH3 |
A-550 | c-C5H9 | CH3 | S | CH(CH3)CH2CH3 |
A-551 | c-C5H9 | CH3 | S | CH2CH2(CH3)2 |
A-552 | c-C5H9 | CH3 | S | C(CH3)3 |
A-553 | c-C5H9 | CH3 | S | C(S)CH3 |
A-554 | c-C5H9 | CH3 | S | C(S)CH2CH3 |
A-555 | -CH2CH2- | S | H | |
A-556 | CH2CH2 | S | CH3 | |
A-557 | CH2CH2 | S | CH2CH3 | |
A-558 | CH2CH2 | S | CH2CH2CH3 | |
A-559 | CH2CH2 | S | CH(CH3)2 | |
A-560 | CH2CH2 | S | CH2CH2CH2CH3 | |
A-561 | CH2CH2 | S | CH(CH3)CH2CH3 | |
A-562 | CH2CH2 | S | CH2CH2(CH3)2 | |
A-563 | CH2CH2 | S | C(CH3)3 | |
A-564 | CH2CH2 | S | C(S)CH3 | |
A-565 | CH2CH2 | S | C(S)CH2CH3 | |
A-566 | -CH2CH2CH2CH2- | S | H | |
A-567 | -CH2CH2CH2CH2- | S | CH3 | |
A-568 | -CH2CH2CH2CH2- | S | CH2CH3 | |
A-569 | -CH2CH2CH2CH2- | S | CH2CH2CH3 | |
A-570 | -CH2CH2CH2CH2- | S | CH(CH3)2 | |
A-571 | -CH2CH2CH2CH2- | S | CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
A-572 | -CH2CH2CH2CH2- | S | CH(CH3)CH2CH3 | |
A-573 | -CH2CH2CH2CH2- | S | CH2CH2(CH3)2 | |
A-574 | -CH2CH2CH2CH2- | S | C(CH3)3 | |
A-575 | -CH2CH2CH2CH2- | S | C(S)CH3 | |
A-576 | -CH2CH2CH2CH2- | S | C(S)CH2CH3 |
表B
序号 | R2 | R3 | Y | Z |
B-1 | CH3 | H | O | OCH3 |
B-2 | CH3 | H | O | OCH2CH3 |
B-3 | CH3 | H | O | OCH2CH2CH3 |
B-4 | CH3 | H | O | OCH(CH3)2 |
B-5 | CH3 | H | O | OCH2CH2CH2CH3 |
B-6 | CH3 | H | O | OCH2CH(CH3)2 |
B-7 | CH3 | H | O | OCH(CH3)CH2CH3 |
B-8 | CH3 | H | O | OC(CH3)3 |
B-9 | CH3 | H | O | OCH2CH2CH2CH2CH3 |
B-10 | CH3 | H | O | NH2 |
B-11 | CH3 | H | O | NHCH3 |
B-12 | CH3 | H | O | NHCH2CH3 |
B-13 | CH3 | H | O | NHCH2CH2CH3 |
B-14 | CH3 | H | O | NHCH(CH3)2 |
B-15 | CH3 | H | O | NHCH2CH2CH2CH3 |
B-16 | CH3 | H | O | N(CH3)x |
B-17 | CH3 | H | O | N(CH3)CH2CH3 |
B-18 | CH3 | H | O | N(CH3)CH2CH2CH3 |
B-19 | CH3 | H | O | N(CH3)CH(CH3)2 |
B-20 | CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-21 | CH3 | H | O | N(CH2CH3)2 |
B-22 | CH3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-23 | CH3 | H | O | N(CH3)CH(CH3)2 |
B-24 | CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
B-25 | CH3 | H | O | N(CH2CH2CH3)2 |
B-26 | CH3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-27 | CH3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-28 | CH3 | H | O | N(CH2CH2CH2CH3)2 |
B-29 | CH3 | H | O | N(-CH2CH2OCH2CH2-) |
B-30 | CH3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-31 | CH3 | CH3 | O | OCH3 |
B-32 | CH3 | CH3 | O | OCH2CH3 |
B-33 | CH3 | CH3 | O | OCH2CH2CH3 |
B-34 | CH3 | CH3 | O | O CH(CH3)2 |
B-35 | CH3 | CH3 | O | OCH2CH2CH2CH3 |
B-36 | CH3 | CH3 | O | OCH2CH(CH3)2 |
B-37 | CH3 | CH3 | O | OCH(CH3)CH2CH3 |
B-38 | CH3 | CH3 | O | OC(CH3)3 |
B-39 | CH3 | CH3 | O | OCH2CH2CH2CH2CH3 |
B-40 | CH3 | CH3 | O | NH2 |
B-41 | CH3 | CH3 | O | NHCH3 |
B-42 | CH3 | CH3 | O | NHCH2CH3 |
B-43 | CH3 | CH3 | O | NHCH2CH2CH3 |
B-44 | CH3 | CH3 | O | NHCH(CH3)2 |
B-45 | CH3 | CH3 | O | NHCH2CH2CH2CH3 |
B-46 | CH3 | CH3 | O | N(CH3)2 |
B-47 | CH3 | CH3 | O | N(CH3)CH2CH3 |
B-48 | CH3 | CH3 | O | N(CH3)CH2CH2CH3 |
B-49 | CH3 | CH3 | O | N(CH3)CH(CH3)2 |
B-50 | CH3 | CH3 | O | N(CH3)CH2CH2CH2CH3 |
B-51 | CH3 | CH3 | O | N(CH2 CH3)2 |
B-52 | CH3 | CH3 | O | N(CH2CH3)CH2CH2CH3 |
B-53 | CH3 | CH3 | O | N(CH3)CH(CH3)2 |
B-54 | CH3 | CH3 | O | N(CH3)CH2CH2CH2CH3 |
B-55 | CH3 | CH3 | O | N(CH2CH2CH3)2 |
B-56 | CH3 | CH3 | O | N(CH2CH2CH3)CH(CH3)2 |
B-57 | CH3 | CH3 | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
B-58 | CH3 | CH3 | O | N(CH2CH2CH2CH3)2 |
B-59 | CH3 | CH3 | O | N(-CH2CH2OCH2CH2-) |
B-60 | CH3 | CH3 | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-61 | CH2CH3 | H | O | OCH3 |
B-62 | CH2CH3 | H | O | OCH2CH3 |
B-63 | CH2CH3 | H | O | OCH2CH2CH3 |
B-64 | CH2CH3 | H | O | O CH(CH3)2 |
B-65 | CH2CH3 | H | O | OCH2CH2CH2CH3 |
B-66 | CH2CH3 | H | O | OCH2CH(CH3)2 |
B-67 | CH2CH3 | H | O | OCH(CH3)CH2CH3 |
B-68 | CH2CH3 | H | O | OC(CH3)3 |
B-69 | CH2CH3 | H | O | OCH2CH2CH2CH2CH3 |
B-70 | CH2CH3 | H | O | NH2 |
B-71 | CH2CH3 | H | O | NHCH3 |
B-72 | CH2CH3 | H | O | NHCH2CH3 |
B-73 | CH2CH3 | H | O | NHCH2 CH2 CH3 |
B-74 | CH2CH3 | H | O | NHCH(CH3)2 |
B-75 | CH2CH3 | H | O | NHCH2CH2CH2CH3 |
B-76 | CH2CH3 | H | O | N(CH3)2 |
B-77 | CH2CH3 | H | O | N(CH3)CH2CH3 |
B-78 | CH2CH3 | H | O | N(CH3)CH2CH2CH3 |
B-79 | CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-80 | CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-81 | CH2CH3 | H | O | N(CH2CH3)2 |
B-82 | CH2CH3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-83 | CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-84 | CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-85 | CH2CH3 | H | O | N(CH2CH2CH3)2 |
B-86 | CH2CH3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-87 | CH2CH3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-88 | CH2CH3 | H | O | N(CH2CH2CH2CH3)2 |
B-89 | CH2CH3 | H | O | N(-CH2CH2OCH2CH2-) |
B-90 | CH2CH3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
序号 | R2 | R3 | Y | Z |
B-91 | CH2CH2CH3 | H | O | OCH3 |
B-92 | CH2CH2CH3 | H | O | OCH2CH3 |
B-93 | CH2CH2CH3 | H | O | OCH2CH2CH3 |
B-94 | CH2CH2CH3 | H | O | OCH(CH3)2 |
B-95 | CH2CH2CH3 | H | O | OCH2CH2CH2CH3 |
B-96 | CH2CH2CH3 | H | O | OCH2 CH(CH3)2 |
B-97 | CH2CH2CH3 | H | O | OCH(CH3)CH2CH3 |
B-98 | CH2CH2CH3 | H | O | OC(CH3)3 |
B-99 | CH2CH2CH3 | H | O | OCH2CH2CH2CH2CH3 |
B-100 | CH2CH2CH3 | H | O | NH2 |
B-101 | CH2CH2CH3 | H | O | NHCH3 |
B-102 | CH2CH2CH3 | H | O | NHCH2CH3 |
B-103 | CH2CH2CH3 | H | O | NHCH2CH2CH3 |
B-104 | CH2CH2CH3 | H | O | NHCH(CH3)2 |
B-105 | CH2CH2CH3 | H | O | NHCH2CH2CH2CH3 |
B-106 | CH2CH2CH3 | H | O | N(CH3)2 |
B-107 | CH2CH2CH3 | H | O | N(CH3)CH2CH3 |
B-108 | CH2CH2CH3 | H | O | N(CH3)CH2CH2CH3 |
B-109 | CH2CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-110 | CH2CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-111 | CH2CH2CH3 | H | O | N(CH2CH3)2 |
B-112 | CH2CH2CH3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-113 | CH2CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-114 | CH2CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-115 | CH2CH2CH3 | H | O | N(CH2CH2CH3)2 |
B-116 | CH2CH2CH3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-117 | CH2CH2CH3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-118 | CH2CH2CH3 | H | O | N(CH2CH2CH2CH3)2 |
B-119 | CH2CH2CH3 | H | O | N(-CH2CH2OCH2CH2-) |
B-120 | CH2CH2CH3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-121 | CH(CH3)2 | H | O | OCH3 |
B-122 | CH(CH3)2 | H | O | OCH2CH3 |
B-123 | CH(CH3)2 | H | O | OCH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
B-124 | CH(CH3)2 | H | O | OCH(CH3)2 |
B-125 | CH(CH3)2 | H | O | OCH2CH2CH2CH3 |
B-126 | CH(CH3)2 | H | O | OCH2CH(CH3)2 |
B-127 | CH(CH3)2 | H | O | OCH(CH3)CH2CH3 |
B-128 | CH(CH3)2 | H | O | OC(CH3)3 |
B-129 | CH(CH3)2 | H | O | OCH2CH2CH2CH2CH3 |
B-130 | CH(CH3)2 | H | O | NH2 |
B-131 | CH(CH3)2 | H | O | NHCH3 |
B-132 | CH(CH3)2 | H | O | NHCH2CH3 |
B-133 | CH(CH3)2 | H | O | NHCH2CH2CH3 |
B-134 | CH(CH3)2 | H | O | NHCH(CH3)2 |
B-135 | CH(CH3)2 | H | O | NHCH2CH2CH2CH3 |
B-136 | CH(CH3)2 | H | O | N(CH3)2 |
B-137 | CH(CH3)2 | H | O | N(CH3)CH2CH3 |
B-138 | CH(CH3)2 | H | O | N(CH3)CH2CH2CH3 |
B-139 | CH(CH3)2 | H | O | N(CH3)CH(CH3)2 |
B-140 | CH(CH3)2 | H | O | N(CH3)CH2CH2CH2CH3 |
B-141 | CH(CH3)2 | H | O | N(CH2CH3)2 |
B-142 | CH(CH3)2 | H | O | N(CH2CH3)CH2CH2CH3 |
B-143 | CH(CH3)2 | H | O | N(CH3)CH(CH3)2 |
B-144 | CH(CH3)2 | H | O | N(CH3)CH2CH2CH2CH3 |
B-145 | CH(CH3)2 | H | O | N(CH2CH2CH3)2 |
B-146 | CH(CH3)2 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-147 | CH(CH3)2 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-148 | CH(CH3)2 | H | O | N(CH2CH2CH2CH3)2 |
B-149 | CH(CH3)2 | H | O | N(-CH2CH2OCH2CH2-) |
B-150 | CH(CH3)2 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-151 | CH2CH2CH2CH3 | H | O | OCH3 |
B-152 | CH2CH2CH2CH3 | H | O | OCH2CH3 |
B-153 | CH2CH2CH2CH3 | H | O | OCH2CH2CH3 |
B-154 | CH2CH2CH2CH3 | H | O | OCH(CH3)2 |
B-155 | CH2CH2CH2CH3 | H | O | OCH2CH2CH2CH3 |
B-156 | CH2CH2CH2CH3 | H | O | OCH2CH(CH3)2 |
序号 | R2 | R3 | Y | Z |
B-157 | CH2CH2CH2CH3 | H | O | OCH(CH3)CH2CH3 |
B-158 | CH2CH2CH2CH3 | H | O | OC(CH3)3 |
B-159 | CH2CH2CH2CH3 | H | O | OCH2CH2CH2CH2CH3 |
B-160 | CH2CH2CH2CH3 | H | O | NH2 |
B-161 | CH2CH2CH2CH3 | H | O | NHCH3 |
B-162 | CH2CH2CH2CH3 | H | O | NHCH2CH3 |
B-163 | CH2CH2CH2CH3 | H | O | NHCH2CH2CH3 |
B-164 | CH2CH2CH2CH3 | H | O | NHCH(CH3)2 |
B-165 | CH2CH2CH2CH3 | H | O | NHCH2CH2CH2CH3 |
B-166 | CH2CH2CH2CH3 | H | O | N(CH3)2 |
B-167 | CH2CH2CH2CH3 | H | O | N(CH3)CH2CH3 |
B-168 | CH2CH2CH2CH3 | H | O | N(CH3)CH2CH2CH3 |
B-169 | CH2CH2CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-170 | CH2CH2CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-171 | CH2CH2CH2CH3 | H | O | N(CH2CH3)2 |
B-172 | CH2CH2CH2CH3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-173 | CH2CH2CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-174 | CH2CH2CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-175 | CH2CH2CH2CH3 | H | O | N(CH2CH2CH3)2 |
B-176 | CH2CH2CH2CH3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-177 | CH2CH2CH2CH3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-178 | CH2CH2CH2CH3 | H | O | N(CH2CH2CH2CH3)2 |
B-179 | CH2CH2CH2CH3 | H | O | N(-CH2CH2OCH2CH2-) |
B-180 | CH2CH2CH2CH3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-181 | C(CH3)3 | H | O | OCH3 |
B-182 | C(CH3)3 | H | O | OCH2CH3 |
B-183 | C(CH3)3 | H | O | OCH2CH2CH3 |
B-184 | C(CH3)3 | H | O | OCH(CH3)2 |
B-185 | C(CH3)3 | H | O | OCH2CH2CH2CH3 |
B-186 | C(CH3)3 | H | O | OCH2CH(CH3)2 |
B-187 | C(CH3)3 | H | O | OCH(CH3)CH2CH3 |
B-188 | C(CH3)3 | H | O | OC(CH3)3 |
B-189 | C(CH3)3 | H | O | OCH2CH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
B-190 | C(CH3)3 | H | O | NH2 |
B-191 | C(CH3)3 | H | O | NHCH3 |
B-192 | C(CH3)3 | H | O | NHCH2CH3 |
B-193 | C(CH3)3 | H | O | NHCH2CH2CH3 |
B-194 | C(CH3)3 | H | O | NHCH(CH3)2 |
B-195 | C(CH3)3 | H | O | NHCH2CH2CH2CH3 |
B-196 | C(CH3)3 | H | O | N(CH3)2 |
B-197 | C(CH3)3 | H | O | N(CH3)CH2CH3 |
B-198 | C(CH3)3 | H | O | N(CH3)CH2CH2CH3 |
B-199 | C(CH3)3 | H | O | N(CH3)CH(CH3)2 |
B-200 | C(CH3)3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-201 | C(CH3)3 | H | O | N(CH2CH3)2 |
B-202 | C(CH3)3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-203 | C(CH3)3 | H | O | N(CH3)CH(CH3)2 |
B-204 | C(CH3)3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-205 | C(CH3)3 | H | O | N(CH2CH2CH3)2 |
B-206 | C(CH3)3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-207 | C(CH3)3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-208 | C(CH3)3 | H | O | N(CH2 CH2 CH2 CH3)2 |
B-209 | C(CH3)3 | H | O | N(-CH2CH2OCH2CH2-) |
B-210 | C(CH3)3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-211 | C(CH3)CH2CH3 | H | O | OCH3 |
B-212 | C(CH3)CH2CH3 | H | O | OCH2CH3 |
B-213 | C(CH3)CH2CH3 | H | O | OCH2CH2CH3 |
B-214 | C(CH3)CH2CH3 | H | O | OCH(CH3)2 |
B-215 | C(CH3)CH2CH3 | H | O | OCH2CH2CH2CH3 |
B-216 | C(CH3)CH2CH3 | H | O | OCH2CH(CH3)2 |
B-217 | C(CH3)CH2CH3 | H | O | OCH(CH3)CH2CH3 |
B-218 | C(CH3)CH2CH3 | H | O | OC(CH3)3 |
B-219 | C(CH3)CH2 CH3 | H | O | OCH2CH2CH2CH2CH3 |
B-220 | C(CH3)CH2CH3 | H | O | NH2 |
B-221 | C(CH3)CH2CH3 | H | O | NHCH3 |
B-222 | C(CH3)CH2CH3 | H | O | NHCH2CH3 |
序号 | R2 | R3 | Y | Z |
B-223 | C(CH3)CH2CH3 | H | O | NHCH2CH2CH3 |
B-224 | C(CH3)CH2CH3 | H | O | NHCH(CH3)2 |
B-225 | C(CH3)CH2CH3 | H | O | NHCH2CH2CH2CH3 |
B-226 | C(CH3)CH2CH3 | H | O | N(CH3)2 |
B-227 | C(CH3)CH2CH3 | H | O | N(CH3)CH2CH3 |
B-228 | C(CH3)CH2CH3 | H | O | N(CH3)CH2CH2CH3 |
B-229 | C(CH3)CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-230 | C(CH3)CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-231 | C(CH3)CH2CH3 | H | O | N(CH2CH3)2 |
B-232 | C(CH3)CH2CH3 | H | O | N(CH2CH3)CH2CH2CH3 |
B-233 | C(CH3)CH2CH3 | H | O | N(CH3)CH(CH3)2 |
B-234 | C(CH3)CH2CH3 | H | O | N(CH3)CH2CH2CH2CH3 |
B-235 | C(CH3)CH2CH3 | H | O | N(CH2 CH2 CH3)2 |
B-236 | C(CH3)CH2CH3 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-237 | C(CH3)CH2CH3 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-238 | C(CH3)CH2CH3 | H | O | N(CH2CH2CH2CH3)2 |
B-239 | C(CH3)CH2CH3 | H | O | N(-CH2CH2OCH2CH2-) |
B-240 | C(CH3)CH2CH3 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
B-241 | CH2CH(CH3)2 | H | O | OCH3 |
B-242 | CH2CH(CH3)2 | H | O | OCH2CH3 |
B-243 | CH2CH(CH3)2 | H | O | OCH2CH2CH3 |
B-244 | CH2CH(CH3)2 | H | O | OCH(CH3)2 |
B-245 | CH2CH(CH3)2 | H | O | OCH2CH2CH2CH3 |
B-246 | CH2CH(CH3)2 | H | O | OCH2CH(CH3)2 |
B-247 | CH2CH(CH3)2 | H | O | OCH(CH3)CH2CH3 |
B-248 | CH2CH(CH3)2 | H | O | OC(CH3)3 |
B-249 | CH2CH(CH3)2 | H | O | OCH2CH2CH2CH2CH3 |
B-250 | CH2CH(CH3)2 | H | O | NH2 |
B-251 | CH2CH(CH3)2 | H | O | NHCH3 |
B-252 | CH2CH(CH3)2 | H | O | NHCH2CH3 |
B-253 | CH2 CH(CH3)2 | H | O | NHCH2CH2CH3 |
B-254 | CH2CH(CH3)2 | H | O | NHCH(CH3)2 |
B-255 | CH2CH(CH3)2 | H | O | NHCH2CH2CH2CH3 |
序号 | R2 | R3 | Y | Z |
B-256 | CH2CH(CH3)2 | H | O | N(CH3)2 |
B-257 | CH2 CH(CH3)2 | H | O | N(CH3)CH2CH3 |
B-258 | CH2CH(CH3)2 | H | O | N(CH3)CH2CH2CH3 |
B-259 | CH2CH(CH3)2 | H | O | N(CH3)CH(CH3)2 |
B-260 | CH2 CH(CH3)2 | H | O | N(CH3)CH2CH2CH2CH3 |
B-261 | CH2CH(CH3)2 | H | O | N(CH2CH3)2 |
B-262 | CH2 CH(CH3)2 | H | O | N(CH2CH3)CH2CH2CH3 |
B-263 | CH2CH(CH3)2 | H | O | N(CH3)CH(CH3)2 |
B-264 | CH2CH(CH3)2 | H | O | N(CH3)CH2CH2CH2CH3 |
B-265 | CH2CH(CH3)2 | H | O | N(CH2CH2CH3)2 |
B-266 | CH2CH(CH3)2 | H | O | N(CH2CH2CH3)CH(CH3)2 |
B-267 | CH2CH(CH3)2 | H | O | N(CH2CH2CH3)CH2CH2CH2CH3 |
B-268 | CH2CH(CH3)2 | H | O | N(CH2CH2CH2CH3)2 |
B-269 | CH2CH(CH3)2 | H | O | N(-CH2CH2OCH2CH2-) |
B-270 | CH2CH(CH3)2 | H | O | N(-CH2CH2N[CH3]CH2CH2-) |
化合物I适于作为杀真菌剂。它们对宽范围的植物病原性真菌具有显著效力,所述真菌尤其选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、卵菌纲(Oomycetes)和担子菌纲(Basidiomycetes)真菌。它们中的一些内吸有效并可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于植物保护中。
本发明进一步涉及本发明式I化合物和/或其可药用盐的药物应用,尤其是它们在哺乳动物如人类中治疗肿瘤的应用。
它们对在各种栽培植物如小麦、黑麦、大麦、燕麦、稻、玉米、禾草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果和观赏植物以及蔬菜如黄瓜、豆类、西红柿、土豆和葫芦科植物以及这些植物的种子中防治大量真菌尤其重要。
它们尤其适于防治下列植物病害:
·蔬菜、油菜籽、糖用甜菜、水果和稻上的链格孢(Alternaria)属,
·糖用甜菜和蔬菜上的丝囊霉(Aphanomyces)属,
·玉米、禾谷类、稻和草坪中的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属,
·禾谷类中的禾白粉菌(Blumeria graminis)(白粉病),
·草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
·莴苣上的莴苣盘梗霉(Bremia lactucae),
·玉米、大豆、稻和糖用甜菜上的尾孢(Cercospora)属,
·玉米、禾谷类、稻上的旋孢腔菌(Cochliobolus)属(例如禾谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolusmiyabeanus)),
·大豆和棉花上的剌盘孢(Colletotricum)属,
·禾谷类和玉米上的内脐蠕孢(Drechslera)属,
·玉米上的突脐蠕孢(Exserohilum)属,
·葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳(Sphaerotheca fuliginea),
·各种植物上的镰孢霉(Fusarium)属和轮枝孢(Verticillium)属,
·禾谷类上的禾顶囊壳(Gaeumanomyces graminis)属,
·禾谷类和稻上的赤霉(Gibberella)属(例如稻上的藤仓赤霉(Gibberellafujikuroi)),
·稻上的Grainstaining complex,
·玉米和稻上的长蠕孢(Helminthosporium)属,
·禾谷类上的Michrodochium nivale,
·禾谷类、香蕉和花生上的球腔菌(Mycosphaerella)属,
·大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.meibomiae),
·大豆和向日葵上的拟茎点霉(Phomopsis)属,
·土豆和西红柿上的致病疫霉(Phytophthora infestans),
·葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
·苹果上的苹果白粉病菌(Podosphaera leucotricha),
·禾谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
·啤酒花和葫芦科植物上的假霜霉(Pseudoperonospora)属,
·禾谷类和玉米上的柄锈菌(Puccinia)属,
·禾谷类上的核腔菌(Pyrenophora)属,
·稻上的稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticium sasakii)、帚梗柱孢属(Sarocladium oryzae)、稻叶鞘腐败病(S.attenuatum)、稻叶黑粉菌(Entyloma oryzae),
·草坪和禾谷类上的稻梨孢菌(Pyricularia grisea),
·草坪、稻、玉米、棉花、油菜籽、向日葵、糖用甜菜、蔬菜和其他植物上的腐霉(Pythium)属,
·棉花、稻、土豆、草坪、玉米、油菜籽、土豆、糖用甜菜、蔬菜和其他植物上的丝核菌(Rhizoctonia)属,
·油菜籽和向日葵上的核盘菌(Sclerotinia)属,
·小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
·葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinula)necator),
·玉米和草坪上的Setospaeria属,
·玉米上的丝轴黑粉菌(Sphacelotheca reilinia),
·大豆和棉花上的根串珠霉(Thievaliopsis)属,
·禾谷类上的腥黑粉菌(Tilletia)属,
·禾谷类、玉米和糖用甜菜上的黑粉菌(Ustilago)属,以及
·苹果和梨上的黑星菌(Venturia)属(黑星病)。
化合物I还适于防治有害真菌如拟青霉(Paecilomyces variotii)以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。
化合物I通过用杀真菌有效量的活性化合物处理真菌或需要防止真菌侵袭的植物、种子、材料或土壤而使用。施用可以在材料、植物或种子被真菌侵染之前和之后进行。
杀真菌组合物通常包含0.1-95重量%,优选0.5-90重量%的活性化合物。
当用于植物保护时,施用量取决于所需效果的种类为0.01-2.0kg活性化合物/公顷。
在种子处理,例如对种子撒粉、涂覆或浸渍时,活性化合物的用量通常为1-1000g/100kg种子,优选1-200g/100kg,尤其是5-100g/100kg。
当用于保护材料或储藏产品时,活性化合物的施用量取决于施用区域的类型和所需效果。在保护材料中通常施用的量例如每m3处理材料为0.001g-2kg,优选0.005g-1kg活性化合物。
式I化合物可以以同样形成本发明主题的各种晶型存在。
可以将化合物I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。施用形式取决于特定目的;在每种情况下都应确保本发明化合物精细和均匀地分布。
种子处理用配制剂可以进一步包含粘合剂和/或胶凝剂以及合适的话染料。
可以加入粘合剂以增加处理之后的活性化合物对种子的粘附。合适的粘合剂例如为EO/PO嵌段共聚物表面活性剂,还有聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺(Lupasol、Polymin)、聚醚、聚氨酯、聚乙酸乙烯酯、Tylose和这些聚合物的共聚物。合适的胶凝剂例如为角叉菜(Satiagel)。
配制剂以已知方式制备,例如通过将活性化合物与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。适于该目的的溶剂/助剂主要为:
-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。
-载体如磨碎的天然矿物(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);乳化剂如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)以及分散剂如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-甲基吡咯烷酮和水。
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、脲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。活性化合物以90-100%,优选95-100%的纯度(根据NMR谱)使用。
对于种子处理,所述配制剂在稀释2-10倍时在即用制剂中产生的活性化合物浓度为0.01-60重量%,优选0.1-40重量%。
下列为配制剂实例:
1.用水稀释的产品
A)水溶性浓缩物(SL、LS)
将10重量份本发明化合物溶于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。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重量份本发明化合物溶于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。活性化合物浓度为20重量%。
C)乳油(EC)
将15重量份本发明化合物溶于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%)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D)乳液(EW、EO、ES)
将25重量份本发明化合物溶于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%)。借助乳化机(如Ultraturrax)将该混合物引入水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份本发明化合物粉碎并加入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。该配制剂中活性化合物含量为20重量%。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份本发明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。该配制剂的活性化合物含量为50重量%。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份本发明化合物在转子-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。该配制剂的活性化合物含量为75重量%。
H)凝胶配制剂
将20重量份本发明化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂球磨成细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I)可撒粉粉末(DP、DS)
将5重量份本发明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。
J)颗粒(GR、FG、GG、MG)
将0.5重量份本发明合物细碎研磨并结合95.5重量份载体。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活性化合物含量为0.5重量%的颗粒。
K)ULV溶液(UL)
将10重量份本发明化合物溶于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。
种子处理通常利用水溶性浓缩物(LS)、悬浮液(FS)、粉剂(DS)、水分散性和水溶性粉末(WS、SS)、乳液(ES)、乳油(EC)和凝胶配制剂(GF)。这些配制剂可以直接或优选稀释后施用于种子上。施用可以在播种前进行。
优选将FS配制剂用于种子处理。该类配制剂通常包含1-800g/L活性化合物、1-200g/L表面活性剂、0-200g/L防冻剂、0-400g/L粘合剂、0-200g/L染料和溶剂,优选水。
活性化合物可以直接、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、撒播用材料或颗粒形式),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;它们意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳油、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。或者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。
即用制剂中的活性化合物浓度可在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物也可成功用于超低容量法(ULV),其中可以施用包含超过95重量%活性化合物的配制剂,或甚至施用不含添加剂的活性化合物。
各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂都可加入活性化合物中,若合适的话,恰在紧邻使用前加入(桶混合)。这些试剂通常与本发明试剂以1∶10-10∶1的重量比混合。
在作为杀真菌剂的使用形式中,本发明组合物还可与其它活性化合物一起存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将作为杀真菌剂使用的化合物I或包含它们的组合物与其它活性化合物,尤其是其他杀真菌剂混合时,在许多情况下可以拓宽活性谱或防止产生耐受性。在许多情况下得到协同增效作用。
下列本发明化合物可以与其结合使用的杀真菌剂用来说明可能的组合但不限制它们:
·酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(oxadixyl),
·胺衍生物,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺茂胺(spiroxamine)或克啉菌(tridemorph),
·苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinyl),
·抗菌素,例如放线菌酮(cycloheximide)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin),
·唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、烯菌灵(enilconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafole)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)或戊叉唑菌(triticonazole),
·二羧酰亚胺类,如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin),
·二硫代氨基甲酸盐类,如福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)或代森锌(zineb),
·杂环化合物,如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、吡噻菌胺(penthiopyrad)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyelazole)或嗪氨灵(triforine),N-(4’-溴联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺,N-(4’-三氟甲基联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺,N-(4’-氯-3’-氟联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺,N-(3’,4’-二氯-4-氟联苯-2-基)-3-二氟甲基-1-甲基吡唑-4-甲酰胺,N-(2-氰基苯基)-3,4-二氯异噻唑-5-甲酰胺,5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮,N-二甲基-3-(3-溴-6-氟-2-甲基吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酰胺,
·铜杀真菌剂,如波尔多液(Bordeaux混合物)、醋酸铜、王铜(copperoxychloride)或碱式硫酸铜,
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrophthal-isopropyl),
·苯基吡咯类,如拌种咯(fenpiclonil)或氟菌(fludioxonil),
·硫,
·其它杀真菌剂,如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、哒菌清(diclomezine)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(tluazinam)、藻菌磷(fosetyl)、藻菌磷(fosetyl-aluminum)、亚磷酸及其盐、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、双炔酰菌胺(mandipropamide)、苯菌酮(metrafenone)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)或苯酰菌胺(zoxamide),N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-甲基磺酰基氨基-3-甲基丁酰胺、N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-乙基磺酰基氨基-3-甲基丁酰胺、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶、3-(4-氯苯基)-3-(2-异丙氧基羰基氨基-3-甲基丁酰氨基)丙酸甲酯、N-(1-(1-(4-氰基苯基)乙基磺酰基)丁-2-基)氨基甲酸4-氟苯基酯,
·嗜球果伞素类(strobilurins),如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)或肟菌酯(trifloxystrobin),
·次磺酸衍生物,如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)或对甲抑菌灵(tolylfluanid),
·肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
合成实施例:
通过适当改变原料而使用下列合成实施例所述的程序得到其他化合物I。如此得到的化合物与物理数据一起列于下表中。
实施例1-制备2-[5-氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基氨基]丁-1-醇
将1.57mmol三乙胺和1.57mmol 2-氨基丁-1-醇加入500mg(1.57mmol)5,7-二氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶在4ml二氯甲烷中的溶液中,然后将该溶液在20-25℃下搅拌约15小时。然后将该溶液用0.SMHCl和浓度为5%的NaCl溶液萃取。将有机相干燥并除去溶剂。得到535mg熔点为76-77℃的浅黄色晶体标题化合物。
1H-NMR(CDCl3;δ,ppm):8.2(1H,s);6.85(2H,q);6.7(1H,宽,NH);3.85(1H,s,宽);3.7(2H,q);3.5(1H,s,宽);1.65(1H,m);1.55(1H,m);0.8(3H,t)。
实施例2-制备乙酸2-[5-氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基氨基]丁基酯
将各0.13mmol的三乙胺、乙酸酐和4-N,N-二甲基氨基吡啶加入50mg(0.13mmol)2-[5-氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基氨基]丁-1-醇(见实施例1)在2ml二氯甲烷中的溶液中。将该溶液在20-25℃下搅拌约5小时。然后将该溶液用0.5M HCl和浓度为5%的NaCl溶液萃取。将有机相干燥并除去溶剂。得到36mg熔点为39-42℃的浅黄色晶体标题化合物。
1H-NMR(CDCl3;δ,ppm):8.4(1H,s);6.9(2H,t);6.4(1H,宽,NH);4.05(2H,d);3.7(1H,宽);2.0(3H,s);1.55(2H,m);0.85(3H,t)。
实施例3-制备[5-氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基]-(1-乙氧基甲基丙基)胺
将0.05mmol碳酸铯和0.05mmol碘乙烷加入20mg(0.05mmol)2-[5-氯-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基氨基]丁-1-醇(见实施例1)在1ml丙酮中的溶液中,然后将该悬浮液在50℃下搅拌2小时。加入5ml二氯甲烷之后,将该混合物用0.5M HCl和浓度为5%的NaCl溶液萃取。将有机相干燥并除去溶剂。得到9mg无色油状标题化合物。
1H-NMR(CDCl3;δ,ppm):8.35(1H,s);6.85(2H,m);6.6(1H,宽,NH);3.5(1H,宽);3.45(2H,q);3.4(2H,d);1.65(1H,m);1.5(1H,m);1.1(3H,t);0.75(3H,t)。
下表中的HPLC保留时间(RT)使用RP-18柱Chromolith SpeedROD(来自德国Merck KgaA)在40℃下经5分钟测定,该测定使用的流动相是梯度为5∶95-95∶5的乙腈+0.1%三氟乙酸(TFA)/水+0.1%TFA。质谱使用四极电喷射离子化,80V(正模式)进行。
式I.1化合物:
表I
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z);熔点[℃];1H-NMR[δppm] |
I-1 | H | CH2CH3 | H | H | H | O | CH3 | Cl | 2,4,6-F3 | 3.35分钟,[386M+H]+ |
I-2 | H | CH2CH3 | H | H | H | O | CH2CH3 | Cl | 2,4,6-F3 | 3.60分钟;[400M+H]+ |
I-3 | H | CH3 | H | H | H | O | CH2CH3 | Cl | 2,4,6-F3 | 3.38分钟;[385M+H]+ |
I-4 | H | CH3 | H | H | H | O | C(CH3)3 | Cl | 2,4,6-F3 | 3.85分钟;[413M+H]+ |
I-5 | H | CH3 | H | H | H | O | CH2CH(CH3)2 | Cl | 2,4,6-F3 | 3.90分钟;[413M+H]+ |
I-6 | H | CH3 | H | H | H | O | CH2CH2CH3 | Cl | 2,4,6-F3 | 3.65分钟;[399M+H]+ |
I-7 | CH3 | CH2CH3 | H | H | H | O | CH3 | Cl | 2,4,6-F3 | 3.36分钟;[385M+H]+ |
I-8 | H | CH2CH3 | H | H | H | O | CH2CH3 | Cl | 2-Cl,6-F | 3.56分钟;[398M+H]+ |
I-9 | H | CH2CH3 | H | H | H | O | CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.54分钟;[410M+H]+ |
I-10 | H | CH(CH3)2 | H | H | H | O | H | Cl | 2,4,6-F3 | 2.95分钟;[385M+H]+ |
I-11 | H | CH3 | H | CH3 | H | O | H | Cl | 2,4,6-F3 | 2.79分钟;[371M+H]+ |
I-12 | H | C6H5 | H | H | H | O | H | Cl | 2,4,6-F3 | 3.06分钟;[419M+H]+ |
I-13 | H | CH3 | H | H | H | O | H | Cl | 2,4,6-F3 | 2.56分钟;[357M+H]+ |
I-14 | H | C(CH3)3 | H | H | H | O | H | Cl | 2,4,6-F3 | 呈S构型的C*R2R3,166-168℃ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃];1H-NMR[δppm] |
I-15 | H | CH2CH3 | H | H | H | O | H | Cl | 2,4,6-F3 | 2.81分钟;[371M+H]+ |
I-16 | H | CH3 | H | CH3 | CH3 | O | H | Cl | 2,4,6-F3 | 3.01分钟;[385M+H]+ |
I-17 | H | CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.13分钟;[413M+H]+ |
I-18 | H | CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.35分钟;[427M+H]+ |
I-19 | H | CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.55分钟;[441M+H]+ |
I-20 | H | CH(CH3)2 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.29分钟;[427M+H]+ |
I-21 | H | CH(CH3)2 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.50分钟;[441M+H]+ |
I-22 | H | CH(CH3)2 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.69分钟;[455M+H]+ |
I-23 | H | CH3 | H | CH3 | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.15分钟;[413M+H]+ |
I-24 | H | CH3 | H | CH3 | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.38分钟;[427M+H]+ |
I-25 | H | CH3 | H | CH3 | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.60分钟;[441M+H]+ |
I-26 | H | C6H5 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.37分钟;[461M+H]+ |
I-27 | H | C6H5 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.57分钟;[475M+H]+ |
I-28 | H | C6H5 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.75分钟;[489M+H]+ |
I-29 | H | CH3 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 2.95分钟;[399M+H]+ |
I-30 | H | CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.18分钟;[413M+H]+ |
I-31 | H | CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.38分钟;[427M+H]+ |
I-32 | H | CH3 | H | C6H5 | H | O | H | Cl | 2,4,6-F3 | 3.29分钟;[433M+H]+ |
I-33 | H | CH2CH2CH3 | H | H | H | O | H | Cl | 2,4,6-F3 | 164-167℃ |
I-34 | H | CH2CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.34分钟;[427 M+H]+ |
I-35 | H | CH2CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.54分钟;[441 M+H]+ |
I-36 | H | CH2CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.72分钟;[455 M+H]+ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃];1H-NMR[δppm] |
I-37 | H | CH2CH2CH3 | H | H | H | O | H | Cl | 2-Cl,6-OCH3 | 72-74℃ |
I-38 | H | CH(CH3)2 | H | H | H | O | H | Cl | 2-Cl,6-OCH3 | 78-81℃ |
I-39 | H | CH3 | H | CH3 | H | O | H | Cl | 2-Cl,6-OCH3 | 70-73℃ |
I-40 | H | CH3 | H | CH3 | CH3 | O | H | Cl | 2-Cl,6-OCH3 | 3.03分钟;[395M+H]+ |
I-41 | H | CH3 | H | H | H | O | H | Cl | 2-Cl,6-OCH3 | 2.67分钟;[367M+H]+ |
I-42 | H | CH2CH3 | H | H | H | O | H | Cl | 2-Cl,6-OCH3 | 2.83分钟;[381M+H]+ |
I-43 | H | CH2CH2CH3 | H | H | H | O | H | Cl | 2-Cl,6-F | 2.99分钟;[383M+H]+ |
I-44 | H | CH(CH3)2 | H | H | H | O | H | Cl | 2-Cl,6-F | 3.00分钟;[383M+H]+ |
I-45 | H | CH3 | H | CH3 | H | O | H | Cl | 2-Cl,6-F | 2.78分钟;[369M+H]+ |
I-46 | H | CH3 | H | CH3 | CH3 | O | H | Cl | 2-Cl,6-F | 67-69℃ |
I-47 | H | CH3 | H | H | H | O | H | Cl | 2-Cl,6-F | 76-79℃ |
I-48 | H | CH2CH3 | H | H | H | O | H | Cl | 2-Cl,6-F | 80-82℃ |
I-49 | H | CH3 | H | H | H | S | CH2CH2CH3 | Cl | 2,4,6-F3 | 3.72分钟;[416M+H]+ |
I-50 | H | CH2CH3 | H | H | H | S | CH2CH3 | Cl | 2,4,6-F3 | 3.67分钟;[416M+H]+ |
I-51 | H | CH3 | H | CH3 | CH3 | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.45分钟;[427M+H]+ |
I-52 | H | CH3 | H | CH3 | CH3 | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.70分钟;[441M+H]+ |
I-53 | H | CH3 | H | CH3 | CH3 | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.92分钟;[455M+H]+ |
I-54 | H | CH3 | H | H | H | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.35分钟;[447M+H]+ |
I-55 | H | CH(CH3)2 | H | H | H | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.65分钟;[475M+H]+ |
I-56 | H | CH(CH3)2 | H | H | H | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.48分钟;[463M+H]+ |
I-57 | H | CH(CH3)2 | H | H | H | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 3.88分钟;[469M+H]+ |
I-58 | H | CH(CH3)2 | H | H | H | O | C(O)C(=CH2)CH3 | Cl | 2,4,6-F3 | 3.67分钟;[453M+H]+ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃];1H-NMR[δppm] |
I-59 | H | CH3 | H | H | H | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 3.59分钟;[441M+H]+ |
I-60 | H | CH3 | H | H | H | O | C(O)C(=CH2)CH3 | Cl | 2,4,6-F3 | 3.35分钟;[425M+H]+ |
I-61 | H | CH3 | H | CH3 | CH3 | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.74分钟;[475M+H]+ |
I-62 | H | CH3 | H | CH3 | CH3 | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.48分钟;[463M+H]+ |
I-63 | H | CH3 | H | CH3 | CH3 | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 4.06分钟;[469M+H]+ |
I-64 | H | CH3 | H | CH3 | CH3 | O | C(O)C(=CH2)CH3 | Cl | 2,4,6-F3 | 3.85分钟;[453M+H]+ |
I-65 | H | C(CH3)3 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.51分钟;[441M+H]+ |
I-66 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.72分钟;[455M+H]+ |
I-67 | H | C(CH3)3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.90分钟;[469M+H]+ |
I-68 | H | C(CH3)3 | H | H | H | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.83分钟;[490M+H]+ |
I-69 | H | C(CH3)3 | H | H | H | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.66分钟;[477M+H]+ |
I-70 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 4.06分钟;[483M+H]+ |
I-71 | H | CH(CH3)2 | H | H | H | O | H | Cl | 2,4,6-F3 | 2.99分钟;[385M+H]+ |
I-72 | H | CH3 | CH3 | H | H | S | CH2CH3 | Cl | 2,4,6-F3 | 3.77分钟;[415M+H]+ |
I-73 | H | CH3 | CH3 | H | H | S | CH3 | Cl | 2,4,6-F3 | 3.57分钟;[401M+H]+ |
I-74 | H | CH2CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.39分钟;[437M+H]+ |
I-75 | H | CH2CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.60分钟;[452M+H]+ |
I-76 | H | CH2CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.80分钟;[466M+H]+ |
I-77 | H | CH(CH3)2 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.36分钟;[438M+H]+ |
I-78 | H | CH(CH3)2 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.57分钟;[452M+H]+ |
I-79 | H | CH(CH3)2 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.77分钟;[466M+H]+ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z);熔点[℃];1H-NMR[δppm] |
I-80 | H | CH3 | H | CH3 | H | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.24分钟;[424M+H]+ |
I-81 | H | CH3 | H | CH3 | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.46分钟;[438M+H]+ |
I-82 | H | CH3 | H | CH3 | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.65分钟;[452M+H]+ |
I-83 | H | CH3 | H | CH3 | CH3 | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.48分钟;[438M+H]+ |
I-84 | H | CH3 | H | CH3 | CH3 | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.71分钟;[452M+H]+ |
I-85 | H | CH3 | H | CH3 | CH3 | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.91分钟;[466M+H]+ |
I-86 | H | CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.02分钟;[410M+H]+ |
I-87 | H | CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.24分钟;[424M+H]+ |
I-88 | H | CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.45分钟;[438M+H]+ |
I-89 | H | CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,4-OCH3 | 3.19分钟;[424M+H]+ |
I-90 | H | CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.42分钟;[438M+H]+ |
I-91 | H | CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.62分钟;[452M+H]+ |
I-92 | H | CH2CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 3.35分钟;[426M+H]+ |
I-93 | H | CH2CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.56分钟;[440M+H]+ |
I-94 | H | CH2CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.76分钟;[454M+H]+ |
I-95 | H | CH(CH3)2 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 3.33分钟;[426M+H]+ |
I-96 | H | CH(CH3)2 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.53分钟;[440M+H]+ |
I-97 | H | CH(CH3)2 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.73分钟;[454M+H]+ |
I-98 | H | CH3 | H | CH3 | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 3.17分钟;[412M+H]+ |
I-99 | H | CH3 | H | CH3 | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.41分钟;[426M+H]+ |
I-100 | H | CH3 | H | CH3 | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.61分钟;[440M+H]+ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃];1H-NMR[δppm] |
I-101 | H | CH3 | CH3 | CH3 | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 3.43分钟;[426M+H]+ |
I-102 | H | CH3 | CH3 | CH3 | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.67分钟;[440M+H]+ |
I-103 | H | CH3 | CH3 | CH3 | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.91分钟;[454M+H]+ |
I-104 | H | CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 2.95分钟;[398M+H]+ |
I-105 | H | CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.18分钟;[412M+H]+ |
I-106 | H | CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.40分钟;[426M+H]+ |
I-107 | H | CH2CH3 | H | H | H | O | C(O)CH3 | Cl | 2-Cl,6-F | 3.14分钟;[412M+H]+ |
I-108 | H | CH2CH3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.36分钟;[426M+H]+ |
I-109 | H | CH2CH3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.57分钟;[440M+H]+ |
I-110 | H | CH2CH3 | H | H | H | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.68分钟;[421M+H]+ |
I-111 | H | C(CH3)3 | H | H | H | O | H | Cl | 2-Cl,4-OCH3 | 3.66分钟;[409M+H]+ |
I-112 | H | C(CH3)3 | H | H | H | O | H | Cl | 2-Cl,6-F | 3.29分钟;[397M+H]+ |
I-113 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,4-OCH3 | 3.76分钟;[465M+H]+ |
I-114 | H | C(CH3)3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,4-OCH3 | 3.93分钟;[479M+H]+ |
I-115 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH3 | Cl | 2-Cl,6-F | 3.71分钟;[453M+H]+ |
I-116 | H | C(CH3)3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2-Cl,6-F | 3.89分钟;[467M+H]+ |
I-117 | H | CH3 | H | H | H | O | CH2CH3 | Cl | 2,4,6-F3 | 3.37分钟;[386M+H]+ |
I-118 | H | CH3 | H | H | H | O | C(O)C(CH3)=CH2 | Cl | 2,4,6-F3 | 3.36分钟;[425M+H]+ |
I-119 | H | CH3 | H | CH3 | CH3 | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.74分钟;[476M+H]+ |
I-120 | H | CH3 | H | CH3 | CH3 | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.49分钟;[463M+H]+ |
I-121 | H | CH3 | H | CH3 | CH3 | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 4.07分钟;[469M+H]+ |
序号 | R1 | R2 | R3 | R4 | R5 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃];1H-NMR[δppm] |
I-122 | H | CH3 | H | CH3 | CH3 | O | C(O)C(CH3)=CH2 | Cl | 2,4,6-F3 | 3.85分钟;[453M+H]+ |
I-123 | H | C(CH3)3 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.52分钟;[441M+H]+ |
I-124 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.73分钟;[455M+H]+ |
I-125 | H | C(CH3)3 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.91分钟;[469M+H]+ |
I-126 | H | C(CH3)3 | H | H | H | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.84分钟;[490M+H]+ |
I-127 | H | C(CH3)3 | H | H | H | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.67分钟;[477M+]+ |
I-128 | H | C(CH3)3 | H | H | H | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 4.06分钟;[483M+H]+ |
I-129 | H | C(CH3)3 | H | H | H | O | C(O)C(CH3)=CH2 | Cl | 2,4,6-F3 | 3.87分钟;[467M+H]+ |
I-130 | CH3 | CH3 | H | H | 3-甲基异唑烷-5-基 | Cl | 2,4,6-F3 | 3.36分钟;[426M+H]+ | ||
I-131 | H | CH3 | H | H | H | O | C2H5 | Cl | 2,4,6-F3 | 3.36分钟;[385M+H]+ |
I-132 | H | CH(CH3)C2H5 | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.50分钟;[441M+H]+ |
I-133 | H | CH(CH3)C2H5 | H | H | H | O | C(O)C2H5 | Cl | 2,4,6-F3 | 3.70分钟;[455M+H]+ |
I-134 | H | CH(CH3)C2H5 | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.88分钟;[469M+H]+ |
I-135 | H | CH(CH3)C2H5 | H | H | H | O | C(O)CHClCH3 | Cl | 2,4,6-F3 | 3.81分钟;[489M+H]+ |
I-136 | H | CH(CH3)C2H5 | H | H | H | O | C(O)CHF2 | Cl | 2,4,6-F3 | 3.64分钟;[477M+H]+ |
I-137 | H | CH(CH3)C2H5 | H | H | H | O | C(O)CH2CH(CH3)2 | Cl | 2,4,6-F3 | 4.04分钟;[483M+H]+ |
I-138 | H | CH(CH3)C2H5 | H | H | H | O | H | Cl | 2,4,6-F3 | 3.18分钟;[399M+H]+ |
I-139 | H | C(CH3)3 | H | H | H | O | H | OCH3 | 2,4,6-F3 | 3.08分钟;[395M+H]+ |
I-140 | H | CH(CH3)C2H5 | H | H | H | O | H | OCH3 | 2,4,6-F3 | 3.07分钟;[395M+H]+ |
I-141 | H | CH(CH3)C2H5 | H | H | H | O | H | Cl | 2-Cl,6-F | 3.22分钟;[398M+H]+ |
I-142 | H | CH(CH3)C2H5 | H | H | H | O | H | Cl | 2-Cl,4-OCH3 | 3.25分钟;[410M+H]+ |
#表示与Y的键
式I.2化合物
表II
序号 | R1 | R2 | R3 | R4 | R5 | R6 | R7 | Y | Z | X | Lm | 物理数据HPLC(RT[分钟];MS[m/z]);熔点[℃] |
II-1 | H | CH3 | H | H | H | H | H | O | H | Cl | 2,4,6-F3 | 2.59分钟;[371M+H]+ |
II-2 | H | CH3 | H | H | H | H | H | O | C(O)CH3 | Cl | 2,4,6-F3 | 3.04分钟;[413M+H]+ |
II-3 | H | CH3 | H | H | H | H | H | O | C(O)CH2CH3 | Cl | 2,4,6-F3 | 3.07分钟;[427M+H]+ |
II-4 | H | CH3 | H | H | H | H | H | O | C(O)CH(CH3)2 | Cl | 2,4,6-F3 | 3.45分钟;[441M+H]+ |
对有害真菌的作用实施例
通过下列实验证实式I化合物的杀真菌作用:
将活性化合物单独配制成在丙酮或DMSO中含有0.25重量%活性化合物的储备溶液。向该溶液中加入1重量%乳化剂Wettol EM 31(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)。将活性化合物的储备溶液用水稀释至所述浓度。
应用实施例1-对由早疫链格孢(Alternaria solani)引起的西红柿早疫病的活性
将栽培品种为“Golden Queen”的盆栽植物的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将叶子用早疫链格孢在2%生物麦芽溶液中的含水孢子悬浮液(密度为0.17×106个孢子/mL)侵染。然后将植物置于20-22C的水蒸气饱和室中。5天后未处理但侵染的对照植物上的病害发展到可以肉眼测定侵染百分数的程度。
在该试验中,在每种情况下用250ppm活性化合物I-1至I-7、I-9、I-14、I-16、I-20、I-21、I-22、I-25、I-29、I-33至I-40、I-43至I-46,I-55、I-56、I-57、I-65、I-66、I-73至I-80、I-83、I-84和I-95至I-97处理的植物显示出不超过15%的侵染水平,而未处理植物90%被侵染。
应用实施例2-对由大麦网斑病菌(Pyrenophora teres)引起的大麦网斑病的活性,1天保护性施用
将栽培品种为“Hanna”的盆栽大麦秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。喷雾涂层干燥24小时后,将试验植物用大麦网斑病菌(Pyrenophora[同义词Drechslera]teres)-网斑病病原体的含水孢子悬浮液接种。然后将试验植物放入温度为20-24℃且相对大气湿度为95-100%的温室中。6天后以整个叶面积的侵染%肉眼测定病害的发展程度。
在该试验中,在每种情况下用250ppm活性化合物I-1、I-2、I-6至I-11、I-14至I-24、I-33至I-40、I-44、I-45、I-55至I-58、I-71、I-74、I-76和I-77处理的植物显示出不超过10%的侵染水平,而未处理植物90%被侵染。
Claims (13)
1.式I的三唑并嘧啶:
其中各取代基如下所定义:
R1为氢、C1-C12烷基、C1-C12卤代烷基、C3-C6环烷基、C3-C8卤代环烷基、C2-C12链烯基、C2-C12卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C12炔基、C2-C12卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R2为C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C2-C8链烯基、C2-C8卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C8炔基、C2-C8卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R3、R4、R5、R6、R7为氢或在R2下提到的基团之一;
R4与R3或R6一起还可以形成5或6员饱和或不饱和环,该环除了碳原子外还可以另外包含1-3个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
R2与R3、R4与R5、R6与R7在每种情况下还可以一起为氧而形成羰基以及一起形成可以被1-3个选自O、N和S的杂原子间隔的C2-C5亚烷基或亚链烯基或亚炔基链而形成螺基;
R1-R7在每种情况下可以带有1-4个相同或不同的基团Ra:
Ra为卤素、氰基、硝基、羟基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基羰基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷氧羰基、C1-C6烷硫基、C1-C6烷基氨基、二C1-C6烷基氨基、C2-C8链烯基、C2-C8卤代链烯基、C3-C8环烯基、C2-C6链烯氧基、C3-C6卤代链烯氧基、C2-C6炔基、C2-C6卤代炔基、C3-C6炔氧基、C3-C6卤代炔氧基、C3-C6环烷氧基、C3-C6环烯氧基、氧基-C1-C3亚烷氧基、苯基、萘基、包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环,
其中这些脂族、脂环族或芳族基团本身可以部分或完全被卤代或可以带有1-3个基团Rb:
Rb为卤素、氰基、硝基、羟基、巯基、氨基、羧基、氨基羰基、氨基硫羰基、烷基、卤代烷基、链烯基、链烯氧基、炔氧基、烷氧基、卤代烷氧基、烷硫基、烷基氨基、二烷基氨基、甲酰基、烷基羰基、烷基磺酰基、烷基次磺酰基、烷氧羰基、烷基羰氧基、烷基氨基羰基、二烷基氨基羰基、烷基氨基硫羰基、二烷基氨基硫羰基,其中这些基团中的烷基包含1-6个碳原子且这些基团中的上述链烯基或炔基包含2-8个碳原子;
和/或带有1-3个下列基团:
环烷基、环烷氧基、杂环基、杂环氧基,其中环状体系包含3-10个环成员;芳基、芳氧基、芳硫基、芳基-C1-C6烷氧基、芳基-C1-C6烷基、杂芳基、杂芳氧基、杂芳硫基,其中芳基优选包含6-10个环成员且杂芳基包含5或6个环成员,其中环状体系可以部分或完全被卤代或可以被烷基或卤代烷基取代;
p为0或1;
L为卤素、C1-C4烷基、C1-C2卤代烷基、C1-C4烷氧基、氰基、硝基、氨基、C1-C4烷基氨基、二(C1-C4)烷基氨基、C1-C4烷基羰基氨基、C(O)-R、S(O)n-R;
R为氢、C1-C4烷基、C1-C2卤代烷基、C1-C4烷氧基、C2-C4链烯氧基、C2-C4炔氧基、氨基、C1-C4烷基氨基、二(C1-C4)烷基氨基;其中基团R可以被1-3个基团Rb取代;
n为0、1或2;
m为1、2、3、4或5;
X为卤素、氰基、C1-C4烷基、C1-C4烷氧基、C2-C4链烯氧基、C2-C4炔氧基或C1-C2卤代烷氧基,
Y为氧或硫;
Z为氢、C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C8烷基羰基、C1-C8烷氧羰基、(C=O)NRARB、C3-C8链烯氧羰基、C3-C8炔氧羰基、C3-C6环烷基羰基、C2-C8链烯基、C2-C8卤代链烯基、C3-C8环烯基、C2-C6炔基、C2-C6卤代炔基、C3-C6环烷氧羰基、C3-C6环烯氧羰基、C1-C8烷基亚磺酰基、C1-C8烷硫基、C1-C8烷基磺酰基、苯基、萘基、包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环;
或
Z与R5或R7一起还可以形成5或6员饱和或不饱和环,该环除了碳原子和Y以外还可以另外包含1或2个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
基团Z可以部分或完全被卤代或带有1-3个基团Rb;
RA、RB独立地为氢、C1-C8烷基、C2-C8链烯基、C2-C8炔基、C3-C6环烷基或C3-C6环烯基;
RA和RB可以与它们所连接的氮原子一起形成5或6员饱和、部分不饱和或芳族环,该环除了碳原子外可以另外包含1-3个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra。
2.根据权利要求1的式I化合物,其中各取代基如下所定义:
R1为氢、C1-C12烷基、C1-C12卤代烷基、C3-C6环烷基、C3-C8卤代环烷基、C2-C12链烯基、C2-C12卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C12炔基、C2-C12卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R2为C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6卤代环烷基、C2-C8链烯基、C2-C8卤代链烯基、C3-C6环烯基、C3-C6卤代环烯基、C2-C8炔基、C2-C8卤代炔基或苯基、萘基,或包含1-4个选自O、N和S的杂原子的5或6员饱和、部分不饱和或芳族杂环,
R3、R4、R5、R6、R7为氢或在R2下提到的基团之一;
R4与R3或R6一起还可以形成5或6员饱和或不饱和环,该环除了碳原子外还可以另外包含1-3个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
R2与R3、R4与R5、R6与R7在每种情况下可以一起形成可以被1-3个选自O、N和S的杂原子间隔的C2-C5亚烷基或亚链烯基或亚炔基链而形成螺基;
R1-R7在每种情况下可以带有1-4个相同或不同的根据权利要求1的基团Ra;
Z为氢、C1-C8烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C8烷基羰基、C3-C6环烷基羰基、C2-C8链烯基、C2-C8卤代链烯基、C3-C8环烯基、C2-C6炔基、C2-C6卤代炔基、苯基、萘基,包含1-4个选自O、N和S的杂原子的5-10员饱和、部分不饱和或芳族杂环;或
Z与R4或R6一起还可以形成5或6员饱和或不饱和环,该环除了碳原子和Y以外还可以另外包含1或2个选自O、N和S的杂原子作为环成员和/或可以带有一个或多个取代基Ra;
基团Z可以部分或完全被卤代或带有1-3个根据权利要求1的基团Rb。
3.根据权利要求1或2的式I化合物,其中X为氯或甲基,尤其是氯。
4.根据权利要求1-3中任一项的式I化合物,其中指数p为0。
5.根据权利要求1-4中任一项的式I化合物,其中至少一个基团L位于与三唑并嘧啶骨架的连接点的邻位。
7.根据权利要求1-6中任一项的式I化合物,其中被Lm取代的苯基为下述取代基的组合之一:2-氟-6-氯、2,6-二氟、2,6-二氯、2-氟-6-甲基、2,4,6-三氟、2,6-二氟-4-甲氧基、2-氯-4-甲氧基、五氟、2-甲基-4-氟、2-三氟甲基、2-甲氧基-6-氟、2-氯、2-氟、2,4-二氟、2-氟-4-氯、2-氯-4-氟、2-氯-5-氟、2,3-二氟、2,5-二氟、2,3,4-三氟、2-甲基、2,4-二甲基、2-甲基-4-氯、2-甲基-5-氟、2-氟-4-甲基、2,6-二甲基、2,4,6-三甲基、2,6-二氟-4-甲基、2-三氟甲基-4-氟、2-三氟甲基-5-氟或2-三氟甲基-5-氯。
9.根据权利要求8的方法,其中Z为氢。
10.一种适于防治有害真菌的组合物,该组合物包含固体或液体载体和根据权利要求1或2的式I化合物。
11.根据权利要求10的组合物,其除了式I化合物外额外包含其他活性化合物。
12.一种防治植物病原性有害真菌的方法,该方法包括用有效量的根据权利要求1的式I化合物处理真菌或需要防止真菌侵袭的材料、植物、土壤或种子。
13.种子,以1-1000g/100kg的量包含式I化合物。
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