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WO2011015524A2 - Dérivés d’hétérocycles fongicides - Google Patents

Dérivés d’hétérocycles fongicides Download PDF

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Publication number
WO2011015524A2
WO2011015524A2 PCT/EP2010/061082 EP2010061082W WO2011015524A2 WO 2011015524 A2 WO2011015524 A2 WO 2011015524A2 EP 2010061082 W EP2010061082 W EP 2010061082W WO 2011015524 A2 WO2011015524 A2 WO 2011015524A2
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WO
WIPO (PCT)
Prior art keywords
substituted
halogen atoms
alkyl
group
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2010/061082
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English (en)
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WO2011015524A3 (fr
Inventor
Christian Beier
Jürgen BENTING
David Bernier
Philippe Desbordes
Christophe Dubost
Pierre-Yves Coqueron
Stéphanie Gary
Daniela Portz
Ulrike Wachendorff-Neumann
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of WO2011015524A2 publication Critical patent/WO2011015524A2/fr
Publication of WO2011015524A3 publication Critical patent/WO2011015524A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to aryloxyalkyl-heterocycle derivatives, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.
  • Q can be selected in a list of 7 various heterocycle groups substituted by various carbonylaminoderivatives and A can be selected in a list of 7various 5-menbered heterocycle groups.
  • the compounds disclosed in these two documents do not prove to provide a comparable utility than the compounds according to the invention.
  • the present invention provides aryloxyalkyl-heterocycle derivatives of formula (I)
  • Q 1 represents N or CY 3 ;
  • Y 1 , Y 2 , Y 3 and Y 4 independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, hydroxycarbonyl, C- ⁇ -C 8 -alkoxycarbonyl, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde 0-(C 1 -C 8 - alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro- ⁇ 6 -sulphenyl group, a formylamino group, substituted or non-substituted d-C 8 -alkoxyamino group, substituted or non-substituted N-C- ⁇ -C 8 -alkyl-(C- ⁇ -C 8
  • n 1 , 2, 3 or 4 ;
  • R 1 and R 2 independently represent a hydrogen atom, a halogen atom, a cyano group, substituted or non-substituted C- ⁇ -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted C- ⁇ -C 8 -halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted Ci-C 8 -alkoxy, substituted or non-substituted Ci-C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C 2 -C 8
  • T represents a hydrogen or a substituted or non-substituted heterocyclyl group that is selected in the list consisting of T 1 to T 32 :
  • X 1 to X 4 independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(C- ⁇ -C 8 -alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro- ⁇ 6 -sulphenyl group, a formylamino group, substituted or non-substituted C-i-Cs-alkoxyamino group, substituted or non-substituted N- Ci-C 8 -alkyl-(Ci-C 8 -alkoxy)-amino group, substituted or non-substituted (d-C 8 -alkylamino
  • W 1 independently represents a hydrogen atom, a formyl group, a substituted or non- substituted carbaldehyde O-(C- ⁇ -C 8 -alkyl)oxime, a carbamoyl group, a N-hydroxycarbamoyl group, a formylamino group, substituted or non-substituted d-C 8 -alkyl, substituted or non-substituted tri(Ci-C 8 -alkyl)silyl-Ci-C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non- substituted tri(Ci-C 8 -alkyl)silyl-C 3 -C 8 -cycloalkyl, substituted or non-substituted Ci-C 8 - halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C 3 -C 8 -
  • Ci-C 8 -alkynyl substituted or non-substituted Ci-C 8 -alkylamino, substituted or non-substituted di- Ci-C 8 -alkylamino, substituted or non-substituted Ci-C 8 -alkoxy, substituted or non-substituted Ci- C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C 2 -C 8 -alkenyloxy, substituted or non-substituted C 2 -C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, substituted or non-substituted C 2 -C 8 -alkynyloxy, substituted or non-substituted C 3 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, substituted or non-substituted Ci-C 8 -alkyl,
  • Z ⁇ Z 2 , Z 3 , Z 4 Z 5 , Z 6 , Z 7 , Z 8 and Z 9 independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde O-(C- ⁇ -C 8 -alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro- ⁇ 6 -sulphenyl group, a formylamino group, substituted or non-substituted Ci-C 8 -alkoxyamino group, substituted or non-substituted N-C- ⁇ -C 8 -alkyl-(C- ⁇ -C 8 -alkoxy)-amino
  • K 1 and K 2 independently represent a hydrogen atom, a formyl group, a substituted or non- substituted carbaldehyde O-(C- ⁇ -C 8 -alkyl)oxime, a carbamoyl group, a N-hydroxycarbamoyl group, a formylamino group, substituted or non-substituted C- ⁇ -C 8 -alkyl, substituted or non-substituted tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non- substituted tri(C 1 -C 8 -alkyl)silyl-C 3 -C 8 -cycloalkyl, substituted or non-substituted C 1 -C 8 - halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substitute
  • G 1 and G 2 are independently selected in the list consisting of oxygen, sulfur, NR 3 , N-OR 4 and N-NR 5 R 6 wherein R 3 to R 6 independently represent a hydrogen atom, a halogen atom, a cyano group, substituted or non-substituted C- ⁇ -C 8 -alkyl, substituted or non-substituted C 3 -C 8 - cycloalkyl, substituted or non-substituted C- ⁇ -C 8 -halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2 -C 8 - alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted C- ⁇ -C 8 -alkoxy, substituted or non-substituted
  • Y 5 to Y 8 independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a formyl group, a substituted or non- substituted carbaldehyde O-(Ci-C 8 -alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a pentafluoro- ⁇ 6 -sulphenyl group, a formylamino group, substituted or non-substituted C- ⁇ -C 8 -alkoxyamino group, substituted or non-substituted C 1 - C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted Ci-C 8 - halogen
  • any of the compounds according to the invention can exist as one or more stereoisomers depending on the number of stereogenic units (as defined by the IUPAC rules) in the compound.
  • the invention thus relates equally to all the stereoisomers and to the mixtures of all the possible stereoisomers, in all proportions.
  • the stereoisomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.
  • halogen means fluorine, chlorine, bromine or iodine ;
  • heteroatom can be nitrogen, oxygen or sulphur ; • unless indicated otherwise, a group or a substituent that is substituted according to the invention can be substituted by one or more of the following groups or atoms: a halogen atom, a nitro group, a hydroxy group, a cyano group, an amino group, a sulphenyl group, a pentafluoro- ⁇ 6 - sulphenyl group, a formyl group, a substituted or non-substituted carbaldehyde 0-(Ci-C 8 - alkyl)oxime, a formyloxy group, a formylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, a formylamino group, a (hydroxyimino)-C- ⁇ -C 6 -alkyl group, a C- ⁇ -C 8 -alkyl, a tri(Ci-C 8 - alky
  • halogen atoms a Ci-C 8 -alkylaminocarbonyloxy, a di-Ci-C 8 -alkylaminocarbonyloxy, a Ci-C 8 - alkyloxycarbonyloxy, a Ci-C 8 -alkylsulphenyl, a Ci-C 8 -halogenoalkylsulphenyl having 1 to 5 halogen atoms, a Ci-C 8 -alkylsulphinyl, a Ci-C 8 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, a Ci-C 8 -alkylsulphonyl, a Ci-C 8 -halogenoalkylsulphonyl having 1 to 5 halogen atoms, a Ci- C 8 -alkylaminosulfamoyl, a di-Ci-C 8 -alkylaminosulfamoyl, a (d-
  • aryl means phenyl or naphthyl
  • heterocyclyl means saturated or unsaturated A-, 5-, 6- or 7-membered ring comprising up to 4 heteroatoms selected in the list consisting of N, O, S.
  • Preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein Y 1 , Y 2 , Y 3 and Y 4 independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or non- substituted carbaldehyde O-(Ci-C 8 -alkyl)oxime, substituted or non-substituted Ci-C 8 -alkyl, substituted or non-substituted Ci-C 8 -halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C 8 - alkoxy, substituted or non-substituted Ci-C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted phenoxy, substituted or non-substituted aryl.
  • More preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein Y 1 , Y 2 , Y 3 and Y 4 independently represent a hydrogen atom, a halogen atom, substituted or non-substituted Ci-C 8 -alkyl, substituted or non-substituted Ci-C 8 -halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted Ci-C 8 -alkoxy.
  • R 1 and R 2 independently represent a hydrogen atom, a halogen atom, substituted or non-substituted C 1 -C 8 - alkyl.
  • More preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein R 1 and R 2 independently represent a hydrogen atom.
  • Preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein T represents a substituted or non-substituted heterocyclyl group that is selected in the list consisting of T 27 to T 32 .
  • More preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein T represents a substituted or non-substituted heterocyclyl group that is selected in the list consisting of T 31 tO T 32 .
  • Preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein X 1 to X 4 independently represent a hydrogen atom, a halogen atom, a substituted or non-substituted carbaldehyde
  • O-(Ci-C 8 -alkyl)oxime substituted or non-substituted Ci-C 8 -alkyl, substituted or non-substituted C 3 -C 8 - cycloalkyl, substituted or non-substituted Ci-C 8 -halogenoalkyl having 1 to 5 halogen atoms, substituted or non-substituted C 3 -C 8 -halogenocycloalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted Ci-C 8 -alkoxy, substituted or non-substituted Ci-C 8 -halogenoalkoxy having 1 to 5 halogen atoms.
  • More preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein X 1 to X 4 independently represent a hydrogen atom, a halogen atom, substituted or non-substituted Ci-C 8 -alkyl. Even more preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein X 1 to X 4 independently represent a methyl group.
  • Preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein W 1 represents a hydrogen atom, a halogen atom, a cyano group, substituted or non-substituted Ci-C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted Ci-C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non- substituted d-C 8 -alkoxy, substituted or non-substituted d-C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted phenoxy, substituted or non-substituted aryl, substituted or non- substituted
  • W 1 represents a hydrogen atom, a halogen atom, methyl, ethyl, isopropyl, isobutyl, terbutyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy and cyano.
  • W 1 represents a hydrogen atom, a halogen atom, methyl, ethyl, isopropyl, isobutyl, terbutyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy and cyano.
  • A is selected in the list consisting of A 1 to A 58 .
  • A is selected in the list consisting of A 2 , A 6 , A 8 , A 11 to A 18 .
  • Other preferred compounds of formula (I) and (Ia) to (Ic) according to the invention are those wherein Z 1 represents a hydrogen atom, a halogen atom, an amino group, a formylamino group, substituted or non- substituted Ci-C 8 -alkoxyamino group, substituted or non-substituted N-Ci-C 8 -alkyl-(Ci-C 8 -alkoxy)-amino group, substituted or non-substituted Ci-C 8 -alkyl, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 - alkynyl, substituted or non-substituted d-C 8 -alkylamino,
  • Z 1 represents an amino group, a halogen atom, a formylamino group, a C 2 -C 8 -alkenyl, substituted or non- substituted C 2 -C 8 -alkynyl, substituted or non-substituted d-C 8 -alkylannino, substituted or non-substituted (Ci-C 8 -alkoxycarbonyl)annino, substituted or non-substituted (C 3 -C 8 -cycloalkoxycarbonyl)annino, substituted or non-substituted (C 2 -C 8 -alkenyloxycarbonyl)annino, substituted or non-substituted (C 3 -C 8 - alkynyloxycarbonyl)amino, substituted or non-substituted d-Cs-al
  • Z 2 to Z 9 independently represent a hydrogen atom, a halogen atom, a cyano group, substituted or non- substituted d-C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted C 1 - C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 - alkynyl, substituted or non-substituted d-C 8 -alkoxy, substituted or non-substituted d-C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted phenoxy, substituted or non-substituted aryl, substitute
  • Z 2 to Z 9 are independently selected in the list consisting of hydrogen, halogen, methyl, ethyl, isopropyl, isobutyl, terbutyl, trifluoromethyl, difluoromethyl, allyl, ethynyl, propargyl, cyclopropyl, methoxy, trifluoromethoxy, acetyl, and cyano.
  • K 1 and K 2 are independently selected in the list consisting of hydrogen, methyl, ethyl, isopropyl, isobutyl, terbutyl, allyl, propargyl, cyclopropyl, acetyl, trifluoroacetyl and mesyl.
  • Preferred compounds of formula (Ia) to (Ic) according to the invention are those wherein Y 5 to Y 8 independently represent a hydrogen atom, a halogen atom, substituted or non-substituted Ci-C 8 -alkyl. More preferred compounds of formula (Ia) to (Ic) according to the invention are those wherein Y 5 to Y 8 independently represent a hydrogen atom or a fluorine atom.
  • preferred features of A with preferred features of one or more of T, Q 1 , Q 2 , Y 1 , Y 2 , R 1 , R 2 and n ; preferred features of T with preferred features of one or more of A, Q 1 , Q 2 , Y 1 , Y 2 , R 1 , R 2 and n ; preferred features Q 1 with preferred features of one or more of A, T, Q 2 , Y 1 , Y 2 , R 1 , R 2 and n ; - preferred features Q 2 with preferred features of one or more of A, T, Q 1 , Y 1 , Y 2 , R 1 , R 2 and n ; preferred features Y 1 with preferred features of one or more of A, T, Q 1 , Q 2 , Y 2 , R 1 , R 2 and n ; preferred features Y 2 with preferred features of one or more of A, T, Q 1 , Q 2 , Y 2 , R 1 , R 2 and n ; preferred features
  • the said preferred features can also be selected among the more preferred features of each of A, T, Q 1 , Q 2 , Y 1 , Y 2 , R 1 , R 2 and n ; so as to form most preferred subclasses of compounds according to the invention.
  • the present invention also relates to a process for the preparation of compounds of formula (I) and (Ia) to (Ic).
  • T, A, Q 1 , Q 2 , Y 1 , Y 2 , R 1 , R 2 and n are as herein-defined and LG represents a leaving group.
  • Suitable leaving groups can be selected in the list consisting of a halogen atom or other customary nucleofugal groups such as triflate, mesylate, or tosylate.
  • the present invention also relates to a fungicide composition
  • a fungicide composition comprising an effective and non-phytotoxic amount of an active compound of formula (I).
  • fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) as herein defined and an agriculturally acceptable support, carrier or filler.
  • the term "support” denotes a natural or synthetic organic or inorganic compound with which the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant.
  • This support is thus generally inert and should be agriculturally acceptable.
  • the support can be a solid or a liquid.
  • suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports can also be used.
  • composition according to the invention can also comprise additional components.
  • the composition can further comprise a surfactant.
  • the surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants.
  • polyacrylic acid salts lignosulphonic acid salts, phenolsulphonic or naphthalenesulphonic acid salts
  • polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines substituted phenols (in particular alkylphenols or ary
  • surfactant content can be comprised from 5% to 40% by weight of the composition.
  • additional components can also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents.
  • the active compounds can be combined with any solid or liquid additive, which complies with the usual formulation techniques.
  • composition according to the invention can contain from 0.05 to 99% by weight of active compound, preferably 10 to 70% by weight.
  • compositions according to the invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure),gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
  • These compositions include not only compositions which are ready to be applied to the plant or seed to
  • the compounds according to the invention can also be mixed with one or more insecticide, fungicide, bactericide, attractant, acaricide or pheromone active substance or other compounds with biological activity.
  • the mixtures thus obtained have a broadened spectrum of activity.
  • the mixtures with other fungicide compounds are particularly advantageous.
  • the composition according to the invention comprising a mixture of a compound of formula (I) with a bactericide compound can also be particularly advantageous.
  • fungicide mixing partners can be selected in the following lists:
  • Inhibitors of the ergosterol biosynthesis for example (1.1 ) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (1 16255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11 ) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6
  • inhibitors of the respiratory chain at complex I or II for example (2.1 ) bixafen (581809-46-3), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram
  • inhibitors of the respiratory chain at complex III for example (3.1 ) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3) azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5) dimoxystrobin (141600-52-4), (3.6) enestroburin (238410-11-2) (WO 2004/058723), (3.7) famoxadone (131807-57-3) (WO 2004/058723), (3.8) fenamidone (161326-34-7) (WO 2004/058723), (3.9) fluoxastrobin (361377-29-9) (WO 2004/058723), (3.10) kresoxim-methyl (143390-89-0) (WO 2004/058723), (3.11 ) metominostrobin (133408-50-1 ) (WO 2004/058723), (3.12) orysastrobin (18
  • Inhibitors of the mitosis and cell division for example (4.1 ) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7) fuberidazole (3878-19-1 ), (4.8) pencycuron (66063- 05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11 ) thiophanate (23564- 06-9), (4.12) zoxamide (156052-68-5), (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine (2147)
  • Inhibitors of the amino acid and/or protein biosynthesis for example , (7.1 ) andoprim (23951-85-1 ), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0) and salts thereof.
  • Inhibitors of the ATP production for example (8.1 ) fentin acetate (900-95-8), (8.2) fentin chloride (639- 58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6).
  • Inhibitors of the cell wall synthesis for example (9.1 ) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (21 1867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (1 1113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0).
  • Inhibitors of the lipid and membrane synthesis for example (10.1 ) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-
  • (11 ) Inhibitors of the melanine biosynthesis for example (11.1 ) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1 ) and (11.6) tricyclazole (41814-78-2).
  • Inhibitors of the nucleic acid synthesis for example (12.1 ) benalaxyl (71626-11-4), (12.2) benalaxyl-M (kiralaxyl) (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazol (10004-44-1 ), (12.9) metalaxyl (57837-19-1 ), (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11 ) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4).
  • Inhibitors of the signal transduction for example (13.1 ) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1 ), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809- 16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44-8).
  • a method for controlling the phytopathogenic fungi of plants, crops or seeds characterized in that an agronomically effective and substantially non-phytotoxic quantity of a fungicide composition according to the invention is applied as seed treatment, foliar application, stem application, drench or drip application (chemigation) to the seed, the plant or to the fruit of the plant or to soil or to inert substrate (e.g. inorganic substrates like sand, rockwool, glasswool; expanded minerals like perlite, vermiculite, zeolite or expanded clay), Pumice, Pyroclastic materials or stuff, synthetic organic substrates (e.g. polyurethane) organic substrates (e.g.
  • a liquid substrate e.g. floating hydroponic systems, Nutrient Film Technique, Aeroponics
  • fungicide composition which is the subject of the invention can be applied by means of various methods of treatment such as:
  • the method according to the invention can either be a curing, preventing or eradicating method.
  • a composition used can be prepared beforehand by mixing the two or more active compounds according to the invention.
  • the dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously
  • a lower dose can offer adequate protection.
  • the optimum dose usually depends on several factors, for example on the type of phytopathogenic fungus to be treated, on the type or level of development of the infested plant, on the density of vegetation or alternatively on the method of application.
  • the crop treated with the pesticide composition or combination according to the invention is, for example, grapevine, but this could be cereals, vegetables, lucerne, soybean, market garden crops, turf, wood, tree or horticultural plants.
  • the method of treatment according to the invention can also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots.
  • the method of treatment according to the invention can also be useful to treat the over-ground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant.
  • Solanaceae sp. for instance tomatoes
  • Solanaceae sp. for instance tomatoes
  • ⁇ liaceae sp. for instance lettuces
  • Umbelliferae sp. for instance lettuces
  • Umbelliferae sp. for instance lettuces
  • Umbelliferae sp. for instance lettuces
  • Cilionaceae sp. for instance peas
  • Rosaceae sp. for instance strawberries
  • major crops such as Graminae sp. (for instance maize, lawn or cereals such as wheat, rice, barley and triticale), Asteraceae sp. (for instance sunflower), Cruciferae sp.
  • the composition according to the invention can also be used against fungal diseases liable to grow on or inside timber.
  • the term "timber" means all types of species of wood and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood and plywood.
  • the method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means.
  • Powdery mildew diseases such as :
  • Blumeria diseases caused for example by Blumeria graminis ;
  • Podosphaera diseases caused for example by Podosphaera leucotricha ;
  • Sphaerotheca diseases caused for example by Sphaerotheca fuliginea ;
  • Uncinula diseases caused for example by Uncinula necator ;
  • Gymnosporangium diseases caused for example by Gymnosporangium sabinae ;
  • Hemileia diseases caused for example by Hemileia vastatrix ;
  • Phakopsora diseases caused for example by Phakopsora pachyrhizior Phakopsora meibomiae ;
  • Puccinia diseases caused for example by Puccinia recondita ;
  • Uromyces diseases caused for example by Uromyces appendiculatus ;
  • Oomycete diseases such as :
  • Bremia diseases caused for example by Bremia lactucae ;
  • Peronospora diseases caused for example by Peronospora pisi or P. brassicae ;
  • Phytophthora diseases caused for example by Phytophthora infestans ;
  • Plasmopara diseases caused for example by Plasmopara viticola ;
  • Pseudoperonospora diseases caused for example by Pseudoperonospora humuli or
  • Pythium diseases caused for example by Pythium ultimum ;
  • Leafspot, leaf blotch and leaf blight diseases such as :
  • Alternaria diseases caused for example by Alternaria solani ;
  • Cercospora diseases caused for example by Cercospora beticola ;
  • Cladiosporum diseases caused for example by Cladiosporium cucumerinum ;
  • Cochliobolus diseases caused for example by Cochliobolus sativus ;
  • Colletotrichum diseases caused for example by Colletotrichum lindemuthanium ;
  • Cycloconium diseases caused for example by Cycloconium oleaginum ;
  • Diaporthe diseases caused for example by Diaporthe citri ;
  • Elsinoe diseases caused for example by Elsinoe fawcettii ;
  • Gloeosporium diseases caused for example by Gloeospohum laeticolor ;
  • Glomerella diseases caused for example by Glomerella cingulata ;
  • Guignardia diseases caused for example by Guignardia bidwelli ;
  • Leptosphaeria diseases caused for example by Leptosphaeha maculans ; Leptosphaeha nodorum ;
  • Magnaporthe diseases caused for example by Magnaporthe grisea ;
  • Mycosphaerella diseases caused for example by Mycosphaerella graminicola ; Mycosphaerella arachidicola ; Mycosphaerella fijiensis ;
  • Phaeosphaeria diseases caused for example by Phaeosphaeria nodorum ;
  • Pyrenophora diseases caused for example by Pyrenophora teres ;
  • Ramularia diseases caused for example by Ramularia collo-cygni ;
  • Rhynchosporium diseases caused for example by Rhynchosporium secalis ;
  • Septoria diseases caused for example by Septoria apii or Septoria lycopercisi ;
  • Typhula diseases caused for example by Typhula incarnata ;
  • Venturia diseases caused for example by Venturia inaequalis ;
  • Root and stem diseases such as :
  • Fusarium diseases caused for example by Fusarium oxysporum ;
  • Gaeumannomyces diseases caused for example by Gaeumannomyces graminis ;
  • Rhizoctonia diseases caused for example by Rhizoctonia solani ;
  • Tapesia diseases caused for example by Tapesia acuformis ;
  • Thielaviopsis diseases caused for example by Thielaviopsis basicola ;
  • Ear and panicle diseases such as :
  • Alternaria diseases caused for example by Alternaria spp. ;
  • Aspergillus diseases caused for example by Aspergillus flavus ;
  • Cladosporium diseases caused for example by Cladosporium spp. ;
  • Claviceps diseases caused for example by Claviceps purpurea ;
  • Fusarium diseases caused for example by Fusarium culmorum ;
  • Gibberella diseases caused for example by Gibberella zeae ;
  • Monographella diseases caused for example by Monographella nivalis ; Smut and bunt diseases such as :
  • Sphacelotheca diseases caused for example by Sphacelotheca reiliana ;
  • Tilletia diseases caused for example by Tilletia caries ;
  • Urocystis diseases caused for example by Urocystis occulta ;
  • Ustilago diseases caused for example by Ustilago nuda ;
  • Aspergillus diseases caused for example by Aspergillus flavus ;
  • Botrytis diseases caused for example by Botrytis cinerea ;
  • Penicillium diseases caused for example by Penicillium expansum ;
  • Sclerotinia diseases caused for example by Sclerotinia sclerotiorum ;
  • Verticilium diseases caused for example by Verticilium alboatrum ;
  • Seed and soilborne decay, mould, wilt, rot and dam ping-off diseases Seed and soilborne decay, mould, wilt, rot and dam ping-off diseases :
  • Aphanomyces diseases caused for example by Aphanomyces euteiches Ascochyta diseases, caused for example by Ascochyta lentis
  • Cladosporium diseases caused for example by Cladosporium herbarum
  • Cochliobolus diseases caused for example by Cochliobolus sativus
  • Colletotrichum diseases caused for example by Colletotrichum coccodes
  • Fusarium diseases caused for example by Fusarium culmorum
  • Gibberella diseases caused for example by Gibberella zeae
  • Macrophomina diseases caused for example by Macrophomina phaseolina
  • Monographella diseases caused for example by Monographella nivalis
  • Penicillium diseases caused for example by Penicillium expansum
  • Phoma diseases caused for example by Phoma lingam
  • Phomopsis diseases caused for example by Phomopsis sojae
  • Phytophthora diseases caused for example by Phytophthora cactorum
  • Pyrenophora diseases caused for example by Pyrenophora graminea Pyricularia diseases, caused for example by Pyricularia oryzae;
  • Pythium diseases caused for example by Pythium ultimum
  • Rhizopus diseases caused for example by Rhizopus oryzae
  • Sclerotium diseases caused for example by Sclerotium rolfsii;
  • Typhula diseases caused for example by Typhula incarnata
  • Verticillium diseases caused for example by Verticillium dahliae ;
  • Canker, broom and dieback diseases such as : Nectria diseases, caused for example by Nectria galligena ;
  • Blight diseases such as :
  • Leaf blister or leaf curl diseases such as :
  • Taphrina diseases caused for example by Taphrina deformans ;
  • Esca diseases caused for example by Phaemoniella clamydospora ;
  • Eutypa dyeback caused for example by Eutypa lata ;
  • Botrytis diseases caused for example by Botrytis cinerea ;
  • Rhizoctonia diseases caused for example by Rhizoctonia solani
  • Helminthosporium diseases caused for example by Helminthosporium solani.
  • the treatment according to the invention may also result in superadditive
  • the active compound combinations according to the invention may also have a strengthening effect in plants.
  • Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted phytopathogenic fungi and/ or microorganisms and/or viruses, the treated plants display a substantial degree of resistance to these unwanted phytopathogenic fungi and/ or microorganisms and/or viruses.
  • phytopathogenic fungi and/ or microorganisms and/or viruses are to be understood as meaning phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment.
  • the period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
  • Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).
  • Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
  • Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozon exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may also be treated according to the invention are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
  • Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stress factors. Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome.
  • Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering.
  • a particularly useful means of obtaining male-sterile plants is described in WO 1989/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 1991/002069).
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in US 5,776,760 and US 5,463,175.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782.
  • Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described in for example WO 2001/024615 or WO 2003/013226.
  • herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition.
  • One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in US 5,561 ,236; US 5,648,477;
  • hydroxyphenylpyruvatedioxygenase HPPD
  • Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate.
  • Plants tolerant to HPPD-inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO 1999/024585 and WO 1999/024586.
  • Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 1999/034008 and WO 2002/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme prephenate dehydrogenase in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928.
  • Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS enzyme also known as acetohydroxyacid synthase, AHAS
  • AHAS acetohydroxyacid synthase
  • imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 , and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 2007/024782.
  • plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in US 5,084,082, for rice in WO 1997/41218, for sugar beet in US 5,773,702 and WO 1999/057965 , for lettuce in US 5,198,599, or for sunflower in WO 2001/065922.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • An "insect-resistant transgenic plant”, as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:
  • an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins listed by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, updated by Crickmore et al. (2005) at the Bacillus thuringiensis toxin nomenclature, online at:
  • insecticidal portions thereof e.g., proteins of the Cry protein classes CrylAb, CryiAc, Cry1 F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof; or
  • a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1 ) above or a hybrid of the proteins of 2) above, e.g., the Cry1A.1O5 protein produced by corn event MON98034 (WO 2007/027777); or
  • VIP vegetative insecticidal
  • Plants or plant cultivars which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include: a. plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose)polymerase (PARP) gene in the plant cells or plants as described in WO 2000/004173 or WO2006/045633 or PCT/EP07/004142. b.
  • PARP poly(ADP-ribose)polymerase
  • plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells as described e.g. in WO 2004/090140.
  • plants which contain a stress tolerance enhancing transgene coding for a plant- functional enzyme of the nicotinamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphoribosyltransferase as described e.g.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as :
  • transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.
  • a modified starch which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.
  • transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581 , WO 1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO
  • transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification.
  • Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO 1998/039460, and WO 1999/024593, plants producing alpha 1 ,4 glucans as disclosed in WO 1995/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 1997/047806, WO 1997/047807, WO
  • Plants or plant cultivars which can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 1998/000549
  • Plants such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acteylglucosaminetransferase gene including nodC and chitinsynthase genes as described in WO2006/136351
  • Plants or plant cultivars which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants contain a mutation imparting such altered oil characteristics and include:
  • transgenic plants which may be treated according to the invention are plants which comprise one or more genes which encode one or more toxins, such as the following which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), BiteGard® (for example maize), Bt-Xtra® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B®(cotton), NatureGard® (for example maize), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, soya beans
  • KnockOut® for example maize
  • BiteGard® for example maize
  • Bt-Xtra® for example maize
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example maize
  • herbicide-tolerant plants examples include maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize).
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • Clearfield® for example maize.
  • Step 2 To 5ml of tetrahydrofuran were added3.5mg (0.01 mmol) of copper iodide, 143mg (1.49mnnol) of heptyne, 150mg (0.37mmol) of 5- ⁇ 2-[(2-bromo-1 ,3-thiazol-4-yl)methoxy]-1-naphthyl ⁇ -1-methyl-1 H-tetrazole (as obtained in step 1 ), 193mg (1.49mnnol) of N,N-diisopropylethylamine and 21.6mg (O.OI mmol) of tetrakis(triphenylphosphine)palladium(0) in a sealed tube under argon atmosphere. The reaction mixture was left to stand at room temperature overnight. Filtration on chemelut, and solvent evaporation of the filtatre were performed before the product was purified with HPLC.
  • table 1 A in (I) can have for example the values A1 , A2 and Z:
  • M+H means the molecular ion peak, plus or minus 1 a.m.u. (atomic mass unit) respectively, as observed in mass spectroscopy and M (APCI+) means the molecular ion peak as it was found via positive atmospheric pressure chemical ionization in mass spectroscopy.
  • Emulsifier 1 part by weight of Alkylarylpolyglycolether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Example 4 (80 %), 13 (95 %), 17 (95 %), 18 (80 %), 20 (80 %), 21 (95 %), 22 (70 %), 25 (70 %) and 28 (90 %).

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Abstract

La présente invention a pour objet des dérivés d’hétérocycle d’hydroxymoyle, leur procédé de préparation, des composés intermédiaires pour leur préparation, leur utilisation en tant qu’agents actifs fongicides, en particulier sous la forme de compositions fongicides, et des procédés pour la lutte contre les champignons phytopathogènes, notablement des plantes, au moyen de ces composés ou de ces compositions.
PCT/EP2010/061082 2009-08-03 2010-07-30 Dérivés d’hétérocycles fongicides Ceased WO2011015524A2 (fr)

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CN109071495A (zh) * 2016-04-13 2018-12-21 瑞戴格作物保护公司 农业化学品
JP2020505347A (ja) * 2017-01-13 2020-02-20 レダッグ クロップ プロテクション リミテッド 殺真菌剤としてのチオベンゾイミダゾール
US11014908B2 (en) 2018-11-29 2021-05-25 Pfizer Inc. Chemical compounds

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