CN1216437A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
- Publication number
- CN1216437A CN1216437A CN97194011A CN97194011A CN1216437A CN 1216437 A CN1216437 A CN 1216437A CN 97194011 A CN97194011 A CN 97194011A CN 97194011 A CN97194011 A CN 97194011A CN 1216437 A CN1216437 A CN 1216437A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- formula
- chemical compounds
- iii
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 7
- -1 C2-C6-alkenyl halide Chemical class 0.000 claims abstract description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims abstract description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005864 Sulphur Substances 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 61
- 229940084434 fungoid Drugs 0.000 claims description 10
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 8
- 230000002195 synergetic effect Effects 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 206010017533 Fungal infection Diseases 0.000 claims description 5
- 208000031888 Mycoses Diseases 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- TYRDEZUMAVRTEO-UHFFFAOYSA-N pyrimidin-5-ylmethanol Chemical compound OCC1=CN=CN=C1 TYRDEZUMAVRTEO-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 18
- 230000000694 effects Effects 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 241000209140 Triticum Species 0.000 description 7
- 241000233866 Fungi Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000009754 Vitis X bourquina Nutrition 0.000 description 5
- 235000012333 Vitis X labruscana Nutrition 0.000 description 5
- 240000006365 Vitis vinifera Species 0.000 description 5
- 235000014787 Vitis vinifera Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 241001123569 Puccinia recondita Species 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 244000000004 fungal plant pathogen Species 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- 241000510928 Erysiphe necator Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241001361634 Rhizoctonia Species 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000004763 spore germination Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical compound OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical compound CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241001478240 Coccus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001344131 Magnaporthe grisea Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
- 241000736122 Parastagonospora nodorum Species 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000899394 Pseudocercospora Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001515790 Rhynchosporium secalis Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241001251949 Xanthium sibiricum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000001720 action spectrum Methods 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 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 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及杀真菌混合物,它包含增效活性量的a)式Ⅰ的肟醚,其中取代基具有下列含意:X是氧或氨基(NH);Y是CH或N;Z是氧、硫、氨基(NH)或C1－C4－烷基氨基(N－C1－C4－烷基);R’是C1－C6－烷基、C1－C6－卤代烷基、C3－C6－链烯基、C2－C6－卤代链烯基、C3－C6－炔基、C3－C6－卤代炔基、C3－C6－环烷基甲基或是苄基,该苄基可以是部分或全部卤代的和/或可以有一至三个下列基团连于其上:氰基、C1－C4－烷基、C1－C4－卤代烷基、C1－C4－烷氧基、C1－C4－卤代烷氧基和C1－C4－烷硫基;和/或b)式Ⅱ的氨基甲酸酯,其中T是CH或N,n是0、1或2,且R是卤素、C1－C4－烷基或C1－C4－卤代烷基,当n是2时基团R可以不同,和c)式Ⅲ的(±)－(2－氯苯基)(4－氯苯基)(嘧啶－5－基)甲醇。
Description
本发明涉及杀真菌混合物，它包含增效活性量的
a)式Ⅱ的肟醚
其中取代基具有下列含意：
X是氧或氨基(NH)；
Y是CH或N；
Z是氧、硫、氨基(NH)或C1-C4-烷基氨基(N-C1-C4-烷基)；
R’是C1-C6-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C2-C6-卤代链烯基、C3-C6-炔基、C3-C6-卤代炔基、C3-C6-环烷基甲基，或是苄基，该苄基可以是部分或全部卤代的和/或可以有一至三个下列基团连于其上：氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基和C1-C4-烷硫基；
和/或
b)式Ⅱ的氨基甲酸酯
其中T是CH或N,n是0、1或2，且R是卤素、C1-C4-烷基或C1-C4-卤代烷基，当n是2时基团R可以不同，和
c)式Ⅲ的(±)-(2-氯苯基)(4-氯苯基)(嘧啶-5-基)甲醇
而且，本发明涉及用化合物Ⅰ和Ⅱ的混合物防治有害真菌的方法，以及涉及化合物Ⅰ和化合物Ⅱ制备这种混合物的应用。
式Ⅰ化合物、其制备和其对有害真菌的作用已公开于文献中(WO-A95/21,153、WO95/21154、DE-A19528651.0)。
式Ⅱ化合物、其制备和其对有害真菌的作用业已描述于WO-A96/01,256和WO-A96/01,258中。
式Ⅲ化合物(GB-A 1,218,623；通用名：氯苯嘧啶醇)、其制备和其对有害真菌的作用也已公开。
本发明的目的是提供对有害真菌具有改进作用且降低施用活性成分总量的混合物(增效混合物)，目的在于使这些已知化合物施用量降低和改进其作用谱。
因此，我们发现此目的通过开头定义的混合物实现。而且，我们发现，通过同时一起或分别施用化合物Ⅰ和/或Ⅱ和化合物Ⅲ，或依次施用化合物Ⅰ和/或Ⅱ和化合物Ⅲ，可以比使用单独的化合物更好地防治有害真菌。
本发明包括化合物Ⅰ和Ⅲ或者Ⅱ和Ⅲ的二元混合物，也包括化合物Ⅰ、Ⅱ和Ⅲ的混合物。
特别是，通式Ⅰ代表的肟醚中，优选其中X是氧且Y是CH或者其中X是氨基且Y是N。
此外，优选的是那些其中Z是氧的化合物Ⅰ。
同样，优选的是那些其中R’是烷基或苄基的化合物Ⅰ。
对于其在本发明的增效混合物中应用而言，特别优选的化合物Ⅰ是汇集于下表中的那些：
表1．
式ⅠA化合物，其中对于每一化合物，ZR’相应于表A中的一行
表2．
式ⅠB化合物，其中对于每一化合物而言，ZR’相应于表A中的一行
表A：
| 序号 | ZR＇ |
| Ⅰ.1 | O-CH2CH2CH3 |
| Ⅰ.2 | O-CH(CH3)2 |
| Ⅰ.3 | O-CH2CH2CH2CH3 |
| Ⅰ.4 | O-CH(CH3)CH2CH3 |
| Ⅰ.5 | O-CH2CH(CH3)2 |
| Ⅰ.6 | O-C(CH3)3 |
| Ⅰ.7 | S-C(CH3)3 |
| Ⅰ.8 | O-CH(CH3)CH2CH2CH3 |
| Ⅰ.9 | O-CH2C(CH3)3 |
| Ⅰ.10 | O-CH2C(Cl)=CCl2 |
| Ⅰ.11 | O-CH2CH=CH-Cl(trans) |
| Ⅰ.12 | O-CH2C(CH3)=CH2 |
| Ⅰ.13 | O-CH2-(cyclopropyl) |
| Ⅰ.14 | O-CH2-C6H5 |
| Ⅰ.15 | O-CH2-[4-F-C6H4] |
| Ⅰ.16 | O-CH2CH3 |
| Ⅰ.17 | O-CH(CH2CH3)2 |
由于存在C=Y双键，式Ⅰ化合物可以存在E或Z构形(相对于羧酸官能团)。因此，在每一种情况下，它们可以以纯E或Z异构体或者以E/Z异构体混合物用于本发明混合物中。优选使用E/Z异构体混合物或E异构体，特别优选的是化合物Ⅰ的E异构体。
化合物Ⅰ的侧链上的肟醚基团的C=N双键在每一种情况下可以纯E或Z异构体或者E/Z异构体混合物形式存在。化合物Ⅰ可以以其异构体混合物或纯异构体使用于本发明混合物中。对于其使用而言，特别优选的化合物Ⅰ是那些其中在侧链上的未端肟醚基是顺式构形(OCH3基团相对于ZR’)的化合物Ⅰ。
由于它们的基本特性，化合物Ⅰ、Ⅱ和Ⅲ能够与无机或有机酸或与金属离子形成加成物或盐。
特别地，式Ⅱ代表的氨基甲酸酯中，优选其中取代基的组合相应于下表中的一行：
表3：
| 序号 | T | Rn |
| Ⅱ.1 | N | 2-F |
| Ⅱ.2 | N | 3-F |
| Ⅱ.3 | N | 4-F |
| Ⅱ.4 | N | 2-Cl |
| Ⅱ.5 | N | 3-Cl |
| Ⅱ.6 | N | 4-Cl |
| Ⅱ.7 | N | 2-Br |
| 序号 | T | Rn |
| Ⅱ.8 | N | 3-Br |
| Ⅱ.9 | N | 4-Br |
| Ⅱ.10 | N | 2-CH3 |
| Ⅱ.11 | N | 3-CH3 |
| Ⅱ.12 | N | 4-CH3 |
| Ⅱ.13 | N | 2-CH2CH3 |
| Ⅱ.14 | N | 3-CH2CH3 |
| Ⅱ.15 | N | 4-CH2CH3 |
| Ⅱ.16 | N | 2-CH(CH3)2 |
| Ⅱ.17 | N | 3-CH(CH3)2 |
| Ⅱ.18 | N | 4-CH(CH3)2 |
| Ⅱ.19 | N | 2-CF3 |
| Ⅱ.20 | N | 3-CF3 |
| Ⅱ.21 | N | 4-CF3 |
| Ⅱ.22 | N | 2,4-F2 |
| Ⅱ.23 | N | 2,4-Cl2 |
| Ⅱ.24 | N | 3,4-C12 |
| Ⅱ.25 | N | 2-C1,4-CH3 |
| Ⅱ.26 | N | 3-C1,4-CH3 |
| Ⅱ.27 | CH | 2-F |
| Ⅱ.28 | CH | 3-F |
| Ⅱ.29 | CH | 4-F |
| Ⅱ.30 | CH | 2-Cl |
| Ⅱ.31 | CH | 3-Cl |
| Ⅱ.32 | CH | 4-C1 |
| Ⅱ.33 | CH | 2-Br |
| Ⅱ.34 | CH | 3-Br |
| Ⅱ.35 | CH | 4-Br |
| Ⅱ.36 | CH | 2-CH3 |
| Ⅱ.37 | CH | 3-CH3 |
| Ⅱ.38 | CH | 4-CH3 |
| Ⅱ.39 | CH | 2-CH2CH3 |
| Ⅱ.40 | CH | 3-CH2CH3 |
| Ⅱ.4l | CH | 4-CH2CH3 |
| Ⅱ.42 | CH | 2-CH(CH3)2 |
| Ⅱ.43 | CH | 3-CH(CH3)2 |
| Ⅱ.44 | CH | 4-CH(CH3)2 |
| Ⅱ.45 | CH | 2-CF3 |
| Ⅱ.46 | CH | 3-CF3 |
| 序号 | T | Rn |
| Ⅱ.47 | CH | 4-CF3 |
| Ⅱ.48 | CH | 2,4-F2 |
| Ⅱ.49 | CH | 2,4-C12 |
| Ⅱ.50 | CH | 3,4-C12 |
| Ⅱ.51 | CH | 2-C1,4-CH3 |
| Ⅱ.52 | CH | 3-Cl,4-CH3 |
化合物Ⅱ.12、Ⅱ.23、Ⅱ.32和Ⅱ.38是特别优选的。
无机酸的实例是氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸，硫酸、磷酸和硝酸。
适合的有机酸是(例如)甲酸、碳酸和链烷酸如乙酸、三氟乙酸、三氯乙酸和丙酸，以及乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有1至20个碳原子的直链或支链烷基基团的磺酸)、芳基磺酸或芳基二磺酸(芳族基团如苯基和萘基，它们具有一或二个连于其上的磺基基团)、烷基膦酸(具有1至20个碳原子的直链或支链烷基基团的膦酸)、芳基膦酸或芳基二膦酸(芳族基团如苯基和萘基，它们具有一或二个连于其上的膦酸残基)，对于烷基或芳基基团，也可能有另外的取代基连于其上，例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
适合的金属离子(特别)是第二主族元素、特别是钙和镁，第三和第四主族元素、特别是铝、锡和铅，和第一至八副族元素、特别是铬、锰、铁、钴、镍、铜、锌及其它的离子。特别优选的是第四周期各副组元素的金属离子。这些金属可以以各种它们可以出现的价位存在。
当制备混合物时，优选的是采用纯的活性成分Ⅰ、Ⅱ和Ⅲ，且如果需要的话，它们可以与其它的杀有害真菌或其它杀害虫如昆虫、蜱螨或线虫的活性成分，或是与除草的或生长调节的活性成分或化肥混合。
化合物Ⅰ和/或Ⅱ和Ⅲ的混合物，或同时一起或分别使用的化合物Ⅰ和/或Ⅱ和Ⅲ，对广谱的植物病原真菌，特别是对子囊菌纲、半知菌纲、担子菌纲和藻状菌纲有突出的作用。它们中的一些有内吸作用，因此可以用作叶面和土壤作用的杀真菌剂。
它们在防治各种作物如棉花、蔬菜(例如黄瓜、豆类和胡瓜类)、大麦、禾草、燕麦、咖啡、玉米、水果、稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和各种种子上的许多植物病原真菌方面特别重要。
它们特别适合于防治下列植物病原真菌：禾谷类上的禾白粉菌(Erysiphe graminia)，胡瓜上的二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)，苹果上的苹果白粉病柄球菌(Podosphaera leucotricha)，葡萄上的葡萄白粉病钩丝壳霉(Uncinulanecator)，禾谷类上的柄锈菌(Puccinia)，棉花、稻和草坪上的丝核菌(Rhizoctonia)，禾谷类和甘蔗上的黑粉菌(Ustilago)，苹果上的苹果黑星菌(Venturia inaequalis)，禾谷类上的长蠕孢菌(Helminthosporium)，小麦上的黑麦喙孢(Rhynchosporium secalis)、枯病菌(Septoria nodorum)，草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botrytis cinera)，花生上的花生尾孢菌(Cercospora arachidicola)，小麦和大麦上的眼斑病菌(Pseudocercospora herpotophthora)，稻上的稻梨孢(Pyricularia oryzae)，马铃薯和蕃茄上的蔓延疫霉(Phytophthora infestans)，葡萄上的葡萄生单轴霉(Plasmoparaviticola)，蔬菜和水果上的链格孢菌(Alternaria)，以及镰刀菌(Fusarium)和轮枝孢菌(Verticillium)。
此外，它们可以用在材料的保护上(例如，木材的保护)，例如防治宛氏拟青霉(Paecilomhces variotii)。
化合物Ⅰ和/或Ⅱ和Ⅲ可以同时一起或分别或依次施用，在分别施用时，施用顺序通常不影响防治措施的效果。
化合物Ⅰ和/或Ⅱ和Ⅲ通常以10∶1至0.1∶1、优选5∶1至0.2∶1、特别是3∶1至0.3∶1的重量比使用。
依据所需的效果的性质的不同，本发明混合物的使用量通常为0.01至3千克/公顷，优选0.01至1.5千克/公顷，特别是0.01至0.5千克/公顷。
在化合物Ⅰ和/或Ⅱ的情况下，施用量一般是0.005至0.5千克/公顷，优选是0.005至0.5千克/公顷，特别是0.005至0.3千克/公顷。
相应地，在化合物Ⅲ的情况下，施用量一般是0.005至0.5千克/公顷，优选0.01至0.5千克/公顷，特别是0.01至0.3千克/公顷。
处理种子时，混合物的施用量通常是0.001至10克/千克种子，优选0.01至10克/千克种子，特别是0.01至8克/千克。
如果意欲防治的是植物病原真菌，则通过向种子、植物或播种前或播种后植物出芽前或后的土壤喷雾或喷粉，分别或一起施用化合物Ⅰ和/或Ⅱ和化合物Ⅲ或者化合物Ⅰ和/或Ⅱ与Ⅲ的混合物。
本发明的增效混合物或化合物Ⅰ和/或Ⅱ或Ⅲ，可以加工成(例如)可直接喷雾溶液、粉末和悬浮液形式，或高浓度水悬剂、油悬剂或其它悬浮剂、分散液、乳液、油分散液、膏剂、粉剂、用于撒施的材料或颗粒剂，并可通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用方式取决于使用的目的；在每一种情况下，应确保本发明混合物的分散尽可能的细微和均匀。
制剂以其本身已知的方式来生产，例如，添加溶剂和/或载体。惰性添加剂如乳化剂或分散剂通常用来与制剂混合。
适合的表面活性剂是芳族磺酸例如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐，以及脂肪酸、烷基磺酸和烷基芳基磺酸、烷基硫酸、月桂基醚硫酸和脂肪醇硫酸的碱金属盐、碱土金属盐和铵盐，以及硫酸化的十六-、十七-和十八烷醇或脂肪醇二醇醚的盐，磺化萘和其衍生物与甲醛的缩合产物，萘或萘磺酸与苯酚和甲醛的缩合产物，聚氧乙烯辛基酚醚，乙氧基化的异辛基-、辛基-或壬基酚，烷基苯酚或三丁基苯基的聚二醇醚，烷基芳基聚醚醇，异十三烷醇，脂肪醇/环氧乙烷缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯，月桂醇聚二醇醚乙酸酯，失水山梨醇酯，木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施材料和喷粉剂可以通过将化合物Ⅰ和/或Ⅱ或Ⅲ或者化合物Ⅰ和/或Ⅱ和Ⅲ的混合物与固体载体混合或一起研磨而制备。
颗粒剂(例如，涂敷、浸渍或均质颗粒剂)通常是通过将一种或多种活性化合物结合到固体载体上而制备的。
可以使用的填料和固体载体的实倒是矿石土如硅胶、二氧化硅、硅胶类、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁，研碎的合成材料，和化肥如硫酸铵、磷酸铵、硝酸铵、尿素，以及植物产品如面粉、树皮粉、木粉和坚果壳粉、纤维素粉，或者其它固体载体。
制剂中通常含有0.1至95％(重量)、优选0.5至90％(重量)的化合物Ⅰ和/或Ⅱ或Ⅲ之一、或化合物Ⅰ和/或Ⅱ和Ⅲ的混合物。采用的活性成分的纯度为90％至100％，优选95％至100％(根据NMR或HPLC谱)。
化合物Ⅰ和/或Ⅱ和Ⅲ或混合物或相应的制剂，是通过使用杀真菌活性量的混合物、或(在分别施用的情况下)使用杀真菌活性量的化合物Ⅰ和/或Ⅱ和Ⅲ，处理真菌或处理意欲防除有害真菌的植物、种子、土壤、区域、材料或空间来施用的。使用可以在有害真菌侵染前或后进行。
这些化合物与混合物的杀真菌活性用下列实验来说明：
活性成分分别或一起加工成于下列混合物中的浓度为10％的乳剂：70％(重量)的环己酮、20％(重量)的NekanilLN(LutensolAP6，基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)和10％(重量)的EmulphorEL(EmulanEL，基于乙氧基化脂肪醇的乳化剂)。并用水稀释至所需浓度。
通过确定感病的叶面积百分率进行评价，并将这些百分率值转化成效力。活性成分混合物的预期效力是用Colby公式来计算[R.S.Colby，《杂草[Weeds]》15,20-22(1967)]，并与实测效力作比较。
Colby公式：
E=x+y-xy/100
E以浓度a与b使用活性成分A与B的混合物时的预期效力，以相对于未处理对照的％表示
x以浓度a使用活性成分A时的效力，以相对于未处理对照的％表示
y以浓度b使用活性成分B时的效力，以相对于未处理对照的％表示。
效力(W)使用Abbot公式计算
W=(1-α)100/β
α处理植物的真菌感染％
β是未处理植物的真菌感染％。
效力为0指感染程度与未处理对照的相同；效力为100指处理的植物未感染。
实施例1-7对小麦叶锈病(Puccinia recondita)的治疗作用
种植栽培品种为“Frühgold”的盆栽小麦秧的叶片用叶锈病菌(Puccinia recondita)孢子喷粉。之后将盆在20至22℃下的高空气温度(90-95％)培养室中放置24小时。在此期间，孢子萌发，萌发管穿透入叶片组织。第二天，将感病的植株用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。在喷雾液层变干后，将试验植株在20-22℃和65-70％相对湿度下的温室中放置7天。之后确定叶片上的真菌发病程度。
将目测的感染叶片面积的百分率以未处理对照作较正，转化成效力％。效力为0指感染的程度与未处理对照中的相同，效力为100％是0％感染。用Colby公式(Colby S.R.“除草剂组合的计算增效和拮抗响应(Calculating synergistic and antagonistic responses of herbicidecombinations)”《杂草》15,p20-22,1967)确定活性化合物组合的预期效力，并与实测效力相比较。
表4
| 实施例 | 活性化合物 | 喷雾液中活性化合物的浓度(ppm) | 相对于未处理对照的效力％ |
| 1v | 对照(未处理) | (100％感染) | 0 |
| 2v | A=Tab.1A,NO.2 | 6.33.1 | 300 |
| 3v | B=Tab.lA,No.4 | 3.1 | 10 |
| 4v | Ⅲ=氯苯嘧啶醇 | 6.33.1 | 700 |
表5：
*用Colby公式计算实施例8-15 对小麦叶锈病(Puccinia recondita)的作用
| 实施例 | 喷雾液中的活性化合物浓度(ppm) | 实测效力 | 计算效力*) |
| 5 | 6.3A+3.1 Ⅲ | 90 | 79 |
| 6 | 3.1A+3.1 Ⅲ | 40 | 0 |
| 7 | 3.1B+3.1 Ⅲ | 50 | 10 |
种植栽培品种为“Frühgold”的盆栽小麦秧的叶片用叶锈病菌(Puccinia recondita)孢子喷粉。之后将盆在20至22℃下的高空气湿度(90-95％)培养室中放置24小时。在此期间，孢子萌发，萌发管穿透入叶片组织。第二天，将感病的植株用由10％活性成分、63％环己酮和27％乳化剂的母液制备出的活性化合物的含水制剂喷雾直到雾滴向下滴流点。在喷雾液层变干后，将试验植株在20-22℃和65-70％相对湿度下的温室中放置7天。之后确定叶片上的真菌发病程度。
将目测的感染叶片面积的百分率以未处理对照作较正，转化成效力％。效力为0指感染的程度与未处理对照中的相中，效力为100％是0％感染。用Colby公式(Colby S.R.“除草剂组合的计算增效和拮抗响应”《杂草》15,p20-22,1967)确定活性化合物组合的预期效力，并与实测效力相比较。
表6：
| 实施例 | 活性化合物 | 喷雾液中活性化合物浓度(ppm) | 效力％ |
| 8v | 对照(未处理) | (90％感染) | 0 |
| 9v | 表3的No.Ⅱ.32化合物=C | 3.11.6 | 0 |
| 10v | 表3的No.Ⅱ.38化合物=D | 3.11.6 | 700 |
| 11v | Ⅲ=氯苯嘧啶醇 | 12.56.3 | 200 |
表7：
| 实施例 | 喷雾液中的活性化合物浓度(ppm) | 实测效力 | 计算效力*) |
| 12 | 3.1C+12.5 Ⅲ | 40 | 20 |
| 13 | 1.6C+6.3 Ⅲ | 25 | 0 |
| 14 | 3.1D+12.5 Ⅲ | 90 | 76 |
| 15 | 1.6D+6.3 Ⅲ | 30 | 0 |
Claims (8)
1．杀真菌混合物，它包含增效活性量的
a)式Ⅰ的肟醚
其中取代基具有下列含意：
X是氧或氨基(NH)；
Y是CH或N；
Z是氧、硫、氨基(NH)或C1-C4-烷基氨基(N-C1-C4-烷基)；
R’是C1-C6-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C2-C6-卤代链烯基、C3-C6-炔基、C3-C6-卤代炔基、C3-C6-环烷基甲基或是苄基，该苄基可以是部分或全部卤代的和/或可以有一至三个下列基团连于其上：氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基和C1-C4-烷硫基；
和/或
b)式Ⅱ的氨基甲酸酯
其中T是CH或N,n是0、1或2，且R是卤素、C1-C4-烷基或C1-C4-卤代烷基，当n是2时基团R可以不同，和
c)式Ⅲ的(±)-(2-氯苯基)(4-氯苯基)(嘧啶-5-基)甲醇
2．根据权利要求1的杀真菌混合物，其中化合物Ⅰ和/或Ⅱ与化合物Ⅲ的重量比是10∶1至0.1∶1。
3．防治有害真菌的方法，它包括用权利要求1中所述的式Ⅰ和/或Ⅱ化合物以及权利要求1中所述的式Ⅲ化合物处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
4．根据权利要求3的方法，其中权利要求1中所述的化合物Ⅰ和/或Ⅱ和权利要求1中所述的化合物Ⅲ同时一起或者分别或者依次施用。
5．根据权利要求3的方法，其中权利要求1中所述的化合物Ⅰ和/或Ⅱ以0.005至0.5千克/公顷的量处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
6．根据权利要求3的方法，其中权利要求1中所述的化合物Ⅲ以0.05至0.5千克/公顷的量处理有害真菌、它们的环境或者意欲不受真菌侵染的植物、种子、土壤、区域、材料或空间。
7．根据权利要求1中所述的化合物Ⅰ和/或Ⅱ制备权利要求1的杀真菌活性增效混合物的应用。
8．根据权利要求1中所述的化合物Ⅲ制备权利要求1的杀真菌活性增效混合物的应用。
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19616682 | 1996-04-26 | ||
| DE19616682.9 | 1996-04-26 | ||
| DE19617235.7 | 1996-04-30 | ||
| DE19617235 | 1996-04-30 | ||
| DE19635510 | 1996-09-02 | ||
| DE19635510.9 | 1996-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1216437A true CN1216437A (zh) | 1999-05-12 |
Family
ID=27216184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97194011A Pending CN1216437A (zh) | 1996-04-26 | 1997-04-22 | 杀真菌混合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6194417B1 (zh) |
| EP (1) | EP0900012B1 (zh) |
| JP (1) | JP2000509381A (zh) |
| KR (1) | KR20000065010A (zh) |
| CN (1) | CN1216437A (zh) |
| AR (1) | AR006853A1 (zh) |
| AT (1) | ATE214875T1 (zh) |
| AU (1) | AU732287B2 (zh) |
| BR (1) | BR9708827A (zh) |
| CA (1) | CA2252639A1 (zh) |
| CO (1) | CO4761035A1 (zh) |
| CZ (1) | CZ330798A3 (zh) |
| DE (1) | DE59706771D1 (zh) |
| DK (1) | DK0900012T3 (zh) |
| EA (1) | EA001042B1 (zh) |
| HU (1) | HUP9903722A3 (zh) |
| IL (1) | IL126080A0 (zh) |
| NZ (1) | NZ331767A (zh) |
| PL (1) | PL329507A1 (zh) |
| SK (1) | SK138598A3 (zh) |
| TW (1) | TW336158B (zh) |
| WO (1) | WO1997040675A1 (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO5040025A1 (es) * | 1997-05-30 | 2001-05-29 | Basf Ag | Mezclas fungicidas |
| US6316452B1 (en) | 1998-05-18 | 2001-11-13 | Basf Aktiengesellschaft | Fungicidal mixture |
| US6649566B2 (en) | 2001-12-13 | 2003-11-18 | Morse Enterprises Limited, Inc. | Stabilized concentrated formulations for enhancing plant defensive responses |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1569940A (zh) | 1967-04-27 | 1969-06-06 | ||
| DK0645084T3 (da) * | 1993-09-24 | 1996-08-26 | Basf Ag | Fungicide blandinger |
| CA2182529A1 (en) * | 1994-02-04 | 1995-08-10 | Herbert Bayer | Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them |
| WO1995025113A1 (en) * | 1994-03-15 | 1995-09-21 | Sloan-Kettering Institute For Cancer Research | Synthetic compounds which bind to h. pylori, and uses thereof |
| DE4423613A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4423612A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung |
| DE19528651A1 (de) * | 1995-08-04 | 1997-02-06 | Basf Ag | Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
| ATE185471T1 (de) * | 1995-08-17 | 1999-10-15 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit fenarimol |
-
1997
- 1997-04-22 BR BR9708827A patent/BR9708827A/pt not_active Application Discontinuation
- 1997-04-22 PL PL97329507A patent/PL329507A1/xx unknown
- 1997-04-22 EP EP97921687A patent/EP0900012B1/de not_active Expired - Lifetime
- 1997-04-22 AT AT97921687T patent/ATE214875T1/de not_active IP Right Cessation
- 1997-04-22 KR KR1019980708547A patent/KR20000065010A/ko not_active Application Discontinuation
- 1997-04-22 IL IL12608097A patent/IL126080A0/xx unknown
- 1997-04-22 HU HU9903722A patent/HUP9903722A3/hu unknown
- 1997-04-22 NZ NZ331767A patent/NZ331767A/en unknown
- 1997-04-22 CA CA002252639A patent/CA2252639A1/en not_active Abandoned
- 1997-04-22 AU AU27668/97A patent/AU732287B2/en not_active Ceased
- 1997-04-22 DK DK97921687T patent/DK0900012T3/da active
- 1997-04-22 DE DE59706771T patent/DE59706771D1/de not_active Expired - Lifetime
- 1997-04-22 CZ CZ983307A patent/CZ330798A3/cs unknown
- 1997-04-22 CN CN97194011A patent/CN1216437A/zh active Pending
- 1997-04-22 WO PCT/EP1997/002021 patent/WO1997040675A1/de not_active Application Discontinuation
- 1997-04-22 US US09/155,089 patent/US6194417B1/en not_active Expired - Fee Related
- 1997-04-22 EA EA199800929A patent/EA001042B1/ru not_active IP Right Cessation
- 1997-04-22 JP JP9538537A patent/JP2000509381A/ja active Pending
- 1997-04-22 SK SK1385-98A patent/SK138598A3/sk unknown
- 1997-04-25 CO CO97022207A patent/CO4761035A1/es unknown
- 1997-04-25 AR ARP970101704A patent/AR006853A1/es unknown
- 1997-04-26 TW TW086105487A patent/TW336158B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| DK0900012T3 (da) | 2002-07-01 |
| JP2000509381A (ja) | 2000-07-25 |
| CO4761035A1 (es) | 1999-04-27 |
| NZ331767A (en) | 2000-02-28 |
| CZ330798A3 (cs) | 1999-06-16 |
| HUP9903722A2 (hu) | 2000-03-28 |
| US6194417B1 (en) | 2001-02-27 |
| AU732287B2 (en) | 2001-04-12 |
| AU2766897A (en) | 1997-11-19 |
| ATE214875T1 (de) | 2002-04-15 |
| CA2252639A1 (en) | 1997-11-06 |
| TW336158B (en) | 1998-07-11 |
| SK138598A3 (en) | 1999-04-13 |
| EA001042B1 (ru) | 2000-08-28 |
| EP0900012B1 (de) | 2002-03-27 |
| BR9708827A (pt) | 1999-08-03 |
| HUP9903722A3 (en) | 2001-08-28 |
| IL126080A0 (en) | 1999-05-09 |
| EP0900012A1 (de) | 1999-03-10 |
| WO1997040675A1 (de) | 1997-11-06 |
| PL329507A1 (en) | 1999-03-29 |
| DE59706771D1 (de) | 2002-05-02 |
| AR006853A1 (es) | 1999-09-29 |
| KR20000065010A (ko) | 2000-11-06 |
| EA199800929A1 (ru) | 1999-04-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100401891C (zh) | 杀真菌混合物 | |
| HU224040B1 (hu) | Fungicid keverékek | |
| AU739192B2 (en) | Fungicidal mixtures | |
| CN1106148C (zh) | 杀真菌混合物 | |
| CN1216442A (zh) | 杀真菌混合物 | |
| US6172063B1 (en) | Fungicidal mixtures | |
| CN1216441A (zh) | 杀真菌混合物 | |
| US6172094B1 (en) | Fungicide mixtures | |
| CN1216437A (zh) | 杀真菌混合物 | |
| CN1167342C (zh) | 杀真菌混合物 | |
| CN1216898A (zh) | 杀真菌混合物 | |
| CN1258195A (zh) | 杀真菌混合物 | |
| CN1258194A (zh) | 杀真菌混合物 | |
| CN1152854A (zh) | 杀真菌混合物 | |
| CN1553772A (zh) | 杀真菌混合物 | |
| KR20000023687A (ko) | 살진균성 혼합물 | |
| CN1259015A (zh) | 杀真菌混合物 | |
| JP4324251B2 (ja) | 殺菌剤組成物 | |
| CN1213950A (zh) | 杀真菌混合物 | |
| CN1224995A (zh) | 杀真菌混合物 | |
| MXPA98008776A (es) | Mezclas fungicidas | |
| CN1666613A (zh) | 杀真菌混合物 | |
| CN1153455A (zh) | 杀真菌混合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |