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WO2018219797A1 - Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes - Google Patents

Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes Download PDF

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Publication number
WO2018219797A1
WO2018219797A1 PCT/EP2018/063766 EP2018063766W WO2018219797A1 WO 2018219797 A1 WO2018219797 A1 WO 2018219797A1 EP 2018063766 W EP2018063766 W EP 2018063766W WO 2018219797 A1 WO2018219797 A1 WO 2018219797A1
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phenyl
alkyl
methyl
group
cyclopropyl
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PCT/EP2018/063766
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English (en)
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Violeta TERTERYAN-SEISER
Wassilios Grammenos
Maria Angelica QUINTERO PALOMAR
Ian Robert CRAIG
Marcus Fehr
Tobias MENTZEL
Thomas Grote
Christine WIEBE
Christian Winter
Ana Escribano Cuesta
Bernd Mueller
Jan Klaas Lohmann
Erica CAMBEIS
Michael Seet
Georg Christoph RUDOLF
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Basf Se
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Publication of WO2018219797A1 publication Critical patent/WO2018219797A1/fr

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    • 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

Definitions

  • the present invention relates to substituted oxadiazoles of the formula I, or the N-oxides, or the agriculturally useful salts thereof, and to the use thereof for controlling phytopathogenic fungi; to a method for combating phytopathogenic harmful fungi, which process comprises treating the fungi, the 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; and to agrochemical compositions comprising at least one compound of the formula I, or an N-oxide, or an agriculturally acceptable salt thereof, and further comprising seeds.
  • EP 276432 WO 97/30047, WO 2015/185485, WO 2017/055469, WO 2017/055473, WO 2017/072247, WO 2017/076742, WO 2017/076739, WO 2017/076757, WO 2017/081309, WO2017/081310, WO 2017/08131 1 , WO 2017/081312, WO 2017/076740, WO 2017/076935, WO 2017/085098 and WO 2017/085100 describe derivatives of trifluoromethyloxadiazoles and their use to combat phytopathogenic microorganisms.
  • 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 or their agriculturally useful salts for controlling phytopathogenic fungi.
  • the present invention relates to compounds of the formula I, or the N-oxides, or the agriculturally acceptable salts thereof,
  • A is phenyl or 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; and wherein the phenyl ring or the aromatic heterocycle is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups R A ; wherein
  • R A is halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy or
  • W is O or S
  • V is a direct single bond or a divalent group -NR 2 -;
  • R 2 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, C3-C8-cycloalkenyl, C3-C8-cycloalkyl-Ci-C6-alkyl, phenyl-Ci-C4-alkyl, phenyl, formyl or -N(R 2a )2; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl and Ci-C6-alkoxy; and wherein
  • R 2a is independently selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C6-alkylthio;
  • R 1 is a bicyclic carbocycle of the formula R a
  • C a and C b are bridgehead carbon atoms
  • X is a direct single bond or a divalent group selected from the group consisting of
  • Y and Z independently of each other are a divalent group selected from the group
  • R 1 is a tricyclic carbocycle of the formula R b
  • C a and C b are bridgehead carbon atoms
  • R 1 is a tricyclic carbocycle of the formula R b , wherein X is a direct single bond or a divalent group -CH 2 -, the groups T and Z independently of each other are a divalent group selected from the group consisting of -CH 2 -CH 2 -, -(CH 2 )3-,
  • groups R a or R b are connected to the group V through one of the ring carbon atoms; and wherein the groups R a or R b are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl, Ci-C3-haloalkyl, C3-C6-cycloalkyl, vinylidene and dichlorovinylidene; or
  • R 1 and one of the two groups R 2a together with the nitrogen atom to which R 2a is attached, and together with the nitrogen atom of the group -NR 2 -, form a saturated or partially unsaturated mono- or bicyclic 3- to 10-membered heterocycle, wherein the heterocycle includes beside two nitrogen atoms and one or more carbon atoms no further
  • R 3 , R 4 independently of each other are selected from the group consisting of hydrogen,
  • halogen cyano, d-C 4 -alkyl, d-C 4 -haloalkyl, d-C 4 -alkoxy and d-C 4 -haloalkoxy; or, if B is -C(R 3 ) 2 -C(R 4 ) 2 -, two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a saturated 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1 , 2 or 3 heteroatoms independently selected from the group consisiting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group R N ; wherein
  • R N is hydrogen, Ci-C6-alkyl or halogen
  • B is -C(R 3 )2-C(R 4 )2-, one radical R 3 and one radical R 4 , together with the carbon atoms that each of them are bound to, form a saturated 3- to 7-membered carbocycle or a saturated 3- to 6-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1 , 2 or 3 heteroatoms independently selected from the group consisiting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group R N ; wherein
  • R N is hydrogen, Ci-C6-alkyl or halogen
  • 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 be substituted with 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,
  • 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.
  • 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
  • R 3 , R 4 independently of each other are selected from the group -- herein means that each individual residue R 3 or R 4 is independently of each other selected from a group of radicals as defined herein. In this terminology, for example, one radical R 3 may be defined
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • 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.
  • 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.
  • 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.
  • Ci-C6-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, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCCI 3 , 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, OC 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy
  • 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.
  • Ci-C4-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-C6-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 “Ci-C6-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.
  • C2-C6-alkenyloxyimino-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, wherein two hydrogen atoms of one carbon atom of the alkyl radical are replaced
  • C3-C8-cycloalkyl-Ci-C6-alkyl refers to alkyl having 1 to 6 carbon atoms, wherein one hydrogen atom of the alkyl radical is replaced by a Cs-Cs-cycloalkyl 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 NH2 group.
  • Ci-C6-alkylamino refers to an amino group, which is substituted with one residue independently selected from the group that is defined by the term Ci-C6-alkyl.
  • diCi-C6-alkylamino refers to an amino group, which is substituted with two residues independently selected from the group that is defined by the term Ci-C6-alkyl.
  • 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- 1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
  • 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.
  • 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-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members such as cyclopropyl (C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • 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” refer to a radical which is an alicyclic ring or an aromatic ring, such as, for example, phenyl or heteroaryl.
  • aliphatic groups, cyclic groups and groups which contain an aliphatic and a cyclic moiety in one group, such as in, for example, C3-C8-cycloalkyl-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.
  • R 1 is attached to the group V through one carbon atom of the groups R a or R b , which includes any carbon atom of groups X, Y, Z, T and the bridgehead carbon atoms C a and C b , thereby replacing a hydrogen atom attached to said carbon atom.
  • 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 group B.
  • heteroaryl if not defined otherwise, 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.
  • saturated 3- to 7-membered carbocycle is to be understood as meaning monocyclic saturated carbocycles having 3, 4 or 5 carbon ring members. Examples include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
  • 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;
  • 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,
  • 5- or 6-membered heteroaryl or the term “5- or 6-membered aromatic heterocycle” refer 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
  • 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 embodiments of the compounds I. Preference is given to those compounds I and, where applicable, also to compounds of all subformulae provided herein, e. g.
  • A is phenyl which is unsubstituted or substituted with 1 , 2, 3 or 4 identical or different groups R A as defined or preferably defined herein and wherein the group B is attached to the phenyl ring in / ⁇ e s-position with regard to the oxadiazole group.
  • A is phenyl which is substituted with 1 or 2 identical or different groups R A as defined or preferably defined herein and wherein the group B is attached to the phenyl ring in para-pos ⁇ t ⁇ on with regard to the oxadiazole group.
  • A is phenyl which is unsubstituted and wherein the group B is attached to the phenyl ring in para-pos ⁇ t ⁇ on with regard to the oxadiazole 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 with 1 or 2 identical or different groups R A as defined or preferably defined herein; particularly R A is chlorine, fluorine or methyl.
  • 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 with 1 or 2 identical or different groups R A as defined or preferably defined herein; particularly R A is chlorine, fluorine or methyl; and wherein the group B is attached to the 6-membered aromatic heterocycle in para-pos ⁇ t ⁇ on with regard to the oxadiazole group.
  • A is a 5-membered aromatic heterocycle, in particular a thiophene ring, more particularly a 2,5-thiophenyl ring, 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 with 1 or 2 identical or different groups R A as defined or preferably defined herein; particularly R A is chlorine, fluorine or methyl.
  • the invention relates to compounds of the formula I, wherein the cyclic moiety A is defined as in subformulae (A.1 ) to (A.30),
  • R A is independently selected from the group consisting of halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl. In another preferred embodiment R A is independently selected from the group consisting of halogen, methyl or ethyl. More preferably R A is independently selected from the group consisting of halogen, in particular R A is fluorine.
  • Embodiment 1 .1 R 1 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, 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
  • Ci-C6-haloalkyl Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.
  • Embodiment 1 .2 R 1 is 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 cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Cs-Cs-cycloalkyl.
  • Embodiment 1 .3 R 1 is Cs-Cs-cycloalkyl or Cs-Cs-cycloalkenyl; and wherein the cyclic group is unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Cs-Cs- cycloalkyl.
  • Embodiment 1 .4 R 1 is Ci-C6-alkyl; and wherein the alkyl group is unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, Ci-C6-alkyl and Cs-Cs-cycloalkyl.
  • Embodiment 1 .5 R 1 is difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 3,3,3- trifluoropropyl, CH2CF2CF3 or CF 2 CF 2 CF 5 , CH(CH 3 )CF 3 , CH2CF2CH3, CH 2 C(CH 3 )2F,
  • Embodiment 1 .6 R 1 is Ci-C6-alkoxyimino-Ci-C4-alkyl, C2-C6-alkenyloxyimino-Ci-C4-alkyl or C2-C6-a I ky ny I oxy i m i n o-C 1 -C4-a I ky I .
  • Embodiment 1 .7 R 1 is a bicyclic carbocycle of the formula R a
  • C a and C b are bridgehead carbon atoms
  • X is a direct single bond or a divalent group selected from the group consisting of -CH2- and
  • Y and Z independently of each other are a divalent group selected from the group consisting of
  • R a is connected to the remainder of the compounds of formula I through one of the ring carbon atoms; and wherein R a is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl.
  • C a and C b are bridgehead carbon atoms
  • X is a direct single bond or a divalent group selected from the group consisting of -CH2- and
  • Y and Z independently of each other are a divalent group selected from the group consisting of -CH2- and -CH2-CH2-; and wherein groups Y and Z are attached to the bridgehead carbon atoms C a and C b ;
  • T is a divalent group selected from the group consisting of -CH2- and -CH2-CH2-;
  • Z independently of each other are a divalent group -CH2-CH2-;
  • R b is connected to the remainder of the compounds of formula I through one of the ring carbon atoms; and wherein R b is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen, Ci-C3-alkyl.
  • Embodiment 1 .9 R 1 is a bicyclic or tricyclic carbocycle selected from the group consisting of radicals R 1 .1 to R 1 .31 below; wherein each radical may be connected to the remainder of the compounds of formula I through one of the ring carbon atoms by substitution of one hydrogen atom; and wherein R 1 is unsubstituted or substituted with 1 or 2 radicals selected from the group consisting of oxo, hydroxy, halogen and Ci-C3-alkyl.
  • Embodiment 1 .10 R 1 is selected from the group consisting of R 1 .32 to R 1 .57 below, particularly from R 1 .32 to R 1 .49, which are further unsubstituted, and wherein "#C" indicates the carbon ato
  • R 1a is selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and Cs-Cs-cycloalkyl.
  • R 1a is selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, methoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy or cyclopropyl.
  • R 1a is selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Cs-Cs-cycloalkyl; particularly from methyl, ethyl, cyano, fluorine and chlorine; more particularly from fluorine and chlorine.
  • R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, propargyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl, formyl or - N(R 2a )2; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Ci-C6-alkoxy; more preferably from halogen, in particular the radical is fluorine; and wherein R 2a is independently selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl
  • R 2 is -N(R 2a )2, wherein R 2a is independently selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl and Ci-C6-alkoxy.
  • R 2a is independently selected from the group consisting of hydrogen, OH, methyl, ethyl, /7-propyl, /so-propyl, methoxy, ethoxy, propoxy, vinyl, allyl propargyl, cyclopropyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl and Ci-C6-alkoxy.
  • R 2 is methylamino or dimethylamino.
  • R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, propargyl, Cs-Cs- cycloalkyl, C3-Cs-cycloalkenyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl, formyl, Ci-C6-alkylamino or diCi-C6-alkylamino; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Ci-C6-alkoxy.
  • Embodiment 2.2 R 2 is hydrogen, methyl, ethyl, /7-propyl, /so-propyl, methoxy, ethyoxy, propyloxy, cyclopropyl, cyclopropyl-CH2-, allyl, phenyl, 4-F-phenyl, 2-F-phenyl, formyl, C1-C6- alkylamino or diCi-C6-alkylamino.
  • R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, propargyl, C3-C8- cycloalkyl, formyl, Ci-C6-alkylamino or diCi-C6-alkylamino.
  • Embodiment 2.4 R 2 is hydrogen, methyl, ethyl, /7-propyl, /so-propyl, methoxy, ethyoxy, propyloxy, cyclopropyl, cyclopropyl-Chb-, allyl, formyl, Ci-C6-alkylamino or diCi-C6-alkylamino.
  • Embodiment 2.5 R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl or propargyl, formyl, Ci-C6-alkylamino or diCi-C6-alkylamino.
  • Embodiment 2.6 R 2 is hydrogen, methy, ethyl, methoxy, ethyoxy, propyloxy, formyl,
  • Embodiment 2.7 R 2 is hydrogen.
  • R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, propargyl, C3-C8- cycloalkyl, Cs-Cs-cycloalkenyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl, formyl or -N(R 2a )2; and wherein any of the aliphatic or cyclic groups are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano, Ci-C6-alkyl and Ci-C6-alkoxy; more preferably from halogen, in particular the radical is fluorine; and wherein R 2a is independently selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C
  • Ci-C6-alkoxy; and R 1 is Ci-C6-alkyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, Cs-Cs-cycloalkyl,
  • R 2 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- alkoxy, C2-C6-alkenyl, propargyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, formyl, Ci-C6-alkylamino or diCi-C6-alkylamino; and R 1 is Ci-C6-alkyl, Ci-C6-alkoxyimino- Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl, C2-C6-alkenyl, C2-C6-alkynyl, phenyl- Ci-C4-alkyl, heteroaryl-Ci-C4-alkyl, phenyl or heteroaryl; and wherein the heteroaryl group is a 5- or 6-
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, Cs-Cs- cycloalkyl, Cs-Cs-cycloalkenyl, C2-C6-alkenyl or C2-C6-alkynyl; and wherein any of the aliphatic or cyclic groups in R 1 are unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and Ci-C6-alkyl.
  • group B is a divalent group -C(R 3 )2-C(R 4 )2-.
  • Embodiment 3.1 compounds of the formula I, wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl and Ci-C6-haloalkyl; or, if B is -C(R 3 )2-C(R 4 )2-, two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a cyclopropyl ring.
  • Embodiment 3.2 R 3 and R 4 independently of each other are selected from the group consisting of hydrogen and Ci-C4-alkyl.
  • Embodiment 3.3 R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, methyl and ethyl.
  • R 3 and R 4 are selected from the group consisting of hydrogen, fluorine, chlorine, methyl and trifluoromethyl; or, if B is -C(R 3 )2-C(R 4 )2-, two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a cyclopropyl ring.
  • Embodiment 3.5 R 3 and R 4 are hydrogen.
  • Embodiment 3.6 R 3 is hydrogen and R 4 is methyl.
  • Embodiment 3.7 R 3 and R 4 are methyl.
  • Embodiment 3.8 R 3 and R 4 are fluorine.
  • Embodiment 3.9 R 3 and R 4 are trifluoromethyl.
  • Embodiment 3.10 B is -C(R 3 )2-C(R 4 )2-, and two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a saturated monocyclic 3- to 5-membered saturated heterocycle or saturated carbocycle; and wherein the saturated heterocycle includes beside one or more carbon atoms no heteroatoms or 1 or 2 heteroatoms independently selected from N, O and S as ring member atoms; and wherein the heterocycle or the carbocycle is unsubstituted or substituted with 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and Ci-C2-alkyl.
  • Embodiment 3.1 1 B is -C(R 3 )2-C(R 4 )2-, and two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a 3- or 4-membered carbocylic ring.
  • Embodiment 3.12 B is -C(R 3 )2-C(R 4 )2-, and two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a cyclopropyl ring.
  • Embodiment 3.13 B is -C(R 3 )2-C(R 4 )2-, and two radicals R 3 and/or two radicals R 4 , which are bound to the same carbon atom, together with said carbon atom, form a saturated 3-membered heterocycle; wherein the heterocycle includes beside two carbon atoms one heteroatom selected from N, O and S as ring member atoms; and wherein the heterocycle is unsubstituted or substituted 1 , 2, 3, 4 or up to the maximum possible number of identical or different radicals selected from the group consisting of halogen, cyano and Ci-C2-alkyl.
  • Embodiment 3.14 R 3 is methyl and R 4 is fluorine.
  • Embodiment 3.15 R 3 is methyl and R 4 is hydrogen.
  • Embodiment 3.16 B is -C(R 3 )2-C(R 4 )2-, wherein R 3 is hydrogen and one radical R 4 is hydrogen and one radical R 4 is methyl.
  • Embodiment 3.17 B is -C(R 3 )2-C(R 4 )2-, wherein one radical R 3 is hydrogen and one radical R 3 is methyl and R 4 is hydrogen.
  • Embodiment 3.18 B is -C(R 3 )2-C(R 4 )2-, wherein one radical R 3 is hydrogen and one radical R 3 is methyl and one radical R 4 is methyl and one radical R 4 is hydrogen.
  • Embodiment 3.19 R 3 is fluorine and R 4 is hydrogen.
  • Embodiment 3.20 B is -C(R 3 )2-C(R 4 )2-, wherein one radical R 3 and one radical R 4 , together with the carbon atoms that each of them are bound to, form a saturated 3- to 5-membered carbocycle or a saturated 3- to 5-membered heterocycle; wherein the saturated heterocycle includes beside carbon atoms 1 , 2 or 3 heteroatoms independently selected from the group consisiting of N, O and S as ring member atoms; and wherein said N ring member atom is substituted with the group R N ; wherein
  • R N is hydrogen, Ci-C6-alkyl or halogen
  • Embodiment 3.21 B is -C(R 3 )2-C(R 4 )2-, wherein one radical R 3 and one radical R 4 , together with the carbon atoms that each of the radicals R 3 and R 4 are bound to, form a cyclopropyl or an oxirane ring.
  • W is O. In a further embodiment W is S.
  • V is a direct single bond. In a further embodiment V is a divalent group -NR 2 -.
  • embodiments E.1 to E.396 listed in Table E represent preferred combinations of the embodiments, which are defined above for each of the variables W, V, R 1 , R 2 , R 3 and R 4 in compounds of the formula I.
  • the invention relates to compounds of the formula 1.1 or to compounds of the formula 1.2, or the N-oxides, or the agriculturally acceptable salts thereof,
  • n 0, 1 or 2; and wherein the meaning of the variables W, V, R 1 , R 2 , R 3 , R 4 is as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.396 in Table E; and wherein the variables B and R A are as defined or preferably defined herein for compounds of the formula I.
  • One embodiment relates to compounds of the formula 1.1 or to compounds of the formula 1.2 as defined above, wherein the meaning of the variables W, V, R 1 , R 2 , R 3 , R 4 is as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.396 in Table E; and wherein B is as defined or preferably defined herein for compounds of the formula I, n is 0 or 1 and R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl.
  • Another embodiment relates to compounds of the formula 1.1 or to compounds of the formula 1.2 as defined above, wherein V is -NR 2 - and the meaning of the variables W, R 1 , R 3 , R 4 and R 2 are as defined herein for compounds of the formula I or as preferably defined in embodiments E.133 to E.396 in Table E; and wherein B is as defined or preferably defined herein for compounds of the formula I, n is 0 or 1 and R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl.
  • a further embodiment relates to compounds of the formula 1.1 or to compounds of the formula 1.2 as defined above, wherein V is a direct bond and the meaning of the variables W, R 1 , R 3 and R 4 are as defined herein for compounds of the formula I or as preferably defined in
  • the invention relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c, wherein the variables are as defined or preferably defined herein for compounds of the formula I.
  • One embodiment relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c as defined above, wherein the meaning of the variables W, V, R 1 , R 2 , R 3 , R 4 is as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.396 in Table E; and wherein n is 0 or 1 and R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl.
  • Another embodiment relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c as defined above, wherein V is -NR 2 - and the meaning of the variables W, R 1 , R 2 , R 3 and R 4 are as defined herein for compounds of the formula I or as preferably defined in embodiments E.133 to E.396 in Table E; and wherein n is 0 or 1 and R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl.
  • Another embodiment relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c as defined above, wherein V is a direct bond and the meaning of the variables W, R 1 , R 3 and R 4 are as defined herein for compounds of the formula I or as preferably defined in embodiments E.1 to E.132 in Table E; and wherein n is 0 or 1 and R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl.
  • the invention relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c, wherein R 3 and R 4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl and trifluoromethyl.
  • the invention relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c, wherein R 3 and R 4 are hydrogen.
  • the invention relates to compounds of the formulae 1.1 a, 1.1 b or 1.1 c, or the N-oxides, or the agriculturally acceptable salts thereof, wherein:
  • R A is halogen, Ci-C6-alkyl or Cs-Cs-cycloalkyl
  • n O or l ;
  • W is S or O
  • V is -NR 2 -;
  • R 1 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxyimino-Ci-C4-alkyl, Cs-Cs- cycloalkyl, Cs-Ce-cycloalkenyl or phenyl; and wherein the aliphatic and cyclic groups are unsubstituted or substituted with 1 , 2, 3 or up to the maximum possible number of identical or different radials selected from the group consisting of halogen, cyano,
  • R 2 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, propargyl, Cs-Cs-cycloalkyl, C1-C6- alkylamino or diCi-C6-alkylamino;
  • R 3 and R 4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl and trifluoromethyl; or, if B is -C(R 3 )2-C(R 4 )2-, two radicals R 3 and/or two radicals
  • R 4 which are bound to the same carbon atom, together with said carbon atom, form a cyclopropyl ring; preferably R 3 and R 4 are hydrogen.
  • the present invention relates to compounds of the formulae I.A, I.B, I.C, I.D, I.E, I.F, I.G, I.H, I.J, I.K, I.L, I.M, I.N, 1.0, I.P, I.Q, I.R, I.S, I.T, I.U, I.V, I.W, I.X and I.Y and to their use for controlling phytopathogenic fungi, wherein the variables R 1 and R 2 are as defined or preferably defined herein.
  • Table 1 Compounds of the formula I .A, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.A.A-1 to I.A.A- 2760).
  • R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.A.A-1 to I.A.A- 2760).
  • Table 2 Compounds of the formula I.B, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.B.A-1 to I.B.A- 2760).
  • R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.B.A-1 to I.B.A- 2760).
  • R 1 is /so-propyl and R 2 is ethyl (corresponding to the definition A-684 in Table A) is named I.B.A-684.
  • Table 3 Compounds of the formula I.C, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.C.A-1 to I.C.A- 2760)
  • Table 4 Compounds of the formula I.D, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.D.A-1 to I.D.A- 2760).
  • Table 5 Compounds of the formula I.E, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.E.A-1 to I.E.A- 2760).
  • Table 6 Compounds of the formula I.F, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.F.A-1 to I.F.A- 2760).
  • Table 7 Compounds of the formula I.G, in which R 1 and R 2 for each individual compound corresponds in each case toone line A-1 to A-2760 of Table A (compounds I.G.A-1 to I.G.A- 2760).
  • Table 8 Compounds of the formula I.H, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.H.A-1 to I.H.A- 2760)
  • Table 9 Compounds of the formula I.J, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I. J .A-1 to I.J.A- 2760).
  • Table 10 Compounds of the formula I.K, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.K.A-1 to I.K.A- 2760).
  • Table 1 1 Compounds of the formula I.L, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.L.A-1 to I.L.A- 2760).
  • Table 12 Compounds of the formula I.M, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.M.A-1 to I.M.A- 2760).
  • Table 13 Compounds of the formula I.N, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.N.A-1 to I.N.A- 2760).
  • Table 14 Compounds of the formula I.O, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.O.A-1 to I.O.A- 2760).
  • Table 15 Compounds of the formula I.P, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.P.A-1 to I.P.A- 2760).
  • Table 16 Compounds of the formula I.Q, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.Q.A-1 to I.Q.A- 2760).
  • Table 17 Compounds of the formula I.R, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.R.A-1 to I.R.A- 2760).
  • Table 18 Compounds of the formula I.S, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.S.A-1 to I.S.A- 2760).
  • Table 19 Compounds of the formula IT, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.T.A-1 to I.T.A- 2760).
  • Table 20 Compounds of the formula I.U, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.U.A-1 to I.U.A- 2760).
  • Table 21 Compounds of the formula I.V, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.V.A-1 to I.V.A- 2760).
  • Table 22 Compounds of the formula I.W, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.W.A-1 to I.W.A- 2760).
  • Table 23 Compounds of the formula I.X, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.X.A-1 to I.X.A- 2760).
  • Table 24 Compounds of the formula I.Y, in which R 1 and R 2 for each individual compound corresponds in each case to one line A-1 to A-2760 of Table A (compounds I.Y.A-1 to I.Y.A- 2760).
  • A-33 1 -trifluormethy- H A-61 2-(propylcarb-amoyl)- H lcyclopropyl cyclopropyl
  • A-83 1 -ethylcyclopropyl H
  • A-1 1 1 1 ,2-difluoro-cyclopropyl H
  • A-84 1 -chlorocyclopropyl H
  • A-1 12 1 ,2-dichloro-cyclopropyl H
  • A-336 (3-cyano-phenyl)methyl H A-368 3,3,3-trifluoropropyl CH 3
  • A-337 (4-cyano-phenyl)methyl H A-369 CH 2 CF 2 CF 3 CH 3
  • A-345 (2,6-dichloro- H A-382 1 -isopropyl-cyclopropyl CH 3 phenyl)methyl A-383 1 -propylcyclopropyl CH 3
  • A-675 (3-methyl-phenyl)- CHs
  • A-722 1 -methyl-cyclopropyl CH2CH3
  • A-751 2-(propylcarb-amoyl)- CH2CH3
  • A-725 1 -ethylcyclopropyl CH2CH3
  • A-753 1 ,2-difluorocyclo-propyl CH2CH3
  • A-726 1 -chlorocyclopropyl CH2CH3
  • A-754 1 ,2-dichlorocyclo-propyl CH2CH3
  • A-727 1 -isopropyl-cyclopropyl CH2CH3
  • A-755 2,2-dimethylcyclo- CH2CH3
  • A-729 1 -methoxy-cyclopropyl CH2CH3
  • A-756 2,2-difluorocyclo-propyl CH2CH3
  • A-730 1 -ethoxy-cyclopropyl CH2CH3
  • A-757 2,2-dichlorocyclo-propyl CH2CH3
  • A-731 1 -trifluormethoxy- CH2CH3
  • A-758 1 -fluoro-2-methyl- CH2CH3 cyclopropyl cyclopropyl
  • A-733 1 -(methyl-carbamoyl)- CH2CH3
  • A-760 2-fluoro-1 -methyl- CH2CH3 cyclopropyl cyclopropyl
  • A-734 1 -(ethylcarbamoyl)- CH2CH3
  • A-761 2-chloro-1 -methyl- CH2CH3 cyclopropyl cyclopropyl
  • A-735 1 -(isopropylcarb- CH2CH3 A-762 1 -chloro-2-fluoro- CH2CH3 amoyl)-cyclopropyl cyclopropyl
  • A-736 1 -(propylcarb- CH2CH3 A-763 2-chloro-1 -fluoro- CH2CH3 amoyl)cyclopropyl cyclopropyl
  • A-768 1 -chloro-2,2-difluoro- CH2CH3
  • A-770 1 -methyl-cyclopropyl CH2CH3
  • A-775 1 -isopropylcyclo-propyl CH2CH3
  • A-833 1 H-pyrazol-5-yl CH2CH3 A-865 2-(2,2,2-trifluoro- CH2CH3
  • A-852 4-(2,2,2-trifluoro-ethyl)- CH2CH3 A-883 3-F-4-CI-phenyl CH2CH3 phenyl A-884 3-F-5-CI-phenyl CH2CH3
  • A-1 120 1 -isopropylcyclo-propyl cyp
  • A-1 148 2,2-dimethyl- cyp
  • A-1 121 1 -propylcyclopropyl cyp cyclopropyl
  • A- 25 1 -(difluoro- cyp A- 52 1 -chloro-2-methyl- cyp methyl)cyclopropyl cyclopropyl
  • A-1 130 2-methyl-cyclopropyl cyp
  • A-1 157 2,2-difluoro-1 -methyl- cyp
  • A-1490 1 ,2-dimethyl- allyl A-1516 1 -methylpyrrolidin-2-yl allyl cyclopropyl
  • A-1500 1 -chloro-2-fluoro- allyl
  • A-1501 2-chloro-1 -fluoro- allyl
  • A-1533 4-methyl-phenyl allyl cyclopropyl
  • A-1534 2-ethyl-phenyl allyl
  • A-1502 2,2-difluoro-1 -methyl- allyl
  • A-1535 3-ethyl-phenyl allyl cyclopropyl
  • A-1536 4-ethyl-phenyl allyl
  • A-1504 1 -fluoro-2,2-di-methyl- allyl
  • A-1539 4-isopropyl-phenyl allyl cyclopropyl
  • A-1540 2-(2,2,2-trifluoro-ethyl)- allyl
  • A-1505 1 -chloro-2,2-di-methyl- allyl phenyl
  • A-1506 1 -chloro-2,2-di-fluoro- allyl phenyl
  • A-1514 3-methyl-cyclopentyl allyl
  • A-1550 3-trif I uorom ethoxy- allyl
  • A-1634 3-CI-5-methyl-phenyl ally
  • A-1674 3-CI-5-CN-phenyl allyl
  • A-1636 2-methyl-4-CI-phenyl ally
  • A-1676 2-CN-4-CI-phenyl allyl
  • A-1638 3-methyl-4-CI-phenyl ally
  • A-1678 3-CN-4-CI-phenyl allyl
  • A-1644 3-CI-5-CF 3 -phenyl ally
  • A-1684 CH 2 -(3-pyridyl) allyl
  • A-2133 1 ,2-difluorocyclo-propyl -NHCH3
  • A-21 10 1 -ethoxy-cyclopropyl -NHCH3
  • A-2137 2,2-dichlorocyclo-propyl -NHCH3
  • A-21 13 1 -(methyl-carbamoyl)- -NHCH3
  • A-2140 2-fluoro-1 -methyl- -NHCH3 cyclopropyl cyclopropyl
  • A-21 14 1 -(ethylcarbamoyl)- -NHCH3
  • A-2141 2-chloro-1 -methyl- -NHCH3 cyclopropyl cyclopropyl
  • A-21 15 1 -(isopropylcarb- -NHCH3
  • A-2142 1 -chloro-2-fluoro- -NHCH3 amoyl)-cyclopropyl cyclopropyl
  • A-21 19 2-fluorocyclopropyl -NHCH3 cyclopropyl
  • A-2204 3-methyl-cyclopentyl -NHCHs
  • A-2240 3-trifl uorom ethoxy- -NHCHs
  • A-2206 1 -methylpyrrolidin-2-yl -NHCHs phenyl
  • A-2220 4-CI-phenyl -NHCHs
  • A-2250 4-cyano-phenyl -NHCHs
  • A-2229 4-isopropyl-phenyl -NHCHs A-2259 2-F-3-CI-phenyl -NHCHs

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Abstract

La présente invention concerne des oxadiazoles substitués de formule (I), ou des N-oxydes ou leurs sels utiles sur le plan agricole, et leur utilisation pour lutter contre des champignons phytopathogènes ; un procédé de lutte contre des champignons phytopathogènes nocifs, lequel procédé comprend le traitement des champignons, des plantes, du sol ou des graines à protéger contre des attaques fongiques, avec une quantité efficace d'au moins un composé de formule I ou un N-oxyde ou un sel acceptable sur le plan agricole de celui-ci ; la présente invention concerne également des compositions agrochimiques comprenant au moins un composé de formule (I), ou un N-oxyde, ou un sel acceptable sur le plan agricole de celles-ci, et des compositions agrochimiques comprenant en outre des graines.
PCT/EP2018/063766 2017-06-02 2018-05-25 Oxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes WO2018219797A1 (fr)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
WO2020078732A1 (fr) * 2018-10-17 2020-04-23 Syngenta Crop Protection Ag Dérivés d'oxadiazole microbiocides
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2021175669A1 (fr) * 2020-03-04 2021-09-10 Basf Se Utilisation de 1,2,4-oxadiazoles substitués pour lutter contre des champignons phytopathogènes
US11147275B2 (en) 2017-11-23 2021-10-19 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi

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