WO2021209360A1 - Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués - Google Patents

Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués 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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English (en)
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/pt
Publication of WO2021209360A1 publication Critical patent/WO2021209360A1/fr

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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

L'invention se rapporte à un mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués. Les mélanges fongicides selon la présente invention comprennent au moins un 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazole substitué (composé I) et au moins un composé actif II ; l'invention se rapporte à un procédé pour la lutte contre des champignons phytopathogènes nuisibles consistant à traiter les champignons, leur habitat ou les semences, le sol ou les plantes à protéger contre une attaque fongique au moyen d'une quantité efficace de mélanges comprenant les composés I et les composés II ; à l'utilisation des mélanges comprenant les composés I et les composés II pour lutter contre des champignons phytopathogènes nuisibles; à des compositions agrochimiques comprenant lesdits mélanges; et à des compositions agrochimiques comprenant en outre des semences.
PCT/EP2021/059383 2020-04-14 2021-04-12 Mélanges fongicides comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués WO2021209360A1 (fr)

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WO2023094592A1 (fr) * 2021-11-26 2023-06-01 Syngenta Crop Protection Ag Compositions fongicides

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