CN1852895A - 作为杀真菌型植物保护剂的4-吡啶甲基磺酰胺衍生物 - Google Patents
作为杀真菌型植物保护剂的4-吡啶甲基磺酰胺衍生物 Download PDFInfo
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- CN1852895A CN1852895A CNA2004800270626A CN200480027062A CN1852895A CN 1852895 A CN1852895 A CN 1852895A CN A2004800270626 A CNA2004800270626 A CN A2004800270626A CN 200480027062 A CN200480027062 A CN 200480027062A CN 1852895 A CN1852895 A CN 1852895A
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- methyl
- alkyl
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- 230000000855 fungicidal effect Effects 0.000 title description 5
- WXQDLXGLMTUUKH-UHFFFAOYSA-N pyridin-4-ylmethanesulfonamide Chemical class NS(=O)(=O)CC1=CC=NC=C1 WXQDLXGLMTUUKH-UHFFFAOYSA-N 0.000 title description 3
- 239000011814 protection agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- -1 aminocarboxyl Chemical group 0.000 claims description 113
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229940084434 fungoid Drugs 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
- 150000003456 sulfonamides Chemical class 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 125000004970 halomethyl group Chemical group 0.000 abstract 2
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 230000002538 fungal effect Effects 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000001717 pathogenic effect Effects 0.000 abstract 1
- 239000002585 base Substances 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 229940031815 mycocide Drugs 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000080 wetting agent Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 150000003851 azoles Chemical class 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 240000006365 Vitis vinifera Species 0.000 description 6
- 235000014787 Vitis vinifera Nutrition 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000000160 oxazolidinyl group Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000006072 paste Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 241000213004 Alternaria solani Species 0.000 description 4
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 4
- 239000005644 Dazomet Substances 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 150000003818 basic metals Chemical class 0.000 description 4
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000004533 oil dispersion Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
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- 150000002632 lipids Chemical class 0.000 description 3
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- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- 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
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 235000012239 silicon dioxide Nutrition 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
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000004550 soluble concentrate Substances 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 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
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 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
- 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
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 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
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Abstract
本发明涉及式(I)的磺酰胺,其中取代基具有下列含义:R1是H、烷基、烷氧基、链烯基或链炔基,且R2、R3、R4、R5是氢、卤素、烷基、烷氧基或卤代甲基;R2和R3还可以一起形成苯基、环戊基或环己基环,其中所述环可以带有R2’和R3’,其中R2’、R3’是H、卤素、烷基、烷氧基或卤代甲基;在情况a)下,当R2、R3、R4和R5是氢时,则X是由-C(R6)=NOR7基团取代的苯基,其中R6是烷基且R7是烷基、苄基、链烯基、卤代烷基、卤代链烯基、链炔基或卤代链炔基;以及在情况b)下,当基团R2、R3、R4和R5中的至少一个不是氢时,则X是苯基,萘基或由碳原子连接且含有1-4个选自O、N和S的杂原子的5元或6元的饱和、部分不饱和或芳族杂环,其中X可以如说明书中所述被取代。本发明进一步涉及制备所述化合物的方法,涉及含有该化合物的试剂,以及涉及其在防治植物病原性有害真菌中的用途。
Description
本发明涉及式(I)的磺酰胺:
其中取代基如下:
R1是H、C1-C4烷基、C1-C4烷氧基、C2-C4链烯基、C2-C4链炔基或苄基;
R2、R3、R4、R5相互独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1卤代甲基;
R2和R3还可以一起形成苯基、环戊基或环己基环,这些环可以带有两个基团R2’和R3’;
R2’、R3’相互独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1卤代甲基;
在情况a)下,如果R2、R3、R4和R5是氢,则:
X是由-C(R6)=NOR7基团取代的苯基,其中
R6是C1-C4烷基和
R7是C1-C8烷基、苄基、C2-C4链烯基、C1-C4卤代烷基、C2-C4
卤代链烯基、C2-C4链炔基或C2-C4卤代链炔基;以及在情况b)下,如果基团R2、R3、R4和R5中的至少一个不是氢,则:X是苯基,萘基或由碳原子连接且含有1-4个选自O、N和S的杂原子的5元或6元的饱和、部分不饱和或芳族杂环,其中X可以带有1-4个Ra基团:
Ra是卤素、氰基、硝基、C1-C8烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基、-C(R6)=NOR7、C1-C4烷基氨基羰基、二(C1-C4烷基)氨基羰基或者苯基或苯氧基,其中环可以带有1-3个Rb基团:
Rb是卤素、C1-C4烷基、C1-C4烷氧基、C1卤代烷基或C1卤代烷氧基;
Ra或Rb还可以是C3-C4亚烷基或C4亚烯基,其和与它连接的苯基环的两个相邻成环原子一起形成可以由一个或多个上述Ra或Rb基团取代的环。
此外,本发明涉及制备这些化合物的方法,涉及含有这些化合物的组合物,以及涉及其在防治植物病原性有害真菌中的用途。
DE-A 31 22 700和WO 00/06083以总体方式公开了作为药物的吡啶磺酰胺。这些文献的总体公开包括4-吡啶甲基磺酰胺。
由EP-A 206 581和Lieb.Ann.Chem.641(1990)已知单个4-吡啶甲基磺酰胺。在所述出版物中描述的化合物适用于防治有害真菌。
然而,在许多情况下它们的作用不令人满意。基于这一点,本发明的目的是提供具有改进的作用和/或更宽的活性范围的化合物。
因此,我们发现该目的通过开头定义的化合物实现。此外,我们还发现了制备该化合物的方法和中间体、含有该化合物的组合物以及使用化合物I防治有害真菌的方法。
本发明化合物与EP-A 206 581、DE-A 31 22 700和WO 00/06083所述化合物的不同在于4-吡啶甲基,并且与由Lieb.Ann.Chem.641(1990)已知的化合物的不同在于吡啶环上的取代或X基团。
与已知化合物相比,式I的化合物对有害真菌具有增加的活性。
本发明化合物可以通过不同的途径得到。它们有利地通过在碱性条件下使式II吡啶衍生物与其中的X如权利要求1所定义的式III磺酸或活化磺酸衍生物反应而得到。在式III中,L是羟基或卤素,优选氯。
该反应通常在碱存在下在惰性有机溶剂中在-30℃至120℃,优选-10℃至100℃的温度下进行(参考Lieb.Ann.Chem.641(1990))。
合适的溶剂是脂族烃如戊烷、己烷、环己烷和石油醚,芳族烃如甲苯、邻-、间-和对-二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚如乙醚、二异丙醚、甲基叔丁基醚、二烷、苯甲醚和四氢呋喃,腈如乙腈和丙腈,酮如丙酮、丁酮、二乙基甲酮和甲基叔丁基甲酮,还有二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,特别优选二异丙醚、乙醚和四氢呋喃。还可以使用所述溶剂的混合物。
合适的碱通常是无机化合物如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐如碳酸氢钠,还可以是有机碱,例如叔胺如三甲胺、三乙胺、三异丙基乙胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、二甲基吡啶和4-二甲基氨基吡啶以及双环胺。特别优选吡啶、三乙胺和碳酸钾。通常以催化用量使用碱;然而,它们还可以以等摩尔量、过量使用或在合适的情况下作为溶剂使用。
原料通常以等摩尔量互相反应。对于产率而言,基于III采用过量的II是有利的。
制备化合物I所需要的原料是可购买的或者由文献[J.für praktischeChemie,第695页(1994);Heterocycles,第675页(1995);Tetrahedron,第12483页(1996);Chem.Pharm.Bull.,第1927页(1973);J.Chem.Soc.,第426页(1942);EP-A 983 982;Synthesis,第852页(1986)]已知或者可以根据所述文献制备。
以常用方式后处理反应混合物,例如通过与水混合,分离各相,以及如果合适的话色谱提纯粗产物。以无色或浅褐色的粘稠油状物形式得到一些中间体和终产物,这些中间体和终产物在减压和温和升高的温度下提纯或除去挥发性组分。如果以固体得到中间体和终产物,则还可以通过重结晶或浸提进行提纯。
如果单个化合物I不能通过上述途径得到,它们则可以通过其它化合物I的衍生而制备。
然而,如果合成产生了异构体的混合物,通常不必要求分离,因为在某些情况下单个异构体可以在为了使用而进行的后处理过程中或者在应用过程中(例如在光、酸或碱的作用下)相互转化。该转化还可以在使用后发生,例如在处理过的植物中的植物处理中,或者在待防治的有害真菌中。
在上式给出的符号定义中使用了通常表示下列取代基的概括性术语。卤素:氟、氯、溴和碘。
烷基:具有1-4、6或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或4个碳原子的直链或支化烷基(如上所述),在这些基团中,部分或全部氢原子可以由上述卤素原子取代;特别是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、二氯氟甲基、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-2-丙基。
链烯基:具有2-4、6或8个碳原子且在任何位置上具有1或2个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2-6个碳原子且在任何位置上具有1或2个双键的不饱和直链或支化烃基(如上所述),在这些基团中,部分或全部氢原子可以由上述卤素原子取代,特别是由氟、氯和溴取代;
链炔基:具有2-4、6或8个碳原子且在任何位置上具有1或2个叁键的直链或支化烃基,例如C2-C6链炔基如乙炔基、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8个成环碳原子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;
含有1-4个选自O、N和S的杂原子的5-10元饱和、部分不饱和或芳族杂环:
-含有1-3个氮原子和/或一个氧或硫原子或者1或2个氧和/或硫原子的5元或6元杂环基,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、3-吡咯啉-2-基、2-吡咯啉-3-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个氮原子和一个硫或氧原子的5元杂芳基:除了碳原子以外,还可以含有作为成环原子的1-4个氮原子或1-3个氮原子和一个硫或氧原子的5元杂芳基,例如2-噻吩基、3-噻吩基、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或1-4个氮原子的6元杂芳基:除了碳原子以外,还可以含有作为成环原子的1-3或1-4个氮原子的6元杂芳基,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:3-5个CH2基团的二价未支化链,例如CH2、CH2CH2、CH2CH2CH2、CH2CH2CH2CH2和CH2CH2CH2CH2CH2;
氧基亚烷基:2-4个CH2基团的二价未支化链,其中一个价键由氧原子连接到骨架上,例如OCH2CH2、OCH2CH2CH2和OCH2CH2CH2CH2;
氧基亚烷氧基:1-3个CH2基团的二价未支化链,其中两个价键均由氧原子连接到骨架上,例如OCH2O、OCH2CH2O和OCH2CH2CH2O;
亚烯基:由共轭C=C双键连接的4-6个CH基团的二价未支化链,例如CH=CH或CH=CH-CH=CH。
本发明的范围包括具有手性中心的式I化合物的(R)-和(S)-异构体以及外消旋物。
根据式I磺酰胺意欲的用途,特别优选取代基的下列含义,在每种情况下单独或结合:
本发明优选提供其中R1是氢、甲基、甲氧基、乙氧基、烯丙基或炔丙基,尤其是氢或甲基的式I化合物。
同样优选其中R2、R3、R4和R5相互独立地是氢、甲基、乙基、氟、氯、CF3、OCF3或OCHF2的式I化合物。
此外,仍然优选其中R2、R3、R4和R5中的至少一个,尤其是一个或两个基团不是氢的式I化合物。
同样优选由R2、R3、R4和R5中的两个相同基团取代的式I化合物。
式I化合物的其它优选实施方案在每种情况下是式I.1至I.6的化合物本身,其中的变量如式I所定义:
优选其中R2’和R3’基团位于6,7-位上的式I.4化合物。
特别优选其中X是在对位上带有Ra基团的苯基环的式I化合物;这些化合物对应于式IA:
特别优选其中Ra具有下列含义的式I化合物:C(R6)=NOR7、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、二氯氟甲基、氯二氟甲基、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、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯二氟甲氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2,2,2-三氯乙氧基和五氟乙氧基。
R6的特别优选的实施方案是甲基;R7优选是甲基、乙基、烯丙基或炔丙基,R7基团还可以被卤代。
尤其根据它们的用途,优选汇集在下表中的化合物I。此外,表中取代基的所述基团本身(独立于其中提到它们的结合)是该取代基的特别优选的实施方案。
表1
式IA的化合物,其中R2、R3、R4和R5是氢并且对于每种化合物R1和Ra的结合对应于表A的一行A-1至A-14。
表2
式IA.1的化合物,其中R2和R3是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表3
式IA.1的化合物,其中R2和R3是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表4
式IA.1的化合物,其中R2和R3是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表5
式IA.1的化合物,其中R2和R3是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表6
式IA.1的化合物,其中R2和R3是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表7
式IA.2的化合物,其中R3和R5是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表8
式IA.2的化合物,其中R3和R5是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表9
式IA.2的化合物,其中R3和R5是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表10
式IA.2的化合物,其中R3和R5是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表11
式IA.2的化合物,其中R3和R5是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表12
式IA.3的化合物,其中R2和R4是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表13
式IA.3的化合物,其中R2和R4是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表14
式IA.3的化合物,其中R2和R4是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表15
式IA.3的化合物,其中R2和R4是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表16
式IA.3的化合物,其中R2和R4是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表17
式IA.4’的化合物,其中R2和R3是氢并且对于每种化合物R1和Ra的结合对应于表A的一行。
表18
式IA.4’的化合物,其中R2和R3是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表19
式IA.4’的化合物,其中R2和R3是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表20
式IA.4’的化合物,其中R2和R3是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表21
式IA.4’的化合物,其中R2和R3是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表22
式IA.4’的化合物,其中R2和R3是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表23
式IA.5的化合物,其中R2是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表24
式IA.5的化合物,其中R2是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表25
式IA.5的化合物,其中R2是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表26
式IA.5的化合物,其中R2是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表27
式IA.5的化合物,其中R2是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表28
式IA.6的化合物,其中R3是甲基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表29
式IA.6的化合物,其中R3是氟并且对于每种化合物R1和Ra的结合对应于表A的一行。
表30
式IA.6的化合物,其中R3是氯并且对于每种化合物R1和Ra的结合对应于表A的一行。
表31
式IA.6的化合物,其中R3是甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表32
式IA.6的化合物,其中R3是三氟甲氧基并且对于每种化合物R1和Ra的结合对应于表A的一行。
表A
编号 | R1 | Ra |
A-1 | H | C(CH3)=NOCH3 |
A-2 | CH3 | C(CH3)=NOCH3 |
A-3 | H | C(CH3)=NOCH2CH3 |
A-4 | CH3 | C(CH3)=NOCH2CH3 |
A-5 | H | C(CH3)=NOCH2CH=CH2 |
A-6 | CH3 | C(CH3)=NOCH2CH=CH2 |
A-7 | H | C(CH3)=NOCH2C≡CH |
A-8 | CH3 | C(CH3)=NOCH2C≡CH |
A-9 | H | C(CH3)=NOCH2CCl=CH2 |
A-10 | CH3 | C(CH3)=NOCH2CCl=CH2 |
A-11 | H | H |
A-12 | CH3 | H |
A-13 | H | CH3 |
A-14 | CH3 | CH3 |
A-15 | H | CH2CH3 |
A-16 | CH3 | CH2CH3 |
A-17 | H | CH2CH2CH3 |
A-18 | CH3 | CH2CH2CH3 |
A-19 | H | CH(CH3)2 |
A-20 | CH3 | CH(CH3)2 |
A-21 | H | CH2CH2CH2CH3 |
A-22 | CH3 | CH2CH2CH2CH3 |
A-23 | H | CH(CH3)CH2CH3 |
A-24 | CH3 | CH(CH3)CH2CH3 |
A-25 | H | CH2CH(CH3)2 |
A-26 | CH3 | CH2CH(CH3)2 |
A-27 | H | C(CH3)3 |
A-28 | CH3 | C(CH3)3 |
A-29 | H | OCH3 |
A-30 | CH3 | OCH3 |
A-31 | H | OCH2CH3 |
A-32 | CH3 | OCH2CH3 |
A-33 | H | OCH2CH2CH3 |
A-34 | CH3 | OCH2CH2CH3 |
A-35 | H | OCH(CH3)2 |
A-36 | CH3 | OCH(CH3)2 |
A-37 | H | OCH2CH2CH2CH3 |
A-38 | CH3 | OCH2CH2CH2CH3 |
A-39 | H | OCH(CH3)CH2CH3 |
A-40 | CH3 | OCH(CH3)CH2CH3 |
A-41 | H | OCH2CH(CH3)2 |
A-42 | CH3 | OCH2CH(CH3)2 |
A-43 | H | OC(CH3)3 |
A-44 | CH3 | OC(CH3)3 |
A-45 | H | CCl3 |
A-46 | CH3 | CCl3 |
A-47 | H | CHF2 |
A-48 | CH3 | CHF2 |
A-49 | H | CF3 |
A-50 | CH3 | CF3 |
A-51 | H | CHClF |
A-52 | CH3 | CHClF |
A-53 | H | CH2CHF2 |
A-54 | CH3 | CH2CHF2 |
A-55 | H | CH2CF3 |
A-56 | CH3 | CH2CF3 |
A-57 | H | CF2CF3 |
A-58 | CH3 | CF2CF3 |
A-59 | H | OCHCl2 |
A-60 | CH3 | OCHCl2 |
A-61 | H | OCCl3 |
A-62 | CH3 | OCCl3 |
A-63 | H | OCH2F |
A-64 | CH3 | OCH2F |
A-65 | H | OCHF2 |
A-66 | CH3 | OCHF2 |
A-67 | H | OCF3 |
A-68 | CH3 | OCF3 |
A-69 | H | OCH2CHF2 |
A-70 | CH3 | OCH2CHF2 |
A-71 | H | OCH2CF3 |
A-72 | CH3 | OCH2CF3 |
A-73 | H | OCH2CHClF |
A-74 | CH3 | OCH2CHClF |
A-75 | H | OCH2CCl3 |
A-76 | CH3 | OCH2CCl3 |
A-77 | H | OCF2CF3 |
A-78 | CH3 | OCF2CF3 |
A-79 | H | C6H5 |
A-80 | CH3 | C6H5 |
A-81 | H | OC6H5 |
A-82 | CH3 | OC6H5 |
化合物I适合作为杀真菌剂。它们的显著特征是对宽范围的植物病原性真菌具有显著的效果,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)。其中一些起内吸作用并且可以作为叶子和土壤杀真菌剂用于植物保护中。
它们对于防治各种栽培植物如小麦、黑麦、大麦、燕麦、稻、玉米、草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄、水果和观赏植物以及蔬菜如黄瓜、豆类、西红柿、土豆和葫芦,还有这些植物的种子上的许多真菌特别重要。
它们特别适合防治下列植物病害:
·在水果和蔬菜上的链格孢(Alternaria)属,
·禾谷类、稻和草坪上的平脐蠕孢(Bipolaris)属和内脐蠕孢(Drechslera)属,
·禾谷类上的禾白粉菌(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),
·葫芦上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
·各种植物上的镰刀菌(Fusarium)属和轮枝菌(Verticillium)属,
·禾谷类、香蕉和花生上的球腔菌(Mycosphaerella)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),
·苹果上的叉丝单囊壳(Podosphaera leucotricha),
·小麦和大麦上的眼斑病菌(Pseudocercosporella herpotrichoides),
·啤酒花和黄瓜上的假霜霉(Pseudoperonospora)属,
·谷类上的柄锈菌(Puccinia)属,
·稻上的稻瘟病菌(Pyricularia oryzae),
·棉花、稻和草坪上的丝核菌(Rhizoctonia)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(Uncinula necator),
·谷类和甘蔗上的黑粉菌(Ustilago)属,和
·苹果和梨上的黑星病菌(Venturia)属(斑点病)。
化合物I还适合在材料(例如木材、纸、油漆分散体、纤维或织物)保护和储藏产品保护中防治有害真菌如拟青霉(Paecilomyces variotii)。
通过用杀真菌有效量的活性化合物处理真菌或处理需要保护以免受真菌侵害的植物、种子、材料或土壤而使用化合物I。还可以在材料、植物或种子受真菌侵染之前和之后施用。
杀真菌组合物通常含有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,根据需要的效果类别,施用量为每公顷0.01-2.0kg活性化合物。
在种子处理中,每千克种子通常需要0.001-1g,优选0.01-0.05g的活性化合物用量。
当用于材料或储藏产品的保护时,活性化合物的施用量取决于施用区域的类别和所需效果。在材料保护中施用的常用量例如是每立方米处理材料为0.001g至2kg,优选0.005g至1kg的活性化合物。
化合物I可以转化为常用配制剂,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的目的;在每种情况下,应当确保本发明化合物的精细和均匀分布。
配制剂以已知方式,例如通过用溶剂和/或载体使活性化合物增量,并且如果需要的话使用乳化剂和分散剂而制备。合适的溶剂/助剂基本上是:
-水,芳族溶剂(例如Solvesso产品,二甲苯),石蜡(例如矿物油馏分),醇(例如甲醇、丁醇、戊醇、苯甲醇),酮(例如环己酮、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,脂肪酸和脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(例如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(例如高度分散的二氧化硅、硅酸盐);乳化剂如非离子和阴离子乳化剂(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。
合适的表面活性剂是木素磺酸、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,此外还有磺化萘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的溶液、乳液、糊或油分散体的是具有中至高沸点的矿物油馏分如煤油或柴油,此外还有煤焦油和源自植物或动物的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮或水。
可以通过混合或同时研磨活性物质和固体载体而制备粉末、撒播用材料和可撒粉产品。
可以通过将活性化合物粘附到固体载体上而制备颗粒如涂敷颗粒、浸渍颗粒和均相颗粒。固体载体的实例是矿土如硅胶、硅酸盐、滑石、高岭土、活性土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物来源的产物如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉以及其它固体载体。
配制剂通常含有0.01-95重量%,优选0.1-90重量%的活性化合物。活性化合物使用的纯度为90-100%,优选95-100%(根据NMR光谱)。
以下是配制剂的实例:
1.用水稀释的产品
A 水溶性浓缩物(SL)
将10重量份本发明化合物溶于水中或溶于水溶性溶剂中。或者,加入润湿剂或其它助剂。活性化合物经水稀释溶解。
B 可分散的浓缩物(DL)
将20重量份本发明化合物溶于环己酮中并加入分散剂如聚乙烯吡咯烷酮。用水稀释得到分散体。
C 可乳化的浓缩物(EC)
将15重量份本发明化合物溶于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。
D 乳液(EW、EO)
将40重量份本发明化合物溶于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%)。借助乳化机(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。
E悬浮液(SC、OD)
在搅拌的球磨机中,粉碎20重量份本发明化合物并加入分散剂、润湿剂和水或有机溶剂,得到活性化合物的微悬浮液。用水稀释得到稳定的活性化合物悬浮液。
F 水分散性颗粒和水溶性颗粒(WG、SG)
精细研磨50重量份本发明化合物并加入分散剂和润湿剂,借助技术装置(例如挤出、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。
G 水分散性粉末和水溶性粉末(WP、SP)
在转子定子磨机中,研磨75重量份本发明化合物并加入分散剂、润湿剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。
2.不经稀释而施用的产品
H 可撒粉的粉末(DP)
精细研磨5重量份本发明化合物,并与95%的细碎高岭土充分混合。由此得到可撒粉的产品。
I 颗粒(GR、FG、GG、MG)
精细研磨0.5重量份本发明化合物,并且与95.5%的载体结合。目前的方法是挤出、喷雾干燥或流化床。由此得到不经稀释而施用的颗粒。
J ULV溶液(UL)
将10重量份本发明化合物溶于有机溶剂如二甲苯中。由此得到不经稀释而施用的产品。
活性化合物可以直接、以其配制剂形式或以由其制备的使用形式,例如以可直接喷雾溶液、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;意欲在每种情况下确保本发明活性化合物尽可能最精细地分布。
含水使用形式可以通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为了制备乳液、糊或油分散体,可以借助润湿剂、增粘剂、分散剂或乳化剂将该物质直接或在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、润湿剂、增粘剂、分散剂或乳化剂以及合适的话还有溶剂或油组成的浓缩物,并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以在较宽范围内变化。通常该浓度为0.0001-10%,优选0.01-1%。
活性化合物还可以成功用于超低容量法(ULV),通过该方法可以施用含有95重量%以上的活性化合物的配制剂,或者甚至施用不含添加剂的活性化合物。
可以将各种类型的油、润湿剂、助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性化合物中,如果合适的话,直到即将施用前再将其加入(桶混)。这些试剂可以与本发明试剂以1∶10至10∶1的重量比混合。
本发明组合物作为杀真菌剂的使用形式还可以与其它活性化合物如除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将化合物I或含有它们的组合物以作为杀真菌剂的使用形式与其它杀真菌剂混合在许多情况下导致杀真菌活性范围得以扩展。
可以与本发明化合物结合使用的下列杀真菌剂用于说明可能的结合,但不对其进行限制:
·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),
·胺衍生物类,例如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),
·抗菌素类,例如放线菌酮(cycloheximide)、灰黄霉素(griseofulvin)、春雷霉素(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)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、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)、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,例如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin),
·二硫代氨基甲酸盐类,例如福美铁(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),
·杂环化合物类,例如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、赛座灭(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)、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(tricyclazole)或嗪氨灵(triforine),
·铜杀真菌剂类,例如波尔多液(Bordeaux混合物)、醋酸铜、王铜或碱式硫酸铜,
·硝基苯基衍生物类,例如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrophthalisopropyl),
·苯基吡咯类,例如拌种咯(fenpiclonil)或氟菌(fludioxonil),
·硫,
·其它杀真菌剂类,例如噻二唑素(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(fluazinam)、藻菌磷(fosetyl)、藻菌磷-铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯、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),
·嗜球果伞素(strobilurins),例如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、氟硫菌酯(fluoxastrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)或肟菌酯(trifloxystrobin),
·次磺酸衍生物类,例如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)或对甲抑菌灵(tolylfluanid),
·肉桂酰胺类及类似化合物,例如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
合成实施例
在下列合成实施例中描述的程序用于通过对起始化合物进行适当改性而制备另外化合物I。由此得到的化合物及其物理数据列举在下表中。
实施例1:4-乙酰基-N-吡啶-4-基甲基苯基磺酰胺的制备
在-10℃下,将4.95g(45.7mmol)4-(氨基甲基)吡啶(4-吡啶甲基胺)在10ml乙醚中的溶液滴加到10g(45.7mmol)4-乙酰基磺酰氯在150ml乙醚中的溶液中,然后在20-25℃下将溶液搅拌约18小时。采用吸滤过滤产物,并且用稀NaHCO3溶液和水洗涤残余物,然后干燥。由此得到5.2g熔点为162-167℃的标题化合物。
实施例2:4-(1-乙氧基亚氨基乙基)-N-吡啶-4-基甲基苯基磺酰胺的制备
将0.42g 40%浓度的O-乙基羟胺水溶液加入0.4g(1.3mmol)实施例1的化合物在20ml甲醇中的溶液中。使用10%浓度的盐酸,将混合物酸化到pH为4,然后在20-25℃下将溶液搅拌约18小时。将反应溶液倒入水中并用NaHCO3调节到pH为8。然后用甲基叔丁基醚(MtBE)萃取混合物,用水洗涤合并的有机相并干燥。除去溶剂得到0.4g粘性油状的标题化合物。
1H-NMR(δ,CDCl3):8.5(d,2H);7.5(m,4H);7.1(d,2H);5.0(t,1H);4.25(q,2H);4.1(d,2H);2.25(s,3H);1.3(t,3H)。
实施例3:4-(1-乙氧基亚氨基乙基)-N-甲基-N-吡啶-4-基甲基苯基磺酰胺的制备
将0.4g(1.2mmol)实施例2的化合物加入0.04g(1.32mmol)NaH(纯度95%)在50ml二甲基甲酰胺(DMF)中的浆液中,然后在20-25℃下将混合物搅拌10分钟。然后滴加0.17g(1.2mmol)碘代甲烷在10mol DMF中的溶液,并且在20-25℃下将合并的反应溶液搅拌约18小时,倒入水中,然后用MtBE萃取。用水洗涤有机相,然后干燥。除去溶剂得到0.3g粘性油状的标题化合物。
1H-NMR(δ,CDCl3):8.6(d,2H);7.8(m,4H);7.25(d,2H);4.25(q,2H);4.1(d,2H);2.6(s,3H);2.25(s,3H);1.25(t,3H)。
表1
编号 | X | R1 | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];1H-NMRδ[ppm];MS m/e[M+H+]) |
I-1 | 4-(C[CH3]=NOCH3)-C6H4 | H | H | H | H | H | 4.2(2H);4.0(3H);2.25(3H) |
I-2 | 4-(C[CH3]=NOCH2CH3)-C6H4 | H | H | H | H | H | 4.25(2H);4.2(2H);2.25(3H);1.3(3H) |
I-3 | 4-(C[CH3]=NOCH2CH=CH2)-C6H4 | H | H | H | H | H | 5.2(2H);4.7(2H);4.05(2H);2.25(3H) |
I-4 | 4-(C[CH3]=NOCH(CH3)2)-C6H4 | H | H | H | H | H | 4.45(1H);4.2(2H);2.25(3H);1.3(6H) |
I-5 | 4-(C[CH3]=NOCH2C≡CH)-C6H4 | H | H | H | H | H | 4.8(2H);4.2(2H);2.5(1H);2.3(3H) |
I-6 | 4-(C[CH3]=NO(CH2)5CH3)-C6H4 | H | H | H | H | H | 4.2(2H);4.1(2H);2.25(3H);0.9(3H) |
I-7 | 4-(C[CH3]=NOCH2C6H5)-C6H4 | H | H | H | H | H | 5.3(2H);4.25(2H);2.25(3H) |
I-8 | 4-(C[CH3]=NOCH3)-C6H4 | CH3 | H | H | H | H | 4.2(2H);4.05(3H);2.65(3H);2.25(3H) |
I-9 | 4-(C[CH3]=NOCH2CH3)-C6H4 | CH3 | H | H | H | H | 4.25(2H);4.2(2H); |
编号 | X | R1 | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];1H-NMRδ[ppm];MS m/e[M+H+]) |
2.7(3H);1.35(3H) | |||||||
I-10 | 4-(C[CH3]=NOCH2CH3)-C6H4 | CH2CH3 | H | H | H | H | 4.3(2H);4.2(2H);3.2(2H);2.2(3H);1.3(3H);0.9(3H) |
I-11 | 4-(C[CH3]=NOCH2CH3)-C6H4 | CH2C≡CH | H | H | H | H | 4.35(2H);4.25(2H);4.0(2H);2.25(1H) |
I-12 | 4-(C[CH3]=NOCH2CH3)-C6H4 | C6H5CH2 | H | H | H | H | 4.3(2H);4.25(2H);4.2(2H);2.25(3H) |
I-13 | 4-(C[CH3]=NOCH2CH3)-C6H4 | CH2CH=CH2 | H | H | H | H | 5.5(1H);5.0(2H);4.3(2H);3.75(2H) |
I-14 | 4-COOCH3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.45(1H);8.0(1H);7.4(1H);4.5(2H) | |
I-15 | 4-CH3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.1(1H);7.3(1H);4.65(2H);1.3(9H) | |
I-16 | 4-OCH3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.1(1H);4.6(1H);3.0(1H);1.3(6H) | |
I-17 | 4-Cl-C6H4 | H | -CH=CH-CH=CH- | H | H | m/e 333 | |
I-18 | 2,5-Cl2-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 367 | |
I-19 | 1-萘基 | H | -CH=CH-CH=CH- | H | H | m/e 349 | |
I-20 | 2-CH3-6-CF3-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 381 | |
I-21 | 2-Cl-5-OCH3-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 363 | |
I-22 | 2,4-Cl2-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 367 | |
I-23 | 4-CN-C6H4 | H | -CH=CH-CH=CH- | H | H | m/e 324 | |
I-24 | 2,6-Cl2-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 367 |
编号 | X | R1 | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];1H-NMRδ[ppm];MS m/e[M+H+]) |
I-25 | 2-Br-C6H4 | H | -CH=CH-CH=CH- | H | H | m/e 379 | |
I-26 | 2,3-Cl2-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 367 | |
I-27 | 3,4-(OCH3)2-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 358 | |
I-28 | 2-CH3-6-Cl-C6H3 | H | -CH=CH-CH=CH- | H | H | m/e 347 | |
I-29 | 2-Cl-C6H4 | H | -CH=CH-CH=CH- | H | H | m/e 333 | |
I-30 | C6H5 | H | -CH=CH-CH=CH- | H | H | 8.45(1H);8.0(1H);7.4(1H);4.5(2H) | |
I-31 | 4-C(CH3)3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.1(1H);7.3(1H);4.65(2H);1.3(9H) | |
I-32 | 4-CH(CH3)2-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.1(1H);4.6(1H);3.0(1H);1.3(6H) | |
I-33 | 4-OCF3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.75(1H);8.0(1H);5.8(1H);4.7(2H) | |
I-34 | 4-OCF2CHF2-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.8(1H);4.7(2H) | |
I-35 | 4-COCH3-C6H4 | H | -CH=CH-CH=CH- | H | H | 8.8(1H);7.3(1H);4.6(2H);2.6(3H) | |
I-36 | 4-(C[CH3]=NOCH3)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.2(NH);4.6(2H);4.0(3H);2.2(3H) | |
I-37 | 4-(C[CH3]=NOCH2CH3)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.0(NH);4.6(2H);4.3(3H);2.3(3H);1.35(3H) | |
I-38 | 4-(C[CH3]=NOCH(CH3)2)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.1(NH);4.6(2H);4.5(3H);2.25(3H);1.3(6H) |
编号 | X | R1 | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];1H-NMRδ[ppm];MS m/e[M+H+]) |
I-39 | 4-(C[CH3]=NOCH2CH=CH2)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.3(NH);5.2(2H);4.75(2H);4.6(2H);2.35(3H) | |
I-40 | 4-(C[CH3]=NOCH2C≡CH)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.1(NH);4.8(2H);4.6(2H);2.5(2H);2.3(3H) | |
I-41 | 4-(C[CH3]=NO(CH2)5CH3)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.2(NH);4.6(2H);4.2(2H);2.25(2H);0.9(3H) | |
I-42 | 4-(C[CH3]=NOCH2C6H5)-C6H4 | H | -CH=CH-CH=CH- | H | H | 5.3(2H);5.2(NH);4.8(2H);2.3(3H) | |
I-43 | C6H5 | CH3 | -CH=CH-CH=CH- | H | H | 4.6(2H);2.7(3H) | |
I-44 | 5-Cl-噻吩-2-基 | H | H | H | H | H | m/e 339 |
I-45 | 噻吩-2-基 | H | H | H | H | H | m/e 305 |
I-46 | 5-([4-C(CH3)3]-C6H4)-噻吩-2-基 | H | H | H | H | H | 166 |
I-47 | 5-Br-噻吩-2-基 | H | H | H | H | H | 148 |
I-48 | 4-NO2-5-Cl-噻吩-2-基 | H | H | H | H | H | 182 |
I-49 | 5-Cl-1,3-(CH3)2-1H-吡唑-4-基 | H | H | H | H | H | 147 |
I-50 | 3-Br-2,5-Cl2-噻吩-4-基 | H | H | H | H | H | 106 |
I-51 | 1-CH3-1H-咪唑-4-基 | H | H | H | H | H | 125 |
I-52 | 5-(4-叔丁基苯基)噻吩-2-基 | H | H | H | H | H | 166 |
I-53 | 5-氯-1,3-二甲基-1H-吡唑-4-基 | H | H | H | H | H | 147 |
I-54 | 5-溴噻吩-2-基 | H | H | H | H | H | 148 |
I-55 | 5-氯-4-硝基噻吩-2-基 | H | H | H | H | H | 182 |
编号 | X | R1 | R2 | R3 | R4 | R5 | 物理数据(熔点[℃];1H-NMRδ[ppm];MS m/e[M+H+]) |
I-56 | 1-甲基-1H-咪唑-4-基 | H | H | H | H | H | 125 |
I-57 | 4-溴-2,5-二氯噻吩-3-基 | H | H | H | H | H | 106 |
I-58 | 5-联苯-4-基噻吩-2-基 | H | H | H | H | H | 204 |
I-59 | 5-(4-三氟甲氧基苯基)噻吩-2-基 | H | H | H | H | H | 138 |
I-60 | 5-(4-丙基苯基)噻吩-2-基 | H | H | H | H | H | 144 |
I-61 | 5-(4-乙基苯基)噻吩-2-基 | H | H | H | H | H | 144 |
I-62 | 5-(3-三氟甲基苯基)噻吩基 | H | H | H | H | H | 130 |
I-63 | 5-(4-氯苯基)噻吩-2-基 | H | H | H | H | H | 176 |
I-64 | 5-(4-三氟甲基苯基)噻吩基 | H | H | H | H | H | 165 |
I-65 | 5-(4-甲氧基苯基)噻吩-2-基 | H | H | H | H | H | 175 |
I-66 | 5-(4-三氟甲基苯基)噻吩-2-基 | 炔丙基 | H | H | H | H | 116 |
I-67 | 5-(4-三氟甲基苯基)噻吩-2-基 | 正丙基 | H | H | H | H | 97 |
I-68 | 5-(4-三氟甲基苯基)噻吩-2-基 | 甲基 | H | H | H | H | 101 |
I-69 | 5-(4-异丙基苯基)噻吩-2-基 | H | H | H | H | H | 125 |
I-70 | 5-溴噻吩-2-基 | H | -CH=CH-CH=CH- | H | H | 137 | |
I-71 | 5-(4-三氟甲基苯基)噻吩-2-基 | H | -CH=CH-CH=CH- | H | H | 180 | |
I-72 | 4-叔丁基苯基 | 甲基 | -CH=CH-CH=CH- | H | H | 145-148 |
对有害真菌活性的实施例
由下列实验说明式I化合物的杀真菌作用:
将活性化合物单独或联合制成含有0.25重量%活性化合物的丙酮或DMSO储液。将1重量%的乳化剂UniperolEL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)加入该溶液中,并用水将该混合物稀释到所需浓度。
应用实施例1:对茄链格孢菌(Alternaria solani)引起的西红柿早疫病的活性
用具有下述活性化合物浓度的水悬浮液对栽培品种为“GoldenePrinzessin”的盆栽植物的叶子喷雾至滴流点。第二天将叶子用茄链格孢菌(Alternaria solani)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20-22℃下的水蒸气饱和室中。5天后,未处理但侵染的对照植物上的早疫病发展到可以以%肉眼测定侵染的程度。
在该测试中,用250ppm活性化合物I-2至I-6、I-14、I-15、I-17、I-30至I-34、I-36至I-42或I-45处理过的植物具有不超过30%的侵染,而未处理的植物受到100%侵染。
应用实施例2:对单丝壳白粉菌(Sphaerotheca fuliginea)引起的黄瓜叶子上的霉菌的活性,保护性应用
在子叶阶段用具有下述活性化合物浓度的水悬浮液对栽培品种为“Chinese Snake”的盆栽黄瓜幼苗的叶子喷雾至滴流点。在喷雾涂层干燥后20小时,对植物接种黄瓜霉菌(单丝壳白粉菌)的含水孢子悬浮液。然后将植物在20-24℃和60-80%相对空气湿度下的温室中培育7天。以子叶面积的侵染%肉眼测定霉菌发展的程度。
在该测试中,用250ppm活性化合物I-1至I-5、I-15、I-18、I-30、I-32、I-33、I-34、I-37至I-40、I-42或I-45处理过的植物显示不超过30%的侵染,而未处理的植物受到100%侵染。
Claims (8)
1.一种式I的磺酰胺,
其中取代基如下:
R1是H、C1-C4烷基、C1-C4烷氧基、C2-C4链烯基、C2-C4链炔基或苄基;
R2、R3、R4、R5相互独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1卤代甲基;
R2和R3还可以一起形成苯基、环戊基或环己基环,这些环可以带有两个基团R2’和R3’;
R2’、R3’相互独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1卤代甲基;
在情况a)下,如果R2、R3、R4和R5是氢,则:
X是由-C(R6)=NOR7基团取代的苯基,其中
R6是C1-C4烷基和
R7是C1-C8烷基、苄基、C2-C4链烯基、C1-C4卤代烷基、C2-C4卤代链烯基、C2-C4链炔基或C2-C4卤代链炔基;以及
在情况b)下,如果基团R2、R3、R4和R5中的至少一个不是氢,则:
X是苯基,萘基或由碳原子连接且含有1-4个选自O、N和S的杂原子的5元或6元饱和、部分不饱和或芳族杂环,其中X可以带有1-4个Ra基团:
Ra是卤素、氰基、硝基、C1-C8烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C4烷基羰基、C1-C4烷氧基羰基、-C(R6)=NOR7、C1-C4烷基氨基羰基、二(C1-C4烷基)氨基羰基或者苯基或苯氧基,其中环可以带有1-3个Rb基团:
Rb是卤素、C1-C4烷基、C1-C4烷氧基、C1卤代烷基或C1卤代烷氧基;
Ra或Rb还可以是C3-C4亚烷基或C4亚烯基,其与和它连接的苯基环的两个相邻成环原子一起形成可以由一个或多个上述Ra或Rb基团取代的环。
2.根据权利要求1的式I化合物,其中R2、R3、R4和R5相互独立地是氢、甲基、氟、氯、CF3、OCF3或OCHF2。
3.根据权利要求1或2的式I化合物,其中R1是氢、甲基、甲氧基、乙氧基、烯丙基或炔丙基。
4.根据权利要求1-3中任何一项的式I化合物,其中X是在对位取代的苯基环。
5.根据权利要求1-3中任何一项的式I化合物,其中X是芳族杂环。
7.一种适于防治有害真菌的组合物,该组合物含有固体或液体载体和权利要求1的式I化合物。
8.一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权利要求1的式I化合物处理真菌或处理需要进行保护以免受真菌侵害的材料、植物、土壤或种子。
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BRPI0909041A2 (pt) * | 2008-03-14 | 2015-07-28 | Basf Se | Compostos, uso de compostos, processo para preparar compostos, composições agroquímicas, método para combater fungos fitopatogênicos, e, semente. |
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WO2009141241A2 (en) * | 2008-05-20 | 2009-11-26 | Basf Se | Substituted pyridin-4-ylmethyl sulfonamides |
WO2009141291A1 (en) * | 2008-05-20 | 2009-11-26 | Basf Se | Substituted heteroarylmethyl sulfonamides |
CN102036560A (zh) | 2008-05-21 | 2011-04-27 | 巴斯夫欧洲公司 | 取代吡啶-4-基甲基磺酰胺 |
JP2013538784A (ja) * | 2010-10-01 | 2013-10-17 | ラクオリア創薬株式会社 | Trpm8拮抗剤としてのスルファモイル安息香酸ヘテロ二環性誘導体 |
CN103619818A (zh) * | 2011-06-20 | 2014-03-05 | 纳幕尔杜邦公司 | 用于治疗蠕虫感染的杂环化合物 |
CN103958476A (zh) * | 2011-11-28 | 2014-07-30 | 纳幕尔杜邦公司 | N-(4-喹啉基甲基)磺酰胺衍生物以及它们作为驱肠虫剂的用途 |
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US4874775A (en) * | 1985-06-11 | 1989-10-17 | Eli Lilly And Company | Agriculturally useful sulfonamides |
US4699652A (en) | 1985-07-22 | 1987-10-13 | Hoffmann-La Roche Inc. | Fungicidal pyridine derivatives for use in agriculture |
US6500865B1 (en) * | 1998-07-31 | 2002-12-31 | Eli Lilly And Company | Sulfonamide derivatives |
US6586617B1 (en) * | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
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CN101888999B (zh) * | 2007-12-05 | 2013-12-11 | 巴斯夫欧洲公司 | 吡啶基甲基磺酰胺化合物 |
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KR20060070563A (ko) | 2006-06-23 |
US7388018B2 (en) | 2008-06-17 |
NZ546218A (en) | 2008-07-31 |
ECSP066463A (es) | 2006-11-16 |
US20060293314A1 (en) | 2006-12-28 |
ATE453625T1 (de) | 2010-01-15 |
US20080221177A1 (en) | 2008-09-11 |
CO5660289A2 (es) | 2006-07-31 |
EA200600490A1 (ru) | 2006-08-25 |
EA008948B1 (ru) | 2007-10-26 |
AR045777A1 (es) | 2005-11-09 |
MA28050A1 (fr) | 2006-07-03 |
EP1663976B1 (de) | 2009-12-30 |
AU2004278095B2 (en) | 2010-06-24 |
AU2004278095A1 (en) | 2005-04-14 |
MXPA06002500A (es) | 2006-06-20 |
JP4477006B2 (ja) | 2010-06-09 |
BRPI0414410A (pt) | 2006-11-14 |
CR8312A (es) | 2006-12-07 |
UA82124C2 (uk) | 2008-03-11 |
WO2005033081A1 (de) | 2005-04-14 |
AP2006003564A0 (en) | 2006-04-30 |
ZA200602966B (en) | 2007-07-25 |
EP1663976A1 (de) | 2006-06-07 |
DE502004010595D1 (de) | 2010-02-11 |
IL173854A0 (en) | 2006-07-05 |
CA2537486A1 (en) | 2005-04-14 |
JP2007505849A (ja) | 2007-03-15 |
AR045767A1 (es) | 2005-11-09 |
CN100406442C (zh) | 2008-07-30 |
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