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WO2019011929A1 - Dérivés d'oxadiazole microbiocides - Google Patents

Dérivés d'oxadiazole microbiocides Download PDF

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Publication number
WO2019011929A1
WO2019011929A1 PCT/EP2018/068694 EP2018068694W WO2019011929A1 WO 2019011929 A1 WO2019011929 A1 WO 2019011929A1 EP 2018068694 W EP2018068694 W EP 2018068694W WO 2019011929 A1 WO2019011929 A1 WO 2019011929A1
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Prior art keywords
4alkyl
2alkyl
methyl
ccn
alternative name
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PCT/EP2018/068694
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English (en)
Inventor
Thomas James HOFFMAN
Daniel Stierli
Thomas Pitterna
Ramya Rajan
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Syngenta Participations Ag
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Priority to BR112020000456-1A priority Critical patent/BR112020000456A2/pt
Publication of WO2019011929A1 publication Critical patent/WO2019011929A1/fr

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    • 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
    • C07D413/10—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 linked by a carbon chain containing aromatic rings
    • 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

Definitions

  • R 5 and R 6 are independently selected from hydrogen or methyl
  • R 7 represents -C(0)N(R 7a )(R 7b ), wherein:
  • R 7a is Ci salkyl, Ci-4haloalkyl, cyanoCi-4alkyl, hydroxyCi-4alkyl, Ci-2alkoxyCi-4alkyl, Ci- 2haloalkoxyCi-4alkyl, C3-salkenyl, C3-salkynyl, aminoCi-4alkyl, amino, N,N-diCi-2alkylamino, N-formyl-N- Ci-2alkylamino, N-Ci-2alkylcarbonyl-N-Ci-2alkylamino, pyrroldin-1-amino, piperdin-1-amino, morpholin- 4-amino, N-Ci-2alkylaminoCi-4alkyl, N,N-diCi-2alkylaminoCi-4alkyl, hydroxyl, Ci-4alkoxy, C3-4alkenyloxy, C3-4haloalkyloxy, C3-4alkynyloxy, cyclo
  • R 8 is hydrogen, methyl, methoxy, formyl or acyl
  • R 7c is C2-5alkyl, Ci-4haloalkyl, cyanoCi-4alkyl, hydroxyCi-4alkyl, Ci-2alkoxyC2-4alkyl, Ci- 2alkoxyCi-2alkoxyCi-4alkyl, Ci-2haloalkoxyCi-4alkyl, C3-salkenyl, C3-salkynyl, C3-4haloalkenyl, N-Ci- 3alkylaminoCi-4alkyl, N,N-di-Ci-3alkylaminoCi-4alkyl; or
  • R 7c is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, phenylCi-2alkyl, heterocyclyl or heterocyclylCi-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 , 2, or 3 ring members independently selected from the group consisting of O, S, N or S(0)2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano
  • R 7 represents -C(0)C(0)N(R 7d )(R 7e ), wherein R 7d is Ci salkyl, Ci-4haloalkyl, cyanoCi-4alkyl, hydroxyCi-4alkyl, Ci-3alkoxyC2-4alkyl, Ci-
  • R 7e is hydrogen, Ci-4alkyl, Ci-4fluoroalkyl, cyclopropyl, cyclopropylmethyl; or (iv) R 7 represents -C(0)C(0)OR 7f , wherein:
  • R 7f is hydrogen, d-salkyl, Ci-4haloalkyl, C3-salkenyl, C3-salkynyl, or
  • R 7f is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S, N, SO2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, wherein the heteroaryl moiety is a 5- or 6- membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S; or
  • a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms wherein a fungicidally effective amount of a compound of Formula (I), or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
  • a compound of Formula (I) or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
  • (I) as a fungicide as a fungicide.
  • the use may exclude methods for the treatment of the human or animal body by surgery or therapy.
  • cyano means a -CN group.
  • hydroxyl or "hydroxy” means an -OH group.
  • amino means an -NH2 group.
  • acyl means a -C(0)CH3 group.
  • formyl means a -C(0)H group.
  • Ci-salkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to five carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Ci-4alkyl, d salkyl and Ci-2alkyl are to be construed accordingly.
  • Examples of d-salkyl include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (isopropyl), n-butyl, and 1-dimethylethyl (i-butyl).
  • Ci- C2alkylene refers to the corresponding definition of Ci-2alkyl, except that such radical is attached to the rest of the molecule by two single bonds.
  • Ci-4alkoxy refers to a radical of the formula -OR a where R a is a Ci- 4alkyl radical as generally defined above.
  • the terms d salkoxy and Ci-2alkoxy are to be construed accordingly.
  • Examples of Ci-4alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, isopropoxy, and i-butoxy.
  • Ci-4haloalkyl refers to a Ci-4alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • Examples of Ci-4haloalkyl include, but are not limited to fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, and 3,3,3-trifluoropropyl.
  • Cs-salkenyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (Z)-configuration, having from three to five carbon atoms, which is attached to the rest of the molecule by a single bond.
  • Examples of C3-salkenyl include, but are not limited to, prop-1- enyl, allyl (prop-2-enyl), and but-1-enyl.
  • C3-4haloalkenyl refers to a C3-4alkenyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • C3-4alkenoxy refers to a radical of the formula -OR a where R a is a C3- 4alkenyl radical as generally defined above.
  • Cs-salkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from three to five carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Examples of C3-5alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl).
  • C3-4alkynoxy refers to a radical of the formula -OR a where R a is a C3- 4alkynyl radical as generally defined above.
  • C3-4alkynyloxyCi-4alkyl refers to a Ci-4alkyl radical as generally defined above substituted by a C3-4alkynyloxy group as defined above.
  • Ci-2alkoxyCi-4alkyl refers to radical of the formula Rb-0-R a - where Rb is a Ci-2alkyl radical as generally defined above, and R a is a Ci-4alkylene radical as generally defined above.
  • hydroxyCi-4alkyl refers to a Ci-4alkyl radical as generally defined above substituted by one or more hydroxy groups.
  • hydroxyCi-2alkyl should be construed accordingly.
  • cyanoCi-4alkyl refers to refers to a Ci-4alkyl radical as generally defined above substituted by one or more cyano groups.
  • Ci-4alkylcarbonyl refers to a radical of the formula -C(0)R a where R a is a Ci-4alkyl radical as generally defined above.
  • Ci-2alkoxyCi-2alkoxyCi-4alkyl refers to a radical of the formula R a ORbORc-, where Rb and R c are Ci-2alkylene radicals as generally defined above, and R a is a Ci-4alkyl radical as generally defined above.
  • N-Ci-4alkylamino refers to a radical of the formula R a NH- where R a is a Ci-4alkyl radical as generally defined above.
  • N,N-diCi-4alkylamino refers to a radical of the formula R a (R a )N- where R a is a Ci-4alkyl radical as generally defined above.
  • C3-4haloalkoxy refers to a C3-4alkoxy group as defined above substituted by one or more of the same or different halogen atoms.
  • C3-6cycloalkyl refers to a stable, monocyclic ring radical which is saturated or partially unsaturated and contains 3 to 6 carbon atoms. C3-scycloalkyl and Cscycloalkyl are to be construed accordingly. Examples of C3-6cycloalkyl include, but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclopenten-1-yl, cyclopenten-3-yl, and cyclohexen-3-yl.
  • C3-6cycloalkylCi-2alkyl refers to a C3-6cycloalkyl ring as defined above attached to the rest of the molecule by a Ci-2alkylene radical as defined above.
  • Examples of C3- 6cycloalkylCi-3alkyl include, but are not limited to cyclopropyl-methyl and cyclobutyl-ethyl.
  • phenylCi-2alkyl refers to a phenyl ring attached to the rest of the molecule by a Ci-2alkylene radical as defined above.
  • phenylCi-2alkyl include, but are not limited to, benzyl.
  • heteroaryl generally refers to a 5- or 6-membered monocyclic aromatic ring radical which comprises 1 , 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • the heteroaryl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heteroaryl include but are not limited to, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, pyridyl, and indolyl.
  • heterocyclyl or “heterocyclic” generally refers to a stable, saturated or partially saturated , 4- to 6-membered, non-aromatic monocyclic ring, which comprises 1 , 2 or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • the heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heterocyclyl examples include, but are not limited to, azetidinyl, oxetanyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolanyl, and morpholinyl.
  • azetidinyl oxetanyl
  • pyrrolidyl tetrahydrofuryl
  • tetrahydrothienyl tetrahydrothiopyranyl
  • piperidinyl piperazinyl
  • tetrahydropyranyl dioxolanyl
  • morpholinyl morpholinyl
  • Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for a compound of Formula (I).
  • Formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto- enol tautomerism) where present.
  • the present invention includes all possible tautomeric forms for a compound of Formula (I).
  • the compounds of Formula (I) according to the invention are in free form, in oxidized form as an N-oxide, in covalently hydrated form, or in salt form, e.g. , an agronomically usable or agrochemically acceptable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.
  • R , R 2 , R 3 , R 4 are independently selected from hydrogen or fluoro, wherein 0, 1 or 2 of R , R 2 , R 3 and R 4 are fluoro.
  • R , R 2 , R 3 and R 4 are hydrogen; R 2 , R 3 and R 4 are hydrogen and R is fluoro; R , R 2 and R 4 are hydrogen and R 3 is fluoro; R and R 2 are fluoro and R 3 and R 4 are hydrogen; R and R 3 are fluoro and R 2 and R 4 are hydrogen, or R and R 2 are hydrogen and R 3 and R 4 are fluoro.
  • R to R 4 are hydrogen, or R is fluoro and R 2 to R 4 are hydrogen.
  • R 5 and R 6 independently represent hydrogen or methyl.
  • R 5 and R 6 are both hydrogen, or R 5 is hydrogen and R 6 is methyl. More preferably, R 5 and R 6 are both hydrogen.
  • Z is selected from Z , Z 2 , or Z 3 :
  • Z is Z .
  • Z is Z 2 .
  • Z is Z 3 .
  • Z is Z or Z 3 .
  • R z is R 7 .
  • R 7 may be a group individually selected from (i), (ii), (iii), (iv), (v) or (vi) as defined according to the invention.
  • R 7 is represented by group (i).
  • R 7 is represented by group (ii).
  • R 7 is represented by group (iii).
  • R 7 is represented by group (iv).
  • R 7 is represented by group (v).
  • R 7 is represented by group (vi).
  • R 7 may represent -C(0)N(R 7a )(R 7b ), wherein:
  • R 7a is Ci salkyl, Ci-4haloalkyl, cyanoCi-4alkyl, hydroxyCi-4alkyl, Ci-2alkoxyCi-4alkyl, Ci- 2haloalkoxyCi-4alkyl, C3-salkenyl, C3-salkynyl, aminoCi-4alkyl, amino, N,N-diCi-2alkylamino, N-formyl-N- Ci-2alkylamino, N-Ci-2alkylcarbonyl-N-Ci-2alkylamino, pyrroldin-1-amino, piperdin-1-amino, morpholin- 4-amino, N-Ci-2alkylaminoCi-4alkyl, N,N-diCi-2alkylaminoCi-4alkyl, hydroxyl, Ci-4alkoxy, C3-4alkenyloxy, C3-4haloalkyloxy, C3-4alkynyloxy, cyclo
  • R 7a is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, phenylCi-2alkyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 , 2, or 3 ring members independently selected from the group consisting of O, S, N or S(0)2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 2, 3 or 4 heteroatoms individually selected from N, O and S,
  • R 7b is hydrogen, Ci-4alkyl, Ci-4haloalkyl or cyclopropyl, or
  • R 7a and R 7b together with the nitrogen atom to which they are bonded, form a 4- to 6-membered monocycle optionally containing an additional heteroatom or group selected from O, S, S(0)2, C(O) and NR 8 , or
  • R 7a and R 7b together with the nitrogen atom to which they are bonded, form a 5- to 8-membered spirobicyclic ring system optionally containing an additional heteroatom or group selected from O, C(O), and NR 8 , wherein R 8 is hydrogen, methyl, methoxy, formyl or acyl.
  • R 7a is Ci-4alkyl, Ci-2fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, Ci-2alkoxyCi-2alkyl, Ci-2fluoroalkoxyCi-2alkyl, C3-4alkenyl, C3-4alkynyl, aminoCi-2alkyl, amino, N,N-diCi-2alkylamino, N- formyl-N-Ci-2alkylamino, N-Ci-2alkylcarbonyl-N-Ci-2alkylamino, pyrroldin-1 -amino, piperdin-1 -amino, morpholin-4-amino, N-Ci-2alkylaminoCi-2alkyl, N,N-diCi-2alkylaminoCi-2alkyl, hydroxyl, Ci-2alkoxy, C3- 4alkenyloxy, C3-4haloalkyloxy, C3-4alkyn
  • R 7a is Ci-4alkyl, Ci-2fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, Ci-2alkoxyCi-2alkyl, Ci-2fluoroalkoxyCi-2alkyl, C3- 4alkenyl, C3-4alkynyl, aminoCi-2alkyl, amino, hydroxyl, Ci-2alkoxy, C3-4alkenyloxy, C3-4haloalkyloxy, C3- 4alkynyloxy.
  • R 7a is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, phenylCi-2alkyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyi, phenyl, heterocyclyl, or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, amino, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy,
  • R 7b is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. More preferably, R 7b is hydrogen or methyl.
  • R 7 may represent -C(0)OR 7c , wherein:
  • R 7c is C2-5alkyl, Ci-4haloalkyl, cyanoCi-4alkyl, hydroxyCi-4alkyl, Ci-2alkoxyC2-4alkyl, Ci- 2alkoxyCi-2alkoxyCi-4alkyl, Ci-2haloalkoxyCi-4alkyl, C3-salkenyl, C3-salkynyl, C3-4haloalkenyl, N-C1- 3alkylaminoCi-4alkyl, N,N-di-Ci-3alkylaminoCi-4alkyl; or
  • R 7c is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, phenylCi-2alkyl, heterocyclyl or heterocyclylCi-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 , 2, or 3 ring members independently selected from the group consisting of O, S, N or S(0)2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S,
  • R 7c is C2-salkyl, Ci-4fluoroalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, Ci-2alkoxyC2alkyl,
  • R 7c is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, phenylCi-2alkyl, heterocyclyl or heterocyclylCi-2alkyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl or heteroarylCi-2alkyl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen
  • R 7d is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 , 2, or 3 ring members independently selected from the group consisting of O, S, N, SO2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, wherein the heteroaryl moiety is a 5- or 6- membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or
  • R 7e is hydrogen, Ci-4alkyl, Ci-4fluoroalkyl, cyclopropyl, cyclopropylmethyl.
  • R 7d is Ci-4alkyl, Ci-2fluorooalkyl, cyanoCi-2alkyl, hydroxyCi-2alkyl, Ci-2alkoxyC2alkyl, Ci-2haloalkoxyCi-2alkyl, C3-4alkenyl, C3-4alkynyl, hydroxyl, aminoCi-2alkyl, N-Ci-2alkylaminoCi-2alkyl, Ci- 4alkoxy, C3-4haloalkyloxy, C3-4alkenyloxy, C3-4alkynyloxy.
  • R 7d is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S or N, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, wherein the cycloalkyl, phenyl, heterocyclyl or heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from hydroxyl, formyl, acyl, cyano, halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy, or the
  • R 7e is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl or cyclopropyl. More preferably, R 7e is hydrogen or methyl.
  • R 7 may represent -C(0)C(0)OR 7f , wherein:
  • R 7f is hydrogen, d-salkyl, Ci-4haloalkyl, C3-salkenyl, C3-salkynyl, or
  • R 7f is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, heterocyclyl, wherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S, N, SO2, with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, wherein the heteroaryl moiety is a 5- or 6- membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S.
  • R 7f is hydrogen, methyl, ethyl, difluoromethyl, trifluoromethyl, C3-4alkenyl or C3- 4alkynyl.
  • R 7f is C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl, phenyl, heterocyclyl, wherein the heterocyclyl moiety is a 5- to 6-membered non-aromatic ring which comprises 1 or 2 ring members independently selected from the group consisting of O, S or N with the proviso that the heterocycle cannot contain 2 contiguous atoms selected from O and S, or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S.
  • R 7 may represent -C(0)C(0)R 7g , wherein R 7g is hydrogen, d-salkyl, or cyclopropyl.
  • R 7g is hydrogen, methyl, ethyl, n-propyl, or cyclopropyl.
  • the compound according to Formula (I) is selected from a compound 1.1 to 1.10 described in Table T1 (below), or a compound 2.1 to 2.80 described in Table T2 (below).
  • the compounds of the present invention may be enantiomers of the compound of Formula (I) as represented b a Formula (la) or a Formula (lb), wherein R 5 and R 6 are different substituents.
  • R ⁇ R 2 , R 3 , R 4 , R 5 , R 6 , Z (including Z ⁇ Z 2 , Z 3 ), R Z (R 7 , including as defined by R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g ) and R 8 with reference to the compounds of formula (I) of the present invention apply generally to the compounds of Formula (l-la), Formula (l-lla), Formula (l-lb), and Formula (l-llb), as do the specific disclosures of combinations of R , R 2 , R 3 , R 4 , R 5 , R 6 , Z (including Z ⁇ Z 2 , Z 3 ), R Z (R 7 , including as defined by R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7 a) and R 8 as represented in the compounds of Tables 1.1 A to 1.8A, Tables 1.1 B to 1.8B
  • Compounds of formula (I) can be prepared from compounds of formula (II), wherein X is a halogen, preferably CI, Br or I, via treatment with compounds of formula (III), in the presence of a base (e.g. K2CO3, CS2CO3, or NaH) in a suitable solvent (e.g. dimethylformamide or tetrahydrofuran) at a temperature between 25°C and 1 10°C.
  • a catalyst eg, Nal or 4-dimethylaminopyridine
  • This reaction is shown in Scheme 1.
  • compounds of formula (I) can be prepared from compounds of formula (IV) by treatment with trifluoroacetic fluoride, trifluoroacetic chloride, trifluoroacetic anhydride optionally in the presence of a base (eg, pyridine or 4-dimethylaminopyridine) in a suitable solvent, such as tetrahydrofuran or ethanol, at a temperature between 25°C and 75°C.
  • a base eg, pyridine or 4-dimethylaminopyridine
  • suitable solvent such as tetrahydrofuran or ethanol
  • Compounds of formula (IV) can be prepared from compounds of formula (V) by treatment with a hydroxylamine hydrochloride salt in the presence of a base, such as triethylamine, in a suitable solvent, such as methanol, at a temperature between 0°C and 100°C.
  • a base such as triethylamine
  • a suitable solvent such as methanol
  • Compounds of formula (II), wherein X is CI or Br can be prepared from compounds of formula (VIII) by treatment with a halogen source (eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) and a radical initiator (eg, (PhC02)2 or azobisisobutyronitrile (AIBN)) in a suitable solvent, such as tetrachloromethane, at temperatures between 55° and 100°C in the presence of ultraviolet light.
  • a halogen source eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)
  • a radical initiator eg, (PhC02)2 or azobisisobutyronitrile (AIBN)
  • suitable solvent such as tetrachloromethane
  • Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 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 Cry1 Ab toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10.
  • the compounds of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • transgenic soybean plants expressing toxins for example insecticidal proteins such as delta-endotoxins, e.g. Cry1 Ac (Cry1 Ac Bt protein).
  • toxins for example insecticidal proteins such as delta-endotoxins, e.g. Cry1 Ac (Cry1 Ac Bt protein).
  • this may include transgenic soybean plants comprising event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (eg, see paragraph [008] reference to Intacta RR2 PROTM soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191 ) or event DAS- 81419 (U.S. Patent No. 8632978 and related applications and patents).
  • event MON87701 see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (eg, see paragraph [008] reference to In
  • the compounds of Formula (I) (including any one of compounds 1.1 to 1 .10 described in Table T1 (below) or compounds 2.1 to 2.80 described in Table T2 (below)) or fungicidal compositions according to the present invention comprising a compound of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • 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.
  • 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.
  • vegetative material such as cuttings or tubers, for example potatoes.
  • seeds in the strict sense
  • roots in the strict sense
  • fruits in the tubers
  • bulbs rhizomes
  • parts of plants 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.
  • 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.
  • Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.
  • 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, ⁇ , ⁇ -dimethyl formamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glyco
  • 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. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes.
  • Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.
  • alcohol-alkylene oxide addition products such as tridecyl alcohol-C.sub. 16 ethoxylate
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
  • dialkyi esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • salts of mono and dialkyl phosphate esters such as mono and dialkyl phosphate esters.
  • adjuvants commonly utilized in agricultural compositions 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.
  • biocidally 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. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • the compounds of Formula (I) 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.
  • further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non- selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound Formula (I) an agriculturally acceptable carrier and optionally an adjuvant.
  • An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use.
  • Agricultural carriers are well known in the art.
  • said composition may comprise at least one or more pesticidally-active compounds, for example an additional fungicidal active ingredient in addition to the compound of Formula (I).
  • Suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fung
  • Suitable additional active ingredients also include the following: 3-difluoromethyl-
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173, and EP 0 503 538.
  • the compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.
  • 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.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis-2,2- dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate,
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • Other biological agents enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, thiabendazole.
  • the following mixtures of the compounds of formula (I) with active ingredients are preferred.
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of 1 , 1-bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1-naphthylacetamide (lUPAC name) (1295) + TX, 4-chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amid
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
  • an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
  • an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1 /- -pyridine-2- thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) +
  • a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name) (542) and methyl bromide (537) + TX,
  • an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane
  • a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913)
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2- dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3- dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4- dichlorotetrahydrothiophene 1 , 1-dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4- chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3- ylacetic acid (lUPAC name) (1286)
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, co
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
  • an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
  • a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
  • 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 as represented in Tables 1.1 A to 1.8A, Tables 1.1 B to 1.8B, Tables 2.1 A to 2.3A, Tables 2.1 B to 2.3B (below), or a compound 1.1 to 1.10 described in Table T1 (below) or a compound 2.1 to 2.80 described in Table T2 (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 can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides
  • Another aspect of the invention is related to the use of a compound of Formula (I) or of a preferred individual compound as defined herein, of a composition comprising at least one compound of Formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of Formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • a further aspect of the invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of Formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms
  • a compound of Formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts
  • Controlling or preventing means reducing infestation by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of Formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds of Formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid Formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of Formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation e.g. a composition containing the compound of Formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of Formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1 kg a.i./ha, most preferably from 20g to 600g a.i./ha.
  • convenient dosages are from 10mg to 1g of active substance per kg of seeds.
  • a composition comprising a compound of Formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.
  • compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK
  • 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).
  • appropriate formulation inerts diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly Formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of Formula (I) optionally together with other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • Table 1.1 A This table discloses 75 specific compounds of the formula (T-1 A):
  • R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, and R 9 -Nu is as defined below in Table 1A.
  • Tables 1.2A to 1.8A make available 75 individual compounds of the formula (T-1A) in which R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are as specifically defined in Tables 1.2A to 1.8A, which refer to Table 1 A wherein R 9 -Nu is specifically defined.
  • Table 1A
  • Table 1 .2A This table discloses 75 specific compounds of formula (T-1A) wherein R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R is fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1 .3A This table discloses 75 specific compounds of formula (T-1A) wherein R , R 2 , R 4 , R 5 , and R 6 are hydrogen, R 3 is fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1.4A This table discloses 75 specific compounds of formula (T-1A) wherein R 2 , R 4 , R 5 , and R 6 are hydrogen, R and R 3 are fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1.5A This table discloses 75 specific compounds of formula (T-1A) wherein R 3 , R 4 , R 5 , and R 6 are hydrogen, R and R 2 are fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1.6A This table discloses 75 specific compounds of formula (T-2A) wherein R , R 2 , R 3 R 4 , and R 5 are hydrogen, R 6 is methyl, and R 9 -Nu is as defined above in Table 1 A.
  • Table 1.7A This table discloses 75 specific compounds of formula (T-1A) wherein R ⁇ R 2 , R 5 and R' are hydrogen, R 3 and R 4 are fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1.8A This table discloses 75 specific compounds of formula (T-1A) wherein R 2 , R 3 , R 5 and R' are hydrogen, R and R 4 are fluorine, and R 9 -Nu is as defined above in Table 1A.
  • Table 1.1B This table discloses 75 s ecific compounds of the formula (T-1B):
  • R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, and R 9 -Nu is as defined below in Table 1B.
  • Tables 1.2B to 1.8B make available 75 individual compounds of the formula (T-1B) in which R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are as specifically defined in Tables 1.2B to 1.8B, which refer to Table 1 B wherein R 9 -Nu is specifically defined.
  • Table 1.2B This table discloses 75 specific compounds of formula (T-1B) wherein R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R is fluorine, and R 9 -Nu is as defined above in Table 1B.
  • Table 1.3B This table discloses 75 specific compounds of formula (T-1B) wherein, R , R 2 , R 4 , R 5 , and R 6 are hydrogen, R 3 is fluorine, and R 9 -Nu is as defined above in Table 1B.
  • Table 1.4B This table discloses 75 specific compounds of formula (T-1B) wherein R 2 , R 4 , R 5 , and R' are hydrogen, R and R 3 are fluorine, and R 9 -Nu is as defined above in Table 1B.
  • Table 1.5B This table discloses 75 specific compounds of formula (T-1 B) wherein R 3 , R 4 , R 5 , and R 6 are hydrogen, R and R 2 are fluorine, and R 9 -Nu is as defined above in Table 1 B.
  • Table 1.6B This table discloses 75 specific compounds of formula (T-1 B) wherein R , R 2 , R 3 R 4 , and R 5 are hydrogen, R 6 is methyl, and R 9 -Nu is as defined above in Table 1 B.
  • Table 1.7B This table discloses 75 specific compounds of formula (T-1 B) wherein R , R 2 , R 5 and R 6 are hydrogen, R 3 and R 4 are fluorine, and R 9 -Nu is as defined above in Table 1 B.
  • Table 1.8B This table discloses 75 specific compounds of formula (T-1 B) wherein R 2 , R 3 , R 5 and R 6 are hydrogen, R and R 4 are fluorine, and R 9 -Nu is as defined above in Table 1 B.
  • R , R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, and R 0 is as defined below in Table 2A.
  • Tables 2.2A to 2.3A make available 6 individual compounds of the formula (T-2A) in which R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are as specifically defined in Tables 2.2A to 2.3A, which refer to Table 2A wherein R 0 is specifically defined.
  • Table 2.2A This table discloses 6 specific compounds of formula (T-2A) wherein R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R is fluorine, and R 0 is as defined above in Table 2A.
  • Table 2.3A This table discloses 6 specific compounds of formula (T-2A) wherein, R , R 2 , R 4 , R 5 , and R 6 are hydrogen, R 3 is fluorine, and R 0 is as defined above in Table 2A.
  • Table 2.1 B This table discloses 6 specific compounds of the formula (T-2B):
  • R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, and R 0 -Nu is as defined below in Table 2B.
  • Tables 2.2B to 2.3B make available 6 individual compounds of the formula (T-2B) in which R ⁇ R 2 , R 3 , R 4 , R 5 , and R 6 are as specifically defined in Tables 2.2B to 2.3B, which refer to Table 2B wherein R 0 is specifically defined.
  • Table 2B
  • Table 2.2B This table discloses 6 specific compounds of formula (T-2B) wherein R 2 , R 3 , R 4 , R 5 , and R 6 are hydrogen, R is fluorine, and R 0 is as defined above in Table 2B.
  • Table 2.3B This table discloses 6 specific compounds of formula (T-2B) wherein, R , R 2 , R 4 , R 5 , and R 6 are hydrogen, R 3 is fluorine, and R 0 is as defined above in Table 2B.
  • 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 the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.
  • Compounds of Formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • temperatures are given in degrees Celsius (°C) and "mp.” means melting point.
  • LC/MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method (Methods A, B, C and D) is as follows: The description of the LC/MS apparatus and the method A is:
  • Type of column Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C.
  • Type of column Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C.
  • Type of column Waters ACQUITY UPLC BEH C18; Column length: 50 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.7 micron; Temperature: 35°C.
  • Nebulizer Gas (psi) 45
  • PDA Wavelength range 210 to 400 nm; Column : KINETEX EVO C18; Column length: 50 mm; Internal diameter of column : 4.6 mm; Particle Size: 2.6 micron; Temperature: 40°C.
  • enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.
  • Active ingredient [compound of Formula (I)] 25 % 50 % 75 %
  • the active ingredient 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 ingredient [compound of Formula (I)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 %
  • the active ingredient 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.
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Active ingredient [compound of Formula (I)] 5 % 6 % 4 %
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • the active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • polyethylene glycol (mol. wt. 200) 3 %
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. Suspension concentrate
  • Active ingredient [compound of Formula (I)] 40 %
  • nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • Silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Active ingredient [compound of Formula (I)] 40 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of a combination of the compound of Formula I are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1 ).
  • This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved.
  • a mixture of 2.8 parts 1 ,6- diaminohexane in 5.3 parts of water is added. 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.
  • AIBN azobisisobutyronitrile
  • BOP-CI phosphoric acid bis(2-oxooxazolidide) chloride
  • DIBAL-H diisobutyl aluminum hydride
  • DIPEA N,N-di-isopropylethylamine
  • NBS N-bromosuccinimide
  • LC/MS Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)
  • Example 1 This example illustrates the preparation of N-(2,2-difluoroethoxy)-1-[1-[[4-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]imidazol-4-yl]methanimine (compound 1.4 in Table T1 )
  • Step 2 Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3a Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3b Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole from 3-[4- (dibromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Example 2 This example illustrates the preparation of propyl 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]imidazole-4-carboxylate (compound 1.9 in Table T1 )
  • Step 1 Preparation of 1-[[4-[5-(trifluoromethvn-1 ,2,4-oxadiazol-3-yllphenyllmethyllimidazole-4- carboxylate
  • Step 2 Preparation of 1-[[4-[5-(trifluoromethvQ-1 ,2,4-oxadiazol-3 ⁇
  • Step 3 Preparation of propyl 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yllphenyllmethyllimidazole-4- carboxylate
  • reaction vessel was diluted with ice water (10 mL), extracted with ethyl acetate, brine solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure and afforded 0.075 g of the title compound as a light brown solid, mp.: 248 - 250 °C.
  • Example 3 This example illustrates the preparation of N-cyclopropyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl] phenyl] methyl]imidazole-4-carboxamide (compound 1.10 in Table T1 )
  • Table T1 Melting point (mp) data and/or retention times (T.R) for compounds 1.1 to 1.10 according to
  • Table T2 Melting point (mp) data and/or retention times HR) for compounds 2.1 to 2.80 according to
  • Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse.
  • the cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar.
  • the leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation.
  • Compounds to be tested are prepared as DMSO solutions (max. 10 mg/ml) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying.
  • the inoculated leaf disks or segments are incubated under defined conditions (temperature, relative humidity, light, etc.) according to the respective test system.
  • a single evaluation of disease level is carried out 3 to 14 days after inoculation, depending on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.
  • Example 1 Fungicidal activity against Puccinia recondita f. sp. tritici I wheat / leaf disc preventative (Brown rust)
  • Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • the leaf disks were inoculated with a spore suspension of the fungus 1 day after application.
  • the inoculated leaf segments were incubated at 19 C and 75% relative humidity (rh) under a light regime of 12 hours light / 12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 to 9 days after application).
  • the following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are then inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19°C and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12 hours light / 12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 to 8 days after application). The following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • leaf discs are inoculated by spraying a spore suspension on the lower leaf surface.
  • 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 disks (12 to 14 days after application).
  • the following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Example 4 Fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liguid culture / cucumber / preventative (Anthracnose) Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB - potato dextrose broth). 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 measured photometrically 3 to 4 days after application.
  • DMSO DMSO
  • the following compounds at 20 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control under the same conditions, which show extensive disease development.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne des composés représentés par la formule (I), dans laquelle les substituants sont tels que définis dans la revendication 1. Ces composés sont utiles en tant que pesticides, en particulier en tant que fongicides.
PCT/EP2018/068694 2017-07-11 2018-07-10 Dérivés d'oxadiazole microbiocides WO2019011929A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020016180A1 (fr) * 2018-07-16 2020-01-23 Syngenta Crop Protection Ag Dérivés d'oxadiazole microbiocides
WO2021033133A1 (fr) 2019-08-19 2021-02-25 Pi Industries Ltd. Nouveaux composés d'oxadiazole contenant un cycle hétéroaromatique à 5 chaînons pour la lutte ou la prévention contre des champignons phytopathogènes

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