Fungicidal mixtures comprising substituted pyridines
By using a mixture of different active compounds, the problem of single active compounds leading to resistant strain selection is solved, achieving a more effective and lasting harmful fungal control effect.
Patent Information
- Application Number
- CN202380078816.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-11-14
- Filing Date
- 2023-11-07
- Publication Date
- 2025-06-20
AI Technical Summary
The prior art, when controlling plant pathogenic harmful fungi, can easily lead to rapid selection of resistant strains, resulting in a reduced effectiveness of a single active compound.
Using a mixture of different active compounds, by combining active compounds with different mechanisms of action, we ensure successful control of harmful fungi and reduce the risk of resistance management.
Better anti-harmful fungal activity and broaden the activity spectrum while reducing the total amount of active compounds applied are achieved, and the time period for controlling the effect is extended.
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Abstract
Description
[0001] The present invention relates to a fungicidal mixture comprising, as active ingredients, the following:
[0002] at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt,
[0003]
[0004] wherein
[0005] R 1 is H;
[0006] R 2 is independently, in each case, selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, O-C1-C6-alkyl;
[0007] R 3 is independently, in each case, selected from C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C2-C6-alkynyl;
[0008] R 4 is H;
[0009] R 5 is independently, in each case, selected from C1-C6-alkyl, C1-C6-haloalkyl, benzyl,
[0010] wherein the benzyl moiety of R 5 is unsubstituted or substituted by one to three groups R 5a which are independently selected from the following:
[0011] halogen;
[0012] R 6 is independently, in each case, selected from C1-C6-alkyl, benzyl,
[0013] wherein the benzyl moiety of R 6 is unsubstituted or substituted by one to three groups R 6a which are independently selected from the following:
[0014] halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl;
[0015] or
[0016] R 5 and R 6 together with the C atom to which they are attached form a C3-C6-cycloalkyl, which cycloalkyl may be unsubstituted or substituted by C1-C6-alkyl, C1-C6-haloalkyl;
[0017] X is independently selected, in each case, from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl;
[0018] n is 0, 1, 2
[0019] and the following as components:
[0020] 2) at least one active compound II, which is selected from groups A) to O), or its N-oxide, or an agriculturally useful salt:
[0021] A) Respiratory inhibitors
[0022] - Complex III inhibitors at the Q o site: azoxystrobin (A.1.1), methoxyacrylic acid (A.1.2), caryophyllene (A.1.3), enestroburin (A.1.4), enoxastrobin (A.1.5), enoxam (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyraoxystrobin (A.1.15), pyrazophos (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb / chlorodincarb (A.1.20), oxpoconazole (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), tetraconazole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyridaben (A.1.36), picoxystrobin (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38);
[0023] - At Q i Complex III inhibitors at the site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), picoxystrobin (A.2.5), metarylpicoxamid (A.2.6);
[0024] - Complex II inhibitors: carboxin (A.3.1), bixafen (A.3.2), boscalid (A.3.3), boscalid (A.3.4), oxycarboxin (A.3.5), furametpyr (A.3.6), fluxapyroxad (A.3.7), flutolanil (A.3.8), fluxametamide (A.3.9), furpicoxamid (A.3.10), isofetamid (A.3.11), sedaxane (A.3.12), dimoxystrobin (A.3.13), oxycarboxin oxide (A.3.14), fluopyram (A.3.15), pydiflumetofen (A.3.16), fluxametamide (A.3.17), fluxametamide (A.3.18), fluxametamide (A.3.19), tetcyclacis (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (A.3.29), (E)-methyl 2-[2-[(5-cyano-2-methylphenoxy)methyl]phenyl]-3-methoxyprop-2-enoate (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-4H-inden-4-yl)nicotinamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethyl-4H-inden-4-yl]nicotinamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-4H-inden-4-yl)nicotinamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-4H-inden-4-yl]nicotinamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-4H-inden-4-yl)nicotinamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-4H-inden-4-yl]nicotinamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-4H-inden-4-yl)nicotinamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-4H-inden-4-yl]nicotinamide (A.3.39), triflumizole (A.3.24);
[0025] - Other respiratory inhibitors: diflufenican (A.4.1); nitro-phenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), dicofol (A.4.6), ferimzone (A.4.7); organo-metallic compounds: triphenyltin salts, such as fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); amisulbrom (A.4.11); silthiofam (A.4.12);
[0026] B) Sterol biosynthesis inhibitors (SBI fungicides)
[0027] -C14 demethylase inhibitors: Triazoles: penconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23),simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridinyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridinyl]propan-2-ol (B.1.32), fluxapyroxad (B.1.33), ipfentrifluconazole (B.1.37), chlorfluzolam (B.1.38), (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-(chloromethyl)-2-methyl-5-((p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); Imidazoles: imazalil (B.1.44), fenapanil (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); Pyrimidines, pyridines, piperazines: chlorophenylpyrimidinol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridinyl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.55), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (B.1.56), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid (B.1.57);
[0028] -δ14-reductase inhibitors: 4-dodecyl-2,6-dimethylmorpholine (Aldimorph) (B.2.1), dodemorph (B.2.2), dodemorph acetate (B.2.3), fenpropimorph (B.2.4), quinomethionate (B.2.5), fenpropidin (B.2.6), tridemorph (B.2.7), spiroxamine (B.2.8);
[0029] -3-ketoreductase inhibitors: fenhexamid (B.3.1);
[0030] -other sterol biosynthesis inhibitors: etaconazole (B.4.1);
[0031] C) Nucleic acid synthesis inhibitors
[0032] -phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
[0033] -other nucleic acid synthesis inhibitors: hymexazol (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), ethirimol sulfate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8);
[0034] D) Cell division and cytoskeleton inhibitors
[0035] - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthio-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthio-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methylthio-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16);
[0036] - Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), fenpropimorph (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7), cyenopyrac (D.2.8);
[0037] E) Amino acid and protein synthesis inhibitors
[0038] - Methionine synthesis inhibitors: cyprodinil (E.1.1), fenarimol (E.1.2), pyrimethanil (E.1.3);
[0039] - Protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), validamycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);
[0040] F) Signal transduction inhibitors
[0041] - MAP / Histidine Kinase Inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);
[0042] - G - Protein Inhibitors: quinoxyfen (F.2.1);
[0043] G) Lipid and Membrane Synthesis Inhibitors
[0044] - Phospholipid Biosynthesis Inhibitors: edifenphos (G.1.1), isoprothiolane (G.1.2), pyrazophos (G.1.3), isoprobenfos (G.1.4);
[0045] - Lipid Peroxidation: dichlofluanid (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos - methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), ethaboxam (G.2.7), thiazole zinc (G.2.8);
[0046] - Phospholipid Biosynthesis and Cell Wall Deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb - isopropyl (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
[0047] - Compounds Affecting Cell Membrane Permeability and Fatty Acids: propamocarb (G.4.1);
[0048] Oxysterol-binding protein inhibitors: flutriafol (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.11);
[0049] H) Inhibitors with multi-site action
[0050] - Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7);
[0051] - Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam sodium (H.2.4), metiram (H.2.5), zinc methyldithiocarbamate (H.2.6), thiram (H.2.7), zinc dithiocarbamate (H.2.8), zinc dimethyldithiocarbamate (H.2.9);
[0052] - Organochlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, tecnazene (H.3.10), tolylfluanid (H.3.11);
[0053] - Guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), guazatine-amine (H.4.6), guazatine-amine triacetate (H.4.7), guazatine octylbenzene sulfonate (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithieno[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (H.4.10);
[0054] I) Cell wall synthesis inhibitors
[0055] - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin (I.1.2);
[0056] - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), cyprodinil (I.2.3), dicyclomet (I.2.4), blastoxim (I.2.5);
[0057] J) Plant defense inducers
[0058] - Benzoic acid, S-methyl ester (J.1.1), thiabendazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); Phosphonates: etridiazole (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)-1,2,4-thiadiazole-5-carboxamide (J.1.10);
[0059] K) Unknown mode of action
[0060] -Bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), iminoctadine (K.1.6), diclocymet (K.1.7), pyridinitril (K.1.8), barban (K.1.9), barban - methyl sulfate (K.1.10), diphenylamine (K.1.11), cloethocarb (K.1.12), amisulbrom (K.1.13), flumetover (K.1.14), flumetylsulforim (K.1.60), sulfanilamide (K.1.15), fluopyram (K.1.16), harpin protein (K.1.17), sulfotep (K.1.18), 3,5,6 - trichloro - 2 - pyridinol (K.1.19), phthalide (K.1.20), tolprocarb (K.1.21), copper quinolate (K.1.22), propoxyquinoline (K.1.23), seboctylamine (K.1.61), tebufloquin (K.1.24), phthalideyl (K.1.25), pyrazophos (K.1.26), N'-(4-(4 - chloro - 3 - trifluoromethyl - phenoxy)-2,5 - dimethyl - phenyl)-N - ethyl - N - methyl - formamidine (K.1.27), N'-(4-(4 - fluoro - 3 - trifluoromethyl - phenoxy)-2,5 - dimethyl - phenyl)-N - ethyl - N - methyl - formamidine (K.1.28), N'-[4-[[3-[(4 - chlorophenyl)methyl]-1,2,4 - thiadiazol - 5 - yl]oxy]-2,5 - dimethyl - phenyl]-N - ethyl - N - methyl - formamidine (K.1.29), N'-(5 - bromo - 6 - indan - 2 - yloxy - 2 - methyl - 3 - pyridyl)-N - ethyl - N - methyl - formamidine (K.1.30), N'-[5 - bromo - 6-[1-(3,5 - difluorophenyl)ethoxy]-2 - methyl - 3 - pyridyl]-N - ethyl - N - methyl - formamidine (K.1.31), N'-[5 - bromo - 6-(4 - isopropylcyclohexyloxy)-2 - methyl - 3 - pyridyl]-N - ethyl - N - methyl - formamidine (K.1.32), N'-[5 - bromo - 2 - methyl - 6-(1 - phenylethoxy)-3 - pyridyl]-N - ethyl - N - methyl - formamidine (K.1.33), N'-(2 - methyl - 5 - trifluoromethyl - 4-(3 - trimethylsilyl - propoxy)phenyl)-N - ethyl - N - methyl - formamidine (K.1.34), N'-(5 - difluoromethyl - 2 - methyl - 4-(3 - trimethylsilyl - propoxy)-phenyl)-N - ethyl - N - methyl - formamidine (K.1.35), 2-(4 - chlorophenyl)-N-[4-(3,4 - dimethoxyphenyl)-isoxazol - 5 - yl]-2 - prop - 2 - ynyloxy - acetamide (K.1.36), 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (picoxystrobin) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenylprop-2-enoate (K.1.40), tetraconazole (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridinyl]pentylcarbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridinyl]but-3-ynylcarbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), cymoxanil (K.1.48), bromothalonil (K.1.49), 2-(6-benzyl-2-pyridinyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridinyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (K.1.53), amisulbrom (K.1.54), fluxapyroxad (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridinyl]-N-ethyl-N-methylformamidine (K.1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (K.1.57), flufenoxadiazam (K.1.58), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide (K.1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.60; WO 2018 / 177894, WO 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]butanamide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate (K.1.83), N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]-1H-1,2,4-triazol-3-amine (K.1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.87), N-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.88), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.91), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (K.1.92), N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.95), N'-[2-chloro-4-[(4-methoxyphenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.96), N'-[2-chloro-4-[(4-cyanophenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methylformamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluoro-phenoxy)-6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104);.
[0061] L) Biocidal pest control agents
[0062] L1) Microbial pest control agents with fungicidal, bactericidal, virucidal, and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantarum (also known as Bacillus velezensis), Bacillus megaterium, Bacillus mojavensis, Bacillus mycoides, Bacillus pumilus, Bacillus simplex, Bacillus salarius, Bacillus subtilis, Bacillus subtilis var. amyloliquefaciens, Bacillus velezensis, Candida oleophila, Candida saitoana, Clavibacter michiganensis (phage), Coniothyrium minitans, Cryptocline parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, Lysobacter enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Mycosphaerella cruenta, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, Paenibacillus polymyxa, Pantoea agglomerans, Penicillium bilaiae, Phellinus igniarius, Pseudomonas spp., Pseudomonas chlororaphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, Streptomyces lydicus, Streptomyces violaceoniger, Talaromyces flavus, Trichoderma asperelloides, Trichoderma asperellum, Trichoderma atroviride, Trichoderma apical, Trichoderma gamosum, Trichoderma harzianum, Trichoderma harmatum, Trichoderma polysporum, Trichoderma stromaticum, Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, Zucchini yellow mosaic virus (avirulent strain);
[0063] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal, and / or plant defense activator activity: Harpin protein, Reynoutria japonica extract;
[0064] L3) Microbial pest control agents with insecticidal, acaricidal, molluscicidal and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, Bacillus firmus, Bacillus thuringiensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. galleriae, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Beauveria bassiana, Beauveria brongniartii, Burkholderia species, Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium species, Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Heliothis zea nucleopolyhedrovirus (HzNPV), Heliothis zea single nucleocapsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, Lecanicillium muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, Metarhizium anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Paenibacillus popilliae, Pasteuria species, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, Pseudomonas fluorescens, Spodoptera litura nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, Steinernema feltiae, Steinernema serratum, Streptomyces gilvosporeus, Streptomyces microflavus;
[0065] L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, ethyl (E,Z)-2,4-decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyleugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-yl acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone (pentatermanone), (E,Z,Z)-3,8,11-tetradecatrien-1-yl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, neem oil, Quillay extract;
[0066] L5) Microbial pesticides with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activity: Azospirillum amazonense, Azospirillum brasilense, Azospirillum lipoferum, Azospirillum iraquense, Azospirillum halopraeferens, Bradyrhizobium spp., Bradyrhizobium elkanii, Bradyrhizobium japonicum, Bradyrhizobium liaoningense, Bradyrhizobium lupini, Delftia acidovorans, arbuscular mycorrhizal fungi, Mesorhizobium spp., Rhizobium leguminosarum biovar phaseoli, Rhizobium leguminosarum biovar trifolii, Rhizobium leguminosarum biovar viciae, Rhizobium tropici, Sinorhizobium meliloti;
[0067] O) Insecticides from classes O.1 to O.29
[0068] O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, chlorthiophos, coumaphos, cyanthoate, dichlorvos / DDVP, dimethoate, ethion, EPN, ethoprophos, fenamiphos, fenthion, fosthiazate, heptenophos, imicyafos, isopropylamine phosphate, O-(methoxyaminothiophosphoryl) salicylic acid isopropyl ester, isoxathion, malathion, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, pyrethrins, pyriproxyfen, pyridaphenthion, quinalphos, sulprofos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
[0069] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, butene-fipronil, pyrafluprole, pyriprole;
[0070] O.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, k-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flumethrin, tau-fluvalinate, flubrocythrinate, heptaflumethrin, imiprothrin, metofluthrin, metofluthrin-epsilon, permethrin, phenothrin, propargite, propalphos, pyrethrum, resmethrin, silafluofen, tefluthrin, k-tefluthrin, tetraflurofen, tetramethrin, tralomethrin, triflumezopyrim; DDT, methoxychlor;
[0071] O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, epoxiconazole, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylideneamino-guanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradifurone, triflumezopyrim, bixafen, flufenerim;
[0072] O.5 Allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram;
[0073] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;
[0074] O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;
[0075] O.8 Various non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
[0076] O.9 Chordotonal organ TRPV channel modulators: cyenopyrafen, pymetrozine, flupyradifurone;
[0077] O.10 Mite growth inhibitors: clofentezine, hexythiazox, flufenzine; etoxazole;
[0078] O.11 Microbial disruptors of the insect midgut membrane: Bacillus thuringiensis, Bacillus sphaericus, and the insecticidal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;
[0079] O.12 Mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, chlorfenson;
[0080] O.13 Oxidative phosphorylation uncouplers interfering via proton gradient: chlorfenapyr, DNOC, sulfluramid;
[0081] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap, thiocyclam, bisultap;
[0082] O.15 Chitin biosynthesis inhibitor type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron;
[0083] O.16 Chitin biosynthesis inhibitor type 1: buprofezin;
[0084] O.17 Molting disruptors: cyromazine;
[0085] O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;
[0086] O.19 Octopamine receptor agonists: amitraz;
[0087] O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate;
[0088] O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, flubenzimine, pyridaben, pyrimidifen, tolfenpyrad, flufenerim; rotenone;
[0089] O.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]hydrazinecarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide;
[0090] O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, methoprene, spirodiclofen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-ene-10-one, dispirotetramat;
[0091] O.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
[0092] O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, butylpyridaben, etoxazole, pyraclostrobin;
[0093] O.28 Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, flubendiamide, (R)-3-chloro-N 1 -{2-methyl-4-[1,2,2,2–tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N 1 -{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2-(1-Methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl-λ4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloropyridin-2-yl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorantraniliprole; tetraniliprole; thiodicarb; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorantraniliprole; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide;
[0094] O.29 Chordotonal organ regulator: flonicamid;
[0095] O.30 GABA-gated chloride channel allosteric regulator: broflanilide, chlorantraniliprole, isoxazolinonitrile;
[0096] O.33 Calcium-activated potassium channel regulator: acynonapyr;
[0097] O.34 Mitochondrial complex III electron transport inhibitor at the Qi site: flometoquin;
[0098] O.UN Insecticidal compounds with unknown or uncertain mode of action: afoxolaner, azadirachtin, amidoflumet, bromopropylate, chlorbenside, chinomethionat, cryolite, cyproflanilid, dichlorothymid, dicofol, flupyradifurone, flufenerim, flutriafol, fluvalinate, hydramethylnon, piperonyl butoxide, pyridalyl, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 4-cyano-N-[2-cyano-5-[[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide, N-[5-[[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, active substance based on Bacillus firmus (Votivo, I-1582); triflumizole; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 2-(1,3-dioxolan-2-yl)-6-[2-(3-pyridyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; 2-[6-[2-(3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 2-(3-pyridyl)-N-(2-pyrimidylmethyl)-2H-indazole-5-carboxamide; chlorantraniliprole; sarolaner, lotilaner; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2-(2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; benzpyrimoxan; tigolaner; oxasulfuron; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]Pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cyclopropanecarboxamide; 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one; Flupyradifurone, N-[3-chloro-1-(3-pyridinyl)pyrazol-4-yl]-2-methylsulfonyl-propionamide, Triflumidopyrim; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, Cyflumetofen, Cyazypyr; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione, 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl]imino-3-(2,2,2-(Trifluoroethyl)thiazolidin-4-one, indoxacarb, N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylsulfonyl-propanamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)isoquinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole,
[0099] The weight ratio of these components is from 1:100 to 100:1.
[0100] The invention also relates to a method for controlling phytopathogenic harmful fungi using a mixture of at least one compound I and at least one compound II in a weight ratio of from 100:1 to 1:100; to the use of a mixture comprising compound I and compound II for controlling phytopathogenic harmful fungi; to an agrochemical composition comprising these mixtures; and to an agrochemical composition further comprising seeds.
[0101] Practical agricultural experience has shown that, when controlling harmful fungi, repeated and exclusive application of the individual active compounds in many cases leads to a rapid selection of those fungal strains that develop a natural or adapted resistance to the active compound in question. These fungi can then no longer be effectively controlled with the active compound in question.
[0102] To reduce the risk of selection of resistant fungal strains, mixtures of different active compounds are generally used for controlling harmful fungi. By combining active compounds with different modes of action, successful control can be ensured over a relatively long period of time.
[0103] The object of the invention is to provide compositions which, from the point of view of effective resistance management and effective control of phytopathogenic harmful fungi, have improved antifungal activity (synergistic mixtures) at as low an application rate as possible and, in particular for certain indications, a broadened activity spectrum at a reduced total amount of active compounds applied.
[0104] Accordingly, we have found that this object is achieved by the compositions defined herein, which comprise at least one compound I and at least one compound II.
[0105] Furthermore, we have found that the simultaneous (i.e., combined or separate) application of compound I and compound II or the sequential application of compound I and compound II allows for better control of harmful fungi (synergistic mixtures) compared to the control of harmful fungi that may be achieved by using only the individual compounds. Compound I and / or compound II may be present in different crystal modifications, which may differ in biological activity.
[0106] The term "compound I" refers to a compound having formula I.
[0107] In the definitions of the variables given above, collective terms are used which usually represent the substituents in question. The term "C n -C m " indicates the possible number of carbon atoms in the substituent or substituent part in question in each case.
[0108] The term "halogen" refers to fluorine, chlorine, bromine and iodine.
[0109] The term "C1-C6-alkyl" refers to a straight-chain or branched-chain saturated hydrocarbon radical having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl.
[0110] The term "C2-C6-alkenyl" refers to a straight-chain or branched-chain unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond at any position, such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
[0111] The term "C2-C6-alkynyl" refers to a straight-chain or branched-chain unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, 1-propynyl, 2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl.
[0112] The term "C1-C6-haloalkyl" refers to a straight-chain or branched alkyl group having from 1 to 6 carbon atoms (as defined above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.
[0113] The term "C1-C6-alkoxy" refers to a straight-chain or branched alkyl group having from 1 to 6 carbon atoms (as defined above), which is bonded via oxygen at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.
[0114] The term "aliphatic" refers to compounds or groups composed of carbon and hydrogen, and they are non-aromatic compounds. "Cycloaliphatic" compounds or groups are both aliphatic and cyclic organic compounds. They contain one or more all-carbon rings which may be saturated or unsaturated, but do not have aromatic characteristics.
[0115] The term "cyclic moiety" or "cyclic group" refers to a group that is an alicyclic ring or an aromatic ring, such as a phenyl group or a heteroaryl group.
[0116] The term "and wherein any one of the aliphatic or cyclic groups is unsubstituted or substituted by..." refers to aliphatic groups, cyclic groups and groups containing aliphatic and cyclic moieties in one group (such as a C3-C8-cycloalkyl-C1-C4-alkyl group); thus, for a group containing aliphatic and cyclic moieties, these two moieties may be independently substituted or unsubstituted.
[0117] The term "phenyl" refers to an aromatic ring system containing six carbon atoms (commonly known as a benzene ring).
[0118] The term "benzyl" refers to an aromatic ring system containing six carbon atoms and a CH2 group.
[0119] The agriculturally acceptable salts of active compounds I, II and III cover in particular the salts of cations or the acid addition salts of acids, where these cations and anions respectively have no adverse effect on the fungicidal action of these active compounds. Accordingly, suitable cations are in particular alkali metal (preferably sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium and barium) ions, transition metal (preferably manganese, copper, zinc and iron) ions, and also the ammonium ion, which, if desired, can carry 1 to 4 C1-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium. The anions of the acid addition salts which can be used are mainly chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compound I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
[0120] The scope of the invention includes mixtures of (R)- and (S)-isomers and racemates of compounds I and / or II and / or III having one or more chiral centers. Due to the hindered rotation of the asymmetrically substituted groups, atropisomers of active compounds I and / or II and / or III can be present. They also form part of the subject matter of the invention.
[0121] Compound I and its preparation and its use as a fungicidal active compound have been described in PCT / EP2022 / 062598.
[0122] For example, compound I can be prepared by a palladium-catalyzed Suzuki coupling reaction between a boronic acid derivative represented by formula 3 and a triflate derivative represented by formula 2 using a palladium complex in an organic solvent. Preferably, the reaction is carried out at an elevated temperature, preferably between 60 °C and 160 °C, and 1 - 3 equivalents of the boronic acid derivative represented by formula 3 are used per 1 equivalent of triflate 2, as described in WO 2009119089 A1.
[0123]
[0124] The compound having the formula 2 can be prepared from the cyclic amide compound 4 by treating it with trifluoromethanesulfonic anhydride in the presence of a base such as pyridine, 2,6 - dimethylpyridine, 2,3,5 - trimethylpyridine, triethylamine, tributylamine, diisopropylethylamine, etc.; or a tertiary cyclic amine such as 1,4 - diazabicyclo[2.2.2]octane, 1,5 - diazabicyclo[4.3.0]non - 5 - ene, 1,8 - diazabicyclo[5.4.0]undec - 7 - ene or an aromatic amine such as N,N - dimethylaniline, N,N - diethylaniline, 4 - dimethylaminopyridine in an organic halogenated aliphatic hydrocarbon solvent such as chloroform, dichloromethane, dichloroethane, as described in WO 2009119089A1 and EP 2179994 B1.
[0125]
[0126] The cyclic amide compound having the formula 4 is commercially available or can be obtained by forming an acetal from the corresponding salicylamide 5 with a dimethoxyalkane or dimethoxycycloalkane in an organic solvent and in the presence of an acid such as p - toluenesulfonic acid (p - TsOH), pyridinium p - toluenesulfonate, sulfuric acid or acetic acid (for precedents, see for example Tetrahedron (2015), 71(34), 5554 - 5561, Journal of Organic Chemistry (1981), 46(16), 3340 - 2, Bioorganic & Medicinal Chemistry (2006), 14(6), 1978 - 1992).
[0127] The compound having the formula 4 can also be prepared via the condensation between salicylamide 5 and a ketone 7, which is catalyzed by a secondary amine such as pyrrolidine, morpholine, etc. The reaction is preferably carried out in refluxing benzene or toluene with 10% amine catalyst (for precedents, see for example J. Org. Chem. 1981, 46, 3340 - 3342, Synthesis 1978, 886).
[0128]
[0129] In one embodiment, the present invention relates to mixtures which comprise, as component 1), at least one active compound having the formula I, or its N - oxide, or an agriculturally useful salt, wherein:
[0130] R 1 is H;
[0131] R 2 is CH3;
[0132] R3 independently selected from CH3, CHF2 in each case;
[0133] R 4 is H;
[0134] R 5 independently selected from CH3 in each case;
[0135] R 6 independently selected from CH3 in each case;
[0136] X is independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl in each case;
[0137] n is 1, 2.
[0138] In one embodiment, the invention relates to mixtures which comprise, as component 1), at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein:
[0139] R 1 is H;
[0140] R 2 is CH3;
[0141] R 3 independently selected from CH3, CHF2 in each case;
[0142] R 4 is H;
[0143] R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl;
[0144] X is independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl in each case;
[0145] n is 1, 2.
[0146] In one embodiment, the invention relates to mixtures which comprise, as component 1), at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein:
[0147] R 1 is H;
[0148] R 2 is CH3;
[0149] R 3 independently selected from CH3, CHF2 in each case;
[0150] R 4 is H;
[0151] R 5 independently selected from CH3 in each case;
[0152] R 6 independently selected from CH3 in each case;
[0153] X is independently selected from halogen, C1-C6-alkyl, O-C1-C6-alkyl in each case;
[0154] n is 1, 2.
[0155] In one embodiment, the present invention relates to mixtures which comprise, as component 1), at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein:
[0156] R 1 is H;
[0157] R 2 is CH3;
[0158] R 3 independently selected from CH3, CHF2 in each case;
[0159] R 4 is H;
[0160] R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl;
[0161] X is independently selected from halogen, C1-C6-alkyl, O-C1-C6-alkyl in each case;
[0162] n is 1, 2.
[0163] In one embodiment, the present invention relates to mixtures which comprise, as component 1), at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein:
[0164] R 1 is H;
[0165] R 2 is CH3;
[0166] R 3 independently selected from CH3, CHF2 in each case;
[0167] R 4 is H;
[0168] R 5 is independently selected from CH3 in each case;
[0169] R 6 is independently selected from CH3 in each case;
[0170] X is independently selected from F, Cl, CH3, OCH3 in each case;
[0171] n is 1, 2.
[0172] In one embodiment, the invention relates to mixtures which comprise, as component 1), at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein:
[0173] R 1 is H;
[0174] R 2 is CH3;
[0175] R 3 is independently selected from CH3, CHF2 in each case;
[0176] R 4 is H;
[0177] R 5 and R 6 together with the C atom to which they are bonded form C3-C6-cycloalkyl;
[0178] X is independently selected from F, Cl, CH3, OCH3 in each case;
[0179] n is 1, 2.
[0180] Particularly preferred active compounds I are selected from the group consisting of: compounds I.A to I.Z.J:
[0181] I.A: 4-[6-(difluoromethyl)-5-methyl-3-pyridyl]-7,8-difluoro-2,2-dimethyl-1,3-benzoxazine
[0182] I.B: 4-[6-(difluoromethyl)-5-methyl-3-pyridyl]-8-fluoro-2,2-dimethyl-1,3-benzoxazine
[0183] I.C: 4-[6-(difluoromethyl)-5-methyl-3-pyridyl]-8-fluoro-7-methoxy-2,2-dimethyl-1,3-benzoxazine
[0184] I.D: 8-Chloro-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-2,2-dimethyl-1,3-benzoxazine
[0185] I.E: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0186] I.F: 4-(5,6-Dimethyl-3-pyridinyl)-7,8-dimethyl-spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0187] I.G: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-2-isobutyl-2-methyl-1,3-benzoxazine
[0188] I.H: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-7-methoxy-spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0189] I.I: 7-Chloro-4-(5,6-dimethyl-3-pyridinyl)-8-fluoro-2,2-dimethyl-1,3-benzoxazine
[0190] I.J: 4-(5,6-Dimethyl-3-pyridinyl)-7,8-difluoro-2,2-dimethyl-1,3-benzoxazine
[0191] I.K: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-7,8-dimethyl-spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0192] I.L: 7-Chloro-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-2,2-dimethyl-1,3-benzoxazine
[0193] I.M: 4-(5,6-Dimethyl-3-pyridinyl)-7-methoxy-2,2-dimethyl-1,3-benzoxazine
[0194] I.N: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-7-methoxy-2,2-dimethyl-1,3-benzoxazine
[0195] I.O: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-7-methoxy-spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0196] I.P: 2-Benzyl-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-2-methyl-1,3-benzoxazine I.Q: 4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-7-methoxy-2,2,8-trimethyl-1,3-benzoxazine
[0197] I.R: 4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-7-fluoro-2,2-dimethyl-1,3-benzoxazine
[0198] I.S: 4-(5,6-Dimethyl-3-pyridinyl)-7-fluoro-2,2-dimethyl-1,3-benzoxazine
[0199] I.T: 2-Benzyl-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-2-methyl-1,3-benzoxazine
[0200] I.U: 8-Chloro-2,2-dimethyl-4-[5-methyl-6-(trifluoromethyl)-3-pyridinyl]-1,3-benzoxazine
[0201] I.V: 8-Bromo-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0202] I.W: 4-(5,6-Dimethyl-3-pyridinyl)-2-isobutyl-2-methyl-1,3-benzoxazine
[0203] I.X: 4-(5,6-Dimethyl-3-pyridinyl)-2-ethyl-2-methyl-1,3-benzoxazine
[0204] I.Y: 8-Chloro-4-(5-chloro-6-methyl-3-pyridinyl)spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0205] I.Z: 4-(5,6-Dimethyl-3-pyridinyl)spiro[1,3-benzoxazine-2,1'-cyclobutane]
[0206] I.Z.A: 4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-2,2,7-trimethyl-1,3-benzoxazine
[0207] I.Z.B: 7-(Difluoromethoxy)-4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-2,2-dimethyl-1,3-benzoxazine
[0208] I.Z.C: 4-[6-(difluoromethyl)-5-methyl-3-pyridinyl]-8-fluoro-2,2-dimethyl-1,3-benzoxazine-7-carbonitrile
[0209] I.Z.D: 4-[6-(Difluoromethyl)-5-methyl-3-pyridinyl]-7-(difluoromethylthio)-8-fluoro-2,2-dimethyl-1,3-benzoxazine
[0210] I.Z.E: 4-(6-(Difluoromethyl)-5-methylpyridin-3-yl)-7-methoxy-2,2,8-trimethyl-2H-benzo[e][1,3]oxazine
[0211] I.Z.F: 4-(5,6-Dimethylpyridin-3-yl)-7-methoxy-2,2,8-trimethyl-2H-benzo[e][1,3]oxazine
[0212] I.Z.G: 7-(Difluoromethoxy)-4-(5,6-dimethylpyridin-3-yl)-2,2,8-trimethyl-2H-benzo[e][1,3]oxazine
[0213] I.Z.H: 7-(Difluoromethoxy)-4-(6-(difluoromethyl)-5-methylpyridin-3-yl)-2,2,8-trimethyl-2H-benzo[e][1,3]oxazine
[0214] I.Z.I: 4-(6-(Difluoromethyl)-5-methylpyridin-3-yl)-7-methoxy-8-methylspiro[benzo[e][1,3]oxazine-2,1'-cyclobutane]
[0215] I.Z.J: 4-(5,6-Dimethylpyridin-3-yl)-7-methoxy-8-methylspiro[benzo[e][1,3]oxazine-2,1'-cyclobutane]
[0216] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the complex III inhibitors at the Q o site of group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.10), (A.1.11), (A.1.12), (A.1.14), (A.1.17), (A.1.19), (A.1.25), (A.1.34), (A.1.35) and (A.1.35).
[0217] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the complex III inhibitors at the Q oComplex III inhibitors at the site, more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.11), (A.1.12), (A.1.14), (A.1.16), (A.1.17).
[0218] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the complex III inhibitors in group A) at Q i Complex III inhibitors at the site, more preferably selected from compounds (A.2.1), (A.2.3), (A.2.4) and (A.2.5); particularly selected from (A.2.3), (A.2.4), (A.2.5) and (A.2.6).
[0219] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the complex II inhibitors in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.8), (A.3.9), (A.3.10), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.19), (A.3.21), (A.3.22), (A.3.23), (A.3.28), (A.3.29) and (A.3.31).
[0220] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the other respiratory inhibitors in group A), more preferably selected from compound (A.4.5).
[0221] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.12), (B.1.15), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), ((B.1.38), (B.1.44) and (B.1.46).
[0222] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the δ14-reductase inhibitors in group B), more preferably (B.2.4).
[0223] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the 3-ketoreductase inhibitors of group B), more preferably (B.3.1).
[0224] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from the phenylamide and acylamino acid fungicides of group C), more preferably selected from compounds (C.1.4), (C.1.5), (C.2.1); in particular (C.1.4).
[0225] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group D), more preferably selected from compounds (D.1.4), (D.1.5), (D.2.3), (D.2.5) and (D.2.6).
[0226] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3).
[0227] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group F), more preferably selected from compounds (F.1.2), (F.1.3) and (F.1.5).
[0228] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group G), more preferably selected from compounds (G.1.4), (G.3.1) and (G.5.1).
[0229] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group H), more preferably selected from compounds (H.1.2), (H.1.4), (H.1.5), (H.1.6), (H.1.7), (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.3.2), (H.3.4), (H.3.5), (H.3.10), (H.4.2), (H.4.9); particularly selected from (H.1.5), (H.2.2), (H.2.5), (H.3.2), (H.4.9).
[0230] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group I), more preferably selected from compounds (I.1.1), (I.2.1), (I.2.2), (I.2.3) and (I.2.4).
[0231] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group J), more preferably selected from compounds (J.1.2), (J.1.3), (J.1.4), (J.1.5), (J.1.8), (J.1.12).
[0232] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group K), more preferably selected from compounds (K.1.13), (K.1.47) and (K.1.54).
[0233] Also preferred is a mixture comprising a biopesticide as pesticidal agent II (component 2), said biopesticide being selected from groups L1), L3) to L5), preferably selected from the strains represented above as (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L.1.27), (L.1.32), (L.1.46 - L.1.56), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) and (L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for treating propagation material, i.e., for seed treatment purposes, and are equally suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as monocotyledonous plants (e.g., cereals, maize) and dicotyledonous plants (e.g., vegetables and leguminous plants such as soybeans).
[0234] Also preferred are mixtures comprising a biopesticide as pesticidal agent II (component 2), the biopesticide being selected from group L1), L3) and L4), preferably selected from those denoted above as (L1.1), (L1.2), (L1.3), (L1.6), (L1.7), (L1.9), (L1.11), (L1.12), (L1.13), (L1.14), (L1.15), (L1.17), (L1.18), (L1.22), (L1.23), (L1.24), (L1.25), (L1.26), (L1.27), (L1.46), (L1.47), (L1.48), (L1.49), (L1.50), (L1.51), (L1.52), (L1.53), (L1.54), (L1.55), (L1.56), (L2.2); (L3.2), (L3.3), (L3.4), (L3.5), (L3.6), (L3.7), (L3.8), (L3.10), (L3.11), (L3.12), (L3.13), (L3.14), (L3.15), (L3.18), (L3.19); (L4.2), even more preferably selected from (L1.2), (L1.7), (L1.11), (L1.13), (L1.14), (L1.15), (L1.18), (L1.23), (L3.3), (L3.4), (L3.6), (L3.7), (L3.8), (L3.10), (L3.11), (L3.12), (L3.15) and (L4.2). These mixtures are particularly suitable for foliar and seed treatment.
[0235] Also preferred are mixtures comprising at least one active compound as component 2), the at least one active compound being selected from group M), more preferably selected from the compounds (M1.6), (M1.24), (M1.25), (M1.28), (M1.29), (M1.30).
[0236] Also preferred are mixtures comprising at least one active compound as component 2), the at least one active compound being selected from group N), more preferably selected from the compounds (N7.3), (N7.4), (N7.5), (N13.13).
[0237] Also preferred is a mixture comprising at least one active compound as component 2), said at least one active compound being selected from group O), more preferably selected from compounds (O.2.4), (O.4.5), (O.4.7), (O.4.8), (O.5.1), (O.26.2), (O.27.17), (O.27.101), (O.27.102).
[0238] Particularly preferred are the following binary mixtures A1-1 to A1-805 listed in Table A1, in which compound I (component 1, the group represented by the expression "(I)" consisting of compounds I.A, I.B, I.C) and a pesticidal agent II (component 2) selected from groups A) to O) as defined herein, for example, (A.1.1) or azoxystrobin, in mixture A-1).
[0239] Table A1:
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254] In one embodiment, the weight ratio of Compound I to Compound II in mixtures A1-1 to A1-805 of Table A is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example, 3:1, 1:1 or 1:3.
[0255] Table A2: Mixtures A2-1 to A2-805 are defined as mixtures A1-1 to A1-805 of Table A1, wherein Compound I.A in each mixture is replaced by Compound I.B; and wherein the weight ratio of Compound I.B to Compound II is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example, 3:1, 1:1 or 1:3.
[0256] Table A3: Mixtures A3-1 to A3-805 are defined as mixtures A1-1 to A1-805 of Table A1, wherein Compound I.A in each mixture is replaced by Compound I.C; and wherein the weight ratio of Compound I.C to Compound II is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example, 3:1, 1:1 or 1:3.
[0257] For use in seed treatment, the following binary mixtures A5-1 to A5-93 listed in Table A5 are particularly preferred, wherein Compound I (Component 1, the group represented by the expression "(I)" consisting of Compound I.A, I.B, I.C) and a pesticidal agent II selected from the groups A) to O) as defined herein (Component 2, for example, (A.1.1) or azoxystrobin, in mixture A-1).
[0258] Table A5
[0259]
[0260]
[0261]
[0262] In one embodiment, the weight ratio of Compound I to Compound II in mixtures A5-1 to A5-92 of Table A5 is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example, 3:1, 1:1 or 1:3.
[0263] Table A6: Mixtures A6-1 to A6-92 are defined as mixtures A5-1 to A5-92 of Table A5, wherein compound I.A in each mixture is replaced by compound I.B; and wherein the weight ratio of compound I.B to compound II is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example 3:1, 1:1 or 1:3.
[0264] Table A7: Mixtures A7-1 to A7-92 are defined as mixtures A7-1 to A7-92 of Table A5, wherein compound I.A in each mixture is replaced by compound I.C; and wherein the weight ratio of compound I.C to compound II is between 100:1 and 1:100, preferably between 50:1 and 1:50, more preferably between 20:1 and 1:20, particularly between 5:1 and 1:5; for example 3:1, 1:1 or 1:3.
[0265] It may be preferred that, in addition to at least one compound I and at least one compound II, the above binary mixtures further comprise at least one further active compound III as component 3), thereby giving rise to ternary mixtures. Preferably, component 1) and 2) or all three components 1), 2) and 3) in these mixtures are present in synergistically effective amounts.
[0266] Accordingly, one embodiment relates to ternary mixtures which comprise as active components the following:
[0267] 1) at least one of the defined or preferably herein-defined active compound I, or its N-oxide, or an agriculturally useful salt;
[0268] and as components the following:
[0269] 2) at least one active compound II selected from the groups A) to O) as defined for component 2) in the above binary mixtures, or its N-oxide, or an agriculturally useful salt;
[0270] and as components the following:
[0271] 3) at least one active compound III selected from the groups A) to O) as defined for component 2) in the above binary mixtures, or its N-oxide, or an agriculturally useful salt;
[0272] wherein at least one active compound III of component 3) is different from at least one active compound II of component 2).
[0273] The invention further relates to a method for controlling phytopathogenic harmful fungi using the above ternary mixtures; to agrochemical compositions comprising these ternary mixtures; and to agrochemical compositions further comprising seeds which comprise these mixtures.
[0274] Active substances known as compound II or III, their preparation and their activity, for example against harmful fungi, are known (cf. http: / / www.alanwood.net / pesticides / ); these substances are commercially available. Compounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. [Canadian Journal of Plant Science] 48(6), 587 - 94, 1968; EP - A 141 317; EP - A 152 031; EP - A 226 917; EP - A 243970; EP - A256 503; EP - A 428 941; EP - A 532 022; EP - A 1 028 125; EP - A 1 035 122; EP - A1 201 648; EP - A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE102005009458; US 3,296,272; US 3,325,503; WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO99 / 27783; WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609; WO 03 / 74491; WO 04 / 49804; WO 04 / 83193; WO 05 / 120234; WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271, WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514;WO 13 / 047749, WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224, WO 11 / 135833, CN1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024, WO09094442, WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441);
[0275] Preferably, these ternary mixtures comprise a fungicidal compound as compound III, which fungicidal compounds are independently of one another selected from groups A), B), C), D), E), F), G), H), I), J), K) and O).
[0276] Also preferably, ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), which at least one active compound is selected from the complex II inhibitors of group A), more preferably from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.10), (A.1.11), (A.1.12), (A.1.14), (A.1.17), (A.1.19), (A.1.25), (A.1.34), (A.1.35) and (A.1.35); particularly preferably from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.24), (A.1.25), (A.1.26), (A.1.27), (A.1.30), (A.1.31), (A.1.32), (A.1.34), (A.1.35) and (A.1.38).
[0277] Also preferably, ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), which at least one active compound is selected from group A) at Q oComplex III inhibitors at the site, more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.11), (A.1.12), (A.1.14), (A.1.16), (A.1.17), (A.1.19), (A.1.25), (A.1.34), (A.1.35), (A.1.38).
[0278] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the complex III inhibitors at the Q i site, more preferably selected from compounds (A.2.1), (A.2.3), (A.2.4) and (A.2.5); particularly selected from (A.2.3), (A.2.4), (A.2.5) and (A.2.6).
[0279] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the complex II inhibitors of group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.8), (A.3.9), (A.3.10), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.19), (A.3.21), (A.3.22), (A.3.23), (A.3.28), (A.3.29) and (A.3.31).
[0280] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the other respiratory inhibitors of group A), more preferably selected from compounds (A.4.5) and (A.4.7).
[0281] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the C14 demethylase inhibitors of group B), more preferably selected from compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.12), (B.1.15), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.38), (B.1.44) and (B.1.46).
[0282] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the δ14 - reductase inhibitors of group B), more preferably (B.2.4).
[0283] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the 3 - keto - reductase inhibitors of group B), more preferably (B.3.1).
[0284] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from the phenylamide or acyl - amino - acid fungicides of group C), more preferably selected from compounds (C.1.4), (C.1.5) and (C.2.1); especially (C.2.1).
[0285] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group D), more preferably selected from compounds (D.1.4), (D.1.5), (D.2.3), (D.2.5) and (D.2.6).
[0286] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group E), more preferably selected from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3).
[0287] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group F), more preferably selected from compounds (F.1.2), (F.1.3) and (F.1.5).
[0288] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group G), more preferably selected from compounds (G.1.4), (G.3.1) and (G.5.1).
[0289] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group H), more preferably from the compounds (H.1.2), (H.1.4), (H.1.5), (H.1.6), (H.1.7), (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.3.2), (H.3.4), (H.3.5), (H.3.10), (H.4.2), (H.4.9) and (H.4.10); particularly preferably from (H.1.5), (H.2.2), (H.2.5), (H.3.2), (H.4.9).
[0290] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group I), more preferably from the compounds (I.1.1), (I.1.2), (I.2.1), (I.2.2), (I.2.3) and (I.2.4).
[0291] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group J), more preferably from the compounds (J.1.2), (J.1.3), (J.1.4), (J.1.5), (J.1.8), (J.1.12).
[0292] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group K), more preferably from the compounds (K.1.13), (K.1.47) and (K.1.54).
[0293] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising a biopesticide as further component 3), said biopesticide being selected from group L1), L3) to L5), preferably selected from those designated above as (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L.1.27), (L.1.32), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) and strains of (L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for treating propagation material, i.e. for seed treatment purposes, and are equally suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as monocotyledonous plants (e.g. cereals, maize) as well as dicotyledonous plants (e.g. vegetables and leguminous plants such as soya).
[0294] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising as further component 3) a biopesticide selected from group L1), L3) and L4), preferably selected from those strains designated above as (L1.1), (L.1.2), (L.1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.15) and (L.4.2). These mixtures are particularly suitable for foliar treatment.
[0295] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising as further component 3) at least one active compound selected from group M), more preferably selected from the compounds (M.1.6), (M.1.24), (M.1.25), (M.1.28), (M.1.29), (M.1.30).
[0296] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising as further component 3) at least one active compound selected from group N), more preferably selected from the compounds (N.7.3), (N.7.4), (N.7.5), (N.13.13).
[0297] Also preferred are ternary mixtures based on the binary mixtures disclosed herein and comprising at least one active compound as further component 3), said at least one active compound being selected from group O), more preferably selected from the compounds (O.2.4), (O.4.5), (O.4.7), (O.4.8), (O.5.1), (O.26.2), (O.27.17), (O.27.101), (O.27.102).
[0298] Furthermore, the invention relates to ternary mixtures which comprise the mixtures A-1 to A-805 listed in Table A above and a compound III from groups A) to O) as defined above as component 3).
[0299] Preferred are the following ternary mixtures listed in Tables B1 to B3:
[0300] Table C
[0301]
[0302]
[0303]
[0304]
[0305]
[0306] Table B1: Ternary mixtures B1-1 to B1-7503 which comprise as component 1) a compound I.A as defined herein and as components 2) and 3) a compound II and a compound III as defined in each row of Table B (for example, mixture B1-15 comprises: I.A as component 1), A.3.2 = benzovindiflupyr (see Table C above) as component 2), and A.1.1 = azoxystrobin (see Table C below) as component 3)).
[0307] In the mixtures B1-1 to B1-7503 of Table B1 according to one embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 100:1 and 1:100.
[0308] In the mixtures B1-1 to B1-7503 of Table B1 according to one embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 50:1 and 1:50.
[0309] In mixtures B1-1 to B1-7503 of Table B1 according to one embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 20:1 and 1:20.
[0310] In mixtures B1-1 to B1-7503 of Table B1 according to one embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 5:1 and 1:5.
[0311] In mixtures B1-1 to B1-7503 of Table B1 according to one embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is, for example, 3:1, 1:1 or 1:3.
[0312] Table B2: The ternary mixtures B2-1 to B2-7503 are defined as mixtures B1-1 to B1-7503 of Table B1, wherein compound I.A in each mixture is replaced by compound I.B.
[0313] In mixtures B2-1 to B2-7503 of Table B2 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 100:1 and 1:100.
[0314] In mixtures B2-1 to B2-7503 of Table B2 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 50:1 and 1:50.
[0315] In mixtures B2-1 to B2-7503 of Table B2 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 20:1 and 1:20.
[0316] In mixtures B2-1 to B2-7503 of Table B2 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 5:1 and 1:5.
[0317] In mixtures B2-1 to B2-7503 of Table B2 according to an embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is, for example, 3:1, 1:1 or 1:3.
[0318] Table B3: Mixtures B3-1 to B3-7503 are defined as mixtures B1-1 to B1-7503 of Table B1, where compound I.A in each mixture is replaced by compound I.C.
[0319] In mixtures B3-1 to B3-7503 of Table B3 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 100:1 and 1:100.
[0320] In mixtures B3-1 to B3-7503 of Table B3 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 50:1 and 1:50.
[0321] In mixtures B3-1 to B3-7503 of Table B3 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 20:1 and 1:20.
[0322] In mixtures B3-1 to B3-7503 of Table B3 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 5:1 and 1:5.
[0323] In mixtures B3-1 to B3-7503 of Table B3 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is, for example, 3:1, 1:1 or 1:3.
[0324] Table B1
[0325]
[0326]
[0327]
[0328]
[0329]
[0330]
[0331]
[0332]
[0333]
[0334]
[0335]
[0336]
[0337]
[0338]
[0339]
[0340]
[0341]
[0342]
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351]
[0352]
[0353]
[0354]
[0355]
[0356]
[0357]
[0358]
[0359]
[0360]
[0361]
[0362]
[0363]
[0364]
[0365]
[0366]
[0367]
[0368]
[0369]
[0370]
[0371]
[0372]
[0373]
[0374]
[0375]
[0376]
[0377]
[0378]
[0379]
[0380]
[0381]
[0382]
[0383]
[0384]
[0385]
[0386]
[0387]
[0388]
[0389]
[0390]
[0391]
[0392]
[0393]
[0394]
[0395]
[0396]
[0397]
[0398]
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406]
[0407]
[0408]
[0409]
[0410]
[0411]
[0412]
[0413]
[0414]
[0415]
[0416]
[0417]
[0418]
[0419]
[0420]
[0421]
[0422]
[0423]
[0424]
[0425]
[0426]
[0427]
[0428]
[0429]
[0430]
[0431]
[0432]
[0433]
[0434]
[0435]
[0436]
[0437]
[0438]
[0439]
[0440]
[0441]
[0442]
[0443]
[0444]
[0445]
[0446]
[0447]
[0448]
[0449]
[0450]
[0451]
[0452]
[0453]
[0454]
[0455] Table B4: Ternary mixtures B4-1 to B4-2436, these ternary mixtures comprising compound I.A as defined herein as component 1) and compounds II and III as defined in each row of Table B as component 2) and component 3) (for example, mixture B1-15 comprises: I.A as component 1), A.3.2 = benzovindiflupyr (see Table C above) as component 2), and A.1.1 = azoxystrobin (see Table C below) as component 3)).
[0456] In the mixtures B4-1 to B4-2436 of Table B4 according to an embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 100:1 and 1:100.
[0457] In the mixtures B4-1 to B4-2436 of Table B4 according to an embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 50:1 and 1:50.
[0458] In the mixtures B4-1 to B4-2436 of Table B4 according to an embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 20:1 and 1:20.
[0459] In the mixtures B4-1 to B4-2436 of Table B4 according to an embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is between 5:1 and 1:5.
[0460] In the mixtures B4-1 to B4-2436 of Table B4 according to an embodiment, the weight ratio of compound I.A to compound II is between 100:1 and 1:100; and the weight ratio of compound I.A to compound III is, for example, 3:1, 1:1 or 1:3.
[0461] Table B5 : Ternary mixtures B5-1 to B5-2436 are defined as the mixtures B4-1 to B4-2436 of Table B4, wherein compound I.A in each mixture is replaced by compound I.B.
[0462] In the mixtures B5-1 to B5-2436 of Table B5 according to an embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 100:1 and 1:100.
[0463] In mixtures B5-1 to B5-2436 of Table B5 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 50:1 and 1:50.
[0464] In mixtures B5-1 to B5-2436 of Table B5 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 20:1 and 1:20.
[0465] In mixtures B5-1 to B5-2436 of Table B5 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is between 5:1 and 1:5.
[0466] In mixtures B5-1 to B5-2436 of Table B5 according to one embodiment, the weight ratio of compound I.B to compound II is between 100:1 and 1:100; and the weight ratio of compound I.B to compound III is, for example, 3:1, 1:1 or 1:3.
[0467] Table B6: Mixtures B6-1 to B6-2436 of Table B6 are defined as mixtures B4-1 to B4-2436 of Table B4, wherein compound I.A in each mixture is replaced by compound I.C.
[0468] In mixtures B6-1 to B6-2436 of Table B6 according to one embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 100:1 and 1:100.
[0469] In mixtures B6-1 to B6-2436 of Table B6 according to one embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 50:1 and 1:50.
[0470] In mixtures B6-1 to B6-2436 of Table B6 according to one embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 20:1 and 1:20.
[0471] In mixtures B6-1 to B6-2436 of Table B6 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is between 5:1 and 1:5.
[0472] In mixtures B6-1 to B6-2436 of Table B6 according to an embodiment, the weight ratio of compound I.C to compound II is between 100:1 and 1:100; and the weight ratio of compound I.C to compound III is, for example, 3:1, 1:1 or 1:3.
[0473] Table B 4
[0474]
[0475]
[0476]
[0477]
[0478]
[0479]
[0480]
[0481]
[0482]
[0483]
[0484]
[0485]
[0486]
[0487]
[0488]
[0489]
[0490]
[0491]
[0492]
[0493]
[0494]
[0495]
[0496]
[0497]
[0498]
[0499]
[0500]
[0501]
[0502]
[0503]
[0504]
[0505]
[0506]
[0507]
[0508]
[0509]
[0510]
[0511]
[0512]
[0513]
[0514]
[0515]
[0516]
[0517]
[0518]
[0519]
[0520]
[0521]
[0522]
[0523]
[0524]
[0525]
[0526]
[0527]
[0528]
[0529]
[0530]
[0531]
[0532]
[0533]
[0534]
[0535]
[0536]
[0537]
[0538]
[0539]
[0540]
[0541]
[0542]
[0543]
[0544]
[0545]
[0546]
[0547]
[0548]
[0549]
[0550] The binary and ternary mixtures according to the invention and their agrochemical compositions can also be present as a premix with other active substances (such as with herbicides, insecticides, growth regulators, fungicides or alternatively with fertilizers) in the form of their use as fungicides, or, if appropriate, until immediately prior to use (tankmix).
[0551] Mixing the active compounds I, II and III in the form of their use as fungicides and the compositions comprising the mixtures with other fungicides respectively in many cases results in an extension of the fungicidal activity spectrum obtained or in the prevention of the development of fungicide resistance. Furthermore, in many cases, a synergistic effect is obtained.
[0552] Compounds of formula I according to the invention or compositions comprising said compounds and mixtures comprising said compounds and compositions are each suitable as fungicides. Their notable feature is their outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which are in particular derived from the following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example but not limited to the following genera: Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Plectosphaerella; Basidiomycota (Basidiomycetes), for example but not limited to the following genera: Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example but not limited to the following genera: Chytridiales, and Synchytrium; Deuteromycetes (synonym Fungi imperfecti), for example but not limited to the following genera: Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (synonym Oomycetes), for example but not limited to the following genera: Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, for example but not limited to Plasmodiophora; Zygomycetes, for example but not limited to Rhizopus.
[0553] Some of the compounds and compositions of formula I according to the invention are systemically active and can be used in crop protection as foliar fungicides, seed dressing fungicides and soil fungicides. In addition, they are suitable for controlling harmful fungi which occur especially in wood or in the roots of plants.
[0554] The compounds I and the compositions according to the invention are of particular importance in controlling various phytopathogenic fungi on a variety of cultivated plants such as: cereals, for example wheat, rye, barley, triticale, oats or rice; sugar beet, such as sugar beet or fodder beet; fruit, such as pomes, stone fruit or berries, for example apples, pears, plums, peaches, apricots, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, groundnuts or soybeans; cucurbits, such as pumpkins, cucumbers or melons; fibre plants, such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruit or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; laurel plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as maize, soybeans, rape, sugar cane or oil palms; maize; tobacco; nuts; coffee; tea; bananas; vines (table grape and grape juice vines); hops; turf grass; stevia (also known as stevia rebaudiana); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers; and plant propagation material, such as seeds, and crop material of these plants.
[0555] Preferably, the compounds I and their compositions are used respectively for controlling various fungi on field crops such as: potatoes, sugar beet, tobacco, wheat, rye, barley, oats, rice, maize, cotton, soybeans, rape, beans, sunflowers, coffee or sugar cane; fruit; vines; ornamental plants; or vegetables, such as cucumbers, tomatoes, kidney beans or pumpkins.
[0556] The term "plant propagation material" is to be understood as meaning all the reproductive parts of plants such as seeds and asexual plant material such as cuttings and tubers (e.g. potatoes) which can be used for the multiplication of plants. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds and other plant parts, including seedlings and young plants transplanted after germination from the soil or after emergence. These young plants can also be protected by being treated in whole or in part by soaking or drenching before transplantation.
[0557] Preferably, the plant propagation material is treated with the compounds I and their compositions respectively for controlling various fungi on cereals such as: wheat, rye, barley and oats; rice, maize, cotton and soybeans.
[0558] The term "cultivated plant" shall be understood to include plants modified by breeding, mutagenesis or genetic engineering, including but not limited to agricultural biotechnology products on the market or in development (see http: / / cera-gmc.org / , see the GM crop database therein).
[0559] Compound I and mixtures containing the same and their agrochemical compositions are particularly suitable for controlling the following plant diseases, respectively:
[0560] Species of Albugo (white rust) on ornamental plants, vegetables (e.g., A. candida), and sunflowers (e.g., A. tragopogonis); species of Alternaria (Alternaria leaf spot) on vegetables, rape (A. brassicola or A. brassicae), sugar beet (A. tenuis), fruits, rice, soybeans, potatoes (e.g., A. solani or A. alternata), tomatoes (e.g., A. solani or A. alternata), and wheat; species of Aphanomyces on sugar beet and vegetables; species of Ascochyta on cereals and vegetables, such as A. tritici (anthracnose) on wheat and A. hordei on barley; species of Bipolaris and Drechslera (sexual form: species of Cochliobolus), such as southern leaf blight (D. maydis) or northern leaf blight (B. zeicola) on maize, such as spot blotch (B. sorokiniana) on cereals and such as B. oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) (powdery mildew) on cereals (e.g., wheat or barley); Botrytis cinerea (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbages), rape, flowers, vines, forestry plants, and wheat; Bremia lactucae (downy mildew) on lettuce; species of Ceratocystis (synonym Ophiostoma) (rot or wilt) on broad-leaved and evergreen trees, such as C. ulmi (Dutch elm disease) on elm trees; species of Cercospora (Cercospora leaf spot) on maize (e.g., gray leaf spot: C. zeae-maydis), rice, sugar beet (e.g., C. beticola), sugarcane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii), and rice; C. [fulvum): leaf mold) and Cladosporium species on cereals, such as Cladosporium herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus species (asexual form: Helminthosporium of the genus Bipolaris) on maize (Cochliobolus carbonum), cereals (such as Cochliobolus sativus, anamorph: Bipolaris sorokiniana) and rice (such as Cochliobolus miyabeanus, anamorph: Helminthosporium oryzae) (leaf spot); Colletotrichum species (sexual form: Glomerella) on cotton (such as Colletotrichum gossypii), maize (such as Colletotrichum graminicola: anthracnose stalk rot), soft fruits, potato (such as Colletotrichum coccodes: black dot), bean (such as Colletotrichum lindemuthianum) and soybean (such as Colletotrichum truncatum or Colletotrichum gloeosporioides) (anthracnose); Corticium species, such as Corticium sasakii on rice (sheath blight); Corynespora cassiicola on soybean and ornamental plants (leaf spot); Cycloconium species, such as Cycloconium oleaginum on olive trees; Cylindrocarpon species on fruit trees, vines (such as Cylindrocarpon liriodendri, sexual form: Neonectria liriodendri: Black Foot Disease) and ornamental plants (such as fruit tree canker or young vine decline, sexual form: Nectria or Neonectria species); Dematophora necatrix on soybean (sexual form: Rosellinia necatrix) (root and stem rot); Diaporthe species, such as Diaporthe phaseolorum on soybean (damping-off); Diaporthe species on maize, cereals such as barley (such as D.species of Drechslera (synonym Helminthosporium, teleomorph: Pyrenophora) on barley (e.g., Drechslera teres), oats (e.g., Drechslera avenae), rye (e.g., Drechslera secalis), wheat (e.g., Drechslera tritici-repentis: tan spot), rice, and turfgrass; Esca (dieback, apoplexy) on vines, caused by Formitiporia punctata (synonym Phellinus punctata), F. mediterranea, Phaeomoniella chlamydospora (formerly known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum, and / or Botryosphaeria obtusa; species of Elsinoe on pome fruit (E. pyri), soft fruit (E. veneta: anthracnose), and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; species of Epicoccum on wheat (black mold); Erysiphe betae on sugar beet, and species of Erysiphe on vegetables such as peas (e.g., E. pisi), cucurbits (e.g., E. cichoracearum), cabbage, and oilseed rape (e.g., E. cruciferarum) (powdery mildew); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines, and ornamental wood; species of Exserohilum (synonym Helminthosporium) on maize (e.g., Exserohilum turcicum); species of Fusarium (teleomorph: Gibberella) on a variety of plants (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum on cereals (e.g., wheat or barley).culmorum) (root rot, scab or head blight), Fusarium oxysporum on tomatoes, Fusarium solani on soybeans (f.sp. glycines, new synonym Fusarium virguliforme) and F. tucumaniae and F. brasiliense (both causing sudden death syndrome), and Fusarium verticillioides on corn; Gaeumannomyces graminis on cereals (e.g., wheat or barley) and corn (take-all); Gibberella species on cereals (e.g., Gibberella zeae) and rice (e.g., Gibberella fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and Glomerella gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii on vines (black rot); Gymnosporangium species on Rosaceae plants and junipers, e.g., Gymnosporangium sabinae on pears (rust); Helminthosporium species on corn, cereals and rice (synonym Drechslera, teleomorph: Cochliobolus); Hemileia species, e.g., Hemileia vastatrix on coffee (coffee leaf rust); Isariopsis clavispora on vines (synonym Cladosporium vitis); Macrophomina phaseolina on soybeans and cotton (synonym Macrophomina phaseoli) (root and stem rot); Microdochium nivale on cereals (e.g., wheat or barley) (synonym Fusarium nivale) (pink snowmold); Microsphaera diffusa on soybeans (powdery mildew); Monilinia species on stone fruits and other Rosaceae plants, e.g., Monilinia laxa, Monilinia fructigenafructicola) and Monilinia fructigena (flower and twig blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits and groundnuts, such as Mycosphaerella graminicola on wheat (anamorph: Septoria tritici: Septoria blotch), or Mycosphaerella fijiensis on bananas (black Sigatoka disease); Peronospora species on cabbages (e.g. Peronospora brassicae), oilseed rape (e.g. Peronospora parasitica), onions (e.g. Peronospora destructor), tobacco (Peronospora tabacina) and soybeans (e.g. Peronospora manshurica) (downy mildew); Phakopsora pachyrhizi and Phakopsora meibomiae on soybeans (soybean rust); Phialophora species, such as on vines (e.g. Phialophora tracheiphila and Phialophora tetraspora) and soybeans (e.g. Phialophora gregata: stem rot); Phoma lingam on oilseed rape and cabbages (root and stem rot) and Phoma betae on sugar beet (root rot, leaf spot and damping-off); Phomopsis species on sunflowers, vines (e.g. Phomopsis viticola: cane and leaf spot) and soybeans (e.g. stem rot: Phomopsis phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis on maize (brown spot); Phytophthora species on a variety of plants (wilting, root, leaf, fruit and stem rot), such as red peppers and gourds (e.g. Phytophthora capsici), soybeans (e.g. Phytophthora megasperma, synonym Phytophthora sojae), potatoes and tomatoes (e.g. Phytophthora infestans: late blight) and broad-leaved trees (e.g. Phytophthora ramorum: sudden oak death); Plasmodiophora brassicae on cabbages, oilseed rape, turnips and other plants (club root); Plasmopara species, such as Plasmopara viticola on vinesPlasmopara viticola (downy mildew of grapevine) and Peronospora halstedii on sunflowers; Podosphaera species (powdery mildew) on Rosaceae plants, hops, pome fruits and soft fruits, such as Podosphaera leucotricha on apples; Polymyxa species, such as Polymyxa graminis on cereals such as barley and wheat and Polymyxa betae on sugar beet, and virus diseases transmitted thereby; Pseudocercosporella herpotrichoides (eyespot, sexual form: Tapesia yallundae) on cereals such as wheat or barley; Pseudoperonospora (downy mildew) on various plants, such as Pseudoperonospora cubensis on cucurbits or Pseudoperonospora humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, such as Puccinia triticina (brown rust or leaf rust), Puccinia striiformis (strip rust or yellow rust), Puccinia hordei (dwarf rust), Puccinia graminis (stem rust or black rust) or Puccinia recondita (brown rust or leaf rust) on cereals such as wheat, barley or rye, Puccinia kuehnii (citrus rust) on sugarcane and Puccinia asparagi on asparagus; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or Pyrenophora teres (net blotch) on barley; Pyricularia species, such as Pyricularia oryzae (sexual form: Magnaporthe grisea: rice blast) on rice, and Pyricularia grisea on turfgrass and cereals; Pythium species (damping-off) on turfgrass, rice, maize, wheat, cotton, rape, sunflowers, soybeans, sugar beet, vegetables and various other plants (e.g., Pythium ultimum or Pythiumspecies of Rhizoctonia on cotton, rice, potato, turfgrass, corn, rape, potato, sugar beet, vegetables and many other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice, or Rhizoctonia cerealis (Rhizoctonia spring leaf blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberry, carrot, cabbage, vine and tomato; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; species of Sclerotinia (stem rot or white mold) on vegetables and field crops such as rape, sunflower (e.g., Sclerotinia sclerotiorum) and soybean (e.g., Sclerotium rolfsii or Sclerotinia sclerotiorum); species of Septoria on various plants, such as Septoria glycines (brown spot) on soybean, Septoria tritici (Septoria leaf blotch) on wheat, and Septoria nodorum (synonym Stagonospora nodorum (Stagonospora leaf blotch)) on cereals; Uncinula necator (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri) on vine; species of Setospaeria on corn (e.g., Setosphaeria turcicum, synonym Helminthosporium turcicum) and turfgrass (leaf blight); species of Sphacelotheca on corn (e.g., Sphacelotheca reiliana: head smut), sorghum and sugarcane (smut); Sphaerotheca fuliginea (powdery mildew) on gourd; Spongospora subterranea (powdery scab) on potato and the virus disease transmitted thereby; species of Stagonospora on cereals, such as Stagonospora nodorum on wheat (S.nodorum) (Septoria leaf blotch, teleomorph: Leptosphaeria nodorum [synonym Phaeosphaeria nodorum]); Synchytrium endobioticum on potatoes (potato wart disease); Taphrina species, such as Taphrina deformans on peaches (leaf curl) and Taphrina pruni on plums (plum pocket); Thielaviopsis species on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), such as Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), such as Tilletia tritici on wheat (synonym Tilletia caries, common bunt) and Tilletia controversa on wheat (dwarf bunt); Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, such as Urocystis occulta on rye (stem smut); Uromyces species on vegetables such as kidney beans (e.g., Uromyces appendiculatus, synonym Uromyces phaseoli) and sugar beets (e.g., Uromyces betae) (rust); Ustilago species on cereals (e.g., Ustilago nuda and Ustilago avenae), maize (e.g., Ustilago maydis: corn smut) and sugar cane (loose smut); Venturia species on apples (e.g., Venturia inaequalis) and pears (scab); and Verticillium species on a variety of plants such as fruit and ornamental plants, vines, soft fruits, vegetables and field crops (wilt), such as Verticillium dahliae on strawberries, oilseed rape, potatoes and tomatoes.
[0561] In a preferred embodiment, compound I, mixtures thereof with other active compounds as defined herein, and compositions thereof are particularly suitable, respectively, for controlling the following plant diseases: Puccinia species (rusts) on various plants, such as, for example but not limited to, Puccinia triticina (brown rust or leaf rust), Puccinia striiformis (stripe rust or yellow rust), Puccinia hordei (dwarf rust), Puccinia graminis (stem rust or black rust), or Puccinia recondita (brown rust or leaf rust) on cereals such as wheat, barley or rye, and species of Phakopsora on various plants, in particular Phakopsora pachyrhizi and Phakopsora meibomiae (soybean rust) on soybean.
[0562] Compound I and mixtures containing it, as well as its agrochemical compositions, are particularly suitable, respectively, for controlling the following plant diseases which are particularly related to seeds:
[0563] Alternaria species on maize and wheat (seed-borne diseases); Aspergillus species on maize (seed-borne diseases); Claviceps on cereals (ergot disease); Cochliobolus species (anamorph: Helminthosporium) on maize (Cochliobolus carbonum) and cereals (e.g., Cochliobolus sativus) (leaf spot diseases); Colletotrichum species (teleomorph: Glomerella) on maize (anthracnose); Fusarium species (teleomorph: Gibberella) (wilt, root or stem rot diseases), such as Fusarium graminearum or Fusarium culmorum on cereals (e.g., wheat or barley) (root rot, scab or head blight), Fusarium avenaceum on maize and wheat, Fusarium oxysporum on maize, Fusarium proliferatum on maize, Fusarium subglutinans on maize, Fusarium temperatum on maize, Fusarium solani f. sp. glycines causing sudden death syndrome on soybean (Fusarium solani f. sp. glycines, new synonym of Phytophthora sojae), and Fusarium verticillioides on maize; Gaeumannomyces graminis on cereals (e.g., wheat or barley) and maize (take-all disease); Helminthosporium species (synonym Exserohilum, teleomorph: Cochliobolus) on maize; Microdochium nivale (synonym Fusarium nivale) on cereals (e.g., wheat or barley) (pink snow mold); Penicillium species on maize (seed-borne diseases); Phoma lingam on rape and cabbage (root and stem rot); Phomopsis species on soybean (e.g., stem rot: Phomopsis phaseoli, teleomorph: Diaporthe phaseolorum); Phytophthora species (wilt, root, leaf, fruit and stem rot diseases), soybean (e.g., Phytophthora sojae); Puccinia species (rust diseases), e.g., Puccinia striiformis on cereals, such as wheat, barley or rye (strip rust or yellow rust), Puccinia graminis (stem rust or black rust); Pyrenophora graminea on barley (anamorph: Drechslera graminea) (barley leaf stripe rust) or Pyrenophora teres on barley (net blotch); Pythium species (damping-off), e.g., Pythium ultimum on maize, Pythium aphanidermatum on soybean, Pythium arrhenomanes on wheat, Pythiumirregular); Rhizoctonia species on cotton, rice, potato, turf grass, maize, oilseed rape, potato, sugar beet, vegetables and a variety of other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice or Rhizoctonia cerealis (Rhizoctonia spring leaf blight) on wheat or barley; Sclerotinia species on soybean (stem rot or white mold) (such as Sclerotinia sclerotiorum or Sclerotinia minor); Sphacelotheca species on maize (smut) (such as Sphacelotheca reiliana: head smut); Tilletia species on wheat, such as Tilletia caries (common bunt of wheat) and Tilletia controversa (dwarf bunt of wheat); Typhula incarnata (grey snow mold) on barley or wheat; Urocystis species, such as Urocystis occulta (stem smut) on rye; Ustilago species on cereals (such as Ustilago nuda) and wheat (such as U. lingam) (loose smut).
[0564] In a preferred embodiment, compound I, its mixtures with other active compounds as defined herein and their compositions are particularly suitable for controlling the following plant diseases, respectively:
[0565] Alternaria species on maize and wheat (seed-borne diseases); Aspergillus species on maize (seed-borne diseases); Fusarium species (teleomorph: Gibberella) (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), Fusarium avenaceum on maize and wheat, Fusarium oxysporum on maize, Fusarium proliferatum on maize, Fusarium subglutinans on maize, Fusarium solani f. sp. glycines causing sudden death syndrome on soybean (new synonym: Phytophthora sojae), and Fusarium verticillioides on maize; Gaeumannomyces graminis on cereals (e.g. wheat or barley) and maize (take-all); Microdochium nivale (synonym: Fusarium nivale) on cereals (e.g. wheat or barley) (pink snow mold); Penicillium species on maize (seed-borne diseases); Phoma lingam on oilseed rape and cabbage (root and stem rot); Phytophthora species (wilt, root, leaf, fruit and stem rot), e.g. Phytophthora sojae on soybean; Pyrenophora graminea (anamorph: Drechslera graminea) on barley (barley leaf stripe) or Pythium species (damping-off), such as Pythium ultimum on maize, Pythium aphanidermatum on soybean, Pythium irregulare on wheat, Pythium diclinum on wheat; Rhizoctonia species on cotton, rice, potato, turfgrass, maize, oilseed rape, potato, sugar beet, vegetables and many other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice, or Rhizoctonia cerealis on wheat or barley (Rhizoctonia spring leaf blight); Sclerotinia species on soybean (stem rot or white mold) (e.g. Sclerotinia sclerotiorum or Sclerotinia minor); Sphacelotheca species on maize (smut) (e.g. Sphacelotheca reiliana: head smut); Tilletia species on wheat, such as Tilletia caries (common bunt of wheat) and Tilletia controversa (dwarf bunt of wheat); Ustilago species on cereals (e.g. Ustilago nuda) and wheat (e.g. Ustilago lingam) (loose smut).
[0566] In a most preferred embodiment, compound I, its mixtures with other active compounds as defined herein and its compositions are particularly suitable for controlling the following plant diseases, respectively:
[0567] Species of Fusarium (teleomorph: Gibberella) (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), Fusarium solani f.sp. glycines (Fusarium glycines, new synonym: Phytophthora sojae) causing sudden death syndrome on soybeans; Microdochium nivale (synonym: Fusarium nivale) (pink snow mold) on cereals (e.g. wheat or barley); species of Pythium (damping-off), such as Pythium ultimum on maize; species of Rhizoctonia on cotton, rice, potato, turfgrass, maize, oilseed rape, potato, sugar beet, vegetables and many other plants, such as Rhizoctonia solani (root and stem rot) on soybeans, Rhizoctonia solani (sheath blight) on rice or Rhizoctonia cerealis (Rhizoctonia spring leaf blight) on wheat or barley; species of Sphacelotheca on maize (smut) (e.g., Sphacelotheca reiliana: head smut); species of Tilletia on wheat, such as Tilletia caries (common bunt of wheat) and Tilletia controversa (dwarf bunt of wheat).
[0568] Mixtures A1-1 to A1-805 as defined above are suitable for controlling grey mold and white mold, in particular species of Botrytis (Botrytis species / Botrytis spp.) and Sclerotinia (Sclerotinia species / Sclerotinia spp.).
[0569] Mixtures A2-1 to A2-805 as defined above are suitable for controlling grey mold and white mold, in particular species of Botrytis and Sclerotinia.
[0570] Mixtures A3-1 to A3-805 as defined above are suitable for controlling grey mold and white mold, in particular species of Botrytis and Sclerotinia.
[0571] The mixtures A1-1 to A1-805 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, especially blast caused by Pyricularia grisea (formerly known as Pyricularia oryzae), and brown spot (Cochliobolus miyabeanus, formerly known as Helminthosporium oryzae; Drechslera oryzae; Bipolaris oryzae); dirty panicle, including Cercopsora oryzae, Curvularia lunata, Trichoconis padwickii, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (formerly known as Corticium sasakii)); bakanae disease of rice (Fusarium fujikuroi = Giberella fujikuroi).
[0572] The mixtures A2-1 to A2-805 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, especially blast caused by Pyricularia grisea (formerly known as Pyricularia oryzae), and brown spot (Cochliobolus miyabeanus, formerly known as Helminthosporium oryzae; Drechslera oryzae; Bipolaris oryzae); dirty panicle, including Cercopsora oryzae, Curvularia lunata, Trichoconis padwickii, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (formerly known as Corticium sasakii)); bakanae disease of rice (Fusarium fujikuroi = Giberella fujikuroi).
[0573] The mixtures A3-1 to A3-805 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, especially blast caused by Pyricularia grisea (formerly known as Pyricularia oryzae), and brown spot (Cochliobolus miyabeanus, formerly known as Helminthosporium oryzae; Drechslera oryzae; Bipolaris oryzae); dirty panicle, including Cercopsora oryzae, Curvularia lunata, Trichoconis padwickii, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (formerly known as Corticium sasakii)); bakanae disease of rice (Fusarium fujikuroi = Giberella fujikuroi).
[0574] The mixtures A1-1 to A1-805 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0575] The mixtures A2-1 to A2-805 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0576] The mixtures A3-1 to A3-805 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0577] The mixtures A1-1 to A1-805 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals, and potatoes and leafy vegetables, in particular Rhizoctonia solani.
[0578] The mixtures A2-1 to A2-805 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals, and potatoes and leafy vegetables, in particular Rhizoctonia solani.
[0579] The mixtures A3-1 to A3-805 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals, and potatoes and leafy vegetables, in particular Rhizoctonia solani.
[0580] The mixtures A1-1 to A1-805 as defined above are suitable for controlling storage complex-infection diseases in pome and stone fruits, in particular species of Gloeosporium, Penicillium, Botrytis, Monilia, and Monilinia, Sphaeropsis, Neofabraea, Mucor.
[0581] The mixtures A2-1 to A2-805 as defined above are suitable for controlling storage complex-infection diseases in pome and stone fruits, in particular species of Gloeosporium, Penicillium, Botrytis, Monilia, and Monilinia, Sphaeropsis, Neofabraea, Mucor.
[0582] The mixtures A3-1 to A3-805 as defined above are suitable for controlling storage complex-infection diseases in pome and stone fruits, especially species of Gloeosporium, Penicillium, Botrytis, Monilia, and Sclerotinia, species of Cylindrosporium, species of Hymenoscyphus, species of Mucor.
[0583] The mixtures A1-1 to A1-805 as defined above are suitable for controlling different soil- and seed-borne pathogens, especially species of Fusarium (Fusarium spp.), such as Fusarium culmorum, Fusarium graminearum, Microdochium nivale, species of Cochliobolus, species of Ustilago, species of Septoria, species of Pyrenophora, species of Cladosporium, species of Rhynchosporium, species of Tilletia, and Rhizoctonia solani.
[0584] The mixtures A2-1 to A2-805 as defined above are suitable for controlling different soil- and seed-borne pathogens, especially species of Fusarium (Fusarium spp.), such as Fusarium culmorum, Fusarium graminearum, Microdochium nivale, species of Cochliobolus, species of Ustilago, species of Septoria, species of Pyrenophora, species of Cladosporium, species of Rhynchosporium, species of Tilletia, and Rhizoctonia solani.
[0585] The mixtures A3-1 to A3-805 as defined above are suitable for controlling different soil- and seed-borne pathogens, especially species of Fusarium (Fusarium spp.), such as Fusarium culmorum, Fusarium graminearum, Microdochium nivale, species of Cochliobolus, species of Ustilago, species of Septoria, species of Pyrenophora, species of Cladosporium, species of Rhynchosporium, species of Tilletia, and Rhizoctonia solani.
[0586] The mixtures B1-1 to B1-7503 as defined above are suitable for controlling grey mould and white mould, especially species of Botrytis and Sclerotinia.
[0587] The mixtures B2-1 to B2-7503 as defined above are suitable for controlling grey mould and white mould, especially species of Botrytis and Sclerotinia.
[0588] The mixtures B3-1 to B3-7503 as defined above are suitable for controlling grey mould and white mould, especially species of Botrytis and Sclerotinia.
[0589] Mixtures B1-1 to B1-7503 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, in particular Magnaporthe oryzae (Pyricularia oryzae, previously known as Pyricularia grisea) and brown spot (Bipolaris oryzae, previously known as Cochliobolus miyabeanus; Bipolaris oryzae; Drechslera oryzae); dirty panicle, including Cercospora oryzae, Curvularia lunata, Coniothyrium oryzae, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (also known as Rhizoctonia solani); bakanae disease of rice (Fusarium fujikuroi = Gibberella fujikuroi).
[0590] Mixtures B2-1 to B2-7503 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, in particular Magnaporthe oryzae (Pyricularia oryzae, previously known as Pyricularia grisea) and brown spot (Bipolaris oryzae, previously known as Cochliobolus miyabeanus; Bipolaris oryzae; Drechslera oryzae); dirty panicle, including Cercospora oryzae, Curvularia lunata, Coniothyrium oryzae, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (also known as Rhizoctonia solani); bakanae disease of rice (Fusarium fujikuroi = Gibberella fujikuroi).
[0591] Mixtures B3-1 to B3-7503 as defined above are suitable for controlling rice leaf, neck, collar and panicle blast, in particular Magnaporthe oryzae (Pyricularia oryzae, previously known as Pyricularia grisea) and brown spot (Bipolaris oryzae, previously known as Cochliobolus miyabeanus; Bipolaris oryzae; Drechslera oryzae); dirty panicle, including Cercospora oryzae, Curvularia lunata, Coniothyrium oryzae, Sarocladium oryzae, Fusarium semitectum; sheath blight of rice (Rhizoctonia solani = Thanatephorus cucumeris (also known as Rhizoctonia solani); bakanae disease of rice (Fusarium fujikuroi = Gibberella fujikuroi).
[0592] Mixtures B1-1 to B1-7503 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0593] Mixtures B2-1 to B2-7503 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0594] Mixtures B3-1 to B3-7503 as defined above are suitable for controlling diseases of pome and stone fruits, in particular species of Venturia, Monilinia, Monilia, Alternaria, Diplocarpon mali = Marssonina coronaria.
[0595] Mixtures B1-1 to B1-7503 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals and potatoes and leafy vegetables, in particular Rhizoctonia solani.
[0596] The mixtures B2-1 to B2-7503 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals, and potatoes and leafy vegetables, especially Rhizoctonia solani.
[0597] The mixtures B3-1 to B3-7503 as defined above are suitable for controlling Rhizoctonia diseases in several crops such as turfgrass, cereals, and potatoes and leafy vegetables, especially Rhizoctonia solani.
[0598] The mixtures B1-1 to B1-7503 as defined above are suitable for controlling storage complex infections in pome and stone fruits, especially species of Gloeosporium, Penicillium, Botrytis, Monilia, and Sclerotinia, Ovularia, Hymenoscyphus, Mucor.
[0599] The mixtures B2-1 to B2-7503 as defined above are suitable for controlling storage complex infections in pome and stone fruits, especially species of Gloeosporium, Penicillium, Botrytis, Monilia, and Sclerotinia, Ovularia, Hymenoscyphus, Mucor.
[0600] The mixtures B3-1 to B3-7503 as defined above are suitable for controlling storage complex infections in pome and stone fruits, especially species of Gloeosporium, Penicillium, Botrytis, Monilia, and Sclerotinia, Ovularia, Hymenoscyphus, Mucor.
[0601] The mixtures B1-1 to B1-7503 as defined above are suitable for controlling different soil- and seed-borne pathogens, especially species of Fusarium (Fusarium spp., such as Fusarium culmorum, Fusarium graminearum), Microdochium nivale, species of Cochliobolus, Ustilago, Septoria, Pyrenophora, Cladosporium, Rhynchosporium, Tilletia, and Rhizoctonia solani).
[0602] The mixtures B2-1 to B2-7503 as defined above are suitable for controlling different soil- and seed-borne pathogens, especially species of Fusarium (Fusarium spp., such as Fusarium culmorum, Fusarium graminearum), Microdochium nivale, species of Cochliobolus, Ustilago, Septoria, Pyrenophora, Cladosporium, Rhynchosporium, Tilletia, and Rhizoctonia solani).
[0603] Mixtures B3-1 to B3-7503 as defined above are suitable for controlling different soil- and seed-borne pathogens, in particular Fusarium species (Fusarium spp.), such as Fusarium culmorum, Fusarium graminearum, Microdochium nivale, Cochliobolus species, Ustilago species, Septoria species, Pyrenophora species, Cladosporium species, Rhynchosporium species, Tilletia species, and Rhizoctonia solani).
[0604] Compound I and its compositions are also suitable for controlling harmful fungi in the protection of stored products or harvested crops and in the protection of materials, respectively.
[0605] The term "protection of materials" is to be understood as meaning the protection of technical and non-living materials such as adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fibres or fabrics against infestation and destruction by harmful microorganisms such as fungi and bacteria. In respect of the protection of wood and other materials, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma species, Ceratocystis species, Aureobasidium pullulans, Sclerophoma species, Chaetomium species, Humicola species, Petriella species, Trichurus species; Basidiomycetes, such as Coniophora species, Coriolus species, Gloeophyllum species, Lentinus species, Pleurotus species, Poria species, Serpula lacrymans and Tyromyces species; Deuteromycetes, such as Aspergillus species, Cladosporium species, Penicillium species, Trichoderma species, Alternaria species, Paecilomyces species; and Zygomycetes, such as Mucor species, and furthermore in the protection of stored products and harvested crops, the following yeast fungi are noteworthy: Candida species and Saccharomyces cerevisiae.
[0606] The treatment method according to the present invention can also be used in the field of protecting stored products or harvested products from fungal and microbial attacks. According to the present invention, the term "stored product" should be understood to mean natural substances of plant or animal origin and their processed forms, which are taken from the natural life cycle and are intended to be protected for a long time. Stored products of crop plant origin (such as plants or parts thereof), such as stalks, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed forms such as pre-dried, wetted, crushed, ground, pressed or baked (this processing is also called post-harvest treatment). Also falling under the definition of stored products is wood, whether in the form of logs, such as construction timber, transmission towers and fences, or in the form of finished products, such as furniture or objects made of wood. Stored products of animal origin are hides, leather, furs, hairs, etc. The combinations according to the present invention can prevent adverse effects such as rot, discoloration or mould. Preferably, the "stored product" should be understood to mean natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, soft fruits and citrus fruits and their processed forms.
[0607] Compound I and its compositions can be used respectively to improve the health of plants. The present invention also relates to a method for improving plant health by treating plants, their propagation materials and / or the places where plants are growing or will grow with an effective amount of Compound I and its compositions respectively.
[0608] The term "plant health" should be understood to mean the condition of plants and / or their products, which is determined by a number of indicators either individually or in combination with each other, such as yield (e.g., increased biomass and / or increased content of valuable components), plant vigour (e.g., improved plant growth and / or greener leaves ("greening effect")), quality (e.g., improved content or composition of certain components) and tolerance to abiotic and / or biotic stresses. The indicators of the plant health condition determined above may be interdependent or may influence each other.
[0609] Compounds having the formula I can exist in different crystalline variants with possibly different biological activities. They are also the subject of the present invention.
[0610] Compound I is used as such or in the form of a composition by treating fungi or plants, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms to be protected from fungal attacks with a fungicidally effective amount of the active substance. The application can be carried out before and after the plants, plant propagation materials (such as seeds), soil, surfaces, materials or rooms are infected with fungi.
[0611] Plant propagation materials can be prophylactically treated with Compound I itself or a composition containing at least one Compound I at the time of planting or transplantation or before planting or transplantation.
[0612] The present invention also relates to an agrochemical composition comprising an adjuvant and at least one compound I according to the present invention.
[0613] The agrochemical composition comprises a fungicidally effective amount of compound I. The term "effective amount" means an amount of the composition or of compound I which is sufficient to control harmful fungi on cultivated plants or on materials to be protected and which does not cause substantial damage to the plants treated. Such amounts can vary within wide ranges and depend on various factors such as the fungal species to be controlled, the cultivated plants or materials treated, the climatic conditions and the specific compound I used.
[0614] Compound I, its N-oxides and salts can be converted into agrochemical compositions of customary types, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and mixtures thereof. Examples of composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, tablets, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), tablets (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal products (e.g. LN), and gel formulations (e.g. GF) for treating plant propagation material such as seeds. These and further composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Edition, May 2008, CropLife International.
[0615] These compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
[0616] The binary or ternary mixtures of the active compounds described herein can be prepared by customary means, for example by the means given herein for the compositions of compound I, as compositions which in addition to the active ingredient also contain at least one inert ingredient (auxiliary). With regard to the customary constituents of such compositions, reference is made to the explanations given for the compositions containing compound I.
[0617] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration promoters, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezes, defoamers, colorants, tackifiers and binders.
[0618] Suitable solvents and liquid carriers are water and organic solvents such as middle to high boiling mineral oil fractions such as kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons such as toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; diols; DMSO; ketones such as cyclohexanone; esters such as lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides such as N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
[0619] Suitable solid carriers or fillers are mineral earths such as silicates, silica gels, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin such as cereal flours, bark flours, wood flours, nut shell flours, and mixtures thereof.
[0620] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).
[0621] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.
[0622] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents of alkylene oxide. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or glycerol monoesters. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.
[0623] Suitable cationic surfactants are quaternary ammonium surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or A-B-C type block polymers containing alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali metal salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethylenamine.
[0624] Suitable adjuvants are compounds which have negligible pesticidal activity or even no pesticidal activity themselves and improve the biological performance of Compound I against the target. Examples are surfactants, mineral oils or vegetable oils, and other auxiliaries. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.
[0625] Suitable thickeners are polysaccharides (such as xanthan gum, carboxymethyl cellulose), inorganic clays (organo-modified or unmodified), polycarboxylates, and silicates.
[0626] Suitable fungicides are bronopol and isothiazolone derivatives such as alkyl isothiazolinones and benzisothiazolinones.
[0627] Suitable antifreezes are ethylene glycol, propylene glycol, urea, and glycerol.
[0628] Suitable defoamers are silicones, long-chain alcohols, and salts of fatty acids.
[0629] Suitable colorants (e.g., red, blue, or green) are poorly water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (such as iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (such as alizarin, azo, and phthalocyanine colorants).
[0630] Suitable thickening agents or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological waxes or synthetic waxes, and cellulose ethers.
[0631] Examples of composition types and their preparation are:
[0632] i) Water-soluble concentrates (SL, LS)
[0633] 10 wt% - 60 wt% of Compound I and 5 wt% - 15 wt% of a wetting agent (e.g., alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g., alcohol) up to 100 wt%. The active compound dissolves upon dilution with water.
[0634] ii) Dispersible concentrates (DC)
[0635] 5 wt% - 25 wt% of Compound I and 1 wt% - 10 wt% of a dispersant (e.g., polyvinylpyrrolidone) are dissolved in an organic solvent (e.g., cyclohexanone) up to 100 wt%. A dispersion is obtained upon dilution with water.
[0636] iii) Emulsifiable concentrate (EC)
[0637] 15 wt% - 70 wt% of Compound I and 5 wt% - 10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., aromatic hydrocarbon) up to 100 wt%. The emulsion is obtained by dilution with water.
[0638] iv) Emulsion (EW, EO, ES)
[0639] 5 wt% - 40 wt% of Compound I and 1 wt% - 10 wt% of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 wt% - 40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is introduced into water up to 100 wt% with the aid of an emulsifier and made into a homogeneous emulsion. The emulsion is obtained by dilution with water.
[0640] v) Suspension (SC, OD, FS)
[0641] In a stirred ball mill, 20 wt% - 60 wt% of Compound I is ground in the presence of 2 wt% - 10 wt% of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1 wt% - 2 wt% of a thickener (e.g., xanthan gum) and water up to 100 wt% to obtain a fine suspension of the active compound. The stable suspension of the active substance is obtained by dilution with water. For FS type compositions, up to 40 wt% of a binder (e.g., polyvinyl alcohol) is added.
[0642] vi) Water-dispersible granules and water-soluble granules (WG, SG)
[0643] 50 wt% - 80 wt% of Compound I is finely ground in the presence of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate) up to 100 wt% and prepared into water-dispersible or water-soluble granules by means of technical devices (e.g., extrusion, spray tower, fluidized bed). The stable dispersion or solution of the active substance is obtained by dilution with water.
[0644] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
[0645] 50 wt% - 80 wt% of Compound I is ground in a rotor-stator mill in the presence of 1 wt% - 5 wt% of a dispersant (e.g., sodium lignosulfonate), 1 wt% - 3 wt% of a wetting agent (e.g., alcohol ethoxylate) and a solid carrier (e.g., silica gel) up to 100 wt%. The stable dispersion or solution of the active substance is obtained by dilution with water.
[0646] viii) Gels (GW, GF)
[0647] In a stirred ball mill, 5 wt% - 25 wt% of Compound I is ground in the presence of 3 wt% - 10 wt% of a dispersant (e.g., sodium lignosulfonate), 1 wt% - 5 wt% of a thickener (e.g., carboxymethyl cellulose), and water up to 100 wt% to obtain a fine active substance suspension. The stable active substance suspension is obtained by dilution with water.
[0648] ix) Microemulsions (ME)
[0649] 5 wt% - 20 wt% of Compound I is added to 5 wt% - 30 wt% of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10 wt% - 25 wt% of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 wt%. This mixture is stirred for 1 h to spontaneously form a thermodynamically stable microemulsion.
[0650] x) Microcapsules (CS)
[0651] An oil phase containing 5 wt% - 50 wt% of Compound I, 0 wt% - 40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), 2 wt% - 15 wt% of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and diacrylate or triacrylate) is dispersed into an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5 wt% - 50 wt% of Compound I according to the present invention, 0 - 40 wt% water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethylene - 4,4'-diisocyanate) is dispersed into an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1 wt% - 10 wt%. wt% is related to the total CS composition.
[0652] xi) Dustable powders (DP, DS)
[0653] 1 wt% - 10 wt% of Compound I is finely ground and thoroughly mixed with a solid carrier up to 100 wt% (e.g., finely divided kaolin).
[0654] xii) Granules (GR, FG)
[0655] 0.5 wt% - 30 wt% of Compound I is finely ground and combined with a solid carrier up to 100 wt% (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed.
[0656] xiii) Ultra-low volume liquid (UL)
[0657] 1 wt% - 50 wt% of Compound I is dissolved in an organic solvent (such as aromatic hydrocarbons) up to 100 wt%.
[0658] Composition types i) to xiii) may optionally contain additional auxiliaries, such as 0.1 wt% - 1 wt% bactericide, 5 wt% - 15 wt% antifreeze, 0.1 wt% - 1 wt% defoamer, and 0.1 wt% - 1 wt% colorant.
[0659] Agrochemical compositions generally contain an active substance by weight between 0.01% and 95%, preferably between 0.1% and 90%, more preferably between 1% and 70%, and especially between 10% and 60%. The active substance is used with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectra).
[0660] For the purpose of treating plant propagation materials, especially seeds, solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), dry powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually used. After dilution by two to ten times, the concentration of the active compound in the ready-to-use formulation of the composition under discussion is 0.01% to 60% by weight, preferably 0.1% to 40%. Application can be carried out before or during sowing. Methods for applying Compound I and its compositions to plant propagation materials, especially seeds, respectively, include dressing, coating, granulation, dusting, and soaking as well as in-furrow application methods. Preferably, Compound I or its composition is applied to plant propagation materials separately by methods that do not induce germination, such as by dressing, granulation, coating, and dusting.
[0661] When used in plant protection, depending on the type of desired effect, the amount of the active substance applied is 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, and especially 0.1 to 0.75 kg / ha.
[0662] In the treatment of plant propagation materials such as seeds, for example, by dusting, coating, or soaking, an amount of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g of the active compound is usually required per 100 kilograms of plant propagation materials (preferably seeds).
[0663] When used for the protection of materials or storage products, the amount of the active compound applied depends on the type of the field of application and the desired effect. The amount usually applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active compound per cubic meter of treated material.
[0664] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients and additional biocides (such as herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) can be added as a premix to the active substance or the composition containing it or, if appropriate, added until immediately before use (tank mixing). These reagents can be admixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.
[0665] A biocide is generally a chemical or biological agent (such as a pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial agent or disinfectant) that prevents, disables, kills or otherwise frustrates pests by its effect. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms) and microorganisms that damage property, cause nuisances, spread diseases or are vectors of diseases. The term "biocide" also includes plant growth regulators that alter the expected growth, flowering or reproduction rate of plants; defoliants that cause leaves or other foliage to fall off plants, usually to facilitate harvesting; desiccants that promote the drying of living tissue, such as the above-ground parts of unwanted plants; plant activators that activate the physiological functions of plants to defend against certain pests; safeners that reduce the unwanted herbicidal effects of biocides on crop plants; and plant growth promoters that affect the physiological functions of plants, for example to enhance plant growth, biomass, yield or any other quality parameter of the harvestable articles of crop plants.
[0666] The user generally applies the composition according to the invention by means of a pre-metering device, a knapsack sprayer, a spray tank, a spray aircraft, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and / or additional adjuvants to the desired application concentration, and thus a ready-to-use spray liquid or agrochemical composition according to the invention is obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters of the ready-to-use spray liquid are applied per hectare of agricultural usable area.
[0667] According to one embodiment, the various components of the composition according to the invention, such as the parts of a kit or the parts of a binary or ternary mixture, can be mixed by the user himself in a spray tank or any other kind of container for application (such as a seed treatment drum, a seed granulator, a knapsack sprayer) and, if appropriate, additional adjuvants can be added.
[0668] Accordingly, an embodiment of the present invention is a kit for preparing a useful pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one adjuvant; and b) a composition comprising component 2) as defined herein and at least one adjuvant; and optionally c) a composition comprising at least one adjuvant and optionally another active ingredient 3) as defined herein.
[0669] Mixing compound I or a composition comprising the same in a fungicidal use form with other fungicides in many cases results in an extension of the obtained fungicidal activity spectrum or prevents the development of fungicide resistance. In addition, in many cases, a synergistic effect is obtained.
[0670] Furthermore, the present invention relates to agrochemical compositions which comprise a mixture of at least one compound I (component 1) and at least one further active compound which is useful for plant protection (for example selected from groups A) to O)) (component 2), in particular a further fungicide, for example one or more fungicides from groups A) to K) as described above, and, if desired, a suitable solvent or solid carrier. These mixtures are of particular interest since many of them show a higher efficacy against harmful fungi at the same application rate. In addition, a mixture of compound I and at least one fungicide from groups A) to K) as described above is more effective against harmful fungi than compound I alone or a single fungicide from groups A) to K) against those fungi.
[0671] By applying compound I together with at least one active compound from groups A) to O), a synergistic effect can be obtained, i.e., an effect greater than the simple sum of the individual effects (synergistic mixture).
[0672] This can be achieved by applying compound I and at least one further active compound simultaneously, jointly (for example as a tank mix) or separately, or in succession, where the time interval between the individual applications is selected to ensure that the initially applied active compound is still present in sufficient amounts at the site of action when the further active substance is applied. The order of application is not critical for the practice of the present invention.
[0673] When applying compound I and pesticidal agent II in succession, the time between the two applications can vary, for example, between 2 hours and 7 days. Wider ranges from 0.25 hours to 30 days, preferably 0.5 hours to 14 days, in particular 1 hour to 7 days or 1.5 hours to 5 days, even more preferably 2 hours to 1 day are also possible.
[0674] In the binary mixtures and compositions according to the invention, the weight ratio of component 1) and component 2) generally depends on the properties of the active components used and is generally in the range from 1:10,000 to 10,000:1, often in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:5 to 5:1 and in particular in the range from 1:2 to 2:1.
[0675] According to a further embodiment of the binary mixtures and compositions, the weight ratio of component 1) and component 2) is generally in the range from 1000:1 to 1:1, often in the range from 100:1 to 1:1, frequently in the range from 50:1 to 1:1, preferably in the range from 20:1 to 1:1, more preferably in the range from 5:1 to 1:1 and in particular in the range from 2:1 to 1:1.
[0676] According to a further embodiment of the binary mixtures and compositions, the weight ratio of component 1) and component 2) is generally in the range from 1:1 to 1:1000, often in the range from 1:1 to 1:100, frequently in the range from 1:1 to 1:50, preferably in the range from 1:1 to 1:20, more preferably in the range from 1:1 to 1:5 and in particular in the range from 1:1 to 1:2.
[0677] In the ternary mixtures, i.e. the compositions according to the invention which comprise component 1) and component 2) and compound III (component 3), the weight ratio of component 1) and component 2) is in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:5 to 5:1 and in particular in the range from 1:2 to 2:1, and the weight ratio of component 1) and component 3) is in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:5 to 5:1 and in particular in the range from 1:2 to 2:1.
[0678] If desired, any further active component is added to component 1) in a ratio of 20:1 to 1:20.
[0679] These ratios are also suitable for the mixtures according to the invention which are applied by seed treatment.
[0680] The fungicidal action of the mixtures according to the invention can be demonstrated by the tests described below.
[0681] The percentage of the infected leaf area determined visually is converted into a efficacy in % of the untreated control.
[0682] Efficacy (E) was calculated using Abbot's formula as follows:
[0683] E=(1-α / β)·100
[0684] α corresponds to the fungicidal infection of the treated plants in %, and
[0685] β corresponds to the fungicidal infection of the untreated (control) plants in %
[0686] An efficacy of 0 means that the infection level of the treated plants corresponds to the infection level of the untreated control plants; an efficacy of 100 means that the treated plants are not infected.
[0687] The expected efficacy of active compound combinations can be calculated using the Colby formula (Colby, SR "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15 , pp. 20-22, 1967) to determine and compare with the observed efficacy.
[0688] Colby's formula:
[0689] E=x+yx·y / 100
[0690] E Expected efficacy when using a mixture of active compounds A and B at concentrations a and b, expressed as % of the untreated control
[0691] x Efficacy when active compound A is used at concentration a, expressed as % of untreated control
[0692] y Efficacy when active compound B is used at concentration b, expressed as % of the untreated control.
[0693] Micro-test
[0694] Active compounds were prepared individually as stock solutions in dimethyl sulfoxide at a concentration of 10,000 ppm.
[0695] The stock solutions were mixed in the ratios, pipetted into a microtiter plate (MTP) and diluted with water to the specified concentrations.
[0696] Example 1 - Activity against Botrytis cinerea in a microtiter plate test
[0697] Mix the stock solutions in a ratio, pipette them onto a microtiter plate (MTP), and dilute them with water to a specified concentration. Then add a spore suspension of Botrytis cinerea in an aqueous solution of biological malt or a yeast-bacterial peptone-sodium acetate solution. Place these plates in a water vapor-saturated chamber at a temperature of 18 °C. Measure the MTP at 405 nm 7 days after inoculation using an absorption photometer.
[0698]
[0699]
[0700]
[0701]
[0702]
[0703] Example 2 - Activity against Pyricularia oryzae in a microtiter plate test
[0704] Mix the stock solutions in a ratio, pipette them onto a microtiter plate (MTP), and dilute them with water to a specified concentration. Then add a spore suspension of Pyricularia oryzae in an aqueous solution of biological malt or a yeast-bacterial peptone-glycerol solution. Place these plates in a water vapor-saturated chamber at a temperature of 18 °C. Measure the MTP at 405 nm 7 days after inoculation using an absorption photometer.
[0705]
[0706]
[0707]
[0708]
[0709]
[0710] Example 3 - Activity against leaf spot on wheat caused by Septoria tritici
[0711] Mix the stock solutions in a ratio, pipette them onto a microtiter plate (MTP), and dilute them with water to a specified concentration. Then add a spore suspension of Septoria tritici in an aqueous solution of biological malt or a yeast-bacterial peptone-glycerol solution. Place these plates in a water vapor-saturated chamber at a temperature of 18 °C. Measure the MTP at 405 nm 7 days after inoculation using an absorption photometer.
[0712]
[0713]
[0714]
[0715]
[0716]
[0717]
[0718] The measured parameters are compared with the growth rate (100%) of a control variant of the inactive compound and the blank value without fungi and without the inactive compound to determine the relative growth rate (in %) of the pathogen in the corresponding active compound.
[0719] The expected efficacy of the active compound mixture is determined using the Colby formula [R.S. Colby, "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, 20 - 22 (1967)] and compared with the observed efficacy.
Claims
1. A fungicidal mixture, which fungicidal mixture comprises, as active ingredients, the following: at least one active compound of formula I, or its N-oxide, or an agriculturally useful salt, wherein R 1 is H; R 2 is, in each case independently, selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, O-C1-C6-alkyl; R 3 is, in each case independently, selected from C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C2-C6-alkynyl; R 4 is H; R 5 is, in each case independently, selected from C1-C6-alkyl, C1-C6-haloalkyl, benzyl, wherein the benzyl moiety of R 5 is unsubstituted or substituted by one to three groups R 5a independently of one another selected from the following: halogen; R 6 is, in each case independently, selected from C1-C6-alkyl, benzyl, wherein the benzyl moiety of R 6 is unsubstituted or substituted by one to three groups R 6a independently of one another selected from the following: halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl; or R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl, where the cycloalkyl may be unsubstituted or substituted by C1-C6-alkyl, C1-C6-haloalkyl; X is, in each case independently, selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl; n is 0, 1, 2 and as component the following: 2) at least one active compound II, which at least one active compound is selected from groups A) to O), or its N-oxide, or an agriculturally useful salt: A) Respiratory inhibitors - at Qo Complex III inhibitors at the site: azoxystrobin (A.1.1), cymoxanil (A.1.2), coumethoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), enoxastrobin (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyraoxystrobin (A.1.15), pyributicarb (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), pyrimethanil (A.1.19), triclopyricarb / chlorodincarb (A.1.20), fenamidone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), tetraconazole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyridaben (A.1.36), picarbutrazox (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38); - At Q i Complex III inhibitors at the site: cyazofamid (A.2.1), indaziflam (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), picoxystrobin (A.2.5), metarylpicoxamid (A.2.6); - Complex II inhibitors: carboxin (A.3.1), bixafen (A.3.2), boscalid (A.3.3), boscalid (A.3.4), oxycarboxin (A.3.5), furametpyr (A.3.6), fluxapyroxad (A.3.7), flutolanil (A.3.8), fluopyram (A.3.9), fipronil (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin oxide (A.3.14), sedaxane (A.3.15), pythiathion (A.3.16), fluxametamide (A.3.17), bixafen (A.3.18), penflufen (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), N-[2-[2-chloro - 4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), (E)-methyl 2-[2-[(5-cyano-2-methylphenoxy)methyl]phenyl]-3-methoxyprop-2-enoate (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylinden-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylinden-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylinden-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propylinden-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propylinden-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethylinden-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethylinden-4-yl]pyridine-3-carboxamide (A.3.39), triflumizole (A.3.24); - Other respiratory inhibitors: difluralin (A.4.1); nitro-phenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), dichlofluanid (A.4.6), ferimzone (A.4.7); organo-metallic compounds: triphenyltin salts, such as fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); amisulbrom (A.4.11); silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) - C14 demethylase inhibitors: Triazoles: penconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridinyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridinyl]propan-2-ol (B.1.32), fluopyram (B.1.33), ipfentrifluconazole (B.1.37), chlorfluzolam (B.1.38), (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, 2-(chloromethyl)-2-methyl -5-(p-Tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); Imidazoles: Imazalil (B.1.44), Triflumizole (B.1.45), Prochloraz (B.1.46), Triflumazole (B.1.47); Pyrimidines, Pyridines, Piperazines: Fenarimol (B.1.49), Pyrifenox (B.1.50), Triforine (B.1.51), [3-(4-Chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-Bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-Chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.55), Methyl 2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (B.1.56), Methyl 2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (B.1.57); -δ14-Reductase inhibitors: 4-Dodecyl-2,6-dimethylmorpholine (aldimorph) (B.2.1), Dodemorph (B.2.2), Dodemorph acetate (B.2.3), Fenpropimorph (B.2.4), Tridemorph (B.2.5), Fenpropidin (B.2.6), Pyracarbolid (B.2.7), Spiroxamine (B.2.8); -3-Ketoreductase inhibitors: Fenhexamid (B.3.1); -Other sterol biosynthesis inhibitors: Climbazole (B.4.1); -Other sterol biosynthesis inhibitors: Climbazole (B.4.1); C) Nucleic acid synthesis inhibitors -Phenylamide or acylamino acid fungicides: Benalaxyl (C.1.1), Benalaxyl-M (C.1.2), Benalaxyl-K (C.1.3), Metalaxyl (C.1.4), Metalaxyl-M (C.1.5), Furametpyr (C.1.6), Oxadixyl (C.1.7); - Other nucleic acid synthesis inhibitors: hymexazol (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), ethirimol besylate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8); D) Cell division and cytoskeleton inhibitors - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylthioacetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxyacetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propylbutanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propylacetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylthio-N-propylacetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylthioacetamide (D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl - Pyrazol-3-amine (D.1.16); - Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), fenpropimorph (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7), phenamacril (D.2.8); E) Amino acid and protein synthesis inhibitors - Methionine synthesis inhibitors: cyprodinil (E.1.1), fenarimol (E.1.2), pyrimethanil (E.1.3); - Protein synthesis inhibitors: Blasticidin-S (E.2.1), Kasugamycin (E.2.2), Kasugamycin hydrochloride hydrate (E.2.3), Validamycin (E.2.4), Streptomycin (E.2.5), Oxytetracycline (E.2.6); F) Signal transduction inhibitors - MAP / Histidine kinase inhibitors: Fluoroimid (F.1.1), Iprodione (F.1.2), Procymidone (F.1.3), Vinclozolin (F.1.4), Fludioxonil (F.1.5); - G protein inhibitors: Quinoxaline (F.2.1); G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: Kitazin-P (G.1.1), IBP (G.1.2), Pyrazophos (G.1.3), Isoprothiolane (G.1.4); - Lipid peroxidation: Dichlofluanid (G.2.1), PCNB (G.2.2), Tecnazene (G.2.3), Tolclofos-methyl (G.2.4), Biphenyl (G.2.5), Chloroneb (G.2.6), Etridiazole (G.2.7), Thiazole zinc (G.2.8); - Phospholipid biosynthesis and cell wall deposition: Dimethomorph (G.3.1), Flumorph (G.3.2), Mandipropamid (G.3.3), Pyribencarb (G.3.4), Benthiavalicarb (G.3.5), Iprovalicarb (G.3.6), Valifenalate (G.3.7); - Compounds affecting cell membrane permeability and fatty acids: Propamocarb (G.4.1); - Oxysterol binding protein inhibitors: Fluxapyroxad (G.5.1), Fluoxapiprolin (G.5.3), 4-[1-[2-[3-(Difluoromethyl)-5-methylpyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1-tetralinyl)pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-Bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1-tetralinyl)pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(Difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1-tetralinyl)pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-Cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1-tetralinyl)pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-Methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1-tetralinyl) - Pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.11); H) Inhibitors with multi-site action - Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam-sodium (H.2.4), metiram (H.2.5), zineb (H.2.6), thiram (H.2.7), zincb (H.2.8), zinc-mate (H.2.9); - Organochlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, tecnazene (H.3.10), tolylfluanid (H.3.11); - Guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), guazatine-amine (H.4.6), guazatine-amine triacetate (H.4.7), bismerthiazol (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (H.4.10); I) Cell wall synthesis inhibitors - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin (I.1.2); - Melanin synthesis inhibitors: Pyroquilon (I.2.1), Tricyclazole (I.2.2), Carpropamid (I.2.3), Dicyclomet (I.2.4), Blasticidin-S (I.2.5); J) Plant defense inducers - Benzoic acid, 2-chloro-6-[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]-, S-methyl ester (J.1.1), Thiabendazole (J.1.2), Isotianil (J.1.3), Tiadinil (J.1.4), Prohexadione-calcium (J.1.5); Phosphonates: Ethyl phosphonate (J.1.6), Fosetyl-aluminum (J.1.7), Phosphorous acid and its salts (J.1.8), Calcium phosphonate (J.1.11), Potassium phosphonate (J.1.12), Potassium or sodium bicarbonate (J.1.9), 4-Cyclopropyl-N-(2,4-dimethoxyphenyl)-1,2,4-thiadiazole-5-carboxamide (J.1.10); K) Unknown mode of action -Bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), iminoctadine (K.1.6), diclocymet (K.1.7), pyridinitril (K.1.8), barban (K.1.9), barban-methylsulfate (K.1.10), diphenylamine (K.1.11), diflufenican (K.1.12), amisulbrom (K.1.13), flumetover (K.1.14), flumetylsulforim (K.1.60), sulfanilamide (K.1.15), flutianil (K.1.16), harpin protein (K.1.17), sulfotep (K.1.18), 3,5,6-trichloro-2-pyridinol (K.1.19), phthalide (K.1.20), tolprocarb (K.1.21), copper quinolate (K.1.22), propoxyquinoline (K.1.23), seboctylamine (K.1.61), tebufloquin (K.1.24), phthalide-isophthalic acid (K.1.25), pyrazophos (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl-formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl-formamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidine (K.1.35), 2-(4-chlorophenyl)-N-[4-(3,4-dimethoxyphenyl)isoxazole -5-yl]-2-prop-2-ynoxy-acetamide (K.1.36), 3-[5-(4-chlorophenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (picoxystrobin) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), (Z)-ethyl 3-amino-2-cyano-3-phenylprop-2-enoate (K.1.40), tetraconazole (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]pentylcarbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]but-3-ynylcarbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), thiabendazole (K.1.48), bromothalonil (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy -phenyl)-N-ethyl-N-methylformamidine (K.1.53), amisulbrom (K.1.54), fluxapyroxad (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl -N-methylformamidine (K.1.56), N'-[4-(4,5-dichlorothiazol-2-yloxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (K.1.57), flufenoxadiazam (K.1.58), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide (K.1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.60; WO 2018 / 177894, WO 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-trifluoro-N-[[3-fluoro -4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]butyramide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy -N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidine -2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol -3-yl)phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine -2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate (K.1.83), N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]-1H-1,2,4-triazol-3-amine (K.1.85), N-methoxy-N-methyl -1-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.87), N-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.88), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.91), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (K.1.92), N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.95), N'-[2-chloro-4-[(4-methoxyphenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.96), N'-[2-chloro-4-[(4-cyanophenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methylformamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluorophenoxy)-6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (K.1.100), 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro -ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104); L) Biopesticides L1) Microbial biopesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantarum (also known as Bacillus velezensis), Bacillus megaterium, Bacillus mojavensis, Bacillus mycoides, Bacillus pumilus, Bacillus simplex, Bacillus salarius, Bacillus subtilis, Bacillus subtilis var. amyloliquefaciens, Bacillus velezensis, Candida oleophila, Candida saitoana, Clavibacter michiganensis (phage), Coniothyrium minitans, Cryptocline parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, Lysobacter enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Mycosphaerella sphaerosperma, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, Paenibacillus polymyxa, Pantoea agglomerans, Penicillium bilaiae, Phellinus igniarius, Pseudomonas spp., Pseudomonas chlororaphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, Streptomyces lydicus, Streptomyces violaceusniger, Talaromyces flavus, Trichoderma asperelloides, Trichoderma asperellum, Trichoderma atroviride, Trichoderma harzianum, Trichoderma koningii, Trichoderma longibrachiatum, Trichoderma polysporum, Trichoderma stromaticum, Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, Zucchini yellow mosaic virus (avirulent strain); L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activities: hypersensitive proteins, Reynoutria japonica Houtt. extract; L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and / or nematocidal activities: Agrobacterium radiobacter, Bacillus cereus, Bacillus firmus, Bacillus thuringiensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. galleriae, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Beauveria bassiana, Beauveria brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single nucleocapsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, Lecanicillium muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, Metarhizium anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Paenibacillus popilliae, Pasteuria spp., Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, Pseudomonas fluorescens, Spodoptera litura nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, Steinernema feltiae, Steinernema sawfly, Streptomyces gilvosporeus, Streptomyces microflavus; L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, ethyl (E,Z)-2,4-decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyleugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-yl acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone (pentatermanone), (E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, Chenopodium ambrosiodes extract, neem oil, Quillay extract; L5) Microbial pesticides with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activity: Azospirillum amazonense, Azospirillum brasilense, Azospirillum lipoferum, Azospirillum iraquense, Azospirillum halopraeferens, Bradyrhizobium spp., Bradyrhizobium elkanii, Bradyrhizobium japonicum, Bradyrhizobium liaoningense, Bradyrhizobium lupini, Delftia acidovorans, arbuscular mycorrhizal fungi, Mesorhizobium spp., Rhizobium leguminosarum biovar phaseoli, Rhizobium leguminosarum biovar trifolii, Rhizobium leguminosarum biovar viciae, Rhizobium tropici, Sinorhizobium meliloti; O) Insecticides from classes O.1 to O.29 O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, XMC, xylylcarb, triazamate; acephate, fenpyrithrin, dialifos, fenthion, cadusafos, chlorethoxyfos, dichlorvos / DDVP, trichlorfon, dimethoate, fenchlorphos, disulfoton, EPN, ethion, fenamiphos, famphur, fosthiazate, heptenophos, imicyafos, isopropylamine phosphate, O-(methoxyaminothio-phosphoryl) isopropyl salicylate, isoxathion, malathion, methidathion, methamidophos, methidathion, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, methyl parathion, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propargite, propaphos, butylpyrimiphos, temephos, terbufos, tetrachlorvinphos, demeton-S-methyl, triazophos, trichlorfon, pyridalyl; O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, butene-fipronil, pyrafluprole, pyriprole; O.3 Sodium channel modulators: fluvalinate, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, k-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, flumethrin, tau-fluvalinate, brofluthrinate, heptaflumethrin, imiprothrin, chlorfluazuron, metofluthrin, methoxyflurane, epsilon-methoxyflurane, permethrin, phenothrin, propargyl alcohol, profluthrin, pyrethrum, resmethrin, silafluofen, heptafluoropropene, k-heptafluoropropene, tetrafluoroethylene, tetramethrin, tetrabromomethane, tetrafluorobenzene; DDT, methoxychlor; O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, epoxiconazole, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylideneaminoguanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradifurone, triflumezopyrim, bixafen, flufiprole; O.5 Allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram; O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin; O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; phenoxycarb, pyriproxyfen; O.8 Various non-specific (multisite) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic; O.9 Chordotonal organ TRPV channel modulators: cyenopyrafen, pymetrozine, flupyradifurone; O.10 Mite growth inhibitors: clofentezine, hexythiazox, flufenzine; etoxazole; O.11 Microbial disruptors of the insect midgut membrane: Bacillus thuringiensis, Bacillus sphaericus, and the insecticidal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1; O.12 Mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, chlorobenzilate; O.13 Oxidative phosphorylation uncoupling agents interfering via the proton gradient: chlorfenapyr, DNOC, flufenoxuron; O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap, thiocyclam, bisultap; O.15 Chitin biosynthesis inhibitor type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, chlorbenzuron, teflubenzuron; O.16 Chitin biosynthesis inhibitor type 1: buprofezin; O.17 Molting disruptors: cyromazine; O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide; O.19 Octopamine receptor agonists: amitraz; O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, flubenzimine, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone; O.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]hydrazinecarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide; O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, metoxadiazone, spirodiclor, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-ene-10-one, dispirotetramat; O.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanides; O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen, etoxazole, pyraoxystrobin; O.28 Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, flubendiamide, (R)-3-chloro-N 1-{2-Methyl-4-[1,2,2,2–tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-Methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N 1 -{2-Methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-Methyl-2-methylsulfonylethyl)phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl-λ4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloropyridin-2-yl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorantraniliprole; tetraniliprole; thiamethoxam; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorantraniliprole; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide; O.29 Chordotonal organ modulator: flonicamid; O.30 GABA-gated chloride channel allosteric modulator: broflanilide, chlorantraniliprole, isoxazolinon; O.33 Calcium-activated potassium channel modulator: acynonapyr; O.34 Mitochondrial complex III electron transport inhibitor at the Qi site: flometoquin; O.UN Insecticidal compounds with unknown or uncertain mode of action: afoxolaner, azadirachtin, amidoflumet, benzoximate, bromopropylate, chinomethionat, cryolite, cyproflanilid, dichlorothymid, dicofol, tioxazafen, flometoquin, flupyradifurone, fluhexafon, fluxapyroxad, fluralaner, metaldehyde, oxydemethon-methyl, pyridalyl, piperonyl butoxide, pyridalyl, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 4-cyano-N-[2-cyano-5-[[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide, N-[5-[[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, active substance based on Bacillus firmus (Votivo, I-1582); fluopyram; 5-[3-[2,6-Dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; N-[5-[[2-Bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-Cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-Cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-Bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 2-(1,3-Dioxolan-2-yl)-6-[2-(3-pyridyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-Fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; 2-[6-[2-(3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; 1-[(6-Chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; N-(3-Chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; 1-[(6-Chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 2-(3-Pyridyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; chlorantraniliprole; sarolaner, lotilaner; N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2-(2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; benzpyrimoxan; tigolaner; oxasulfuron-din; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]Pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cyclopropanecarboxamide; 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one; Flupyradifurone, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-methylsulfonyl-propionamide, Triflumidopyrimid; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, Cyproflaniliprole, Chlorantraniliprole; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione, 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl]imino-3-(2,2,2-(Trifluoroethyl)thiazolidin-4-one, indoxacarb, N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylsulfonyl-propionamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)isoquinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole, The weight ratio of these components is from 1:100 to 100:
1.
2. A fungicidal mixture, which contains the following as active components: 1) At least one active compound I as defined in claim 1, or its N-oxide, or an agriculturally useful salt thereof; And the following as components: 2) At least one active compound II, which is selected from the groups A) to O) as defined for component 2) in claim 1, or its N-oxide, or an agriculturally useful salt thereof; And the following as components: 3) At least one active compound III, which is selected from the groups A) to O) as defined for component 2) in claim 1, or its N-oxide, or an agriculturally useful salt thereof; Wherein the at least one active compound III of component 3) is different from the at least one active compound II of component 2).
3. The mixture according to claim 2, which contains a synergistically effective amount of compound I and compound II and an additional active compound III.
4. The mixture according to any one of claims 2 or 3, which contains compound I and compound II in a weight ratio of from 100:1 to 1:100, and compound I and compound III in a weight ratio of from 100:1 to 1:
100.
5. The mixture according to any one of claims 1 to 4, wherein, R 1 is H; R 2 is a C1-C6-alkyl group; R 3 independently selected in each case from C1-C6-alkyl, C1-C6-haloalkyl; R 4 is H; R 5 independently selected in each case from C1-C6-alkyl; R 6 independently selected in each case from C1-C6-alkyl; X is independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl in each case; n is 0, 1, 2.
6. The mixture according to any one of claims 1 to 5, wherein, R 1 is H; R 2 is CH3; R 3 independently selected from CH3, CHF2 in each case; R 4 is H; R 5 independently selected from CH3 in each case; R 6 independently selected from CH3 in each case; X is independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkynyl in each case; n 1、2。 7. An agrochemical composition, which comprises a solvent or a solid carrier and the composition according to any one of claims 1 to 6.
8. Use of the mixture according to any one of claims 1 to 7 or the agrochemical composition according to claim 7 for controlling phytopathogenic harmful fungi.
9. The use according to claim 8, for combating Botrytis cinerea and Sclerotinia sclerotiorum.
10. The use according to claim 8, for combating rice leaf, neck, collar and panicle blast.
11. The use according to claim 8, for combating pome and stone fruit diseases.
12. The use according to claim 8, for combating Rhizoctonia diseases (Rhizoctonia solani) in several crops such as turfgrass, cereals, and potatoes and leafy vegetables.
13. The use according to claim 8, for combating storage complex infection diseases in pome and stone fruits.
14. The use according to claim 8, for combating different soil- and seed-borne pathogens.
15. A method for controlling phytopathogenic harmful fungi, the method comprising treating the fungi, their habitats or seeds, soil or plants to be protected from fungal attack with an effective amount of compound I, compound II and compound III as defined in any one of claims 1 to 6 or a composition as defined in claim 7.
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