CA2132048A1 - Fungicidal mixtures - Google Patents
Fungicidal mixturesInfo
- Publication number
- CA2132048A1 CA2132048A1 CA002132048A CA2132048A CA2132048A1 CA 2132048 A1 CA2132048 A1 CA 2132048A1 CA 002132048 A CA002132048 A CA 002132048A CA 2132048 A CA2132048 A CA 2132048A CA 2132048 A1 CA2132048 A1 CA 2132048A1
- Authority
- CA
- Canada
- Prior art keywords
- dithiocarbamate
- compound
- ethylenebis
- formula
- zinc
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 13
- -1 oxime ether carboxamide Chemical class 0.000 claims abstract description 20
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000011701 zinc Substances 0.000 claims abstract description 9
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 9
- AWYFNIZYMPNGAI-UHFFFAOYSA-L ethylenebis(dithiocarbamate) Chemical compound [S-]C(=S)NCCNC([S-])=S AWYFNIZYMPNGAI-UHFFFAOYSA-L 0.000 claims abstract description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 48
- 241000233866 Fungi Species 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 5
- 230000002195 synergetic effect Effects 0.000 claims description 5
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 4
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 9
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier 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
- 239000006185 dispersion Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 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
- 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
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 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
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003337 fertilizer 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
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids 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
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000009566 rice Nutrition 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
- 238000001228 spectrum Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 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
- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-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
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-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
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
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- 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
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
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- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000079253 Byssochlamys spectabilis Species 0.000 description 1
- 244000025254 Cannabis sativa 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
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- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N hydrofluoric acid Substances F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
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- 235000009973 maize Nutrition 0.000 description 1
- 229920000940 maneb Polymers 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
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
- 229920000257 metiram Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 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
- 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
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000004321 preservation 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SRYYCRXKYKWXDQ-PTGKCMAJSA-N success Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)C1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRYYCRXKYKWXDQ-PTGKCMAJSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Fungicidal mixtures Abstract A fungicidal mixture containing a) the oxime ether carboxamide of the formula I
Description
BASF Aktiengesellschaft 931555 O.Z. 0050/44323 21320~
Fungicidal mixtures The present invention relates to a fungicidal mixture which con-5 tains a) the oxime ether carboxamide of the formula I
C=NOCH3 and b) a dithiocarbamate (II) selected from the group - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and - zinc ethylenebis(dithiocarbamate) (IId) 25 in a synergistically active amount.
The invention additionally relates to processes for controlling harmful fungi using mixtures of the compounds I and II and the use of the compound I and the compounds II for the production of 30 mixtures of this type.
The compound of the formula I, its preparation and its action against harmful fungi are disclosed in the literature (EP-A 477 631).
The dithiocarbamates II (IIa: common name: mancozeb, US-A 3,379,610; IIb: common name: maneb, US-A 2,504,404; IIc:
former common name: metiram, US-A 3,248,400; IId: common name:
zineb, US-A 2,457,674), their preparation and their action 40 against harmful fungi are likewise known.
With respect to a decrease in the application rates and an im-provement of the spectrum of action of known compound3, the pres-ent invention is based on mixtures which, with a reduced total 45 amount of applied active compo~nds, have an improved action -against harmful fungi (synergistic mixtures).
- . , . , - : . ~ ,, , . , :
BASF Aktiengesellschaft 931555 0.Z. 0050/44323 21320~8 Accordingly, the mixtures defined at the beginning have been found. It has-additionally been found that on simultaneous joint or separate application of the compound I and the compounds II or on application of the compound I and the compounds II in succes-5 sion, harmful fungi can be controlled better than with the indi-vidual compounds.
The compound of the formula I can be present in the E or the Z
configuration with respect to the C=X double bond (with respect 10 to the carboxylic acid function group). Accordingly, it can be used in the mixture according to the invention in each case ei-ther as the pure ~ or Z isomer or as an ~/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, the E iso-mer being particularly preferred.
~ecause of the basic character of the NH group, the compound I is ab~e to form salts or adducts with inorganic or organic acids or with metal ions.
20 ~xamples of inorganic acids are hydrohalic acids such as hydro-fluoric acid, hydrochloric acid, hydrobromic acid and hydriodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carbonic 25 acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals 30 having 1 to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such a~ phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phos-phonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphos-~5 phonic acids (aromatic radicals ~uch as phenyl and naphthyl whichcarry one or two phosphoric acid radicals), the alkyl and aryl radicals being able to carry further substituents, eg. p-toluene-sulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxy-benzoic acid, 2-acetoxybenzoic acid etc.
Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, as well as of the first to eighth subgroup, in particular 45 chromium, manganese, iron, cobalt, nickel, copper, zinc and oth-ers. The metal ions of the elements of the subgroups of the fourth period are particularly preferred. The metals can in this ., : : . , .
': ' '' ' ' , ': ' - ~ ' .
- :
.,~" - "
~ .
;:- . , BASF Aktiengesellschaft 931555 O.Z. 0050/44323 21320~
case be present in the different valencies applicable to them.
Preferably, the pure active compounds I and II are employed in the preparation of the mixtures, to which, if required, further 5 active compounds against harmful fungi or other pests such as in-sects, arachnids or nematodes, or alternatively herbicidal or growth-regulating active compounds or fertilizers, can be ad-mixed.
10 The mixtures of the compounds I and II and the simultaneous joint or separate use of the compounds I and II are distinguished by an outstanding action against a wide spectrum of phytopathogenic fungi, in particular from the Ascomycetes and Basidiomycetes class. In some cases they are systemically active and can there-15 fore also be employed as foliar and soil fungicides.
They have particular importance for the control of a multiplicityof fungi on various crop plants such as cotton, vegetable plants (eg. cucumbers, beans and cucurbit~), barley, grass, oats, cof-20 fee, maize, fruit plants, rice, rye, soybean, grape, wheat, deco-rative plants, sugar cane and a multiplicity of seeds.
In particular, they are suitable for the control of the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on ce-25 reals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cu-curbits, Podosphaera leucotricha on apples, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago spe-cies on cereals and sugar cane, Venturia inaequalis (scab) on ap-ples, Helminthosporium species on cereals, Septoria nodorum on 30 wheat, Botrytis cinerea (gray mold) on strawberries and vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpo-trichoides on wheat and barley, Pyricularia oryzae on rice, Phy-tophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Alternaria species on vegetables and fruit and also Fu-35 sarium and Verticillium species.
They are additionally applicable in the protection of materials ;~
(eg. wood preservation), for example against Paecilomyces variotii.
The compounds I and II can be applied ~imultaneously ~ointly or separately, or in succession, the sequence in the case of sepa-rate application in general having no effect on the control suc-cess.
The compounds I and II are customarily applied in a weight ratio of from 2000:1 to 5:1, preferably from 1000:1 to 5:1, in BASF Aktienges~llschaft 931555 O.Z. 0050/4g3~3 213~48 particular from 500:1 to 5:1 (II:I).
Depending on the type of effect desired, the application rates of the mixtures according to the invention are from 0.005 to 5 0.5 kg/ha~, preferably from 0.01 to 0.5 kg/ha, in particular from 0.01 to 0.3 kg/ha, for the compound I. The application rates for the compound~ II are correspondingly from 0.1 to 10 kg/ha, pre-rerably from 0.5 to 5 kg/ha, in particular from 1 to 4 kg/ha.
10 In the treatment of seed, application rateQ of mixture of from 0.001 to 100 g/kg of seed, preferably from 0.01 to 50 g/kg, in particular from 0.01 to 10 g/kg, are generally used.
If harmful fungi which are pathogenic for plants are to be con-15 trolled, the separate or joint application of the compounds I and II or of the mixtures of the compounds I and II is carried out by spraying or dusting the seeds, the plants or the soil before or -after sowing of the plants or before or after emergence of the -~
plants.
The fungicidal synergistic mixtures according to the invention and the compounds I and II can be prepared, for example, in the form of directly sprayable solutions, powder~ and ~uspensions or in the form of high-percentage aqueous, oily or other suspen-25 sions, dispersions, emulsions, oil dispersions, pastes, dustingcompositions, brcadcasting compositions or granules and applied by spraying, atomizing, dusting, broadcasting or watering. The application form is dependent on the intended use; it should in each case guarantee a dispersion of the mixture according to the 30 invention which i8 as fine and uniform as possible.
The formulations are prepared in a manner known per se, eg. by addition of solvents and/or carriers. Inert additives such as emulsifiers or dispersants are customarily admixed to the 35 formulations.
Suitable surface-active substances are the alkali metal, alkaline earth metal or ammonium salts of aromatic sulfonic acids, eg.
lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid 40 and dibutylnaphthalene~ulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation prod-ucts of sulfonated naphthalene and its derivatives with formalde-45 hyde, condensation products of naphthalene or of naphthalenesul-fonic acids with phenol and formaldehyde, polyoxyethylene octyl-- phenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, - ..
;,.: ' . :- - ~ : .
~ ' ' ' BASF Aktienge~ellschaft 931555 0.Z. 0050/44323 2132D~
alkylphenol or tributylphenyl polyglycol ethers, alkylaryl poly-ether alcohols, i otridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxy-propylene alkyl ethers, lauryl alcohol polyglycol ether acetate, 5 sorbitol-esters, lignin-sulfite waste liquors or methylcellulose.
Powder, broadcasting and dusting compositions can be prepared by mixing or joint grinding of the compounds I or II or the mixture of the compounds I and II with a solid carrier.
Granules (eg. coated, impregnated or homogeneous granules) are customarily prepared by binding the active compound or the active compounds to a solid carrier.
lS Fillers or solid carriers used are, for example, mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, lime-stone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastic~, and fertilizers such as ammonium sulfate, ammonium 20 phosphate, ammonium nitrate, ureas and vegetable products such a cereal flour, tree bark meal, wood meal and nutshell meal, cellu-lose powder or other solid carriers.
The formulations in general contain from 0.1 to 95 % by weight, 25 preferably from 0.5 to 90 % by weight, of one of the compounds I
or II or the mixture of the compounds I and II. The active com-pounds are in this case employed in a purity of from 90 % to 100 %, preferably from 95 ~ to 100 % (according to NMR spectrum or HPLC).
The compounds I or II and the mixtures or the corresponding for-mulations are applied by treating the harmful fungi or the plants, seeds, 80ils, surfaces, materials or space~ to be kept free from them with a fungicidally active amount of the mixture, -~
35 or of the compounds I and II in the case of separate application.
Application can be carried out before or after attack by the harmful fungi.
Examples of the synergistic action of the mixtures according to ~ 40 the invention against harmful fungi.
It was possible to show the fungicidal action of the compounds and of the mixtures by the following tests:
45 The active compounds were prepared separately or jointly as a 20%
strength emulsion in a mixture of 70% by weight of cyclohex-anone, 20% by weight of Nekanil~ L~ (Lutensol~ AP6, wetting agent ",,.~ . . :. .... .~ , : - : .
.,:
:........... .
.-, . ~ . :: : .: : :
BASF Aktiengesellschaft 931555 O.Z. 0050/44323 , 2132048 having emulsifier and dispersant action based on ethoxylated al-kylphenols) and 10% by weight of Emulphor~ EL (Emulan~ EL, emul-sifier based on ethoxylated fatty alcohols) and accordingly diluted to the desired concentration with water.
Assessment fo~lowed determination of the attacked leaf areas in percent. These percentage values were converted into degrees of action. The degrees of action of the active compound mixtures to be expected were determined according to the Colby formula lO [R.S. Colby, Weeds 15, (1967) 20-22] and compared with the de-grees of action observed.
Colby formula:
E = x + y - x X y/100 E is the degree of action to be expected, expressed in ~ of the untreated control, when using the mi~ture of the active compounds A and B in the concentrations a and b x is the degree of action, expressed in ~ of the untreated control, when using the active compound A in the concentration a 25 y is the degree of action, expressed in % of the untreated control, when using the active compound ~ in the concentration b At a degree of action of 0, the attack of the treated plants cor-30 responds to that of the untreated control plants; at a degree of action of 100 the treated plants showed no attack.
Activity against Fusarium culmorum on wheat 35 Primary leaves of wheat of the variety Kanzler which has been grown in pots were sprayed until dripping wet with aqueous spray liquor which contained 80% of active compound and 20% of emulsi-fier in the dry matter. On the following day, they were inocu-lated with a spore suspension of Fuisarium culmorum and then ~ 40 placed in a climatic chamber having high atmospheric humidity (> 90~) at 22-24-C. After 6 days, the extent of symptom develop-ment was asses~ed visually.
, . .
.~
BASF Aktiengesellschaft 931555 O.Z. 0050/44323 2~320~8 Active compound Active compound con- Degree of action in centration in the ~ of the untreated spray liquor in ppm control Control (untreated) _ 0 5 I. - 750 41 .
_ II. 750 0 _ _ _ 10 Mixture according to degree of action degree of action the invention observed calculated*) I + II 750 + 750 61 41 1:1 mixture I + II 500 + 500 41 21 15 1:1 mixture I + II 750 + 75 41 21 10:1 mixture _ .
I + II 75 + 750 41 21 1:10 mixture .
Active compound Active compound con- Degree of action in centration in the % of the untreated : :
spray liquor in ppm control :-~
_ _ Control (untreated) _ 0 ::~
_ I. 500 21 25 III. 500 0 Mixture according to degree of action degree of action the invention observed calculated*) ~:
_ I + III 500 + 500 41 21 ~:~
1:1 mixture I + III 500 + 50 41 21 10:1 mixture I + III 50 + 500 68 1:10 mixture _ 35 *) calculated by the Colby formula From the results of the test it emerges that the degree of action observed in all mixture ratios is higher than the degree of action forecast by the Colby formula.
~- . . . : -q. .. .
.: . . :
.. . . .
.; ; ~
~'"'~ .
Fungicidal mixtures The present invention relates to a fungicidal mixture which con-5 tains a) the oxime ether carboxamide of the formula I
C=NOCH3 and b) a dithiocarbamate (II) selected from the group - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and - zinc ethylenebis(dithiocarbamate) (IId) 25 in a synergistically active amount.
The invention additionally relates to processes for controlling harmful fungi using mixtures of the compounds I and II and the use of the compound I and the compounds II for the production of 30 mixtures of this type.
The compound of the formula I, its preparation and its action against harmful fungi are disclosed in the literature (EP-A 477 631).
The dithiocarbamates II (IIa: common name: mancozeb, US-A 3,379,610; IIb: common name: maneb, US-A 2,504,404; IIc:
former common name: metiram, US-A 3,248,400; IId: common name:
zineb, US-A 2,457,674), their preparation and their action 40 against harmful fungi are likewise known.
With respect to a decrease in the application rates and an im-provement of the spectrum of action of known compound3, the pres-ent invention is based on mixtures which, with a reduced total 45 amount of applied active compo~nds, have an improved action -against harmful fungi (synergistic mixtures).
- . , . , - : . ~ ,, , . , :
BASF Aktiengesellschaft 931555 0.Z. 0050/44323 21320~8 Accordingly, the mixtures defined at the beginning have been found. It has-additionally been found that on simultaneous joint or separate application of the compound I and the compounds II or on application of the compound I and the compounds II in succes-5 sion, harmful fungi can be controlled better than with the indi-vidual compounds.
The compound of the formula I can be present in the E or the Z
configuration with respect to the C=X double bond (with respect 10 to the carboxylic acid function group). Accordingly, it can be used in the mixture according to the invention in each case ei-ther as the pure ~ or Z isomer or as an ~/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, the E iso-mer being particularly preferred.
~ecause of the basic character of the NH group, the compound I is ab~e to form salts or adducts with inorganic or organic acids or with metal ions.
20 ~xamples of inorganic acids are hydrohalic acids such as hydro-fluoric acid, hydrochloric acid, hydrobromic acid and hydriodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carbonic 25 acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals 30 having 1 to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such a~ phenyl and naphthyl which carry one or two sulfonic acid groups), alkylphosphonic acids (phos-phonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or -diphos-~5 phonic acids (aromatic radicals ~uch as phenyl and naphthyl whichcarry one or two phosphoric acid radicals), the alkyl and aryl radicals being able to carry further substituents, eg. p-toluene-sulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxy-benzoic acid, 2-acetoxybenzoic acid etc.
Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, as well as of the first to eighth subgroup, in particular 45 chromium, manganese, iron, cobalt, nickel, copper, zinc and oth-ers. The metal ions of the elements of the subgroups of the fourth period are particularly preferred. The metals can in this ., : : . , .
': ' '' ' ' , ': ' - ~ ' .
- :
.,~" - "
~ .
;:- . , BASF Aktiengesellschaft 931555 O.Z. 0050/44323 21320~
case be present in the different valencies applicable to them.
Preferably, the pure active compounds I and II are employed in the preparation of the mixtures, to which, if required, further 5 active compounds against harmful fungi or other pests such as in-sects, arachnids or nematodes, or alternatively herbicidal or growth-regulating active compounds or fertilizers, can be ad-mixed.
10 The mixtures of the compounds I and II and the simultaneous joint or separate use of the compounds I and II are distinguished by an outstanding action against a wide spectrum of phytopathogenic fungi, in particular from the Ascomycetes and Basidiomycetes class. In some cases they are systemically active and can there-15 fore also be employed as foliar and soil fungicides.
They have particular importance for the control of a multiplicityof fungi on various crop plants such as cotton, vegetable plants (eg. cucumbers, beans and cucurbit~), barley, grass, oats, cof-20 fee, maize, fruit plants, rice, rye, soybean, grape, wheat, deco-rative plants, sugar cane and a multiplicity of seeds.
In particular, they are suitable for the control of the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on ce-25 reals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cu-curbits, Podosphaera leucotricha on apples, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago spe-cies on cereals and sugar cane, Venturia inaequalis (scab) on ap-ples, Helminthosporium species on cereals, Septoria nodorum on 30 wheat, Botrytis cinerea (gray mold) on strawberries and vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpo-trichoides on wheat and barley, Pyricularia oryzae on rice, Phy-tophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Alternaria species on vegetables and fruit and also Fu-35 sarium and Verticillium species.
They are additionally applicable in the protection of materials ;~
(eg. wood preservation), for example against Paecilomyces variotii.
The compounds I and II can be applied ~imultaneously ~ointly or separately, or in succession, the sequence in the case of sepa-rate application in general having no effect on the control suc-cess.
The compounds I and II are customarily applied in a weight ratio of from 2000:1 to 5:1, preferably from 1000:1 to 5:1, in BASF Aktienges~llschaft 931555 O.Z. 0050/4g3~3 213~48 particular from 500:1 to 5:1 (II:I).
Depending on the type of effect desired, the application rates of the mixtures according to the invention are from 0.005 to 5 0.5 kg/ha~, preferably from 0.01 to 0.5 kg/ha, in particular from 0.01 to 0.3 kg/ha, for the compound I. The application rates for the compound~ II are correspondingly from 0.1 to 10 kg/ha, pre-rerably from 0.5 to 5 kg/ha, in particular from 1 to 4 kg/ha.
10 In the treatment of seed, application rateQ of mixture of from 0.001 to 100 g/kg of seed, preferably from 0.01 to 50 g/kg, in particular from 0.01 to 10 g/kg, are generally used.
If harmful fungi which are pathogenic for plants are to be con-15 trolled, the separate or joint application of the compounds I and II or of the mixtures of the compounds I and II is carried out by spraying or dusting the seeds, the plants or the soil before or -after sowing of the plants or before or after emergence of the -~
plants.
The fungicidal synergistic mixtures according to the invention and the compounds I and II can be prepared, for example, in the form of directly sprayable solutions, powder~ and ~uspensions or in the form of high-percentage aqueous, oily or other suspen-25 sions, dispersions, emulsions, oil dispersions, pastes, dustingcompositions, brcadcasting compositions or granules and applied by spraying, atomizing, dusting, broadcasting or watering. The application form is dependent on the intended use; it should in each case guarantee a dispersion of the mixture according to the 30 invention which i8 as fine and uniform as possible.
The formulations are prepared in a manner known per se, eg. by addition of solvents and/or carriers. Inert additives such as emulsifiers or dispersants are customarily admixed to the 35 formulations.
Suitable surface-active substances are the alkali metal, alkaline earth metal or ammonium salts of aromatic sulfonic acids, eg.
lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid 40 and dibutylnaphthalene~ulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation prod-ucts of sulfonated naphthalene and its derivatives with formalde-45 hyde, condensation products of naphthalene or of naphthalenesul-fonic acids with phenol and formaldehyde, polyoxyethylene octyl-- phenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, - ..
;,.: ' . :- - ~ : .
~ ' ' ' BASF Aktienge~ellschaft 931555 0.Z. 0050/44323 2132D~
alkylphenol or tributylphenyl polyglycol ethers, alkylaryl poly-ether alcohols, i otridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxy-propylene alkyl ethers, lauryl alcohol polyglycol ether acetate, 5 sorbitol-esters, lignin-sulfite waste liquors or methylcellulose.
Powder, broadcasting and dusting compositions can be prepared by mixing or joint grinding of the compounds I or II or the mixture of the compounds I and II with a solid carrier.
Granules (eg. coated, impregnated or homogeneous granules) are customarily prepared by binding the active compound or the active compounds to a solid carrier.
lS Fillers or solid carriers used are, for example, mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, lime-stone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastic~, and fertilizers such as ammonium sulfate, ammonium 20 phosphate, ammonium nitrate, ureas and vegetable products such a cereal flour, tree bark meal, wood meal and nutshell meal, cellu-lose powder or other solid carriers.
The formulations in general contain from 0.1 to 95 % by weight, 25 preferably from 0.5 to 90 % by weight, of one of the compounds I
or II or the mixture of the compounds I and II. The active com-pounds are in this case employed in a purity of from 90 % to 100 %, preferably from 95 ~ to 100 % (according to NMR spectrum or HPLC).
The compounds I or II and the mixtures or the corresponding for-mulations are applied by treating the harmful fungi or the plants, seeds, 80ils, surfaces, materials or space~ to be kept free from them with a fungicidally active amount of the mixture, -~
35 or of the compounds I and II in the case of separate application.
Application can be carried out before or after attack by the harmful fungi.
Examples of the synergistic action of the mixtures according to ~ 40 the invention against harmful fungi.
It was possible to show the fungicidal action of the compounds and of the mixtures by the following tests:
45 The active compounds were prepared separately or jointly as a 20%
strength emulsion in a mixture of 70% by weight of cyclohex-anone, 20% by weight of Nekanil~ L~ (Lutensol~ AP6, wetting agent ",,.~ . . :. .... .~ , : - : .
.,:
:........... .
.-, . ~ . :: : .: : :
BASF Aktiengesellschaft 931555 O.Z. 0050/44323 , 2132048 having emulsifier and dispersant action based on ethoxylated al-kylphenols) and 10% by weight of Emulphor~ EL (Emulan~ EL, emul-sifier based on ethoxylated fatty alcohols) and accordingly diluted to the desired concentration with water.
Assessment fo~lowed determination of the attacked leaf areas in percent. These percentage values were converted into degrees of action. The degrees of action of the active compound mixtures to be expected were determined according to the Colby formula lO [R.S. Colby, Weeds 15, (1967) 20-22] and compared with the de-grees of action observed.
Colby formula:
E = x + y - x X y/100 E is the degree of action to be expected, expressed in ~ of the untreated control, when using the mi~ture of the active compounds A and B in the concentrations a and b x is the degree of action, expressed in ~ of the untreated control, when using the active compound A in the concentration a 25 y is the degree of action, expressed in % of the untreated control, when using the active compound ~ in the concentration b At a degree of action of 0, the attack of the treated plants cor-30 responds to that of the untreated control plants; at a degree of action of 100 the treated plants showed no attack.
Activity against Fusarium culmorum on wheat 35 Primary leaves of wheat of the variety Kanzler which has been grown in pots were sprayed until dripping wet with aqueous spray liquor which contained 80% of active compound and 20% of emulsi-fier in the dry matter. On the following day, they were inocu-lated with a spore suspension of Fuisarium culmorum and then ~ 40 placed in a climatic chamber having high atmospheric humidity (> 90~) at 22-24-C. After 6 days, the extent of symptom develop-ment was asses~ed visually.
, . .
.~
BASF Aktiengesellschaft 931555 O.Z. 0050/44323 2~320~8 Active compound Active compound con- Degree of action in centration in the ~ of the untreated spray liquor in ppm control Control (untreated) _ 0 5 I. - 750 41 .
_ II. 750 0 _ _ _ 10 Mixture according to degree of action degree of action the invention observed calculated*) I + II 750 + 750 61 41 1:1 mixture I + II 500 + 500 41 21 15 1:1 mixture I + II 750 + 75 41 21 10:1 mixture _ .
I + II 75 + 750 41 21 1:10 mixture .
Active compound Active compound con- Degree of action in centration in the % of the untreated : :
spray liquor in ppm control :-~
_ _ Control (untreated) _ 0 ::~
_ I. 500 21 25 III. 500 0 Mixture according to degree of action degree of action the invention observed calculated*) ~:
_ I + III 500 + 500 41 21 ~:~
1:1 mixture I + III 500 + 50 41 21 10:1 mixture I + III 50 + 500 68 1:10 mixture _ 35 *) calculated by the Colby formula From the results of the test it emerges that the degree of action observed in all mixture ratios is higher than the degree of action forecast by the Colby formula.
~- . . . : -q. .. .
.: . . :
.. . . .
.; ; ~
~'"'~ .
Claims (12)
1. A fungicidal mixture containing a) the oxime ether carboxamide of the formula I
and b) a dithiocarbamate (II) selected from the group - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and - zinc ethylenebis(dithiocarbamate) (IId) in a synergistically active amount.
and b) a dithiocarbamate (II) selected from the group - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and - zinc ethylenebis(dithiocarbamate) (IId) in a synergistically active amount.
2. A fungicidal mixture as claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and manganese ethylenebis(dithiocarbamate) (zinc com-plex) (IIa).
3. A fungicidal mixture as claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and manganese ethylenebis(dithiocarbamate) (IIb).
4. A fungicidal mixture a claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and zinc ammoniate ethylenebis(dithiocarba-mate) (IIc).
5. A fungicidal mixture as claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and zinc ethylenebis(dithiocarbamate) (IId).
6. A fungicidal mixture as claimed in claim 1, wherein the weight ratio of the compound II to the compound I is from 2000:1 to 5:1.
7. A process for controlling harmful fungi, which comprises treating the harmful fungi, their environment or the plants, seeds, soils, surfaces, materials or spaces to be kept free from them with the compound of the formula I as claimed in claim-1 and the compound of the formula II as claimed in claim 1.
8. A process as claimed in claim 7, wherein the compound I as claimed in claim 1 and the compound II as claimed in claim 1 are applied simultaneously jointly or separately, or in suc-cession.
9. A process as claimed in claim 7, wherein the harmful fungi, their environment or the plants, seeds, soils, surfaces, ma-terials or spaces to be kept free from them are treated with from 0.005 to 0.5 kg/ha of the compound I as claimed in claim 1.
10. A process as claimed in claim 7, wherein the harmful fungi, their environment or the plants, seeds, soils, surfaces, ma-terials or spaces to be kept free from them are treated with from 0.1 to 10 kg/ha of a compound II as claimed in claim 1.
11. A method of using the compound I as claimed in claim 1 for the production of fungicidally active synergistic mixtures as claimed in claim 1.
12. A method of using a compound II as claimed in claim 1 for the production of fungicidally active synergistic mixtures as claimed in claim 1.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4332569 | 1993-09-24 | ||
DEP4332569.6 | 1993-09-24 | ||
DE4406645 | 1994-03-01 | ||
DEP4406645.7 | 1994-03-01 | ||
US08/364,930 US5504110A (en) | 1993-09-24 | 1994-12-28 | Fungicidal mixtures |
CN95101893.0A CN1126029A (en) | 1993-09-24 | 1995-01-03 | Fungicidal mixtures |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2132048A1 true CA2132048A1 (en) | 1995-03-25 |
Family
ID=37101996
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002132048A Abandoned CA2132048A1 (en) | 1993-09-24 | 1994-09-14 | Fungicidal mixtures |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP3630724B2 (en) |
CN (2) | CN1111090A (en) |
CA (1) | CA2132048A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997006683A1 (en) * | 1995-08-17 | 1997-02-27 | Basf Aktiengesellschaft | Fungicidal mixtures of an oxime ether carboxylic acid amide with a dithiocarbamate |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100352347C (en) * | 2003-06-10 | 2007-12-05 | 沈阳化工研究院 | Bactericidal compositions containing enostroburin and thiocarbamate |
-
1994
- 1994-09-14 CA CA002132048A patent/CA2132048A1/en not_active Abandoned
- 1994-09-16 JP JP22182794A patent/JP3630724B2/en not_active Expired - Fee Related
- 1994-09-24 CN CN94116391.1A patent/CN1111090A/en active Pending
-
1995
- 1995-01-03 CN CN95101893.0A patent/CN1126029A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997006683A1 (en) * | 1995-08-17 | 1997-02-27 | Basf Aktiengesellschaft | Fungicidal mixtures of an oxime ether carboxylic acid amide with a dithiocarbamate |
US5939454A (en) * | 1995-08-17 | 1999-08-17 | Basf Akdtiengesellschaft | Fungicidal mixtures of an oxime ether carboxylic acit amide with a dithiocarbamate |
Also Published As
Publication number | Publication date |
---|---|
JP3630724B2 (en) | 2005-03-23 |
CN1111090A (en) | 1995-11-08 |
CN1126029A (en) | 1996-07-10 |
JPH07165509A (en) | 1995-06-27 |
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Legal Events
Date | Code | Title | Description |
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FZDE | Discontinued |