WO2021209360A1 - Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles - Google Patents

Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles Download PDF

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Publication number
WO2021209360A1
WO2021209360A1 PCT/EP2021/059383 EP2021059383W WO2021209360A1 WO 2021209360 A1 WO2021209360 A1 WO 2021209360A1 EP 2021059383 W EP2021059383 W EP 2021059383W WO 2021209360 A1 WO2021209360 A1 WO 2021209360A1
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Prior art keywords
compound
methyl
methoxy
propanoate
carbonyl
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PCT/EP2021/059383
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French (fr)
Inventor
Lutz Brahm
Ronan Le Vezouet
Lydia LUDWIG
Christian Harald Winter
Markus Gewehr
Wassilios Grammenos
Original Assignee
Basf Se
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Priority to BR112022020612A priority Critical patent/BR112022020612A2/en
Publication of WO2021209360A1 publication Critical patent/WO2021209360A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
  • the present invention relates to a fungicidal mixture comprising as active component 1) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of
  • I-2 N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; and as active component 2) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of
  • 11-31 [(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate
  • 11-32 [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
  • II-33 [(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
  • the invention also relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of mixtures comprising compounds I and compounds II; to the non-therapeutic use of mixtures comprising compounds I and compounds II for controlling phytopathogenic harmful fungi; to agrochemical compositions comprising these mixtures; and to agrochemical compositions comprising these mixtures and further comprising seed.
  • the compounds 1-1 and I-2 defined above for component 1) is herein collectively referred to as “compounds of the formula I” or “compounds I”.
  • the compounds 11-1 to II-36 as defined above for component 2) is herein collectively referred to as “compounds of the formula II” or “compounds II”.
  • the compounds 111-1 to 111-12 as defined herein below for component 3) is herein collectively referred to as “compounds of the formula IN” or “compounds III”.
  • the oxadiazole fungicide 1-1 and I-2 and their pesticidal action and methods for preparing them are known e.g. from WO 2015/185485, WO 2017/211649 and WO 2013/008162.
  • mixtures of different active compounds are conventionally employed for controlling harmful fungi.
  • active compounds having different mechanisms of action it is possible to ensure successful control over a relatively long period of time.
  • compositions comprising at least one compound I and at least one compound II.
  • the term “mixture” in the context of the present invention shall mean a physical mixture of the components prior to application or the result of a simultaneous, i.e. joint or separate, application of a compound I and of a compound II on the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack.
  • Compounds I and/or the compounds II can be present in different crystal modifications, which may differ in biological activity.
  • Agriculturally acceptable salts of the active compounds I, II and III encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the active compounds.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry 1 to 4 Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogen- phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid vv
  • the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-1, II-3, II-5, II-9, 11-11, 11-13, 11-14, 11-19, II-23, II-27, II-29, II-35 and II-36.
  • the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-1, II-3, II-5, 11-9,11-14, 11-11 and II-36.
  • the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-13, 11-14, 11-19, II-23, II-27, II-29, II-35 and II-36.
  • the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-14 and II-36, or mixtures thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-14 and II-36, or mixtures thereof.
  • the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight, based on the total amount of component 2), of compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight, based on the total amount of component 2), of compound II- 14, or an N-oxide, or an agriculturally useful salt thereof.
  • active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight, based on the total amount of component 2), of compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight, based on the total amount of component 2), of compound II- 14, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 2) is compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight based on the total amount of component 2) of compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight based on the total amount of component 2) of compound II- 36, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight based on the total amount of component 2) of compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
  • the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight based on the total amount of component 2) of compound II- 36, or an N-oxide, or an agriculturally useful salt thereof.
  • the presentinvention relates to mixtures, wherein active component 2) is compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
  • the presentinvention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
  • the ratio by weight of compound I and compound II in binary mixtures is from 500:1 to 1:500, preferably from 100:1 to 1:100 more preferably from 50:1 to 1:50, most preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, or 1 :1.
  • the ratio by weight of compound I and compound II in binary mixtures is from 500:1 to 1:1, preferably from 300:1 to 1:1 more preferably from 50:1 to 1 :1 , most preferably from 20:1 to 1 :1, including also ratios from 10:1 to 1:1 , 5:1 to 1:1, or 1:1.
  • the scope of the present invention includes mixtures of the (R)- and (S)-isomers and the racemates of compounds I and/or III having one or more chiral centers.
  • atrope isomers of active compounds I and/or III may be present. They also form part of the subject matter of the invention.
  • the present invention relates to fungicidal oxadiazole mixtures M.1 to M.360 that are each identified in one row of table M below, wherein component 1) and component 2) are identified together with their relative amounts (weight ratio).
  • the amount of compound 1-1 in mixtures M.1 to M.180 is in the range between 60 and 150 g/ha, preferably between 80 and 120 g/ha, more preferably 100 g/ha.
  • the amount of compound I-2 in mixtures M.181 to M.360 is in the range between 50 and 150 g/ha, preferably between 70 and 100, more preferably 85 g/ha.
  • the binary mixtures above comprise, besides at least one compound I as component 1) and at least one compound II as component 2), additionally at least one further active compound III as component 3), resulting in a ternary mixture.
  • the components 1) and 2), or, all three components 1), 2) and 3), in these mixtures are present in a synergistically effective amount.
  • one embodiment relates to ternary mixtures comprising, as active components
  • active component 1) at least one active compound selected from the group consisting of 1-1 and I-2 as defined herein above, or an N- oxide, or an agriculturally useful salt thereof; and as active component
  • I-1 copper(ll) oxychloride, III-2 copper(ll) hydroxide, III-3 copper sulfate, III-4: mancozeb, NI-5: prothioconazole, IN-6: fluxapyroxad,
  • III-7 metyltetraprole, NI-8: fenpropimorph, NI-9: mefentrifluconazole, 111-10: tebuconazol, 111-11: pydiflumetofen, 111-12: inpyrfluxam, IN-13: picoxystrobin, 111-14: benzovindiflupyr, 111-15: cyproconazol, 111-16: fluindapyr, 111-17: trifloxystrobin, IN-18 metominostrobin, 111-19: mandestrobin, IN-20: chlorothalonil, 111-21 metconazol, IN-22: fludioxonil; or an N- oxide, or an agriculturally useful salt thereof.
  • the weight ratio of compound I and compound III in ternary mixtures is from 500:1 to 1 :500, preferably from 100:1 to 1:100 more preferably from 50:1 to 1:50, most preferably from 20:1 to 1:20, including also ratios from 10:1 to 1 :10, 5:1 to 1 :5, or 1 :1.
  • the active substances referred to as compounds III, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
  • Table T1 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 100:1 to 1:100.
  • Table T2 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 20:1 to 1:20.
  • Table T3 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 5:1 to 1 :5.
  • Table T4 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 2:1 to 1 :2.
  • Table T5 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 1:1.
  • Table T6 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 100:1 to 1:100.
  • Table T7 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 20:1 to 1:20.
  • Table T8 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 5:1 to 1 :5.
  • Table T9 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 2:1 to 1 :2.
  • Table T10 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 1:1.
  • Table T11 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 100:1 to 1:100.
  • Table T12 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 20:1 to 1:20.
  • Table T13 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 5:1 to 1 :5.
  • Table T14 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 2:1 to 1 :2.
  • Table T15 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 1:1.
  • Table T16 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 100:1 to 1:100.
  • Table T17 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 20:1 to 1:20.
  • Table T18 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 5:1 to 1 :5.
  • Table T19 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 2:1 to 1 :2.
  • Table T20 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 1:1.
  • Table T21 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 100:1 to 1:100.
  • Table T22 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 20:1 to 1:20.
  • Table T23 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 5:1 to 1 :5.
  • Table T24 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 2:1 to 1 :2.
  • Table T25 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 1:1.
  • Table T26 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-6 as component 3), and whereas the weight ratio of compound I to compound NI-6 is 100:1 to 1:100.
  • Table T27 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 20:1 to 1:20.
  • Table T28 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 5:1 to 1 :5.
  • Table T29 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 2:1 to 1 :2.
  • Table T30 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 1:1.
  • Table T31 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 100:1 to 1:100.
  • Table T32 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 20:1 to 1:20.
  • Table T33 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 5:1 to 1 :5.
  • Table T34 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 2:1 to 1 :2.
  • Table T35 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 1:1.
  • Table T36 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 100:1 to 1:100.
  • Table T37 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 20:1 to 1:20.
  • Table T38 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 5:1 to 1 :5.
  • Table T39 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 2:1 to 1 :2.
  • Table T40 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 1:1.
  • Table T41 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 100:1 to 1:100.
  • Table T42 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 20:1 to 1:20.
  • Table T43 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 5:1 to 1 :5.
  • Table T44 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 2:1 to 1 :2.
  • Table T45 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-9 as component 3), and whereas the weight ratio of compound I to compound ill-9 is 1:1.
  • Table T46 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 100:1 to 1:100.
  • Table T47 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 20:1 to 1:20.
  • Table T48 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 5:1 to 1:5.
  • Table T49 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 2:1 to 1:2.
  • Table T50 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 1 :1.
  • Table T51 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 100:1 to 1:100.
  • Table T52 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 20:1 to 1:20.
  • Table T53 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 5:1 to 1:5.
  • Table T54 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 2:1 to 1:2.
  • Table T55 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 1 :1.
  • Table T56 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 100:1 to 1 :100.
  • Table T57 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 20:1 to 1:20.
  • Table T58 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 5:1 to 1:5.
  • Table T59 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 2:1 to 1:2.
  • Table T60 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 1 :1.
  • Table T61 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 100:1 to 1 :100.
  • Table T62 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 20:1 to 1:20.
  • Table T63 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 5:1 to 1:5.
  • Table T64 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 2:1 to 1:2.
  • Table T65 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 1 :1.
  • Table T66 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 100:1 to 1 :100.
  • Table T67 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 20:1 to 1:20.
  • Table T68 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 5:1 to 1:5.
  • Table T69 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 2:1 to 1:2.
  • Table T70 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 1 :1.
  • Table T71 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 100:1 to 1:100.
  • Table T72 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 20:1 to 1:20.
  • Table T73 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 5:1 to 1:5.
  • Table T74 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 2:1 to 1:2.
  • Table T75 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 1 :1.
  • Table T76 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 100:1 to 1:100.
  • Table T77 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 20:1 to 1:20.
  • Table T78 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 5:1 to 1:5.
  • Table T79 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 2:1 to 1:2.
  • Table T80 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 1 :1.
  • Table T81 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 100:1 to 1:100.
  • Table T82 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 20:1 to 1:20.
  • Table T83 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 5:1 to 1:5.
  • Table T84 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 2:1 to 1:2.
  • Table T85 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 1 :1.
  • Table T86 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 100:1 to 1:100.
  • Table T87 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 20:1 to 1:20.
  • Table T88 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 5:1 to 1:5.
  • Table T89 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 2:1 to 1:2.
  • Table T90 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 1 :1.
  • Table T91 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 100:1 to 1:100.
  • Table T92 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 20:1 to 1:20.
  • Table T93 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 5:1 to 1:5.
  • Table T94 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 2:1 to 1:2.
  • Table T95 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 1 :1.
  • Table T96 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-20 as component 3), and whereas the weight ratio of compound I to compound MI-20 is 100:1 to 1:100.
  • Table T97 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 20:1 to 1:20.
  • Table T98 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 5:1 to 1:5.
  • Table T99 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 2:1 to 1:2.
  • Table T100 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-20 as component 3), and whereas the weight ratio of compound I to compound 111-20 is 1 :1.
  • Table T101 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 100:1 to 1 :100.
  • Table T102 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 20:1 to 1:20.
  • Table T103 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 5:1 to 1:5.
  • Table T104 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 2:1 to 1:2.
  • Table T105 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 1 :1.
  • Table T106 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-22 as component 3), and whereas the weight ratio of compound I to compound MI-22 is 100:1 to 1 :100.
  • Table T107 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-22 as component 3), and whereas the weight ratio of compound I to compound 111-22 is 20: 1 to 1 :20.
  • Table T108 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 5:1 to 1:5.
  • Table T109 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 2:1 to 1:2.
  • Table T110 Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 1 :1.
  • the amount of compound 1-1 in mixtures of Tables T1 to T110 is in the range between 60 and 150 g/ha, preferably between 80 and 120 g/ha, more preferably 100 g/ha.
  • the amount of compound I-2 in mixtures of Tables T 1 to T110 is in the range between 70 and 100 g/ha, preferably 85 g/ha.
  • the binary and ternary mixtures and agrochemical compositions thereof according to the invention can, in the use form as fungicides, also be present together with further active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
  • further active substances e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
  • the binary and ternary mixtures and agrochemical compositions thereof according to the invention are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota (Basidiomycetes), for example, but not limited to the genus Phakopsora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and
  • Fungi imperfecti for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium,
  • Plasmodiophoromycetes for example but not limited to the genus Plasmodiophora
  • Zygomycetes for example, but not limited to the genus Rhizopus.
  • Some of the binary and ternary mixtures and agrochemical compositions thereof according to the invention are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the binary and ternary mixtures and agrochemical compositions thereof according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • binary and ternary mixtures and agrochemical compositions thereof according to the invention are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, oilseed rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, oilseed rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • the binary and ternary mixtures and agrochemical compositions thereof according to the invention are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae on soybeans and/or against Puccinia triticina, P. striiformis, P. hordei, P. graminis or P. recondita on wheat, barley or rye; P. coronata e.g. on oats, P. sorghi und P. polysora on corn; Puccinia spp. on other crops, e g. P.
  • the binary mixtures M.1 to M.360 of Table M and the ternary mixtures disclosed in Tables T1 to T80 above are used against Phakopsora pachyrhizi and P. meibomiae on soybeans.
  • the binary and ternary mixtures according to the invention can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • 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, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g.
  • compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
  • 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.
  • the binary or ternary mixtures of active compounds described herein can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given herein for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • compositions in question give, after two-to-tenfold dilution, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • binary or ternary mixture according to the invention or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active compound of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active compound applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • E (1 - a/b) 100 a corresponds to the fungicidal infection of the treated plants in % and b corresponds to the fungicidal infection of the untreated (control) plants in %
  • An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
  • Colby's formula (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies. Colby's formula:
  • E expected efficacy expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b.
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of Pyricularia oryzae in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies, which are summarized in table A.1.
  • An efficacy of 0 means that the growth level of the pathogens corresponds to that of the untreated control; an efficacy of 100 means that the pathogens were not growing.
  • the expected efficacies of active compound mixtures were determined using Colby's formula and compared with the observed efficacies. Table A.1
  • the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
  • the stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations.
  • MTP micro titer plate
  • a spore suspension of Septoria tritici in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added.
  • the plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
  • the measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies as described in section A. I) and summarized in table A.2.
  • the compound was dissolved in a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solvent-emulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml. This stock solution was then diluted with the described solvent- emulsifier-water mixture to the final concentration given in the table below.
  • Wettol which is based on ethoxylated alkylphenoles
  • the trial plants were cultivated for fourteen days in a greenhouse chamber at 23°C to 27°C and a relative humidity between 60% and 80%.
  • the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
  • the disease ratings (or diseased leaf area) were converted into efficacies as described in section B. I) and summarized in table B.2.
  • Table B.2 Table B.2

Abstract

Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles The present invention relates to fungicidal mixtures comprising at least one substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles (compounds I) and at least one active compound II; to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of mixtures comprising compounds I and compounds II; to the non-therapeutic use of mixtures comprising compounds I and compounds II for controlling phytopathogenic harmful fungi; to agrochemical compositions comprising these mixtures; and to agrochemical compositions further comprising seed.

Description

Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles Description The present invention relates to a fungicidal mixture comprising as active component 1) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of
1-1 : N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide,
Figure imgf000002_0001
I-2: N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide;
Figure imgf000002_0002
and as active component 2) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of
11-1: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000002_0003
II-2: [(1S,2S)-2-(2,4-dimethylphenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine- 2-carbonyl)amino]propanoate
Figure imgf000002_0004
II-3: [(1S,2S)-2-(2,4-difluorophenyl)-1 ,3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate II-4: [(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000003_0001
II-5: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000003_0002
11-6: [(1S,2S)-2-(2,4-dimethylphenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine- 2-carbonyl)amino]propanoate
Figure imgf000003_0003
II-7: [(1S,2S)-2-(2,4-difluorophenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000003_0004
II-8: [(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate 11-9: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate
Figure imgf000004_0001
11-10: [2-[[(1S)-2-[(1S,2S)-2-(2,4-dimethylphenyl)-1 ,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate
Figure imgf000004_0002
11-11: [2-[[(1S)-2-[(1S,2S)-2-(2,4-difluorophenyl)-1 ,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate
Figure imgf000004_0003
11-12: [2-[[(1S)-2-[(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate
Figure imgf000004_0004
11-13: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate 11-14: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000005_0001
11-15: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000005_0002
11-16: [4-methoxy-2-[[(1S)-1-methyl-2-[(1S,2S)-1-methyl-2-(o-tolyl)propoxy]-2-oxo- ethyl]carbamoyl]-3-pyridyl] 2-methylpropanoate
Figure imgf000005_0003
11-17: [(1S,2S)-2-(2,4-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000005_0004
11-18: [2-[[(1S)-2-[(1S,2S)-2-(2,4-dimethylphenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate
Figure imgf000005_0005
11-19: [(1S,2S)-2-(2,6-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate II-20: [2-[[(1S)-2-[(1S,2S)-2-(2,6-dimethylphenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate
Figure imgf000006_0001
11-21 : [(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate
Figure imgf000006_0002
II-22: [2-[[(1S)-2-[(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propoxy]-1-methyl-2- oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate
Figure imgf000006_0003
II-23: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000006_0004
II-24: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate
Figure imgf000006_0005
11-25: [(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000007_0001
II-26: [4-methoxy-2-[[(1S)-1-methyl-2-[(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propoxy]-2- oxo-ethyl]carbamoyl]-3-pyridyl] 2-methylpropanoate
Figure imgf000007_0002
II-27: [(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000007_0003
II-28: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate
Figure imgf000007_0004
II-29: [(1S,2S)-2-(2,4-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000007_0005
II-30: [(1S,2S)-2-(2,6-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000007_0006
11-31 : [(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate 11-32: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000008_0001
II-33: [(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000008_0002
II-34: [(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000008_0003
II-35: [(1S,2R)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate
Figure imgf000008_0004
II-36: [(1R,2R)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate
Figure imgf000008_0005
The invention also relates to a method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of mixtures comprising compounds I and compounds II; to the non-therapeutic use of mixtures comprising compounds I and compounds II for controlling phytopathogenic harmful fungi; to agrochemical compositions comprising these mixtures; and to agrochemical compositions comprising these mixtures and further comprising seed.
The compounds 1-1 and I-2 defined above for component 1) is herein collectively referred to as “compounds of the formula I” or “compounds I”. The compounds 11-1 to II-36 as defined above for component 2) is herein collectively referred to as “compounds of the formula II” or “compounds II”. The compounds 111-1 to 111-12 as defined herein below for component 3) is herein collectively referred to as “compounds of the formula IN” or “compounds III”.
The oxadiazole fungicide 1-1 and I-2 and their pesticidal action and methods for preparing them are known e.g. from WO 2015/185485, WO 2017/211649 and WO 2013/008162.
Compounds II, their compositions and methods for preparing them are known from WO 2018/129238 and WO 2019/173665.
Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound in the control of harmful fungi leads in many cases to a rapid selection of those fungus strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi with the active compound in question is then no longer possible.
To reduce the risk of the selection of resistant fungus strains, mixtures of different active compounds are conventionally employed for controlling harmful fungi. By combining active compounds having different mechanisms of action, it is possible to ensure successful control over a relatively long period of time.
It is an object of the present invention to provide, with a view to effective resistance management and effective control of phytopathogenic harmful fungi, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi (synergistic mixtures) and a broadened activty spectrum, in particular for certain indications.
We have accordingly found that this object is achieved by the compositions, defined herein, comprising at least one compound I and at least one compound II.
Moreover, we have found that simultaneous, that is joint or separate, application of a compound I and a compound II or successive application of a compound I and of compound II allows better control of harmful fungi than is possible with the individual compounds alone (synergistic mixtures). Therefore, the term “mixture” in the context of the present invention shall mean a physical mixture of the components prior to application or the result of a simultaneous, i.e. joint or separate, application of a compound I and of a compound II on the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack.
Compounds I and/or the compounds II can be present in different crystal modifications, which may differ in biological activity.
Agriculturally acceptable salts of the active compounds I, II and III encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the active compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry 1 to 4 Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogen- phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid vv
In one embodiment the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-1, II-3, II-5, II-9, 11-11, 11-13, 11-14, 11-19, II-23, II-27, II-29, II-35 and II-36.
In another embodiment the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-1, II-3, II-5, 11-9,11-14, 11-11 and II-36.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-13, 11-14, 11-19, II-23, II-27, II-29, II-35 and II-36.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-14 and II-36, or mixtures thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is at least one compound, or an N-oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-14 and II-36, or mixtures thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight, based on the total amount of component 2), of compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight, based on the total amount of component 2), of compound II- 14, or an N-oxide, or an agriculturally useful salt thereof. In a further embodiment the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight, based on the total amount of component 2), of compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight, based on the total amount of component 2), of compound II- 14, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is compound 11-14, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight based on the total amount of component 2) of compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 70% by weight based on the total amount of component 2) of compound II- 36, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight based on the total amount of component 2) of compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the present invention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is a mixture of compounds 11-14 and II-36, wherein the mixture comprises at least 90% by weight based on the total amount of component 2) of compound II- 36, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the presentinvention relates to mixtures, wherein active component 2) is compound II-36, or an N-oxide, or an agriculturally useful salt thereof.
In a further embodiment the presentinvention relates to mixtures, wherein active component 1) is 1-1 , and active component 2) is compound II-36, or an N-oxide, or an agriculturally useful salt thereof. The ratio by weight of compound I and compound II in binary mixtures is from 500:1 to 1:500, preferably from 100:1 to 1:100 more preferably from 50:1 to 1:50, most preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, or 1 :1. In another aspect the ratio by weight of compound I and compound II in binary mixtures is from 500:1 to 1:1, preferably from 300:1 to 1:1 more preferably from 50:1 to 1 :1 , most preferably from 20:1 to 1 :1, including also ratios from 10:1 to 1:1 , 5:1 to 1:1, or 1:1.
The scope of the present invention includes mixtures of the (R)- and (S)-isomers and the racemates of compounds I and/or III having one or more chiral centers. As a result of hindered rotation of asymmetrically substituted groups, atrope isomers of active compounds I and/or III may be present. They also form part of the subject matter of the invention.
In a preferred aspect the present invention relates to fungicidal oxadiazole mixtures M.1 to M.360 that are each identified in one row of table M below, wherein component 1) and component 2) are identified together with their relative amounts (weight ratio).
Table M
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000013_0001
Figure imgf000013_0002
Figure imgf000014_0001
Figure imgf000014_0002
Figure imgf000015_0001
Figure imgf000015_0002
Figure imgf000016_0001
Figure imgf000016_0002
In one aspect of the present invention the amount of compound 1-1 in mixtures M.1 to M.180 is in the range between 60 and 150 g/ha, preferably between 80 and 120 g/ha, more preferably 100 g/ha.
In one aspect of thepresent invention the amount of compound I-2 in mixtures M.181 to M.360 is in the range between 50 and 150 g/ha, preferably between 70 and 100, more preferably 85 g/ha.
It may be preferred that the binary mixtures above comprise, besides at least one compound I as component 1) and at least one compound II as component 2), additionally at least one further active compound III as component 3), resulting in a ternary mixture. Preferably, the components 1) and 2), or, all three components 1), 2) and 3), in these mixtures are present in a synergistically effective amount.
Accordingly one embodiment relates to ternary mixtures comprising, as active components
1) at least one active compound selected from the group consisting of 1-1 and I-2 as defined herein above, or an N- oxide, or an agriculturally useful salt thereof; and as active component
2) at least one active compound selected from the group consisting of compounds 11-1 to
II-36 as defined herein above, or an N- oxide, or an agriculturally useful salt thereof; and as active component
3) at least one active compound selected from the group consisting of compounds 111-1 to MI-22:
II I-1 : copper(ll) oxychloride, III-2 copper(ll) hydroxide, III-3 copper sulfate, III-4: mancozeb, NI-5: prothioconazole, IN-6: fluxapyroxad,
III-7: metyltetraprole, NI-8: fenpropimorph, NI-9: mefentrifluconazole, 111-10: tebuconazol, 111-11: pydiflumetofen, 111-12: inpyrfluxam, IN-13: picoxystrobin, 111-14: benzovindiflupyr, 111-15: cyproconazol, 111-16: fluindapyr, 111-17: trifloxystrobin, IN-18 metominostrobin, 111-19: mandestrobin, IN-20: chlorothalonil, 111-21 metconazol, IN-22: fludioxonil; or an N- oxide, or an agriculturally useful salt thereof.
The weight ratio of compound I and compound III in ternary mixtures is from 500:1 to 1 :500, preferably from 100:1 to 1:100 more preferably from 50:1 to 1:50, most preferably from 20:1 to 1:20, including also ratios from 10:1 to 1 :10, 5:1 to 1 :5, or 1 :1.
The active substances referred to as compounds III, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
EP-A 141 317; EP-A 152 031; EP-A 226917; EP-A 243 970; EP-A 256503; EP-A 428941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122244,
JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;
US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; 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, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177,
WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 11/081174, WO 13/47441).
Particularly preferred are the ternary mixtures listed in Tables T1 to T110:
Table T1: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 100:1 to 1:100.
Table T2: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 20:1 to 1:20.
Table T3: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 5:1 to 1 :5.
Table T4: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 2:1 to 1 :2.
Table T5: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound II 1-1 as component 3), and whereas the weight ratio of compound I to compound 111-1 is 1:1.
Table T6: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 100:1 to 1:100.
Table T7: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 20:1 to 1:20.
Table T8: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 5:1 to 1 :5.
Table T9: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 2:1 to 1 :2.
Table T10: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-2 as component 3), and whereas the weight ratio of compound I to compound III-2 is 1:1.
Table T11: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 100:1 to 1:100.
Table T12: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 20:1 to 1:20.
Table T13: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 5:1 to 1 :5.
Table T14: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 2:1 to 1 :2.
Table T15: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-3 as component 3), and whereas the weight ratio of compound I to compound III-3 is 1:1.
Table T16: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 100:1 to 1:100.
Table T17: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 20:1 to 1:20.
Table T18: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 5:1 to 1 :5.
Table T19: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 2:1 to 1 :2.
Table T20: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-4 as component 3), and whereas the weight ratio of compound I to compound III-4 is 1:1.
Table T21: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 100:1 to 1:100.
Table T22: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 20:1 to 1:20.
Table T23: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 5:1 to 1 :5.
Table T24: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 2:1 to 1 :2.
Table T25: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-5 as component 3), and whereas the weight ratio of compound I to compound NI-5 is 1:1.
Table T26: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-6 as component 3), and whereas the weight ratio of compound I to compound NI-6 is 100:1 to 1:100. Table T27: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 20:1 to 1:20.
Table T28: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 5:1 to 1 :5.
Table T29: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 2:1 to 1 :2.
Table T30: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-6 as component 3), and whereas the weight ratio of compound I to compound III-6 is 1:1.
Table T31: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 100:1 to 1:100.
Table T32: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 20:1 to 1:20.
Table T33: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 5:1 to 1 :5.
Table T34: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 2:1 to 1 :2.
Table T35: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-7 as component 3), and whereas the weight ratio of compound I to compound NI-7 is 1:1.
Table T36: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 100:1 to 1:100.
Table T37: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 20:1 to 1:20.
Table T38: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 5:1 to 1 :5.
Table T39: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 2:1 to 1 :2.
Table T40: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-8 as component 3), and whereas the weight ratio of compound I to compound NI-8 is 1:1.
Table T41: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 100:1 to 1:100.
Table T42: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 20:1 to 1:20.
Table T43: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 5:1 to 1 :5.
Table T44: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-9 as component 3), and whereas the weight ratio of compound I to compound III-9 is 2:1 to 1 :2.
Table T45: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-9 as component 3), and whereas the weight ratio of compound I to compound ill-9 is 1:1.
Table T46: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 100:1 to 1:100.
Table T47: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 20:1 to 1:20.
Table T48: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 5:1 to 1:5.
Table T49: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 2:1 to 1:2.
Table T50: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-10 as component 3), and whereas the weight ratio of compound I to compound 111-10 is 1 :1.
Table T51: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 100:1 to 1:100.
Table T52: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 20:1 to 1:20.
Table T53: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 5:1 to 1:5.
Table T54: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound ill-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 2:1 to 1:2.
Table T55: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-11 as component 3), and whereas the weight ratio of compound I to compound 111-11 is 1 :1.
Table T56: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 100:1 to 1 :100.
Table T57: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 20:1 to 1:20.
Table T58: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 5:1 to 1:5.
Table T59: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 2:1 to 1:2.
Table T60: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-12 is 1 :1.
Table T61: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 100:1 to 1 :100.
Table T62: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 20:1 to 1:20.
Table T63: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 5:1 to 1:5.
Table T64: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 2:1 to 1:2.
Table T65: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-13 as component 3), and whereas the weight ratio of compound I to compound 111-13 is 1 :1.
Table T66: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 100:1 to 1 :100.
Table T67: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 20:1 to 1:20.
Table T68: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-14 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 5:1 to 1:5.
Table T69: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 2:1 to 1:2.
Table T70: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-12 as component 3), and whereas the weight ratio of compound I to compound 111-14 is 1 :1. Table T71: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 100:1 to 1:100.
Table T72: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 20:1 to 1:20.
Table T73: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 5:1 to 1:5.
Table T74: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 2:1 to 1:2.
Table T75: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-15 as component 3), and whereas the weight ratio of compound I to compound 111-15 is 1 :1.
Table T76: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 100:1 to 1:100.
Table T77: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 20:1 to 1:20.
Table T78: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 5:1 to 1:5.
Table T79: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 2:1 to 1:2.
Table T80: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-16 as component 3), and whereas the weight ratio of compound I to compound 111-16 is 1 :1.
Table T81: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 100:1 to 1:100.
Table T82: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 20:1 to 1:20.
Table T83: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 5:1 to 1:5.
Table T84: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 2:1 to 1:2.
Table T85: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-17 as component 3), and whereas the weight ratio of compound I to compound 111-17 is 1 :1.
Table T86: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 100:1 to 1:100.
Table T87: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 20:1 to 1:20.
Table T88: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 5:1 to 1:5.
Table T89: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 2:1 to 1:2.
Table T90: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-18 as component 3), and whereas the weight ratio of compound I to compound 111-18 is 1 :1.
Table T91: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 100:1 to 1:100.
Table T92: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 20:1 to 1:20.
Table T93: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 5:1 to 1:5.
Table T94: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 2:1 to 1:2.
Table T95: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-19 as component 3), and whereas the weight ratio of compound I to compound 111-19 is 1 :1.
Table T96: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-20 as component 3), and whereas the weight ratio of compound I to compound MI-20 is 100:1 to 1:100.
Table T97: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 20:1 to 1:20.
Table T98: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 5:1 to 1:5.
Table T99: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-20 as component 3), and whereas the weight ratio of compound I to compound IN-20 is 2:1 to 1:2.
Table T100: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-20 as component 3), and whereas the weight ratio of compound I to compound 111-20 is 1 :1.
Table T101: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 100:1 to 1 :100.
Table T102: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 20:1 to 1:20.
Table T103: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 5:1 to 1:5.
Table T104: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 2:1 to 1:2.
Table T105: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound 111-21 as component 3), and whereas the weight ratio of compound I to compound 111-21 is 1 :1.
Table T106: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound III-22 as component 3), and whereas the weight ratio of compound I to compound MI-22 is 100:1 to 1 :100.
Table T107: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-22 as component 3), and whereas the weight ratio of compound I to compound 111-22 is 20: 1 to 1 :20.
Table T108: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound MI-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 5:1 to 1:5.
Table T109: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 2:1 to 1:2.
Table T110: Mixtures M.1 to M.360 as defined in Table M, wherein each mixture additionally comprises compound IN-22 as component 3), and whereas the weight ratio of compound I to compound IN-22 is 1 :1.
In one aspect of the present invention the amount of compound 1-1 in mixtures of Tables T1 to T110 is in the range between 60 and 150 g/ha, preferably between 80 and 120 g/ha, more preferably 100 g/ha.
In another aspect of the present invention the amount of compound I-2 in mixtures of Tables T 1 to T110 is in the range between 70 and 100 g/ha, preferably 85 g/ha.
The binary and ternary mixtures and agrochemical compositions thereof according to the invention can, in the use form as fungicides, also be present together with further active substances, e. g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers, as pre-mix or, if appropriate, not until immeadiately prior to use (tank mix).
Mixing the active compounds I, II and III and the compositions comprising the mixtures, respectively, in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The binary and ternary mixtures and agrochemical compositions thereof according to the invention are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota (Basidiomycetes), for example, but not limited to the genus Phakopsora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungi imperfecti), for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium,
Phytophthora; Plasmodiophoromycetes, for example but not limited to the genus Plasmodiophora; Zygomycetes, for example, but not limited to the genus Rhizopus.
Some of the binary and ternary mixtures and agrochemical compositions thereof according to the invention are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The binary and ternary mixtures and agrochemical compositions thereof according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as oilseed rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, oilseed rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, binary and ternary mixtures and agrochemical compositions thereof according to the invention are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, oilseed rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes. The binary and ternary mixtures and agrochemical compositions thereof according to the invention, in particular the binary mixtures M.1 to M.360 of Table M and the ternary mixtures disclosed in Tables T1 to T80 above, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae on soybeans and/or against Puccinia triticina, P. striiformis, P. hordei, P. graminis or P. recondita on wheat, barley or rye; P. coronata e.g. on oats, P. sorghi und P. polysora on corn; Puccinia spp. on other crops, e g. P. heliathi on sunflower, P. arachidis on peanuts; Uromyces spp. on pulses and other crops crops, e.g. Uromyces viciae-fabae, Uromyces vigniae, Uromyces pisi, U. ciceris-arietini, U. betae syn U. beticola.
In a particularly preferred embodiment the binary mixtures M.1 to M.360 of Table M and the ternary mixtures disclosed in Tables T1 to T80 above are used against Phakopsora pachyrhizi and P. meibomiae on soybeans.
The binary and ternary mixtures according to the invention can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for 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, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The 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.
The binary or ternary mixtures of active compounds described herein can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given herein for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), 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 employed. The compositions in question give, after two-to-tenfold dilution, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, binary or ternary mixture according to the invention or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active compound of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
When used in the protection of materials or stored products, the amount of active compound applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material.
By applying binary or ternary mixture according to the invention a synergistic effect can be obtained, i.e. more than simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the binary or ternary mixture according to the invention either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active compound applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When applying binary or ternary mixture according to the invention sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
Biological activity
The fungicidal action of the mixtures according to the invention can be shown by the tests described below. The efficacy (E) is calculated as follows using Abbot's formula:
E = (1 - a/b) 100 a corresponds to the fungicidal infection of the treated plants in % and b corresponds to the fungicidal infection of the untreated (control) plants in %
An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficacies of active compound combinations may be determined using Colby's formula (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 15, pp. 20-22, 1967) and compared with the observed efficacies. Colby's formula:
E = x+y - x y/100
E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b.
A) Microtest
A. I) Activity against rice blast Pyricularia oryzae (PYRIOR)
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies, which are summarized in table A.1. An efficacy of 0 means that the growth level of the pathogens corresponds to that of the untreated control; an efficacy of 100 means that the pathogens were not growing. The expected efficacies of active compound mixtures were determined using Colby's formula and compared with the observed efficacies. Table A.1
Figure imgf000030_0001
A.11) Activity against leaf blotch on wheat caused by Septoria tritici (SEPTTR)
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies as described in section A. I) and summarized in table A.2.
Table A.2
Figure imgf000031_0001
A. Ill) Activity against early blight caused by Alternaria solani (ALTESO)
An analogue procedure as described under A.l) was followed. A spore suspension of Septoria tritici in an aqueous biomalt or yeast-bactopeptone-glycerine or Alternaria solani in an aqueous biomalt or yeast-bactopeptone-glycerine or DOB solution was added to the aqueous compositions comprising the active compounds.
Figure imgf000032_0001
B) Greenhouse Testing
The compound was dissolved in a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a ratio (volume) solvent-emulsifier of 99 to 1 to give a total volume of 5 ml. Subsequently, water was added to total volume of 100 ml. This stock solution was then diluted with the described solvent- emulsifier-water mixture to the final concentration given in the table below.
B.l) Curative control of soybean rust on soybeans caused by Phakopsora pachyrhizi (PHAKPA) Leaves of potted soybean seedlings were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20°C to 24°C for 24 hours. The next day the plants were cultivated for 2 days in a greenhouse chamber at 23°C to 27°C and a relative humidity between 60% and 80%. Then the plants were sprayed to run-off with the previously described spray solution, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. Then the trial plants were cultivated for 14 days in a greenhouse chamber at 23°C to 27°C and a relative humidity between 60% and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area. The disease ratings (or diseased leaf area) were converted into efficacies and summarized in table B.1. An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected. The expected efficacies of active compound mixtures were determined using Colby's formula.
Table B.1
Figure imgf000033_0001
B.ll) Protective control of soybean rust on soybeans caused by Phakopsora pachyrhizi (PHAKPA) Leaves of potted soybean seedlings were sprayed to run-off with the previously described spray solution, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. The trial plants were cultivated for 2 days in a greenhouse chamber at 23°C to 27°C and a relative humidity between 60% and 80%. Then the plants were inoculated with spores of Phakopsora pachyrhizi. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95% and 20°C to 24°C for 24 hours. The trial plants were cultivated for fourteen days in a greenhouse chamber at 23°C to 27°C and a relative humidity between 60% and 80%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area. The disease ratings (or diseased leaf area) were converted into efficacies as described in section B. I) and summarized in table B.2. Table B.2
Figure imgf000034_0001

Claims

Claims:
1. A fungicidal mixture comprising as active component 1) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of
1-1 : N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide,
I-2: N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; and as active component 2) at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of:
II-1: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
11-2: [(1 S,2S)-2-(2,4-dimethylphenyl)-1 ,3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
11-3: [(1 S,2S)-2-(2,4-difluorophenyl)-1 ,3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-4: [(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-5: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)- 1,3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
11-6: [(1 S,2S)-2-(2,4-dimethylphenyl)-1 ,3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-7: [(1S,2S)-2-(2,4-difluorophenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-8: [(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1, 3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-9: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate,
11-10: [2-[[(1S)-2-[(1S,2S)-2-(2,4-dimethylphenyl)-1 ,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate,
11-11: [2-[[(1S)-2-[(1S,2S)-2-(2,4-difluorophenyl)-1 ,3-dimethyl-butoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate,
11-12: [2-[[(1S)-2-[(1S,2S)-2-(2-fluoro-4-methyl-phenyl)-1,3-dimethyl-butoxy]-1 -methyl-2- oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate,
11-13: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate,
11-14: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate,
11-15: [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate,
11-16: [4-methoxy-2-[[(1S)-1-methyl-2-[(1S,2S)-1-methyl-2-(o-tolyl)propoxy]-2-oxo- ethyl]carbamoyl]-3-pyridyl] 2-methylpropanoate,
11-17: [(1S,2S)-2-(2,4-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate, 11-18: [2-[[(1S)-2-[(1S,2S)-2-(2,4-dimethylphenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate,
11-19: [(1S,2S)-2-(2,6-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-20: [2-[[(1S)-2-[(1S,2S)-2-(2,6-dimethylphenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate,
11-21: [(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-22: [2-[[(1S)-2-[(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propoxy]-1- methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate,
II-23: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-24: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1-methyl-propoxy]-1-methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate,
II-25: [(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-26: [4-methoxy-2-[[(1S)-1-methyl-2-[(1S,2S)-1-methyl-2-[2-
(trifluoromethyl)phenyl]propoxy]-2-oxo-ethyl]carbamoyl]-3-pyridyl] 2- methylpropanoate,
II-27: [(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-28: [2-[[(1S)-2-[(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propoxy]-1-methyl-2- oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl] 2-methylpropanoate,
II-29: [(1S,2S)-2-(2,4-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-30: [(1S,2S)-2-(2,6-dimethylphenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
11-31: [(1S,2S)-2-[4-fluoro-2-(trifluoromethyl)phenyl]-1-methyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-32: [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-33: [(1S,2S)-1-methyl-2-[2-(trifluoromethyl)phenyl]propyl] (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate,
II-34: [(1S,2S)-2-(4-fluoro-2,6-dimethyl-phenyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-35: [(1S,2R)-2-(4-fluoro-2,6-dimethyl-phenyl)-1-methyl-propyl] (2S)-2-[(3-acetoxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate,
II-36: [(1R,2R)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate.
2. The mixture according to claim 1 , wherein active component 2) is at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-1, II-3, II-5, II-9, 11-11, 11-13, 11-14, 11-19, II-23, II-27, II-29, II-35 and II-36.
3. The mixture according to claim 1 , wherein active component 2) is at least one compound, or an N- oxide, or an agriculturally useful salt thereof, selected from the group consisting of 11-14 and II-36.
4. The mixture according to any one of claims 1 to 3, comprising a compound I and a compound II in a synergistically effective amount.
5. The mixture according to any one of claims 1 to 3, comprising a compound I and a compound II in a weight ratio of from 100:1 to 1 :100.
6. The mixture according to any one of claims 1 to 3, comprising a compound I and a compound 11 in a weight ratio of from 20: 1 to 1 :20.
7. The mixture according any one of claims 1 to 3, comprising a compound I and a compound II in a weight ratio of from 5:1 to 1:5.
8. An agrochemical composition, comprising a solvent or solid carrier and a composition according to any one of claims 1 to 7.
9. The agrochemical composition according to claim 8 further comprising seed in an amount of from 1 g to 1000 g active components per 100 kg of seed.
10. The non-therapeutic use of the mixture as defined in any one of claims 1 to 7 for controlling phytopathogenic harmful fungi.
11. The non-therapeutic use of the mixture as defined in any one of claims 1 to 7 for controlling phytopathogenic harmful fungi on soybeans.
12. The non-therapeutic use of the mixture as defined in any one of claims 1 to 7 for controlling Phakopsora pachyrhizi and P. meibomiae on soybeans.
13. The non-therapeutic use according to any one of claims 10 to 12, wherein the amount of compound 1-1 is in the range between 80 and 150 g/ha, and the amount of compound I-2 is in the range between 70 and 100 g/ha.
14. A method for controlling phytopathogenic harmful fungi, comprising treating the fungi, their habitat or the seed, the soil or the plants to be protected against fungal attack with an effective amount of the compound I and the compound II and the compound III as defined in any one of claims 1 to 7; with the exception of methods practiced for the therapeutic treatment of the human or animal body.
PCT/EP2021/059383 2020-04-14 2021-04-12 Fungicidal mixtures comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles WO2021209360A1 (en)

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