AU2006201613A1 - Stable fungicide compositions - Google Patents
Stable fungicide compositions Download PDFInfo
- Publication number
- AU2006201613A1 AU2006201613A1 AU2006201613A AU2006201613A AU2006201613A1 AU 2006201613 A1 AU2006201613 A1 AU 2006201613A1 AU 2006201613 A AU2006201613 A AU 2006201613A AU 2006201613 A AU2006201613 A AU 2006201613A AU 2006201613 A1 AU2006201613 A1 AU 2006201613A1
- Authority
- AU
- Australia
- Prior art keywords
- composition
- formulation
- oil
- dithiocarbamate
- triazole
- 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 description 127
- 230000000855 fungicidal effect Effects 0.000 title claims description 33
- 239000000417 fungicide Substances 0.000 title description 21
- 238000009472 formulation Methods 0.000 claims description 81
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 46
- 229920000642 polymer Polymers 0.000 claims description 40
- 239000012990 dithiocarbamate Substances 0.000 claims description 33
- 150000003852 triazoles Chemical class 0.000 claims description 32
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 28
- 229930182692 Strobilurin Natural products 0.000 claims description 26
- 239000007921 spray Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 10
- -1 pyradostrobin Chemical compound 0.000 claims description 10
- 239000005802 Mancozeb Substances 0.000 claims description 7
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 claims description 4
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 claims description 4
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 claims description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 239000004308 thiabendazole Substances 0.000 claims description 3
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 3
- 235000010296 thiabendazole Nutrition 0.000 claims description 3
- 229960004546 thiabendazole Drugs 0.000 claims description 3
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical group C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 claims description 2
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 claims description 2
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 claims description 2
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims description 2
- TTXSXEZBTCFTQU-UHFFFAOYSA-N 1,2,4,7-dithiadiazocane-3,8-dithione Chemical compound S=C1NCCNC(=S)SS1 TTXSXEZBTCFTQU-UHFFFAOYSA-N 0.000 claims description 2
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 claims description 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 2
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 claims description 2
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 claims description 2
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 claims description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims description 2
- YABFPHSQTSFWQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(O)(C[Si](C)(C)C)CN1C=NC=N1 YABFPHSQTSFWQB-UHFFFAOYSA-N 0.000 claims description 2
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims description 2
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 claims description 2
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 claims description 2
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000005730 Azoxystrobin Substances 0.000 claims description 2
- 239000005741 Bromuconazole Substances 0.000 claims description 2
- 239000005757 Cyproconazole Substances 0.000 claims description 2
- 239000005760 Difenoconazole Substances 0.000 claims description 2
- 239000005761 Dimethomorph Substances 0.000 claims description 2
- 239000005762 Dimoxystrobin Substances 0.000 claims description 2
- 239000005765 Dodemorph Substances 0.000 claims description 2
- 239000005767 Epoxiconazole Substances 0.000 claims description 2
- 239000005772 Famoxadone Substances 0.000 claims description 2
- 239000005775 Fenbuconazole Substances 0.000 claims description 2
- 239000005778 Fenpropimorph Substances 0.000 claims description 2
- 239000005784 Fluoxastrobin Substances 0.000 claims description 2
- 239000005785 Fluquinconazole Substances 0.000 claims description 2
- 239000005787 Flutriafol Substances 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 239000005796 Ipconazole Substances 0.000 claims description 2
- 239000005800 Kresoxim-methyl Substances 0.000 claims description 2
- 239000005868 Metconazole Substances 0.000 claims description 2
- 239000005809 Metiram Substances 0.000 claims description 2
- 239000005811 Myclobutanil Substances 0.000 claims description 2
- 239000005813 Penconazole Substances 0.000 claims description 2
- 239000005818 Picoxystrobin Substances 0.000 claims description 2
- 229920002873 Polyethylenimine Polymers 0.000 claims description 2
- 239000005822 Propiconazole Substances 0.000 claims description 2
- 239000005823 Propineb Substances 0.000 claims description 2
- 239000005825 Prothioconazole Substances 0.000 claims description 2
- 239000005869 Pyraclostrobin Substances 0.000 claims description 2
- 239000005839 Tebuconazole Substances 0.000 claims description 2
- 239000005840 Tetraconazole Substances 0.000 claims description 2
- 239000005843 Thiram Substances 0.000 claims description 2
- 239000005846 Triadimenol Substances 0.000 claims description 2
- 239000005857 Trifloxystrobin Substances 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 239000005859 Triticonazole Substances 0.000 claims description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 claims description 2
- 229950000294 azaconazole Drugs 0.000 claims description 2
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 2
- HJJVPARKXDDIQD-UHFFFAOYSA-N bromuconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCC(Br)C1 HJJVPARKXDDIQD-UHFFFAOYSA-N 0.000 claims description 2
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 2
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 claims description 2
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 claims description 2
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 claims description 2
- VMNULHCTRPXWFJ-UJSVPXBISA-N enoxastrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)\C=C\C1=CC=C(Cl)C=C1 VMNULHCTRPXWFJ-UJSVPXBISA-N 0.000 claims description 2
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 claims description 2
- AWYFNIZYMPNGAI-UHFFFAOYSA-L ethylenebis(dithiocarbamate) Chemical compound [S-]C(=S)NCCNC([S-])=S AWYFNIZYMPNGAI-UHFFFAOYSA-L 0.000 claims description 2
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 claims description 2
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- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 claims description 2
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- AGKSTYPVMZODRV-UHFFFAOYSA-N imibenconazole Chemical compound C1=CC(Cl)=CC=C1CSC(CN1N=CN=C1)=NC1=CC=C(Cl)C=C1Cl AGKSTYPVMZODRV-UHFFFAOYSA-N 0.000 claims description 2
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 claims description 2
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 claims description 2
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- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 claims description 2
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- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 2
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims description 2
- 229960002447 thiram Drugs 0.000 claims description 2
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 claims description 2
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 claims description 2
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-MDZDMXLPSA-N trans-Brassidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-MDZDMXLPSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 150000003679 valine derivatives Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
P/00/011 Regulation 3.2
AUSTRALIA
Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Invention Title: Stable fungicide compositions The following statement is a full description of this invention, including the best method of performing it known to us: 63,615A STABLE FUNGICIDE COMPOSITIONS The present invention relates to fungicide compositions comprising dithiocarbamates, triazoles, morpholines and/or strobilurins.
Dithiocarbamates are known as preventative fungicides useful in the prevention of phytopathogenic fungi and are typically dispersed, or otherwise mixed into liquids to form slurries or concentrates, such as aqueous flowable formulations, oil dispersions, or other mixtures for use in agricultural sprays.
Triazoles, morpholines, and strobilurins are known as curative fungicides useful in the control of phytopathogenic fungi and are typically dispersed, dissolved or otherwise mixed into liquids to form solutions or suspension concentrates, such as aqueous flowable formulations, oil dispersions, emulsifiable concentrates, or other mixtures for use in agricultural sprays.
Agricultural sprays require high affinity for absorption into the foliage, while maintaining a high degree of rain fastness, particularly in tropical regions.
The term 'rain fastness' refers to the ability of the agricultural spray to remain in contact with the leaf, without being washed away by rain. A number of additives have been investigated to improve the efficacy of aqueous sprays containing fungicide formulations. For example, French Patent 1493069 discloses the use of polyvinyl alcohol (PVA) to increase the affinity of a fungicide for foliage, while Canadian patent 1,328,599 discloses the use of PVA to increase rain fastness.
Additionally, other water soluble polymers have been combined with fungicides in aqueous formulations such as those taught in EP 245,970, GB 1,209,996 and GB 1,056,887. However, in tropical regions where rain proliferates, it is difficult for aqueous formulations to be effective.
Fungicide oil dispersions have also been used in order to increase the rain fastness of such agricultural sprays. However, oil dispersions can be difficult to stabilize, due to fungicide settling, agglomeration, or incompatibility of the fungicide formulation with oil. In addition, it is typically desirable to combine -1A- 63,615A preventative and curative fungicides in a single spray application, such as a fungicidal oil dispersion. However, this may cause an additional problem of compatibility between the fungicide formulations and their dispersibility within the oil.
Therefore, there is a need to develop further fungicide formulations and agricultural sprays which will exhibit good rain fastness, good oil dispersion stability and compatibility.
The present invention relates to a fungicidal composition useful in preparing oil dispersed agricultural sprays comprising: 1) at least one fungicidal formulation which comprises a dithiocarbamate, triazole, morpholine or strobilurin compound; and 2) an oil soluble or oil compatible poly fatty acid-imine polymer.
The present invention also relates to a method of compatibilizing a fungicidal formulation for use in preparing an oil dispersed agricultural spray, comprising a dithiocarbamate, triazole, morpholine or strobilurin compound, wherein the method comprises adding an oil soluble or oil compatible poly fatty acid-imine polymer to the formulation.
The present invention additionally relates to a method of controlling and preventing an infestation of phytopathogenic fungi microorganisms in plants, comprising contacting a plant, a part of a plant, or the locus thereof with; or applying to the soil a fungicidal composition comprising: 1) at least one fungicidal formulation which comprises a dithiocarbamate, triazole, morpholine or strobilurin; and 2) an oil soluble or oil compatible poly fatty acid-imine polymer, wherein the formulation and the polymer are dispersed in an oil.
The present invention additionally relates to a composition comprising: 63,615A 1) a) a dithiocarbamate formulation, and b) a triazole, morpholine or strobilurin formulation, and 2) an oil soluble or oil compatible poly fatty acid-imine polymer, wherein the formulations and polymer are dispersed in an oil.
It has been discovered that the use of an oil soluble or oil compatible poly fatty acid-imine polymer in the fungicidal formulations described, improves the dispersion, stability and compatibility of the dithiocarbamate, triazole, morpholine and strobilurin formulations in oil.
The dithiocarbamate useful for the present invention can be any dithiocarbamate having fungicidal activity and is preferably selected from alkylene bisdithiocarbamate metal salts. Preferred ethylenebisdithiocarbamate metal salts are mancozeb (a coordination product of zinc and manganese ethylene bisdithiocarbamate), maneb (manganese ethylenebisdithiocarbamate) and zineb (zinc ethylene-bisdithiocarbamate). A preferred dimethyldithiocarbamate metal salt is ziram (zinc dimethyldithiocarbamate). A preferred propylenebisdithiocarbamate metal salt is propineb ([[1-methyl-l,2-ethanediyl)bis- [carbamatothioato]](2-)]zinc homopolymer). Another preferred dithiocarbamate is metiram )(tris[amine-[ethylene bis(dithiocarbamate)]zinc(II)[tetrahydro-1,2,4,7dithiadia-zocine-3,8-dithione]polymer). Ferbam (ferric dimethyldithiocarbamate), metham (sodium N-methyldithiocarbamate), and thiram (bis(dimethylthiocarbamoyl)disulfide). The dithiocarbamate compound is typically in the form of a formulation such as a wettable powder, dust, granule, non-aqueous oil flowable concentrate or oil dispersed suspension concentrate formulation. Such formulations are well known in the art and commercially available. Preferred formulations include oil flowable concentrates or oil dispersed suspensions. The concentration of the dithiocarbamate compound in the formulation is typically 63,615A from 20 percent to 95 percent by weight, based on the total weight of the formulation. For example, a wettable powder or granular formulation may contain from 50 to 95 weight percent dithiocarbamate compound, wherein an oil suspension concentrate typically contains from 20 to 55 weight percent.
Representative triazoles useful in the present invention include any triazole which shows fungicidal activity including epoxiconazole, propiconazole, tebuconazole, flusilazole, cyproconazole, hexaconazole, triadimefon, metconazole, fluquinconazole, triticonazole, flutriafol, bromuconazole, diniconazole, prothioconazole, difenoconazole, triadimenol, myclobutanil, penconazole, bitertanol, tetraconazole, fenbuconazole, imibenconazole, ipconazole, etaconazole, simeconazole, azaconazole, thiabendazole and diclobutrazol and the like.
Typical morpholines useful in the present invention include any morpholine which has fungicidal activity, including tridemorph, fenpropimorph, dodemorph, dimethomorph and the like.
The strobilurins which are useful in the present invention, include any strobilurin which has fungicidal activity, including azoxystrobin, picoxystrobin, enestroburin, pyradostrobin, fluoxastrobin, metominostrobin, trifloxystrobin, dimoxystrobin, famoxadone, pyraclostrobin, kresoxim-methyl, and the like.
Triazole, morpholine and strobilurin formulations are typically formulated as emulsifiable concentrates, soluble liquids, granules, solutions, suspension concentrates, wettable powders, dusts or oil dispersed concentrates, and the like.
Such formulations are well known in the art and are commercially available.
Preferred formulations are emulsifiable concentrates and suspension concentrates.
The formulation may be any useable concentration and typically contains from percent to 95 percent by weight, of the triazole, morpholine or strobilurin compound, based on the total weight of the formulation.
63,615A An oil soluble or compatible polymer is combined with the fungicidal formulation in order to increase the dispersibility and act as a compatibilizer for the formulation when used in oil dispersions. Such polymers include copolymers of imines and fatty acids, e.g. poly fatty acid-imine polymers. Such copolymers can be produced from fatty acid and imine monomers as described in U.S.
2,852,467, which is incorporated herein by reference. Typical fatty acids include, but are not limited to hydroxy fatty acids, saturated, monounsaturated, diunsaturated, triunsaturated and tetraunsaturated C 4 -C22 fatty acids, such as 3methylbutanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, onanoic acid, decanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, eicosanoic acid; 3,7,11,15-tetramethyl-hexadecanoic acid; docosanoic acid, tetracosanoic acid, hexacosanoic acid, octacosanoic acid, 9-decenoic acid, cis-9-hexadecenoic acid, cis-9-octadecanoic acid, trans-11-octadecenoic acid, trans-9-octadecanoic acid, trans-13-docosenoic acid, cis-13-docosenoic acid, cis-15-tetracosenoic acid; cis,cis-9,12-octadecadienoic acid; cis, trans, trans-9,11,13-octadecatrienoic acid; cis,cis,cis-9,12,15-octadecatrienoic acid; 5,8,11,14-eicosatetraenoic acid, 12hydroxy octadecanoic acid and the like. Suitable imines include polyalkyleneimines, such as polyethyleneimine. In general, the polymer can be any polymer as described above which will adequately suspend the dithiocarbamate, triazole, morpholine or strobilurin in oil and prevent agglomeration. The polymer is utilized in an amount which satisfactorily stabilizes and compatibilizes the fungicide formulation within the oil dispersion composition.
It should be noted that the oil dispersion described herein is non-aqueous in that water is not present beyond what would normally be acceptable due to moisture content or humidity influence. Therefore, the amount of water present within the oil dispersion will be less than 1 wt. percent, preferably less than 63,615A wt. percent and more preferably less than 0.1 wt. percent based on the total weight of the oil dispersion.
The fungicide formulations most useful for the composition of the present invention are typically in the form of concentrates which are further diluted at the point of application. In one embodiment, particularly in tropical regions during rainy season, farmers will mix the desired fungicidal concentrate formulation(s) in a tank with an additional diluent, such as an oil (to increase rain fastness) in proportions such that the fungicidal formulations are applied at the desired level of active ingredient per hectare (g ai/h). The oil diluent can be used in any amount which aids in adequately diluting the desired formulation and the amount of oil is variable depending upon the final application and application rate desired.
Typically, the amount of diluent, e.g. oil, will be from 50 to 99 volume percent, based on the total volume of the agricultural spray. In general, dithiocarbamate formulations can be applied using volume dilution ratios of from 1:1 to 1:100 (dithiocarbamate formulation to diluent), while triazole, morpholine and strobilurin formulations can be applied using volume dilution ratios of from 1:10 to 1:200 (formulation to diluent).
The diluent useful in the present invention can be any organic liquid which is not miscible with water. Typical diluents include oils such as petroleum fractions or hydrocarbons such as mineral oil, dodecylbenzene, paraffinic oils, spindle oil, propylbenzene and the like; vegetable oils such as soy oil, rape seed oil, olive oil, castor oil, coconut oil, corn oil, cotton seed oil, linseed oil, mustard oil, palm oil, peanut oil, safflower oil, banana spray oil, sesame oil, soybean oil, tung oil and the like. Preferred oils include mineral oil and paraffinic oils such as BanoleTM, OrchexTM and ProrexTM, Agratex T M SpraytexTM and Sunspray T M oil.
Table I below outlines various fungicidal formulations and agricultural spray compositions. Wt. is based on the total weight of the concentrate or formulation.
63,615A TABLE I Formulation Active ingredient Preferred Polymer (Concentrate) (Wt. percent) Active ingredient (Wt. percent) (Concentrate) (Wt. percent) (Wt. percent) Dithiocarbamate 20-95 30-55 0.2 to Triazole 10-95 20-40 0.2 to Morpholine 10-95 20-95 0.2 to Strobilurin 10-95 20-40 0.2 to Spray Formulation Preferred Polymer Coms (Wt. percent) Formulation (Wt. percent) Compositions percent) Dithiocarbamate 1-30 5-25 0.01-5 (Preferred 0.01-2) Triazole 0.1-10 0.5-5 0.01-5 Morpholine 0.1-10 0.5-5 0.01-5 Strobilurin 0.1-10 0.5-5 0.01-5 Dithiocarbamate 1-30 5-25 0.01-5 Triazole, 0.1-10 0.5-5 Morpholine or Strobilurin The polymer can be added directly to the desired formulation, or alternatively, can be added at a later time, after dilution of the concentrated formulation, to the final spray composition prior to application.
Additional additives, such as surfactants, buffers, dispersants, diluents, suspension agents, solvents, emulsifiers, viscosity reducers, rheology modifiers and the like may also be added to the composition of the present invention.
Alternatively, the compositions of the present invention can be combined with other fungicides or concentrates in order to provide a composition which will adequately provide fungicidal protection when applied to plants, soil or plant loci.
When mixtures of pesticides are employed, the relative proportions which are used will depend upon the relative efficacy of each pesticide in the mixture with respect to the fungi to be controlled. Examples of other fungicides which can be 63,615A combined include, nitrophenol derivatives such as dinocap, binapacryl, and 2-secbutyl-4,6-dinitrophenyl isopropyl carbonate; heterocyclic structures such as captan folpet, glyodine, dithianon, thioquinox, benomyl, thiabendazole, vinolozolin, iprodione, procymidone, fluoroimide, triarimol, cycloheximide, ethirimol, thifluzamide, and quinomethionate; miscellaneous halogenated fungicides such as chloranil, chlorothalonil, dichlone, chloroneb, dichloran, and polychloronitrobenzenes; fungicidal antibiotics such as griseofulvin, kasugamycin and streptomycin; miscellaneous fungicides such as diphenyl sulfone, dodine, methoxyl, 1-thiocyano-2,4-dinitrobenzene, 1 -phenylthiosemicarbazide, thiophanate-methyl, and cymoxanil; as well as acylalanins such as furalaxyl, cyprofuram, ofurace, benalaxyl, and oxadixyl; fluazinam, flumetover, phenylbenzamide derivatives such as those disclosed in EP 578586 Al, amino acid derivatives such as valine derivatives disclosed in EP 550788 Al, methoxyacrylates such as methyl (E)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4yloxy(phenyl)-3-methoxyacrylate; benzo(1,2,3)thiadiazole-7-carbothioic acid Smethylester, propamocarb; imazalil; carbendazim; pyrazophos; fenarimol; fenpiclonil; and pyrimethanil. In addition, insecticides, herbicides and fertilizers can be added to the composition of the present invention, as described in U. S.
6,004,570.
In one embodiment, the present invention is an oil dispersed agricultural spray comprising: 1) from 1 to 30 wt. percent of a dithiocarbamate formulation, or from 0.1 to 10 wt. percent of a triazole formulation, morpholine formulation or strobilurin formulation, and 2) from 0.01 to 5 wt. percent of an oil soluble or oil compatible poly fatty acid-imine polymer, based on the total weight of the spray, 63,615A wherein the formulation and polymer are dispersed in oil.
In another embodiment, the present invention is an agricultural spray comprising: 1) a) from 1 to 30 wt. percent ofa dithiocarbamate formulation, and b) from 0.1-10 wt. percent of a triazole formulation, morpholine formulation or strobilurin formulation, and 2) from 0.01-5 wt. percent of an oil soluble or oil compatible poly fatty acid-imine polymer, based on the total weight of the spray, wherein the formulations and polymer are dispersed in oil.
Another embodiment of the present invention is a method of preparing an oil dispersed agricultural spray comprising: adding an oil soluble or oil compatible poly fatty acid-imine polymer to a component of the oil dispersed agricultural spray; wherein the component is selected from at lease one of the following: a fungicidal formulation comprising a dithiocarbamate, triazole, morpholine or strobilurin compound; or a diluent oil.
It is noted here that all formulations disclosed herein may also consist essentially of the components described, wherein other components which would materially change the composition disclosed would be excluded.
EXAMPLES
The following examples are provided to illustrate the present invention. The examples are not intended to limit the scope of the present invention and they should not be so interpreted.
Examples Procedure I 63,615A The 5 samples of Table I are prepared in glass vials by combining 20 ml of banole oil, 0.67 ml of BaycorTM DC 300 (Bitertanol triazole formulation available from Bayer) and the compatibilizing polymer designated in Table I. The vials are capped and mixed by shaking for approximately 30 seconds. The capped vials are then allowed to stand without further agitation. The vials are then visually inspected immediately and ongoing for more than 2 hours.
TABLE II SAMPLE POLYMER' STABILITY CONCENTRATION (v/v percent) 1* 0 Instant separation into two clear phases 2 2 Dispersed, stable >2 hours 3 1 Dispersed, stable >2 hours 4 0.5 Dispersed, stable >2 hours 0.2 Dispersed, stable >2 hours 'Poly( 12-hydroxy-octadecanoic acid-co-ethyleneimine) CAS# 124578-12-7 *Control Table II shows the effects of the compatibilizing polymer at various concentrations on improving the compatibility of the triazole formulation in banole oil. The composition of the present invention shows significant benefits in emulsifying and dispersing the triazole formulation droplets in oil, as compared to the instant separation which occurs in the absence of compatibilizing polymer.
Examples 6-10 The process of Procedure I is repeated with each sample containing 20 ml Banole oil, 0.67 ml Baycor T M DC300 and 5 ml DithaneTM 35 and the polymer designated in Table II. DithaneTM 35 is a mancozeb product available from Dow Agrosciences. Filming after shaking-flocculation is a measurement of the 63,615A uniformity of the film formed on the vial surface after shaking, with quality assessment ranking of 1 to 5 representing worst (no uniformity) to best (complete uniformity). Settling is measured by the separation of the solid (mancozeb) from the paraffinic oil solvent at the top relative to the total height of the sample liquid (for TABLES III and The visual suspension quality was measured by assessing the homogeneity or amount of flocculation of the dispersion, with qualitative assessment ranking 1 to 5 representing worst (little or no homogeneity) to best (complete homogeneity).
TABLE III Filming after shaking- Settling in height) Visual suspension quality flocculation Sample Polymer 5 15 30 60 5 15 30 60 5 15 30 mi min min min min min min min min min min min n 6* None 0 3 3 3 3 1.5 2.9 2.9 4.4 n/a 3 3.5 7 1.
6 5 5 5 4.5 0 0 0 0 n/a 5 5 8 0.8 5 5 5 5 0 0 0 0 n/a 5 5 9 1 0.4 5 4.5 5 5 0 0 0 0 n/a 5 5 0.16 4 3.5 4 4 0.7 0.7 1.5 1.5 n/a 4.5 5 Poly(12-hydroxy-octadecanoic acid-co-ethyleneimine) CAS# 124578-12-7 *Control Table III shows the effects of compatibilizing polymer at various concentrations of oil tank mix ofBaycor T M and DithaneTM 35. The examples show the benefit in stabilizing the oil tank mix with compatibilizing polymer and preventing dithiocarbamate particles from flocculating in the presence of a triazole formulation.
Examples 11-18 63,615A The process of Procedure I is repeated with the samples containing 19.5 ml Dithane T M 35, 2.6 ml triazole formulation, 77.9 ml banole oil and 0.4 ml compatibilizing polymer'.
The control (12) contains 20ml DithaneTM 35 and 80 ml banole oil.
In these examples the settling was measured qualitatively by the overall performance ranking from 1 to 5 representing worst (fastest) to best (slowest).
TABLE IV Sample Triazole polymer Filming after Settling Visual shaking suspension flocculation quality 11* Baycor T M DC300 available 0 3 3 3 from Bayer (Bitertanoltriazole) 12* None 0 4 2.5 2 13 Baycor T M DC300 available 0.4 5 5 from Bayer(Bitertanoltriazole) 14 SicoTM 250EC available 0.4 5 5 from Syngenta (Difenoconazole-triazole) TiltTM250EC available from 0.4 5 4.5 Novartis (Propiconazoletriazole) 16 FolicurTM 250EW available 0.4 5 5 from Bayer (Tebuconazoletriazole) 17 Calixin T M 86 OL available 0.4 5 5 from BASF (Tridemorphmorpholine) 18 BankitTM 25SC available 0.4 5 5 from Syngenta (Azoxystrobin-strobilurin) tThis is volume/volume based on the amount of formulation in the total composition, not the amount of active ingredient in the total composition.
*Control Table IV shows the effects of the Poly(12-hydroxy-octadecanoic acid-coethyleneimine) in oil tank mixes of DithaneTM 35 with triazole, morpholine or strobilurin formulation products. All examples show excellent stability.
63,615A Examples 19 and Top Separation of Dithane* 35 Samples in Storage Stability Test concentrate formulations were prepared with and without additive polymer and divided into glass containers in equal volumes. The samples were then placed under various storage conditions as described in TABLE V. The settling rates were measured by the separation of the solid (mancozeb) from the paraffinic oil solvent at the top relative to the total height of the sample liquid.
TABLE V TOP SEPARATION, 1 ST 2 MONTHS 3 MONTHS volume MONTH 19)* w/o polymer Sample Room Sample Room 8.42 10.75 10.20 Temp.
Sample 8 0 C 5.15 5.38 7.22 Sample 40 0 C 20.00 18.95 14.29 Sample @54 0 C 22.68 23.40 20.41 w/ 1.42 wt.% polymer l Sample Room Sample Room 3.06 18.75 16.67 Temp.
Sample 8 0 C 2.94 2.97 4.85 Sample 40 0 C 18.82 24.75 19.42 Sample @54 0 C 17.35 30.53 18.00 'Poly(12-hydroxy-octadecanoic acid-co-ethyleneimine) CAS#124578-12-7 *Control Table V shows the settling of DithaneTM 35 samples with and without compatibilizing polymer. This exemplifies the incorporation of polymer into commercial formulations with improved dispersion, homogeneity and uniformity, especially after 1 month, without adverse effects.
-13- As used herein, except where the context requires otherwise, the term "comprise" and variations of the term, such as "comprising", "comprises" and "comprised", are not intended to exclude other additives, components, integers or steps.
Reference to any prior art in the specification is not, and should not be taken as, an acknowledgment or any form of suggestion that this prior art forms part of the common general knowledge in Australia or any other jurisdiction or that this prior art could reasonably be expected to be ascertained, understood and regarded as relevant by a person skilled in the art.
-14-
Claims (18)
1. A composition useful in preparing oil dispersed agricultural sprays comprising: 1) at least one fungicidal formulation which comprises a dithiocarbamate, triazole, morpholine or strobilurin compound; and 2) an oil soluble or oil compatible poly fatty acid-imine polymer.
2. The composition of Claim 1 wherein 1) is a dithiocarbamate formulation.
3. The composition of Claim 2 wherein the dithiocarbamate is selected from mancozeb (a coordination product of zinc and manganese ethylene bisdithiocarbamate), maneb (manganese ethylenebisdithiocarbamate), zineb (zinc ethylene-bisdithiocarbamate), ziram( zinc dimethyldithiocarbamate), propineb ([[1-methyl-1 ,2-ethanediyl)bis[carbamatothioato]](2-)]zinc homopolymer), metiram (tris[amine-[ethylene bis(dithiocarbamate)]zinc(II)[tetrahydro-1,2,4,7- dithiadia-zocine-3,8-dithione]polymer), ferbam (ferric dimethyldithiocarbamate), metham (sodium N-methyldithiocarbamate), and thiram (bis(dimethylthiocarbamoyl)disulfide).
4. The composition of Claim 3 wherein the dithiocarbamate is mancozeb.
5. The composition of Claim 1 wherein 1) is a triazole formulation.
6. The composition of Claim 5 wherein the triazole is selected from epoxiconazole, propiconazole, tebuconazole, flusilazole, cyproconazole, hexaconazole, triadimefon, metconazole, fluquinconazole, triticonazole, flutriafol, bromuconazole, diniconazole, prothioconazole, difenoconazole, triadimenol, myclobutanil, penconazole, bitertanol, tetraconazole, fenbuconazole, imibenconazole, ipconazole, etaconazole, simeconazole, azaconazole, thiabendazole and diclobutrazol.
7. The composition of Claim 1 wherein 1) is a morpholine formulation. '63,615A
8. The composition of Claim 7 wherein the morpholine is selected from fenpropimorph, tridemorph, dimethomorph and dodemorph.
9. The composition of Claim 1 wherein 1) is a strobilurin formulation. The composition of Claim 9 wherein the strobilurin is selected from azoxystrobin, picoxystrobin, enestroburin, pyradostrobin, fluoxastrobin, metominostrobin, trifloxystrobin, dimoxystrobin, famoxadone, pyraclostrobin and kresoxim-methyl.
11. The composition of Claim 1 wherein 1) is a combination of a dithiocarbamate formulation and a triazole, morpholine or strobilurin formulation.
12. The composition of Claim 11 wherein 1) is a combination of a dithiocarbamate formulation and a triazole formulation.
13. The composition of Claim 12 wherein the dithiocarbamate is mancozeb and the triazole is bitertanol.
14. The composition of Claim 11 wherein 1) is a combination of a dithiocarbamate formulation and a morpholine formulation. The composition of Claim 11 wherein 1) is a combination of a dithiocarbamate formulation and a strobilurin formulation.
16. The composition of Claim 1 wherein 2) is the reaction product of a fatty acid with polyethyleneimine.
17. The composition of Claim 16 wherein 2) is poly(12-hydroxy- octadecanoic acid-co-ethyleneimine).
18. A method of preparing an oil dispersed agricultural spray comprising: adding an oil soluble or oil compatible poly fatty acid-imine polymer to a component of the oil dispersed agricultural spray; wherein the component is selected from at least one of the following: a fungicidal formulation comprising a dithiocarbamate, triazole, morpholine or strobilurin compound; or a diluent oil. 63,615A
19. A method of controlling and preventing an infestation of phytopathogeinc fungi microorganisms in plants, comprising contacting a plant, part of a plant, or the locus thereof with; or applying to the soil, the composition of Claim 1. The composition of claim 1 substantially as described herein with references to any one of the examples.
21. The method of claim 18 substantially as described herein with references to any one of the examples. Dow AgroSciences LLC By Freehills Patent Trade Mark Attorneys Registered patent attorneys for the applicant 19 April 2006
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102027956A (en) * | 2011-01-07 | 2011-04-27 | 陕西美邦农药有限公司 | Bactericidal composition containing bitertanol and thiocatbamate |
| CN103704223A (en) * | 2010-12-08 | 2014-04-09 | 陕西美邦农药有限公司 | Bactericidal composition containing tridemorph |
| CN114615888A (en) * | 2019-09-04 | 2022-06-10 | 阿达玛马克西姆有限公司 | Oily liquid fungicidal composition |
| US20220240501A1 (en) * | 2016-05-24 | 2022-08-04 | Adama Makhteshim Ltd. | Oil liquid fungicidal formulation |
-
2006
- 2006-04-19 AU AU2006201613A patent/AU2006201613A1/en not_active Abandoned
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103704223A (en) * | 2010-12-08 | 2014-04-09 | 陕西美邦农药有限公司 | Bactericidal composition containing tridemorph |
| CN102027956A (en) * | 2011-01-07 | 2011-04-27 | 陕西美邦农药有限公司 | Bactericidal composition containing bitertanol and thiocatbamate |
| US20220240501A1 (en) * | 2016-05-24 | 2022-08-04 | Adama Makhteshim Ltd. | Oil liquid fungicidal formulation |
| AU2021282407B2 (en) * | 2016-05-24 | 2024-02-08 | Adama Makhteshim Ltd. | Oil liquid fungicidal formulation |
| US12144342B2 (en) | 2016-05-24 | 2024-11-19 | Adama Makhteshim Ltd. | Oil liquid fungicidal formulation |
| CN114615888A (en) * | 2019-09-04 | 2022-06-10 | 阿达玛马克西姆有限公司 | Oily liquid fungicidal composition |
| US12408670B2 (en) | 2019-09-04 | 2025-09-09 | Adama Makhteshim Ltd. | Oil liquid fungicidal compositions |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |