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WO2025078263A1 - Dérivés de pyridyl pyrazole microbiocides - Google Patents

Dérivés de pyridyl pyrazole microbiocides Download PDF

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Publication number
WO2025078263A1
WO2025078263A1 PCT/EP2024/077866 EP2024077866W WO2025078263A1 WO 2025078263 A1 WO2025078263 A1 WO 2025078263A1 EP 2024077866 W EP2024077866 W EP 2024077866W WO 2025078263 A1 WO2025078263 A1 WO 2025078263A1
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Prior art keywords
alkyl
alkoxy
cyano
halogen
formula
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Inventor
Andrew Edmunds
Christopher Charles SCARBOROUGH
Atul Mahajan
Matthias Weiss
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Syngenta Crop Protection AG Switzerland
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Syngenta Crop Protection AG Switzerland
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Publication of WO2025078263A1 publication Critical patent/WO2025078263A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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

Definitions

  • the present invention relates to microbiocidal pyrazole derivatives, e.g., as active ingredients, which have microbiocidal activity, in particular fungicidal activity.
  • the invention also relates to preparation of these pyrazole derivatives, to intermediates useful in the preparation of these pyrazole derivatives, to the preparation of these intermediates, to agrochemical compositions which comprise at least one of the pyrazole derivatives, to preparation of these compositions and to the use of the pyrazole derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.
  • R 1 is selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl
  • R 2 is selected from hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3- C6-cycloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy- C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, N-C 1 -C 4 -alkoxy-C-C
  • an intermediate compound of formula (IIb) as respectively described in the invention can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C1- C4alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic 82953 FF 4 acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfate, for example with organic carboxylic acids, such as mineral acids, for example perchloric acid, sulfuric acid
  • Compounds of formula (I) which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.
  • bases for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts
  • salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower-alkylamine, for example ethyl-, die
  • substituents are indicated as being “optionally substituted”, this means that they may or may not carry one or more identical or different substituents, e.g., one, two or three R x substituents.
  • C1-C6alkyl substituted by 1, 2 or 3 halogens may include, but not be limited to, -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, - CF3, -CH2CF3 or -CF2CH3 groups.
  • C1-C6alkoxy substituted by 1, 2 or 3 halogens may include, but not be limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.
  • optionally substituted can be used interchangeably with the term “unsubstituted or substituted”.
  • halogen or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine, or bromine.
  • halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, and halocycloalkyl.
  • amino means a -NH2 group.
  • cyano means a -CN group.
  • hydroxyl or “hydroxy” means an -OH group.
  • carboxylic acid means a -COOH group.
  • C1-Cn-alkylene refers to the corresponding definition of C1-Cn-alkyl, except that such 82953 FF 5 radical is attached to the rest of the molecule by two single bonds.
  • the term “C1-Cn-alkylene” is to be construed accordingly. Examples of C1-Cn-alkylene, include, but are not limited to, -CH 2 -, -CH 2 CH 2 - and -(CH 2 ) 3 -.
  • C 2 -C n -alkenyl refers to a straight or branched alkenyl chain moiety having from two to n carbon atoms and one or two double bonds, for example, ethenyl, prop-1-enyl, but-2-enyl.
  • C2-Cn- alkenylene group refers to the corresponding definition of C2-Cn-alkenyl, except that such radical is attached to the rest of the molecule by two single bonds.
  • C3-Cn-cycloalkyl refers to three (3) to n membered cycloalkyl radical such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • C1-Cn-alkoxy refers to a straight-chain or branched saturated alkyl radical having one (1) to n carbon atoms (as mentioned above) which is attached via an oxygen atom, i.e., for example, any one of the radicals methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy.
  • C2-Cn-alkenyloxy refers to a straight-chain or branched alkenyl chain having two (2) to n carbon atoms (as mentioned above) which is attached via an oxygen atom.
  • C2-Cn-alkynyloxy refers to a radical of the formula -ORa where Ra is a C2-Cn-alkynyl radical as generally defined above.
  • C1-Cn-alkoxy-C1-Cn-alkyl refers to an alkyl radical (as mentioned above) substituted with a C1-Cn-alkoxy group.
  • Examples are cyclopropylmethyl, cyclopropylethyl.
  • C3-Cn-halocycloalkyl-C1-Cn-alkyl refers to an alkyl radical substituted with cycloalkyl group, wherein the cycloalkyl group is substituted by one or more of the same or different halogen atoms. Examples are 3,3- difluorobutylmethyl and 1-chlorocyclopropylmethyl.
  • cyano-C1-Cn-alkyl refers to C1-Cn-alkyl radical having 1 to n carbon atoms (as mentioned above), where one of the hydrogen atoms in the radical is be replaced by a cyano group: for example, cyano-methyl, 2-cyano-ethyl, 2-cyano-propyl, 3-cyano-propyl, 1-(cyano-methyl)-2-ethyl, 1-(methyl)- 2-cyano-ethyl, 4-cyanobutyl, and the like.
  • C 1 -C 2 fluoroalkyl would refer to a C 1 -C 2 alkyl radical which carries 1, 2, 3, 4, or 5 fluorine atoms, for example, any one of difluoromethyl, trifluoromethyl, 1- fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.
  • C1-Cn-alkylthio“ or “C1-Cn-alkylsulfanyl“ refers to a C1-Cn-alkyl group linked through a sulfur atom.
  • heterocyclic ring or heterocycle comprising 1, 2 or 3 heteroatoms" or “containing heteroatom groups", wherein those heteroatom(s) (group(s) are selected from N, O, S, NO, SO and SO2 and are ring members, or selected from N, O and S and are ring members, refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • 4-, 5-, or 6-membered saturated heterocyclic rings or heterocycles include, but are not limited to: 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazolidin
  • Examples of 4-, 5-, or 6-membered partially unsaturated heterocyclic rings or heterocycles include: 2,3- dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3- dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3- pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4- isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isox
  • Examples of 5- or 6-membered aromatic heterocyclic rings or heterocycles also termed heteroaromatic rings or heteroaryl, include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5- pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5- pyrimidinyl and 2-pyrazinyl.
  • heterocyclyl refers to a stable 4-, 5- or 6-membered non-aromatic monocyclic ring radical which comprises 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur, with the proviso of only one O or S.
  • the heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heteroaryl examples include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.
  • heteroaryl-C1-Cn-alkyl or “heteroaryl- C3-Cn-cycloalkyl” refers to an C1-Cn-alkyl or C3-Cn-cycloalkyl radical respectively substituted by a heteroaryl group.
  • R 2 is hydrogen, halogen, C1-C3 alkyl, C3-C6-cycloalkyl, C1-C3alkoxy, C1-C3-alkoxy-C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkoxy, C1-C3-alkoxy-C1-C3- alkoxy-C1-C3-alkyl, C1-C3-alkylcarbonyl, N-C1-C3-alkoxy-C-C1-C3-alkyl-carbonimidoyl, N-hydroxy-C-C1-C3- alkyl-carbonimidoyl, or C1-C3-alkoxycarbonyl.
  • R 2 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2-alkoxy-C1-C2-alkyl, C1-C2-alkoxy-C1-C2-alkoxy, C1-C2-alkoxy-C1-C2-alkoxy-C1-C2-alkyl, acetyl, or N-C1-C2-alkoxy-C-C1-C2-alkyl-carbonimidoyl.
  • R 2 is hydrogen, chlorine, methyl, cyclopropyl, methoxy, methoxymethyl, methoxyethoxy, 2-methoxyethoxymethyl.
  • R 3 is hydrogen, halogen, C1-C4-haloalkyl, C1-C4-alkyl, C1-C4-alkoxy, or C3- C6-cycloalkyl.
  • R 3 is hydrogen, C1-C4-alkyl, or C1-C4-alkoxy. More preferably R 3 is hydrogen, C1-C3- 82953 FF 10 alkyl, or C1-C3-alkoxy.
  • R 3 is hydrogen, methyl, ethyl, or methoxy.
  • R 3 is hydrogen, methyl, or methoxy. Still even more preferably R 3 is hydrogen.
  • R 5 is selected from hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy, or C 1 -C 4 -alkoxy-C 1 -C 4 - alkoxy-C1-C4-alkyl.
  • R 4 is selected from hydrogen, halogen, or C1-C4-alkyl.
  • R 4 is halogen, or C1-C3-alkyl. Even more preferably R 4 is chlorine, or methyl.
  • R 5 is selected from hydrogen, halogen, or C1-C4-alkyl.
  • R 5 is halogen, or C1-C3-alkyl. Even more preferably R 5 is chlorine, or methyl.
  • R 4 is selected from halogen, or C1-C4-alkyl; and R 5 is hydrogen; or R 4 is hydrogen; and R 5 is selected from halogen, or C1-C4-alkyl.
  • W 2 is selected from O, NR 14 , or *-NR 15 O-#, wherein the star(*) denotes the connection to the pyridine-moiety and the # the connection to Z 2 .
  • W 2 is O, or NR 14 . More preferably W 2 is O, or NH.
  • Z 1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, wherein any of said alkyl, alkenyl and alkynyl is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C1-C2 alkoxy, C1-C2 alkylcarbamoyl, cyano, phenyl, a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle, or cyclopropyl; and wherein said cyclopropyl group is unsubstituted or substituted with 1 substituent selected from cyano; wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms selected from O, S or N, with the proviso that no more than one is O or S; and wherein said any of said phenyl and 4-, 5- or 6-membered saturated, partially 82953 FF 14
  • Z 1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, wherein any of said alkyl, alkenyl and alkynyl is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C1-C3alkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C2 haloalkyl, C1-C2 alkoxy, C1-C2alkoxy-C1-C2alkyl, C1-C2alkoxy-C1-C2alkoxy, C1-C2haloalkoxy, di(C1-C2alkyl)carbamoyl, C1-C2 alkylcarbamoyl, C1-C2alkylsulfanyl, C1-C2alkylsulfinyl, C1-C2alkylsulfon
  • Z 1 is phenyl, wherein said phenyl is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, trifluoromethyl, difluoromethyl, methyl, vinyl, prop-1-enyl, ethynyl, prop- 1-ynyl, cyano, carbamoyl, dimethylcarbamoyl, methylcarbamoyl, methoxymethyl, 2-methoxyethoxy, cyanomethyl, 2-cyanoethyl, 1-cyano-ethyl, 1-cyano-1-methyl-ethyl, methoxycarbonylmethyl, 2- methoxycarbonylethyl, 1-methoxycarbonylethyl, 1-methoxycarbonylethyl, 1-methoxycarbonyl-1-methyl-ethyl, hydroxycarbonymethyl, 1- hydoxyoxycarbonyl-1-methyl-ethyl, 2-hydroxycarbonylethyl, carbamoylmethyl,
  • Z 2 is selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, wherein any of said alkyl, alkenyl, and alkynyl is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkoxy, C1-C4 haloalkoxy, di(C1-C4alkyl)carbamoyl, C1-C4 alkylcarbamoyl, C2-C4alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4
  • Z 2 is C1-C6alkyl, wherein said C1-C6alkyl is unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C1-C4 alkoxy, phenyl, a 4, 5- or 6- membered saturated, partially unsaturated or aromatic heterocycle, or cyclopropyl, cyanocyclopropyl; wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from cyano, and wherein any of said 4-, 5- or 6- membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms selected from O, S or N, with the proviso that only one is O or S; and wherein any of said phenyl and 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle, are unsubstituted or substituted with 1, 2 or 3 substituents independently selected from halogen, C1-C4 haloalkyl, C1-C4alkyl
  • Z 2 is C1-C6alkyl, wherein said C1-C6alkyl is unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, or with one substituent selected from C1-C3 alkoxy, phenyl, a 4, 5- or 6- membered saturated, partially unsaturated or aromatic heterocycle, or cyclopropyl; wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from cyano; wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms selected from O, S or N, with the proviso that only one is O or S; and wherein any of said phenyl and 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycles, are unsubstituted or substituted with 1, or 2 substituents selected from halogen, cyano, C1-C3 haloalkyl, C1-C3alkyl
  • Z 2 is C1-C6alkyl, wherein said C1-C6alkyl is unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, or with one substituent selected from C1-C2 alkoxy, phenyl, a 4, 5- or 6- membered saturated, partially unsaturated or aromatic heterocycle, or cyclopropyl; wherein said cyclopropyl is unsubstituted or substituted with 1 substituent selected from cyano; wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms selected from O, S or N, with the proviso that only one is O or S; and wherein any of said phenyl and 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycles, are unsubstituted or substituted with 1, or 2 substituents selected from halogen, cyano, C1-C2 haloalkyl, C1-C2alky
  • Z 2 is C1-C6alkyl, wherein said C1-C6alkyl is unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, or with one substituent selected from methoxy, ethoxy, or cyclopropyl.
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 are independently selected from hydrogen, or C1-C4 alkyl, wherein said C1-C4 alkyl is unsubstituted or substituted with 1 substituent selected from cyano, halogen, or C1-C4 alkoxy.
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 are hydrogen. In another embodiment of the invention R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 are methyl.
  • the present invention accordingly, makes available a compound of formula (I) having R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , W 1 , W 2 , Z 1 and Z 2 as defined above in all combinations / each permutation.
  • Embodiments according to the invention are provided as set out below.
  • the compound of formula (I) may be a compound of formula (I-A), wherein W 1 is a bond wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , W 2 , Z 1 and Z 2 are as defined for the compounds of formula (I) according to the present invention.
  • Z 1 is a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle; wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms independently selected from O, S, or N, with the proviso that only one is O or S; and wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycles, are unsubstituted or substituted with 1 or 2 substituents independently selected from halogen, C1-C2 haloalkyl, C1-C2alkyl, C2-C3 alkenyl, C2-C3 alkyny
  • Z 1 is a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle; wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms 82953 FF 19 independently selected from O, S, or N, with the proviso that only one is O or S; and wherein any of said 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycles, are unsubstituted or substituted with 1 or 2 substituents independently selected from halogen, trifluoromethyl, difluoromethyl, methyl, vinyl, prop-1- enyl, ethyn
  • Z 1 is a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle selected from oxetan-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, 1H-pyrrol-1-yl, 1H-pyrrol-2-yl, 1-methylpyrrol-2-yl, 1H-pyrrol-3-yl, 1-methylpyrrol-3-yl, 1
  • Z 1 is a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle selected from oxetan-3-yl, tetrahydrofuran-3-yl, tetrahydropyran-4-yl, 1H-pyrazol-1-yl, 1-methylpyrazol-3-yl, 2-methylpyrazol-3-yl, 3H- pyrazol-3-yl, 1-methylpyrazol-4-yl, 3-isoxazolyl, 5-isoxazolyl, 2-thienyl, 3-thienyl, 1-methylimidazol-2-yl, 3- methylimida
  • Z 1 is a 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle selected from oxetan-3-yl, tetrahydropyran-4-yl, 1H-pyrazol-1-yl, 1-methylpyrazol-3-yl, 2-methylpyrazol-3-yl, 3H-pyrazol-3-yl, 1- methylpyrazol-4-yl, 3-isoxazolyl, 5-isoxazolyl, 2-thienyl, 3-thienyl, 1-methylimidazol-2-yl, 3-methylimidazol-4-yl, 1-methylimidazol-4
  • the present invention accordingly, makes available a compound of formula (I-A), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , W 2 and Z 2 are as defined for the compounds of formula (I) having Z 1 as defined above in all combinations / each permutation.
  • Embodiments according to the invention are provided as set out below.
  • R 1 is C1-C3 alkyl, or C3-C6cycloalkyl
  • R 2 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 alkoxy-C1-C2alkyl, C1-C2 alkoxy-C1-C2alkoxy, C1- C2alkoxy-C1-C2alkoxy-C1-C2alkyl, acetyl, or N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl
  • R 3 is hydrogen;
  • R 4 is halogen, or C1-C3 alkyl; and
  • R 5 is hydrogen; or R 4 is hydrogen; and R 5 is halogen or C1-C3 alkyl;
  • R 14 is hydrogen, or C 1 -C 4 alkyl, wherein said C 1 -C 4 alkyl is unsubstituted or substituted with
  • R 1 is C1-C3 alkyl, or C3-C6cycloalkyl
  • R 2 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 alkoxy-C1-C2alkyl, C1-C2 alkoxy-C1-C2alkoxy, C1- C2alkoxy-C1-C2alkoxy-C1-C2alkyl, acetyl, or N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl
  • R 3 is hydrogen;
  • R 4 is halogen, or C1-C3 alkyl; and R 5 is hydrogen; or R 4 is hydrogen; and R 5 is halogen or C1-C3 alkyl;
  • R 14 is hydrogen, or C1-C3 alkyl;
  • Z 1 is hydrogen, C1-C6alkyl, C2-C6alkeny
  • R 1 is C1-C3 alkyl, or C3-C6cycloalkyl
  • R 2 is hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C2 alkoxy-C1-C2alkyl, C1-C2 alkoxy-C1-C2alkoxy, C1- C2alkoxy-C1-C2alkoxy-C1-C2alkyl, acetyl, or N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl
  • R 3 is hydrogen
  • R 4 is halogen, or C1-C3 alkyl
  • R 5 is hydrogen
  • or R 4 is hydrogen
  • R 5 is halogen or C1-C3 alkyl
  • Z 1 is hydrogen, C1-C6alkyl, C2-C6alkenyl, or C2-C6alkynyl, wherein
  • the compound of formula (I) according to the invention is selected from compounds of formula (I), (I-A), (I-A1), (I-A2), or (I-A3),
  • the compound of formula (I) according to the invention is selected from compounds listed in any one of Tables A-1 to A-50. More preferably the compound of formula (I) according to the invention is selected from compounds listed in Table P (below).
  • compounds of formula (I) may be prepared from compounds of formula (III) or a salt thereof, wherein Z 2 is as defined above for compound of formula (I), and W 2 is NR 14 , by reaction with a compound of formula (II), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 5 , W 1 , and Z 1 , are as defined above for the compound of formula (I).This reaction is shown in Scheme 1.
  • compounds of formula (IIa), where X 0 is halogen are formed by treatment of compounds of formula (II) with, for example, oxalyl chloride or thionyl chloride in the presence of catalytic quantities of N,N-dimethylformamide (DMF) in inert solvents such as DCM or THF at temperatures between 20°C to 100°C, preferably 25°C.
  • DMF N,N-dimethylformamide
  • compounds of formula (I) may be prepared by treatment of compounds of formula (II) with dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 1- 82953 FF 39 [bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) to give the activated compound of formula (IIb), wherein G 0 is G 01 , G 02 or G 03 as set forth below, in an inert solvent, e.g., pyridine, DMF, acetonitrile, DCM or THF, optionally in the presence of a base, e.g., triethylamine, at temperatures between 30°C and 180°C.
  • DCC dicyclohexyl carbodiimide
  • EDC 1-ethyl-3-(3-di
  • a compound of formula (II) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P) to provide compounds of formula (IIa), wherein G 0 is G 04 as set forth in scheme 2, and as described for example in Synthesis 2013, 45, 1569. Further reaction with an amine (or a salt thereof) of the compound of formula (III) leads to compounds of formula (I).
  • Compounds of formula (II) can be prepared from compounds of formula (IIc), wherein R 1 , R 2 , R 3 , R 4 , R 5 , W 1 , and Z 1 are as described in formula (I), and R 01 is C1-C4alkyl, by ester hydrolysis (scheme 3).
  • boronic acid may also be in the form of a boronic ester such as (4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl).
  • reaction can be performed by interchanging the coupling partners, e.g., by reacting a compound of formula (X), wherein R 1 , R 2 and R 3 are as defined above for the compound of formula (I), with a compound of formula (IX), wherein, R 4 , R 5 , W 1 , and Z 1 are as defined above for the compound of formula (I) and X 03 is halogen, preferably chlorine, bromine or iodine, to provide a compounds of formula (VI).
  • R 1 , R 2 , R 3 , R 4 , R 5 , W 1 , and Z 1 are as defined above for the compound of formula (I) (Scheme 10).
  • compounds of formula (IX), wherein substituents are as previously defined and X 3 is halogen, preferably chlorine, bromine or iodine, are treated with compounds of formula (XII), wherein R 1 , R 2 and R 3 are as defined above for the compound of formula (I), in the presence of a palladium catalyst, typically palladium acetate Pd(OAc)2, a suitable ligand, for example 1,10-phenanthroline, in the presence of a base such as cesium carbonate or potassium carbonate, in inert solvents such as chlorobenzene, toluene or xylene at temperatures between room temperature and 180°C, optionally under microwave heating conditions, preferably under inert atmosphere.
  • a palladium catalyst typically palladium acetate Pd(OAc)2
  • a suitable ligand for example 1,10-phenanthroline
  • a base such as cesium carbonate or potassium carbonate
  • inert solvents such as chlorobenzene, toluen
  • the metal derivative can also be and organono zinc derivative (Negishi coupling), trialkyl tin derivative (Stille coupling), organo magnesium derivative (Kumada Coupling), or organosilicon derivative (Hiyama coupling), all in the presence of palladium or nickel catalysts.
  • organono zinc derivative Negishi coupling
  • trialkyl tin derivative Stille coupling
  • organo magnesium derivative Kumada Coupling
  • organosilicon derivative Hiyama coupling
  • Such reactions can be achieved by nucleophilic aromatic substitution (SnAr) reactions by treatment with compounds of formula Z 1 -OH, Z 1 -N(R 6 )H, OR Z 1 -SH, optionally in the presence of a base.
  • SnAr nucleophilic aromatic substitution
  • Such reactions are well known to those skilled in the art and are particularly facile when the carbon is activated by an adjacent nitrogen as is the case in compound (Ia).
  • Reactions of this type can also be carried out in the presence of metal catalysts, such as copper, optionally with ligands.
  • metal catalysts such as copper
  • compounds with more than one asymmetric carbon atoms may exist in diastereomeric forms which can be optionally separated using for example supercritical fluid chromatography (SFC) chromatography with chiral columns.
  • SFC supercritical fluid chromatography
  • Such diastereomers can show a different fungicidal activity profile, but all isomers and diastereomers form part of this invention.
  • the compounds of formula (I) and, where appropriate, the tautomers thereof, in each case in free form or in salt form can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • Diaporthe miriciae also known as Diaporthe ueckeri or Diaporthe ueckerae
  • Didymella spp. Drechslera spp.
  • Elsinoe spp. Elsinoe spp.
  • Erwinia amylovora Erysiphe spp. including E. cichoracearum
  • Eutypa lata Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F.
  • leucotricha Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp. including P. oryzae, Pythium spp. including P.
  • target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), millet, oats
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • useful plants is to be understood as also including useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate- synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • ALS inhibitors for example primisulfuron, prosulfuron and trifloxysulfuron
  • EPSPS (5-enol-pyrovyl-shikimate-3-phosphate- synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxida
  • crops is to be understood as including also crop plants which have been so transformed using recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as delta-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid- UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • delta-endotoxins for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A
  • Vip vegetative insecticidal proteins
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO02/15701).
  • Truncated toxins for example a truncated Cry1Ab, are known.
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a Cry1Ac toxin); Bollgard I® (cotton variety that express
  • transgenic crops are: 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St. Sauveur, France, registration number C/FR/96/05/10.
  • NK603 ⁇ MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B 1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp.
  • the compounds of formula (I) according to the invention may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi such as Alternaria species in fruits, vegetables and potatoes; Botrytis cinerea in strawberries, tomatoes, sunflower, pulse crops, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables; Uncinula necator in grapes; Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium in cucurbits; Leveillula taurica in cucurbits and solanaceous crops; Fusarium spp. in cereals; Leptosphaeria spp. in cereals; and Zymoseptoria spp. in cereals.
  • phytopathogenic diseases especially phytopathogenic fungi such as Alternaria species in fruits, vegetables and potatoes; Botrytis cinerea in strawberries, tomatoes, sunflower, pulse crops, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables; Uncin
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There can be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants.
  • Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil may also be mentioned. These young plants can be protected before transplantation by a total or partial treatment by immersion.
  • plant propagation material is understood to denote seeds.
  • the compounds of formula (I) according to the invention may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g., in polymeric substances.
  • Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids.
  • Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated.
  • the amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the 82953 FF 62 capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimeter to 1 centimeter and preferably 1 to 2 millimeters in diameter.
  • Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and granular carbon.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2- butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,
  • Water is generally the carrier of choice for the dilution of concentrates.
  • suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin. 82953 FF 63
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation.
  • Typical surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2 ethylhexyl) sulfosuccinate;
  • compositions of the invention include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants, and sticking agents.
  • biocidal active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention.
  • the compounds of formula (I) according to the invention are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants.
  • lecontei NPV, Orius spp. Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en- 1-yl acetate
  • Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • the mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
  • the mixtures comprising a compound selected from compounds of formula (I), (I-A), (I-A2), or (I-C), or compounds selected from compounds listed in Tables A-1 to A-50, or compounds listed in Table P (below), and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • compositions may be produced in conventional manner, e.g., by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers, and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners, and compounds that provide adjuvancy effects). Also, conventional slow-release formulations may be employed where long lasting efficacy is intended.
  • Table A-6 This table provides 34 compounds (A-6.01) to (A-6.34) of formula (I-A) wherein R 2 and R 4 are H, R 5 is CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 5,5-difluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-7 This table provides 34 compounds (A-7.01) to (A-7.34) of formula (I-A) wherein R 2 and R 4 are H, R 5 is CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 5,5,5-trifluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-9.33) has the following structure: Compound (A-9.33) 82953 FF 85 Table A-10: This table provides 34 compounds (A-10.01) to (A-10.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • Table A-11 This table provides 34 compounds (A-11.01) to (A-11.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 4-cyclopropyl-butyl, and Z 1 substituents are as defined in Table A.
  • compound A-11.04 has the following structure: Compound (A-11.04) (A-12.01) to (A-12.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 4,4-dimethyl-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-13 This table provides 34 compounds (A-13.01) to (A-13.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 2-cyclohexyl-ethyl, and Z 1 substituents are as defined in Table A.
  • Table A-14 This table provides 34 compounds (A-14.01) to (A-14.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NH-, Z 2 is 5,5-difluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-17 This table provides 34 compounds (A-17.01) to (A-17.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -N(CH3)-, Z 2 is n-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-17.23) has the following structure: Compound (A-17.23) compounds (A-18.01) to (A-18.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -N(CH3)-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • compound (A-20.05) has the following structure: Compound (A-20.05) (A-21.01) to (A-21.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NHO-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • Table A-22 This table provides 34 compounds (A-22.01) to (A-22.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -NHO-, Z 2 is 4-cyclopropyl-butyl, and Z 1 substituents are as defined in Table A.
  • Table A-23 This table provides 25 compounds (A-23.01) to (A-23.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -O-, Z 2 is n-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-23.17) has the following structure: Compound (A-23.17) compounds (A-24.01) to (A-24.34) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a bond, W 2 is -O-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • Table A-25 This table provides 25 compounds (A-25.01) to (A-25.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is n-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-25.12) has the following structure: 82953 FF 87 Compound (A-25.12) (A-26.01) to (A-26.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • Table A-27 This table provides 25 compounds (A-27.01) to (A-27.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-,Z 2 is 4-cyclopropyl-butyl, and Z 1 substituents are as defined in Table A.
  • Table A-28 This table provides 25 compounds (A-28.01) to (A-28.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is 4,4-dimethyl-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-29 This table provides 25 compounds (A-29.01) to (A-29.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is 5,5-difluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-30 This table provides 25 compounds (A-30.01) to (A-30.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is 5,5,5-trifluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-31 This table provides 25 compounds (A-31.01) to (A-31.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is O, W 2 is -NH-, Z 2 is 5-fluoro-pentyl, and Z 1 substituents are as defined in Table A.
  • Table A-32 This table provides 25 compounds (A-32.01) to (A-32.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is NH, W 2 is -NH-, Z 2 is n-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-38.06) has the following structure: Compound (A-38.06) (A-39.01) to (A-39.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is a S, W 2 is -NH-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • Table A-40 This table provides 25 compounds (A-40.01) to (A-40.25) of formula (I-A wherein R 4 is H, R 2 and R 5 are CH3, W 1 is S, W 2 is -NH-,Z 2 is 4-cyclopropyl-butyl, and Z 1 substituents are as defined in Table A.
  • Table A-41 This table provides 25 compounds (A-41.01) to (A-41.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is SO2, W 2 is -NH-, Z 2 is n-pentyl, and Z 1 substituents are as defined in Table A.
  • compound (A-41.15) has the following structure: 82953 FF 89 Compound (A-41.15) (A-42.01) to (A-42.25) of formula (I-A) wherein R 4 is H, R 2 and R 5 are CH3, W 1 is SO2, W 2 is -NH-, Z 2 is 3-cyclopropyl-propyl, and Z 1 substituents are as defined in Table A.
  • compound (A-50.01) has the following structure: Compound (A-50.01) EXAMPLES
  • the Examples which follow serve to illustrate the invention and are not meant in any way to limit the invention.
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 60 ppm, 20 ppm or 2 ppm.
  • LCMS Method B Spectra were recorded on a ACQUITY Mass Spectrometer from Waters Corporations (SQD Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, Desolvation Temperature: 400°C, Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/hr, Mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporations with solvent degasser, binary pump, heated column compartment and diode-array detector.
  • an electrospray source Polyity: positive or ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, Desolvation Temperature: 400°C, Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/hr, Mass range:
  • LCMS Method C Spectra were recorded on a Mass Spectrometer from Waters Corporation (SQD, SQDII or Single mass spectrometer) equipped with an electrospray source (Polarity: positive and , Capillary: 0.8-3.00 kV, Cone: 5-30 V, Source Temperature: 120-150°C, Desolvation Temperature: 350-600°C, Cone Gas Flow: 50-150 l/h, Desolvation Gas Flow: 650-1000 l/h, Mass range: 100 to 900 Da and an Acquity UPLC from Waters Corporation: Binary pump, heated column compartment, diode- array detector and ELSD.
  • Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether (7-8 mol of ethylene oxide) - 2 % - highly dispersed silicic acid 5 % 10 % 10 % Kaolin 62 % 27 % - The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % - Kaolin 65 % 40 % - Talcum - - 20 % The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide) 3 % calcium dodecylbenzene sulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 % Cyclohexanone 30 % xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Suspension concentrate active ingredients 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 % Water 32 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % Tristyrenephenole with 10-20 moles EO 2 % 1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 % Silicone oil (in the form of a 75 % emulsion in water) 0.2 % Water 45.3 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • the mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • Step 2 Preparation of 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-pyridine-2-carboxamide (compound P-5, Table P) 2-carboxamide (0.05 g, 184.40 ⁇ mol) 4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl) pyrazole (40.95 mg, 184.40 ⁇ mol) in dioxane (2 mL) and H2O (0.5 mL) was added K3PO4 (78.28 mg, 368.80 ⁇ mol) and Pd(dppf)Cl2 (13.49 mg, 18.44 ⁇ mol) under nitrogen atmosphere.
  • reaction mixture was allowed to warm to rt and stirred for 8 82953 FF 97 hrs upon which time LC-MS showed reaction completion.
  • Step 2 Preparation of methyl 6-chloro-5-methyl-pyridine-2-carboxylate 1-oxido-pyridin-1-ium-2-carboxylate (17g, 0.102mol) in chloroform (300mL) was treated with phosphorus oxychloride (140.4g, 0.916mol) and TEA (30.9g, 0.305mol) at rt under nitrogen. The reaction mixture was heated to 80°C until completion as monitored by LCMS. The phosphorus oxychloride was removed by distillation in vacuo, and the residue taken up in DCM (200 mL) and quenched with 2L of crushed ice.
  • Step3 Preparation of methyl 6-chloro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2- carboxylate were added cyclohexane ( 500 mL), methyl 6-chloro-5-methyl-pyridine-2- carboxylate (12.6 g, 0.07mol), 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine (1.89g, 0.007mol), Bis[(1,2,5,6- ⁇ )-1,5- cyclooctadiene]di- ⁇ -methoxydiiridium (0.887g, 0.0013mol) and Bis(pinacolato)diborane (34.4g, 0.135mol).
  • the reaction mixture was heated to 80°C and stirred for 12 hr monitored by GCMS.
  • the reaction mixture was concentrated in vacuo and the residue obtained was dissolved in 150mL of EtOAc.
  • the mixture was stirred with 15g of activated charcoal for 30 min for decolorization and filtered.
  • the resulting filtrate was concentrated in vacuo to obtain 46 g of black oil.
  • the oil was distilled using a pump at an external temperature of 160°C and an internal temperature of 8°C to remove most of the excess Bis(pinacolato)diborane.
  • the remaining mixture was cooled to 15°C, dissolved with 150mL of EtOAc and decolorized with 10g of activated charcoal.
  • the reaction mixture was heated to 65°C for 2hr.
  • the reaction mixture was cooled to 15°C and concentrated in vacuo to obtain 52g of brown solid.
  • the solid was then stirred with 30mL of MTBE and filtered to obtain the title compound.
  • the resulting reaction mixture was flushed with argon for 5 min and 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (49 mg, 0.0597 mmol) was added.
  • the reaction mixture was flushed with argon for 5 min and stirred at 75 °C for 16 hours.
  • the reaction mixture was allowed to cool down to rt and was partitioned between water (20 mL) and EtOAc (20 mL). The layers were separated, the aqueous layer was extracted with EtOAc (10 mL), and the combined organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.
  • Step 2 Preparation of methyl 5-amino-4-bromo-6-(1-methylpyrazol-4-yl)pyridine-2-carboxylate 82953 FF 103 4,6-dibromo-pyridine-2-carboxylate (0.1 g, 0.30 mmol), (1-methylpyrazol-4- yl)boronic acid (38.5 mg, 0.30 mmol) and potassium carbonate (84.7 mg, 0.61 mmol) in toluene/ethanol (1:1) (0.6 mL) was stirred under nitrogen at rt.
  • Step 3 Preparation of methyl 5-amino-4-(1,5-dimethylpyrazol-4-yl)-6-(1-methylpyrazol-4-yl)pyridine-2- carboxylate bromo-6-(1-methylpyrazol-4-yl)pyridine-2-carboxylate (0.46 g, 1.48 mmol) and 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (0.72 g 3.26 mmol) in 2-MeTHF (6 mL) was treated with potassium phosphate (1.27 g 5.92 mmol) at rt and the reaction mixture was de-gassed with nitrogen for 15 min.
  • Step 5 Preparation of 5-chloro-4-(1,5-dimethylpyrazol-4-yl)-6-(1-methylpyrazol-4-yl)-N-pentyl-pyridine-2- carboxamide (Compound P-71, Table P) A solution of 5-amino-4-(1,5-dimethylpyrazol-4-yl)-6-(1-methylpyrazol-4-yl)-N-pentyl-pyridine-2-carboxamide (0.070 g, 0.18 mmol) in hydrochloric acid (2.75 mL) was allowed to stir at 0 °C.
  • test compound After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 - 4 days after application.
  • DMSO DMSO
  • test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 - 4 days after application.
  • the following compounds gave at least 80% control of Fusarium culmorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-18, P-19, P-21, P-22, P-23, P-27, P-28, P-33, P-35, P-44, P-47, P-50, P-56, P-57, P-58, P-59, P-65, P-66, P-71, P-72, P-73, and P-74
  • Example B-6 Fusarium culmorum / wheat / (Head blight) 82953 FF 118 Wheat spikelets cv.
  • test compound After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 4 - 5 days after application.
  • DMSO DMSO
  • tritici / wheat / (Brown rust) leaf segments cv. Kanzler are placed on agar in plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates are stored in darkness at 19°C and 75% rh. The formulated test compound diluted in water is applied 1 day after inoculation. The leaf segments are incubated at 19°C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 - 8 days after application).
  • the leaf segments are inoculated with a spore suspension of the fungus 2 days after application.
  • the inoculated leaf segments are incubated at 20°C and 65% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application).
  • test compounds After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format), the nutrient broth containing the fungal material is added. The test plates are incubated at 24°C and the inhibition of growth is determined photometrically 3 - 4 days after application.
  • DMSO DMSO
  • a DMSO solution of the test compounds was a broth containing the fungal spores was added to it.
  • the test plates were incubated at 24 °C and the inhibition of growth was determined photometrically after 3 - 4 days at 620 nm.
  • the following compounds gave at least 80% control of Cercospora kikuchii at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-73, and P-74
  • Example B-19 Cercospora sojina (frogeye leaf spot of soybean):Conidia of the fungus from cryogenic storage broth).
  • a DMSO solution of the test compounds was a broth containing the fungal spores was added to it.
  • test plates were incubated at 24 °C and the inhibition of growth was determined photometrically after 3 - 4 days at 620 nm. 82953 FF 122
  • the following compounds gave at least 80% control of Corynespora cassiicola at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: P-73, and P-74
  • Example B-21 Gibberella zeae (Fusarium graminearum) / wheat / (Head blight) Wheat spikelets cv. Monsun are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • the spikelets are inoculated with a spore suspension of the fungus.
  • the inoculated test leaf disks are incubated at 20 °C and 60% rh under a light regime of 72 h semi darkness followed by 12 h light / 12 h darkness in a climate chamber, the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check spikelets (6 - 8 days after application).

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Abstract

L'invention concerne un composé de formule (I), les substituants étant tels que définis dans la revendication 1, et les sels, stéréoisomères, énantiomères, tautomères et N-oxydes agrochimiquement acceptables de ces composés, qui peuvent être utilisés en tant que fongicides.
PCT/EP2024/077866 2023-10-11 2024-10-03 Dérivés de pyridyl pyrazole microbiocides Pending WO2025078263A1 (fr)

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Citations (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0357460A2 (fr) 1988-09-02 1990-03-07 Sankyo Company Limited Dérivés de la milbémycine, leur préparation et leur utilisation
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0444964A1 (fr) 1990-03-01 1991-09-04 Sankyo Company Limited Dérivés d'éthers milbémycine, leur préparation et leur utilisation comme anthelmintiques
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
EP0594291A1 (fr) 1992-09-01 1994-04-27 Sankyo Company Limited Procédés pour la préparation de dérivés des milbémycines ayant un groupe d'éther sur la position 13
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
WO1998004557A1 (fr) 1996-07-30 1998-02-05 Bionumerik Pharmaceuticals, Inc. Nouveau procede de preparation de la camptothecine
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2004052370A2 (fr) 2002-12-11 2004-06-24 7Tm Pharma A/S Utilisation de composes de la quinoline pour traiter des troubles lies au recepteur mch
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
US6919298B2 (en) 2002-04-04 2005-07-19 Valent Biosciences Corporation Enhanced herbicide composition
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
US20150218102A1 (en) 2014-02-06 2015-08-06 Abbvie Inc. 6-heteroaryloxy- or 6-aryloxy-quinoline-2-carboxamides and method of use
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017029179A1 (fr) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Dérivés de triazole, leurs intermédiaires et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017207362A1 (fr) 2016-05-30 2017-12-07 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018177894A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2019105933A1 (fr) 2017-11-29 2019-06-06 Syngenta Participations Ag Dérivés de thiazole microbiocides
US20190337923A1 (en) * 2018-05-02 2019-11-07 Enanta Pharmaceuticals, Inc. Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2020056090A1 (fr) 2018-09-14 2020-03-19 Fmc Corporation Halométhyl cétones et hydrates fongicides
WO2020097012A1 (fr) 2018-11-06 2020-05-14 Fmc Corporation Tolyles substitués utilisés en tant que fongicides
WO2020102574A1 (fr) 2018-11-16 2020-05-22 Novartis Inflammasome Research, Inc. Composés et compositions pour le traitement d'états pathologiques associés à une activité de nlrp
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020109391A1 (fr) 2018-11-28 2020-06-04 Bayer Aktiengesellschaft Pyridazine (thio)amides servant de composés fongicides
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2020212513A1 (fr) 2019-04-18 2020-10-22 Syngenta Crop Protection Ag Procédé de préparation de dérivés d'oxadiazole microbiocides
WO2021244952A1 (fr) 2020-06-03 2021-12-09 Syngenta Crop Protection Ag Dérivés microbiocides
WO2022236319A1 (fr) 2021-05-07 2022-11-10 Enliven Therapeutics, Inc. Composés naphtyridone pour l'inhibition de kinases raf et/ou de tyrosine kinases bcr-abl
WO2023099460A1 (fr) * 2021-12-02 2023-06-08 Syngenta Crop Protection Ag Compositions fongicides

Patent Citations (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0357460A2 (fr) 1988-09-02 1990-03-07 Sankyo Company Limited Dérivés de la milbémycine, leur préparation et leur utilisation
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0444964A1 (fr) 1990-03-01 1991-09-04 Sankyo Company Limited Dérivés d'éthers milbémycine, leur préparation et leur utilisation comme anthelmintiques
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
EP0594291A1 (fr) 1992-09-01 1994-04-27 Sankyo Company Limited Procédés pour la préparation de dérivés des milbémycines ayant un groupe d'éther sur la position 13
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
WO1998004557A1 (fr) 1996-07-30 1998-02-05 Bionumerik Pharmaceuticals, Inc. Nouveau procede de preparation de la camptothecine
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US6919298B2 (en) 2002-04-04 2005-07-19 Valent Biosciences Corporation Enhanced herbicide composition
WO2004052370A2 (fr) 2002-12-11 2004-06-24 7Tm Pharma A/S Utilisation de composes de la quinoline pour traiter des troubles lies au recepteur mch
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
US20150218102A1 (en) 2014-02-06 2015-08-06 Abbvie Inc. 6-heteroaryloxy- or 6-aryloxy-quinoline-2-carboxamides and method of use
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017029179A1 (fr) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Dérivés de triazole, leurs intermédiaires et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017207362A1 (fr) 2016-05-30 2017-12-07 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018177894A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2019105933A1 (fr) 2017-11-29 2019-06-06 Syngenta Participations Ag Dérivés de thiazole microbiocides
US20190337923A1 (en) * 2018-05-02 2019-11-07 Enanta Pharmaceuticals, Inc. Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof
WO2020056090A1 (fr) 2018-09-14 2020-03-19 Fmc Corporation Halométhyl cétones et hydrates fongicides
WO2020097012A1 (fr) 2018-11-06 2020-05-14 Fmc Corporation Tolyles substitués utilisés en tant que fongicides
WO2020102574A1 (fr) 2018-11-16 2020-05-22 Novartis Inflammasome Research, Inc. Composés et compositions pour le traitement d'états pathologiques associés à une activité de nlrp
WO2020109391A1 (fr) 2018-11-28 2020-06-04 Bayer Aktiengesellschaft Pyridazine (thio)amides servant de composés fongicides
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2020212513A1 (fr) 2019-04-18 2020-10-22 Syngenta Crop Protection Ag Procédé de préparation de dérivés d'oxadiazole microbiocides
WO2021244952A1 (fr) 2020-06-03 2021-12-09 Syngenta Crop Protection Ag Dérivés microbiocides
WO2022236319A1 (fr) 2021-05-07 2022-11-10 Enliven Therapeutics, Inc. Composés naphtyridone pour l'inhibition de kinases raf et/ou de tyrosine kinases bcr-abl
WO2023099460A1 (fr) * 2021-12-02 2023-06-08 Syngenta Crop Protection Ag Compositions fongicides

Non-Patent Citations (32)

* Cited by examiner, † Cited by third party
Title
"The Pesticide Manual", 2009, BRITISH CROP PROTECTION COUNCIL
ADV. SYNTH. & CAT., vol. 362, no. 24, 2020, pages 5777 - 5782
CHEM. COMM., vol. 10, 2002, pages 1040 - 1041
CHEM. SCI., vol. 4, 2013, pages 2374 - 2379
CHEM., vol. 5, 2019, pages 526 - 552
HECK, CHEM. REV., vol. 100, no. 8, 2000, pages 3009 - 3066
HETEROCYCLES, vol. 87, no. 6, 2013, pages 1279 - 1287
HIYAMA COUPLING: "Further useful reactions for coupling of sp3-Grignard reagents to compounds of formula (la) have been reported using copper or iron catalysts", ORG. BIOMOL. CHEM., vol. 13, 2015, pages 4816 - 4827
J. AM. CHEM. SOC., vol. 124, no. 46, 2002, pages 13856 - 13863
J. AM. CHEM. SOC., vol. 125, 2003, pages 2890
J. FLUORINE CHEM., vol. 107, 2001, pages 31 - 34
J. ORG. CHEM., vol. 83, no. 12, 2018, pages 6589 - 6598
J. ORGANOMET. CHEM., vol. 576, no. 1-2, 1999, pages 147 - 168
KUMADA COUPLING, MOLECULES, vol. 27, no. 17, 2022, pages 5654
NEGISHI COUPLING, ACS CATAL., vol. 5, 2015, pages 5,3040 - 3053
no. 1256813-52-1
ORG. LETT., vol. 17, no. 2, 2015, pages 3236 - 3239
ORG. LETT., vol. 3, no. 23, 2001, pages 3761 - 3764
ORG. LETT., vol. 9, 2007, pages 4575 - 4578
ORG. PROC. RES. & DEV., vol. 26, no. 6, 2022, pages 1690 - 1750
ROSENMUND, K. W. AND STRUCK, E., BER., vol. 52, 1919, pages 1749
SANDMEYER, MOLECULAR DIVERSITY, vol. 26, 2022, pages 1837 - 1873
SONOGASHIRA, CHEM. REV., vol. 107, no. 3, 2007, pages 874 - 922
STILLE COUPLING, MONATSHEFTE FAR CHEMIE-CHEMICAL MONTHLY, vol. 143, 2012, pages 1575 - 1592
SUZUKI- MIYAURA COUPLING, ACS CATAL., vol. 6, 2016, pages 3,1540 - 1552
SYNTHESIS, no. 3, 2008, pages 474 - 478
TET. LET, vol. 29, 1988, pages 2665 - 2666
TETRAHEDRON LETT., 1977, pages 4171 - 4174
TETRAHEDRON LETT., 2006, pages 5767 - 5769
TETRAHEDRON LETT., vol. 55, no. 51, 2014, pages 7130 - 7132
TETRAHEDRON, vol. 61, no. 46, 2005, pages 10827 - 10852
VON BRAUN, J.MANZ, G., ANN., vol. 488, 1931, pages 111

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