CA2553255A1 - Fungicide composition comprising an arylamidine derivative and known fungicide compounds - Google Patents
Fungicide composition comprising an arylamidine derivative and known fungicide compounds Download PDFInfo
- Publication number
- CA2553255A1 CA2553255A1 CA002553255A CA2553255A CA2553255A1 CA 2553255 A1 CA2553255 A1 CA 2553255A1 CA 002553255 A CA002553255 A CA 002553255A CA 2553255 A CA2553255 A CA 2553255A CA 2553255 A1 CA2553255 A1 CA 2553255A1
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- Prior art keywords
- cndot
- alkyl
- compound
- methyl
- alkoxy
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 150000001875 compounds Chemical class 0.000 title claims abstract description 79
- 239000000417 fungicide Substances 0.000 title claims abstract description 65
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000005825 Prothioconazole Substances 0.000 claims abstract description 17
- 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 abstract description 16
- 239000005784 Fluoxastrobin Substances 0.000 claims abstract description 8
- 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 abstract description 8
- 201000010099 disease Diseases 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 241000196324 Embryophyta Species 0.000 claims description 31
- 150000001356 alkyl thiols Chemical group 0.000 claims description 28
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 241000221785 Erysiphales Species 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 235000013339 cereals Nutrition 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 241000233866 Fungi Species 0.000 claims description 15
- -1 R a O-alkyl Chemical group 0.000 claims description 15
- 235000021307 Triticum Nutrition 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 241001533598 Septoria Species 0.000 claims description 10
- 230000003032 phytopathogenic effect Effects 0.000 claims description 10
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- 240000006365 Vitis vinifera Species 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 240000005979 Hordeum vulgare Species 0.000 claims description 8
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 8
- 235000013311 vegetables Nutrition 0.000 claims description 8
- 240000007124 Brassica oleracea Species 0.000 claims description 6
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 claims description 6
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 claims description 6
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
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- 240000004713 Pisum sativum Species 0.000 claims description 5
- 235000010582 Pisum sativum Nutrition 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 240000003768 Solanum lycopersicum Species 0.000 claims description 4
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- 240000008042 Zea mays Species 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 244000291564 Allium cepa Species 0.000 claims description 3
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 244000013123 dwarf bean Species 0.000 claims description 3
- 235000005489 dwarf bean Nutrition 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 claims description 2
- BKBSMMUEEAWFRX-NBVRZTHBSA-N (E)-flumorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(F)=CC=1)=C\C(=O)N1CCOCC1 BKBSMMUEEAWFRX-NBVRZTHBSA-N 0.000 claims description 2
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 claims description 2
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 2
- BAWHYOHVWHQWFQ-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC2=CC=CC=C12 BAWHYOHVWHQWFQ-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
- QKJJCZYFXJCKRX-HZHKWBLPSA-N 2-[(2s,3s,6r)-6-[4-amino-5-(hydroxymethyl)-2-oxopyrimidin-1-yl]-3-[[(2s)-2-amino-3-hydroxypropanoyl]amino]-3,6-dihydro-2h-pyran-2-yl]-5-(diaminomethylideneamino)-2,4-dihydroxypentanoic acid Chemical compound O1[C@H](C(O)(CC(O)CN=C(N)N)C(O)=O)[C@@H](NC(=O)[C@H](CO)N)C=C[C@@H]1N1C(=O)N=C(N)C(CO)=C1 QKJJCZYFXJCKRX-HZHKWBLPSA-N 0.000 claims description 2
- CACOMUHPQMDEJQ-UHFFFAOYSA-N 2-amino-4-methyl-n-phenyl-1,3-thiazole-5-carboxamide Chemical compound N1=C(N)SC(C(=O)NC=2C=CC=CC=2)=C1C CACOMUHPQMDEJQ-UHFFFAOYSA-N 0.000 claims description 2
- ZVOWUYIDRJPVTD-UHFFFAOYSA-N 3,4,5-trichloropyridine-2,6-dicarbonitrile Chemical compound ClC1=C(Cl)C(C#N)=NC(C#N)=C1Cl ZVOWUYIDRJPVTD-UHFFFAOYSA-N 0.000 claims description 2
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 2
- SBUKOHLFHYSZNG-UHFFFAOYSA-N 4-dodecyl-2,6-dimethylmorpholine Chemical compound CCCCCCCCCCCCN1CC(C)OC(C)C1 SBUKOHLFHYSZNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- GABNAHQQEVWYNS-UHFFFAOYSA-N 5-phenyl-2,3-dihydro-1,4-dithiine 1,1,4,4-tetraoxide Chemical compound O=S1(=O)CCS(=O)(=O)C(C=2C=CC=CC=2)=C1 GABNAHQQEVWYNS-UHFFFAOYSA-N 0.000 claims description 2
- 235000006667 Aleurites moluccana Nutrition 0.000 claims description 2
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- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 claims description 2
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- 235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 2
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- 235000009025 Carya illinoensis Nutrition 0.000 claims description 2
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- 235000005979 Citrus limon Nutrition 0.000 claims description 2
- 244000248349 Citrus limon Species 0.000 claims description 2
- 241000219104 Cucurbitaceae Species 0.000 claims description 2
- 239000005755 Cyflufenamid Substances 0.000 claims description 2
- 240000009088 Fragaria x ananassa Species 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- VROYMKJUVCKXBU-UHFFFAOYSA-N Irumamycin Natural products CCC(=O)C1(C)OC1C(C)CC(C)C1C(C)C(O)C(C)C=CC(OC2OC(C)C(O)C(OC(N)=O)C2)CCCC=C(C)C(O2)C(C)=CCC2(O)CC(=O)O1 VROYMKJUVCKXBU-UHFFFAOYSA-N 0.000 claims description 2
- 235000009496 Juglans regia Nutrition 0.000 claims description 2
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- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 claims description 2
- NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
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- LDWLDRDKNBEKMZ-UHFFFAOYSA-N methyl 3-(2,2-dimethyl-1,3-dihydroinden-1-yl)imidazole-4-carboxylate Chemical compound COC(=O)C1=CN=CN1C1C(C)(C)CC2=CC=CC=C21 LDWLDRDKNBEKMZ-UHFFFAOYSA-N 0.000 claims description 2
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000004515 macrogranule Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000004531 microgranule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004536 oil dispersible powder Substances 0.000 description 1
- 239000004535 oil miscible liquid Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 150000003904 phospholipids Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000004541 plant rodlet Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000004493 powder for dry seed treatment Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000004504 smoke candle Substances 0.000 description 1
- 239000004505 smoke cartridge Substances 0.000 description 1
- 239000004509 smoke generator Substances 0.000 description 1
- 239000004510 smoke pellet Substances 0.000 description 1
- 239000004506 smoke rodlet Substances 0.000 description 1
- 239000004508 smoke tablet Substances 0.000 description 1
- 239000004502 smoke tin Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000004528 solution for seed treatment Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000004559 tracking powder Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 239000004561 vapour releasing product Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004564 water dispersible powder for slurry treatment Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04356031.7 | 2004-03-05 | ||
| EP04356031A EP1570736A1 (en) | 2004-03-05 | 2004-03-05 | Fungicide composition comprising an arylamidine derivative and known fungicide compounds |
| PCT/EP2005/003284 WO2005089547A1 (en) | 2004-03-05 | 2005-03-03 | Fungicide composition comprising an arylamidine derivative and known fungicide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2553255A1 true CA2553255A1 (en) | 2005-09-29 |
Family
ID=34746180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002553255A Abandoned CA2553255A1 (en) | 2004-03-05 | 2005-03-03 | Fungicide composition comprising an arylamidine derivative and known fungicide compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20070155802A1 (OSRAM) |
| EP (2) | EP1570736A1 (OSRAM) |
| JP (1) | JP2007526280A (OSRAM) |
| KR (1) | KR20060131840A (OSRAM) |
| CN (1) | CN1929736A (OSRAM) |
| AR (1) | AR048746A1 (OSRAM) |
| AU (1) | AU2005224034A1 (OSRAM) |
| BR (1) | BRPI0506546A (OSRAM) |
| CA (1) | CA2553255A1 (OSRAM) |
| IL (1) | IL177344A0 (OSRAM) |
| IN (1) | IN2006DE04099A (OSRAM) |
| MX (1) | MXPA06009850A (OSRAM) |
| RU (1) | RU2006135123A (OSRAM) |
| WO (1) | WO2005089547A1 (OSRAM) |
| ZA (1) | ZA200606677B (OSRAM) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2611178C (en) * | 2005-06-09 | 2016-02-23 | Bayer Cropscience Ag | Combinations comprising glufosinate and strobilurins |
| EP1931200A1 (en) * | 2005-09-13 | 2008-06-18 | Bayer CropScience AG | Fungicide composition comprising an arylamidine derivative and two known fungicide compounds |
| MX2008003431A (es) * | 2005-09-13 | 2008-03-27 | Bayer Cropscience Ag | Derivados fungicidas de fenilamidina sustituida con piridiniloxi. |
| AR058042A1 (es) | 2005-09-13 | 2008-01-23 | Bayer Cropscience Ag | Derivados plaguicidas de fenilamidina sustituida con naftiloxi |
| WO2007031526A1 (en) * | 2005-09-13 | 2007-03-22 | Bayer Cropscience Ag | Pesticide benzyloxy- and phenetyl-substituted phenyl-amidine derivatives |
| JP2009507894A (ja) * | 2005-09-13 | 2009-02-26 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺有害生物剤ピリミジニルオキシ置換フェニルアミジン誘導体 |
| US7999137B2 (en) * | 2005-09-13 | 2011-08-16 | Bayer Cropscience Ag | Pesticide bi-phenyl-amidine derivatives |
| PL1931622T3 (pl) * | 2005-09-13 | 2012-01-31 | Bayer Cropscience Ag | Podstawione fenyloksy pochodne fenyloamidyny jako pestycydy |
| PL1942737T3 (pl) * | 2005-10-28 | 2010-08-31 | Basf Se | Sposób indukowania odporności na szkodliwe grzyby |
| US8513286B2 (en) * | 2007-02-22 | 2013-08-20 | Syngenta Crop Protection Llc | Iminipyridine derivatives and their uses as microbiocides |
| US20100167926A1 (en) * | 2007-03-12 | 2010-07-01 | Bayer Cropscience Ag | 3-substituted phenoxyphenylamidines and use thereof as fungicides |
| EP1969935A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 3,4-Disubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969929A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituierte Phenylamidine und deren Verwendung als Fungizide |
| WO2008110279A1 (de) * | 2007-03-12 | 2008-09-18 | Bayer Cropscience Ag | Dihalogenphenoxyphenylamidine und deren verwendung als fungizide |
| EP1969930A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP2120558B1 (de) * | 2007-03-12 | 2016-02-10 | Bayer Intellectual Property GmbH | 3,4-Disubstituierte Phenoxyphenylamidin-Derivate und deren Verwendung als Fungizide |
| EP1969932A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969933A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Dihalogenphenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969931A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience Aktiengesellschaft | Fluoalkylphenylamidine und deren Verwendung als Fungizide |
| EP1969934A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 4-Cycloalkyl-oder 4-arylsubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| US20120064190A1 (en) * | 2009-06-04 | 2012-03-15 | Herbert Buschhaus | Method for producing fermented malt beverage using cereals treated with thiophanate-methyl |
| WO2011080044A2 (en) | 2009-12-16 | 2011-07-07 | Bayer Cropscience Ag | Active compound combinations |
| AU2012247956B2 (en) * | 2011-12-14 | 2016-10-13 | Syngenta Participations Ag | Fungicidal compositions |
| EP2606726A1 (de) * | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
| ITMI20120405A1 (it) * | 2012-03-15 | 2013-09-16 | Chemtura Corp | "composizioni sinergiche ad attivita' fungicida e relativo uso" |
| CN103621512B (zh) * | 2012-08-21 | 2016-03-30 | 陕西美邦农药有限公司 | 一种高效农药组合物 |
| US9668477B2 (en) | 2012-09-07 | 2017-06-06 | Bayer Cropscience Ag | Active compound combinations |
| BR112015004938B1 (pt) | 2012-09-07 | 2020-07-28 | Bayer Cropscience Ag | combinações fungicidas sinérgicas compreendendo um composto amidina e um inibidor da biossíntese do ergosterol, suas utilizações e métodos para o controle de fungos fitopatogênicos |
| EP2865267A1 (en) | 2014-02-13 | 2015-04-29 | Bayer CropScience AG | Active compound combinations comprising phenylamidine compounds and biological control agents |
| EP2865265A1 (en) | 2014-02-13 | 2015-04-29 | Bayer CropScience AG | Active compound combinations comprising phenylamidine compounds and biological control agents |
| WO2015121231A1 (en) * | 2014-02-13 | 2015-08-20 | Bayer Cropscience Ag | Active compound combinations comprising phenylamidine compounds and further fungicides |
| RS61217B1 (sr) | 2015-06-15 | 2021-01-29 | Syngenta Crop Protection Ag | Fenoksifenilamidini supstituisani halogenom i njihova upotreba kao fungicida |
| EP3011832A1 (en) | 2015-06-15 | 2016-04-27 | Bayer CropScience AG | Fungicidal combination comprising phenoxyphenylamidines and further fungicide |
| US10252977B2 (en) | 2015-06-15 | 2019-04-09 | Bayer Cropscience Aktiengesellschaft | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
| RU2735177C2 (ru) | 2015-07-08 | 2020-10-28 | Байер Кропсайенс Акциенгезельшафт | Феноксигалогенфениламидины и их применение в качестве фунгицидов |
| JP2019505492A (ja) * | 2015-12-15 | 2019-02-28 | シンジェンタ パーティシペーションズ アーゲー | 殺微生物フェニルアミジン誘導体 |
| WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
| KR20190097105A (ko) | 2016-12-14 | 2019-08-20 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 페닐아미딘 및 살진균제로서의 이들의 용도 |
| JP2020502105A (ja) | 2016-12-14 | 2020-01-23 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | フェノキシフェニルアミジンおよびその殺菌剤としての使用 |
| WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| JP2020523382A (ja) | 2017-06-14 | 2020-08-06 | シンジェンタ パーティシペーションズ アーゲー | 殺菌・殺カビ性組成物 |
| AR117788A1 (es) | 2019-01-14 | 2021-08-25 | Pi Industries Ltd | Compuestos de fenilamidina 3-sustituida, preparación y uso |
| CN112778230A (zh) * | 2019-11-07 | 2021-05-11 | 浙江省化工研究院有限公司 | 一类含芳基脒结构的化合物、其制备方法及应用 |
| UY38951A (es) | 2019-11-12 | 2021-06-30 | Pi Industries Ltd | Nueva composición agroquímica que comprende compuestos de fenilamidina 4- sustituidos |
| EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
| AU2021389131A1 (en) | 2020-11-30 | 2023-06-29 | Pi Industries Ltd. | Agrochemical composition comprising 3-substituted phenylamidine compounds and use thereof |
| EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9902592D0 (en) * | 1999-02-06 | 1999-03-24 | Hoechst Schering Agrevo Gmbh | Fungicides |
| FR2829362B1 (fr) * | 2001-09-10 | 2003-11-07 | Aventis Cropscience Sa | Composition fongicide a base de derives d'arylamidine et de composes fongicides connus |
| BR0309599A (pt) * | 2002-05-03 | 2005-03-01 | Du Pont | Composto, composições fungicidas e método para o controle de doenças vegetais |
| EP1413301A1 (fr) * | 2002-10-24 | 2004-04-28 | Bayer CropScience SA | Médicaments antifongiques à base de dérivés d'arylamidine |
-
2004
- 2004-03-05 EP EP04356031A patent/EP1570736A1/en not_active Withdrawn
-
2005
- 2005-03-03 WO PCT/EP2005/003284 patent/WO2005089547A1/en not_active Ceased
- 2005-03-03 AU AU2005224034A patent/AU2005224034A1/en not_active Abandoned
- 2005-03-03 CN CNA2005800069684A patent/CN1929736A/zh active Pending
- 2005-03-03 EP EP05739560A patent/EP1722629A1/en not_active Withdrawn
- 2005-03-03 CA CA002553255A patent/CA2553255A1/en not_active Abandoned
- 2005-03-03 US US10/589,011 patent/US20070155802A1/en not_active Abandoned
- 2005-03-03 RU RU2006135123/04A patent/RU2006135123A/ru not_active Application Discontinuation
- 2005-03-03 JP JP2007501252A patent/JP2007526280A/ja active Pending
- 2005-03-03 BR BRPI0506546-1A patent/BRPI0506546A/pt not_active IP Right Cessation
- 2005-03-03 KR KR1020067016104A patent/KR20060131840A/ko not_active Withdrawn
- 2005-03-04 AR ARP050100834A patent/AR048746A1/es unknown
-
2006
- 2006-07-17 IN IN4099DE2006 patent/IN2006DE04099A/en unknown
- 2006-08-07 IL IL177344A patent/IL177344A0/en unknown
- 2006-08-11 ZA ZA200606677A patent/ZA200606677B/xx unknown
- 2006-08-30 MX MXPA06009850 patent/MXPA06009850A/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005089547A1 (en) | 2005-09-29 |
| IN2006DE04099A (OSRAM) | 2007-06-22 |
| MXPA06009850A (es) | 2006-12-01 |
| AU2005224034A1 (en) | 2005-09-29 |
| US20070155802A1 (en) | 2007-07-05 |
| ZA200606677B (en) | 2008-02-27 |
| RU2006135123A (ru) | 2008-04-10 |
| EP1570736A1 (en) | 2005-09-07 |
| IL177344A0 (en) | 2006-12-10 |
| BRPI0506546A (pt) | 2007-02-27 |
| CN1929736A (zh) | 2007-03-14 |
| JP2007526280A (ja) | 2007-09-13 |
| KR20060131840A (ko) | 2006-12-20 |
| AR048746A1 (es) | 2006-05-24 |
| EP1722629A1 (en) | 2006-11-22 |
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