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WO2025078128A1 - Pyridazin-3-one-4-yloxadiazines comme nouveaux fongicides - Google Patents

Pyridazin-3-one-4-yloxadiazines comme nouveaux fongicides Download PDF

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Publication number
WO2025078128A1
WO2025078128A1 PCT/EP2024/076177 EP2024076177W WO2025078128A1 WO 2025078128 A1 WO2025078128 A1 WO 2025078128A1 EP 2024076177 W EP2024076177 W EP 2024076177W WO 2025078128 A1 WO2025078128 A1 WO 2025078128A1
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species
methyl
formula
chloro
compound
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Inventor
Lionel NICOLAS
Tomoki Tsuchiya
Vincent Thomas
Mathieu Gourgues
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • WO2020/127780 discloses oxadiazine compounds with different heterocyclic moieties as fungicides.
  • R 3 and R 4 are independently hydrogen, fluoro or C1-C4-alkyl
  • R 5 is hydrogen or C1-C4-alkyl
  • L is a direct bond or C1-C4-alkylene
  • said C1-C4-alkylene is optionally substituted with one or two substituents L SA , BCS233036 FC -2- L SA is fluoro, or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a cyclopropyl- or cyclobutyl-ring
  • R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C12-carbocyclyloxy, C6-C14-aryloxy, 5- to 14-
  • the present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable auxiliary.
  • the present invention also relates to the use of a compound of formula (I) as defined herein or a composition as defined herein for controlling phytopathogenic fungi.
  • the present invention relates to a method for controlling phytopathogenic fungi which comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.
  • the present invention also relates to processes and intermediates for preparing compounds of formula (I).
  • halogen refers to fluorine, chlorine, bromine or iodine atom.
  • oxo refers to an oxygen atom which is bound to a carbon atom or sulfur atom via a double bound.
  • C1-C6-alkyl refers to a saturated, branched or straight hydrocarbon chain having 1, 2, 3, 4, 5 or 6 carbon atoms.
  • said hydrocarbon chain has 1, 2, 3 or 4 carbon atoms (“C1-C4-alkyl”), e.g. methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso- butyl or tert-butyl.
  • C1-C6-haloalkyl refers to a C1-C6-alkyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • C3-C8-cycloalkyl examples include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Particularly, said cycloalkyl has 3 to 6 carbon atoms.
  • C3-C8-halocycloalkyl refers to a saturated hydrocarbon ring system in which all of the ring members, which vary from 3 to 8, are carbon atoms and in which which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • C2-C6-alkenyl refers to an unsaturated, branched or straight hydrocarbon chain having 2, 3, 4, 5 or 6 carbon atoms and comprising at least one double bond.
  • Examples of C2-C6-alkenyl include but are not limited to ethenyl (or "vinyl"), prop-2-en-1-yl (or “allyl”), prop-1-en-1-yl, but-3-enyl, but-2-enyl, but-1-enyl, pent-4-enyl, pent-3-enyl, pent-2-enyl, pent-1-enyl, hex-5-enyl, hex-4-enyl, hex-3- enyl, hex-2-enyl, hex-1-enyl, prop-1-en-2-yl (or “isopropenyl”), 2-methylprop-2-enyl, 1-methylprop-2- enyl, 2-methylprop-1-enyl, 1
  • C 3 -C 8 -cycloalkyloxy refers to a monocyclic, saturated cycloalkyloxy radical having 3 to 8 and preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a composite substituent, for example cycloalkoxyalkyl, unless defined elsewhere.
  • C1-C6-haloalkylsulfanyl refers to a C1-C6-alkylsulfanyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • C3-C8-cycloalkylsulfanyl refers to a saturated, monovalent, monocylic hydrocarbon ring which contains 3, 4, 5, 6, 7 or 8 carbon atoms and which is bound to the skeleton via a sulfur atom.
  • C1-C6-haloalkylcarbonyl refers to a C1-C6-alkylcarbonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
  • Heterocycles include but are not limited to 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (e.g. bicyclic or tricyclic) heterocycles.
  • the 3- to 14-membered heterocycle can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.
  • saturated heterocycles include but are not limited to 3-membered ring such as oxiranyl, aziridinyl, 4-membered ring such as azetidinyl, oxetanyl, thietanyl, 5-membered ring such as tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, 6-membered ring such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl,
  • Bicyclic heterocycles may consist of a monocyclic heteroaryl as defined herein fused to a monocyclic C3-C8-cycloalkyl, a monocyclic C3-C8-cycloalkenyl or a monocyclic heterocycle or may consist of a monocyclic heterocycle fused either to an aryl (e.g. phenyl), a C3-C8-cycloalkyl, a C3-C8- cycloalkenyl or a monocyclic heterocycle.
  • nitrogen atom may be at the bridgehead (e.g.
  • Examples include but are not limited to oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholiny
  • Preferred 3- to 7-membered heterocyclyl are oxiranyl, aziridinyl, azetidinyl, oxetanyl, tetrahydrofuranyl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl and thiomorpholinyl.
  • the term “5- to 14-membered heteroaryl” as used herein refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent.
  • 7- to 14-membered heteroaryl refers to a 7-, 8-, 9-, 10-, 11-,12-, 13- or 14- membered aromatic polycyclic (e.g. bicyclic or tricyclic) ring system containing 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur.
  • Bicyclic heteroaryls may consist of a monocyclic heteroaryl as defined herein fused to an aryl (e.g. phenyl) or to a monocyclic heteroaryl.
  • bicyclic heteroaryls include but are not limited to 9-membered ring such as indolyl, indolizinyl, isoindolyl, benzimadozolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl and benzisoxazolyl or 10-membered ring such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinal and benzodioxinyl.
  • 9-membered ring such as indolyl, indolizinyl, isoindolyl, benzimadozolyl, imidazopyridinyl, indazolyl, benzotriazolyl,
  • nitrogen atom may be at the bridgehead (e.g. imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl).
  • Examples of tricyclic aromatic heterocyle include but are not limited to carbazolyl, acridinyl and phenazinyl.
  • C 3 -C 12 -carbocyclyloxy designate a group of formula –O-R wherein R is respectively a C 3 -C 12 -carbocyclyl, a C 3 -C 8 -cycloalkyl, a C 6 -C 14 -aryl, a 5- to 14-membered heteroaryl or a 3- to 14-membered heterocyclyl group as defined herein.
  • BCS233036 FC -12- The term “leaving group” as used herein is to be understood as meaning a group which is displaced from a compound in a substitution or an elimination reaction, for example a halogen atom, a trifluoromethanesulphonate (“triflate”) group, alkoxy, methanesulphonate or p-toluenesulphonate. Not encompassed herein are compounds resulting from combinations which are against natural laws and which the person skilled in the art would therefore exclude based on his/her expert knowledge. For instance, ring structures having three or more adjacent oxygen atoms are excluded.
  • the compounds of formula (I) can suitably be in their free form, salt form, N-oxide form or solvate form (e.g.
  • the invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
  • the compound of formula (I) may be present in the form of the free compound and/or a salt thereof, such as an agrochemically active salt.
  • Agrochemically active salts include acid addition salts of inorganic and organic acids well as salts of customary bases.
  • Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated fatty acids having 6 to 20 carbon atoms, alkylsulphuric monoesters, alkylsulphonic acids (sulphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or aryl
  • R 7 is selected from methyl, ethyl, isopropryl, 4-pyridylmethyl and 2-methyl-allyl. Even more preferably, R 7 is methyl.
  • Q is a group of formula: wherein ⁇ 2 is the attachment to the oxygen atom, Q S1 is hydrogen or fluoro, Q S2 is chloro, fluoro, methyl, trifluoromethyl or cyclopropyl.
  • L is methylene and R 6 is phenyl, wherein said phenyl is optionally substituted with one or two R 6S substituents, wherein R 6S is independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, difluoromethyl and trifluoromethyl. More preferably, L is methylene and R 6 is a group of formula: wherein ⁇ 1 is the attachment to L, R 6S1 is chloro or methyl, R 6S2 is chloro or methyl.
  • the present invention relates, more preferably, to compounds of formula (I), wherein R 3 and R 4 are hydrogen, R 5 is hydrogen, L is methylene, R 6 is a group of formula: wherein ⁇ 1 is the attachment to L, R 6S1 is chloro or methyl, R 6S2 is chloro or methyl, BCS233036 FC -17- R 7 is methyl, Q is a group of formula: wherein ⁇ 2 is the attachment to the oxygen atom, Q S1 is hydrogen or fluoro, Q S2 is chloro, fluoro, methyl, trifluoromethyl or cyclopropyl, as well as salts, hydrates and hydrates of the salts thereof.
  • a compound of formula (I) may be directly obtained by performing process A to E or may be obtained by conversion or derivatization of another compound of formula (I) prepared in accordance with the processes described herein.
  • a compound of formula (I) can be converted into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) by other substituents.
  • the processes described herein may be suitably performed using one or more inert organic solvents which is/are customary for the considered reaction.
  • Suitable inert organic solvents can be chosen from the following: aliphatic, alicyclic or aromatic hydrocarbons (e.g.
  • nitriles e.g. acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile
  • amides e.g. N,N-dimethylformamide, N,N- dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide
  • sulfoxides e.g. dimethyl sulfoxide
  • sulfones e.g. sulfolane
  • ureas e.g.
  • inorganic or organic bases include, but are not limited to, alkaline earth metal or alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate), alkali metal hydrides (e.g. sodium hydride), alkaline earth metal or alkali metal hydroxides (e.g.
  • Suitable palladium salts or complexes include, but are not limited to, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), tris(dibenzyli- deneacetone)dipalladium(0), bis(triphenylphosphine)palladium(II) dichloride, [1,1’- bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(cinnamyl)dichlorodipalladium(II), bis(allyl)-dichlorodipalladium(II) or [1,1’-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II).
  • Compound of formula (4) can be obtained by: - reacting a compound of formula (1) wherein R 7 and Q are defined as above and U 1 is hydroxy, halogen or C1-C6-alkoxy, with an amine of formula (2) wherein R 3 , R 4 , R 5 , R 6 and L are defined as above and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4- methoxyphenyl)methyl,or one of its salts to provide a compound of formula (3) wherein R 3 , R 4 , R 5 , R 6 , R 7 L, Q and W are defined as above; and - removing the phtalimide group of compound (3) to provide a compound of formula (4).
  • reaction of compound of formula (7) with a compound of formula (8) may be performed in the presence of a base and optionally in presence of a suitable transition metal catalyst such as a copper salt or complex, and if appropriate in the presence of a ligand as described herein.
  • a suitable transition metal catalyst such as a copper salt or complex
  • Compounds of formula (5) are commercially available or can be prepared by hydrolysis of compound (18).
  • Compounds of formula (8) are commercially available or may be obtained by conversion or derivatization of another compound of formula (8) in accordance to well-known methods.
  • a compound of formula (I-a), wherein R 3 , R 4 , R 5 , R 6 , R 7 , L and Q are defined as above, can be prepared by a process comprising the steps of : - reacting a compound of formula (1), wherein R 7 , U 1 and Q are defined as above, with an amine of formula (13), wherein R 3 , R 4 , R 5 , R 6 and L are defined as above, E 1 is hydroxyl or halogen, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, or one of its salts to provide a compound of formula (14), wherein R 3 , R 4 , R 5 , R 6 , R 7 , E 1 , L, W and Q are defined as above, under similar conditions as described in process A, - treating a compound of formula (14) with a dehydrating agent followed by hydroxylamine to form a compound of formula (15), wherein R
  • Process F Preparation of compounds (1) (8) ( 5)
  • Process F may be performed in the presence of suitable transition metal catalyst salts or complexes, if appropriate in the presence of a ligand with compounds of formula (1), wherein U 1 is a C 1 -C 6 -alkoxy, as described in Eur. J. Org. Chem.2011, 18, 3353-3360.
  • Compounds of formula (5) are commercially available or can be prepared by hydrolysis of compound (18).
  • Compounds of formula (8) are commercially available or may be obtained by conversion or derivatization of another compound of formula (8) in accordance to well-known methods.
  • R 3 , R 4 , R 5 , L, R 6 , R 7 and Q given with regard to formula (I) apply mutatis mutandis.
  • the present invention also relates to compounds of formula (7): wherein R 3 , R 4 , R 5 , L, R 6 and R 7 are defined as in formula (I), X is halogen, preferably chloro or bromo.
  • X is halogen, preferably chloro or bromo.
  • the preferred, more preferred, even more preferred and most preferred definitions of R 3 , R 4 , R 5 , L, R 6 and R 7 given with regard to formula (I) apply mutatis mutandis.
  • the present invention also relates to compounds of formula (10): wherein Q and R 7 is defined as in formula (I).
  • the present invention also relates to compounds of formula (14) and (15): wherein R 3 , R 4 , R 5 , L, R 6 and R 7 are defined as in formula (I), E 1 is hydroxyl or halogen, preferably hydroxyl, chloro or bromo, E 2 is hydroxyl, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
  • R 3 , R 4 , R 5 , L, R 6 and R 7 are defined as in formula (I)
  • E 1 is hydroxyl or halogen, preferably hydroxyl, chloro or bromo
  • E 2 is hydroxyl
  • W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
  • BCS233036 FC -32- The present invention also relates to compounds of formula (16) and (17): wherein R 3 , R 4 , R 5 , L, R 6 and R 7 are defined as in formula (I), X is halogen, preferably, chloro or bromo, E 1 is hydroxyl or halogen, preferably hydroxyl, chloro or bromo, E 2 is hydroxyl, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
  • R 3 , R 4 , R 5 , L, R 6 and R 7 are defined as in formula (I)
  • X is halogen, preferably, chloro or bromo
  • E 1 is hydroxyl or halogen, preferably hydroxyl, chloro or bromo
  • E 2 is hydroxyl
  • W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
  • typically useful solid carriers for preparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.
  • suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic BCS233036 FC -33- and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as ethanol, propanol, butanol, benzylalcohol, cyclohexanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstitute
  • surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (for example, polyoxyethylene fatty acid esters such as castor oil ethoxylate, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and ethoxylates thereof (such as tristyrylphenol ethoxylate), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols (such a fatty acid esters of g,
  • auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners and secondary thickeners (such as cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, e.g. the products available under the name Bentone, and finely divided silica), stabilizers (e.g.
  • the term "effective amount” is an amount, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of formula (I) used.
  • the composition according to the invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferred from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of formula (I). It is possible BCS233036 FC -35- that a composition comprises two or more compounds of the invention.
  • composition types examples include solutions, watersoluble concentrates (e.g. SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (e.g. SC, OD, OF, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME, SE), 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.
  • watersoluble concentrates e.g. SL, LS
  • DC dispersible concentrates
  • suspensions and suspension concentrates e.g. SC, OD, OF, FS
  • emulsifiable concentrates e.g. EC
  • emulsions e.g. EW, EO, ES, ME, SE
  • capsules
  • the outlined amount of compound of the invention refers to the total amount of compounds of the present invention. This applies mutatis mutandis for any further component of the composition, if two or more representatives of such component, e.g. wetting agent, binder, are present.
  • Water-soluble concentrates (SL, LS) 10-60 % by weight of at least one compound of formula (I) and 5-15 % by weight surfactant (e.g. polyoxyethylene fatty alcohol ether) are dissolved in such amount of water and/or water-soluble solvent (e.g. alcohols such as propylene glycol or carbonates such as propylene carbonate) to result in a total amount of 100 % by weight.
  • surfactant e.g. polyoxyethylene fatty alcohol ether
  • water-soluble solvent e.g. alcohols such as propylene glycol or carbonates such as propylene carbonate
  • Dispersible concentrates 5-25 % by weight of at least one compound of formula (I) and 1-10 % by weight surfactant and/or binder (e.g. polyvinylpyrrolidone) are dissolved in such amount of organic solvent (e.g. cyclohexanone) to result in a total amount of 100 % by weight. Dilution with water gives a dispersion.
  • Emulsifiable concentrates EC 15-70 % by weight of at least one compound of formula (I) and 5-10 % by weight surfactant (e.g.
  • Emulsions (EW, EO, ES) 5-40 % by weight of at least one compound of formula (I) and 1-10 % by weight surfactant (e.g.
  • Water-dispersible granules and water-soluble granules (WG, SG) 50-80 % by weight of at least one compound of formula (I) are ground finely with addition of surfactant (e.g. sodium lignosulfonate and polyoxyethylene fatty alcohol ether) and converted to water-dispersible or water- soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed).
  • the surfactant is used in such amount to result in a total amount of 100 % by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • surfactant e.g. sodium lignosulfonate
  • binder e.g. carboxymethylcellulose
  • Microemulsion (ME) 5-20 % by weight of at least one compound of formula (I) are added to 5-30 % by weight organic solvent blend (e.g.
  • a polyamine e.g. hexamethylenediamine
  • the monomers amount to 1-10 % by weight of the total CS composition.
  • Dustable powders (DP, DS) 1-10 % by weight of at least one compound of formula (I) are ground finely and mixed intimately with such amount of solid carrier, e.g. finely divided kaolin, to result in a total amount of 100 % by weight.
  • Granules (GR, FG) 0.5-30 % by weight of at least one compound of formula (I) are ground finely and associated with such amount of solid carrier (e.g. silicate) to result in a total amount of 100 % by weight.
  • biological control is defined as control of harmful organisms such as a phytopathogenic fungi and/or insects and/or acarids and/or nematodes by the use or employment of a biological control agent.
  • biological control agent is defined as an organism other than the harmful organisms and / or proteins or secondary metabolites produced by such an organism for the purpose of biological control.
  • Known mechanisms of biological control agents comprise enteric bacteria that control root rot by out-competing fungi for space on the surface of the root.
  • Bacterial toxins such as antibiotics, have been used to control pathogens.
  • the toxin can be isolated and applied directly to the plant or the bacterial species may be administered so it produces the toxin in situ.
  • a ”variant is a strain having all the identifying characteristics of the NRRL or ATCC Accession Numbers as indicated in this text and can be identified as having a genome that hybridizes under conditions of high stringency to the genome of the NRRL or ATCC Accession Numbers.
  • Hybridization refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized via hydrogen bonding between the bases of the nucleotide residues.
  • the hydrogen bonding may occur by Watson-Crick base pairing, Hoogstein binding, or in any other sequence-specific manner.
  • the complex may comprise two strands forming a duplex structure, three or more strands forming a multi-stranded complex, a single self-hybridizing strand, or any combination of these.
  • Hybridization reactions can be performed under conditions of different “stringency”. In general, a low stringency hybridization reaction is carried out at about 40 °C in 10 X SSC or a solution of equivalent ionic strength/temperature.
  • biological control agents which may be combined with the compound of formula (I) and the composition of the invention are: (A) Antibacterial agents selected from the group of: (A1) bacteria, such as (A1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661, U.S. Patent No.6,060,051); (A1.2) Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL ® from Kumiai Chemical Industry Co., Ltd.), having Accession No. FERM BP-8234, U.S.
  • A1 bacteria such as (A1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661, U.S. Patent No.6,060,051)
  • NRRL B-21856 (available as BLOOMTIME BIOLOGICAL TM FD BIOPESTICIDE from Northwest Agri Products); and (A2) fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 ormixtures of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR ® and BLOSSOM PROTECT ® from bio-ferm, CH); (A2.2) Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem); (A2.3) Saccharomyces cerevisiae, in particular strains CNCM No.
  • Aureobasidium pullulans in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 ormixtures of blastospores of strains DSM14940 and D
  • Esquive® WP from Agrauxine, FR (B2.39) Trichoderma atroviride, strain no. V08/002387; (B2.40) Trichoderma atroviride, strain NMI no. V08/002388; (B2.41) Trichoderma atroviride, strain NMI no. V08/002389; (B2.42) Trichoderma atroviride, strain NMI no. V08/002390; (B2.43) Trichoderma atroviride, strain BCS233036 FC -50- LC52 (e.g.
  • CABI 353812 (e.g. BIOKUPRUM TM by AgriLife); (B2.91) Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell walls (CEREVISANE ® from Lesaffre; ROMEO ® from BASF SE), strains CNCM No. I- BCS233036 FC -51- 3936, CNCM No. I-3937, CNCM No. I-3938, CNCM No.
  • NRRL B-5015 a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO ® BCS233036 FC -52- (WG), PRESENCE ® (WP) from FMC Corporation); Bacillus cereus, in particular strain BP01 (ATCC 55675; e.g. MEPICHLOR ® from Arysta Lifescience, US); Bacillus subtilis, in particular strain MBI 600 (e.g. SUBTILEX ® from BASF SE); Bradyrhizobium japonicum (e.g.
  • Azorhizobium caulinodans in particular strain ZB-SK-5; Azotobacter chroococcum, in particular strain H23; Azotobacter vinelandii, in particular strain ATCC 12837; Bacillus siamensis, in particular strain KCTC 13613T; Bacillus tequilensis, in particular strain NII- 0943; Serratia marcescens, in particular strain SRM (Accession No. MTCC 8708); Thiobacillus sp. (e.g.
  • C2 fungi selected from the group consisting of Purpureocillium lilacinum (previously known as Paecilomyces lilacinus) strain 251 (AGAL 89/030550; e.g. BioAct from Bayer CropScience Biologics GmbH)Penicillium bilaii, strain ATCC 22348 (e.g. JumpStart ® from Acceleron BioAg), Talaromyces flavus,strain V117b; Trichoderma atroviride strain CNCM I-1237 (e.g. Esquive® WP from Agrauxine, FR), Trichoderma viride, e.g.
  • Purpureocillium lilacinum previously known as Paecilomyces lilacinus
  • strain ATCC 22348 e.g. JumpStart ® from Acceleron BioAg
  • Talaromyces flavus strain V117b
  • the compound of formula (I) and the composition of the invention may be combined with one or more active ingredients selected from insecticides, acaricides and nematicides.
  • Insecticides as well as the term “insecticidal” refers to the ability of a substance to increase mortality or inhibit growth rate of insects.
  • the term “insects” comprises all organisms in the class “Insecta”.
  • “Nematicide” and “nematicidal” refers to the ability of a substance to increase mortality or inhibit the growth rate of nematodes.
  • nematode comprises eggs, larvae, juvenile and mature forms of said organism.
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as, for example, spinosyns, e.g. spinetoram and spinosad.
  • Microbial disruptors of the insect gut membrane such as, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacill
  • chlorantraniliprole, cyantraniliprole and flubendiamide further active compounds such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imid
  • BCS233036 FC -59- Examples of herbicides which could be mixed with the compound of formula (I) and the composition of the invention are: Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H- indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin,
  • nitrification inhibitors wich can be mixed with the compound of formula (I) and the composition of the invention are selected from the group consisting of 2-(3,4-dimethyl-1 H-pyrazol-1 - yl)succinic acid, 2-(4,5-dimethyl-1 H-pyrazol-1 -yl)succinic acid, 3,4-dimethyl pyrazolium glycolate, 3,4- dimethyl pyrazolium citrate, 3,4-dimethyl pyrazolium lactate, 3,4-dimethyl pyrazolium mandelate, 1 ,2,4- triazole, 4-Chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazole-1-yl)methyl)acetamide, N-((3(5)- methyl-1 H-pyrazole-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazole-1-yl)methyl)formamide, N- ((
  • fungicide refers to a compound or composition that can be used in crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and/or for the control of Oomycetes.
  • the compound of formula (I) and the composition of the invention may also be used as antibacterial agent.
  • the compound of formula (I) and the composition of the invention may have effects on diseases from plant viruses, such as the tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leaf curl virus (VLCV), tobacco nervilia mosaic virus (TVBMV), tobacco necrotic dwarf virus (TNDV), tobacco streak virus (TSV), potato virus X (PVX), potato viruses Y, S, M, and A, potato acuba mosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf-roll virus (PLRV), alfalfa mosaic virus (AMV), cucumber mosaic virus (CMV), cucumber green mottlemosaic virus (CGMMV), cucumber yellows virus (CuYV), watermelon mosaic virus (WMV), tomato spotted wilt virus (TSWV), tomato ringspot virus (TomRSV), sugarcane mosaic virus (SCMV), rice drawf virus, rice stripe virus, rice black-streaked drawf virus, strawberry mottle virus (SMoV), strawberry vein banding virus (SVBV), strawberry
  • the harmful microorganisms are pathogenic oomycetes or phytopathogenic fungi selected from the group consisting of Podosphaera species, Sphaerotheca species, Uncinula species, Gymnosporangium species, Hemileia species, Phakopsora species, Puccinia species, Uromyces species, Albugo species, Bremia species, Peronospora species, Phytophthora species, Plasmopara species, Pseudoperonospora species, Pythium species, Alternaria species, Cercospora species, Cladiosporium species, Cochliobolus species, Corynespora species, Cycloconium species, Diaporthe species, Elsinoe species, Gloeosporium species, Glomerella species, Guignardia species, Leptosphaeria species, Magnaporto
  • BCS233036 FC -65- Typically, when the compound of formula (I) and the composition of the invention are used in curative or protective methods for controlling phytopathogenic fungi and/or phytopathogenic oomycetes, an effective and plant-compatible amount thereof is applied to the plants, plant parts, fruits, seeds or to the soil or substrates in which the plants grow.
  • Suitable substrates that may be used for cultivating plants include inorganic based substrates, such as mineral wool, in particular stone wool, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum based substrates such as polymeric foams or plastic beads.
  • Effective and plant-compatible amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the crop growth stage, the climatic conditions and the respective compound or composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art. Plants and plant parts The compound of formula (I) and the composition of the invention may be applied to any plants or plant parts. Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
  • Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • Plants which may be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp.
  • Theaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Cicurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • Papilionaceae sp. for example peas
  • major crop plants such as Gramineae sp.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. Plants and plant cultivars which may be treated by the above disclosed methods include those plants which are resistant to one or more abiotic stresses.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses.
  • Transgenic plants, seed treatment and integration events The compound of formula (I) can be advantageously used to treat transgenic plants, plant cultivars or plant parts that received genetic material which imparts advantageous and/or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention may be combined with one or more recombinant traits or transgenic event(s) or a combination thereof.
  • a transgenic event is created by the insertion of a specific recombinant DNA BCS233036 FC -67- molecule into a specific position (locus) within the chromosome of the plant genome.
  • the insertion creates a novel DNA sequence referred to as an “event” and is characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to/flanking both ends of the inserted DNA.
  • Such trait(s) or transgenic event(s) include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance, in which the trait is measured with respect to a plant lacking such trait or transgenic event.
  • Such advantageous and/or useful properties are better plant growth, vigor, stress tolerance, standability, lodging resistance, nutrient uptake, plant nutrition, and/or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to levels of water or soil salinity, enhanced flowering performance, easier harvesting, accelerated ripening, higher yields, higher quality and/or a higher nutritional value of the harvested products, better storage life and/or processability of the harvested products, and increased resistance against animal and microbial pests, such as against insects, arachnids, nematodes, mites, slugs and snails.
  • Bt Cry or VIP proteins which include the CrylA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof and also hybrids or combinations thereof, especially the CrylF protein or hybrids derived from a CrylF protein (e.g. hybrid CrylA-CrylF proteins or toxic fragments thereof), the CrylA-type proteins or toxic fragments thereof, preferably the CrylAc protein or hybrids derived from the CrylAc protein (e.g.
  • hybrid CrylAb-CrylAc proteins or the CrylAb or Bt2 protein or toxic fragments thereof, the Cry2Ae, Cry2Af or Cry2Ag proteins or toxic fragments thereof, the CrylA.105 protein or a toxic fragment thereof, the VIP3Aa19 protein, the VIP3Aa20 protein, the VIP3A proteins produced in the COT202 or COT203 cotton events, the VIP3Aa protein or a toxic fragment thereof as described in Estruch et al.
  • any variants or mutants of any one of these proteins differing in some amino acids (1-10, preferably 1-5) from any of the above named sequences, particularly the sequence of their toxic fragment, or which are fused to a transit peptide, such as a plastid transit peptide, or another protein or peptide, is included herein.
  • a transit peptide such as a plastid transit peptide, or another protein or peptide
  • Another and particularly emphasized example of such properties is conferred tolerance to one or more herbicides, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin.
  • Particularly useful transgenic events in transgenic plants or plant cultivars which can be treated with preference in accordance with the invention include Event 531/ PV-GHBK04 (cotton, insect control, described in WO2002/040677), Event 1143-14A (cotton, insect control, not deposited, described in WO2006/128569); Event 1143-51B (cotton, insect control, not deposited, described in WO2006/128570); Event 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002- 120964 or WO2002/034946); Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO2010/117737); Event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO2010/117735); Event 281-24-236 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, described in WO2005/103266 or US-A 2005-216969); Event 3006-210-23 (cotton, insect control - herb
  • Event BLRl (oilseed rape, restoration of male sterility, deposited as NCIMB 41193, described in WO2005/074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US-A 2009-217423 or WO2006/128573); Event CE44-69D (cotton, insect control, not deposited, described in US-A 2010- 0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO2006/128571); Event CE46-02A (cotton, insect control, not deposited, described in WO2006/128572); Event COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO2004/039986); Event COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005/054479); Event COT203 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas and other types of vegetable, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis being given to maize, soya beans, wheat, rice, potatoes, cotton, sugar cane, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and slugs and snails, as well as the increased resistance of the plants to one or more herbicides.
  • pathogens of fungal diseases which may be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces append
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).
  • Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac- DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F.
  • verticillioides and also by Aspergillus spec., such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec. and others.
  • Aspergillus spec. such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citr
  • the compound of formula (I) and the composition of the invention may also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • the compound of formula (I) and the composition of the invention may be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings for example BCS233036 FC -76- cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compound of formula (I) and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould. In the case of treatment of wood the compound of formula (I) and the composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
  • Timber means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the compound of formula (I) and the composition of the invention may be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • the compound of formula (I) and the composition of the invention may also be employed for protecting storage goods.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, may be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the compound of formula (I) and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compound of formula (I) and the composition of the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae.
  • the treatment of seeds with the compound of formula (I) or the composition of the invention protects the seeds from phytopathogenic microorganisms, but also protects the germinating seeds, the emerging seedlings and the plants after emergence from the treated seeds. Therefore, the present invention also relates to a method for protecting seeds, germinating seeds and emerging seedlings.
  • the seeds treatment may be performed prior to sowing, at the time of sowing or shortly thereafter. When the seeds treatment is performed prior to sowing (e.g.
  • seeds which have been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits For example, it is possible to use seeds which have been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds which, after drying, for example, have been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
  • the amount of the compound of formula (I) or the composition of the invention applied to the seeds is typically such that the germination of the seed is not impaired, or that the resulting plant is not damaged.
  • the intrinsic phenotypes of transgenic plants should also be taken into consideration when determining the amount of the compound of formula (I) to be applied to the seed in order to achieve optimum seed and germinating plant protection with a minimum amount of compound being employed.
  • BCS233036 FC -78- The compound of formula (I) can be applied as such, directly to the seeds, i.e. without the use of any other components and without having been diluted. Also the composition of the invention can be applied to the seeds.
  • the compound of formula (I) and the composition of the invention are suitable for protecting seeds of any plant variety.
  • the compound of formula (I) can be applied as such, or for example in the form of as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with the compound of formula (I), synthetic substances impregnated with the compound of formula (I), fertilizers or microencapsulations in polymeric substances.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming or spreading-on.
  • the compound of formula (I) can be applied to a crop plant according to appropriate dose regime if a model models the development of a fungal disease and calculates that a threshold has been reached for which it is recommendable to apply the compound of formula (I) to the crop plant.
  • agronomic models are e.g. FieldScripts TM from The climate Corporation, Xarvio TM from BASF, AGLogic TM from John Deere, etc.
  • the compound of formula (I) can also be used in combination with smart spraying equipment such as e.g.
  • Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • input sensors such as e.g. a camera
  • processing unit configured to analyze the input data and configured to provide a decision based on the analysis of the input data to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner.
  • the use of such smart spraying equipment usually also requires positions systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the spraying.
  • GPS geographic information systems
  • fungal diseases can be detected from imagery acquired by a camera.
  • fungal diseases can be identified and/or classified based on that imagery.
  • identification and/ classification BCS233036 FC -80- can make use of image processing algorithms.
  • image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed. Aspects of the present teaching may be further understood in light of the following examples, which should not be construed as limiting the scope of the present teaching in any way.
  • the peak list of an example has therefore the form: ⁇ 1 (intensity 1 ); ⁇ 2 (intensity 2 );........; ⁇ i (intensity i ); hence; ⁇ n (intensity n )
  • Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
  • For calibrating chemical shift for 1 H spectra we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO.
  • the peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%). Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via “side-products-fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods (MestreC, ACD- simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1 H-NMR interpretation.
  • Step 3 Preparation of 5-(3-cyclopropylphenoxy)-4-[(5RS)-5-(3,4-dimethylbenzyl)-5,6-dihydro-4H- 1,2,4-oxadiazin-3-yl]-2-methylpyridazin-3(2H)-one (compound I-001) N-[(2RS)-1-chloro-3-(3,4-dimethylphenyl)propan-2-yl]-5-(3-cyclopropylphenoxy)-N'-hydroxy-2- methyl-3-oxo-2,3-dihydropyridazine-4-carboximidamide (intermediate 15-001) (174 mg, 0.36 mmol) was dissolved into 3.6 mL of isopropanol.
  • the young plants of barley were treated by spraying the active ingredient prepared as described above.
  • Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ® 80. After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores.
  • the contaminated barley plants were incubated for 48 hours at 20°C and at 100% relative humidity and then for 8 days at 20°C and at 70-80% relative humidity.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores.
  • the contaminated gherkin plants were incubated for 8 days at 20°C and at 70-80% relative humidity.
  • the test was evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-001; I-002; I-003; I-004; I-005; I-006; I-007 B-5.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores.
  • the contaminated bean plants were incubated for 24 hours at 20°C and at 100% relative humidity and then for 6 days at 20°C and at 90% relative humidity.
  • the test was evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-003; I-004; I-005; I-006; I-007 B-6.
  • Alternaria alternata in vitro cell test Solvent: DMSO Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1liter Inoculum: spores suspension Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ⁇ 1%. A spore suspension of A. alternata was prepared and diluted to the desired spore density. Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay.
  • Fusarium culmorum in vitro cell test Solvent DMSO Culture medium: 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1liter Inoculum: spore suspension BCS233036 FC -93- Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ⁇ 1%. A spore suspension of F. culmorum was prepared and diluted to the desired spore density. Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay.
  • the compounds were added in the desired concentration to the culture medium with spores. After 4 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides. B-8.
  • DMSO Culture medium 14.6g anhydrous D-glucose (VWR), 7.1g Mycological Peptone (Oxoid), 1.4g granulated Yeast Extract (Merck), QSP 1liter
  • Inoculum spores suspension BCS233036 FC -94- Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ⁇ 1%. A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.
  • Fungicides were evaluated for their ability to inhibit spores germination and mycelium growth in liquid culture assay.
  • the compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides. In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 ⁇ Mol/l of active ingredient: I-001; I-002; I-003; I-004; I-005; I-006; I-007 B-10.
  • Septoria tritici in vitro cell test Solvent DMSO Culture medium: 1g KH2PO4 (VWR), 1g K2HPO4 (VWR), 0.5g Urea (VWR), 3g KNO3 (Prolabo), 10g saccharose (VWR), 0.5g MgSO4, 7H2O (Sigma), 0.07g CaCl2, 2H2O (Prolabo), 0.2mg MnSO4, H2O (Sigma), 0.6mg CuSO4, 5H2O (Sigma), 7.9mg ZnSO4, 7H2O (Sigma), 0.1mg H3BO3 (Merck), 0.14mg NaMoO4, 2H2O (Sigma), 2mg thiamine (Sigma), 0.1mg biotine (VWR), 4mg FeSO4, 7H2O (Sigma), QSP 1liter Inoculum: spore suspension Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations.
  • the final concentration of DMSO used in the assay was ⁇ 1%.
  • a spore suspension of P. teres was prepared and diluted to the desired spore density.
  • Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay.
  • the compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
  • Fusarium culmorum in vitro cell test Solvent DMSO Culture medium: 1g KH2PO4 (VWR), 1g K2HPO4 (VWR), 0.5g Urea (VWR), 3g KNO3 (Prolabo), 10g saccharose (VWR), 0.5g MgSO4, 7H2O (Sigma), 0.07g CaCl2, 2H2O (Prolabo), 0.2mg MnSO4, H2O (Sigma), 0.6mg CuSO4, 5H2O (Sigma), 7.9mg ZnSO4, 7H2O (Sigma), 0.1mg H3BO3 (Merck), 0.14mg NaMoO4, 2H2O (Sigma), 2mg thiamine (Sigma), 0.1mg biotine (VWR), 4mg FeSO4, 7H2O (Sigma), QSP 1liter Inoculum: spores suspension BCS233036 FC -97- Fungicides were solubilized in DMSO, and the solution used to

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Abstract

La présente invention concerne des pyridazin-3-one-4-yloxadiazines et leurs utilisations pour lutter contre des micro-organismes phytopathogènes tels que des champignons phytopathogènes. L'invention concerne également des procédés et des intermédiaires pour préparer ces composés.
PCT/EP2024/076177 2023-10-11 2024-09-19 Pyridazin-3-one-4-yloxadiazines comme nouveaux fongicides Pending WO2025078128A1 (fr)

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