CN101115723B - 吡唑甲酰苯胺、其制备方法以及用于防治有害真菌的包含它们的试剂 - Google Patents
吡唑甲酰苯胺、其制备方法以及用于防治有害真菌的包含它们的试剂 Download PDFInfo
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- CN101115723B CN101115723B CN2006800044802A CN200680004480A CN101115723B CN 101115723 B CN101115723 B CN 101115723B CN 2006800044802 A CN2006800044802 A CN 2006800044802A CN 200680004480 A CN200680004480 A CN 200680004480A CN 101115723 B CN101115723 B CN 101115723B
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- Prior art keywords
- chloro
- fluoro
- methyl
- difluorophenyl
- dichlorophenyl
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- 238000000034 method Methods 0.000 title claims abstract description 14
- WMZYZYFPPQOFKY-UHFFFAOYSA-N n-phenyl-1h-pyrazole-3-carboxamide Chemical class C1=CNN=C1C(=O)NC1=CC=CC=C1 WMZYZYFPPQOFKY-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 title description 16
- 244000053095 fungal pathogen Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 239000000460 chlorine Substances 0.000 claims abstract description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 239000011737 fluorine Substances 0.000 claims abstract description 30
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 30
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 18
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 229940084434 fungoid Drugs 0.000 claims description 10
- ZKBNUNIVNISNDB-UHFFFAOYSA-N [Cl].FC Chemical compound [Cl].FC ZKBNUNIVNISNDB-UHFFFAOYSA-N 0.000 claims description 9
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 4
- 230000002538 fungal effect Effects 0.000 claims description 2
- KYXNOBUGJXDOIO-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,3,4-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1F KYXNOBUGJXDOIO-UHFFFAOYSA-N 0.000 claims 1
- SAEWEAKBGDVOPX-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F SAEWEAKBGDVOPX-UHFFFAOYSA-N 0.000 claims 1
- HDWGAKWQBOMENH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 HDWGAKWQBOMENH-UHFFFAOYSA-N 0.000 claims 1
- OXBRSAWHLLAWFH-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F OXBRSAWHLLAWFH-UHFFFAOYSA-N 0.000 claims 1
- DBTUGJPPHBREQB-UHFFFAOYSA-N N1N=CC(=C1)C(=O)N.CF Chemical compound N1N=CC(=C1)C(=O)N.CF DBTUGJPPHBREQB-UHFFFAOYSA-N 0.000 claims 1
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 22
- 241000233866 Fungi Species 0.000 abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- -1 methoxyl group Chemical group 0.000 description 164
- 239000002585 base Substances 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 17
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- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
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- 239000000047 product Substances 0.000 description 14
- 235000009566 rice Nutrition 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 241000209140 Triticum Species 0.000 description 12
- 235000021307 Triticum Nutrition 0.000 description 11
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- 150000003818 basic metals Chemical class 0.000 description 10
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 1
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 1
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- UVECLJDRPFNRRQ-UHFFFAOYSA-N ethyl trifluoromethanesulfonate Chemical compound CCOS(=O)(=O)C(F)(F)F UVECLJDRPFNRRQ-UHFFFAOYSA-N 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- IQECZGDVZMVJSH-UHFFFAOYSA-N furan 1H-pyrazole Chemical class O1C=CC=C1.N1N=CC=C1 IQECZGDVZMVJSH-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
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- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
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- 229940050176 methyl chloride Drugs 0.000 description 1
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- 229940017219 methyl propionate Drugs 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- NOTMCFVPRDIUAV-UHFFFAOYSA-N n-[2-(4-bromophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Br)C=C1 NOTMCFVPRDIUAV-UHFFFAOYSA-N 0.000 description 1
- DRTSCVXACFOXNK-UHFFFAOYSA-N n-chloro-2-phenylaniline Chemical class ClNC1=CC=CC=C1C1=CC=CC=C1 DRTSCVXACFOXNK-UHFFFAOYSA-N 0.000 description 1
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- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004714 phosphonium salts 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
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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
- 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
- 238000000746 purification Methods 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
- KOPFEFZSAMLEHK-UHFFFAOYSA-N pyrazolecarboxylic acid Natural products OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 241000894007 species Species 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
- 230000004763 spore germination Effects 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
- 239000011550 stock solution Substances 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
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-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
- 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
- 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
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical class C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Insulated Conductors (AREA)
- Catching Or Destruction (AREA)
Abstract
本发明涉及式(I)的吡唑甲酰苯胺,其中各变量如下所定义:n为0或2;m为2或3;X1为氟或氯;X2为卤素;Y为CN、NO2、C1-C4烷基、C1-C4卤代烷基、甲氧基或甲硫基;p为0或1;R1为氟、氯、溴、C1-C4烷基或C1-C4卤代烷基;R2为氢或卤素;R3为氢、甲基或乙基;W为O或S;条件是若a)W=O,R1=甲基且R3为氢,则R2不为氟,或b)W=O,n=0,m=2,p=0,R2和R3为氢,则R1不为三氟甲基或二氟甲基。本发明还涉及制备这些化合物的方法,包含它们的试剂以及使用它们防治病原性真菌的方法。
Description
本发明涉及式I的吡唑甲酰苯胺:
其中各变量如下所定义:
n为0或2;
m为2或3;
X1为氟或氯;
X2为卤素;
Y为CN、NO2、C1-C4烷基、C1-C4卤代烷基、甲氧基或甲硫基;
p为0或1;
R1为氟、氯、溴、C1-C4烷基或C1-C4卤代烷基;
R2为氢或卤素;
R3为氢、甲基或乙基;
W为O或S;
条件是若
a)W=O,R1=甲基且R3为氢,则R2不为F,或
b)W=O,n=0,m=2,p=0,R2和R3为氢,则R1不为三氟甲基或二氟甲基。
这里在多重取代的情况下,取代基X1和X2可以相互独立地具有不同含义。
此外,本发明涉及制备这些化合物的方法、包含它们的组合物以及它们在防治有害真菌,尤其是葡萄孢属(Botrytis)中使用的方法。
具有杀真菌作用的吡唑甲酰苯胺由文献已知。因此,例如EP-A 545 099和EP-A 589 301描述了在联苯基上单取代的这类联苯基酰替苯胺。
WO 00/14071描述了特定的1,3-二甲基-5-氟吡唑甲酰苯胺及其杀真菌作用。
在联苯基上具有特定的三重取代的吡唑甲酰苯胺由WO 03/070705和JP-A 2001/302605已知。
WO 2004/103975尤其提供了碘代吡唑甲酰苯胺,它们与本发明化合物I的不同尤其在于它们具有碘取代基而不是R1。
本发明的目的是提供其杀真菌作用好于现有技术化合物的吡唑甲酰苯胺。
我们发现该目的由开头所定义的化合物I实现。此外,我们发现了制备这些化合物的方法、包含它们的组合物以及它们在防治有害真菌中使用的方法。
与已知化合物相比,式I化合物对有害真菌更为有效。
式I化合物可以呈生物活性可能不同的不同晶型。它们也形成本发明主题的一部分。
在式I中,卤素为氟、氯、溴或碘,优选氟或氯;
C1-C4烷基为甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基,优选甲基或乙基;
C1-C4卤代烷基为部分或完全卤代的C1-C4烷基,其中卤原子尤其为氟和/或氯,即例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2-氯-2-氟乙基、2,2,2-三氟乙基、2-氯-1,1,2-三氟乙基、2-氯-2,2-二氟乙基、2-溴-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、1,1,2,2-四氟乙基、1,1,2,2-四氯乙基、五氟乙基、2,2,3,3-四氟-1-丙基、1,1,2,3,3,3-六氟-1-丙基、1,1,1,3,3,3-六氟-2-丙基、七氟-1-丙基、七氟-2-丙基、2,2,3,3,4,4,4-七氟-1-丁基或九氟-1-丁基,尤其是卤代甲基,特别优选CH2-Cl、CH(Cl)2、CH2-F、CH(F)2、CF3、CHFCl、CF2Cl或CF(Cl)2。
化合物I通常通过使式II的羰基卤以本身已知的方式(例如J.March,Advanced Organic Chemistry,第2版,第382页及随后各页,McGraw-Hill,1977)在碱存在下与式III的苯胺反应而得到:
在式II中,基团Hal表示卤原子,如氟、氯、溴和碘,尤其是氟、氯或溴。该反应通常在-20℃至100℃,优选0-50℃的温度下进行。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,还有二氯甲烷、二甲亚砜和二甲基甲酰胺,特别优选甲苯、二氯甲烷和四氢呋喃。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,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,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属和碱土金属碳酸盐,如碳酸锂和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,以及有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾和二甲氧基镁,此外还有有机碱,例如叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如可力丁、卢剔啶和4-二甲基氨基吡啶,以及双环胺。
特别优选使用三乙胺和吡啶。
基于化合物II,碱通常以等摩尔量使用。然而,它们还可以过量5-30mol%,优选5-10mol%使用,或者若使用叔胺,则合适的话还可以将它们用作溶剂。
原料通常以等摩尔量相互反应。就产率而言,可能有利的是基于III过量1-20mol%,优选1-10mol%使用II。
制备化合物I所需的式II和III的原料是已知的或者可以类似于已知化合物合成(Helv.Chim.Acta,60,978(1977);Zh.Org.Khim.,26,1527(1990);Heterocycles 26,1885(1987);Izv.Akad.Nauk.SSSR Ser.Khim.,2160(1982);THL 28,593(1987);THL 29,5463(1988))。
此外,已经发现式I化合物通过已知方式使式IV的羧酸与式III的苯胺在脱水剂和合适的话有机碱存在反应而得到。
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷、茴香醚和四氢呋喃,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,还有二甲亚砜和二甲基甲酰胺,特别优选二氯甲烷、甲苯和四氢呋喃。
还可以使用所述溶剂的混合物。
合适的脱水剂是1,1′-羰基二咪唑,二(2-氧代-3-噁唑烷基)磷酰氯,碳二亚胺,如N,N′-二环己基碳二亚胺、N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺,鏻盐,如(苯并三唑-1-基氧基)三(二甲基氨基)鏻六氟磷酸盐、溴代三吡咯烷基鏻六氟磷酸盐、溴代三(二甲基氨基)鏻六氟磷酸盐、氯代三吡咯烷基鏻六氟磷酸盐,脲鎓和硫脲鎓盐,如O-(苯并三唑-1-基)-N,N,N′,N′-四甲基脲鎓六氟磷酸盐、O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲鎓六氟磷酸盐、S-(1-氧桥-2-吡啶基)-N,N,N′,N′-四甲基硫脲鎓四氟硼酸盐、O-(2-氧代-1(2H)吡啶基)-N,N,N′,N′-四甲基脲鎓四氟硼酸盐、O-[(乙氧羰基)氰基亚甲基氨基]-N,N,N′,N′-四甲基脲鎓四氟硼酸盐,碳鎓盐,如(苯并三唑-1-基氧基)二吡咯烷基碳鎓六氟磷酸盐、(苯并三唑-1-基氧基)二哌啶子基碳鎓六氟磷酸盐、O-(3,4-二氢-4-氧代-1,2,3-苯并三唑-3-基)-N,N,N′,N′-四甲基脲鎓四氟硼酸盐、氯-N′,N′-二(四亚甲基)甲脒四氟硼酸盐、氯代二吡咯烷基碳鎓六氟磷酸盐、氯-N,N,N′,N′-二(五亚甲基)甲脒四氟硼酸盐,咪唑鎓盐,如2-氯-1,3-二甲基咪唑烷鎓四氟硼酸盐,优选1,1′-羰基二咪唑、二(2-氧代-3-噁唑烷基)磷酰氯、N,N′-二环己基碳二亚胺和N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺。
合适的有机碱是叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代的吡啶,如可力丁、卢剔啶和4-二甲基氨基吡啶,还有双环胺。特别优选使用三乙胺和吡啶。碱通常基于化合物IV过量10-200mol%,优选50-150mol%使用。
原料通常以等摩尔量相互反应。就产率而言,可能有利的是过量1-20mol%,优选1-10mol%使用所述化合物之一。脱水剂通常过量5-100mol%,优选5-60mol%使用。
制备化合物I所需的式III和IV的原料是已知的或者可以类似于已知化合物而合成。
其中R3为甲基或乙基的式I化合物可以通过使其中R3=H的式I化合物以本身已知的方式在碱存在下与烷基化试剂反应而得到:
I(R3=H) I(R3≠H)
合适的溶剂是脂族烃类,如戊烷、己烷、环己烷和石油醚,芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类,如二氯甲烷、氯仿和氯苯,醚类,如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷,茴香醚和四氢呋喃,还有二甲亚砜和二甲基甲酰胺,特别优选乙醚、叔丁基甲基醚、四氢呋喃和二甲基甲酰胺。
还可以使用所述溶剂的混合物。
合适的烷基化试剂(XCH3或XC2H5)是烷基卤,如甲基碘、乙基碘、甲基溴、乙基溴、甲基氯、乙基氯,全氟烷基磺酸烷基酯,如三氟甲基磺酸甲酯和三氟甲基磺酸乙酯,烷基磺酸烷基酯,如甲基磺酸甲酯和甲基磺酸乙酯,芳基磺酸烷基酯,如对甲苯基磺酸甲酯和对甲苯基磺酸乙酯,氧鎓盐,如三甲基氧鎓四氟硼酸盐和三乙基氧鎓四氟硼酸盐。
特别优选甲基碘、乙基碘、甲基溴、乙基溴、甲基氯和乙基氯。
合适的碱通常为无机化合物,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,碱金属氨化物,如氨化锂、氨化钠和氨化钾,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钠、碳酸钾和碳酸钙,还有碱金属碳酸氢盐,如碳酸氢钠,或有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,还有碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾和叔丁醇钾。
特别优选碳酸钠、碳酸钾、氢化钠、氢化钾、丁基锂和叔丁醇钾。
基于化合物I,碱通常以等摩尔量使用。然而,它们还可以过量5-30mol%,优选5-10mol%使用。
原料通常以大约等摩尔量相互反应。就产率而言,可能有利的是过量1-20mol%,优选1-10mol%使用烷基化试剂。
考虑到化合物I的生物活性,优选变量的下列含义,在每种情况下单独或组合:
n为0;
m为3;
X1为氯;
X2为氟或氯,优选氟;
Y为C1-C4烷基、C1-C4卤代烷基或甲氧基,
尤其是甲基、二氟甲基、三氟甲基或甲氧基;
特别优选甲基或三氟甲基;
p为0;
R1为氟、氯、C1-C4烷基或C1-C4卤代烷基,尤其是F、CI、甲基、氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基或三氟甲基;特别优选甲基、氟甲基、二氟甲基、氯氟甲基或三氟甲基,尤其是二氟甲基或三氟甲基;
非常特别优选二氟甲基;
R2为氢、氟或氯,尤其是氢或氯,特别优选氢;
R3为氢或甲基,尤其是氢;
W为氧。
在m=3的情况下,基团X2优选位于2,4,5-或3,4,5-位,尤其是3,4,5-位。
特别优选具有下列取代基组合的化合物I,其中取代基如下所定义:
X2为氟或氯;
Y为甲基、二氟甲基、三氟甲基或甲氧基;
R1为F、氯、甲基、氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基、三氟甲基;
R2为氢、氟或氯;
R3为氢或甲基;
W为氧。
此外还优选具有下列含义的取代基的下列组合:
X2为氟或氯;
n为0;
p为0;
R1为F、氯、甲基、氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基或三氟甲基,尤其是氟、氯、氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基或三氟甲基;
R2为氢、氟或氯;
R3为氢;
W为氧。
还优选其中m=2的化合物I,尤其是其中R1为甲基、氟甲基、氯氟甲基或一氯二氟甲基和/或R2为氢或氯,尤其是氢的那些。这里基团X优选位于2,4-或3,4-位,尤其是3,4-位。
尤其考虑到它们作为杀真菌剂的用途,优选通式I-A和I-B的化合物:
表A
序号 | B | R1 |
1 | 2,3-二氯苯基 | CF3 |
2 | 2,4-二氯苯基 | CF3 |
3 | 2,5-二氯苯基 | CF3 |
4 | 2,6-二氯苯基 | CF3 |
5 | 3,4-二氯苯基 | CF3 |
6 | 3,5-二氯苯基 | CF3 |
7 | 2,3-二氟苯基 | CF3 |
8 | 2,4-二氟苯基 | CF3 |
9 | 2,5-二氟苯基 | CF3 |
10 | 2,6-二氟苯基 | CF3 |
11 | 3,4-二氟苯基 | CF3 |
12 | 3,5-二氟苯基 | CF3 |
13 | 2-氯-3-氟苯基 | CF3 |
14 | 2-氯-4-氟苯基 | CF3 |
15 | 2-氯-5-氟苯基 | CF3 |
16 | 2-氯-6-氟苯基 | CF3 |
序号 | B | R1 |
17 | 3-氯-2-氟苯基 | CF3 |
18 | 3-氯-4-氟苯基 | CF3 |
19 | 3-氯-5-氟苯基 | CF3 |
20 | 3-氯-6-氟苯基 | CF3 |
21 | 4-氯-2-氟苯基 | CF3 |
22 | 4-氯-3-氟苯基 | CF3 |
23 | 2,3,4-三氯苯基 | CF3 |
24 | 2,3,5-三氯苯基 | CF3 |
25 | 2,3,6-三氯苯基 | CF3 |
26 | 2,4,5-三氯苯基 | CF3 |
27 | 2,4,6-三氯苯基 | CF3 |
28 | 3,4,5-三氯苯基 | CF3 |
29 | 2,3,4-三氟苯基 | CF3 |
30 | 2,3,5-三氟苯基 | CF3 |
31 | 2,3,6-三氟苯基 | CF3 |
32 | 2,4,5-三氟苯基 | CF3 |
33 | 2,4,6-三氟苯基 | CF3 |
34 | 3,4,5-三氟苯基 | CF3 |
35 | 2-氯-3,4-二氟苯基 | CF3 |
36 | 2-氯-4,5-二氟苯基 | CF3 |
37 | 2-氯-5,6-二氟苯基 | CF3 |
38 | 2-氯-3,5-二氟苯基 | CF3 |
39 | 2-氯-3,6-二氟苯基 | CF3 |
40 | 2-氯-4,6-二氟苯基 | CF3 |
41 | 3-氯-2,4-二氟苯基 | CF3 |
42 | 3-氯-2,5-二氟苯基 | CF3 |
43 | 3-氯-2,6-二氟苯基 | CF3 |
44 | 3-氯-4,5-二氟苯基 | CF3 |
45 | 3-氯-4,6-二氟苯基 | CF3 |
46 | 3-氯-5,6-二氟苯基 | CF3 |
47 | 4-氯-2,3-二氟苯基 | CF3 |
48 | 4-氯-2,5-二氟苯基 | CF3 |
49 | 4-氯-2,6-二氟苯基 | CF3 |
50 | 4-氯-3,5-二氟苯基 | CF3 |
序号 | B | R1 |
51 | 2-氟-3,4-二氯苯基 | CF3 |
52 | 2-氟-4,5-二氯苯基 | CF3 |
53 | 2-氟-5,6-二氯苯基 | CF3 |
54 | 2-氟-3,5-二氯苯基 | CF3 |
55 | 2-氟-3,6-二氯苯基 | CF3 |
56 | 2-氟-4,6-二氯苯基 | CF3 |
57 | 3-氟-2,4-二氯苯基 | CF3 |
58 | 3-氟-2,5-二氯苯基 | CF3 |
59 | 3-氟-2,6-二氯苯基 | CF3 |
60 | 3-氟-4,5-二氯苯基 | CF3 |
61 | 3-氟-4,6-二氯苯基 | CF3 |
62 | 3-氟-5,6-二氯苯基 | CF3 |
63 | 4-氟-2,3-二氯苯基 | CF3 |
64 | 4-氟-2,5-二氯苯基 | CF3 |
65 | 4-氟-2,6-二氯苯基 | CF3 |
66 | 4-氟-3,5-二氯苯基 | CF3 |
67 | 2,3-二氯苯基 | CHF2 |
68 | 2,4-二氯苯基 | CHF2 |
69 | 2,5-二氯苯基 | CHF2 |
70 | 2,6-二氯苯基 | CHF2 |
71 | 3,4-二氯苯基 | CHF2 |
72 | 3,5-二氯苯基 | CHF2 |
73 | 2,3-二氟苯基 | CHF2 |
74 | 2,4-二氟苯基 | CHF2 |
75 | 2,5-二氟苯基 | CHF2 |
76 | 2,6-二氟苯基 | CHF2 |
77 | 3,4-二氟苯基 | CHF2 |
78 | 3,5-二氟苯基 | CHF2 |
79 | 2-氯-3-氟苯基 | CHF2 |
80 | 2-氯-4-氟苯基 | CHF2 |
81 | 2-氯-5-氟苯基 | CHF2 |
82 | 2-氯-6-氟苯基 | CHF2 |
83 | 3-氯-2-氟苯基 | CHF2 |
84 | 3-氯-4-氟苯基 | CHF2 |
序号 | B | R1 |
85 | 3-氯-5-氟苯基 | CHF2 |
86 | 3-氯-6-氟苯基 | CHF2 |
87 | 4-氯-2-氟苯基 | CHF2 |
88 | 4-氯-3-氟苯基 | CHF2 |
89 | 2,3,4-三氯苯基 | CHF2 |
90 | 2,3,5-三氯苯基 | CHF2 |
91 | 2,3,6-三氯苯基 | CHF2 |
92 | 2,4,5-三氯苯基 | CHF2 |
93 | 2,4,6-三氯苯基 | CHF2 |
94 | 3,4,5-三氯苯基 | CHF2 |
95 | 2,3,4-三氟苯基 | CHF2 |
96 | 2,3,5-三氟苯基 | CHF2 |
97 | 2,3,6-三氟苯基 | CHF2 |
98 | 2,4,5-三氟苯基 | CHF2 |
99 | 2,4,6-三氟苯基 | CHF2 |
100 | 3,4,5-三氟苯基 | CHF2 |
101 | 2-氯-3,4-二氟苯基 | CHF2 |
102 | 2-氯-4,5-二氟苯基 | CHF2 |
103 | 2-氯-5,6-二氟苯基 | CHF2 |
104 | 2-氯-3,5-二氟苯基 | CHF2 |
105 | 2-氯-3,6-二氟苯基 | CHF2 |
106 | 2-氯-4,6-二氟苯基 | CHF2 |
107 | 3-氯-2,4-二氟苯基 | CHF2 |
108 | 3-氯-2,5-二氟苯基 | CHF2 |
109 | 3-氯-2,6-二氟苯基 | CHF2 |
110 | 3-氯-4,5-二氟苯基 | CHF2 |
111 | 3-氯-4,6-二氟苯基 | CHF2 |
112 | 3-氯-5,6-二氟苯基 | CHF2 |
113 | 4-氯-2,3-二氟苯基 | CHF2 |
114 | 4-氯-2,5-二氟苯基 | CHF2 |
115 | 4-氯-2,6-二氟苯基 | CHF2 |
116 | 4-氯-3,5-二氟苯基 | CHF2 |
117 | 2-氟-3,4-二氯苯基 | CHF2 |
118 | 2-氟-4,5-二氯苯基 | CHF2 |
序号 | B | R1 |
119 | 2-氟-5,6-二氯苯基 | CHF2 |
120 | 2-氟-3,5-二氯苯基 | CHF2 |
121 | 2-氟-3,6-二氯苯基 | CHF2 |
122 | 2-氟-4,6-二氯苯基 | CHF2 |
123 | 3-氟-2,4-二氯苯基 | CHF2 |
124 | 3-氟-2,5-二氯苯基 | CHF2 |
125 | 3-氟-2,6-二氯苯基 | CHF2 |
126 | 3-氟-4,5-二氯苯基 | CHF2 |
127 | 3-氟-4,6-二氯苯基 | CHF2 |
128 | 3-氟-5,6-二氯苯基 | CHF2 |
129 | 4-氟-2,3-二氯苯基 | CHF2 |
130 | 4-氟-2,5-二氯苯基 | CHF2 |
131 | 4-氟-2,6-二氯苯基 | CHF2 |
132 | 4-氟-3,5-二氯苯基 | CHF2 |
133 | 2,3-二氯苯基 | CH2F |
134 | 2,4-二氯苯基 | CH2F |
135 | 2,5-二氯苯基 | CH2F |
136 | 2,6-二氯苯基 | CH2F |
137 | 3,4-二氯苯基 | CH2F |
138 | 3,5-二氯苯基 | CH2F |
139 | 2,3-二氟苯基 | CH2F |
140 | 2,4-二氟苯基 | CH2F |
141 | 2,5-二氟苯基 | CH2F |
142 | 2,6-二氟苯基 | CH2F |
143 | 3,4-二氟苯基 | CH2F |
144 | 3,5-二氟苯基 | CH2F |
145 | 2-氯-3-氟苯基 | CH2F |
146 | 2-氯-4-氟苯基 | CH2F |
147 | 2-氯-5-氟苯基 | CH2F |
148 | 2-氯-6-氟苯基 | CH2F |
149 | 3-氯-2-氟苯基 | CH2F |
150 | 3-氯-4-氟苯基 | CH2F |
151 | 3-氯-5-氟苯基 | CH2F |
152 | 3-氯-6-氟苯基 | CH2F |
序号 | B | R1 |
153 | 4-氯-2-氟苯基 | CH2F |
154 | 4-氯-3-氟苯基 | CH2F |
155 | 2,3,4-三氯苯基 | CH2F |
156 | 2,3,5-三氯苯基 | CH2F |
157 | 2,3,6-三氯苯基 | CH2F |
158 | 2,4,5-三氯苯基 | CH2F |
159 | 2,4,6-三氯苯基 | CH2F |
160 | 3,4,5-三氯苯基 | CH2F |
161 | 2,3,4-三氟苯基 | CH2F |
162 | 2,3,5-三氟苯基 | CH2F |
163 | 2,3,6-三氟苯基 | CH2F |
164 | 2,4,5-三氟苯基 | CH2F |
165 | 2,4,6-三氟苯基 | CH2F |
166 | 3,4,5-三氟苯基 | CH2F |
167 | 2-氯-3,4-二氟苯基 | CH2F |
168 | 2-氯-4,5-二氟苯基 | CH2F |
169 | 2-氯-5,6-二氟苯基 | CH2F |
170 | 2-氯-3,5-二氟苯基 | CH2F |
171 | 2-氯-3,6-二氟苯基 | CH2F |
172 | 2-氯-4,6-二氟苯基 | CH2F |
173 | 3-氯-2,4-二氟苯基 | CH2F |
174 | 3-氯-2,5-二氟苯基 | CH2F |
175 | 3-氯-2,6-二氟苯基 | CH2F |
176 | 3-氯-4,5-二氟苯基 | CH2F |
177 | 3-氯-4,6-二氟苯基 | CH2F |
178 | 3-氯-5,6-二氟苯基 | CH2F |
179 | 4-氯-2,3-二氟苯基 | CH2F |
180 | 4-氯-2,5-二氟苯基 | CH2F |
181 | 4-氯-2,6-二氟苯基 | CH2F |
182 | 4-氯-3,5-二氟苯基 | CH2F |
183 | 2-氟-3,4-二氯苯基 | CH2F |
184 | 2-氟-4,5-二氯苯基 | CH2F |
185 | 2-氟-5,6-二氯苯基 | CH2F |
186 | 2-氟-3,5-二氯苯基 | CH2F |
序号 | B | R1 |
187 | 2-氟-3,6-二氯苯基 | CH2F |
188 | 2-氟-4,6-二氯苯基 | CH2F |
189 | 3-氟-2,4-二氯苯基 | CH2F |
190 | 3-氟-2,5-二氯苯基 | CH2F |
191 | 3-氟-2,6-二氯苯基 | CH2F |
192 | 3-氟-4,5-二氯苯基 | CH2F |
193 | 3-氟-4,6-二氯苯基 | CH2F |
194 | 3-氟-5,6-二氯苯基 | CH2F |
195 | 4-氟-2,3-二氯苯基 | CH2F |
196 | 4-氟-2,5-二氯苯基 | CH2F |
197 | 4-氟-2,6-二氯苯基 | CH2F |
198 | 4-氟-3,5-二氯苯基 | CH2F |
199 | 2,3-二氯苯基 | CHFCl |
200 | 2,4-二氯苯基 | CHFCl |
201 | 2,5-二氯苯基 | CHFCl |
202 | 2,6-二氯苯基 | CHFCl |
203 | 3,4-二氯苯基 | CHFCl |
204 | 3,5-二氯苯基 | CHFCl |
205 | 2,3-二氟苯基 | CHFCl |
206 | 2,4-二氟苯基 | CHFCl |
207 | 2,5-二氟苯基 | CHFCl |
208 | 2,6-二氟苯基 | CHFCl |
209 | 3,4-二氟苯基 | CHFCl |
210 | 3,5-二氟苯基 | CHFCl |
211 | 2-氯-3-氟苯基 | CHFCl |
212 | 2-氯-4-氟苯基 | CHFCl |
213 | 2-氯-5-氟苯基 | CHFCl |
214 | 2-氯-6-氟苯基 | CHFCl |
215 | 3-氯-2-氟苯基 | CHFCl |
216 | 3-氯-4-氟苯基 | CHFCl |
217 | 3-氯-5-氟苯基 | CHFCl |
218 | 3-氯-6-氟苯基 | CHFCl |
219 | 4-氯-2-氟苯基 | CHFCl |
220 | 4-氯-3-氟苯基 | CHFCl |
序号 | B | R1 |
221 | 2,3,4-三氯苯基 | CHFCl |
222 | 2,3,5-三氯苯基 | CHFCl |
223 | 2,3,6-三氯苯基 | CHFCl |
224 | 2,4,5-三氯苯基 | CHFCl |
225 | 2,4,6-三氯苯基 | CHFCl |
226 | 3,4,5-三氯苯基 | CHFCl |
227 | 2,3,4-三氟苯基 | CHFCl |
228 | 2,3,5-三氟苯基 | CHFCl |
229 | 2,3,6-三氟苯基 | CHFCl |
230 | 2,4,5-三氟苯基 | CHFCl |
231 | 2,4,6-三氟苯基 | CHFCl |
232 | 3,4,5-三氟苯基 | CHFCl |
233 | 2-氯-3,4-二氟苯基 | CHFCl |
234 | 2-氯-4,5-二氟苯基 | CHFCl |
235 | 2-氯-5,6-二氟苯基 | CHFCl |
236 | 2-氯-3,5-二氟苯基 | CHFCl |
237 | 2-氯-3,6-二氟苯基 | CHFCl |
238 | 2-氯-4,6-二氟苯基 | CHFCl |
239 | 3-氯-2,4-二氟苯基 | CHFCl |
240 | 3-氯-2,5-二氟苯基 | CHFCl |
241 | 3-氯-2,6-二氟苯基 | CHFCl |
242 | 3-氯-4,5-二氟苯基 | CHFCl |
243 | 3-氯-4,6-二氟苯基 | CHFCl |
244 | 3-氯-5,6-二氟苯基 | CHFCl |
245 | 4-氯-2,3-二氟苯基 | CHFCl |
246 | 4-氯-2,5-二氟苯基 | CHFCl |
247 | 4-氯-2,6-二氟苯基 | CHFCl |
248 | 4-氯-3,5-二氟苯基 | CHFCl |
249 | 2-氟-3,4-二氯苯基 | CHFCl |
250 | 2-氟-4,5-二氯苯基 | CHFCl |
251 | 2-氟-5,6-二氯苯基 | CHFCl |
252 | 2-氟-3,5-二氯苯基 | CHFCl |
253 | 2-氟-3,6-二氯苯基 | CHFCl |
254 | 2-氟-4,6-二氯苯基 | CHFCl |
序号 | B | R1 |
255 | 3-氟-2,4-二氯苯基 | CHFCl |
256 | 3-氟-2,5-二氯苯基 | CHFCl |
257 | 3-氟-2,6-二氯苯基 | CHFCl |
258 | 3-氟-4,5-二氯苯基 | CHFCl |
259 | 3-氟-4,6-二氯苯基 | CHFCl |
260 | 3-氟-5,6-二氯苯基 | CHFCl |
261 | 4-氟-2,3-二氯苯基 | CHFCl |
262 | 4-氟-2,5-二氯苯基 | CHFCl |
263 | 4-氟-2,6-二氯苯基 | CHFCl |
264 | 4-氟-3,5-二氯苯基 | CHFCl |
265 | 2,3-二氯苯基 | CF2Cl |
266 | 2,4-二氯苯基 | CF2Cl |
267 | 2,5-二氯苯基 | CF2Cl |
268 | 2,6-二氯苯基 | CF2Cl |
269 | 3,4-二氯苯基 | CF2Cl |
270 | 3,5-二氯苯基 | CF2Cl |
271 | 2,3-二氟苯基 | CF2Cl |
272 | 2,4-二氟苯基 | CF2Cl |
273 | 2,5-二氟苯基 | CF2Cl |
274 | 2,6-二氟苯基 | CF2Cl |
275 | 3,4-二氟苯基 | CF2Cl |
276 | 3,5-二氟苯基 | CF2Cl |
277 | 2-氯-3-氟苯基 | CF2Cl |
278 | 2-氯-4-氟苯基 | CF2Cl |
279 | 2-氯-5-氟苯基 | CF2Cl |
280 | 2-氯-6-氟苯基 | CF2Cl |
281 | 3-氯-2-氟苯基 | CF2Cl |
282 | 3-氯-4-氟苯基 | CF2Cl |
283 | 3-氯-5-氟苯基 | CF2Cl |
284 | 3-氯-6-氟苯基 | CF2Cl |
285 | 4-氯-2-氟苯基 | CF2Cl |
286 | 4-氯-3-氟苯基 | CF2Cl |
287 | 2,3,4-三氯苯基 | CF2Cl |
288 | 2,3,5-三氯苯基 | CF2Cl |
序号 | B | R1 |
289 | 2,3,6-三氯苯基 | CF2Cl |
290 | 2,4,5-三氯苯基 | CF2Cl |
291 | 2,4,6-三氯苯基 | CF2Cl |
292 | 3,4,5-三氯苯基 | CF2Cl |
293 | 2,3,4-三氟苯基 | CF2Cl |
294 | 2,3,5-三氟苯基 | CF2Cl |
295 | 2,3,6-三氟苯基 | CF2Cl |
296 | 2,4,5-三氟苯基 | CF2Cl |
297 | 2,4,6-三氟苯基 | CF2Cl |
298 | 3,4,5-三氟苯基 | CF2Cl |
299 | 2-氯-3,4-二氟苯基 | CF2Cl |
300 | 2-氯-4,5-二氟苯基 | CF2Cl |
301 | 2-氯-5,6-二氟苯基 | CF2Cl |
302 | 2-氯-3,5-二氟苯基 | CF2Cl |
303 | 2-氯-3,6-二氟苯基 | CF2Cl |
304 | 2-氯-4,6-二氟苯基 | CF2Cl |
305 | 3-氯-2,4-二氟苯基 | CF2Cl |
306 | 3-氯-2,5-二氟苯基 | CF2Cl |
307 | 3-氯-2,6-二氟苯基 | CF2Cl |
308 | 3-氯-4,5-二氟苯基 | CF2Cl |
309 | 3-氯-4,6-二氟苯基 | CF2Cl |
310 | 3-氯-5,6-二氟苯基 | CF2Cl |
311 | 4-氯-2,3-二氟苯基 | CF2Cl |
312 | 4-氯-2,5-二氟苯基 | CF2Cl |
313 | 4-氯-2,6-二氟苯基 | CF2Cl |
314 | 4-氯-3,5-二氟苯基 | CF2Cl |
315 | 2-氟-3,4-二氯苯基 | CF2Cl |
316 | 2-氟-4,5-二氯苯基 | CF2Cl |
317 | 2-氟-5,6-二氯苯基 | CF2Cl |
318 | 2-氟-3,5-二氯苯基 | CF2Cl |
319 | 2-氟-3,6-二氯苯基 | CF2Cl |
320 | 2-氟-4,6-二氯苯基 | CF2Cl |
321 | 3-氟-2,4-二氯苯基 | CF2Cl |
322 | 3-氟-2,5-二氯苯基 | CF2Cl |
序号 | B | R1 |
323 | 3-氟-2,6-二氯苯基 | CF2Cl |
324 | 3-氟-4,5-二氯苯基 | CF2Cl |
325 | 3-氟-4,6-二氯苯基 | CF2Cl |
326 | 3-氟-5,6-二氯苯基 | CF2Cl |
327 | 4-氟-2,3-二氯苯基 | CF2Cl |
328 | 4-氟-2,5-二氯苯基 | CF2Cl |
329 | 4-氟-2,6-二氯苯基 | CF2Cl |
330 | 4-氟-3,5-二氯苯基 | CF2Cl |
331 | 2,3-二氯苯基 | CFCl2 |
332 | 2,4-二氯苯基 | CFCl2 |
333 | 2,5-二氯苯基 | CFCl2 |
334 | 2,6-二氯苯基 | CFCl2 |
335 | 3,4-二氯苯基 | CFCl2 |
336 | 3,5-二氯苯基 | CFCl2 |
337 | 2,3-二氟苯基 | CFCl2 |
338 | 2,4-二氟苯基 | CFCl2 |
339 | 2,5-二氟苯基 | CFCl2 |
340 | 2,6-二氟苯基 | CFCl2 |
341 | 3,4-二氟苯基 | CFCl2 |
342 | 3,5-二氟苯基 | CFCl2 |
343 | 2-氯-3-氟苯基 | CFCl2 |
344 | 2-氯-4-氟苯基 | CFCl2 |
345 | 2-氯-5-氟苯基 | CFCl2 |
346 | 2-氯-6-氟苯基 | CFCl2 |
347 | 3-氯-2-氟苯基 | CFCl2 |
348 | 3-氯-4-氟苯基 | CFCl2 |
349 | 3-氯-5-氟苯基 | CFCl2 |
350 | 3-氯-6-氟苯基 | CFCl2 |
351 | 4-氯-2-氟苯基 | CFCl2 |
352 | 4-氯-3-氟苯基 | CFCl2 |
353 | 2,3,4-三氯苯基 | CFCl2 |
354 | 2,3,5-三氯苯基 | CFCl2 |
355 | 2,3,6-三氯苯基 | CFCl2 |
356 | 2,4,5-三氯苯基 | CFCl2 |
序号 | B | R1 |
357 | 2,4,6-三氯苯基 | CFCl2 |
358 | 3,4,5-三氯苯基 | CFCl2 |
359 | 2,3,4-三氟苯基 | CFCl2 |
360 | 2,3,5-三氟苯基 | CFCl2 |
361 | 2,3,6-三氟苯基 | CFCl2 |
362 | 2,4,5-三氟苯基 | CFCl2 |
363 | 2,4,6-三氟苯基 | CFCl2 |
364 | 3,4,5-三氟苯基 | CFCl2 |
365 | 2-氯-3,4-二氟苯基 | CFCl2 |
366 | 2-氯-4,5-二氟苯基 | CFCl2 |
367 | 2-氯-5,6-二氟苯基 | CFCl2 |
368 | 2-氯-3,5-二氟苯基 | CFCl2 |
369 | 2-氯-3,6-二氟苯基 | CFCl2 |
370 | 2-氯-4,6-二氟苯基 | CFCl2 |
371 | 3-氯-2,4-二氟苯基 | CFCl2 |
372 | 3-氯-2,5-二氟苯基 | CFCl2 |
373 | 3-氯-2,6-二氟苯基 | CFCl2 |
374 | 3-氯-4,5-二氟苯基 | CFCl2 |
375 | 3-氯-4,6-二氟苯基 | CFCl2 |
376 | 3-氯-5,6-二氟苯基 | CFCl2 |
377 | 4-氯-2,3-二氟苯基 | CFCl2 |
378 | 4-氯-2,5-二氟苯基 | CFCl2 |
379 | 4-氯-2,6-二氟苯基 | CFCl2 |
380 | 4-氯-3,5-二氟苯基 | CFCl2 |
381 | 2-氟-3,4-二氯苯基 | CFCl2 |
382 | 2-氟-4,5-二氯苯基 | CFCl2 |
383 | 2-氟-5,6-二氯苯基 | CFCl2 |
384 | 2-氟-3,5-二氯苯基 | CFCl2 |
385 | 2-氟-3,6-二氯苯基 | CFCl2 |
386 | 2-氟-4,6-二氯苯基 | CFCl2 |
387 | 3-氟-2,4-二氯苯基 | CFCl2 |
388 | 3-氟-2,5-二氯苯基 | CFCl2 |
389 | 3-氟-2,6-二氯苯基 | CFCl2 |
390 | 3-氟-4,5-二氯苯基 | CFCl2 |
序号 | B | R1 |
391 | 3-氟-4,6-二氯苯基 | CFCl2 |
392 | 3-氟-5,6-二氯苯基 | CFCl2 |
393 | 4-氟-2,3-二氯苯基 | CFCl2 |
394 | 4-氟-2,5-二氯苯基 | CFCl2 |
395 | 4-氟-2,6-二氯苯基 | CFCl2 |
396 | 4-氟-3,5-二氯苯基 | CFCl2 |
397 | 2,3-二氯苯基 | CH3 |
398 | 2,4-二氯苯基 | CH3 |
399 | 2,5-二氯苯基 | CH3 |
400 | 2,6-二氯苯基 | CH3 |
401 | 3,4-二氯苯基 | CH3 |
402 | 3,5-二氯苯基 | CH3 |
403 | 2,3-二氟苯基 | CH3 |
404 | 2,4-二氟苯基 | CH3 |
405 | 2,5-二氟苯基 | CH3 |
406 | 2,6-二氟苯基 | CH3 |
407 | 3,4-二氟苯基 | CH3 |
408 | 3,5-二氟苯基 | CH3 |
409 | 2-氯-3-氟苯基 | CH3 |
410 | 2-氯-4-氟苯基 | CH3 |
411 | 2-氯-5-氟苯基 | CH3 |
412 | 2-氯-6-氟苯基 | CH3 |
413 | 3-氯-2-氟苯基 | CH3 |
414 | 3-氯-4-氟苯基 | CH3 |
415 | 3-氯-5-氟苯基 | CH3 |
416 | 3-氯-6-氟苯基 | CH3 |
417 | 4-氯-2-氟苯基 | CH3 |
418 | 4-氯-3-氟苯基 | CH3 |
419 | 2,3,4-三氯苯基 | CH3 |
420 | 2,3,5-三氯苯基 | CH3 |
421 | 2,3,6-三氯苯基 | CH3 |
422 | 2,4,5-三氯苯基 | CH3 |
423 | 2,4,6-三氯苯基 | CH3 |
424 | 3,4,5-三氯苯基 | CH3 |
序号 | B | R1 |
425 | 2,3,4-三氟苯基 | CH3 |
426 | 2,3,5-三氟苯基 | CH3 |
427 | 2,3,6-三氟苯基 | CH3 |
428 | 2,4,5-三氟苯基 | CH3 |
429 | 2,4,6-三氟苯基 | CH3 |
430 | 3,4,5-三氟苯基 | CH3 |
431 | 2-氯-3,4-二氟苯基 | CH3 |
432 | 2-氯-4,5-二氟苯基 | CH3 |
433 | 2-氯-5,6-二氟苯基 | CH3 |
434 | 2-氯-3,5-二氟苯基 | CH3 |
435 | 2-氯-3,6-二氟苯基 | CH3 |
436 | 2-氯-4,6-二氟苯基 | CH3 |
437 | 3-氯-2,4-二氟苯基 | CH3 |
438 | 3-氯-2,5-二氟苯基 | CH3 |
439 | 3-氯-2,6-二氟苯基 | CH3 |
440 | 3-氯-4,5-二氟苯基 | CH3 |
441 | 3-氯-4,6-二氟苯基 | CH3 |
442 | 3-氯-5,6-二氟苯基 | CH3 |
443 | 4-氯-2,3-二氟苯基 | CH3 |
444 | 4-氯-2,5-二氟苯基 | CH3 |
445 | 4-氯-2,6-二氟苯基 | CH3 |
446 | 4-氯-3,5-二氟苯基 | CH3 |
447 | 2-氟-3,4-二氯苯基 | CH3 |
448 | 2-氟-4,5-二氯苯基 | CH3 |
449 | 2-氟-5,6-二氯苯基 | CH3 |
450 | 2-氟-3,5-二氯苯基 | CH3 |
451 | 2-氟-3,6-二氯苯基 | CH3 |
452 | 2-氟-4,6-二氯苯基 | CH3 |
453 | 3-氟-2,4-二氯苯基 | CH3 |
454 | 3-氟-2,5-二氯苯基 | CH3 |
455 | 3-氟-2,6-二氯苯基 | CH3 |
456 | 3-氟-4,5-二氯苯基 | CH3 |
457 | 3-氟-4,6-二氯苯基 | CH3 |
458 | 3-氟-5,6-二氯苯基 | CH3 |
序号 | B | R1 |
459 | 4-氟-2,3-二氯苯基 | CH3 |
460 | 4-氟-2,5-二氯苯基 | CH3 |
461 | 4-氟-2,6-二氯苯基 | CH3 |
462 | 4-氟-3,5-二氯苯基 | CH3 |
表1:
其中R2、R3为氢且R1和B对每一单独化合物在每种情况下对应于表A的一行(第1-22和67-88行除外)的通式I-A化合物。
表2:
其中R2为Cl,R3为氢且R1和B对每一单独化合物在每种情况下对应于表A的一行的通式I-A化合物。
表3:
其中R2为F,R3为氢且R1和B对每一单独化合物在每种情况下对应于表A的一行(第397-462行除外)的通式I-A化合物。
表4:
其中R2为氢,R3为甲基且R1和B对每一单独化合物在每种情况下对应于表A的一行的通式I-A化合物。
表5:
其中R2为氢,R3为乙基且R1和B对每一单独化合物在每种情况下对应于表A的一行的通式I-A化合物。
表6:
其中R2为氢且R1和B对每一单独化合物在每种情况下对应于表A的一行的通式I-B化合物。
此外还优选通式I-C和I-D化合物。
表B
序号 | B |
1 | 2,3-二氯-4-甲基苯基 |
2 | 2,3-二氯-4-甲氧基苯基 |
3 | 2,3-二氯-5-甲基苯基 |
4 | 2,3-二氯-5-甲氧基苯基 |
5 | 2,3-二氯-6-甲基苯基 |
6 | 2,3-二氯-6-甲氧基苯基 |
7 | 2,3-二氟-4-甲基苯基 |
8 | 2,3-二氟-4-甲氧基苯基 |
9 | 2,3-二氟-5-甲基苯基 |
10 | 2,3-二氟-5-甲氧基苯基 |
11 | 2,3-二氟-6-甲基苯基 |
12 | 2,3-二氟-6-甲氧基苯基 |
13 | 2,4-二氯-3-甲基苯基 |
14 | 2,4-二氯-3-甲氧基苯基 |
15 | 2,4-二氯-5-甲基苯基 |
16 | 2,4-二氯-5-甲氧基苯基 |
17 | 2,4-二氯-6-甲基苯基 |
18 | 2,4-二氯-6-甲氧基苯基 |
19 | 2,4-二氟-3-甲基苯基 |
20 | 2,4-二氟-3-甲氧基苯基 |
21 | 2,4-二氟-5-甲基苯基 |
22 | 2,4-二氟-5-甲氧基苯基 |
23 | 2,4-二氟-6-甲基苯基 |
24 | 2,4-二氟-6-甲氧基苯基 |
25 | 2,5-二氯-3-甲基苯基 |
26 | 2,5-二氯-3-甲氧基苯基 |
27 | 2,5-二氯-4-甲基苯基 |
28 | 2,5-二氯-4-甲氧基苯基 |
29 | 2,5-二氯-6-甲基苯基 |
30 | 2,5-二氯-6-甲氧基苯基 |
31 | 2,5-二氟-3-甲基苯基 |
32 | 2,5-二氟-3-甲氧基苯基 |
33 | 2,5-二氟-4-甲基苯基 |
34 | 2,5-二氟-4-甲氧基苯基 |
序号 | B |
35 | 2,5-二氟-6-甲基苯基 |
36 | 2,5-二氟-6-甲氧基苯基 |
37 | 2,6-二氯-3-甲基苯基 |
38 | 2,6-二氯-3-甲氧基苯基 |
39 | 2,6-二氯-4-甲基苯基 |
40 | 2,6-二氯-4-甲氧基苯基 |
41 | 2,6-二氟-3-甲基苯基 |
42 | 2,6-二氟-3-甲氧基苯基 |
43 | 2,6-二氟-4-甲基苯基 |
44 | 2,6-二氟-4-甲氧基苯基 |
45 | 3,4-二氯-2-甲基苯基 |
46 | 3,4-二氯-2-甲氧基苯基 |
47 | 3,4-二氯-5-甲基苯基 |
48 | 3,4-二氯-5-甲氧基苯基 |
49 | 3,4-二氯-6-甲基苯基 |
50 | 3,4-二氯-6-甲氧基苯基 |
51 | 3,4-二氟-2-甲基苯基 |
52 | 3,4-二氟-2-甲氧基苯基 |
53 | 3,4-二氟-5-甲基苯基 |
54 | 3,4-二氟-5-甲氧基苯基 |
55 | 3,4-二氟-6-甲基苯基 |
56 | 3,4-二氟-6-甲氧基苯基 |
57 | 3,5-二氯-2-甲基苯基 |
58 | 3,5-二氯-2-甲氧基苯基 |
59 | 3,5-二氯-4-甲基苯基 |
60 | 3,5-二氯-4-甲氧基苯基 |
61 | 3,5-二氟-2-甲基苯基 |
62 | 3,5-二氟-2-甲氧基苯基 |
63 | 3,5-二氟-4-甲基苯基 |
64 | 3,5-二氟-4-甲氧基苯基 |
65 | 2-氯-3-氟-4-甲基苯基 |
66 | 2-氯-3-氟-4-甲氧基苯基 |
67 | 2-氯-3-氟-5-甲基苯基 |
68 | 2-氯-3-氟-5-甲氧基苯基 |
序号 | B |
69 | 2-氯-3-氟-6-甲基苯基 |
70 | 2-氯-3-氟-6-甲氧基苯基 |
71 | 2-氯-4-氟-3-甲基苯基 |
72 | 2-氯-4-氟-3-甲氧基苯基 |
73 | 2-氯-4-氟-5-甲基苯基 |
74 | 2-氯-4-氟-5-甲氧基苯基 |
75 | 2-氯-4-氟-6-甲基苯基 |
76 | 2-氯-4-氟-6-甲氧基苯基 |
77 | 2-氯-5-氟-3-甲基苯基 |
78 | 2-氯-5-氟-3-甲氧基苯基 |
79 | 2-氯-5-氟-4-甲基苯基 |
80 | 2-氯-5-氟-4-甲氧基苯基 |
81 | 2-氯-5-氟-6-甲基苯基 |
82 | 2-氯-5-氟-6-甲氧基苯基 |
83 | 2-氯-6-氟-3-甲基苯基 |
84 | 2-氯-6-氟-3-甲氧基苯基 |
85 | 2-氯-6-氟-4-甲基苯基 |
86 | 2-氯-6-氟-4-甲氧基苯基 |
87 | 2-氯-6-氟-5-甲基苯基 |
88 | 2-氯-6-氟-5-甲氧基苯基 |
89 | 2-氟-3-氯-4-甲基苯基 |
90 | 2-氟-3-氯-4-甲氧基苯基 |
91 | 2-氟-3-氯-5-甲基苯基 |
92 | 2-氟-3-氯-5-甲氧基苯基 |
93 | 2-氟-3-氯-6-甲基苯基 |
94 | 2-氟-3-氯-6-甲氧基苯基 |
95 | 2-氟-4-氯-3-甲基苯基 |
96 | 2-氟-4-氯-3-甲氧基苯基 |
97 | 2-氟-4-氯-5-甲基苯基 |
98 | 2-氟-4-氯-5-甲氧基苯基 |
99 | 2-氟-4-氯-6-甲基苯基 |
100 | 2-氟-4-氯-6-甲氧基苯基 |
101 | 2-氟-5-氯-3-甲基苯基 |
102 | 2-氟-5-氯-3-甲氧基苯基 |
序号 | B |
103 | 2-氟-5-氯-4-甲基苯基 |
104 | 2-氟-5-氯-4-甲氧基苯基 |
105 | 2-氟-5-氯-6-甲基苯基 |
106 | 2-氟-5-氯-6-甲氧基苯基 |
107 | 3-氯-4-氟-2-甲基苯基 |
108 | 3-氯-4-氟-2-甲氧基苯基 |
109 | 3-氯-4-氟-5-甲基苯基 |
110 | 3-氯-4-氟-5-甲氧基苯基 |
111 | 3-氯-4-氟-6-甲基苯基 |
112 | 3-氯-4-氟-6-甲氧基苯基 |
113 | 3-氟-4-氯-2-甲基苯基 |
114 | 3-氟-4-氯-2-甲氧基苯基 |
115 | 3-氟-4-氯-5-甲基苯基 |
116 | 3-氟-4-氯-5-甲氧基苯基 |
117 | 3-氟-4-氯-6-甲基苯基 |
118 | 3-氟-4-氯-6-甲氧基苯基 |
119 | 3-氯-5-氟-2-甲基苯基 |
120 | 3-氯-5-氟-2-甲氧基苯基 |
121 | 3-氯-5-氟-4-甲基苯基 |
122 | 3-氯-5-氟-4-甲氧基苯基 |
123 | 3-氯-5-氟-6-甲基苯基 |
124 | 3-氯-5-氟-6-甲氧基苯基 |
表7:
其中B对每一单独化合物在每种情况下对应于表B的一行的通式I-C化合物。
表8:
其中B对每一单独化合物在每种情况下对应于表B的一行的通式I-D化合物。
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优异的活性,所述真菌尤其选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、Peronasporomycetes(同义词:卵菌纲(Oomycetes))和担子菌纲(Basidiomycetes)真菌。它们中的一些呈内吸活性并可以作为叶面杀真菌剂、土壤杀真菌剂和拌种用杀真菌剂用于作物保护中。
它们对在各种作物如小麦、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(例如土豆和其他植物上的早疫链格孢(A.solani)或细交链孢(A.alternata)),
-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(例如大麦上的大麦网斑内脐蠕孢(D.teres),小麦上的D.tritci-repentis),
-禾谷类中的禾白粉菌(Blumeria graminis)(白粉病),
-草莓、蔬菜、花卉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(例如糖用甜菜上的C.beticula),
-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、棉花和其他植物上的剌盘孢(Colletotricum)属(例如各种植物上的C.acutatum),
-玉米上的突脐蠕孢(Exserohilum)属,
-葫芦科植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
-各种植物上的镰孢霉(Fusarium)属(例如小麦上的禾谷镰刀菌(F.graminearum))和轮枝孢(Verticillium)属(例如大丽轮枝菌(V.dahliae)),
-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(例如H.graminicola),
-禾谷类上的Michrodochium nivale,
-禾谷类、香蕉和花生上的球腔菌(Mycosphaerella)属(小麦上的禾生球腔菌(M.graminicola),香蕉上的M.fijiesis),
-大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.meibomiae),
-大豆、向日葵和葡萄藤上的拟茎点霉(Phomopsis)属(葡萄藤上的葡萄拟茎点霉(P.viticola),向日葵上的P.helianthii),
-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(例如黄瓜上的P.cubenis),
-禾谷类、玉米和芦笋上的柄锈菌(Puccinia)属(小麦上的小麦锈病(P.triticina)和条锈病(P.striformis),芦笋上的芦笋锈病(P.asparagi)),
-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、糖用甜菜、蔬菜和其他植物上的丝核菌(Rhizoctonia)属(例如立枯丝核病菌(R.solani)),
-油菜籽、向日葵和其他植物上的核盘菌(Sclerotinia)属(例如核盘菌(S.sclerotiorum)),
-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Uncinulanecator),
-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)(例如苹果上的苹果黑星病(V.inaequalis))。
此外,化合物I还适于防治有害真菌以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材保护中,特别应注意下列有害真菌:子囊菌纲真菌,如线嘴壳属(Ophiostoma spp.),长喙壳属(Ceratocystis spp.),出芽短梗霉(Aureobasidium pullulans),Sclerophomaspp.,毛壳属(Chaetomium spp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,如粉孢革菌属(Coniophora spp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllumspp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔菌属(Poriaspp.),干朽菌属(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,如曲霉属(Aspergillus spp.),枝孢属(Cladosporium spp.),青霉属(Penicillium spp.),木霉属(Trichoderma spp.),链格孢属(Alternaria spp.),拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,如毛霉属(Mucor spp.),在材料保护中额外应注意下列酵母:假丝酵母属(Candidaspp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I可以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。
在例如通过撒粉、涂敷或浸泡种子的处理种子中,每100kg种子通常要求的活性化合物量为1-1000g,优选5-100g。
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。
可以将化合物l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。使用形式取决于特定的意欲目的;在每种情况下都应确保本发明化合物精细和均匀地分布。
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。
所用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,聚氧乙烯辛基苯基醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基苯基聚乙二醇醚,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、尿素以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
种子处理用配制剂可以额外包含粘合剂和/或胶凝剂以及合适的话着色剂。
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
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。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
对于种子处理,所述配制剂在稀释2-10倍后得到活性化合物在即用制剂中的浓度为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)
将10重量份本发明化合物I溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。以此方式得到活性化合物含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份本发明化合物I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。活性化合物含量为20重量%。
C)乳油(EC)
将15重量份本发明化合物I溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D)乳液(EW、EO)
将25重量份本发明化合物I溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(例如Ultraturrax)将该混合物加入30重量份水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E)悬浮液(SC、OD)
在搅拌的球磨机中,将20重量份本发明化合物I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。该配制剂中的活性化合物含量为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I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)
将75重量份本发明化合物I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%。
2.不经稀释而施用的产品
H)可撒粉粉末(DP)
将5重量份本发明化合物I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重量份本发明化合物I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I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。
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),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;它们应总是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液浓缩物、糊或可湿性粉末(可润湿粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而,还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
可以将各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性化合物中,合适的话恰在紧临使用之前(桶混合)加入。这些试剂可以1∶100-100∶1,优选1∶10-10∶1的重量比与本发明试剂混合。
在这方面而言合适的辅助剂尤其为有机改性的聚硅氧烷,例如BreakThru S醇烷氧基化物,例如AtplusAtplus MBAPlurafac LF和Lutensol ONEO/PO嵌段聚合物,例如PluronicRPE和Genapol醇乙氧基化物,例如Lutensol XP以及磺基琥珀酸二辛酯钠,例如Leophen
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、生长调节剂如调环酸钙(prohexadione-Ca)、杀真菌剂或肥料一起存在。将化合物I或包含它们的组合物与一种或多种其它活性化合物,尤其是杀真菌剂混合时,在许多情况下可以拓宽活性谱或防止抗药性的产生。在许多情况下得到了协同增效效果。
本发明化合物可以与其结合使用的下列杀真菌剂用来说明可能的组合但不限制它们:
嗜球果伞素类(Strobilurins)
-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)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、肟菌酯(trifloxystrobin)、肟醚菌胺(orysastrobin)、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯、2-(邻-((2,5-二甲基苯氧基亚甲基)苯基)-3-甲氧基丙烯酸甲酯;
羧酰胺类
-羧酰苯胺类:苯霜灵(benalaxyl)、麦锈灵(benodanil)、啶酰菌胺(boscalid)、萎锈灵(carboxin)、丙氧灭绣胺(mepronil)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、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;
-羧酸吗啉化物:烯酰吗啉(dimethomorph)、氟吗啉(flumorph);
-苯甲酰胺类:氟联苯菌(flumetover)、fluopicolide(氟吡菌胺(picobenzamid))、苯酰菌胺(zoxamide);
-其他羧酰胺:氯环丙酰胺(carpropamid)、双氯氰菌胺(diclocymet)、双炔酰菌胺(mandipropamid)、N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-甲烷磺酰基氨基-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-乙烷磺酰基氨基-3-甲基丁酰胺;
唑类
-三唑类:双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、烯菌灵(enilconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、氟硅唑(flusilazole)、喹唑菌酮(fluquinconazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、唑菌醇(triadimenol)、三唑酮(triadimefon)、戊叉唑菌(triticonazole);
-咪唑类:氰霜唑(cyazofamid)、烯菌灵(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole);
-苯并咪唑类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole);
-其他:噻唑菌胺(ethaboxam)、氯唑灵(etridiazole)、土菌消(hymexazole);含氮杂环基化合物
-吡啶类:氟啶胺(fluazinam)、啶斑肟(pyrifenox)、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶;
-嘧啶类:磺嘧菌灵(bupirimate)、环丙嘧啶(cyprodinil)、嘧菌腙(ferimzone)、异嘧菌醇(fenarimol)、嘧菌胺(mepanipyrim)、氟苯嘧啶醇(nuarimol)、二甲嘧菌胺(pyrimethanil);
-哌嗪类:嗪氨灵(triforine);
-吡咯类:氟噁菌(fludioxonil)、拌种咯(fenpiclonil);
-吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
-二羧酰亚胺类:异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
-其他:噻二唑素(acibenzolar-S-methyl)、敌菌灵(anilazine)、克菌丹(captan)、敌菌丹(captafol)、棉隆(dazomet)、哒菌清(diclomezine)、氰菌胺(fenoxanil)、灭菌丹(folpet)、苯锈啶(fenpropidin)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异噻菌酮(octhilinone)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、三环唑(tricyclazole)、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,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;
氨基甲酸盐和二硫代氨基甲酸盐
-二硫代氨基甲酸盐类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、威百亩(metam)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-氨基甲酸盐类:乙霉威(diethofencarb)、flubenthiavalicarb、异丙菌胺(iprovalicarb)、百维灵(propamocarb)、3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯、N-(1-(1-(4-氰基苯基)乙烷磺酰基)丁-2-基)氨基甲酸4-氟苯基酯;
其他杀真菌剂
-胍类:多果定(dodine)、双胍辛醋酸盐(iminoctadine)、双胍盐(guazatine);
-抗生素类:春雷素(kasugamycin)、多氧霉素(polyoxins)、链霉素(streptomycin)、井冈霉素(validamycin A);
-有机金属化合物类:三苯锡基盐;
-含硫的杂环基化合物:稻瘟灵(isoprothiolane)、二噻农(dithianon);
-有机磷化合物:克瘟散(edifenphos)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl)、亚磷酸及其盐;
-有机氯化合物:甲基托布津(thiophanate-methyl)、百菌清(chlorothalonil)、抑菌灵(dichlofluanid)、对甲抑菌灵(tolylfluanid)、磺菌胺(flusulfamide)、四氯苯酞(phthalide)、六氯苯(hexachlorobenzene)、戊菌隆(pencycuron)、五氯硝基苯(quintozene);
-硝基苯基衍生物:乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton);
-无机活性化合物:波尔多液(Bordeaux混合物)、醋酸铜、氢氧化铜、王铜、碱式硫酸铜、硫;
-其他:螺噁茂胺(spiroxamine)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、苯菌酮(metrafenone)。
合成实施例
实施例1:N-(3’-氯-4’-氟联苯-2-基)-1,3-二甲基-1H-吡唑-4-甲酰胺
在室温下将0.47g 3’-氯-4’-氟-2-氨基联苯和0.82g二(2-氧代-3-噁唑烷基)磷酰氯加入0.30g 1,3-二甲基-1H-吡唑-4-甲酸和0.43g三乙胺在30ml二氯甲烷中的溶液中。将该混合物室温搅拌12小时。然后将混合物依次用稀盐酸洗涤两次,用碳酸氢钠水溶液洗涤两次并用水洗涤一次。将有机相干燥并浓缩。粗产物通过使用环己烷/甲基叔丁基醚1∶2的硅胶柱层析提纯。以白色晶体得到0.56g熔点为177-180℃的所需产物。
实施例2:N-(3′-氯-4′-氟联苯-2-基)-3-氟甲基-1-甲基-1H-吡唑-4-甲酰胺
在室温下将0.27g 3-氟甲基-1-甲基-1H-吡唑-4-甲酰氯滴加到0.33g 3′-氯-4′-氟-2-氨基联苯和0.18g吡啶在10ml甲苯中的溶液中并将该混合物室温搅拌16小时。加入10ml四氢呋喃和30ml甲基叔丁基醚,并将有机相依次用浓度为2%的盐酸洗涤,用浓度为2%的氢氧化钠水溶液洗涤两次,然后用稀氯化钠水溶液洗涤。将有机相干燥并减压浓缩。粗产物用10ml二异丙基醚研制并将剩余的固体吸滤和干燥。以白色粉末得到0.46g熔点为133-134℃的所需产物。
实施例3:N-(3′,4′-二氯联苯-2-基)甲基-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺
在冰冷却下将0.25g N-(3′,4′-二氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺和0.09g甲基碘加入0.02g氢化钠在5ml N,N-二甲基甲酰胺中的溶液中。将该混合物室温搅拌12小时,然后加入浓度为1%的盐酸和甲基叔丁基醚。将有机相依次用水和饱和氯化钠水溶液洗涤,并减压浓缩溶液。粗产物通过使用环己烷/乙酸乙酯1∶1的硅胶柱层析提纯。以乳状油得到0.15g所需产物。
实施例4:N-(3′,4′-二氯联苯-2-基)-3-(二氯一氟甲基)-1-甲基-1H-吡唑-4-甲酰胺
a)N-(3’,4-二氯联苯-2-基)-3-(二氯一氟甲基)-1-甲基-1H-吡唑-4-甲酰胺
将0.37g来自4b的油滴加到0.36g 3′,4′-二氯-2-氨基联苯和0.18g吡啶在10ml甲苯中的溶液中并室温搅拌反应混合物16小时。然后加入10ml四氢呋喃和30ml甲基叔丁基醚。将有机相依次用浓度为2%的盐酸洗涤,用碳酸氢钠水溶液洗涤两次并用稀氯化钠水溶液洗涤。将有机相干燥并减压浓缩。粗产物用10ml二异丙基醚研制并将剩余的固体吸滤和干燥。以白色粉末得到0.48g熔点为145-146℃的所需产物。
b)3-二氯一氟甲基-1-甲基-4-吡唑甲酰氯
将5.3g 3-二氯一氟甲基-1-甲基-4-吡唑甲酸和27.8g亚硫酰氯的混合物在回流下加热2小时。然后使用旋转蒸发器浓缩反应混合物并与50ml甲苯一起蒸馏两次。分离的油直接进行进一步反应而无需进一步提纯。
c)3-二氯一氟甲基-1-甲基-4-吡唑甲酸
在室温下将10.20g 3-二氯一氟甲基-1-甲基-4-甲酸乙酯在20ml四氢呋喃中的溶液滴加到5.13g三甲基硅烷醇钾和100ml四氢呋喃的混合物中,并将该混合物在室温下搅拌12小时。吸滤沉淀,用四氢呋喃洗涤并在减压下干燥。将所得固体溶于200ml冰水中并使用浓度为10%的盐酸将该溶液调节至pH 2。将沉淀用甲基叔丁基醚萃取两次并将合并的有机相用饱和氯化钠水溶液洗涤。在干燥并减压蒸发溶剂之后,以白色固体分离出5.50g熔点为167-169℃的上述酸。
使用这里所给程序制备下表9所列的其中W=O的通式I化合物。
应用实施例
本发明化合物I的杀真菌作用由下列试验证实:
使用溶剂/乳化剂体积比为99/1的丙酮和/或二甲亚砜与乳化剂EL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)的混合物将各活性化合物配成包含25mg活性化合物并配成10ml的储香溶液。然后将该溶液用水配成100ml。将该储备溶液用所述溶剂/乳化剂/水混合物稀释至所需活性化合物浓度。
对由灰葡萄孢引起的柿子椒叶子上的灰霉病的活性,保护性施用
将栽培品种为“Neusiedler Ideal Elite”的柿子椒秧苗在充分发育出2-3片叶后用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将已处理植物用在浓度为2%的生物麦芽水溶液中含有1.7×106个孢子/ml的灰葡萄孢的孢子悬浮液接种。然后将试验植物置于22-24℃和高大气湿度的黑暗气候调节室中。5天后可以百分数肉眼测定叶子上的真菌侵染程度。
在该试验中,用250mg/l表9的化合物9.1、9.3、9.12、9.13、9.14、9.17、9.18、9.19、9.20、9.30、9.32、9.33、9.35、9.36、9.37、9.38、9.39、9.40、9.42、9.43、9.44和9.45处理的植物显示出至多20%的侵染,而未处理植物90%被侵染。
对由颖枯球腔菌(Leptosphaeria nodorum)引起的小麦黄斑病的活性
将栽培品种为“Kanzler”的小麦植物盆用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将各盆用颖枯球腔菌(同义词Stagonosporoa nodorum,颖枯壳针孢(Septoroia nodorum))的含水孢子悬浮液接种。然后将植物置于20℃和最大大气湿度的室中。8天后未处理但侵染的对照植物上的黄斑病发展到可以肉眼测定侵染百分数的程度。
在该试验中,用250mg/l表9的化合物9.1、9.2、9.13和9.27处理的植物显示出至多20%的侵染,而未处理植物60%被侵染。
对小麦隐匿柄锈菌(Puccinia recondita)引起的小麦叶锈病的治疗活性
将栽培品种为“Kanzler”的盆栽小麦秧苗的叶子用小麦叶锈病菌(小麦隐匿柄锈菌)的孢子悬浮液接种。然后将盆在20-22℃和高大气湿度(90-95%)的室中放置24小时。在此期间孢子萌发并且芽管穿透到叶组织中。第二天将侵染的植物用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。该悬浮液或乳液如上所述制备。在喷雾涂层干燥之后,将试验植物在温度为20-22℃且相对大气湿度为65-70%的温室中栽培7天。然后测定叶子上的锈病真菌发展程度。
在该试验中,用250mg/l表9的化合物9.1、9.3、9.4、9.5、9.6、9.7、9.8、9.9、9.10、9.11、9.12、9.13、9.14、9.15、9.17、9.18、9.19、9.20、9.21、9.25、9.26、9.27、9.28、9.29、9.33、9.34、9.35、9.36、9.37、9.38、9.39、9.40、9.42、9.43、9.44和9.45处理的植物显示出至多20%的侵染,而未处理植物90%被侵染。
对比试验-对由灰葡萄孢引起的柿子椒叶子上的灰霉病的活性,保护性施用
将来自EP-A 0 589 301表1的化合物47与表9的本发明化合物9.17和9.20进行比较。
将栽培品种为“Neusiedler Ideal Elite”的柿子椒秧苗在充分发育出2-3片叶后用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将已处理植物用在浓度为2%的生物麦芽水溶液中含有1.7×106个孢子/ml的灰葡萄孢的孢子悬浮液接种。然后将试验植物置于22-24℃和高大气湿度的黑暗气候调节室中。5天后可以百分数肉眼测定叶子上的真菌侵染程度。
表10
由表10的杀真菌数据可见,本发明化合物9.17和9.20与现有技术的结构最接近的化合物相比明显具有改进的杀真菌作用。
Claims (9)
2.根据权利要求1的式I的吡唑甲酰苯胺,其中各变量如下所定义:
X2为氟或氯;
R1为氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基或三氟甲基;
R2为氢、氟或氯;
R3为氢;
W为氧。
3.根据权利要求1或2的式I的吡唑甲酰苯胺,其中各变量如下所定义:
X2为氟或氯,
R1为氟甲基、二氟甲基、氯氟甲基、一氯二氟甲基、二氯一氟甲基或三氟甲基;
R2为氢或氯;
R3为氢;
W为氧。
4.根据权利要求1的式I的吡唑甲酰苯胺,选自:
N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺,
N-(2′,4′,5′-三氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺,
N-(2′,3′,4′-三氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺,
N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-二氟甲基-1H-吡唑-4-甲酰胺,
N-(2′,4′,5′-三氟联苯-2-基)-1-甲基-3-二氟甲基-1H-吡唑-4-甲酰胺,
N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-一氯二氟甲基-1H-吡唑-4-甲酰胺,
N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-氯氟甲基-1H-吡唑-4-甲酰胺,
N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-氟甲基-1H-吡唑-4-甲酰胺,
N-(2′,3′,4′-三氟联苯-2-基)-1-甲基-3-氟甲基-1H-吡唑-4-甲酰胺,
N-(2′,4′,5′-三氟联苯-2-基)-1-甲基-3-氟甲基-1H-吡唑-4-甲酰胺。
5.一种防治有害真菌的组合物,该组合物包含杀真菌量的根据权利要求1-4中任一项的式I化合物和至少一种惰性添加剂。
6.一种防治植物病原性有害真菌的方法,包括用杀真菌有效量的根据权利要求1-4中任一项的式I化合物处理有害真菌、其栖息地和/或需要防止真菌侵袭的材料、植物、土壤或种子。
7.根据权利要求1-4中任一项的化合物I在防治植物病原性有害真菌中的用途。
8.一种处理种子的方法,其中用1-1000g/kg种子的量的根据权利要求1-4中任一项的式I化合物进行所述处理。
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DE10204390A1 (de) | 2002-02-04 | 2003-08-14 | Bayer Cropscience Ag | Disubstituierte Thiazolylcarboxanilide |
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BRPI0512121A (pt) * | 2004-06-18 | 2008-02-06 | Basf Ag | composto, processo para combater fungos nocivos, agente fungicida, e, uso de compostos |
PE20060096A1 (es) * | 2004-06-18 | 2006-03-16 | Basf Ag | (orto-fenil)-anilidas de acido 1-metil-3-difluorometil-pirazol-4-carboxilico como agentes fungicidas |
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