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 (https=) |
| EP (2) | EP1570736A1 (https=) |
| JP (1) | JP2007526280A (https=) |
| KR (1) | KR20060131840A (https=) |
| CN (1) | CN1929736A (https=) |
| AR (1) | AR048746A1 (https=) |
| AU (1) | AU2005224034A1 (https=) |
| BR (1) | BRPI0506546A (https=) |
| CA (1) | CA2553255A1 (https=) |
| IL (1) | IL177344A0 (https=) |
| IN (1) | IN2006DE04099A (https=) |
| MX (1) | MXPA06009850A (https=) |
| RU (1) | RU2006135123A (https=) |
| WO (1) | WO2005089547A1 (https=) |
| ZA (1) | ZA200606677B (https=) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104170838B (zh) * | 2005-06-09 | 2016-03-30 | 拜尔农作物科学股份公司 | 活性物质结合物 |
| EP1928818B1 (en) * | 2005-09-13 | 2012-03-21 | Bayer CropScience AG | Pesticide benzyloxy- and phenetyl-substituted phenyl-amidine derivatives |
| WO2007093227A1 (en) * | 2005-09-13 | 2007-08-23 | Bayer Cropscience Ag | Pesticide naphthyloxy substituted phenylamidine derivatives |
| EP1926706B1 (en) * | 2005-09-13 | 2012-03-21 | Bayer CropScience AG | Pesticide bi-phenyl-amidine derivatives |
| ATE521588T1 (de) * | 2005-09-13 | 2011-09-15 | Bayer Cropscience Ag | Phenyloxy-substituierte phenylamidin-derivate als pestizide |
| AR056869A1 (es) * | 2005-09-13 | 2007-10-31 | Bayer Cropscience Ag | Composicion fungicida que comprende un derivado arilamidina y dos compuestos fungicidas conocidos |
| AR056508A1 (es) | 2005-09-13 | 2007-10-10 | Bayer Cropscience Ag | Derivados plaguicidas de fenilamidina sustituida con pirimidiniloxi |
| US7994334B2 (en) * | 2005-09-13 | 2011-08-09 | Bayer Cropscience Ag | Fungicide pyridinyloxy substituted phenylamidine derivatives |
| ATE459253T1 (de) * | 2005-10-28 | 2010-03-15 | Basf Se | Verfahren zur induktion von resistenz gegen schadpilze |
| MX2009008798A (es) * | 2007-02-22 | 2009-08-24 | Syngenta Participations Ag | Derivados de iminipiridina y sus usos como microbicidas. |
| JP2010520900A (ja) * | 2007-03-12 | 2010-06-17 | 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 | フェノキシ置換されたフェニルアミジン誘導体及び殺真菌剤としてのその使用 |
| EP1969932A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| BRPI0808786A2 (pt) * | 2007-03-12 | 2014-09-16 | Bayer Cropscience Ag | Di-halogenofenoxifenilamidinas e seu uso como fungicidas |
| EP1969930A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| BRPI0808798A2 (pt) | 2007-03-12 | 2014-10-07 | Bayer Cropscience Ag | Fenoxifenilamidinas 3,5-dissubstituídas e seu uso como fungicidas |
| EP1969933A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Dihalogenphenoxyphenylamidine 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 |
| EP1969929A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituierte Phenylamidine und deren Verwendung als Fungizide |
| EP1969931A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience Aktiengesellschaft | Fluoalkylphenylamidine und deren Verwendung als Fungizide |
| EP1969935A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 3,4-Disubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| RU2491329C2 (ru) * | 2009-06-04 | 2013-08-27 | Ниппон Сода Ко., Лтд. | Способ получения ферментированных солодовых напитков с использованием зерновых, обработанных метилтиофанатом |
| WO2011080044A2 (en) | 2009-12-16 | 2011-07-07 | Bayer Cropscience Ag | Active compound combinations |
| EP2790508A4 (en) * | 2011-12-14 | 2015-08-05 | Syngenta Participations Ag | FUNGICIDE 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" |
| CN105248426B (zh) * | 2012-08-21 | 2017-12-19 | 陕西美邦农药有限公司 | 一种高效农药组合物 |
| WO2014037314A2 (en) * | 2012-09-07 | 2014-03-13 | Bayer Cropscience Ag | Active compound combinations |
| WO2014037315A2 (en) | 2012-09-07 | 2014-03-13 | Bayer Cropscience Ag | Active compound combinations |
| 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 |
| US9770023B2 (en) | 2014-02-13 | 2017-09-26 | Bayer Cropscience Aktiengesellschaft | Active compound combinations comprising phenylamidine compounds and further fungicides |
| EP3011832A1 (en) | 2015-06-15 | 2016-04-27 | Bayer CropScience AG | Fungicidal combination comprising phenoxyphenylamidines and further fungicide |
| WO2016202688A1 (en) | 2015-06-15 | 2016-12-22 | Bayer Cropscience Aktiengesellschaft | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
| MX2017016363A (es) | 2015-06-15 | 2018-03-02 | Bayer Cropscience Ag | Fenoxifenilamidinas sustituidas con halogeno y el uso de estas como fungicidas. |
| JP6811000B2 (ja) | 2015-07-08 | 2021-01-13 | 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 | フェノキシハロゲンフェニルアミジン類及び殺菌剤としてのそれらの使用 |
| MX2018007292A (es) * | 2015-12-15 | 2018-09-06 | Syngenta Participations Ag | Derivados de fenilamidina microbicidas. |
| EP3525588B1 (en) | 2016-10-14 | 2024-04-24 | PI Industries Ltd | 4-substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| AU2017342206B2 (en) | 2016-10-14 | 2022-06-02 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| WO2018108998A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Phenylamidines and the use thereof as fungicides |
| US20200077648A1 (en) | 2016-12-14 | 2020-03-12 | Bayer Cropscience Aktiengesellschaft | Phenoxyphenylamidines and the use thereof as fungicides |
| EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
| WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| WO2018228896A1 (en) * | 2017-06-14 | 2018-12-20 | Syngenta Participations Ag | Fungicidal compositions |
| UY38540A (es) | 2019-01-14 | 2020-08-31 | 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 |
| AR120427A1 (es) | 2019-11-12 | 2022-02-16 | Pi Industries Ltd | 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 |
| WO2003093224A1 (en) * | 2002-05-03 | 2003-11-13 | E.I. Du Pont De Nemours And Company | Amidinylphenyl compounds and their use as fungicides |
| 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 CA CA002553255A patent/CA2553255A1/en not_active Abandoned
- 2005-03-03 RU RU2006135123/04A patent/RU2006135123A/ru not_active Application Discontinuation
- 2005-03-03 BR BRPI0506546-1A patent/BRPI0506546A/pt not_active IP Right Cessation
- 2005-03-03 AU AU2005224034A patent/AU2005224034A1/en not_active Abandoned
- 2005-03-03 EP EP05739560A patent/EP1722629A1/en not_active Withdrawn
- 2005-03-03 CN CNA2005800069684A patent/CN1929736A/zh active Pending
- 2005-03-03 JP JP2007501252A patent/JP2007526280A/ja active Pending
- 2005-03-03 US US10/589,011 patent/US20070155802A1/en not_active Abandoned
- 2005-03-03 KR KR1020067016104A patent/KR20060131840A/ko not_active Withdrawn
- 2005-03-03 WO PCT/EP2005/003284 patent/WO2005089547A1/en not_active Ceased
- 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 |
|---|---|
| ZA200606677B (en) | 2008-02-27 |
| AU2005224034A1 (en) | 2005-09-29 |
| US20070155802A1 (en) | 2007-07-05 |
| KR20060131840A (ko) | 2006-12-20 |
| IL177344A0 (en) | 2006-12-10 |
| EP1570736A1 (en) | 2005-09-07 |
| AR048746A1 (es) | 2006-05-24 |
| BRPI0506546A (pt) | 2007-02-27 |
| IN2006DE04099A (https=) | 2007-06-22 |
| CN1929736A (zh) | 2007-03-14 |
| JP2007526280A (ja) | 2007-09-13 |
| RU2006135123A (ru) | 2008-04-10 |
| MXPA06009850A (es) | 2006-12-01 |
| EP1722629A1 (en) | 2006-11-22 |
| WO2005089547A1 (en) | 2005-09-29 |
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