WO2017085100A1 - Substituted oxadiazoles for combating phytopathogenic fungi - Google Patents

Substituted oxadiazoles for combating phytopathogenic fungi Download PDF

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Publication number
WO2017085100A1
WO2017085100A1 PCT/EP2016/077819 EP2016077819W WO2017085100A1 WO 2017085100 A1 WO2017085100 A1 WO 2017085100A1 EP 2016077819 W EP2016077819 W EP 2016077819W WO 2017085100 A1 WO2017085100 A1 WO 2017085100A1
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Prior art keywords
phenyl
alkyl
methyl
compounds
heterocycle
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PCT/EP2016/077819
Other languages
French (fr)
Inventor
Manuel KRETSCHMER
Christine WIEBE
Wassilios Grammenos
Ana Escribano Cuesta
Maria Angelica QUINTERO PALOMAR
Ian Robert CRAIG
Marcus Fehr
Tobias MENTZEL
Bernd Mueller
Christian Winter
Violeta TERTERYAN-SEISER
Jan Klaas Lohmann
Erica CAMBEIS
Thomas Grote
Original Assignee
Basf Se
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Publication date
Priority to US15/777,470 priority Critical patent/US10674727B2/en
Priority to EA201891146A priority patent/EA201891146A1/en
Priority to KR1020187017291A priority patent/KR20180083419A/en
Priority to CA3003949A priority patent/CA3003949A1/en
Priority to MX2018006244A priority patent/MX2018006244A/en
Priority to CN201680067179.XA priority patent/CN108289449A/en
Priority to JP2018525682A priority patent/JP2018537457A/en
Priority to EP16797869.1A priority patent/EP3376868A1/en
Application filed by Basf Se filed Critical Basf Se
Priority to BR112018008449-2A priority patent/BR112018008449B1/en
Priority to AU2016354902A priority patent/AU2016354902A1/en
Publication of WO2017085100A1 publication Critical patent/WO2017085100A1/en
Priority to IL259152A priority patent/IL259152A/en
Priority to CONC2018/0005384A priority patent/CO2018005384A2/en
Priority to ZA2018/03948A priority patent/ZA201803948B/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06—Coating or dressing seed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G7/00—Botany in general
    • A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

  • the present invention relates to the use oxadiazoles of the formula I, or an N-oxide and/or their agriculturally useful for controlling phytopathogenic fungi, or to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; the present invention also relates to mixtures comprising at least one such compound of the formula I and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one such compound of the formula I and to agrochemical compositions further comprising seeds.
  • EP 276432 A2 relates to 3-phenyl-5-trifluoromethyloxadiazole derivatives and to their use to combat phytopathogenic microorganisms.
  • WO 2013/008162 describes trifluoromethyl- oxadiazole derivatives with HDAC4 inhibitory activity and their medical use, particularly in the treatment of Huntington's disease, muscle atrophy and diabetes/metabolic syndrome.
  • WO1 1088192, WO 201 1088181 describes the medicinal use of trifluoromethyl-oxadiazole derivatives.
  • a use for controlling phytopathogenic fungi is not described.
  • WO 2015/185485 was published after the date of filing of the present application and describes the use of certain substituted oxadiazoles for combating phytopathogenic fungi
  • the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an objective of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. This objective is achieved by the oxadiazoles of the formula I and/or their agriculturally useful salts for controlling phytopathogenic fungi.
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio,
  • R 3 is H, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl
  • R 4 is H, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl
  • Agriculturally acceptable salts of the compounds of the formula I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C 4 -alkyl substituents and/or one phenyl or benzyl substituent, preferably
  • Anions of acceptable acid addition salts are primarily chloride, bromide, fluoride,
  • Ci-C 4 -alkanoic acids preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Stereoisomers of the formula I can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They also form part of the subject matter of the present invention.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • moieties having no brackets in the name are bonded via the last moiety e.g. C 2 -C6- alkenyloxyimino-Ci-C4-alkyl is bonded via Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl is bonded via
  • Ci-C4-alkyl etc.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl.
  • CrC6-haloalkyl refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl,
  • Ci-C6-alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as defined above) which is bonded via an oxygen, at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2- methylpropoxy or 1 ,1-dimethylethoxy.
  • Ci-C6-haloalkoxy refers to a Ci-C6-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCIs, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-di
  • phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl refer to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a phenyl or hetereoaryl radical respectively.
  • CrC4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above).
  • Ci-C4-alkoxy group refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkylthio group.
  • Ci-Ce-alkylthio refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term “CrC6-haloalkylthio” as used herein refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyi group.
  • hydroxyCi-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a OH group.
  • aminoCi-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a NH 2 group.
  • Ci-C4-alkylamino-Ci-C4-alkyl refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkyl-NH- group which is bound through the nitrogen.
  • diCi-C4-alkylamino-Ci-C4-alkyl refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a (Ci-C4-alkyl)2N- group which is bound through the nitrogen.
  • C2-C6-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2- propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-
  • C 2 -C6-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, 1-propynyl,
  • Cs-Cs-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • Cs-Cs-cycloalkyloxy refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via an oxygen.
  • aliphatic refers to compounds or radicals composed of carbon and hydrogen and which are non-aromatic compounds.
  • An alicyclic compound or radical is an organic compound that is both aliphatic and cyclic. They contain one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character.
  • cyclic moiety or "cyclic group'Yefer to a radical which is an alicyclic ring or an aromatic ring, such as, for example, phenyl or heteroaryl.
  • R 1a refers to aliphatic groups, cyclic groups and groups, which contain an aliphatic and a cyclic moiety in one group, such as in, for example, phenyl-Ci-C4-alkyl; therefore a group which contains an aliphatic and a cyclic moiety both of these moieties may be substituted or unsubstituted independently of each other.
  • heteroaryl refers to aromatic monocyclic or polycyclic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S.
  • phenyl refers to an aromatic ring systems incuding six carbon atoms (commonly referred to as benzene ring). In association with the group A the term “phenyl” is to be interpreted as a benzene ring or phenylene ring, which is attached to both, the oxadiazole moiety and the -CR 3 R 4 - group.
  • saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered carbocycle is to be understood as meaning both saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members.
  • Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.
  • 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms
  • ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms
  • a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine;
  • a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydro- furanyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,
  • hexahydroazepinyl such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6- tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or- 4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,
  • the term "5- or 6-membered heteroaryl” or the term “5- or 6-membered aromatic heterocycle” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, iso
  • a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
  • the embodiments of the intermediates correspond to the
  • A is phenyl which is unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A as defined or preferably defined herein and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the phenyl ring in para-pos ⁇ t ⁇ on with regard to the
  • A is phenyl which is unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A as defined or preferably defined herein and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the phenyl ring in / ⁇ e/a-position with regard to the
  • A is phenyl which is substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein and wherein the group -C(R 3 R 4 )-NR 1 R 2 is attached to the phenyl ring in para-pos ⁇ t ⁇ on with regard to the trifluoromethyloxadiazole group.
  • A is phenyl which is unsubstituted and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the phenyl ring in para-pos ⁇ t ⁇ on with regard to the
  • A is phenyl substituted by R A selected from halogen, or Ci-C6-alkyl. In a further preferred embodiment of the invention A is phenyl substituted by halogen. In a special preferred embodiment of the invention A is phenyl substituted by F. In a further special preferred embodiment of the invention A is phenyl substituted by CI.
  • A is phenyl substituted by Ci-C6-alkyl. In a special preferred embodiment of the invention A is phenyl substituted by CH3. In a further special preferred embodiment of the invention A is phenyl substituted by CH2CH3. In a further special preferred embodiment of the invention A is phenyl which is unsubstituted.
  • A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocyclic ring is unsubstituted or substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein.
  • A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the 6-membered aromatic heterocycle in para-pos ⁇ t ⁇ on with regard to the trifluoromethyloxadiazole group.
  • A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the 6-membered aromatic heterocycle in /77ete-position with regard to the trifluoromethyloxadiazole group.
  • A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the 6-membered aromatic heterocycle in with regard to the trifluoromethyloxadiazole group.
  • A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted and wherein the group - C(R 3 R 4 )-NR 1 R 2 is attached to the 6-membered aromatic heterocycle in para-pos ⁇ t ⁇ on with regard to the trifluoromethyloxadiazole group.
  • A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 or 2 identical or different groups R A as defined or preferably defined herein.
  • A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted.
  • the invention relates to the use of compounds of the formula I, or the
  • N-oxides or the agriculturally acceptable salts thereof for combating phytopathogenic harmful fungi, wherein the cyclic moiety A is defined as in subformulae (A.1 ) to (A.12),
  • cyclic moieties A as defined in any one of subformulae (A.1 ) to (A.12) is unsubstituted or substituted by 1 or 2 identical or different groups R A ; and wherein R A is chlorine, fluorine or methyl.
  • R A is chlorine, fluorine or methyl.
  • the cyclic moiety A as defined in any one of subformulae (A.1 ) to (A.12) is unsubstituted.
  • R A is halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl; and wherein any of the aliphatic and cyclic moieties are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R a as defined or preferably defined herein.
  • R A is halogen, cyano, Ci-C6-alkyl, Ci-C6-alk- oxy, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl; and wherein any of the the aliphatic and cyclic moieties are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy and C3-Cs-cycloalkyl; in particular fluorine.
  • R A is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or C1-C6- haloalkoxy; in particular halogen, Ci-C6-alkyl; more particularly R A is chlorine, fluorine or methyl. In a more preferable embodiment R A is chlorine, fluorine or methyl.
  • R a according to the invention is halogen, cyano, NO2, OH , SH , N H 2 , CrC6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs-cycloalkyl.
  • R a is halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy or Cs-Cs- cycloalkyl. More preferably R a is halogen, in particular fluorine.
  • R 1 is H .
  • R 1 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 1 is C2-C6-alkenyl, preferably ethylene.
  • R 1 is C2-C6-alkynyl, preferred ethynyl, 1 -propynyl.
  • R 1 is Cs-Cs- cycloalkyl, preferrably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl.
  • R 1 is Ci-C6-alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 1 is CF3.
  • R 1 is phenyl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 1 is heteroaryl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyriminin.
  • alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxyd
  • R 1 is phenyl. According to a further embodiment R 1 is benzyl.
  • R 1 is naphthyl. According to one embodiment R 1 3- to
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl.
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methyl, ethyl, propyl, butyl, preferably partially or fully
  • halogenated methyl in particular CF 3 .
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy.
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably partially or fully halogenated methoxy, in particular OCF3.
  • R 1 is phenyl.
  • R 1 is phenyl substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3.
  • R 1 is benzyl substituted by CI, F, Br, I , CH 3 , OCH 3 , CF 3 or OCF3.
  • R 1 is naphtyl substituted by CI, F, Br, I , CH 3 , OCH 3 , CF 3 or OCF3.
  • R 1 is thiophene substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 1 is pyrol substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3.
  • R 1 is pyrazol substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3.
  • R 1 is pyrimidin substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3.
  • R 1 is oxydiazol substituted by CI, F, Br, I, CH 3 , OCH3, CF 3 or OCFs.
  • R 1 is H, d-Ce-alkyl, Ca-Ce-cycloalkyl.
  • R 1 is H, CH3, cyclopropyl.
  • R 2 is H.
  • R 2 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 2 is C2-C6-alkenyl, preferably ethylene.
  • R 2 is C2-C6-alkynyl, preferred ethynyl, 1 -propynyl.
  • R 2 is C3-C8- cycloalkyl, preferrably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl.
  • R 2 is Ci-C6-alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 2 is CF3.
  • R 2 is phenyl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 2 is heteroaryl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyriminin.
  • alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxyd
  • R 2 is phenyl. According to a further embodiment R 2 is benzyl.
  • R 2 is naphthyl. According to one embodiment R 2 is a 3- to
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl.
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methyl, ethyl, propyl, butyl, preferably partially or fully
  • halogenated methyl in particular CF3.
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy.
  • the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably partially or fully halogenated methoxy, in particular OCF3.
  • R 2 is phenyl.
  • R 2 is phenyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 2 is benzyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 2 is naphtyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 2 is thiophene substituted by CI, F, Br, I, CH3, OCH3, CF 3 or OCF 3 .
  • R 2 is pyrol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 2 is pyrazol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
  • R 2 is pyrimidin substituted by CI, F, Br, I, CH3, OCH3, CF3 or
  • R 2 is oxydiazol substituted by CI, F, Br, I, CH 3 , OCH3, CF 3 or OCF 3 .
  • R 2 is H, CrC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C3-C 6 -cycloalkyl, phenyl-CrC 4 -alkyl, heteroaryl-CrC 4 -alkyl, phenyl.
  • R 2 is H, d-Ce-alkyl, C 3 -C 6 -cycloalkyl, phenyl-CrC 4 -alkyl, heteroaryl-CrC 4 -alkyl, phenyl.
  • R 2 is H, Ci-C 6 -alkyl, C3-C 6 -cycloalkyl, phenyl-Ci-C 4 -alkyl, phenyl.
  • R 2 is H, CH 3 , CH 2 CH 3 , cyclopropyl, phenyl, benzyl.
  • R 1 is hydrogen, Ci-C6-alkyl, C 2 -C6-alkenyl or C 2 -C6-alkynyl and R 2 is hydrogen, Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Cs-Cs-cycloalkyl, phenyl-Ci-C 4 -alkyl, heteroaryl-Ci-C 4 -alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6- membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 and R 2 independently of each other are hydrogen, Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Cs-Cs-cycloalkyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen, Ci-C6-alkyl, C 2 -C6-alkenyl or C 2 -C6-alkynyl and R 2 is phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen, Ci-C6-alkyl, C 2 -C6-alkenyl or C 2 -C6-alkynyl and R 2 is phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl or phenyl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen or Ci-C4-alkyl and R 2 is Cs-Cs-cycloalkyl, wherein the cycloalkyl group is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen or Ci-C4-alkyl and R 2 is Ci-C6-alkyl, C 2 -C6-alkenyl or C 2 -C6- alkynyl, wherein the aliphatic groups are unsubstituted or carry 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen or Ci-C4-alkyl and R 2 is phenyl, a 5- or 6-membered aromatic heterocycle, phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen or Ci-C4-alkyl and R 2 is phenyl-Ci-C4-alkyl or heteroaryl- Ci-C4-alkyl; wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 is hydrogen or Ci-C4-alkyl and R 2 is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R 1a as defined or preferably defined herein.
  • R 1 and R 2 together with the N atom to which it is bound form a saturated or partially unsaturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatoms.
  • R 1a is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,
  • R 1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or
  • R 1a is halogen or Ci-C6-alkyl
  • R 1 and R 2 together with the N atom to which it is bound form a aziridinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a azetidinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a 1-pyrrolidinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a 1-piperidinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a 1-piperazinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a 1-methyl-4-piperazinyl.
  • R 1 and R 2 together with the N atom to which it is bound form a 4-morpholinyl.
  • R 1a is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,
  • R 1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or
  • R 1a is halogen or Ci-C6-alkyl
  • R 3 is H.
  • R 3 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 3 is Ci-C6-haloalkyl, preferably by halogen substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 3 is H, CH 3 and CF 3 .
  • R 3 is CF 3 .
  • R 4 is H.
  • R 4 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 4 is Ci-C6-haloalkyl, preferably by halogen substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
  • R 4 is H, CH3 and CF3.ln a special embodiment of the invention, R 4 is CF 3 .
  • R 3 and R 4 are independently of each other hydrogen, fluorine, methyl or trifluoromethyl.
  • R 3 and R 4 are independently selected from the group consisting of hydrogen and Ci-C4-alkyl, in particular from hydrogen and CH3.
  • R 3 is hydrogen and R 4 is hydrogen or Ci-C4-alkyl, in particular hydrogen or CH 3 .
  • R 3 and R 4 are both hydrogen. In a further aspect R 3 is hydrogen and R 4 is CH3. In still another aspect R 3 is hydrogen and R 4 is trifluoromethyl. In yet another aspect R 3 and R 4 are both methyl. In one embodiment R 3 and R 4 are both trifluoromethyl.
  • R 3 and R 4 independently of each other are H, CH3 or trifluoromethyl.
  • the present invention relates to compounds (1.1 ) of the formula I
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R a ; wherein R a is halogen, cyano, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
  • heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R 1a ; wherein R 1a is halogen, cyano, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, d-Ce-haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 -haloalkylthio, C 3 -C 8 -cycloalkyl, NHSO2- Ci-C 4
  • R 3 is H, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 4 is H, Ci-C -alkyl or Ci-C -haloalkyl
  • the invention relates to compounds (1.1 ), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.1 ), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.8), and wherein A is unsubstituted.
  • the invention relates to compounds (1.1 ), wherein A is (A.4). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.4), and wherein A is unsubstituted.
  • the present invention relates to compounds (1.2) of the formula I
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio,
  • R a is halogen, cyano, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
  • R 3 , R 4 independently of each other are hydrogen, Ci-C 4 -alkyl or Ci-C 4 -haloalky;
  • the invention relates to compounds (1.2), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.2), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (I.2), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (I.2), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.2), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein.
  • the invention relates to compounds (1.2), wherein A is (A.8), and wherein A is unsubstituted.
  • the invention relates to compounds (I.2), wherein A is (A.4).
  • the invention relates to compounds (1.2), wherein A is (A.4), and wherein R 4 is hydrogen or CH3.
  • the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein.
  • the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein, and wherein R 3 is hydrogen and R 4 is hydrogen or CH 3 .
  • the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is unsubstituted.
  • the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is unsubstituted, and wherein R 3 is hydrogen and wherein R 4 is hydrogen or CH3.
  • the present invention relates to compounds (1.3) of the formula I wherein:
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, C C 6 -alkyl, Ci-C 6 -alkoxy, d-C 6 -alkylthio,
  • R a is halogen, cyano, N0 2 , OH, SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl,
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl;
  • R 3 is hydrogen
  • R 4 is hydrogen, Ci-C4-alkyl or Ci-C4-haloalky
  • the invention relates to compounds (1.3), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.3), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.3), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.3), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein.
  • the invention relates to compounds (1.3), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.3), wherein A is (A.4). In another embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein R 4 is hydrogen or CH 3 . In a further embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein, and wherein R 4 is hydrogen or CH3.
  • the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is unsubstituted, and wherein R 4 is hydrogen or CH3.
  • the present invention relates to compounds (1.4) of the formula I
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from
  • cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein R A is chlorine, fluorine or methyl;
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl;
  • R 3 is hydrogen
  • R 4 is hydrogen or CH3
  • the invention relates to compounds (1.4), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.2), and wherein A is unsubstituted.
  • the invention relates to compounds (I.4), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (I.4), wherein A is (A.4). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.4), and wherein A is unsubstituted.
  • the present invention relates to compounds (1.5) of the formula I
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio,
  • R 3 , R 4 independently of each other are hydrogen, Ci-C4-alkyl or Ci-C4-haloalky;
  • the invention relates to compounds (1.5), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.5), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.5), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.5), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein.
  • the invention relates to compounds (1.5), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.5), wherein A is (A.4). In another embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein R 4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein, and wherein R 3 is hydrogen and R 4 is hydrogen or CH3.
  • the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is unsubstituted, and wherein R 3 is hydrogen and wherein R 4 is hydrogen or CH3.
  • the present invention relates to compounds (1.6) of the formula I
  • A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, N0 2 , OH, NH 2 , SH, Ci-C 6 -alkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio,
  • R 3 is hydrogen
  • R 4 is hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
  • the invention relates to compounds (1.6), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.6), wherein A is (A.2), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.6), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.6), wherein A is (A.8), and wherein A is substituted by 1 group R A as defined or preferably defined herein.
  • the invention relates to compounds (1.6), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.6), wherein A is (A.4). In another embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein R 4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is substituted by 1 group R A as defined or preferably defined herein, and wherein R 4 is hydrogen or CH3.
  • the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is unsubstituted, and wherein R 4 is hydrogen or CH3.
  • the present invention relates to compounds of the formula I.B
  • the present invention relates to compounds of the formula I.C
  • the present invention relates to compounds of the formula I.E
  • the present invention relates to compounds of the formula I.G
  • the present invention relates to compounds of the formula I.H
  • the present invention relates to compounds of the formula I.J or to the use of the compounds of the formula I.J for controlling phytopathogenic fungi.
  • the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
  • the present invention relates to compounds of the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q, I.R or I.S or to the use of the compounds of the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q, I.R or I.S for controlling phytopathogenic fungi.
  • the variables R 3 and R 4 are as defined or preferably defined herein for formula I.
  • the compounds of the formula I can be prepared according to methods or in analogy to methods that are described in the prior art.
  • the synthesis takes advantage of starting materials that are commercially available or may be prepared according to conventional procedures starting from readily available compounds.
  • compounds of the formula I can be prepared by reacting amidines of type II with trifluoroacetic anhydride in an organic solvent, preferably an ethereal solvent at temperatures between 0 °C and 100 °C, preferably at room temperature, as previously described in WO2013/008162.
  • the compounds of the formula I or compositions comprising said compounds according to the invention and the mixtures comprising said compounds and compositions, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota
  • Baseidiomycetes for example, but not limited to the genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungi imperfect!), for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn.
  • Oomycetes for example but not limited to the genus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, for example but not limited to the genus Plasmodiophora; Zygomycetes, for example, but not limited to the genus Rhizopus.
  • Some of the compounds of the formula I and the compositions according to the invention are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g.
  • potatoes which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with compounds I and compositions thereof, respectively is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g.
  • auxin herbicides such as dicamba or 2,4-D
  • bleacher herbicides such as hydroxylphenylpyruvate dioxygena
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ALS inhibitors e.g. described in Pest Managem. Sci.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • RoundupReady ® glyphosate-tolerant, Monsanto, U.S.A.
  • Cultivance ® imidazolinone tolerant, BASF SE, Germany
  • LibertyLink ® glufosinate- tolerant, Bayer CropScience, Germany
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3- hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amyivora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultivars capable of synthe
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. white rust
  • vegetables e. g. A. Candida
  • sunflowers e. g. A. tragopogonis
  • Alternaria spp. Alternaria leaf spot) on vegetables, rape (A. brassico/a or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solan/ or A.
  • B. oryzae on rice and turfs Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana. grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;
  • Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchit) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus
  • anamorph Helminthosporium of Bipolaris
  • spp. leaf spots
  • corn C. carbonum
  • cereals e. g. C. sativus, anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus, anamorph: H.
  • gossyp/ ⁇ corn (e. g. C. graminico/a: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.
  • coccodes black dot
  • beans e. g. C. lindemuthianum
  • soybeans e. g. C. truncatum or C. gloeosporioides
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice
  • Corynespora cassiicoia leaf spots
  • Cycloconium spp. e. g. C. oleaginum on olive trees
  • Cylindrocarpon spp. e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.
  • C liriodendri, teleomorph Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;
  • Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis. tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),
  • spp. wilt, root or stem rot
  • various plants such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. so/anl( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F.
  • G sabinae rust on pears
  • Helminthosporium spp. syn. Drechslera, teleomorph: Cochiioboius
  • Hemileia spp. e. g. H. vastatrix (coffee leaf rust) on coffee
  • Isariopsis clavispora syn. Cladosporium vitis
  • Macrophomina phaseolina syn. phaseo/ ⁇ (root and stem rot) on soybeans and cotton
  • Microdochium syn. Fusarium
  • nivale pink snow mold
  • Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco ⁇ P. tabacina) and soybeans (e. g. P. manshurica);
  • Monilinia spp. e. g.
  • Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum);
  • Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. ha/stediion sunflowers
  • Podosphaera spp. powdery mildew
  • Puccinia spp. rusts on various plants, e. g. . triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P.
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • Pyricularia spp. e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals
  • Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R.
  • collo-cygni Roso-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R.
  • Rhizoctonia spring blight on wheat or barley
  • Rhizopus sto/on/fer b ⁇ ack mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fsiior S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn.
  • Stagonospora nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker! on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S.
  • Leptosphaeria [syn. Phaeosphaer/a] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (p ⁇ um pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P.
  • Puccinia spp. rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • P. graminis seed or black rust
  • me/bom/ae soybean rust
  • the compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • the term "protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola pp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora pp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Candida spp. and Saccharomyces cerevisae Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.
  • the term "stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment.
  • Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent
  • stored products is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • the compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a fungicidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical
  • compositions are prepared in a known manner, such as described by Mollet and
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol
  • glycols DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
  • Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e. g. cellulose, star
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e. g. iron oxide, titan oxide, iron
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • Water-soluble concentrates (SL, LS) 10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%.
  • the active substance dissolves upon dilution with water.
  • a compound I and 1-10 wt% dispersant e. g. polyvinyl pyrrolidone
  • organic solvent e. g. cyclohexanone
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e. g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e. g. aromatic hydrocarbon
  • This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a compound I In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1 -2 wt% thickener e. g. xanthan gum
  • a compound I 50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound I In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • 1 -5 wt% thickener e. g. carboxymethyl cellulose
  • wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce
  • organic solvent blend e. g. fatty acid dimethyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and arylphenol ethoxylate
  • Microcapsules An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g.
  • an isocyanate monomer e. g. diphenylmethene-4,4'-diisocyanatae
  • a protective colloid e. g. polyvinyl alcohol
  • a polyamine e. g.
  • hexamethylenediamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
  • solid carrier e. g. finely divided kaolin
  • a compound I 0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%.
  • solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • LS solutions for seed treatment
  • SE Suspoemulsions
  • FS flowable concentrates
  • DS powders for dry treatment
  • WS water-dispersible powders for slurry treatment
  • compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • a pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • a predosage device usually from a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • Respiration inhibitors Inhibitors of complex III at Q 0 site: azoxystrobin (A.1.1 ), coumeth- oxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1.8), kresoxim- methyl (A.1.9), mandestrobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1 .12), picoxy- strobin (A.1 .13), pyraclostrobin (A.1.14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1 .16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6
  • triclopyricarb/chlorodincarb A.1.20
  • famoxadone A.1 .21
  • fenamidone A.1.21
  • methyl-/V-[2- [(1 ,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate A.1 .22
  • Inhibitors of complex III at Q, site cyazofamid (A.2.1 ), amisulbrom (A.2.2),
  • Inhibitors of complex II benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), 3-(difluoromethyl)-N-methoxy- 1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide (A.3.17), N-[2-(3,4- difluorophenyl)phenyl]-3-(triflu
  • respiration inhibitors diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12).
  • fentin salts e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10)
  • ametoctradin A.4.1 1
  • silthiofam A.4.12).
  • C14 demethylase inhibitors triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromuconazole (B.1 .3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1.6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusilazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1 .17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutraz
  • Delta 14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8).
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 ).
  • Sterol biosynthesis inhibitors chlorphenomizole (B.4.1 ).
  • Phenylamides or acyl amino acid fungicides benalaxyl (C.1 .1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1.6), oxadixyl (C.1.7).
  • nucleic acid synthesis inhibitors hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8).
  • Tubulin inhibitors benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1 .3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyrida- zine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N-ethyl-2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy
  • diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7).
  • Methionine synthesis inhibitors cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3). Protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin
  • MAP / histidine kinase inhibitors fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1.5).
  • G protein inhibitors quinoxyfen (F.2.1 ).
  • Phospholipid biosynthesis inhibitors edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1 .3), isoprothiolane (G.1 .4).
  • Lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7).
  • Phospholipid biosynthesis and cell wall deposition dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7).
  • Inhibitors of oxysterol binding protein oxathiapiprolin (G.5.1 ), 2- ⁇ 3-[2-(1- ⁇ [3,5-bis(difluoromethyl- 1 H-pyrazol-1 -yl]acetyl ⁇ piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ phenyl methanesulfonate (G.5.2), 2- ⁇ 3-[2-(1 - ⁇ [3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl ⁇ piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl ⁇ -3-chlorophenyl methanesulfonate (G.5.3), 4-[1 - [2-[3-(difluoromethyl)-5-methyl-pyrazol-1-y
  • Inorganic active substances Bordeaux mixture (H.1 .1 ), copper (H.1 .2), copper acetate (H.1 .3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7).
  • Organochlorine compounds anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan
  • Guanidines and others guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10).
  • Inhibitors of glucan synthesis validamycin (1.1 .1 ), polyoxin B (1.1.2).
  • Bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1 .4), dazomet (K.1 .5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1.9), di- fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1 .1 1 ), fenitropan (K.1 .12), fenpyrazamine (K.1 .13), flumetover (K.1 .14), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1.18), nitrapyrin (K.1 .19), nitrothal-isopropyl (K
  • abscisic acid (M.1 .1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
  • N.1 Lipid biosynthesis inhibitors alloxydim (N.1 .1 ), alloxydim-sodium (N.1.2), butroxydim (N.1.3), clethodim (N.1.4), clodinafop (N.1 .5), clodinafop-propargyl (N.1.6), cycloxydim (N.1.7), cyhalofop (N.1 .8), cyhalofop-butyl (N.1.9), diclofop(N.1 .10), diclofop-methyl (N.1.1 1 ), fenoxaprop (N.1 .12), fenoxaprop-ethyl (N.1 .13), fenoxaprop-P (N.1 .14), fenoxaprop-P-ethyl (N.1.15), fluazifop (N.1 .16), fluazifop-butyl (N.1 .
  • N.2 ALS inhibitors amidosulfuron (N.2.1 ), azimsulfuron (N.2.2), bensulfuron (N.2.3), bensul- furon-methyl (N.2.4), chlorimuron (N.2.5), chlorimuron-ethyl (N.2.6), chlorsulfuron (N.2.7), cinosulfuron (N.2.8), cyclosulfamuron (N.2.9), ethametsulfuron (N.2.10), ethametsulfuron- methyl (N.2.1 1 ), ethoxysulfuron (N.2.12), flazasulfuron (N.2.13), flucetosulfuron (N.2.14), flupyrsulfuron (N.2.15), flupyrsulfuron-methyl-sodium (N.2.16), foramsulfuron (N.2.17), halosulfuron (N.2.18), halosulfuron-methyl (N.2.19), imazos
  • N.2.80 propoxycarbazone-sodium (N.2.81 ), thiencarbazone (N.2.82), thiencarbazone-methyl (N.2.83), triafamone (N.2.84);
  • N.3 Photosynthesis inhibitors amicarbazone (N.3.1 ); chlorotriazine (N.3.2); ametryn (N.3.3), atrazine (N.3.4), chloridazone (N.3.5), cyanazine (N.3.6), desmetryn (N.3.7), dimethametryn (N.3.8),hexazinone (N.3.9), metribuzin (N.3.10), prometon (N.3.1 1 ), prometryn (N.3.12), pro- pazine (N.3.13), simazine (N.3.14), simetryn (N.3.15), terbumeton (N.3.16), terbuthylazin
  • N.3.17 terbutryn (N.3.18), trietazin (N.3.19); chlorobromuron (N.3.20), chlorotoluron (N.3.21 ), chloroxuron (N.3.22), dimefuron (N.3.23), diuron (N.3.24), fluometuron (N.3.25), isoproturon (N.3.26), isouron (N.3.27), linuron (N.3.28), metamitron (N.3.29), methabenzthiazuron (N.3.30), metobenzuron (N.3.31 ), metoxuron (N.3.32), monolinuron (N.3.33), neburon (N.3.34), siduron (N.3.35), tebuthiuron (N.3.36), thiadiazuron (N.3.37), desmedipham (N.3.38), karbutilat (N.3.39), phenmedipham (N.3.40),
  • N.4 protoporphyrinogen-IX oxidase inhibitors acifluorfen (N.4.1 ), acifluorfen-sodium (N.4.2), azafenidin (N.4.3), bencarbazone (N.4.4), benzfendizone (N.4.5), bifenox (N.4.6), butafenacil (N.4.7), carfentrazone (N.4.8), carfentrazone-ethyl (N.4.9), chlormethoxyfen (N.4.10), cinidon- ethyl (N.4.1 1 ), fluazolate (N.4.12), flufenpyr (N.4.13), flufenpyr-ethyl (N.4.14), flumiclorac (N.4.15), flumiclorac-pentyl (N.4.16), flumioxazin (N.4.17), fluoroglycofen (N.4.18),
  • fluoroglycofen-ethyl N.4.19), fluthiacet (N.4.20), fluthiacet-methyl (N.4.21 ), fomesafen (N.4.22), halosafen (N.4.23), lactofen (N.4.24), oxadiargyl (N.4.25), oxadiazon (N.4.26), oxyfluorfen (N.4.27), pentoxazone (N.4.28), profluazol (N.4.29), pyraclonil (N.4.30), pyraflufen (N.4.31 ), pyraflufen-ethyl (N.4.32), saflufenacil (N.4.33), sulfentrazone (N.4.34), thidiazimin (N.4.35), tiafenacil (N.4.36), trifludimoxazin (N.4.37), ethyl [3-[2-chloro-4-fluor
  • N.5 Bleacher herbicides beflubutamid (N.5.1 ), diflufenican (N.5.2), fluridone (N.5.3), flurochloridone (N.5.4), flurtamone (N.5.5), norflurazon (N.5.6), picolinafen (N.5.7), 4-(3- trifluoromethyl ⁇ phenoxy)-2-(4-trifluoromethylphenyl)->pyrimidine ((N.5.8) CAS 180608-33-7); benzobicyclon (N.5.9), benzofenap (N.5.10), bicyclopyrone (N.5.1 1 ), clomazone (N.5.12), fenquintrione (N.5.13), isoxaflutole (N.5.14), mesotrione (N.5.15), pyrasulfotole (N.5.16), pyrazolynate (N.5.17), pyrazoxyfen (N.5.18), sulcotrione (N.
  • N.6 EPSP synthase inhibitors glyphosate (N.6.1 ), glyphosate-isopropylammonium (N.6.2), glyposate-potassium (N.6.3), glyphosate-trimesium (sulfosate) (N.6.4);
  • Glutamine synthase inhibitors bilanaphos (bialaphos) (N.7.1 ), bilanaphos-sodium (N.7.2), glufosinate (N.7.3), glufosinate-P (N.7.4), glufosinate-ammonium (N.7.5);
  • N.8 DHP synthase inhibitors asulam (N.8.1 );
  • Mitosis inhibitors benfluralin (N.9.1 ), butralin (N.9.2), dinitramine (N.9.3), ethalfluralin (N.9.4), fluchloralin (N.9.5), oryzalin (N.9.6), pendimethalin (N.9.7), prodiamine (N.9.8), trifluralin (N.9.9); amiprophos (N.9.10), amiprophos-methyl (N.9.1 1 ), butamiphos (N.9.12); chlorthal (N.9.13), chlorthal-dimethyl (N.9.14), dithiopyr (N.9.15), thiazopyr (N.9.16), propyzamide
  • N.10 VLCFA inhibitors acetochlor (N.10.1 ), alachlor (N.10.2), butachlor (N.10.3), dimethachlor (N.10.4), dimethenamid (N.10.5), dimethenamid-P (N.10.6), metazachlor (N.10.7), metolachlor (N.10.8), metolachlor-S (N.10.9), pethoxamid (N.10.10), pretilachlor (N.10.1 1 ), propachlor (N.10.12), propisochlor (N.10.13), thenylchlor (N.10.14), flufenacet (N.10.15), mefenacet (N.10.16), diphenamid (N.10.17), naproanilide (N.10.18), napropamide (N.10.19), napropamide- M (N.10.20), fentrazamide (N.10.21 ), anilofos (N.10.22), cafenstrole (
  • N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid (N.1 1.1 ), dichlobenil (N.1 1 .2), flupoxam (N.1 1 .3), indaziflam (N.1 1 .4), isoxaben (N.1 1 .5), triaziflam (N.1 1.6), 1 -cyclohexyl-5- pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine ((N.1 1 .7) CAS 175899-01-1 );
  • N.12 Decoupler herbicides dinoseb (N.12.1 ), dinoterb (N.12.2), DNOC (N.12.3) and its salts; N.13 Auxinic herbicides: 2,4-D (N.13.1 ) and its salts and esters, clacyfos (N.13.2), 2,4-DB (N.13.3) and its salts and esters, aminocyclopyrachlor (N.13.4) and its salts and esters, aminopyralid (N.13.5) and its salts such as aminopyralid-dimethylammonium (N.13.6), aminopyralid-tris(2-hydroxypropyl)ammonium (N.13.7) and its esters, benazolin (N.13.8), benazolin-ethyl (N.13.9), chloramben (N.13.10) and its salts and esters, clomeprop (N.13.1 1 ), clopyralid (N.13
  • N.14 Auxin transport inhibitors diflufenzopyr (N.14.1 ), diflufenzopyr-sodium (N.14.2), naptalam (N.14.3) and naptalam-sodium (N.14.4);
  • N.15.3 cinmethylin (N.15.4), cumyluron (N.15.5), cyclopyrimorate ((N.15.6) CAS 499223-49-3) and its salts and esters, dalapon (N.15.7), dazomet (N.15.8), difenzoquat (N.15.9), difenzoquat- metilsulfate (N.15.10), dimethipin (N.15.1 1 ), DSMA (N.15.12), dymron (N.15.13), endothal (N.15.14) and its salts, etobenzanid (N.15.15), flurenol (N.15.16), flurenol-butyl (N.15.17), flurprimidol (N.15.18), fosamine (N.15.19), fosamine-ammonium (N.15.20), indanofan (N.15.21 ),
  • Acetylcholine esterase (AChE) inhibitors aldicarb (0.1.1 ), alanycarb (0.1 .2), bendiocarb (0.1 .3), benfuracarb (0.1.4), butocarboxim (0.1.5), butoxycarboxim (0.1 .6), carbaryl (0.1.7), carbofuran (0.1.8), carbosulfan (0.1 .9), ethiofencarb (0.1 .10), fenobucarb (0.1 .1 1 ),
  • vamidothion (0.1 .90), vamidothion (0.1 .91 );
  • GABA-gated chloride channel antagonists endosulfan (0.2.1 ), chlordane (0.2.2); ethiprole (0.2.3), fipronil (0.2.4), flufiprole (0.2.5), pyrafluprole (0.2.6), pyriprole (0.2.7);
  • 0.8 miscellaneous non-specific (multi-site) inhibitors methyl bromide (0.8.1 ) and other alkyl halides; chloropicrin (0.8.2), sulfuryl fluoride (0.8.3), borax (0.8.4), tartar emetic (0.8.5);
  • O.10 Mite growth inhibitors clofentezine (O.10.1 ), hexythiazox (O.10.2), diflovidazin (O.10.3); etoxazole (0.10.4);
  • 0.1 1 Microbial disruptors of insect midgut membranes the Bt crop proteins: Cry1 Ab, Cry1 Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
  • Inhibitors of mitochondrial ATP synthase diafenthiuron (0.12.1 ); azocyclotin (0.12.2), cyhexatin (0.12.3), fenbutatin oxide (0.12.4), propargite (0.12.5), tetradifon (0.12.6);
  • Nicotinic acetylcholine receptor (nAChR) channel blockers bensultap (0.14.1 ), cartap hydrochloride (0.14.2), thiocyclam (0.14.3), thiosultap sodium (0.14.4);
  • Inhibitors of the chitin biosynthesis type 0 bistrifluron (0.15.1 ), chlorfluazuron (0.15.2), diflubenzuron (0.15.3), flucycloxuron (0.15.4), flufenoxuron (0.15.5), hexaflumuron (0.15.6), lufenuron (0.15.7), novaluron (0.15.8), noviflumuron (0.15.9), teflubenzuron (0.15.10), triflumuron (0.15.1 1 );
  • Inhibitors of the chitin biosynthesis type 1 buprofezin (0.16.1 );
  • Ecdyson receptor agonists methoxyfenozide (0.18.1 ), tebufenozide (0.18.2),
  • halofenozide (0.18.3), fufenozide (0.18.4), chromafenozide (0.18.5);
  • Octopamin receptor agonists amitraz (0.19.1 );
  • Mitochondrial complex III electron transport inhibitors hydramethylnon (O.20.1 ), acequinocyl (O.20.2), fluacrypyrim (O.20.3);
  • Mitochondrial complex I electron transport inhibitors fenazaquin (0.21.1 ), fenpyroximate (0.21.2), pyrimidifen (0.21 .3), pyridaben (0.21.4), tebufenpyrad (0.21.5), tolfenpyrad (0.21.6); rotenone (0.21 .7);
  • Inhibitors of the of acetyl CoA carboxylase spirodiclofen (0.23.1 ), spiromesifen (0.23.2), spirotetramat (0.23.3);
  • Mitochondrial complex IV electron transport inhibitors aluminium phosphide (0.24.1 ), calcium phosphide (0.24.2), phosphine (0.24.3), zinc phosphide (0.24.4), cyanide (0.24.5); 0.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen (0.25.1 ), cyflumetofen (0.25.2);
  • insecticidal active compounds of unknown or uncertain mode of action afidopyropen (0.27.1 ), afoxolaner (0.27.2), azadirachtin (0.27.3), amidoflumet (0.27.4), benzoximate (0.27.5), bifenazate (0.27.6), broflanilide (0.27.7), bromopropylate (0.27.8), chinomethionat (0.27.9), cryolite (0.27.10), dicloromezotiaz (0.27.1 1 ), dicofol (0.27.12), flufenerim (0.27.13), flometoquin (0.27.14), fluensulfone (0.27.15), fluhexafon (0.27.16), fluopyram (0.27.17), flu pyradifu rone (0.27.18), fluralaner (0.27.19), metoxadiazone (0.27.20), piperonyl butoxide (0.27.21 ), pyflub
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • fungicide e. g. one or more fungicide from the groups A) to K
  • combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1 .
  • the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
  • the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
  • the weight ratio of component 1 ) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1.
  • any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1 ).
  • mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q 0 site in group A), more preferably selected from compounds (A.1.1 ), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1 .12), (A.1.13), (A.1 .14), (A.1.17), (A.1 .21 ), (A.1.24), (A.1.25), (A.1 .26), (A.1.27), (A.1 .30), (A.1.31 ), (A.1.32), (A.1 .34) and
  • mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from compounds (A.2.1 ), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
  • mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.1 1 ), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21 ), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.28), (A.3.29), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39);
  • mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).
  • mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from
  • mixtures comprising as component 2) at least one active substance selected from Delta 14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
  • mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1 ), (C.1 .2), (C.1.4) and (C.1.5); particularly selected from (C.1 .1 ) and (C.1.4).
  • mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).
  • mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1.5) and (D.2.6).
  • mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1 ), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).
  • mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
  • mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (I.2.5).
  • mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1 .2), (J.1.5) and (J.1 .8); in particular (J.1.5).
  • mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41 ), (K.1 .42), (K.1.44), (K.1 .45), (K.1.47) and (K.1.49); particularly selected from (K.1 .41 ), (K.1.44), (K.1 .45), (K.1.47) and (K.1 .49).
  • the present invention furthermore relates to mixtures comprising one compound of the formula I (component 1 ) and one pesticide II (component 2), wherein pesticide II is selected from the column "Co. 2" of the lines B-1 to B-727 of Table B.
  • a further embodiment relates to the mixtures B-1 to B-727 listed in Table B, where a row of Table B corresponds in each case to a fungicidal mixture comprising as active components one of the in the present specification individualized compounds of formula I, i.e.
  • Another embodiment relates to the mixtures B-1 to B-727 listed in Table B, where a row of
  • Table B corresponds in each case to a fungicidal mixture comprising as active components one of the compounds Ex-1 to Ex-7 of formula I as defined below in table I (component 1 in column “Co.1 ”) and the respective pesticide II from groups A) to O) (component 2) stated in the row in question.
  • compositions described in Table B comprise the active components in synergistically effective amounts.
  • Table B Mixtures comprising as active components one indiviualized compound of the fomula I (in column Co. 1 ), and as component 2) (in column Co. 2) one pesticide from groups A) to O) [which is coded e. g. as (A.1 .1 ) for azoxystrobin as defined above].
  • Mixt. Co.1 Co.2 Mixt. Co.1 Co.2
  • Mixt. Co.1 Co.2 Mixt. Co.1 Co.2
  • Co.1 Co.2 Mixt. Co.1 Co.2
  • B-2 (I) (A.1.2) B-44 (I) (A.3.7) B-86 (I) (A.4.10)
  • B-26 (I) (A.1.26) B-68 (I) (A.3.31) B-110 (I) (B.1.22)
  • B-27 (I) (A.1.27) B-69 (I) (A.3.32) B-111 (I) (B.1.23)
  • B-28 (I) (A.1.30) B-70 (I) (A.3.33) B-112 (I) (B.1.24)
  • B-29 (I) (A.1.31) B-71 (I) (A.3.34) B-113 (I) (B.1.25)
  • B-33 (I) (A.2.3) B-75 (I) (A.3.38) B-117 (I) (B.1.29)
  • B-34 (I) (A.2.4) B-76 (I) (A.3.39) B-118 (I) (B.1.30)
  • B-382 (I) (N.10.2) B-424 (I) (0.1 .7) B-466 (I) (0.2.1 1 )
  • B-394 (I) (N.13.4) B-436 (I) (0.1.19) B-478 (I) (0.3.7)
  • B-397 (I) (N.13.7) B-439 (I) (0.1.22) B-481 (I) (0.3.10)
  • B-402 (I) (N.14.3) B-444 (I) (0.1.27) B-486 (I) (0.3.15)
  • B-410 (I) (N.17.5) B-452 (I) (0.1.35) B-494 (I) (0.3.23)
  • B-41 1 (I) (N.17.6) B-453 (I) (0.1.36) B-495 (I) (0.3.24)
  • B-412 (I) (N.17.7) B-454 (I) (0.1.37) B-496 (I) (0.3.25)
  • B-420 (I) (0.1.3) B-462 (I) (0.2.7) B-504 (I) (0.4.6) Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2
  • B-506 (I) (0.4.8) B-548 (I) (0.8.4) B-590 (I) (0.21.2)
  • B-526 (0.5.4) B-568 (I) (0.15.7) B-610 (I) (0.26.1 )
  • B-529 (I) (0.5.7) B-571 (I) (0.15.10) B-613 (I) (0.26.4)
  • B-540 (I) (0.7.2) B-582 (I) (0.18.3) B-624 (I) (0.26.15)
  • B-542 (I) (0.7.4) B-584 (I) (0.18.5) B-626 (I) (0.26.17)
  • B-631 (I) (0.27.4)
  • B-664 (I) (0.27.37)
  • B-697 (I) (O.27.70)
  • B-634 (I) (0.27.7) B-667 (I) (O.27.40) B-700 (I) (0.27.73)
  • B-644 (I) (0.27.17) B-677 (I) (O.27.50) B-710 (I) (0.27.83)
  • the mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
  • mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the
  • the compounds of formula I can be prepared according to the methods outlined below.
  • N-methyl-1 -[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl] ethanamine obtained in step 1.2 (8.5 g, 1 eq.) in dichloromethane (100 mL) was added triethylamine (5.9 g, 2.2 eq.) and acetyl chloride (2.3 g, 1 .1 eq.). The mixture was stirred overnight, before it was diluted with dichloromethane and washed with aqueous 1 N hydrochloric acid.
  • tetrahydrofuran 50 mL was added hydroxylamine hydrochloride (4.2 g, 1.5 eq.) and potassium carbonate (4.5 g, 0.8 eq.) in 20 mL water. The mixture was stirred overnight at 23 °C and the progress of the reaction was monitored by HPLC. It was filtered, washed five times with toluene and concentrated under reduced pressure to afford the title compound (10 g) that was used directly without further purification.
  • Table I Compounds Ex-1 to Ex-34 of formula I. Ex, wherein A corresponds to subformula (A.4), wherein A is unsubstituted, and wherein the meaning of R 1 , R 2 , R 3 and R 4 are as defined in each line, and wherein # denotes the point of attachment of the NR 1 R 2 group to the CR 3 R 4 moiety.

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Abstract

Substituted oxadiazoles for combating phytopathogenic fungi. The present invention relates the use of the compounds of the formula I or the N-oxides, or the agriculturally acceptable salts thereof for combating phytopathogenic harmful fungi, wherein the variables are defined as given in the description and claims. Further present invention relates to certain oxadiazole compounds, to mixtures comprising at least one compound of the formula I and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one compound of the formula I and to agrochemical compositions further comprising seeds.

Description

Substituted oxadiazoles for combating phytopathogenic fungi
The present invention relates to the use oxadiazoles of the formula I, or an N-oxide and/or their agriculturally useful for controlling phytopathogenic fungi, or to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof; the present invention also relates to mixtures comprising at least one such compound of the formula I and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators; and to agrochemical compositions comprising at least one such compound of the formula I and to agrochemical compositions further comprising seeds.
EP 276432 A2 relates to 3-phenyl-5-trifluoromethyloxadiazole derivatives and to their use to combat phytopathogenic microorganisms. WO 2013/008162 describes trifluoromethyl- oxadiazole derivatives with HDAC4 inhibitory activity and their medical use, particularly in the treatment of Huntington's disease, muscle atrophy and diabetes/metabolic syndrome. WO1 1088192, WO 201 1088181 describes the medicinal use of trifluoromethyl-oxadiazole derivatives. A use for controlling phytopathogenic fungi is not described. WO 2015/185485 was published after the date of filing of the present application and describes the use of certain substituted oxadiazoles for combating phytopathogenic fungi
In many cases, in particular at low application rates, the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an objective of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic fungi. This objective is achieved by the oxadiazoles of the formula I and/or their agriculturally useful salts for controlling phytopathogenic fungi.
Accordingly, the present invention rel mpounds of the formula I
Figure imgf000002_0001
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio,
Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein Ra is halogen, cyano, N02, OH, SH, NH2, d-C6-alkyl, C C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs- cycloalkyl; R1, R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Ce-cycloalkyl, C3-C6-cycloalkenyl, C(=0)-(Ci-C6-alkyl), C(=0)-(Ci-C6-alkoxy), phenyl- Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a; or
R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 , 2 or 3 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two Chb groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a; wherein
R1a is halogen, cyano, N02, OH, SH, NH2, d-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, NHSO2- Ci-C4-alkyl, (C=0)-(Ci-C4-alkyl), C(=0)-(Ci-C4-alkoxy) or Ci-C6-alkylsulfonyl;
R3 is H, Ci-C4-alkyl, Ci-C4-haloalkyl;
R4 is H, Ci-C4-alkyl, Ci-C4-haloalkyl;
or the N-oxides, or the agriculturally acceptable salts thereof for combating phytopathogenic harmful fungi. Agriculturally acceptable salts of the compounds of the formula I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably
diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
Anions of acceptable acid addition salts are primarily chloride, bromide, fluoride,
hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
Compounds of the formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers arising from restricted rotation about a single bond of asymmetric groups and geometric isomers. They also form part of the subject matter of the present invention. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, e.g. a racemate, individual
stereoisomers, or as an optically active form.
Compounds of the formula I can be present in different crystal modifications whose biological activity may differ. They also form part of the subject matter of the present invention.
In respect of the variables, the embodiments of the intermediates obtained during preparation of compounds I correspond to the embodiments of the compounds of formula I . The term
"compounds I" refers to compounds of formula I .
In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
The moieties having two ore more possibilities to be attached apply following:
The moieties having no brackets in the name are bonded via the last moiety e.g. C2-C6- alkenyloxyimino-Ci-C4-alkyl is bonded via Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl is bonded via
Ci-C4-alkyl etc.
The moieties having brackets in the name are bonded via the first moiety e.g. C(=0)-(Ci-C6- alkyl) is bonded via C=0 as indicated by the number valence of the carbon atom, etc.
The term "halogen" refers to fluorine, chlorine, bromine and iodine.
The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl.
The term "CrC6-haloalkyl" refers to a straight-chained or branched alkyl group having 1 to 6 carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example chloromethyl,
bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 - fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2- fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, CH2-C2F5, CF2-C2F5, CF(CF3)2, 1 -(fluoromethyl)-2-fluoroethyl, l -(chloromethyl)- 2-chloroethyl, 1 -(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.
The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as defined above) which is bonded via an oxygen, at any position in the alkyl group, for example methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2- methylpropoxy or 1 ,1-dimethylethoxy.
The term "Ci-C6-haloalkoxy" refers to a Ci-C6-alkoxy group as defined above, wherein some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCIs, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2- dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1-(CH2Br)-2-bromo-"ethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
The terms "phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl" refer to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a phenyl or hetereoaryl radical respectively.
The term "CrC4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C4-alkylthio-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkylthio group.
The term "Ci-Ce-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term "CrC6-haloalkylthio" as used herein refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyi group.
The term "Ci-C6-alkylsulfinyl" refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded through a -S(=0)- moiety, at any position in the alkyl group, for example methylsulfinyl and ethylsulfinyl, and the like. Accordingly, the term "C1-C6- haloalkylsulfinyl" refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)- moiety, at any position in the haloalkyi group. The term "CrC6-alkylsulfonyl" refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)2- moiety, at any position in the alkyl group, for example methylsulfonyl. Accordingly, the term "Ci-C6-haloalkylsulfonyl" refers to straight-chain or branched haloalkyi group having 1 to 6 carbon atoms (as defined above), bonded through a -S(=0)2- moiety, at any position in the haloalkyi group.
The term "hydroxyCi-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a OH group.
The term "aminoCi-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a NH2 group.
The term "Ci-C4-alkylamino-Ci-C4-alkyl" refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkyl-NH- group which is bound through the nitrogen. Likewise the term "diCi-C4-alkylamino-Ci-C4-alkyl" refers to refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a (Ci-C4-alkyl)2N- group which is bound through the nitrogen. The term "aminocarbonyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a -(C=0)-NH2 group.
The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2- propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-
1- propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, 1-propynyl,
2- propynyl (propargyl), 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl.
The term "Cs-Cs-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
The term "Cs-Cs-cycloalkyloxy" refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via an oxygen.
The term "C(=0)-(Ci-C4-alkyl)" refers to a radical which is attached through the carbon atom of the C(=0) group as indicated by the number valence of the carbon atom.
The term "aliphatic" refers to compounds or radicals composed of carbon and hydrogen and which are non-aromatic compounds. An alicyclic compound or radical is an organic compound that is both aliphatic and cyclic. They contain one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character.
The terms "cyclic moiety" or "cyclic group'Yefer to a radical which is an alicyclic ring or an aromatic ring, such as, for example, phenyl or heteroaryl.
The term "and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a" refers to aliphatic groups, cyclic groups and groups, which contain an aliphatic and a cyclic moiety in one group, such as in, for example, phenyl-Ci-C4-alkyl; therefore a group which contains an aliphatic and a cyclic moiety both of these moieties may be substituted or unsubstituted independently of each other.
The term "heteroaryl" refers to aromatic monocyclic or polycyclic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S.
The term "phenyl" refers to an aromatic ring systems incuding six carbon atoms (commonly referred to as benzene ring). In association with the group A the term "phenyl" is to be interpreted as a benzene ring or phenylene ring, which is attached to both, the oxadiazole moiety and the -CR3R4- group.
The term "saturated or partially unsaturated 3-, 4-, 5-, 6- or 7-membered carbocycle" is to be understood as meaning both saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members. Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.
The term "3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms", is to be understood as meaning both, aromatic mono- and bicyclic heteroaromatic ring systems, and also saturated and partially unsaturated heterocycles, for example:
a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of N, O and S as ring members such as oxirane, aziridine, thiirane, oxetane, azetidine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine;
and a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of N, O and S as ring members such as 2-tetrahydro- furanyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,
5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5- yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 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-isoxazolin-5-yl,
4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4-isoth iazoli n-4-y 1 , 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isoth iazoli n-5-y 1 , 2,3- dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4- tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5- hexahydrotriazin-2-yl and 1 ,2,4-hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and
a 7-membered saturated or partially unsaturated heterocycle such as tetra- and
hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6- tetrahydro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or- 4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5- ,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4- oxazepinyl, tetra- and hexahydro-1 , 3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals; and
the term "5- or 6-membered heteroaryl" or the term "5- or 6-membered aromatic heterocycle" refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example, a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl- 1-yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4- thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or
a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl. In respect of the variables, the embodiments of the intermediates correspond to the
embodiments of the compounds I. Preference is given to those compounds I and, where applicable, also to compounds of all sub-formulae provided herein, wherein all variables have independently of each other or more preferably in combination (any possible combination of 2 or more substituents as defined herein) the following meanings:
In one aspect of the invention A is phenyl which is unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA as defined or preferably defined herein and wherein the group - C(R3R4)-NR1 R2 is attached to the phenyl ring in para-pos\t\on with regard to the
trifluoromethyloxadiazole group.
In one aspect of the invention A is phenyl which is unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA as defined or preferably defined herein and wherein the group - C(R3R4)-NR1 R2 is attached to the phenyl ring in /^e/a-position with regard to the
trifluoromethyloxadiazole group.
In a further aspect of the invention A is phenyl which is substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein and wherein the group -C(R3R4)-NR1R2 is attached to the phenyl ring in para-pos\t\on with regard to the trifluoromethyloxadiazole group. In another aspect of the invention A is phenyl which is unsubstituted and wherein the group - C(R3R4)-NR1 R2 is attached to the phenyl ring in para-pos\t\on with regard to the
trifluoromethyloxadiazole group.
In a preferred embodiment of the invention A is phenyl substituted by RA selected from halogen, or Ci-C6-alkyl. In a further preferred embodiment of the invention A is phenyl substituted by halogen. In a special preferred embodiment of the invention A is phenyl substituted by F. In a further special preferred embodiment of the invention A is phenyl substituted by CI.
In a further preferred embodiment of the invention A is phenyl substituted by Ci-C6-alkyl. In a special preferred embodiment of the invention A is phenyl substituted by CH3. In a further special preferred embodiment of the invention A is phenyl substituted by CH2CH3. In a further special preferred embodiment of the invention A is phenyl which is unsubstituted.
In one embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocyclic ring is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein.
In a further embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein and wherein the group - C(R3R4)-NR1 R2 is attached to the 6-membered aromatic heterocycle in para-pos\t\on with regard to the trifluoromethyloxadiazole group.
In a further embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein and wherein the group - C(R3R4)-NR1 R2 is attached to the 6-membered aromatic heterocycle in /77ete-position with regard to the trifluoromethyloxadiazole group.
In a further embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein and wherein the group - C(R3R4)-NR1 R2 is attached to the 6-membered aromatic heterocycle in
Figure imgf000009_0001
with regard to the trifluoromethyloxadiazole group.
In a further embodiment A is a 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 or 2 nitrogen atoms as ring member atoms; and wherein the aromatic heterocycle is unsubstituted and wherein the group - C(R3R4)-NR1 R2 is attached to the 6-membered aromatic heterocycle in para-pos\t\on with regard to the trifluoromethyloxadiazole group.
In a further preferred embodiment A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 or 2 identical or different groups RA as defined or preferably defined herein.
In a further preferred embodiment A is a 5-membered aromatic heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted.
In one embodiment the invention relates to the use of compounds of the formula I, or the
N-oxides, or the agriculturally acceptable salts thereof for combating phytopathogenic harmful fungi, wherein the cyclic moiety A is defined as in subformulae (A.1 ) to (A.12),
Figure imgf000009_0002
(A.1 ) (A.2) (A.3) (A.4)
Figure imgf000010_0001
(A.6) (A.7)
Figure imgf000010_0002
(A.9) (A.10) (A.1 1 ) (A.12) wherein #1 denotes the position which is bound to the trifluoromethyloxadiazole moiety and #2 denotes the position, which is connected to the -C(R3R4)-N R1 R2 group of compounds of the formula I; and wherein the cyclic moiety A is unsubstituted or substituted by 1 or 2 identical or different groups RA and wherein RA is as defined or preferably defined herein. In another embodiment the cyclic moieties A as defined in any one of subformulae (A.1 ) to (A.12) is unsubstituted or substituted by 1 or 2 identical or different groups RA; and wherein RA is chlorine, fluorine or methyl. In a preferred embodiment the cyclic moiety A as defined in any one of subformulae (A.1 ) to (A.12) is unsubstituted.
In a preferred embodiment of the invention RA is halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl; and wherein any of the aliphatic and cyclic moieties are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups Ra as defined or preferably defined herein.
In another preferred embodiment of the invention RA is halogen, cyano, Ci-C6-alkyl, Ci-C6-alk- oxy, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl; and wherein any of the the aliphatic and cyclic moieties are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups selected from halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy and C3-Cs-cycloalkyl; in particular fluorine.
More preferably RA is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or C1-C6- haloalkoxy; in particular halogen, Ci-C6-alkyl; more particularly RA is chlorine, fluorine or methyl. In a more preferable embodiment RA is chlorine, fluorine or methyl.
Ra according to the invention is halogen, cyano, NO2, OH , SH , N H2, CrC6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs-cycloalkyl. In a preferred embodiment of the invention Ra is halogen, cyano, Ci-C6-alkyl, Ci-C6-alkoxy or Cs-Cs- cycloalkyl. More preferably Ra is halogen, in particular fluorine.
According to one embodiment R1 is H . According to one embodiment R1 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. According to a further embodiment R1 is C2-C6-alkenyl, preferably ethylene. According to a further embodiment R1 is C2-C6-alkynyl, preferred ethynyl, 1 -propynyl. According to a further embodiment R1 is Cs-Cs- cycloalkyl, preferrably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl. According to one embodiment R1 is Ci-C6-alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a special embodiment of the invention R1 is CF3.
According to one embodiment R1 is C(=0)-(Ci-C6-alkyl). According to one embodiment R1 is C(=0)-(Ci-C6-alkyl), wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. According to one embodiment R1 is C(=0)-(Ci-C6-alkoxy), wherein alkoxy is preferrably methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy. According to one embodiment R1 is phenyl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
According to one embodiment R1 is heteroaryl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyriminin.
According to one embodiment R1 is phenyl. According to a further embodiment R1 is benzyl.
According to a further embodiment R1 is naphthyl. According to one embodiment R1 3- to
10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms especially, furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyriminin.
According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methyl, ethyl, propyl, butyl, preferably partially or fully
halogenated methyl, in particular CF3. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably partially or fully halogenated methoxy, in particular OCF3. In a special embodiment of the invention, R1 is phenyl. In a further special embodiment of the invention, R1 is phenyl substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is benzyl substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment R1 is naphtyl substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is thiophene substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is pyrol substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is pyrazol substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is pyrimidin substituted by CI, F, Br, I , CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R1 is oxydiazol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCFs.
In a preferred embodiment R1 is H, d-Ce-alkyl, Ca-Ce-cycloalkyl. In a special preferred
embodiment R1 is H, CH3, cyclopropyl.
According to one embodiment R2 is H. According to one embodiment R2 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. According to a further embodiment R2 is C2-C6-alkenyl, preferably ethylene. According to a further embodiment R2 is C2-C6-alkynyl, preferred ethynyl, 1 -propynyl. According to a further embodiment R2 is C3-C8- cycloalkyl, preferrably cyclopropyl, cyclobutyl, cyclopentyl, in particular cyclopropyl, cyclopentyl or cyclohexyl.
According to one embodiment R2 is Ci-C6-alkyl substituted by halogen, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a special embodiment of the invention, R2 is CF3.
According to one embodiment R2 is C(=0)-(Ci-C6-alkyl). According to one embodiment R2 is C(=0)-(CrC6-alkyl), wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t- butyl, in particular methyl, ethyl. According to one embodiment R2 is C(=0)-(Ci-C6-alkoxy), wherein alkoxy is preferrably methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy.
According to one embodiment R2 is phenyl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
According to one embodiment R2 is heteroaryl-Ci-C4-alkyl, wherein alkyl is preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl and wherein heteroaryl is furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyriminin.
According to one embodiment R2 is phenyl. According to a further embodiment R2 is benzyl.
According to a further embodiment R2 is naphthyl. According to one embodiment R2 is a 3- to
10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms especially, furan, thiophen, pyrazol, isoxazol, imidazole, oxazol, thiazol, triazol, oxydiazol, pyrol, pyrimidin.
According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methyl, ethyl, propyl, butyl, preferably methyl. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methyl, ethyl, propyl, butyl, preferably partially or fully
halogenated methyl, in particular CF3. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of methoxy, ethoxy, propoxy, butoxy, preferably methoxy. According to a further embodiment the above mentioned groups may carry one, two, three or four identical or different substituents selected from the group consisting of partially or fully halogenated methoxy, ethoxy, propoxy, butoxy, preferably partially or fully halogenated methoxy, in particular OCF3. In a special embodiment of the invention, R2 is phenyl. In a further special embodiment of the invention, R2 is phenyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R2 is benzyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment R2 is naphtyl substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R2 is thiophene substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R2 is pyrol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R2 is pyrazol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3. In a further special embodiment of the invention, R2 is pyrimidin substituted by CI, F, Br, I, CH3, OCH3, CF3 or
OCF3. In a further special embodiment of the invention, R2 is oxydiazol substituted by CI, F, Br, I, CH3, OCH3, CF3 or OCF3.
In a preferred embodiment R2 is H, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl-CrC4-alkyl, heteroaryl-CrC4-alkyl, phenyl. In a special preferred embodiment R2 is H, d-Ce-alkyl, C3-C6-cycloalkyl, phenyl-CrC4-alkyl, heteroaryl-CrC4-alkyl, phenyl. In a further special preferred embodiment R2 is H, Ci-C6-alkyl, C3-C6-cycloalkyl, phenyl-Ci-C4-alkyl, phenyl. In a further special preferred embodiment R2 is H, CH3, CH2CH3, cyclopropyl, phenyl, benzyl. In another preferred embodiment R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or a 3- to 10-membered saturated, partially unsaturated mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6- membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a; wherein R1a is halogen, cyano, NO2, OH, SH, NH2, CrC6-alkyl,
d-Ce-haloalkyl, C C6-alkoxy, Ci-C6-haloalkoxy, C C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, NHS02-Ci-C4-alkyl, (C=0)-(Ci-C4-alkyl), C(=0)-(Ci-C4-alkoxy) or Ci-C6-alkylsulfonyl; and wherein R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy).
In a further embodiment R1 and R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C(=0)-(CrC6-alkyl), C(=0)-(CrC6-alkoxy), phenyl-Ci-C4-alkyl or phenyl; and wherein the aliphatic and the cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined herein.
In another embodiment R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl and R2 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6- membered aromatic heterocycle, wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein. In one aspect of the invention R1 and R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In another embodiment R1 is hydrogen, CrC6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C3-C8- cycloalkyl and R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein. In another embodiment R1 is hydrogen, Ci-Ce-alkyI, C2-Ce-alkenyl, C2-Ce-alkynyl or C3-C8- cycloalkyl and R2 is C(=0)-(Ci-C6-alkyl); and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group fluorine, chlorine and methyl.
In one aspect of the invention R1 and R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In a further aspect of the invention R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl and R2 is phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In a further aspect of the invention R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl and R2 is phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl or phenyl; and wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle wherein the ring includes besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein. In one embodiment R1 is hydrogen or Ci-C4-alkyl and R2 is Cs-Cs-cycloalkyl, wherein the cycloalkyl group is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In one embodiment R1 is hydrogen or Ci-C4-alkyl and R2 is Ci-C6-alkyl, C2-C6-alkenyl or C2-C6- alkynyl, wherein the aliphatic groups are unsubstituted or carry 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein. In one embodiment R1 is hydrogen or Ci-C4-alkyl and R2 is phenyl, a 5- or 6-membered aromatic heterocycle, phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein. In one embodiment R1 is hydrogen or Ci-C4-alkyl and R2 is phenyl-Ci-C4-alkyl or heteroaryl- Ci-C4-alkyl; wherein the heteroaryl group is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the aromatic heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; wherein any of the aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In one embodiment R1 is hydrogen or Ci-C4-alkyl and R2 is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the cyclic groups are unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein.
In one embodiment of the invention R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms 1 , 2 or 3 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1 a; wherein R1a is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, NHS02-Ci-C4-alkyl, (C=0)-Ci-C4-alkyl, C(=0)-Ci-C4-alkoxy or Ci-C6-alkylsulfonyl.
In one embodiment of the invention R1 and R2 together with the N atom to which it is bound form a saturated or partially unsaturated 3- to 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatoms. In one embodiment of the invention R1 and R2 together with the N to which it is bound form a saturated or partially unsaturated 3- to 6-membered heterocycle, wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S).ln one embodiment R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated monocyclic 5- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein; particularly R1a is halogen or Ci-C6-alkyl. In a further embodiment R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated monocyclic 5- or 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 further heteroatom independently selected from N, O and S as ring member atoms; and wherein one or two Chb groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein; particularly R1a is halogen or d-Ce-alkyl.
In one embodiment of the invention R1a is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy. In another preferred aspect of the invention R1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or
difluoromethoxy. In a more preferred aspect of the invention R1a is halogen or Ci-C6-alkyl;
particularly fluorine, chlorine or methyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a aziridinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a azetidinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a 1-pyrrolidinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a 1-piperidinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a 1-piperazinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a 1-methyl-4-piperazinyl.
In one special preferred embodiment of the invention R1 and R2 together with the N atom to which it is bound form a 4-morpholinyl.
In one embodiment of the invention R1a is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy. In another preferred aspect of the invention R1a is fluorine, chlorine, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl or
difluoromethoxy. In a more preferred aspect of the invention R1a is halogen or Ci-C6-alkyl;
particularly fluorine, chlorine or methyl.
According to one embodiment R3 is H. According to one embodiment R3 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
According to one embodiment R3 is Ci-C6-haloalkyl, preferably by halogen substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a preferred embodiment of the invention, R3 is H, CH3 and CF3. In a special embodiment of the invention, R3 is CF3.
According to one embodiment R4 is H. According to one embodiment R4 is Ci-C6-alkyl, preferably methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl.
According to one embodiment R4 is Ci-C6-haloalkyl, preferably by halogen substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, in particular methyl, ethyl. In a preferred embodiment of the invention, R4 is H, CH3 and CF3.ln a special embodiment of the invention, R4 is CF3.
According to one embodiment R3 and R4 are independently of each other hydrogen, fluorine, methyl or trifluoromethyl. In a further embodiment R3 and R4 are independently selected from the group consisting of hydrogen and Ci-C4-alkyl, in particular from hydrogen and CH3. According to another embodiment R3 is hydrogen and R4 is hydrogen or Ci-C4-alkyl, in particular hydrogen or CH3.
In another aspect R3 and R4 are both hydrogen. In a further aspect R3 is hydrogen and R4 is CH3. In still another aspect R3 is hydrogen and R4 is trifluoromethyl. In yet another aspect R3 and R4 are both methyl. In one embodiment R3 and R4 are both trifluoromethyl.
In yet another embodiment R3 and R4 independently of each other are H, CH3 or trifluoromethyl.
In one embodiment the present invention relates to compounds (1.1 ) of the formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein Ra is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or C3-C8- cycloalkyl;
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
C3-C6-cycloalkenyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the
heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a; wherein R1a is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, NHSO2- Ci-C4-alkyl, (C=0)-Ci-C4-alkyl, C(=0)-Ci-C4-alkoxy, Ci-C6-alkylsulfonyl or Ci-C6- haloalkylsulfonyl;
R2 is C(=0)-(Ci-C6-alkyl), C(=0)-(Ci-C6-alkoxy); or R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 , 2 or 3 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two Ch groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein;
R3 is H, Ci-C4-alkyl or Ci-C4-haloalkyl;
R4 is H, Ci-C -alkyl or Ci-C -haloalkyl;
or the N-oxides, or the agriculturally acceptable salts thereof.
In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.1 ), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.8), and wherein A is unsubstituted.
In another embodiment the invention relates to compounds (1.1 ), wherein A is (A.4). In a further embodiment the invention relates to compounds (1.1 ), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.1 ), wherein A is (A.4), and wherein A is unsubstituted.
In one embodiment the present invention relates to compounds (1.2) of the formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio,
Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein
Ra is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs- cycloalkyl;
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
C3-C6-cycloalkenyl, phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or a 3- to
10-membered saturated, partially unsaturated mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a; wherein
R1a is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, NHSO2- Ci-C4-alkyl, (C=0)-Ci-C4-alkyl, C(=0)-Ci-C4-alkoxy or Ci-C6-alkylsulfonyl;
R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy);
or R1 and R2 together with the nitrogen atom to which they are bound form a saturated or
partially unsaturated monocyclic 5- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 or 2 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle are replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein; particularly R1a is halogen or Ci-C6-alkyl;
R3, R4 independently of each other are hydrogen, Ci-C4-alkyl or Ci-C4-haloalky;
or the N-oxides, or the agriculturally acceptable salts thereof.
In a further embodiment the invention relates to compounds (1.2), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.2), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (I.2), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (I.2), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.2), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.2), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (I.2), wherein A is (A.4). In another embodiment the invention relates to compounds (1.2), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein, and wherein R3 is hydrogen and R4 is hydrogen or CH3. In yet another embodiment the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.2), wherein A is (A.4), and wherein A is unsubstituted, and wherein R3 is hydrogen and wherein R4 is hydrogen or CH3. In one embodiment the present invention relates to compounds (1.3) of the formula I wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, C C6-alkyl, Ci-C6-alkoxy, d-C6-alkylthio,
Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein
Ra is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs- cycloalkyl;
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl;
R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(CrC6-alkoxy);
R3 is hydrogen;
R4 is hydrogen, Ci-C4-alkyl or Ci-C4-haloalky;
or the N-oxides, or the agriculturally acceptable salts thereof.
In a further embodiment the invention relates to compounds (1.3), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.3), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.3), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.3), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.3), wherein A is (A.4). In another embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein, and wherein R4 is hydrogen or CH3. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.3), wherein A is (A.4), and wherein A is unsubstituted, and wherein R4 is hydrogen or CH3.
In one embodiment the present invention relates to compounds (1.4) of the formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from
N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein RA is chlorine, fluorine or methyl;
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cs-Cs-cycloalkyl;
R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy);
R3 is hydrogen;
R4 is hydrogen or CH3;
or the N-oxides, or the agriculturally acceptable salts thereof.
In a further embodiment the invention relates to compounds (1.4), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.2), and wherein A is unsubstituted.
In another embodiment the invention relates to compounds (I.4), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (I.4), wherein A is (A.4). In a further embodiment the invention relates to compounds (1.4), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.4), wherein A is (A.4), and wherein A is unsubstituted.
In one embodiment the present invention relates to compounds (1.5) of the formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio,
Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or Cs-Ce-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein Ra is halogen, cyano, N02, OH, SH, NH2, d-C6-alkyl, C C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs- cycloalkyl;
R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated monocyclic 5- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 or 2 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle are replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein; particularly R1a is halogen or d-Ce-alkyl;
R3, R4 independently of each other are hydrogen, Ci-C4-alkyl or Ci-C4-haloalky;
or the N-oxides, or the agriculturally acceptable salts thereof. In a further embodiment the invention relates to compounds (1.5), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.5), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.5), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.5), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.5), wherein A is (A.4). In another embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein, and wherein R3 is hydrogen and R4 is hydrogen or CH3. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.5), wherein A is (A.4), and wherein A is unsubstituted, and wherein R3 is hydrogen and wherein R4 is hydrogen or CH3.
In one embodiment the present invention relates to compounds (1.6) of the formula I
wherein:
A is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio,
Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl or C3-C8-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein Ra is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or Cs-Cs- cycloalkyl;
R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated monocyclic 5- or 6-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 further heteroatom independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle are replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined or preferably defined herein; particularly R1a is halogen or d-Ce-alkyl;
R3 is hydrogen;
R4 is hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl; or the N-oxides, or the agriculturally acceptable salts thereof.
In a further embodiment the invention relates to compounds (1.6), wherein A is (A.2). In a further embodiment the invention relates to compounds (1.6), wherein A is (A.2), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.2), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.6), wherein A is (A.8). In a further embodiment the invention relates to compounds (1.6), wherein A is (A.8), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.8), and wherein A is unsubstituted. In another embodiment the invention relates to compounds (1.6), wherein A is (A.4). In another embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein R4 is hydrogen or CH3. In a further embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein. In a further embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is substituted by 1 group RA as defined or preferably defined herein, and wherein R4 is hydrogen or CH3. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is unsubstituted. In yet another embodiment the invention relates to compounds (1.6), wherein A is (A.4), and wherein A is unsubstituted, and wherein R4 is hydrogen or CH3.
According to one embodiment, th mpounds of the formula I.A
Figure imgf000023_0001
or to the use of the compounds of the formula I.A for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.B
Figure imgf000023_0002
or to the use of the compounds of the formula I.B for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.C
Figure imgf000023_0003
or to the use of the compounds of the formula I.C for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, th mpounds of the formula I.D
Figure imgf000024_0001
or to the use of the compounds of the formula I.D for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.E
Figure imgf000024_0002
or to the use of the compounds of the formula I.E for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, th mpounds of the formula I.F
Figure imgf000024_0003
or to the use of the compounds of the formula I.F for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.G
Figure imgf000024_0004
or to the use of the compounds of the formula I.G for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.H
Figure imgf000025_0001
I.H
or to the use of the compounds of the formula I.H for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, th mpounds of the formula I.I
Figure imgf000025_0002
or to the use of the compounds of the formula I.I for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
According to one embodiment, the present invention relates to compounds of the formula I.J or to the use of the compounds of the formula I.J for controlling phytopathogenic fungi. Here, the variables are as defined elsewhere herein for formula I, or as defined as being preferred for formula I.
Figure imgf000025_0003
I.J
According to one embodiment, the present invention relates to compounds of the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q, I.R or I.S or to the use of the compounds of the formula I.K, I.L, I.M, I.N, I.O, I.P, I.Q, I.R or I.S for controlling phytopathogenic fungi. Here, the variables R3 and R4 are as defined or preferably defined herein for formula I.
Figure imgf000025_0004
Figure imgf000026_0001
I.Q I.R I.S
Preference is given to the compounds I used according to the invention and to the compounds according to the invention compiled in Tables 1 to 10 below. With regard to the compounds according to the invention the exception as defined above will be considered. The groups mentioned for a substituent in the tables are furthermore per se, independently of the combination in which they are mentioned, a particularly preferred aspect of the substituent in question.
Table 1
Compounds of the formula I .A, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.A.A-1 to I.A.A-973). For example, compound I.A.A-3 is therefore to be construed as a compound of formula I. A, wherein the meaning of R1 and R2 is as defined in line A-3 of table A (R1 is hydrogen and R2 is ethyl).
Table 2
Compounds of the formula I.B, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.B.A-1 to I.B.A-973).
Table 3
Compounds of the formula I.C, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.C.A-1 to I.C.A-973)
Table 4
Compounds of the formula I.D, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.D.A-1 to I.D.A-973).
Table 5
Compounds of the formula I.E, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.E.A-1 to I.E.A-973).
Table 6
Compounds of the formula I.F, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.F.A-1 to I.F.A-973).
Table 7
Compounds of the formula I.G, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.G.A-1 to I.G.A-503).
Table 8
Compounds of the formula I.H, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.H.A-1 to I.H.A-973).
Table 9
Compounds of the formula I.I, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I. I.A-1 to I.I.A-973).
Table 10
Compounds of the formula I.J, in which R1 and R2 for each individual compound corresponds in each case to one line of Table A (I.J.A-1 to I.J.A-973).
Table A:
Figure imgf000026_0002
Figure imgf000027_0001
o R1 R2 No R1 R2
A- 105 H 2-methyl-3-F-phenyl A- 155 H 2-methyl-3-CI-phenyl
A- 106 H 2-methyl-4-F-phenyl A- 156 H 2-methyl-4-CI-phenyl
A- 107 H 2-methyl-5-F-phenyl A- 157 H 2-methyl-5-CI-phenyl
A- 108 H 3-methyl-4-F-phenyl A- 158 H 3-methyl-4-CI-phenyl
A- 109 H 2-F-3-CF3-phenyl A- 159 H 2-CI-3-CF3-phenyl
A-1 10 H 2-F-4-CF3-phenyl A- 160 H 2-CI-4-CF3-phenyl
A-1 1 1 H 2-F-5-CF3-phenyl A-161 H 2-CI-5-CF3-phenyl
A-1 12 H 2-F-6-CF3-phenyl A- 162 H 2-CI-6-CF3-phenyl
A-1 13 H 3-F-4-CF3-phenyl A- 163 H 3-CI-4-CF3-phenyl
A-1 14 H 3-F-5-CF3-phenyl A- 164 H 3-CI-5-CF3-phenyl
A-1 15 H 2-CF3-3-F-phenyl A- 165 H 2-CF3-3-CI-phenyl
A-1 16 H 2-CF3-4-F-phenyl A- 166 H 2-CF3-4-CI-phenyl
A-1 17 H 2-CF3-5-F-phenyl A- 167 H 2-CF3-5-CI-phenyl
A-1 18 H 3-CF3-4-F-phenyl A- 168 H 3-CF3-4-CI-phenyl
A-1 19 H 2-F-3-OMe-phenyl A- 169 H 2-CI-3-OMe-phenyl
A- 120 H 2-F-4-OMe-phenyl A- 170 H 2-CI-4-OMe-phenyl
A-121 H 2-F-5-OMe-phenyl A-171 H 2-CI-5-OMe-phenyl
A- 122 H 2-F-6-OMe-phenyl A- 172 H 2-CI-6-OMe-phenyl
A- 123 H 3-F-4-OMe-phenyl A- 173 H 3-CI-4-OMe-phenyl
A- 124 H 3-F-5-OMe-phenyl A- 174 H 3-CI-5-OMe-phenyl
A- 125 H 2-OMe-3-F-phenyl A- 175 H 2-OMe-3-CI-phenyl
A- 126 H 2-OMe-4-F-phenyl A- 176 H 2-OMe-4-CI-phenyl
A- 127 H 2-OMe-5-F-phenyl A- 177 H 2-OMe-5-CI-phenyl
A- 128 H 3-OMe-4-F-phenyl A- 178 H 3-OMe-4-CI-phenyl
A- 129 H 2-F-3-OCHF2-phenyl A- 179 H 2-CI-3-OCHF2-phenyl
A- 130 H 2-F-4-OCHF2-phenyl A- 180 H 2-CI-4-OCHF2-phenyl
A-131 H 2-F-5-OCHF2-phenyl A-181 H 2-CI-5-OCHF2-phenyl
A- 132 H 2-F-6-OCHF2-phenyl A- 182 H 2-CI-6-OCHF2-phenyl
A- 133 H 3-F-4-OCHF2-phenyl A- 183 H 3-CI-4-OCHF2-phenyl
A- 134 H 3-F-5-OCHF2-phenyl A- 184 H 3-CI-5-OCHF2-phenyl
A- 135 H 2-OCHF2-3-F-phenyl A- 185 H 2-OCHF2-3-CI-phenyl
A- 136 H 2-OCHF2-4-F-phenyl A- 186 H 2-OCHF2-4-CI-phenyl
A- 137 H 2-OCHF2-5-F-phenyl A- 187 H 2-OCHF2-5-CI-phenyl
A- 138 H 3-OCHF2-4-F-phenyl A- 188 H 3-OCHF2-4-CI-phenyl
A- 139 H 2-F-3-CN-phenyl A- 189 H 2-CI-3-CN-phenyl
A- 140 H 2-F-4-CN-phenyl A- 190 H 2-CI-4-CN-phenyl
A-141 H 2-F-5-CN-phenyl A-191 H 2-CI-5-CN-phenyl
A- 142 H 2-F-6-CN-phenyl A- 192 H 2-CI-6-CN-phenyl
A- 143 H 3-F-4-CN-phenyl A- 193 H 3-CI-4-CN-phenyl
A- 144 H 3-F-5-CN-phenyl A- 194 H 3-CI-5-CN-phenyl
A- 145 H 2-CN-3-F-phenyl A- 195 H 2-CN-3-CI-phenyl
A- 146 H 2-CN-4-F-phenyl A- 196 H 2-CN-4-CI-phenyl
A- 147 H 2-CN-5-F-phenyl A- 197 H 2-CN-5-CI-phenyl
A- 148 H 3-CN-4-F-phenyl A- 198 H 3-CN-4-CI-phenyl
A- 149 H 2-CI-3-methyl-phenyl A- 199 H CH2-cyclopropyl
A- 150 H 2-CI-4-methyl-phenyl A-200 H CH2-cyclopentyl
A-151 H 2-CI-5-methyl-phenyl A-201 H CH2-cyclohexyl
A- 152 H 2-CI-6-methyl-phenyl A-202 H CH2-(4-quinolinyl)
A- 153 H 3-CI-4-methyl-phenyl A-203 H CH2-(2-pyridyl)
A- 154 H 3-CI-5-methyl-phenyl A-204 H CH2-(3-pyridyl)
Figure imgf000029_0001
o R1 R2 No R1 R2
A-295 CH3 4-pyridyl A-345 CH3 3-F-5-CI-phenyl
A-296 CH3 2-F-phenyl A-346 CH3 2-CI-3-F-phenyl
A-297 CH3 3-F-phenyl A-347 CH3 2-CI-4-F-phenyl
A-298 CH3 4-F-phenyl A-348 CH3 2-CI-5-F-phenyl
A-299 CH3 2-CI-phenyl A-349 CH3 3-CI-4-F-phenyl
A-300 CH3 3-CI-phenyl A-350 CH3 2-F-3-methyl-phenyl
A-301 CH3 4-CI-phenyl A-351 CH3 2-F-4-methyl-phenyl
A-302 CH3 2-methyl-phenyl A-352 CH3 2-F-5-methyl-phenyl
A-303 CH3 3-methyl-phenyl A-353 CH3 2-F-6-methyl-phenyl
A-304 CH3 4-methyl-phenyl A-354 CH3 3-F-4-methyl-phenyl
A-305 CH3 2-ethyl-phenyl A-355 CH3 3-F-5-methyl-phenyl
A-306 CH3 3-ethyl-phenyl A-356 CH3 2-methyl-3-F-phenyl
A-307 CH3 4-ethyl-phenyl A-357 CH3 2-methyl-4-F-phenyl
A-308 CH3 2-isopropyl-phenyl A-358 CH3 2-methyl-5-F-phenyl
A-309 CH3 3-isopropyl-phenyl A-359 CH3 3-methyl-4-F-phenyl
A-310 CH3 4-isopropyl-phenyl A-360 CH3 2-F-3-CF3-phenyl
A-31 1 CH3 2-(2,2,2-trifluoroethyl)-phenyl A-361 CH3 2-F-4-CF3-phenyl
A-312 CH3 3-(2,2,2-trifluoroethyl)-phenyl A-362 CH3 2-F-5-CF3-phenyl
A-313 CH3 4-(2,2,2-trifluoroethyl)-phenyl A-363 CH3 2-F-6-CF3-phenyl
A-314 CH3 2-trifluoromethyl-phenyl A-364 CH3 3-F-4-CF3-phenyl
A-315 CH3 3-trifluoromethyl-phenyl A-365 CH3 3-F-5-CF3-phenyl
A-316 CH3 4-trifluoromethyl-phenyl A-366 CH3 2-CF3-3-F-phenyl
A-317 CH3 2-methoxy-phenyl A-367 CH3 2-CF3-4-F-phenyl
A-318 CH3 3-methoxy-phenyl A-368 CH3 2-CF3-5-F-phenyl
A-319 CH3 4-methoxy-phenyl A-369 CH3 3-CF3-4-F-phenyl
A-320 CH3 2-trifluoromethoxy-phenyl A-370 CH3 2-F-3-OMe-phenyl
A-321 CH3 3-trifluoromethoxy-phenyl A-371 CH3 2-F-4-OMe-phenyl
A-322 CH3 4-trifluoromethoxy-phenyl A-372 CH3 2-F-5-OMe-phenyl
A-323 CH3 2-difluoromethoxy-phenyl A-373 CH3 2-F-6-OMe-phenyl
A-324 CH3 3-difluoromethoxy-phenyl A-374 CH3 3-F-4-OMe-phenyl
A-325 CH3 4-difluoromethoxy-phenyl A-375 CH3 3-F-5-OMe-phenyl
A-326 CH3 2-(2,2,2-trifluoroethoxy)-phenyl A-376 CH3 2-OMe-3-F-phenyl
A-327 CH3 3-(2,2,2-trifluoroethoxy)-phenyl A-377 CH3 2-OMe-4-F-phenyl
A-328 CH3 4-(2,2,2-trifluoroethoxy)-phenyl A-378 CH3 2-OMe-5-F-phenyl
A-329 CH3 2-cyano-phenyl A-379 CH3 3-OMe-4-F-phenyl
A-330 CH3 3-cyano-phenyl A-380 CH3 2-F-3-OCHF2-phenyl
A-331 CH3 4-cyano-phenyl A-381 CH3 2-F-4-OCHF2-phenyl
A-332 CH3 2,3-difluoro-phenyl A-382 CH3 2-F-5-OCHF2-phenyl
A-333 CH3 2,4-difluoro-phenyl A-383 CH3 2-F-6-OCHF2-phenyl
A-334 CH3 2,5-difluoro-phenyl A-384 CH3 3-F-4-OCHF2-phenyl
A-335 CH3 2,6-difluoro-phenyl A-385 CH3 3-F-5-OCHF2-phenyl
A-336 CH3 2,3-dichloro-phenyl A-386 CH3 2-OCHF2-3-F-phenyl
A-337 CH3 2,4-dichloro-phenyl A-387 CH3 2-OCHF2-4-F-phenyl
A-338 CH3 2,5-dichloro-phenyl A-388 CH3 2-OCHF2-5-F-phenyl
A-339 CH3 2,6-dichloro-phenyl A-389 CH3 3-OCHF2-4-F-phenyl
A-340 CH3 2-F-3-CI-phenyl A-390 CH3 2-F-3-CN-phenyl
A-341 CH3 2-F-4-CI-phenyl A-391 CH3 2-F-4-CN-phenyl
A-342 CH3 2-F-5-CI-phenyl A-392 CH3 2-F-5-CN-phenyl
A-343 CH3 2-F-6-CI-phenyl A-393 CH3 2-F-6-CN-phenyl
A-344 CH3 3-F-4-CI-phenyl A-394 CH3 3-F-4-CN-phenyl
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
The compounds of the formula I can be prepared according to methods or in analogy to methods that are described in the prior art. The synthesis takes advantage of starting materials that are commercially available or may be prepared according to conventional procedures starting from readily available compounds. For example, compounds of the formula I can be prepared by reacting amidines of type II with trifluoroacetic anhydride in an organic solvent, preferably an ethereal solvent at temperatures between 0 °C and 100 °C, preferably at room temperature, as previously described in WO2013/008162.
H
Figure imgf000037_0001
A skilled person will recognize that compounds of type II can be accessed by treating nitriles of type III with hydroxylamine (or its HCI salt) in an organic solvent and in the presence of a base (for precedents see for example WO2009/074950, WO2006/013104, EP1932843).
Figure imgf000037_0002
Compounds III can be prepared by reacting carbonyl compound of type IV with the respective amine in an organic solvent and in the presence of a base, followed by subsequent treatment of the intermediary iminium species V with an organometallic reagent or hydride (if R4 = H). If appropriate, the iminium species V may be isolated. The reaction is performed preferably in an ethereal solvent and at temperatures between -78 °C and 40 °C, more preferably at -15°C or at room temperature as previously described (see for example Tetrahedron Letters 52(2), 281 - 284, 201 1 or Journal of Organic Chemistry, 70(5), 1930-1933, 2005).
Figure imgf000037_0003
Compounds IV are either commercially available or can be accessed through known methods that are obvious for a person skilled in the art.
The compounds of the formula I or compositions comprising said compounds according to the invention and the mixtures comprising said compounds and compositions, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the following classes or are closely related to any of them: Ascomycota (Ascomycetes), for example, but not limited to the genus Cocholiobolus, Colletotrichum, Fusarium, Microdochium, Penicillium, Phoma, Magnaporte, Zymoseptoria, and Pseudocercosporella; Basdiomycota
(Basidiomycetes), for example, but not limited to the genus Phakospora, Puccinia, Rhizoctonia, Sphacelotheca, Tilletia, Typhula, and Ustilago; Chytridiomycota (Chytridiomycetes), for example, but not limited to the genus Chytridiales, and Synchytrium; Deuteromycetes (syn. Fungi imperfect!), for example, but not limited to the genus Ascochyta, Diplodia, Erysiphe, Fusarium, Phomopsis, and Pyrenophora; Peronosporomycetes (syn. Oomycetes), for example but not limited to the genus Peronospora, Pythium, Phytophthora; Plasmodiophoromycetes, for example but not limited to the genus Plasmodiophora; Zygomycetes, for example, but not limited to the genus Rhizopus.
Some of the compounds of the formula I and the compositions according to the invention are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g.
potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are
commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate- tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors);
stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cry1 Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas
Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amyivora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassico/a or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solan/ or A.
alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. /r/fa?/ (anthracnose) on wheat and A. horde/ on barley; Bipolar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicoia) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana. grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms;
Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchit) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum. leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus
(anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H.
oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C.
gossyp/ή, corn (e. g. C. graminico/a: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.
coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicoia (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C liriodendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans;
Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis. tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),
Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyn), soft fruits (E. veneta: anthracnose) and vines (E. ampe/ina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets {E. betae), vegetables (e. g. E. pisl), such as cucurbits (e. g. E.
cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium
(teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. so/anl( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F.
brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G zeae) and rice (e. g. G fujikuroi. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G gossypiion cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochiioboius) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseo/ή (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco {P. tabacina) and soybeans (e. g. P. manshurica);
Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum);
Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.
megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad- leaved trees (e. g. P. ramorum. sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. ha/stediion sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat {P. graminis) and sugar beets {P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapes/a yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. hum/// on hop; Pseudopez/cu/a tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. . triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagio asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. bet/cola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus sto/on/fer (b\ack mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale;
Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fsiior S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker!) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph:
Leptosphaeria [syn. Phaeosphaer/a] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (p\um pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
(common bunt or stinking smut) on cereals, such as e. g. T. tritici {s n. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis. corn smut) and sugar cane; Venturis spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V dahliae on strawberries, rape, potatoes and tomatoes.
In a preferred embodiment the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. me/bom/ae (soybean rust) on soybeans. The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola pp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora pp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent
disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting. The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical
Monograph No. 2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and
Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g.
lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid
alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron
hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants). Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS) 10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I and 1-10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce
spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS) An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g.
hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1-10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1-50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders
(SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the
agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained. The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors: Inhibitors of complex III at Q0 site: azoxystrobin (A.1.1 ), coumeth- oxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1.8), kresoxim- methyl (A.1.9), mandestrobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1 .12), picoxy- strobin (A.1 .13), pyraclostrobin (A.1.14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1 .16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)- phenyl)-2-methoxyimino-N-methyl-acetamide (A.1 .18), pyribencarb (A.1.19),
triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2- [(1 ,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1 .22), 1 -[3- chloro-2-[[1-(4-chlorophenyl)-1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one
(A.1 .23), 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5- one (A.1 .24), 1 -[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetra- zol-5-one (A.1.25), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-rnethyl- tetrazol-5-one (A.1 .26), 1 -[2-f[1 -(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4- methyl-tetrazol-5-one (A.1.27), 1 -[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]- 4-methyl-tetrazol-5-one (A.1 .28), 1 -[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl}-4- methyl-tetrazol-5-one (A.1.29), 1 -[3-cyclopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]- methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.30), 1-[3-(difluoromethoxy)-2-[[2-methyl-4- (1-methylpyrazol-3-yl)phenoxyjmethyi]phenyl]-4-methyl-tetrazol-5-one (A.1.31 ), 1-methyl-4-[3- methyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyljtetrazol-5-one (A.1.32), 1- methyl-4-[3-methyl-2-f[1 -[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol- 5-one (A.1.33), (Z,2f)-5-[1 -(2l4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide (A.1.34), (Z;2£)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-/V,3- dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1 .37), 2-(ortho-((2,5- dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1 .38).
Inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6S R.8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), [2-[[(7R,8R,9S)-7-benzyl-9-methyl-8- (2-methylpropanoyloxy)-2,6-dioxo-1 ,5-dioxonan-3-yl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate (A.2.4), [(6S,7R,8R)-8-benzyl-3-[[4-methoxy-3-(propanoyloxy- methoxy)pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.5).
Inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), 3-(difluoromethyl)-N-methoxy- 1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide (A.3.17), N-[2-(3,4- difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), 3-(difluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethylindan- 4-yl)pyrazole-4-carboxamide (A.3.22), 3-(trifluoromethyl)-1-methyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide (A.3.23), 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide (A.3.24), 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide (A.3.25), 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.26), 3-(difluoromethyl)-1 ,5-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N-(7-fluoro-1 ,1 ,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4- carboxamide (A.3.28), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy- prop-2-enoate (A.3.30), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3- (difluoromethyl)-5 fluoro-1-methyl-pyrazole-4-carboxamide (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3- trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3- trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl- indan-4-yl)->pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 -dimethyl- indan^-ylJ-'pyridine-S-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3-propyl-indan- 4-yl)-,py-,ridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1 ,1-dimethyl-3-propyl-indan- 4-yl]""pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1 ,1 -dimethyl-indan-4- yl^pyridine-S-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4 yl]pyridine-3-carboxamide (A.3.39).
Other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12).
B) Sterol biosynthesis inhibitors (SBI fungicides)
C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromuconazole (B.1 .3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1.6), diniconazole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusilazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1 .15), metconazole (B.1 .17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1 .20), penconazole (B.1.21 ), propiconazole (B.1 .22), prothioconazole (B.1.23), simeconazole (B.1 .24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1 .28), triticonazole (B.1.29), uniconazole (B.1 .30), 1 -[ A(2S;3 )-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H-[1 ,2,4]triazole (B.1 .31 ), 2-[re^2S, >R)- >-{2- chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1 ,2,4]triazole-3-thiol (B.1.32), 2-[2- chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)pentan-2-ol (B.1.33), 1-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1 ,2,4-triazol-1 -yl)ethanol (B.1.34), 2- [4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 ,2,4-triazol-1-yl)butan-2-ol (B.1 .35), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1 .36), 2-[4-(4-chloro- phenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1.37), 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.38), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-3-methyl-1 -(1 ,2,4-triazol-1 -yl)butan-2-ol (B.1 .39), 2-[4-(4- chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)pentan-2-ol (B.1 .40), 2-[4-(4- fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1 -yl)propan-2-ol (B.1 .41 ), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4-triazol-1 -yl)pent-3-yn-2-ol (B.1 .42), 2-(chloromethyl)-2- methyl-5-(p-tolylmethyl)-1 -(1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1 .45), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1 .50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro- phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1 .52). Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8).
Inhibitors of 3-keto reductase: fenhexamid (B.3.1 ).
Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 ).
C) Nucleic acid synthesis inhibitors
Phenylamides or acyl amino acid fungicides: benalaxyl (C.1 .1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1.6), oxadixyl (C.1.7).
Other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8).
D) Inhibitors of cell division and cytoskeleton
Tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1.2), fuberidazole (D1 .3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyrida- zine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N-ethyl-2- [(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2- fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2- methoxy-acetamide (D.1.1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide
(D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1 .13), 2-[(3- ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8- methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4- fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1 .16).
Other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7).
E) Inhibitors of amino acid and protein synthesis
Methionine synthesis inhibitors: cyprodinil (E.1.1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3). Protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin
hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6).
F) Signal transduction inhibitors
MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1 .4), fludioxonil (F.1.5).
G protein inhibitors: quinoxyfen (F.2.1 ).
G) Lipid and membrane synthesis inhibitors
Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1 .3), isoprothiolane (G.1 .4).
Lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7).
Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7).
Compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 ).
Inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1-{[3,5-bis(difluoromethyl- 1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1 - [2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2- carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 - yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1- yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1 -[2-[5-cyclopropyl-3- (difluoromethyl)pyrazol-l -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.7), 4- [1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4- piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.9), 4-[1 -[2-[3,5-bis(trifluoromethyl)pyrazol- 1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl- 3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide
(G.5.1 1 ).
H) Inhibitors with Multi Site Action
Inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1 .2), copper acetate (H.1 .3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7).
Thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9).
Organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan
(H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 ).
Guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10).
I) Cell wall synthesis inhibitors
Inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1.2).
Melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5).
J) Plant defence inducers
Acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1 .3), tiadinil (J.1 .4), prohexadione- calcium (J.1.5); phosphonates: fosetyl (J.1 .6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4- dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10).
K) Unknown mode of action
Bronopol (K.1 .1 ), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1 .4), dazomet (K.1 .5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1.9), di- fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1 .1 1 ), fenitropan (K.1 .12), fenpyrazamine (K.1 .13), flumetover (K.1 .14), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1.18), nitrapyrin (K.1 .19), nitrothal-isopropyl (K.1 .20), tolprocarb (K.1 .21 ), oxin- copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1 .24), tecloftalam (K.1.25), triazoxide (K.1 .26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1 .27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N- methyl formamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]oxy]-2,5- dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-
3- pyridyl)-N-ethyl-N-methyl-formamidine (K.1 .30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]- 2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31 ), N'-[5-bromo-6-(4- isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-
2- methyl-6-(1 -phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1 .33), N'-(2-methyl-5- trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1 .34), N'- (5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1 .35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy- acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1.38), 5-chloro-1-(4,6- dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1 .39), ethyl (Z)-3-amino-2-cyano-3- phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1- methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1 .43), 2-[2- [(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8- fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1 .45), 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-1 -yl)quinoline (K.1 .46), quinofumelin (K.1 .47), 3-(4,4,5-trifluoro-3,3-dimethyl- 3,4-dihydroisoquinolin-1-yl)quinoline (K.1 .48), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-
3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-
4- methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51 ), 3-[(3,4-dichloroisothiazol-
5- yl)methoxy]-1 ,2-benzothiazole 1 ,1-dioxide (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N- ethyl-N-methyl-formamidine (K.1 .53).
M) Growth regulators
abscisic acid (M.1 .1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim (N.1 .1 ), alloxydim-sodium (N.1.2), butroxydim (N.1.3), clethodim (N.1.4), clodinafop (N.1 .5), clodinafop-propargyl (N.1.6), cycloxydim (N.1.7), cyhalofop (N.1 .8), cyhalofop-butyl (N.1.9), diclofop(N.1 .10), diclofop-methyl (N.1.1 1 ), fenoxaprop (N.1 .12), fenoxaprop-ethyl (N.1 .13), fenoxaprop-P (N.1 .14), fenoxaprop-P-ethyl (N.1.15), fluazifop (N.1 .16), fluazifop-butyl (N.1 .17), fluazifop-P (N.1.18), fluazifop-P-butyl (N.1.19), haloxyfop (N.1.20), haloxyfop-methyl (N.1 .21 ), haloxyfop-P (N.1.22), haloxyfop-P- methyl (N.1 .23), metamifop (N.1 .24), pinoxaden (N.1 .25), profoxydim (N.1 .26), propaquizafop (N.1.27), quizalofop (N.1 .28), quizalofop-ethyl (N.1.29), quizalofop-tefuryl (N.1.30), quizalofop-P (N.1.31 ), quizalofop-P-ethyl (N.1 .32), quizalofop-P-tefuryl (N.1.33), sethoxydim (N.1 .34), tepraloxydim (N.1 .35), tralkoxydim (N.1.36), 4-(4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-
3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one ((N.1 .37) CAS 1312337-72-6); 4-(2',4'- dichloro-4-cyclopropyl[1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one ((N.1.38) CAS 1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one ((N.1.39) CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione ((N.1.40) CAS
1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro- 2,2,6,6-tetramethyl-2H-pyran-3-one ((N.1.41 ) CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'- dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (N.1.42); 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one ((N.1 .43) CAS 1312340-82-1 ); 5-(acetyloxy)-4-(2',4'-dichloro-4- ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one ((N.1.44) CAS
1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester ((N.1.45) CAS 1312337-51 -1 ); 4- (2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H- pyran-3-yl carbonic acid methyl ester (N.1.46); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)- 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester ((N.1 .47) CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5- oxo-2H-pyran-3-yl carbonic acid methyl ester ((N.1.48) CAS 1033760-58-5); benfuresate (N.1.49), butylate (N.1 .50), cycloate (N.1 .51 ), dalapon (N.1 .52), dimepiperate (N.1.53), EPTC (N.1.54), esprocarb (N.1 .55), ethofumesate (N.1 .56), flupropanate (N.1 .57), molinate (N.1.58), orbencarb (N.1 .59), pebulate (N.1.60), prosulfocarb (N.1.61 ), TCA (N.1.62), thiobencarb (N.1.63), tiocarbazil (N.1.64), triallate (N.1.65) and vernolate (N.1 .66);
N.2 ALS inhibitors: amidosulfuron (N.2.1 ), azimsulfuron (N.2.2), bensulfuron (N.2.3), bensul- furon-methyl (N.2.4), chlorimuron (N.2.5), chlorimuron-ethyl (N.2.6), chlorsulfuron (N.2.7), cinosulfuron (N.2.8), cyclosulfamuron (N.2.9), ethametsulfuron (N.2.10), ethametsulfuron- methyl (N.2.1 1 ), ethoxysulfuron (N.2.12), flazasulfuron (N.2.13), flucetosulfuron (N.2.14), flupyrsulfuron (N.2.15), flupyrsulfuron-methyl-sodium (N.2.16), foramsulfuron (N.2.17), halosulfuron (N.2.18), halosulfuron-methyl (N.2.19), imazosulfuron (N.2.20), iodosulfuron (N.2.21 ), iodosulfuron-methyl-sodium (N.2.22), iofensulfuron (N.2.23), iofensulfuron-sodium (N.2.24), mesosulfuron (N.2.25), metazosulfuron (N.2.26), metsulfuron (N.2.27), metsulfuron- methyl (N.2.28), nicosulfuron (N.2.29), orthosulfamuron (N.2.30), oxasulfuron (N.2.31 ), primisulfuron (N.2.32), primisulfuron-methyl (N.2.33), propyrisulfuron (N.2.34), prosulfuron (N.2.35), pyrazosulfuron (N.2.36), pyrazosulfuron-ethyl (N.2.37), rimsulfuron (N.2.38), sulfometuron (N.2.39), sulfometuron-methyl (N.2.40), sulfosulfuron (N.2.41 ), thifensulfuron (N.2.42), thifensulfuron-methyl (N.2.43), triasulfuron (N.2.44), tribenuron (N.2.45), tribenuron- methyl (N.2.46), trifloxysulfuron (N.2.47), triflusulfuron (N.2.48), triflusulfuron-methyl (N.2.49), tritosulfuron (N.2.50), imazamethabenz (N.2.51 ), imazamethabenz-methyl (N.2.52), imazamox (N.2.53), imazapic (N.2.54), imazapyr (N.2.55), imazaquin (N.2.56), imazethapyr (N.2.57); cloransulam (N.2.58), cloransulam-methyl (N.2.59), diclosulam (N.2.60), flumetsulam (N.2.61 ), florasulam (N.2.62), metosulam (N.2.63), penoxsulam (N.2.64), pyrimisulfan (N.2.65) and pyroxsulam (N.2.66); bispyribac (N.2.67), bispyribac-sodium (N.2.68), pyribenzoxim (N.2.69), pyriftalid (N.2.70), pyriminobac (N.2.71 ), pyriminobac-methyl (N.2.72), pyrithiobac (N.2.73), pyrithiobac-sodium (N.2.74), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid-1 -methyhethyl ester ((N.2.75) CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]^methyl]amino]-benzoic acid propyl ester ((N.2.76) CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine ((N.2.77) CAS 420138-01 -8); flucarbazone (N.2.78), flucarbazone-sodium (N.2.79), propoxycarbazone
(N.2.80), propoxycarbazone-sodium (N.2.81 ), thiencarbazone (N.2.82), thiencarbazone-methyl (N.2.83), triafamone (N.2.84);
N.3 Photosynthesis inhibitors: amicarbazone (N.3.1 ); chlorotriazine (N.3.2); ametryn (N.3.3), atrazine (N.3.4), chloridazone (N.3.5), cyanazine (N.3.6), desmetryn (N.3.7), dimethametryn (N.3.8),hexazinone (N.3.9), metribuzin (N.3.10), prometon (N.3.1 1 ), prometryn (N.3.12), pro- pazine (N.3.13), simazine (N.3.14), simetryn (N.3.15), terbumeton (N.3.16), terbuthylazin
(N.3.17), terbutryn (N.3.18), trietazin (N.3.19); chlorobromuron (N.3.20), chlorotoluron (N.3.21 ), chloroxuron (N.3.22), dimefuron (N.3.23), diuron (N.3.24), fluometuron (N.3.25), isoproturon (N.3.26), isouron (N.3.27), linuron (N.3.28), metamitron (N.3.29), methabenzthiazuron (N.3.30), metobenzuron (N.3.31 ), metoxuron (N.3.32), monolinuron (N.3.33), neburon (N.3.34), siduron (N.3.35), tebuthiuron (N.3.36), thiadiazuron (N.3.37), desmedipham (N.3.38), karbutilat (N.3.39), phenmedipham (N.3.40), phenmedipham-ethyl (N.3.41 ), bromofenoxim (N.3.42), bromoxynil (N.3.43) and its salts and esters, ioxynil (N.3.44) and its salts and esters, bromacil (N.3.45), lenacil (N.3.46), terbacil (N.3.47), bentazon (N.3.48), bentazon-sodium (N.3.49), pyridate (N.3.50), pyridafol (N.3.51 ), pentanochlor (N.3.52), propanil (N.3.53); diquat (N.3.54), diquat- dibromide (N.3.55), paraquat (N.3.56), paraquat-dichloride (N.3.57), paraquat-dimetilsulfate (N.3.58);
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen (N.4.1 ), acifluorfen-sodium (N.4.2), azafenidin (N.4.3), bencarbazone (N.4.4), benzfendizone (N.4.5), bifenox (N.4.6), butafenacil (N.4.7), carfentrazone (N.4.8), carfentrazone-ethyl (N.4.9), chlormethoxyfen (N.4.10), cinidon- ethyl (N.4.1 1 ), fluazolate (N.4.12), flufenpyr (N.4.13), flufenpyr-ethyl (N.4.14), flumiclorac (N.4.15), flumiclorac-pentyl (N.4.16), flumioxazin (N.4.17), fluoroglycofen (N.4.18),
fluoroglycofen-ethyl (N.4.19), fluthiacet (N.4.20), fluthiacet-methyl (N.4.21 ), fomesafen (N.4.22), halosafen (N.4.23), lactofen (N.4.24), oxadiargyl (N.4.25), oxadiazon (N.4.26), oxyfluorfen (N.4.27), pentoxazone (N.4.28), profluazol (N.4.29), pyraclonil (N.4.30), pyraflufen (N.4.31 ), pyraflufen-ethyl (N.4.32), saflufenacil (N.4.33), sulfentrazone (N.4.34), thidiazimin (N.4.35), tiafenacil (N.4.36), trifludimoxazin (N.4.37), ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate
((N.4.38) CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoro-methylphenoxy)-5-methyl-1 H- pyrazole-1-carboxamide ((N.4.39) CAS 452098-92-9), N tetrahydrofurfuryl-3-(2,6-dichloro-4- trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide ((N.4.40) CAS 915396-43-9), N- ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide ((N.4.41 ) CAS 452099-05-7), N tetrahydro->furfuryl-3-(2-chloro-6-fluoro-4- tnfluoro-"methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide ((N.4.42) CAS 452100-03-7), 3- [7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione ((N.4.43) CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl- 3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione ((N.4.44) CAS 13001 18-96-0), 1-methyl-6-trifluoro->methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro- 2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione ((N.4.45) CAS 13041 13-05-0), methyl (E)-4- [2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy- but-2-enoate ((N.4.46) CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H- benzimidazol-4-yl]-1 -methyl-6-(trifluoromethyl)-1 H-pyrimid ((N.4.47) CAS 212754-
02-4);
N.5 Bleacher herbicides: beflubutamid (N.5.1 ), diflufenican (N.5.2), fluridone (N.5.3), flurochloridone (N.5.4), flurtamone (N.5.5), norflurazon (N.5.6), picolinafen (N.5.7), 4-(3- trifluoromethyl^phenoxy)-2-(4-trifluoromethylphenyl)->pyrimidine ((N.5.8) CAS 180608-33-7); benzobicyclon (N.5.9), benzofenap (N.5.10), bicyclopyrone (N.5.1 1 ), clomazone (N.5.12), fenquintrione (N.5.13), isoxaflutole (N.5.14), mesotrione (N.5.15), pyrasulfotole (N.5.16), pyrazolynate (N.5.17), pyrazoxyfen (N.5.18), sulcotrione (N.5.19), tefuryltrione (N.5.20), tembotrione (N.5.21 ), tolpyralate (N.5.22), topramezone (N.5.23); aclonifen (N.5.24), amitrole (N.5.25), flumeturon (N.5.26);
N.6 EPSP synthase inhibitors: glyphosate (N.6.1 ), glyphosate-isopropylammonium (N.6.2), glyposate-potassium (N.6.3), glyphosate-trimesium (sulfosate) (N.6.4);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos) (N.7.1 ), bilanaphos-sodium (N.7.2), glufosinate (N.7.3), glufosinate-P (N.7.4), glufosinate-ammonium (N.7.5);
N.8 DHP synthase inhibitors: asulam (N.8.1 );
N.9 Mitosis inhibitors: benfluralin (N.9.1 ), butralin (N.9.2), dinitramine (N.9.3), ethalfluralin (N.9.4), fluchloralin (N.9.5), oryzalin (N.9.6), pendimethalin (N.9.7), prodiamine (N.9.8), trifluralin (N.9.9); amiprophos (N.9.10), amiprophos-methyl (N.9.1 1 ), butamiphos (N.9.12); chlorthal (N.9.13), chlorthal-dimethyl (N.9.14), dithiopyr (N.9.15), thiazopyr (N.9.16), propyzamide
(N.9.17), tebutam (N.9.18); carbetamide (N.9.19), chlorpropham (N.9.20), flamprop (N.9.21 ), flamprop-isopropyl (N.9.22), flamprop-methyl (N.9.23), flamprop-M-isopropyl (N.9.24), flamprop- M-methyl (N.9.25), propham (N.9.26);
N.10 VLCFA inhibitors: acetochlor (N.10.1 ), alachlor (N.10.2), butachlor (N.10.3), dimethachlor (N.10.4), dimethenamid (N.10.5), dimethenamid-P (N.10.6), metazachlor (N.10.7), metolachlor (N.10.8), metolachlor-S (N.10.9), pethoxamid (N.10.10), pretilachlor (N.10.1 1 ), propachlor (N.10.12), propisochlor (N.10.13), thenylchlor (N.10.14), flufenacet (N.10.15), mefenacet (N.10.16), diphenamid (N.10.17), naproanilide (N.10.18), napropamide (N.10.19), napropamide- M (N.10.20), fentrazamide (N.10.21 ), anilofos (N.10.22), cafenstrole (N.10.23), fenoxasulfone (N.10.24), ipfencarbazone (N.10.25), piperophos (N.10.26), pyroxasulfone (N.10.27), i II.5, II.6, II.7, II.8 and II.9
Figure imgf000057_0001
11.1
II.2
Figure imgf000057_0002
II.3 II.4 II.5
Figure imgf000058_0001
11.6 11.7
Figure imgf000058_0002
N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid (N.1 1.1 ), dichlobenil (N.1 1 .2), flupoxam (N.1 1 .3), indaziflam (N.1 1 .4), isoxaben (N.1 1 .5), triaziflam (N.1 1.6), 1 -cyclohexyl-5- pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine ((N.1 1 .7) CAS 175899-01-1 );
N.12 Decoupler herbicides: dinoseb (N.12.1 ), dinoterb (N.12.2), DNOC (N.12.3) and its salts; N.13 Auxinic herbicides: 2,4-D (N.13.1 ) and its salts and esters, clacyfos (N.13.2), 2,4-DB (N.13.3) and its salts and esters, aminocyclopyrachlor (N.13.4) and its salts and esters, aminopyralid (N.13.5) and its salts such as aminopyralid-dimethylammonium (N.13.6), aminopyralid-tris(2-hydroxypropyl)ammonium (N.13.7) and its esters, benazolin (N.13.8), benazolin-ethyl (N.13.9), chloramben (N.13.10) and its salts and esters, clomeprop (N.13.1 1 ), clopyralid (N.13.12) and its salts and esters, dicamba (N.13.13) and its salts and esters, dichlorprop (N.13.14) and its salts and esters, dichlorprop-P (N.13.15) and its salts and esters, fluroxypyr (N.13.16), fluroxypyr-butometyl (N.13.17), fluroxypyr-meptyl (N.13.18), halauxifen (N.13.) and its salts and esters (CAS 943832-60-8); MCPA (N.13.) and its salts and esters, MCPA-thioethyl (N.13.19), MCPB (N.13.20) and its salts and esters, mecoprop (N.13.21 ) and its salts and esters, mecoprop-P (N.13.22) and its salts and esters, picloram (N.13.23) and its salts and esters, quinclorac (N.13.24), quinmerac (N.13.25), TBA (2,3,6) (N.13.26) and its salts and esters, triclopyr (N.13.27) and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-meth- oxyphenyl)-5-fluoropyridine-2-carboxylic acid (N.13.28), benzyl 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate ((N.13.29) CAS 1390661-72-9);
N.14 Auxin transport inhibitors: diflufenzopyr (N.14.1 ), diflufenzopyr-sodium (N.14.2), naptalam (N.14.3) and naptalam-sodium (N.14.4);
N.15 Other herbicides: bromobutide (N.15.1 ), chlorflurenol (N.15.2), chlorflurenol-methyl
(N.15.3), cinmethylin (N.15.4), cumyluron (N.15.5), cyclopyrimorate ((N.15.6) CAS 499223-49-3) and its salts and esters, dalapon (N.15.7), dazomet (N.15.8), difenzoquat (N.15.9), difenzoquat- metilsulfate (N.15.10), dimethipin (N.15.1 1 ), DSMA (N.15.12), dymron (N.15.13), endothal (N.15.14) and its salts, etobenzanid (N.15.15), flurenol (N.15.16), flurenol-butyl (N.15.17), flurprimidol (N.15.18), fosamine (N.15.19), fosamine-ammonium (N.15.20), indanofan (N.15.21 ), maleic hydrazide (N.15.22), mefluidide (N.15.23), metam (N.15.24), methiozolin ((N.15.25) CAS 403640-27-7), methyl azide (N.15.26), methyl bromide (N.15.27), methyl-dymron (N.15.28), methyl iodide (N.15.29), MSMA (N.15.30), oleic acid (N.15.31 ), oxaziclomefone (N.15.32), pelargonic acid (N.15.33), pyributicarb (N.15.34), quinoclamine (N.15.35), tridiphane (N.15.36); O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb (0.1.1 ), alanycarb (0.1 .2), bendiocarb (0.1 .3), benfuracarb (0.1.4), butocarboxim (0.1.5), butoxycarboxim (0.1 .6), carbaryl (0.1.7), carbofuran (0.1.8), carbosulfan (0.1 .9), ethiofencarb (0.1 .10), fenobucarb (0.1 .1 1 ),
formetanate (0.1 .12), furathiocarb (0.1.13), isoprocarb (0.1.14), methiocarb (0.1.15), methomyl (0.1 .16), metolcarb (0.1 .17), oxamyl (0.1 .18), pirimicarb (0.1.19), propoxur (0.1.20), thiodicarb (0.1 .21 ), thiofanox (0.1.22), trimethacarb (0.1.23), XMC (0.1 .24), xylylcarb (0.1.25) and triazamate (0.1.26); acephate (0.1 .27), azamethiphos (0.1 .28), azinphos-ethyl (0.1 .29), azinphosmethyl (0.1 .30), cadusafos (0.1 .31 ), chlorethoxyfos (0.1.32), chlorfenvinphos
(0.1 .33), chlormephos (0.1.34), chlorpyrifos (0.1 .35), chlorpyrifos-methyl (0.1 .36), coumaphos (0.1 .37), cyanophos (0.1 .38), demeton-S-methyl (0.1.39), diazinon (0.1 .40), dichlorvos/ DDVP (0.1 .41 ), dicrotophos (0.1 .42), dimethoate (0.1 .43), dimethylvinphos (0.1 .44), disulfoton (0.1 .45), EPN (0.1.46), ethion (0.1.47), ethoprophos (0.1.48), famphur (0.1.49), fenamiphos (0.1 .50), fenitrothion (0.1 .51 ), fenthion (0.1.52), fosthiazate (0.1.53), heptenophos (0.1.54), imicyafos (0.1.55), isofenphos (0.1.56), isopropyl O-(methoxyaminothio-phosphoryl) salicylate (0.1 .57), isoxathion (0.1.58), malathion (0.1.59), mecarbam (0.1.60), methamidophos
(0.1 .61 ), methidathion (0.1 .62), mevinphos (0.1 .63), monocrotophos (0.1.64), naled (0.1 .65), omethoate (0.1 .66), oxydemeton-methyl (0.1.67), parathion (0.1.68), parathion-methyl (0.1 .69), phenthoate (0.1.70), phorate (0.1 .71 ), phosalone (0.1 .72), phosmet (0.1 .73), phosphamidon (0.1 .74), phoxim (0.1 .75), pirimiphos- methyl (0.1 .76), profenofos (0.1.77), propetamphos (0.1.78), prothiofos (0.1 .79), pyraclofos (0.1 .80), pyridaphenthion (0.1.81 ), quinalphos (0.1 .82), sulfotep (0.1 .83), tebupirimfos (0.1 .84), temephos (0.1 .85), terbufos (0.1 .86), tetrachlorvinphos (0.1 .87), thiometon (0.1.88), triazophos (0.1.89), trichlorfon
(0.1 .90), vamidothion (0.1 .91 );
0.2 GABA-gated chloride channel antagonists: endosulfan (0.2.1 ), chlordane (0.2.2); ethiprole (0.2.3), fipronil (0.2.4), flufiprole (0.2.5), pyrafluprole (0.2.6), pyriprole (0.2.7);
0.3 Sodium channel modulators: acrinathrin (0.3.1 ), allethrin (0.3.2), d-cis-trans allethrin (0.3.3), d-trans allethrin (0.3.4), bifenthrin (0.3.5), bioallethrin (0.3.6), bioallethrin S- cylclopentenyl (0.3.7), bioresmethrin (0.3.8), cycloprothrin (0.3.9), cyfluthrin (0.3.10), beta- cyfluthrin (0.3.1 1 ), cyhalothrin (0.3.12), lambda-cyhalothrin (0.3.13), gamma-cyhalothrin (0.3.14), cypermethrin (0.3.15), alpha-cypermethrin (0.3.16), beta-cypermethrin (0.3.17), theta-cypermethrin (0.3.18), zeta-cypermethrin (0.3.19), cyphenothrin (0.3.20), deltamethrin (0.3.21 ), empenthrin (0.3.22), esfenvalerate (0.3.23), etofenprox (0.3.24), fenpropathrin (0.3.25), fenvalerate (0.3.26), flucythrinate (0.3.27), flumethrin (0.3.28), tau-fluvalinate
(0.3.29), halfenprox (0.3.30), heptafluthrin (0.3.31 ), imiprothrin (0.3.32), meperfluthrin
(0.3.33), metofluthrin (0.3.34), momfluorothrin (0.3.35), permethrin (0.3.36), phenothrin (0.3.37), prallethrin (0.3.38), profluthrin (0.3.39), pyrethrin (pyrethrum) (O.3.40), resmethrin (0.3.41 ), silafluofen (0.3.42), tefluthrin (0.3.43), tetramethylfluthrin (0.3.44), tetramethrin (0.3.45), tralomethrin (0.3.46) and transfluthrin (0.3.47); DDT (0.3.48), methoxychlor (0.3.49); 0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid (0.4.1 ), clothianidin (0.4.2), cycloxaprid (0.4.3), dinotefuran (0.4.4), imidacloprid (0.4.5), nitenpyram (0.4.6), thiacloprid (0.4.7), thiamethoxam (0.4.8); (2E)-1 -[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidene- hydrazinecarboximidamide (0.4.9); 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine (0.4.10); nicotine (0.4.1 1 ); 0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad (0.5.1 ), spinetoram (0.5.2); 0.6 Chloride channel activators: abamectin (0.6.1 ), emamectin benzoate (0.6.2), ivermectin (0.6.3), lepimectin (0.6.4), milbemectin (0.6.5);
0.7 Juvenile hormone mimics: hydroprene (0.7.1 ), kinoprene (0.7.2), methoprene (0.7.3); fenoxycarb (0.7.4), pyriproxyfen (0.7.5);
0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide (0.8.1 ) and other alkyl halides; chloropicrin (0.8.2), sulfuryl fluoride (0.8.3), borax (0.8.4), tartar emetic (0.8.5);
0.9 Selective homopteran feeding blockers: pymetrozine (0.9.1 ), flonicamid (0.9.2);
O.10 Mite growth inhibitors: clofentezine (O.10.1 ), hexythiazox (O.10.2), diflovidazin (O.10.3); etoxazole (0.10.4);
0.1 1 Microbial disruptors of insect midgut membranes: the Bt crop proteins: Cry1 Ab, Cry1 Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron (0.12.1 ); azocyclotin (0.12.2), cyhexatin (0.12.3), fenbutatin oxide (0.12.4), propargite (0.12.5), tetradifon (0.12.6);
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr (0.13.1 ), DNOC (0.13.2), sulfluramid (0.13.3);
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap (0.14.1 ), cartap hydrochloride (0.14.2), thiocyclam (0.14.3), thiosultap sodium (0.14.4);
0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron (0.15.1 ), chlorfluazuron (0.15.2), diflubenzuron (0.15.3), flucycloxuron (0.15.4), flufenoxuron (0.15.5), hexaflumuron (0.15.6), lufenuron (0.15.7), novaluron (0.15.8), noviflumuron (0.15.9), teflubenzuron (0.15.10), triflumuron (0.15.1 1 );
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin (0.16.1 );
0.17 Moulting disruptors: cyromazine (0.17.1 );
0.18 Ecdyson receptor agonists: methoxyfenozide (0.18.1 ), tebufenozide (0.18.2),
halofenozide (0.18.3), fufenozide (0.18.4), chromafenozide (0.18.5);
0.19 Octopamin receptor agonists: amitraz (0.19.1 );
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon (O.20.1 ), acequinocyl (O.20.2), fluacrypyrim (O.20.3);
0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin (0.21.1 ), fenpyroximate (0.21.2), pyrimidifen (0.21 .3), pyridaben (0.21.4), tebufenpyrad (0.21.5), tolfenpyrad (0.21.6); rotenone (0.21 .7);
0.22 Voltage-dependent sodium channel blockers: indoxacarb (0.22.1 ), metaflumizone (0.22.2), 2-[2-(4-cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide (0.22.3), N-(3-chloro-2-methylphenyl)-2-[(4- chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide (0.22.4);
0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen (0.23.1 ), spiromesifen (0.23.2), spirotetramat (0.23.3);
0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide (0.24.1 ), calcium phosphide (0.24.2), phosphine (0.24.3), zinc phosphide (0.24.4), cyanide (0.24.5); 0.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen (0.25.1 ), cyflumetofen (0.25.2);
0.26 Ryanodine receptor-modulators: flubendiamide (0.26.1 ), chlorantraniliprole (0.26.2), cyantraniliprole (0.26.3), cyclaniliprole (0.26.4), tetraniliprole (0.26.5); (R)-3-chloro-N1 -{2- methyl-4-[1 ,2,2,2 -tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 -methyl-2- methylsulfonylethyl)phthalamide (0.26.6), (S)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide (0.26.7), methyl- 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}amino)benzoyl]- 1 ,2-dimethylhydrazinecarboxylate (0.26.8); N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)- carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (0.26.9); N- [4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)- 5-(trifluoromethyl)pyrazole-3-carboxamide (0.26.10); N-[4-chloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide (0.26.1 1 ); N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide (0.26.12); N-[4,6-di- bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(tri- fluoromethyl)pyrazole-3-carboxamide (0.26.13); N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6- methylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide (0.26.14); 3-chloro- 1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1 H- pyrazole-5-carboxamide (0.26.15); 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5- dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide (0.26.16); N-[4-chloro-2-[[(1 ,1- dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H- pyrazole-5-carboxamide (0.26.17); cyhalodiamide (0.26.18);
0.27. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen (0.27.1 ), afoxolaner (0.27.2), azadirachtin (0.27.3), amidoflumet (0.27.4), benzoximate (0.27.5), bifenazate (0.27.6), broflanilide (0.27.7), bromopropylate (0.27.8), chinomethionat (0.27.9), cryolite (0.27.10), dicloromezotiaz (0.27.1 1 ), dicofol (0.27.12), flufenerim (0.27.13), flometoquin (0.27.14), fluensulfone (0.27.15), fluhexafon (0.27.16), fluopyram (0.27.17), flu pyradifu rone (0.27.18), fluralaner (0.27.19), metoxadiazone (0.27.20), piperonyl butoxide (0.27.21 ), pyflubumide (0.27.22), pyridalyl (0.27.23), pyrifluquinazon (0.27.24), sulfoxaflor (0.27.25), tioxazafen (0.27.26), triflumezopyrim (0.27.27), 1 1 -(4-chloro-2,6-dimethylphenyl)- 12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1-en-10-one (0.27.28), 3-(4'-fluoro-2,4- dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (0.27.28), 1 -[2-fluoro-4- methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4-triazole-5-amine (0.27.29), (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide (0.27.31 ); (E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide (0.27.32); (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridyli- dene]acetamide (0.27.33); (E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide (0.27.34); (E/Z)-N-[1 -[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide (0.27.35); (E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide (0.27.36); (E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2- difluoro-acetamide (0.27.37); (E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2- trifluoro-acetamide (0.27.38); (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3- pentafluoro-propanamide (0.27.39); N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2- trifluoro-thioacetamide (O.27.40); N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- N'-isopropyl-acetamidine (0.27.41 ); fluazaindolizine (0.27.42); 4-[5-(3,5-dichlorophenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide (0.27.43); fluxamet- amide (0.27.44); 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole (0.27.45); 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-l - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide (0.27.46); 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide (0.27.47); N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-meth
(0.27.48); N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide (0.27.49); 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoro- methyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide (0.27.50); 3-fluoro-N-[2-fluoro-3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluorom
carbonyl]phenyl]-N-methyl-benzamide (0.27.51 ); 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-l -
(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridi
(0.27.52); 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluorometh- yl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide (0.27.53); 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]-2-fluoro-benzamide (0.27.54); N-[5-[[2-chloro-6-cyano-4-[1 ,2,2,3,3,3-hexafluoro- 1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (0.27.55); N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(0.27.56); N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3, 3,3-hexafluoro-1-(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide (0.27.57); 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 , 2,2,3, 3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]- carbamoyl]phenyl]-2-methyl-benzamide (0.27.58); 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide (0.27.59); N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1 -
(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide
(O.27.60); 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3- pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine (0.27.61 ); 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2- pyridinyl]-pyrimidine (0.27.62); N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-car- boxamide (0.27.63); N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide (0.27.64); N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (0.27.65); N- methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (0.27.66); N,2-dimethyl- N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (0.27.67); N-ethyl-2-methyl-N- [4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide (0.27.68); N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide (0.2769.); N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide (0.27.70); N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide (0.27.71 ); N-[4-chloro-2-(3- pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide (0.27.72); 1 -[(6-chloro-3-pyri- dinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1 ,2-a]pyridine
(0.27.73); 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1 ,2,3,5, 6,7-hexahydroimidazo[1 ,2- a]pyridin-5-ol (0.27.74); 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.75); 1-(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide (0.27.76); N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide (0.27.77); 1-[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide (0.27.78); N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4- yl-pyrazole-4-carboxamide (0.27.79); 1-(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide (0.27.80); 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4- yl-pyrazole-4-carboxamide (0.27.81 ); N-methyl-1 -(2-fluoro-1-methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide (0.27.82); 1 -(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide (0.27.83); 1 -(4,4-difluorocyclohexyl)-N,5-dimethyl-N- pyridazin-4-yl-pyrazole-4-carboxamide (0.27.84), N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole- 4-carboxamide (0.27.85); N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide (0.27.86); N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide (0.27.87); 2-(3-pyridinyl)-N-(2,2,2- trifluoroethyl)-2H-indazole-4-carboxamide (0.27.88); 2-(3-pyridinyl)-N-[(tetrahydro-2- furanyl)methyl]-2H-indazole-5-carboxamide (0.27.89); methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate (0.27.90); N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide (0.27.91 ); N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide (0.27.92); 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide (0.27.93); N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide
(0.27.94), N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)- propanamide (0.27.95); N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfinyl)propanamide (0.27.96); N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-di- fluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide (0.27.97); N-[3-chloro-1-(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide (0.27.98); sarolaner (0.27.99), lotilaner (0.27.100).
The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ;
EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,
JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;
US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404;
WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ;
WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388;
WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325;
WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 1 1/028657, WO 12/168188,
WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303,
WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010,
WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177,
WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454,
WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ).
The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.
Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).
By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
In the binary mixtures and compositions according to the invention the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1 .
According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1 .
According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1 ) and the component 2) usually is in the range of from 1 :1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
In the ternary mixtures, i.e. compositions according to the invention comprising the component 1 ) and component 2) and a compound III (component 3), the weight ratio of component 1 ) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1.
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1 ).
These ratios are also suitable for inventive mixtures applied by seed treatment.
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q0 site in group A), more preferably selected from compounds (A.1.1 ), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1 .12), (A.1.13), (A.1 .14), (A.1.17), (A.1 .21 ), (A.1.24), (A.1.25), (A.1 .26), (A.1.27), (A.1 .30), (A.1.31 ), (A.1.32), (A.1 .34) and
(A.1 .35); particularly selected from (A.1.1 ), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1 .14), (A.1.17), (A.1 .24), (A.1.25), (A.1.26), (A.1 .27), (A.1.30), (A.1 .31 ), (A.1.32), (A.1 .34) and (A.1 .35).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from compounds (A.2.1 ), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.1 1 ), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21 ), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.28), (A.3.29), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39);
particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.29), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from
compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1 .1 1 ), (B.1.12), (B.1 .13), (B.1.17), (B.1 .18), (B.1 .21 ), (B.1.22), (B.1.23), (B.1 .25), (B.1.26), (B.1 .29), (B.1.34), (B.1 .37), (B.1.38), (B.1 .43) and (B.1 .46); particularly selected from (B.1.5), (B.1.8), (B.1 .10), (B.1.17), (B.1.22), (B.1.23), (B.1 .25), (B.1.33), (B.1 .34), (B.1.37), (B.138), (B.1.43) and (B.1.46).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta 14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1 ), (C.1 .2), (C.1.4) and (C.1.5); particularly selected from (C.1 .1 ) and (C.1.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1.5) and (D.2.6).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1 ), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5). Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1 ), (G.3.3), (G.3.6), (G.5.1 ), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.1 1 ); particularly selected from (G.3.1 ), (G.5.1 ), (G.5.2) and (G.5.3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (I.2.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1 .2), (J.1.5) and (J.1 .8); in particular (J.1.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41 ), (K.1 .42), (K.1.44), (K.1 .45), (K.1.47) and (K.1.49); particularly selected from (K.1 .41 ), (K.1.44), (K.1 .45), (K.1.47) and (K.1 .49). Accordingly, the present invention furthermore relates to mixtures comprising one compound of the formula I (component 1 ) and one pesticide II (component 2), wherein pesticide II is selected from the column "Co. 2" of the lines B-1 to B-727 of Table B.
A further embodiment relates to the mixtures B-1 to B-727 listed in Table B, where a row of Table B corresponds in each case to a fungicidal mixture comprising as active components one of the in the present specification individualized compounds of formula I, i.e. compounds I.A.A-1 to I.A.A-503, I.B.A-1 to I.B.A-503, I.C.A-1 to I.C.A-503, I.D.A-1 to I.D.A-503, I.E.A-1 to I.E.A-503, I.F.A-1 to I.F.A-503, I.G.A-1 to I.G.A-503, I.H.A-1 to I.H.A-503, I.I.A-1 to I.I.A-503 and I.J.A-1 to I.J.A-503 as defined in tables 1 to 1 1 (component 1 in column "Co.1 ") and the respective pesticide II from groups A) to O) (component 2) stated in the row in question.
Another embodiment relates to the mixtures B-1 to B-727 listed in Table B, where a row of
Table B corresponds in each case to a fungicidal mixture comprising as active components one of the compounds Ex-1 to Ex-7 of formula I as defined below in table I (component 1 in column "Co.1 ") and the respective pesticide II from groups A) to O) (component 2) stated in the row in question.
Preferably, the compositions described in Table B comprise the active components in synergistically effective amounts.
Table B: Mixtures comprising as active components one indiviualized compound of the fomula I (in column Co. 1 ), and as component 2) (in column Co. 2) one pesticide from groups A) to O) [which is coded e. g. as (A.1 .1 ) for azoxystrobin as defined above]. Mixt. Co.1 Co.2 Mixt. Co.1 Co.2 Mixt. Co.1 Co.2
B-1 (I) (A.1.1) B-43 (I) (A.3.6) B-85 (I) (A.4.9)
B-2 (I) (A.1.2) B-44 (I) (A.3.7) B-86 (I) (A.4.10)
B-3 (I) (A.1.3) B-45 (I) (A.3.8) B-87 (I) (A.4.11)
B-4 (I) (A.1.4) B-46 (I) (A.3.9) B-88 (I) (A.4.12)
B-5 (I) (A.1.5) B-47 (I) (A.3.10) B-89 (I) (B.1.1)
B-6 (I) (A.1.6) B-48 (I) (A.3.11) B-90 (I) (B.1.2)
B-7 (I) (A.1.7) B-49 (I) (A.3.12) B-91 (I) (B.1.3)
B-8 (I) (A.1.8) B-50 (I) (A.3.13) B-92 (I) (B.1.4)
B-9 (I) (A.1.9) B-51 (I) (A.3.14) B-93 (I) (B.1.5)
B-10 (I) (A.1.10) B-52 (I) (A.3.15) B-94 (I) (B.1.6)
B-11 (I) (A.1.11) B-53 (I) (A.3.16) B-95 (I) (B.1.7)
B-12 (I) (A.1.12) B-54 (I) (A.3.17) B-96 (I) (B.1.8)
B-13 (I) (A.1.13) B-55 (I) (A.3.18) B-97 (I) (B.1.9)
B-14 (I) (A.1.14) B-56 (I) (A.3.19) B-98 (I) (B.1.10)
B-15 (I) (A.1.15) B-57 (I) (A.3.20) B-99 (I) (B.1.11)
B-16 (I) (A.1.16) B-58 (I) (A.3.21) B-100 (I) (B.1.12)
B-17 (I) (A.1.17) B-59 (I) (A.3.22) B-101 (I) (B.1.13)
B-18 (I) (A.1.18) B-60 (I) (A.3.23) B-102 (I) (B.1.14)
B-19 (I) (A.1.19) B-61 (I) (A.3.24) B-103 (I) (B.1.15)
B-20 (I) (A.1.20) B-62 (I) (A.3.25) B-104 (I) (B.1.16)
B-21 (I) (A.1.21) B-63 (I) (A.3.26) B-105 (I) (B.1.17)
B-22 (I) (A.1.22) B-64 (I) (A.3.27) B-106 (I) (B.1.18)
B-23 (I) (A.1.23) B-65 (I) (A.3.28) B-107 (I) (B.1.19)
B-24 (I) (A.1.24) B-66 (I) (A.3.29) B-108 (I) (B.1.20)
B-25 (I) (A.1.25) B-67 (I) (A.3.30) B-109 (I) (B.1.21)
B-26 (I) (A.1.26) B-68 (I) (A.3.31) B-110 (I) (B.1.22)
B-27 (I) (A.1.27) B-69 (I) (A.3.32) B-111 (I) (B.1.23)
B-28 (I) (A.1.30) B-70 (I) (A.3.33) B-112 (I) (B.1.24)
B-29 (I) (A.1.31) B-71 (I) (A.3.34) B-113 (I) (B.1.25)
B-30 (I) (A.1.32) B-72 (I) (A.3.35) B-114 (I) (B.1.26)
B-31 (I) (A.2.1) B-73 (I) (A.3.36) B-115 (I) (B.1.27)
B-32 (I) (A.2.2) B-74 (I) (A.3.37) B-116 (I) (B.1.28)
B-33 (I) (A.2.3) B-75 (I) (A.3.38) B-117 (I) (B.1.29)
B-34 (I) (A.2.4) B-76 (I) (A.3.39) B-118 (I) (B.1.30)
B-35 (I) (A.2.6) B-77 (I) (A.4.1) B-119 (I) (B.1.34)
B-36 (I) (A.2.7) B-78 (I) (A.4.2) B-120 (I) (B.1.37)
B-37 (I) (A.2.8) B-79 (I) (A.4.3) B-121 (I) (B.1.38)
B-38 (I) (A.3.1) B-80 (I) (A.4.4) B-122 (I) (B.1.43)
B-39 (I) (A.3.2) B-81 (I) (A.4.5) B-123 (I) (B.1.44)
B-40 (I) (A.3.3) B-82 (I) (A.4.6) B-124 (I) (B.1.45)
B-41 (I) (A.3.4) B-83 (I) (A.4.7) B-125 (I) (B.1.46)
B-42 (I) (A.3.5) B-84 (I) (A.4.8) B-126 (I) (B.1.47) Mixt. Co.1 Co.2 Mixt. Co.1 Co.2 Mixt. Co.1 Co.2
B-127 (I) (B.1.48) B-169 (I) (E.1.3) B-211 (I) (H.1.4)
B-128 (I) (B.1.49) B-170 (I) (E.2.1) B-212 (I) (H.1.5)
B-129 (I) (B.1.50) B-171 (I) (E.2.2) B-213 (I) (H.1.6)
B-130 (I) (B.1.51) B-172 (I) (E.2.3) B-214 (I) (H.2.1)
B-131 (I) (B.2.1) B-173 (I) (E.2.4) B-215 (I) (H.2.2)
B-132 (I) (B.2.2) B-174 (I) (E.2.5) B-216 (I) (H.2.3)
B-133 (I) (B.2.3) B-175 (I) (E.2.6) B-217 (I) (H.2.4)
B-134 (I) (B.2.4) B-176 (I) (E.2.7) B-218 (I) (H.2.5)
B-135 (I) (B.2.5) B-177 (I) (E.2.8) B-219 (I) (H.2.6)
B-136 (I) (B.2.6) B-178 (I) (F.1.1) B-220 (I) (H.2.7)
B-137 (I) (B.2.7) B-179 (I) (F.1.2) B-221 (I) (H.2.8)
B-138 (I) (B.2.8) B-180 (I) (F.1.3) B-222 (I) (H.2.9)
B-139 (I) (B.3.1) B-181 (I) (F.1.4) B-223 (I) (H.3.1)
B-140 (I) (C.1.1) B-182 (I) (F.1.5) B-224 (I) (H.3.2)
B-141 (I) (C.1.2) B-183 (I) (F.1.6) B-225 (I) (H.3.3)
B-142 (I) (C.1.3) B-184 (I) (F.2.1) B-226 (I) (H.3.4)
B-143 (I) (C.1.4) B-185 (I) (G.1.1) B-227 (I) (H.3.5)
B-144 (I) (C.1.5) B-186 (I) (G.1.2) B-228 (I) (H.3.6)
B-145 (I) (C.1.6) B-187 (I) (G.1.3) B-229 (I) (H.3.7)
B-146 (I) (C.1.7) B-188 (I) (G.1.4) B-230 (I) (H.3.8)
B-147 (I) (C.2.1) B-189 (I) (G.2.1) B-231 (I) (H.3.9)
B-148 (I) (C.2.2) B-190 (I) (G.2.2) B-232 (I) (H.3.10)
B-149 (I) (C.2.3) B-191 (I) (G.2.3) B-233 (I) (H.3.11)
B-150 (I) (C.2.4) B-192 (I) (G.2.4) B-234 (I) (H.4.1)
B-151 (I) (C.2.5) B-193 (I) (G.2.5) B-235 (I) (H.4.2)
B-152 (I) (C.2.6) B-194 (I) (G.2.6) B-236 (I) (H.4.3)
B-153 (I) (C.2.7) B-195 (I) (G.2.7) B-237 (I) (H.4.4)
B-154 (I) (D.1.1) B-196 (I) (G.3.1) B-238 (I) (H.4.5)
B-155 (I) (D.1.2) B-197 (I) (G.3.2) B-239 (I) (H.4.6)
B-156 (I) (D.1.3) B-198 (I) (G.3.3) B-240 (I) (H.4.7)
B-157 (I) (D.1.4) B-199 (I) (G.3.4) B-241 (I) (H.4.8)
B-158 (I) (D.1.5) B-200 (I) (G.3.5) B-242 (I) (H.4.9)
B-159 (I) (D.1.6) B-201 (I) (G.3.6) B-243 (I) (H.4.10)
B-160 (I) (D.2.1) B-202 (I) (G.3.7) B-244 (I) (1.1.1)
B-161 (I) (D.2.2) B-203 (I) (G.3.8) B-245 (I) (1.1.2)
B-162 (I) (D.2.3) B-204 (I) (G.4.1) B-246 (I) (1.2.1)
B-163 (I) (D.2.4) B-205 (I) (G.5.1) B-247 (I) (I.2.2)
B-164 (I) (D.2.5) B-206 (I) (G.5.2) B-248 (I) (I.2.3)
B-165 (I) (D.2.6) B-207 (I) (G.5.3) B-249 (I) (I.2.4)
B-166 (I) (D.2.7) B-208 (I) (H.1.1) B-250 (I) (I.2.5)
B-167 (I) (E.1.1) B-209 (I) (H.1.2) B-251 (I) (J.1.1)
B-168 (I) (E.1.2) B-210 (I) (H.1.3) B-252 (I) (J.1.2) Mixt. Co.1 Co.2 Mixt. Co.1 Co.2 Mixt. Co.1 Co.2
B-253 (I) (J.1.3) B-295 (I) (K.1.35) B-337 (I) (M.1.31)
B-254 (I) (J.1.4) B-296 (I) (K.1.36) B-338 (I) (M.1.32)
B-255 (I) (J.1.5) B-297 (I) (K.1.37) B-339 (I) (M.1.33)
B-256 (I) (J.1.6) B-298 (I) (K.1.38) B-340 (I) (M.1.34)
B-257 (I) (J.1.7) B-299 (I) (K.1.39) B-341 (I) (M.1.35)
B-258 (I) (J.1.8) B-300 (I) (K.1.40) B-342 (I) (M.1.36)
B-259 (I) (J.1.9) B-301 (I) (K.1.41) B-343 (I) (M.1.37)
B-260 (I) (J.1.10) B-302 (I) (K.1.42) B-344 (I) (M.1.38)
B-261 (I) (K.1.1) B-303 (I) (K.1.43) B-345 (I) (M.1.39)
B-262 (I) (K.1.2) B-304 (I) (K.1.44) B-346 (I) (M.1.40)
B-263 (I) (K.1.3) B-305 (I) (K.1.45) B-347 (I) (M.1.41)
B-264 (I) (K.1.4) B-306 (I) (K.1.47) B-348 (I) (M.1.42)
B-265 (I) (K.1.5) B-307 (I) (M.1.1) B-349 (I) (M.1.43)
B-266 (I) (K.1.6) B-308 (I) (M.1.2) B-350 (I) (M.1.44)
B-267 (I) (K.1.7) B-309 (I) (M.1.3) B-351 (I) (M.1.45)
B-268 (I) (K.1.8) B-310 (I) (M.1.4) B-352 (I) (M.1.46)
B-269 (I) (K.1.9) B-311 (I) (M.1.5) B-353 (I) (M.1.47)
B-270 (I) (K.1.10) B-312 (I) (M.1.6) B-354 (I) (M.1.48)
B-271 (I) (K.1.11) B-313 (I) (M.1.7) B-355 (I) (M.1.49)
B-272 (I) (K.1.12) B-314 (I) (M.1.8) B-356 (I) (M.1.50)
B-273 (I) (K.1.13) B-315 (I) (M.1.9) B-357 (I) (N.1.1)
B-274 (I) (K.1.14) B-316 (I) (M.1.10) B-358 (I) (N.1.2)
B-275 (I) (K.1.15) B-317 (I) (M.1.11) B-359 (I) (N.1.3)
B-276 (I) (K.1.16) B-318 (I) (M.1.12) B-360 (I) (N.1.4)
B-277 (I) (K.1.17) B-319 (I) (M.1.13) B-361 (I) (N.1.5)
B-278 (I) (K.1.18) B-320 (I) (M.1.14) B-362 (I) (N.2.1)
B-279 (I) (K.1.19) B-321 (I) (M.1.15) B-363 (I) (N.2.2)
B-280 (I) (K.1.20) B-322 (I) (M.1.16) B-364 (I) (N.2.3)
B-281 (I) (K.1.21) B-323 (I) (M.1.17) B-365 (I) (N.3.1)
B-282 (I) (K.1.22) B-324 (I) (M.1.18) B-366 (I) (N.3.2)
B-283 (I) (K.1.23) B-325 (I) (M.1.19) B-367 (I) (N.3.3)
B-284 (I) (K.1.24) B-326 (I) (M.1.20) B-368 (I) (N.3.4)
B-285 (I) (K.1.25) B-327 (I) (M.1.21) B-369 (I) (N.4.1)
B-286 (I) (K.1.26) B-328 (I) (M.1.22) B-370 (I) (N.5.1)
B-287 (I) (K.1.27) B-329 (I) (M.1.23) B-371 (I) (N.6.1)
B-288 (I) (K.1.28) B-330 (I) (M.1.24) B-372 (I) (N.6.2)
B-289 (I) (K.1.29) B-331 (I) (M.1.25) B-373 (I) (N.6.3)
B-290 (I) (K.1.30) B-332 (I) (M.1.26) B-374 (I) (N.6.4)
B-291 (I) (K.1.31) B-333 (I) (M.1.27) B-375 (I) (N.6.5)
B-292 (I) (K.1.32) B-334 (I) (M.1.28) B-376 (I) (N.7.1)
B-293 (I) (K.1.33) B-335 (I) (M.1.29) B-377 (I) (N.7.2)
B-294 (I) (K.1.34) B-336 (I) (M.1.30) B-378 (I) (N.7.3) Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2
B-379 (I) (N.8.1 ) B-421 (I) (0.1 .4) B-463 (I) (0.2.8)
B-380 (I) (N.9.1 ) B-422 (I) (0.1 .5) B-464 (I) (0.2.9)
B-381 (I) (N.10.1 ) B-423 (I) (0.1 .6) B-465 (I) (0.2.10)
B-382 (I) (N.10.2) B-424 (I) (0.1 .7) B-466 (I) (0.2.1 1 )
B-383 (I) (N.10.3) B-425 (I) (0.1 .8) B-467 (I) (0.2.12)
B-384 (I) (N.10.4) B-426 (I) (0.1 .9) B-468 (I) (0.2.13)
B-385 (I) (N.10.5) B-427 (I) (0.1.10) B-469 (I) (0.2.14)
B-386 (I) (N.1 1 .1 ) B-428 (I) (0.1.1 1 ) B-470 (I) (0.2.15)
B-387 (I) (N.12.1 ) B-429 (I) (0.1.12) B-471 (I) (0.2.16)
B-388 (I) (N.12.2) B-430 (I) (0.1.13) B-472 (I) (0.3.1 )
B-389 (I) (N.12.3) B-431 (I) (0.1.14) B-473 (I) (0.3.2)
B-390 (I) (N.12.4) B-432 (I) (0.1.15) B-474 (I) (0.3.3)
B-391 (I) (N.13.1 ) B-433 (I) (0.1.16) B-475 (I) (0.3.4)
B-392 (I) (N.13.2) B-434 (I) (0.1.17) B-476 (I) (0.3.5)
B-393 (I) (N.13.3) B-435 (I) (0.1.18) B-477 (I) (0.3.6)
B-394 (I) (N.13.4) B-436 (I) (0.1.19) B-478 (I) (0.3.7)
B-395 (I) (N.13.5) B-437 (I) (0.1.20) B-479 (I) (0.3.8)
B-396 (I) (N.13.6) B-438 (I) (0.1.21 ) B-480 (I) (0.3.9)
B-397 (I) (N.13.7) B-439 (I) (0.1.22) B-481 (I) (0.3.10)
B-398 (I) (N.13.8) B-440 (I) (0.1.23) B-482 (I) (0.3.1 1 )
B-399 (I) (N.13.9) B-441 (I) (0.1.24) B-483 (I) (0.3.12)
B-400 (I) (N.14.1 ) B-442 (I) (0.1.25) B-484 (I) (0.3.13)
B-401 (I) (N.14.2) B-443 (I) (0.1.26) B-485 (I) (0.3.14)
B-402 (I) (N.14.3) B-444 (I) (0.1.27) B-486 (I) (0.3.15)
B-403 (I) (N.15.1 ) B-445 (I) (0.1.28) B-487 (I) (0.3.16)
B-404 (I) (N.16.1 ) B-446 (I) (0.1.29) B-488 (I) (0.3.17)
B-405 (I) (N.16.2) B-447 (I) (0.1.30) B-489 (I) (0.3.18)
B-406 (I) (N.17.1 ) B-448 (I) (0.1.31 ) B-490 (I) (0.3.19)
B-407 (I) (N.17.2) B-449 (I) (0.1.32) B-491 (I) (O.3.20)
B-408 (I) (N.17.3) B-450 (I) (0.1.33) B-492 (I) (0.3.21 )
B-409 (I) (N.17.4) B-451 (I) (0.1.34) B-493 (I) (0.3.22)
B-410 (I) (N.17.5) B-452 (I) (0.1.35) B-494 (I) (0.3.23)
B-41 1 (I) (N.17.6) B-453 (I) (0.1.36) B-495 (I) (0.3.24)
B-412 (I) (N.17.7) B-454 (I) (0.1.37) B-496 (I) (0.3.25)
B-413 (I) (N.17.8) B-455 (I) (0.1.38) B-497 (I) (0.3.26)
B-414 (I) (N.17.9) B-456 (I) (0.2.1 ) B-498 (I) (0.3.27)
B-415 (I) (N.17.10) B-457 (I) (0.2.2) B-499 (I) (0.4.1 )
B-416 (I) (N.17.1 1 ) B-458 (I) (0.2.3) B-500 (I) (0.4.2)
B-417 (I) (N.17.12) B-459 (I) (0.2.4) B-501 (I) (0.4.3)
B-418 (I) (0.1.1 ) B-460 (I) (0.2.5) B-502 (I) (0.4.4)
B-419 (I) (0.1.2) B-461 (I) (0.2.6) B-503 (I) (0.4.5)
B-420 (I) (0.1.3) B-462 (I) (0.2.7) B-504 (I) (0.4.6) Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2
B-505 (I) (0.4.7) B-547 (I) (0.8.3) B-589 (I) (0.21.1 )
B-506 (I) (0.4.8) B-548 (I) (0.8.4) B-590 (I) (0.21.2)
B-507 (I) (0.4.9) B-549 (I) (0.8.5) B-591 (I) (0.21.3)
B-508 (I) (O.4.10) B-550 (I) (0.9.1 ) B-592 (I) (0.21.4)
B-509 (I) (0.4.1 1 ) B-551 (I) (0.9.2) B-593 (I) (0.21.5)
B-510 (I) (0.4.12) B-552 (I) (0.9.3) B-594 (I) (0.21.6)
B-51 1 (I) (0.4.13) B-553 (I) (O.10.1 ) B-595 (I) (0.21.7)
B-512 (I) (0.4.14) B-554 (I) (0.1 1.1 ) B-596 (I) (0.22.1 )
B-513 (I) (0.4.15) B-555 (I) (0.1 1.2) B-597 (I) (0.22.2)
B-514 (I) (0.4.16) B-556 (I) (0.1 1.3) B-598 (I) (0.22.3)
B-515 (I) (0.4.17) B-557 (I) (0.1 1.4) B-599 (I) (0.22.4)
B-516 (I) (0.4.18) B-558 (I) (0.12.1 ) B-600 (I) (0.23.1 )
B-517 (I) (0.4.19) B-559 (I) (0.13.1 ) B-601 (I) (0.23.2)
B-518 (I) (O.4.20) B-560 (I) (0.14.1 ) B-602 (I) (0.23.3)
B-519 (I) (0.4.21 ) B-561 (I) (0.14.2) B-603 (I) (0.24.1 )
B-520 (I) (0.4.22) B-562 (I) (0.15.1 ) B-604 (I) (0.24.2)
B-521 (I) (0.4.23) B-563 (I) (0.15.2) B-605 (I) (0.24.3)
B-522 (I) (0.4.24) B-564 (I) (0.15.3) B-606 (I) (0.24.4)
B-523 (I) (0.5.1 ) B-565 (I) (0.15.4) B-607 (I) (0.24.5)
B-524 (I) (0.5.2) B-566 (I) (0.15.5) B-608 (I) (0.25.1 )
B-525 (I) (0.5.3) B-567 (I) (0.15.6) B-609 (I) (0.25.2)
B-526 (I) (0.5.4) B-568 (I) (0.15.7) B-610 (I) (0.26.1 )
B-527 (I) (0.5.5) B-569 (I) (0.15.8) B-61 1 (I) (0.26.2)
B-528 (I) (0.5.6) B-570 (I) (0.15.9) B-612 (I) (0.26.3)
B-529 (I) (0.5.7) B-571 (I) (0.15.10) B-613 (I) (0.26.4)
B-530 (I) (0.5.8) B-572 (I) (0.15.1 1 ) B-614 (I) (0.26.5)
B-531 (I) (0.5.9) B-573 (I) (0.16.1 ) B-615 (I) (0.26.6)
B-532 (I) (0.6.1 ) B-574 (I) (0.16.2) B-616 (I) (0.26.7)
B-533 (I) (0.6.2) B-575 (I) (0.16.3) B-617 (I) (0.26.8)
B-534 (I) (0.6.3) B-576 (I) (0.16.4) B-618 (I) (0.26.9)
B-535 (I) (0.6.4) B-577 (I) (0.16.5) B-619 (I) (O.26.10)
B-536 (I) (0.6.5) B-578 (I) (0.16.6) B-620 (I) (0.26.1 1 )
B-537 (I) (0.6.6) B-579 (I) (0.17.1 ) B-621 (I) (0.26.12)
B-538 (I) (0.6.7) B-580 (I) (0.18.1 ) B-622 (I) (0.26.13)
B-539 (I) (0.7.1 ) B-581 (I) (0.18.2) B-623 (I) (0.26.14)
B-540 (I) (0.7.2) B-582 (I) (0.18.3) B-624 (I) (0.26.15)
B-541 (I) (0.7.3) B-583 (I) (0.18.4) B-625 (I) (0.26.16)
B-542 (I) (0.7.4) B-584 (I) (0.18.5) B-626 (I) (0.26.17)
B-543 (I) (0.7.5) B-585 (I) (0.19.1 ) B-627 (I) (0.26.18)
B-544 (I) (0.7.6) B-586 (I) (O.20.1 ) B-628 (I) (0.27.1 )
B-545 (I) (0.8.1 ) B-587 (I) (O.20.2) B-629 (I) (0.27.2)
B-546 (I) (0.8.2) B-588 (I) (O.20.3) B-630 (I) (0.27.3) Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2 Mixt. Co.1 Co. 2
B-631 (I) (0.27.4) B-664 (I) (0.27.37) B-697 (I) (O.27.70)
B-632 (I) (0.27.5) B-665 (I) (0.27.38) B-698 (I) (0.27.71 )
B-633 (I) (0.27.6) B-666 (I) (0.27.39) B-699 (I) (0.27.72)
B-634 (I) (0.27.7) B-667 (I) (O.27.40) B-700 (I) (0.27.73)
B-635 (I) (0.27.8) B-668 (I) (0.27.41 ) B-701 (I) (0.27.74)
B-636 (I) (0.27.9) B-669 (I) (0.27.42) B-702 (I) (0.27.75)
B-637 (I) (O.27.10) B-670 (I) (0.27.43) B-703 (I) (0.27.76)
B-638 (I) (0.27.1 1 ) B-671 (I) (0.27.44) B-704 (I) (0.27.77)
B-639 (I) (0.27.12) B-672 (I) (0.27.45) B-705 (I) (0.27.78)
B-640 (I) (0.27.13) B-673 (I) (0.27.46) B-706 (I) (0.27.79)
B-641 (I) (0.27.14) B-674 (I) (0.27.47) B-707 (I) (O.27.80)
B-642 (I) (0.27.15) B-675 (I) (0.27.48) B-708 (I) (0.27.81 )
B-643 (I) (0.27.16) B-676 (I) (0.27.49) B-709 (I) (0.27.82)
B-644 (I) (0.27.17) B-677 (I) (O.27.50) B-710 (I) (0.27.83)
B-645 (I) (0.27.18) B-678 (I) (0.27.51 ) B-71 1 (I) (0.27.84)
B-646 (I) (0.27.19) B-679 (I) (0.27.52) B-712 (I) (0.27.85)
B-647 (I) (O.27.20) B-680 (I) (0.27.53) B-713 (I) (0.27.86)
B-648 (I) (0.27.21 ) B-681 (I) (0.27.54) B-714 (I) (0.27.87)
B-649 (I) (0.27.22) B-682 (I) (0.27.55) B-715 (I) (0.27.88)
B-650 (I) (0.27.23) B-683 (I) (0.27.56) B-716 (I) (0.27.89)
B-651 (I) (0.27.24) B-684 (I) (0.27.57) B-717 (I) (O.27.90)
B-652 (I) (0.27.25) B-685 (I) (0.27.58) B-718 (I) (0.27.91 )
B-653 (I) (0.27.26) B-686 (I) (0.27.59) B-719 (I) (0.27.92)
B-654 (I) (0.27.27) B-687 (I) (O.27.60) B-720 (I) (0.27.93)
B-655 (I) (0.27.28) B-688 (I) (0.27.61 ) B-721 (I) (0.27.94)
B-656 (I) (0.27.29) B-689 (I) (0.27.62) B-722 (I) (0.27.95)
B-657 (I) (O.27.30) B-690 (I) (0.27.63) B-723 (I) (0.27.96)
B-658 (I) (0.27.31 ) B-691 (I) (0.27.64) B-724 (I) (0.27.97)
B-659 (I) (0.27.32) B-692 (I) (0.27.65) B-725 (I) (0.27.98)
B-660 (I) (0.27.33) B-693 (I) (0.27.66) B-726 (I) (0.27.99)
B-661 (I) (0.27.34) B-694 (I) (0.27.67) B-727 (I) (0.27.100)
B-662 (I) (0.27.35) B-695 (I) (0.27.68)
B-663 (I) (0.27.36) B-696 (I) (0.27.69)
The mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
The mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the
Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). In addition, it is refered to the explanations regarding the fungicidal activity of the compounds and the compositions containing compounds I, respectively.
I. Synthesis examples
The compounds of formula I can be prepared according to the methods outlined below.
1.1 ) Preparation of N'-hydroxy-4-[1-(methylamino)ethyl]benzamidine
To a solution of 4-[1 -(methylamino)ethyl]benzonitrile (13 g, 1 eq.) in ethanol (150 mL) was added triethylamine (17.4 g, 2.5 eq.) and hydroxyl amine (9.5 g, 2 eq.). The mixture was refluxed for 3 hours and concentrated under reduced pressure. The crude product (13 g) was used directly without further purification.
1.2) Preparation N-methyl-1-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]ethanamine A solution of N'-hydroxy-4-[1 -(methylamino)ethyl]benzamidine as obtained in step 1.1 (35 g, 1 .0 eq.) in dichloromethane (400 mL) was treated with trifluoroacetic anhydride (97 g, 3 eq.) at room temperature. The mixture was stirred for 1 hour, before it was washed with a saturated aqueous solutions of sodium bicarbonate and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product (48 g) was that was used directly without further purification.
1.3) Preparation N-methyl-N-[1-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl] ethyl]acetamide (Ex-16)
To a solution of N-methyl-1 -[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl] ethanamine obtained in step 1.2 (8.5 g, 1 eq.) in dichloromethane (100 mL) was added triethylamine (5.9 g, 2.2 eq.) and acetyl chloride (2.3 g, 1 .1 eq.). The mixture was stirred overnight, before it was diluted with dichloromethane and washed with aqueous 1 N hydrochloric acid. The organic layer was successively washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and freed from solvent under reduced pressure. Flash chromatography on silica gel using cyclohexane - ethyl acetate provided the titled product (4.95 g).
H NMR (CDCIs): δ [ppm] = 1 .5 and 1 .65 (d, 3H), 2.15 and 2.25 (s, 3H), 2.7 (s, 3H), 5.25 and 6.15 (q, 1 H), 7.45 (m, 2H), 8.13 (m, 2H).
1.4) Preparation of N-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethyl- propanamide
To a solution of N-[(4-cyanophenyl)methyl]-N-methyl-acetamide (8.8 g, 1.0 eq.) in
tetrahydrofuran (50 mL) was added hydroxylamine hydrochloride (4.2 g, 1.5 eq.) and potassium carbonate (4.5 g, 0.8 eq.) in 20 mL water. The mixture was stirred overnight at 23 °C and the progress of the reaction was monitored by HPLC. It was filtered, washed five times with toluene and concentrated under reduced pressure to afford the title compound (10 g) that was used directly without further purification.
1.5) Preparation of N,2-dimethyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl] phenyl] methyl]propanamide (Ex-13)
A solution of N-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methyl]-N,2-dimethyl-propanamide obtained in step 1.4 (10 g, 1 .0 eq.) in tetrahydrofuran (100 ml.) was treated with trifluoroacetic anhydride (30 g, 3.5 eq.) at room temperature. The mixture was stirred for 2 hours,
concentrated under reduced pressure and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with aqueous 1 N hydrochloric acid and saturated aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was dissolved in dichloromethane and washed with saturated aqueous solution of sodium bicarbonate to remove trifluoroacetic acid, and concentrated under reduced pressure to afford the titled product (3 g). Melting point: 55 °C
1.6) Preparation of N'-hydroxy-4-[(2-oxopyrrolidin-1 -yl)methyl]benzamidine
To a solution of 4-[(2-oxopyrrolidin-1-yl)methyl]benzonitrile (0.55 g, 1 .0 eq.) in ethanol (5 ml.) was added hydroxylamine hydrochloride (0.382 g, 2 eq.) and triethylamine (0.694 g, 2.5 eq.). The mixture was refluxed for 4 hours and concentrated under reduced pressure to afford the title compound that was used directly without further purification.
1.7) Preparation of 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl] pyrrolidin-2- one (Ex-30)
A solution of N'-hydroxy-4-[(2-oxopyrrolidin-1-yl)methyl]benzamidine obtained in step 1.5 (1 g, 1.0 eq.) in dichloromethan (5 ml.) was treated with trifluoroacetic anhydride (4.5 g, 5 eq.) at room temperature. The mixture was stirred for 2 hours at 23 °C, washed with saturated aqueous solution of sodium bicarbonate and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel using cyclohexane- ethyl acetate provided the titled product (80 mg). 1H NMR (CDCI3): δ [ppm] = 2.1 (m, 2H), 2.45 (m, 2H), 3.3 (m, 3H), 4.5 (s, 2H), 7.4 (m, 2H), 8.13 (m, 2H).
The compounds Ex-1 to Ex-34 listed in Table I were prepared in an analogous manner. Table I: Compounds Ex-1 to Ex-34 of formula I. Ex, wherein A corresponds to subformula (A.4), wherein A is unsubstituted, and wherein the meaning of R1, R2 , R3 and R4 are as defined in each line, and wherein # denotes the point of attachment of the NR1R2 group to the CR3R4 moiety.
Figure imgf000075_0001
Ex. no R3 R4 R1 R2 HPLC Rt7
(M+H); or Melting point (°C)
Ex-1 CFs H CHs H 0.94/326
Ex-2 CFs H cyclopropyl H 1 .28/352
Ex-3 H H CHs C(=0)-CH3 1 .09/300
H H
Ex-4 allyl C(=0)-CHs 1 .17/326
Ex-5 H H allyl C(=0)-CH2CH3 1 .24/340
Ex-6 H H allyl C(=0)-C(CHs)3 1 .34/368
Ex-7 H H CHs C(=0)-CH2CHs 1 .16/314
Ex-8 H H CHs C(=0)-C(CH3)s 1 .29/342
Ex-9 H H CH(CHs)2 C(=0)-CH2CH3 1 .26/342
Ex-10 H H CH(CHs)2 C(=0)-C(CHs)3 1 .38/370
Ex-1 1 H H CHs C(=0)-CH(CH2CHs)2 1 .26/356
Ex-12 H H CHs C(=0)-CH2CH2CH3 1.174/328
Ex-13 H H CHs C(=0)-CH(CHs)2 1.170/328
Ex-14 H H CHs C(=0)-CHCH3CH2CH3 1 .21/342
Ex-15 H H H C(=0)-CH3 132 °C
Ex-16 CHs H CHs C(=0)-CHs 1 .1 1/314
Ex-17 CHs H CHs C(=0)-C(CH3)s 1 .36/356
Ex-18 CHs H CHs C(=0)-CH2CH3 1 .20/327
Ex-19 CHs H CHs C(=0)-CH2CH2CH3 1 .24/341
Ex-20 CHs H CHs C(=0)-CH(CH2CH3)2 1 .36/369
Ex-21 CHs H CHs C(=0)-CH(CHs)2 1 .24/341
Ex-22 CHs H CHs C(=0)-CHCH3CH2CH3 1 .30/355
Ex-23 CFs H H C(=0)-CH3 191 °C
Ex-24 H H CH2CHs C(=0)-CH(CHs)2 1 .32/341
Ex-25 H H CH2CH3 C(=0)-CH2CH2CH3 1 .24/341
Ex-26 H H CH2CH3 C(=0)-CH2CHs 1 .31/327
Ex-27 H H CH2CH3 C(=0)-C(CH3)s 1 .32/355
Ex-28 H H CH2CH3 C(=0)-CHCH3CH2CH3 1 .29/355
H H
Ex-29 1 .31/367
Figure imgf000076_0001
*HPLC: High Performance Liquid Chromatography; HPLC-column Kinetex XB C18 1 ,7μ (50 x 2, 1 mm); eluent: acetonitrile / water + 0.1 % trifluoroacetic acid (gradient from 5:95 to 100 : 0 in
I .5 min at 60°C, flow gradient from 0.8 to 1 .0 ml/min in 1 .5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode). Rt: retention time in minutes.
II . Biological examples for fungicidal activity
The fungicidal action of the compounds of formula I was demonstrated by the following experiments:
A. Glass house trials
The spray solutions were prepared in several steps: The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml. This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.
11.1 ) Curative control of soy bean rust on soy beans caused by Phakopsora pachyrhizi
Leaves of pot-grown soy bean seedlings were inoculated with spores of Phakopsora pachyrhizi. To ensure the success of the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95 % and 20 to 24 °C for 24 hours. The next day the plants were cultivated for 3 days in a greenhouse chamber at 23 to 27 °C and a relative humidity between 60 and 80 %. Then the plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. Then the trial plants were cultivated for 14 days in a greenhouse chamber at 23 to 27 °C and a relative humidity between 60 and 80 %. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the plants which had been treated with 32 ppm of the active compound Ex-1 , Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-1 1 , Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21 , Ex-22, Ex-23, Ex-28, Ex-30, Ex-31 , Ex-32 and Ex-33 showed a diseased leaf area of at most 5 %, whereas the untreated plants showed 90 % diseased leaf area.
11.2) Protective control of soy bean rust on soy beans caused by Phakopsora pachyrhizi Leaves of pot-grown soy bean seedlings were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. The trial plants were cultivated for 2 day in a greenhouse chamber at 23 to 27 °C and a relative humidity between 60 and 80 %.Then the plants were inoculated with spores of Phakopsora pachyrhizi. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber with a relative humidity of about 95 % and 20 to 24 °C for 24 h. The trial plants were cultivated for fourteen days in a greenhouse chamber at 23 to 27 °C and a relative humidity between 60 and 80 %. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the plants which had been treated with 32 ppm of the active compound Ex-1 , Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-1 1 , Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21 , Ex-22, Ex-23, Ex-28, Ex-29, Ex-30, Ex-31 , Ex-32 and Ex-33 showed a diseased leaf area of 0 %, whereas the untreated plants showed 90 % diseased leaf area.
In this test, the plants which had been treated with 16 ppm of the active compound Ex-24, Ex- 25, Ex-26 and Ex-27 showed a diseased leaf area of 0 %, whereas the untreated plants showed 90 % diseased leaf area.
II.3) Curative control of brown rust on wheat caused by Puccinia recondita
The first two developed leaves of pot-grown wheat seedling were dusted with spores of
Puccinia recondita. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99 % and 20 to 24 °C for 24 hours. The next day the plants were cultivated for 3 days in a greenhouse chamber at 20 to 24 °C and a relative humidity between 65 and 70 %. Then the plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. The plants were allowed to air-dry. Then the trial plants were cultivated for 8 days in a greenhouse chamber at 20 to 24 °C and a relative humidity between 65 and 70 %. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the plants which had been treated with 63 ppm of the active compound Ex-1 , Ex-4, Ex-5, Ex-7, Ex-8, Ex-9, Ex-10, Ex-1 1 , Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-18, Ex-19, Ex-21 , Ex-23, Ex-31 and Ex-33 showed a diseased leaf area of at most 2 %, whereas the untreated plants showed 90 % diseased leaf area.
11.4) Preventative control of brown rust on wheat caused by Puccinia recondita
The first two developed leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below. Seven days later the plants were inoculated with spores of Puccinia recondita. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99 % and 20 to 24 °C for 24 h. Then the trial plants were cultivated for 6 days in a greenhouse chamber at 20 to 24 °C and a relative humidity between 65 and 70 %. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the plants which had been treated with 63 ppm of the active compound Ex-4, Ex-5, Ex-8, Ex-9, Ex-10, Ex-1 1 , Ex-12, Ex-13 and Ex-14 showed a diseased leaf area of at most 12 %, whereas the untreated plants showed 90 % diseased leaf area.

Claims

Claims
1. The use of the compounds of the formula I
Figure imgf000079_0001
is phenyl or a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein the cyclic groups A are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups RA; wherein
RA is halogen, cyano, N02, OH, NH2, SH, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6- alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl or Cs-Cs-cycloalkoxy; and wherein any of the aliphatic or cyclic moieties are unsubstituted or substituted by 1 , 2, 3 or 4 identical or different groups Ra; wherein
Ra is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio or C3-C8-cycloalkyl;
, R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C(=0)-(Ci-C6-alkyl), C(=0)-(Ci-C6- alkoxy), phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6- membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a; or
and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 , 2 or 3 further heteroatoms independently selected from N, O and S as ring member atoms; and wherein one or two CH2 groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a; wherein
R1a is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, NHS02-Ci-C4-alkyl, (C=0)-(Ci-C4-alkyl), C(=0)-(Ci-C4-alkoxy) or Ci-C6-alkylsulfonyl;
R3 is H, Ci-C4-alkyl, C C4-haloalkyl;
R4 is H, Ci-C4-alkyl, Ci-C4-haloalkyl;
or the N-oxides, or the agriculturally acceptable salts thereof for combating
phytopathogenic harmful fungi.
Use according to claim 1 , wherein A is (A.4), which is unsubstituted,
Figure imgf000080_0001
and wherein #1 shall denote the position which is bound to the trifluoromethyloxadiazole moiety and #2 denotes the position, which is connected to the -C(R3R4)-NR1 R2 group in compounds of the formula I.
Use according to claim 1 or 2, wherein R1 and R2 independently of each other are hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy); and wherein any of the aliphatic or cyclic groups are
unsubstituted or substituted by 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a as defined in claim 1 .
Use according to any one of claims 1 to 3, wherein R3, R4 independently of each other are H, CH3 or CF3.
Compounds of the formula I as defined in any one of claims 1 to 3, wherein
R3 is H and
R4 is CF3.
Compounds of the formula I as defined in claim 1 or 2, wherein
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl,
Cs-Ce-cycloalkenyl, C(=0)-(Ci-C6-alkyl), C(=0)-(Ci-C6-alkoxy), phenyl-Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl, naphthyl or a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, wherein the ring member atoms of said mono- or bicyclic heterocycle include besides carbon atoms further 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms and wherein 1 or 2 carbon ring member atoms of the heterocycle may be replaced by 1 or 2 groups independently selected from C(=0) and C(=S); and wherein the heteroaryl group in heteroaryl-Ci-C4-alkyl is a 5- or 6-membered aromatic heterocycle, wherein the ring member atoms of the heterocyclic ring include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring member atoms; and wherein any of the above-mentioned aliphatic or cyclic groups are unsubstituted or substituted by 1 , 2, 3 or up to the maximum possible number of identical or different groups R1a as defined in claim 1 ; and
R2 is C(=0)-(Ci-C6-alkyl) or C(=0)-(Ci-C6-alkoxy).
7. Compounds of the formula I as defined in claim 1 or 2, wherein
R1 and R2 together with the nitrogen atom to which they are bound form a saturated or partially unsaturated mono- or bicyclic 3- to 7-membered heterocycle, wherein the heterocycle includes beside one nitrogen atom and one or more carbon atoms no further heteroatom or 1 , 2 or 3 further heteroatoms independently selected from N,
O and S as ring member atoms; and wherein one or two Ch groups of the heterocycle may be replaced by one or two groups independently selected from the group of C(=0) and C(=S); and wherein the heterocycle is unsubstituted or carries 1 , 2, 3, 4 or up to the maximum possible number of identical or different groups R1a; wherein
R1a is halogen, cyano, N02, OH, SH, NH2, Ci-C6-alkyl, Ci-C6-haloalkyl,
Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8- cycloalkyl, NHS02-Ci-C4-alkyl, (C=0)-(Ci-C4-alkyl), C(=0)-(Ci-C4-alkoxy) or Ci-C6-alkylsulfonyl.
8. A mixture comprising at least one compound of the formula I as defined in any one of claims 1 to 7 and at least one further pesticidally active substance selected from the group consisting of herbicides, safeners, fungicides, insecticides, and plant growth regulators. 9. An agrochemical composition, which comprises an auxiliary and at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, according to any one of claims 1 to 7.
10. An agrochemical composition according to claim 9, wherein the auxiliary is selected from the group consisting of anionic, cationic and nonionic surfactants.
1 1. An agrochemical composition according to claim 9 or 10 further comprising seed, wherein the amount of the compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, is from 0.1 g to 10 kg per 100 kg of seed.
12. A method for combating phytopathogenic harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I, or an N-oxide, or an agriculturally acceptable salt thereof as defined in any one of claims 1 to 7.
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