CN1216440A - 杀菌混剂 - Google Patents
杀菌混剂 Download PDFInfo
- Publication number
- CN1216440A CN1216440A CN97194053A CN97194053A CN1216440A CN 1216440 A CN1216440 A CN 1216440A CN 97194053 A CN97194053 A CN 97194053A CN 97194053 A CN97194053 A CN 97194053A CN 1216440 A CN1216440 A CN 1216440A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- formula
- iii
- compound
- chemical compounds
- 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 38
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 6
- 239000000417 fungicide Substances 0.000 title claims abstract description 6
- -1 C2C6-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
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 6
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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 44
- 229940084434 fungoid Drugs 0.000 claims description 11
- 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 9
- 238000000034 method Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 230000001954 sterilising effect Effects 0.000 claims description 5
- 230000002195 synergetic effect Effects 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 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
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 230000003449 preventive effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000857 drug effect Effects 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 208000031888 Mycoses Diseases 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
- 241000233622 Phytophthora infestans Species 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000002253 acid Substances 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
- 239000000428 dust Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241000221785 Erysiphales 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
- 206010017533 Fungal infection Diseases 0.000 description 2
- 244000299507 Gossypium hirsutum Species 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
- 235000007688 Lycopersicon esculentum Nutrition 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
- 241000233679 Peronosporaceae Species 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
- 239000005821 Propamocarb Substances 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect 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
- 239000004927 clay Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 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
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 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
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-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
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000235349 Ascomycota Species 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001157813 Cercospora Species 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000510928 Erysiphe necator 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
- 241000233866 Fungi Species 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
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010027146 Melanoderma Diseases 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
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale 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
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 241000607479 Yersinia pestis 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
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 230000008485 antagonism Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 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
- 150000004657 carbamic acid derivatives Chemical class 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
- 238000006243 chemical reaction Methods 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
- 239000007931 coated granule Substances 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
- 239000013068 control sample Substances 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
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 244000000004 fungal plant pathogen Species 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
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-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
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 239000011159 matrix material Substances 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
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 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
- 239000000047 product Substances 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
- 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
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 238000012360 testing method Methods 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent 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
- A01N43/64—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
杀菌混剂,它含有增效作用剂量的以下组分:a)式Ⅰ所示氨基甲酸酯,式中T是CH或N,n是0、1或2,R是卤素、C1-C4-烷基或C1-C4-卤代烷基,当n是2时,基团R可能彼此不相同,和/或b)式Ⅱ所示肟醚,式中的取代基具有如下含义;X是氧或亚氨基(NH);Y是CH或N;Z是氧、硫、亚氨基或C1-C4-烷基亚氨基;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,或者是苄基,其上可以被部分或全部卤代和/或在其上带有1至3个下列基团: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;C)式Ⅲ所示氨基甲酸酯(CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3Ⅲ。
Description
式中T是CH或N,n是0、1或2,R是卤素、C1-C4-烷基或C1-C4-卤代烷基,当n是2时,基团R可能彼此不相同,和/或
式中的取代基具有如下含义;
X是氧或亚氨基(NH);
Y是CH或N;
Z是氧、硫、亚氨基(NH)或C1-C4-烷基亚氨基(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,或者是苄基,其上可以被部分或全部卤代和/或在其上带有1至3个下列基团: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;
c)式Ⅲ所示氨基甲酸酯
(CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3 Ⅲ
此外,本发明涉及到用化合物Ⅰ和/或Ⅱ和Ⅲ的混剂防治有害真菌的方法和化合物Ⅰ和/或Ⅱ和化合物Ⅲ在制备这些混剂中的应用。
式Ⅰ所示化合物,它们的制备和它们防治有害真菌的活性均在文献中已有报道(WO-A96/01,256和WO-A96/01,258)。
式Ⅱ所示化合物,它们的制备和它们防治有害真菌的活性在以下文献中已有描述:WO-A95/21,153,WO-A95/21,154和DE 1 95 28651.0。
化合物Ⅲ,它的制备和它防治有害真菌的应用也已有报道[德国专利申请公开DE-OS-1567169,通用名称:霜霉威(propamo-card)]。
本发明的一个目的是提供这样的混剂,其具有改善了的防治有害真菌活性,同时降低制剂中有效成分的总量(增效混剂),目的是减少施药剂量和扩大这些已知化合物的活性谱。
因此,我们发现了本文开头定义的混剂,完成了这个目标。另外我们发现,化合物Ⅰ和/或Ⅱ和化合物Ⅲ同时混用或同时分别施用或化合物Ⅰ和/或Ⅱ和化合物Ⅲ前后连续施用时比使用单个化合物对有害真菌能有更好的灭菌药效。
式Ⅰ表示了尤其好的氨基甲酸酯化合物,其中取代基的组合相应于下表中的一栏:
序号 | T | Rn |
Ⅰ.1 | N | 2-F |
Ⅰ.2 | N | 3-F |
Ⅰ.3 | N | 4-F |
Ⅰ.4 | N | 2-Cl |
Ⅰ.5 | N | 3-Cl |
Ⅰ.6 | N | 4-Cl |
Ⅰ.7 | N | 2-Br |
序号 | T | Rn |
Ⅰ.8 | N | 3-Br |
Ⅰ.9 | N | 4-Br |
Ⅰ.10 | N | 2-CH3 |
Ⅰ.11 | N | 3-CH3 |
Ⅰ.12 | N | 4-CH3 |
Ⅰ.13 | N | 2-CH2CH3 |
Ⅰ.14 | N | 3-CH2CH3 |
Ⅰ.15 | N | 4-CH2CH3 |
Ⅰ.16 | N | 2-CH(CH3)2 |
Ⅰ.17 | N | 3-CH(CH3)2 |
Ⅰ.18 | N | 4-CH(CH3)2 |
Ⅰ.19 | N | 2-CF3 |
Ⅰ.20 | N | 3-CF3 |
Ⅰ.21 | N | 4-CF3 |
Ⅰ.22 | N | 2,4-F2 |
Ⅰ.23 | N | 2,4-Cl2 |
Ⅰ.24 | N | 3,4-Cl2 |
Ⅰ.25 | N | 2-Cl,4-CH3 |
Ⅰ.26 | N | 3-Cl,4-CH3 |
Ⅰ.27 | CH | 2-F |
Ⅰ.28 | CH | 3-F |
Ⅰ.29 | CH | 4-F |
Ⅰ.30 | CH | 2-Cl |
Ⅰ.31 | CH | 3-Cl |
Ⅰ.32 | CH | 4-Cl |
Ⅰ.33 | CH | 2-Br |
Ⅰ.34 | CH | 3-Br |
Ⅰ.35 | CH | 4-Br |
Ⅰ.36 | CH | 2-CH3 |
Ⅰ.37 | CH | 3-CH3 |
Ⅰ.38 | CH | 4-CH3 |
Ⅰ.39 | CH | 2-CH2CH3 |
Ⅰ.40 | CH | 3-CH2CH3 |
Ⅰ.41 | CH | 4-CH2CH3 |
Ⅰ.42 | CH | 2-CH(CH3)2 |
Ⅰ.43 | CH | 3-CH(CH3)2 |
Ⅰ.44 | CH | 4-CH(CH3)2 |
Ⅰ.45 | CH | 2-CF3 |
Ⅰ.46 | CH | 3-CF3 |
序号 | T | Rn |
Ⅰ.47 | CH | 4-CF3 |
Ⅰ.48 | CH | 2,4-F2 |
Ⅰ.49 | CH | 2,4-Cl2 |
Ⅰ.50 | CH | 3,4-Cl2 |
Ⅰ.51 | CH | 2-Cl,4-CH3 |
Ⅰ.52 | CH | 3-Cl,4-CH3 |
化合物Ⅰ.12、Ⅰ.23、Ⅰ.32和Ⅰ.38是特别优选的。
通式Ⅱ表示甲氧基-丙烯酸酯和肟醚化合物的特别代表性例子,其中X是氧和Y是CH,或X是亚氨基和Y是N。
另外,式中Z是氧的化合物Ⅱ也是优选的。
式中R′是烷基或苄基的化合物Ⅱ同样是优选的。
从它们的应用为目的考虑,本发明的增效混剂中特别优选的化合物Ⅱ汇列于下表。
表2
表3
表A
序号 | ZR′ |
Ⅱ.1 | O-CH2CH2CH3 |
Ⅱ.2 | O-CH(CH3)2 |
Ⅱ.3 | O-CH2CH2CH2CH3 |
Ⅱ.4 | O-CH(CH3)CH2CH3 |
Ⅱ.5 | O-CH2CH(CH3)2 |
Ⅱ.6 | O-C(CH3)3 |
Ⅱ.7 | S-C(CH3)3 |
Ⅱ.8 | O-CH(CH3)CH2CH2CH3 |
Ⅱ.9 | O-CH2C(CH3)3 |
Ⅱ.10 | O-CH2C(Cl)=CCl2 |
Ⅱ.11 | O-CH2CH=CH-Cl(反式) |
Ⅱ.12 | O-CH2C(CH3)=CH2 |
Ⅱ.13 | O-CH2-(环丙基) |
Ⅱ.14 | O-CH2-C6H5 |
Ⅱ.15 | O-CH2-[4-F-C6H4] |
Ⅱ.16 | O-CH2CH3 |
Ⅱ.17 | O-CH(CH2CH3)2 |
基于C=Y双键,式Ⅱ所示化合物可以存在E式或Z式构型(相对于羧酸官能团)。相应地,它们可以以纯的E式或Z式异构体、或者以E/Z异构体混合物形式用于本发明的混剂中。优选的是E/Z异构体混合物或E式异构体,化合物Ⅱ的E式异构体是特别优选的。
在化合物Ⅱ侧链上肟醚基团的C=N双键各可以存在纯E式或Z式异构体或E/Z异构体混合物。化合物Ⅱ可以以异构体混合物或以纯异构体用于本发明的混剂。从它们的应用为目的考虑,特别优选这些化合物Ⅱ,其侧链末端的肟醚基团是顺式构型(OCH3基团对于ZR′基团)。
由于它们的碱性特性,化合物Ⅰ和Ⅱ可以与无机酸或有机酸或与金属离子形成加合物或盐。
无机酸例如氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸,硫酸、磷酸和硝酸。
适宜的有机酸例如为甲酸、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的磺酸)、芳基磺酸或芳基二磺酸(芳基如苯基和萘基,其上连有1或2个磺基)、烷基磷酸(具有1至20个碳原子的直链或支链烷基的磷酸)、芳基磷酸或芳基二磷酸(芳基如苯基和萘基,其上连有1至2个磷酸基团),这些烷基和芳基上可能还连有取代基,如对甲苯磺酸、邻羟基苯甲酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧苯甲酸等。
适宜的金属离子特别是第二主族元素的离子,特别是钙和镁;第三和第四主族元素的离子特别是铝、锡和铅;第一至第八副族元素的离子,特别是铬、锰、铁、钴、镍、铜、锌等。特别优选的是第四周期副族元素的金属离子。这些金属在此情况下可以以它们可能的不同的价存在。
当制备混剂时,最好采用纯的有效成分Ⅰ、Ⅱ和Ⅲ,如果有必要,混剂中可以另外混入其他防治有害真菌或其他有害生物如昆虫、螨类或线虫的有效成分,或者还可以混入除草-或者生长调节有效成分或化学肥料。
化合物Ⅰ和/或Ⅱ和Ⅲ的混剂,或者化合物Ⅰ和/或Ⅱ和Ⅲ同时混用或分别施用,都显示出对植物病原真菌具有卓越的广谱活性,特别是对于子囊菌纲、半知菌纲、藻菌纲和担子菌纲。它们中的一些具有内吸作用,因此可用作为叶面和土壤施用的杀菌剂。
它们用于各种植物及各种种子、对防治大量真菌病害特别有重要意义,这些植物如棉花、蔬菜类(如黄瓜、菜豆和葫芦科植物)、大麦、牧草、燕麦、咖啡、玉米、果树类、水稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗。
它们特别地适宜防治下列植物病原真菌:禾谷类白粉病,葫芦科植物白粉病,苹果白粉病,禾谷类锈病,棉花、水稻、草坪上的菌核病,禾谷类和甘蔗的黑穗病,苹果黑星病,禾谷类网斑病,小麦颖枯病,草莓、蔬菜、观赏植物和葡萄的灰霉病,花生褐斑病,小麦、大麦的眼斑病,稻瘟病,马铃薯和番茄的晚疫病,黄瓜和啤酒花的霜霉病,葡萄白粉病,蔬菜和果树的黑斑病,各种植物的枯萎病和黄萎病。
另外,它们可以用于材料保护(如木材保护),如防治由拟青霉菌引起的木材腐烂。
化合物Ⅰ和/或Ⅱ和Ⅲ可以同时混用或分别使用或前后连续使用,在分别使用的情况下,施用顺序一般对防治效果没有任何影响。
化合物Ⅰ和/或Ⅱ和Ⅲ通常使用的重量比从200∶1至0.1∶1,优选的是100∶1至1∶1,特别是50∶1至5∶1(Ⅲ∶Ⅰ和/或Ⅱ)。
依据所需效果的性质,本发明混剂的施药剂量,对化合物Ⅰ和/或Ⅱ而言为,一般为每公顷0.005至0.5千克,优选的为0.01至0.5千克,特别是为0.01至0.3千克。
相应地,化合物Ⅲ的施药剂量为每公顷0.1至10千克,优选的为0.5至5千克,特别是从1至4千克。
用作种子处理时,每千克种子的该混剂用药剂量通常是从0.001至100克,优选的为0.01至50克,特别是0.01至10克。
如果防治植物病原有害真菌,对种子、植株或播前或播后、或者芽前或芽后的土壤通过喷雾或喷粉、分别使用或混用化合物Ⅰ和/或Ⅱ和Ⅲ或化合物Ⅰ和/或Ⅱ和Ⅲ的混剂都是有效的。
本发明的杀菌增效混剂或化合物Ⅰ和/或Ⅱ和Ⅲ可施用形式例如可为:可直接喷雾溶液、粉剂和悬浮剂,或高浓度水剂、油剂或其他悬浮剂、分散剂、乳剂、油分散制剂、膏剂、粉尘剂、撒施剂或颗粒剂,施用方法有喷雾、弥雾、喷粉、撒施或浇淋。使用的形式依赖于预定的目的,在任何情况下,它们应该保证本发明的混剂得到尽可能良好均匀的分布。
以原则上已知的方法进行配制,如通过添加溶剂和/或载体。通常在制剂中添加惰性助剂如乳化剂或分散剂。
适宜的表面活性剂是芳香族磺酸类如木素磺酸、苯磺酸、萘磺酸和二丁基萘磺酸的、和脂肪酸类、烷基-和烷基芳基磺酸酯类、烷基硫酸酯类、月桂基醚硫酸酯类和脂肪醇硫酸酯类的碱金属盐、-碱土金属盐和-铵盐,和硫酸化十六醇、十七醇和十八醇的盐,以及脂肪醇乙二醇醚类,磺化萘及其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,聚氧乙烯辛基苯酚醚,乙氧基化异辛基苯酚、辛基苯酚或壬基苯酚,烷基苯基聚乙二醇醚或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三醇、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烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨醇酯类,木素亚硫酸盐纸浆废液或甲基纤维素。
粉剂、撒施剂和粉尘剂通过化合物Ⅰ和/或Ⅱ或Ⅲ或化合物Ⅰ和/或Ⅱ和Ⅲ的混合物与一种固体载体混合或一起研磨制备。
颗粒剂(如包衣颗粒、浸渍颗粒或均质颗粒)通常用有效成分与固体载体相接合来制备。
填料或固体载体是天然矿物材料,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、胶块粘土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,合成矿物材料,化学肥料如硫酸铵、磷酸铵、硝酸铵、尿素,和植物源产品如谷物粉、树皮粉、木屑和坚果壳粉、纤维素粉,或其他的固体载体。
一般而言,制剂中化合物Ⅰ和/或Ⅱ或Ⅲ之一或化合物Ⅰ和/或Ⅱ和Ⅲ混合物含量,按重量计,为0.1至95%,优选为0.5至90%。所用有效成分纯度为90%至100%,优选为95%至100%(依据核磁共振波谱或高效液相色谱)。
化合物Ⅰ和/或Ⅱ和Ⅲ或混剂或相应制剂这样使用,其中以混剂或分别使用的化合物Ⅰ和/或Ⅱ和Ⅲ的杀菌有效剂量处理有害真菌或待防止受它们侵染的植物、种子、土壤、田间、材料或场所,在有害真菌侵染之前或侵染之后施药都有效。
这些化合物及其混剂的杀菌活性通过下面试验予以证明:
有效成分分别或共同加工成按重量计10%的乳油,基质为按重量计70%环己酮,20%NekanilLN(LutensolAP6,基于乙氧基化烷基苯酚类的、具有乳化和分散作用的润湿剂)和10%EmulphorEL(EmulanEL,基于乙氧基化的脂肪醇的乳化剂)的一种混合物,用水稀释至所需要的浓度。
通过检测叶片受侵染面积的百分率进行效果判定。把这些百分比转换成防治效果等级。有效成分混合物的期望效果等级用Colby公式计算[S.R.Colby,杂草,15,20-22(1967)],并与观察的实际效果比较。
Colby公式:
E=X+Y-X×Y/100
式中:
E:期望防效等级,表示为有效成分A和B以浓度a和b的混合物
施用后相对未处理的对照样的%
X:防治效果等级,表示为有效成分A以浓度a施用后相对未处理
的对照样的%
Y:防治效果等级,表示为有效成分B以浓度b施用后相对未处理
的对照样的%
药效等级(W)是通过下面Abbot公式计算:
W=(1-α)×100/β
α:经处理植株的真菌侵染的百分率
β:未处理(对照)植株真菌侵染的百分率
药效为0表示处理植株的侵染水平相当于未处理植株的侵染水平;防效为100表示处理植株没有受到侵染。
实施例1-10
对番茄晚疫病(Phytophthora infestans)的药效
盆栽番茄品种为“Grobe Fleischtomate”的叶片,用含有10%有效成分、63%环己酮和27%乳化剂组成的储备溶液配成的水悬浮液喷雾,直到喷雾雾滴滴下为止,第二天,用晚疫病游动孢子的水悬浮液接种叶片。然后把供试植株置于温度16-18℃的水汽饱和的容器中。6天后,疫病发展到接种的未处理对照植株的病害水平肉眼可见的程度,用目测法检查百分率。
病叶面积百分数目测值转换为相对于未处理对照样的以百分数表示的防效等级。防效等级为0表示和未处理植株同样的致病水平,防效为100表示致病水平为0%。有效成分混合物的期望效果用Colby公式计算[Colby,S.R.,“计算除草剂混用的增效和拮抗反应”,杂草,15,20-22(1967)],并与观察的实际效果比较。
表4
实验序号 | 有效成分 | 喷雾混合物有效成分的浓度(ppm) | 未处理植株的防效(%) |
1ⅴ | 对照(未处理) | (致病水平98%) | 0 |
2ⅴ | A=表2A,序号Ⅱ.2 | 1641 | 880 |
3ⅴ | B=表2A,序号Ⅱ.4 | 1641 | 3900 |
4ⅴ | Ⅲ=霜霉成(propamocarb) | 125633116 | 18880 |
表5
*)使用Colby公式计算得到
实验序号 | 喷雾混合物有效成分的浓度(ppm) | 实测防效 | 计算防效*) |
5 | 16A+16Ⅲ | 49 | 8 |
6 | 16A+31Ⅲ | 49 | 15 |
7 | 16A+63Ⅲ | 39 | 15 |
8 | 16A+125Ⅲ | 69 | 24 |
9 | 16B+31Ⅲ | 59 | 43 |
10 | 16B+63Ⅲ | 59 | 43 |
实施例1-10的结果证明,以所有比例混合的本发明药物实测防效高于用Colby公式预先计算的防效。
Claims (6)
1、杀菌混剂,含有增效杀菌作用剂量的以下组分:
式中T是CH或N,n是0、1或2,R是卤素、C1-C4-烷基或C1-C4-卤代烷基,当n是2时,基团R可能彼此不相同,和/或
式中的取代基具有如下含义;
X是氧或亚氨基(NH);
Y是CH或N;
Z是氧、硫、亚氨基(NH)或C1-C4-烷基亚氨基(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,或者是苄基,其上可以被部分或全部卤代和/或在其上带有1至3个下列基团: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;
c)式Ⅲ所示氨基甲酸酯
(CH3)2N-CH2CH2CH2-NH-CO2-CH2CH2CH3 Ⅲ。
2、根据权利要求1的杀菌混剂,其特征在于,化合物Ⅲ与化合物Ⅰ和/或Ⅱ的重量比是200∶1至0.1∶1。
3、防治有害真菌的方法,其特征在于,用根据权利要求1的一种化合物Ⅰ和/或化合物Ⅱ以及根据权利要求1的一种化合物Ⅲ处理有害真菌、它们的环境或待防止受它们侵染的植物、种子、土壤、田间、材料或场所。
4、根据权利要求3的方法,其特征在于,用根据权利要求1的一种化合物Ⅰ和/或化合物Ⅱ以及根据权利要求1的一种化合物Ⅲ同时混用或分别使用或前后连续使用。
5、根据权利要求3的方法,其特征在于,用根据权利要求1的一种化合物Ⅰ和/或化合物Ⅱ以每公顷0.005至0.5千克的剂量处理有害真菌、它们的环境,或待防止受它们侵染的植物、种子、土壤、田间、材料或场所。
6、根据权利要求3的方法,其特征在于,用根据权利要求1的化合物Ⅲ以每公顷0.1至10千克的剂量处理有害真菌、它们的环境或待防止受它们侵染的植物、种子、土壤、田间、材料或场所。
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19616689.6 | 1996-04-26 | ||
DE19616689 | 1996-04-26 | ||
DE19617069 | 1996-04-29 | ||
DE19617069.9 | 1996-04-29 | ||
DE19635505.2 | 1996-09-02 | ||
DE19635505 | 1996-09-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1216440A true CN1216440A (zh) | 1999-05-12 |
Family
ID=27216187
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97194053A Pending CN1216440A (zh) | 1996-04-26 | 1997-04-23 | 杀菌混剂 |
Country Status (21)
Country | Link |
---|---|
US (1) | US6028093A (zh) |
EP (1) | EP0900011B1 (zh) |
JP (1) | JP2000509062A (zh) |
KR (1) | KR20000065014A (zh) |
CN (1) | CN1216440A (zh) |
AR (1) | AR006857A1 (zh) |
AT (1) | ATE215309T1 (zh) |
AU (1) | AU722194B2 (zh) |
BR (1) | BR9708805A (zh) |
CA (1) | CA2252641A1 (zh) |
CO (1) | CO4761030A1 (zh) |
CZ (1) | CZ289349B6 (zh) |
DE (1) | DE59706871D1 (zh) |
DK (1) | DK0900011T3 (zh) |
EA (1) | EA001105B1 (zh) |
IL (1) | IL126230A0 (zh) |
NZ (1) | NZ332077A (zh) |
PL (1) | PL329522A1 (zh) |
SK (1) | SK144398A3 (zh) |
TW (1) | TW337981B (zh) |
WO (1) | WO1997040678A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998016499A1 (fr) * | 1996-10-15 | 1998-04-23 | Shionogi & Co., Ltd. | Derives d'oxime, derives d'hydrazone, et leur utilisation |
US8188003B2 (en) * | 2000-05-03 | 2012-05-29 | Basf Aktiengesellschaft | Method of inducing virus tolerance of plants |
DE102004049761A1 (de) * | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
KR101259242B1 (ko) | 2008-03-24 | 2013-04-29 | 닛뽕소다 가부시키가이샤 | 식물 병해 방제제 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL157191C (nl) * | 1966-12-17 | Schering Ag | Werkwijze voor het bereiden van een preparaat met fungicide en fungistatische werking. | |
JPS6425763A (en) * | 1987-04-24 | 1989-01-27 | Mitsubishi Chem Ind | Pyrazoles and insecticide and acaricide containing said pyrazoles as active ingredient |
DE4304172A1 (de) * | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
CA2182529A1 (en) * | 1994-02-04 | 1995-08-10 | Herbert Bayer | Phenylacetic acid derivatives, preparation thereof and intermediates therefor, and compositions containing them |
EP0741694B1 (de) * | 1994-02-04 | 2003-04-02 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
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 |
TW401275B (en) * | 1995-09-25 | 2000-08-11 | Basf Ag | Compositions and methods of controlling harmful fungi |
-
1997
- 1997-04-23 US US09/171,563 patent/US6028093A/en not_active Expired - Fee Related
- 1997-04-23 KR KR1019980708551A patent/KR20000065014A/ko not_active Application Discontinuation
- 1997-04-23 SK SK1443-98A patent/SK144398A3/sk unknown
- 1997-04-23 NZ NZ332077A patent/NZ332077A/en unknown
- 1997-04-23 AT AT97920739T patent/ATE215309T1/de not_active IP Right Cessation
- 1997-04-23 CA CA002252641A patent/CA2252641A1/en not_active Abandoned
- 1997-04-23 PL PL97329522A patent/PL329522A1/xx unknown
- 1997-04-23 JP JP9538551A patent/JP2000509062A/ja active Pending
- 1997-04-23 BR BR9708805A patent/BR9708805A/pt unknown
- 1997-04-23 EP EP97920739A patent/EP0900011B1/de not_active Expired - Lifetime
- 1997-04-23 WO PCT/EP1997/002048 patent/WO1997040678A1/de not_active Application Discontinuation
- 1997-04-23 IL IL12623097A patent/IL126230A0/xx not_active IP Right Cessation
- 1997-04-23 CZ CZ19983378A patent/CZ289349B6/cs not_active IP Right Cessation
- 1997-04-23 DK DK97920739T patent/DK0900011T3/da active
- 1997-04-23 DE DE59706871T patent/DE59706871D1/de not_active Expired - Lifetime
- 1997-04-23 EA EA199800895A patent/EA001105B1/ru not_active IP Right Cessation
- 1997-04-23 AU AU27009/97A patent/AU722194B2/en not_active Ceased
- 1997-04-23 CN CN97194053A patent/CN1216440A/zh active Pending
- 1997-04-25 AR ARP970101708A patent/AR006857A1/es unknown
- 1997-04-25 CO CO97022200A patent/CO4761030A1/es unknown
- 1997-04-25 TW TW086105452A patent/TW337981B/zh active
Also Published As
Publication number | Publication date |
---|---|
EA199800895A1 (ru) | 1999-06-24 |
EA001105B1 (ru) | 2000-10-30 |
PL329522A1 (en) | 1999-03-29 |
CZ337898A3 (cs) | 1999-04-14 |
AU2700997A (en) | 1997-11-19 |
DE59706871D1 (de) | 2002-05-08 |
BR9708805A (pt) | 1999-08-03 |
AR006857A1 (es) | 1999-09-29 |
ATE215309T1 (de) | 2002-04-15 |
CO4761030A1 (es) | 1999-04-27 |
DK0900011T3 (da) | 2002-07-01 |
CZ289349B6 (cs) | 2002-01-16 |
WO1997040678A1 (de) | 1997-11-06 |
US6028093A (en) | 2000-02-22 |
SK144398A3 (en) | 1999-04-13 |
NZ332077A (en) | 2000-02-28 |
KR20000065014A (ko) | 2000-11-06 |
CA2252641A1 (en) | 1997-11-06 |
EP0900011A1 (de) | 1999-03-10 |
JP2000509062A (ja) | 2000-07-18 |
EP0900011B1 (de) | 2002-04-03 |
AU722194B2 (en) | 2000-07-27 |
IL126230A0 (en) | 1999-05-09 |
TW337981B (en) | 1998-08-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1145418C (zh) | 杀真菌混合物 | |
CN1079638C (zh) | 杀真菌混合物 | |
CN100377647C (zh) | 杀真菌混合物 | |
CN1156218C (zh) | 杀真菌混合剂 | |
CN1106148C (zh) | 杀真菌混合物 | |
CN1119824A (zh) | 杀真菌组合物 | |
CN1293809C (zh) | 杀菌混剂 | |
CN1216440A (zh) | 杀菌混剂 | |
CN1197461C (zh) | 杀真菌混合物 | |
CN1305375C (zh) | 基于二噻农的杀真菌混合物 | |
CN1122442C (zh) | 杀真菌混剂 | |
CN1331562A (zh) | 杀真菌混合物 | |
CN1216442A (zh) | 杀真菌混合物 | |
CN1216439A (zh) | 杀菌混剂 | |
CN1216897A (zh) | 杀真菌混合物 | |
CN1216441A (zh) | 杀真菌混合物 | |
CN1711022A (zh) | 用于防治稻病原体的杀真菌混合物 | |
CN1231577A (zh) | 杀菌混剂 | |
CN101129139B (zh) | 防治有害真菌的方法 | |
KR100379799B1 (ko) | 살진균성 혼합물 및 유해진균의 억제방법 | |
CN1130124C (zh) | 杀真菌混合物 | |
CN1138474C (zh) | 杀真菌混合物 | |
CN1258194A (zh) | 杀真菌混合物 | |
EP0912088B1 (de) | Fungizide mischungen | |
CN1258195A (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 |