WO2013113720A1 - Composés de pyrimidine fongicides - Google Patents

Composés de pyrimidine fongicides Download PDF

Info

Publication number
WO2013113720A1
WO2013113720A1 PCT/EP2013/051725 EP2013051725W WO2013113720A1 WO 2013113720 A1 WO2013113720 A1 WO 2013113720A1 EP 2013051725 W EP2013051725 W EP 2013051725W WO 2013113720 A1 WO2013113720 A1 WO 2013113720A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
individualized compound
compounds
haloalkoxy
Prior art date
Application number
PCT/EP2013/051725
Other languages
English (en)
Inventor
Wassilios Grammenos
Ian Robert CRAIG
Nadege Boudet
Bernd Müller
Jochen Dietz
Erica May Wilson LAUTERWASSER
Jan Klaas Lohmann
Jurith Montag
Original Assignee
Basf Se
Basf Schweiz Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Basf Se, Basf Schweiz Ag filed Critical Basf Se
Publication of WO2013113720A1 publication Critical patent/WO2013113720A1/fr

Links

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

Definitions

  • the present invention relates to fungicidal pyrimidine compounds, to their use and to methods for combating phytopathogenic fungi.
  • the present invention also relates to seeds treated with at least one such compound.
  • the invention relates to processes for preparing compounds of formula I and intermediates as well as processes for the preparation of such intermediates.
  • WO 1998/003272 describes a process for the preparation of 4-amino-5-chloro-6-(1 -fluoro- ethyl)pyrimidine compounds, which are pest controlling agents for agricultural and horticultural use.
  • WO 1997/028133 discloses acylated 4-amino and 4-hydrazinopyrimidines and their use as pesticides.
  • WO 1995/018795 relates to N-(4-pyrimidinyl)amide pesticides and WO 2007/099326 A1 discloses certain quinoline derivatives as pharmaceuticals.
  • the compounds according to the present invention differ from those described in the abovementioned publications by the specific R b substitution on the phenyl ring as defined herein and by the specific Het group.
  • EP 665225 A1 relates to 4-phenethylamino pyrimidine derivatives, which are useful for chemical control of noxious organisms and EP 264217 A2 relates to N-(4-pyrimidinyl)aryl- alkylamine pesticides, inter alia disclosing N-(4-pyrimidinyl)phenylethylamines, but these publications do not mention specifically the combination of the specific R b substitution and the linker -O- together with the group Het as defined herein.
  • the fungicidal activity of known fungicidal compounds is unsatisfactory. Based on this, it was an object 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 use of substituted pyrimidine compounds of formula I having good fungicidal activity against phytopathogenic harmful fungi.
  • R a5 , R a6 independently of each other are hydrogen, halogen, CN , NO2, OH , SH , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci- C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl,
  • R A , R B independently of one another are hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4- alkynyl, phenyl, benzyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkenyl or
  • R' is hydrogen, OH, NH 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl,
  • R" is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl or
  • R'" is hydrogen or Ci-C4-alkyl; is hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
  • Ci-C4-alkoxy-Ci-C4-alkyl Ci-C4-haloalkoxy-Ci-C4-alkyl, C2-C4-alkenyl,
  • R 2 independently of each other are hydrogen, halogen, OH, CN, Ci-C4-alkyl,
  • Ci-C4-haloalkyl Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-halo- alkoxy-Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl,
  • phenyl moiety of benzyl is unsubstituted or carries 1 , 2 , 3, 4 or 5 substituents selected from the group consisting of CN, halogen, Ci-C4-alkyl,
  • Ci-C4-haloalkyl Ci-C4-alkoxy, Ci-C4-haloalkoxy, (Ci-C4-alkoxy)carbonyl and di(Ci-C4- alkyl)aminocarbonyl, or two radicals R 1 and R 2 that are bound to the same carbon atom form together with said carbon atom a saturated or partially unsaturated
  • Ci-C4-haloalkyl Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
  • R b are identical or different; is a 5- or 6-membered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S and wherein the heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 identical or different groups R c :
  • R c is halogen, CN, NO2, d-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, d-Ce-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl,
  • Ci-C6-alkylsulfonyl Ci-C6-haloalkylsulfonyl, Ci-C6-alkoxy-Ci-C4-alkyl,
  • R e is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy; and the N-oxides and the agriculturally acceptable salts thereof.
  • the present invention furthermore relates to processes for preparing the compounds I.
  • the present invention furthermore relates to intermediates such as compounds of formulae II, III, lla and Ilia.
  • the compounds of the present invention are useful for combating harmful fungi. Therefore the present invention furthermore relates to a method for combating harmful fungi, which process comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of formula I or of an N- oxide or an agriculturally acceptable salt thereof.
  • the present invention also relates to seed comprising a compound of formula I, or an N-oxide or an agriculturally acceptable salt thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.
  • the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or diastereomers and their mixtures are subject matter of the present invention.
  • Agriculturally useful salts of the compounds I encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of the compounds I.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compounds of formula I can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
  • inventive compounds I can be prepared by various routes in analogy to prior art processes and, advantageously, by the synthesis shown in the following schemes and in the experimental part of this application.
  • a 4-halopyrimidine compound II, wherein Hal is halogen, preferably CI or F, can be reacted with a suitable phenethyl amine compound III, wherein X is -CR 3 R 4 -, to obtain a compound I according to the present invention, wherein X is -CR 3 R 4 -, as shown in Scheme 1 :
  • this reaction is carried out at temperatures of from 0 to 200°C, preferably from 50 to 170°C, preferably in an inert organic solvent and preferably in presence of a base or a catalyst or a combination of a base and a catalyst (e.g. NaF, KF, LiF, NaBr, KBr, LiBr, Nal, Kl, Lil and ionic liquids, such as imidazolium catalysts).
  • a base or a catalyst or a combination of a base and a catalyst e.g. NaF, KF, LiF, NaBr, KBr, LiBr, Nal, Kl, Lil and ionic liquids, such as imidazolium catalysts.
  • Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene;
  • halogenated hydro-carbons such as chlorobenzene, dichlorobenzene; ethers such as dioxane, anisole and tetra-hydrofuran (THF); nitriles such as acetonitrile and propionitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert.
  • -butyl methyl ketone alcohols such as ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol; and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF), dimethyl acetamide, N-methyl-2-pyrrolidone (NMP), N- ethyl-2-pyrrolidone (NEP) and acetic acid ethyl ester, preferably DMSO, DMF, dimethyl acetamide, NMP, or NEP. Particular preference is given to NMP. It is also possible to use mixtures of the solvents mentioned.
  • DMSO dimethylformamide
  • NMP N-methyl-2-pyrrolidone
  • NEP N- ethyl-2-pyrrolidone
  • acetic acid ethyl ester preferably DMSO, DMF, dimethyl acetamide, NMP, or NEP.
  • NMP N-butyl
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide; alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, potassium oxide and calcium oxide; alkali metal and alkaline earth metal phosphates such as lithium phosphate, sodium phosphate, potassium phosphate and calcium phosphate; alkali metal amides such as lithium amide, sodium amide and potassium amide; alkali metal and alkaline earth metal hydrides lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, caesium carbonate; moreover organic bases, for example tertiary amines such as trimethyl-amine (TMA), triethylamine (TEA), tributylamine (TBA), diisopropylethylamine
  • the bases are generally employed in equimolar amounts, in excess or, if appropriate, as solvent.
  • the amount of base is typically 1.1 to 5.0 molar equivalents relative to 1 mole of compounds II.
  • the starting materials are generally reacted with one another in equimolar amounts. In terms of yields, it may be advantageous to employ an excess of compounds III, based on 1.1 to 2.5 equivalents, preferred 1 .1 to 1.5 equivalents of compounds II.
  • the compounds II are known from the literature or are commercially available or they can be prepared for example in analogy to methods described in: Heterocycles (2009) 78(7), 1627- 1665; New J. Chem. (1994) 18(6), 701 -8; WO 2005/095357; Science of Synthesis (2004) 16, 379-572; WO 2008/156726; WO 2006/072831 ; Organic Reactions (Hoboken, NJ, United States) (2000), 56; or Targets in Heterocyclic Systems (2008) 12, 59-84.
  • phenethyl amine compounds III are known from the literature or are commercially available or they can be prepared for example in analogy to methods described in:
  • Compound AD-1 is reacted with a heterocycle Het-LG, in which LG is a leaving group such as, e.g. F or CI, in the presence of a base and/or a catalyst to provide compound Het-AD.
  • LG is a leaving group such as, e.g. F or CI
  • compound AD-2 in which LG is a leaving group in para-position such as, e.g. F or CI, is reacted with a hydroxyl-heterocycle HO-Het in the presence of a base and/or a catalyst to yield compound Het-AD according to procedures described in WO 201 1/032277;
  • R 2 halogen, CN, CrC 4 -alkoxy
  • a carbonyl compound AD-1 can be transformed into its cyano hydrine
  • the nitrile in AD-3 can be reduced and the hydroxyl group be removed in one step to furnish compounds III, wherein R 2 , R 3 and R 4 are hydrogen (see e.g.
  • Phenethylamine compounds III, in which X is -CR 3 H- can also be prepared by reductive amination of ketone compounds AD-4 as described in Scheme 4.
  • This conversion can be achieved using ammonia and a reducing agent or a metal organic compound or a cyanide source (see e.g. J. Am. Chem. Soc. (201 1 ), 133(33), 12914-12917; Acta Pharmaceutica Suecica (1976), 13(1 ), 65-74; J. Med. Chem. (1976), 19(6), 763-6; or J. Am. Chem. Soc. (1952), 74, 461 1 -15).
  • Compounds III, wherein X is -CR 3 H-, can also be prepared by transformation of AD-1 to a nitro alkene AD-6 by first reacting it with nitro alkyl compounds AD-5 preferably in the presence of a base as described in Scheme 5 (see e.g. J. Org. Chem (2002), 67(14), 4875-4881 ; Eur. J. Med. Chem. (201 1 ), 46(9), 3986-3995; or J. Am. Chem. Soc. (1985), 107(12), 3601 -6):
  • Consecutive reduction e.g. with UAIH4 or hydrogen together with a suitable catalyst, leads to compounds III (Org. Biomol. Chem. (201 1 ), 9(23), 8171 -8177; J. Am. Chem. Soc. (201 1 ), 133(31 ), 12197-12219; or Eur. J. Med. Chem. (2010), 45(1 ), 1 1 -18).
  • nitro alkenes AD-6 can be reacted with an alkoxide to give the
  • nitro alkenes can be reacted with metal cyanides to give the corresponding cyano compounds (Synlett (2008), (12), 1857-1861 , J. Org. Chem. (1985), 50(20), 3878-81 ).
  • the terminal nitro group can be reduced selectively in the presence of the nitrile to yield compounds III, wherein R 2 is Ci-C4-alkoxy or CN, respectively.
  • Substituted benzyl nitrile or phenyl acetaldehyde compounds AD-7 can be alkylated
  • substituted benzyl nitriles AD-9 which are available from benzyl halides AD-8, can be used as intermediates for the preparation of compounds I I I , wherein R 2 , R 3 and R 4 are hydrogen, according to scheme 7 by way of reduction with an appropriate reducing agent (e.g. LiAIH 4 , PhSiHs or H 2 and a catalyst) as shown in Scheme 7 (Tetrahedron (201 1 ), 67(42), 8183- 8186; WO 201 1 /088181 ; Eur. J. Inorg. Chem. (201 1 ), 201 1 (22), 3381 -3386; or WO
  • an appropriate reducing agent e.g. LiAIH 4 , PhSiHs or H 2 and a catalyst
  • compounds AD-9 can be used to obtain compounds I I I , wherein at least one group R 3 or R 4 are not hydrogen. It is well known that benzyl nitriles such as AD-9 can undergo a selective addition of alkyl metals such as, for example, Grignard reagents R 3 MgHal, in which Hal stands for chlorine, bromine or iodine, either furnishing compounds II I, wherein R 3 is not hydrogen and R 4 is hydrogen, by reduction of an intermediate imine AD-10 with an appropriate reducing agent such as NaBH 4 , (Bioorg. Med. Chem. Lett.
  • alkyl metals such as, for example, Grignard reagents R 3 MgHal, in which Hal stands for chlorine, bromine or iodine
  • Compounds I and intermediates, wherein R is hydrogen, can be converted by conventional processes such as alkylation.
  • suitable alkylating agents include alkyl halides, such as alkyl chloride, alkyl bromide or alkyl iodide, examples being methyl chloride, methyl bromide or methyl iodide, or dialkyl sulfates such as dimethyl sulfate or diethyl sulfate.
  • the reaction with the alkylating agent is carried out advantageously in the presence of a solvent.
  • Solvents used for these reactions are - depending on temperature range - aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, cyclohexane, toluene, xylene, chlorinated aliphatic and aromatic hydrocarbons such as DCM, chlorobenzene, open-chain dialkyl ethers such as diethyl ether, di- n-propyl ether, MTBE, cyclic ethers such as THF, 1 ,4-dioxane, glycol ethers such as dimethyl glycol ether, and also DMSO, DMF, dimethyl acetamide, NMP, NEP and acetic acid ethyl ester, preferably DMF, DMSO, NMP or NEP, or mixtures of these solvents.
  • aliphatic, cycloaliphatic or aromatic hydrocarbons such as hexane, cyclohexane, toluene, xylene,
  • the N-oxides may be prepared from the compounds I according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroperbenzoic acid (cf. WO 03/64572 or J. Med. Chem. 1995, 38(1 1 ), 1892-1903,); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 1981 , 18 (7), 1305-1308) or oxone (cf. J. Am. Chem. Soc. 2001 , 123 (25), 5962-5973).
  • the oxidation may lead to pure mono-N- oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C4-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 4 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 - methylpropyl, 2-methylpropyl, and 1 ,1 -dimethylethyl.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms.
  • Ci-C4-haloalkyl refers to a straight-chained or branched alkyl group having 1 to 4 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-C4-hydroxyalkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms (as defined above), wherein one hydrogen atom in these groups may be replaced by one hydroxy group, for example hydroxym ethyl, 2-hydroxyethyl, 3-hydroxy-n-propyl, or 4-hydroxy-n-butyl.
  • Ci-C4-alkoxy refers to a straight-chain or branched alkyl group having 1 to 4 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 -methyhpropoxy, 2- methylpropoxy or 1 ,1 -dimethylethoxy.
  • Ci-C6-alkoxy refers to a straight- chain or branched alkyl group having 1 to 6 carbon atoms.
  • Ci-C4-haloalkoxy refers to a Ci-C4-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, OCHC , 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, OC2F5, 2-fluoropropoxy, 3- fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3- dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3- trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH 2 F)-2-fluoro
  • 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.
  • 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-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-C6-alkoxy group (as defined above).
  • Ci-C4-alkoxy-Ci-C4-alkoxy refers to an alkoxy radical having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of this alkoxy radical is replaced by a
  • Ci-C4-alkoxy group (as defined above).
  • Ci-C6-alkoxy-Ci-C4-alkoxy refers to alkoxy having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).
  • Ci-C4-haloalkoxy-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-haloalkoxy group (as defined above).
  • Ci-C6-haloalkoxy-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-C6-alkoxy group (as defined above).
  • Ci-C4-alkylthio refers to straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as defined above) bonded via a sulfur atom, at any position in the alkyl group, for example methylthio, ethylthio, propylthio, isopropylthio, and n butylthio.
  • 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.
  • Ci-C4-haloalkylthio and “Ci-C6-haloalkylthio” as used herein refer to straight-chain or branched haloalkyi groups having 1 to 4 or 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the haloalkyi group.
  • Ci-C4-alkylsulfonyl and “Ci-C6-alkylsulfonyl”, respectively, refer to straight-chain or branched alkyl groups having 1 to 4 and 1 to 6 carbon atoms (as defined above),
  • Ci-C4-alkylamino refers to an amino radical carrying one Ci-C4-alkyl group (as defined above) as substituent, for example methylamino, ethylamino, propylamino, 1 - methylethylamino, butylamino, 1 -methylpropylamino, 2-methylpropylamino, 1 ,1 -di- methylethylamino and the like.
  • Ci-C6-alkylamino refers to an amino radical carrying one Ci-C6-alkyl group (as defined above) as substituent.
  • di(Ci-C4-alkyl)amino refers to an amino radical carrying two identical or different Ci-C4-alkyl groups (as defined above) as substituents, for example dimethylamino,
  • di(Ci-C6-alkyl)amino refers to an amino radical carrying two identical or different Ci- C6-alkyl groups (as defined above) as substituents.
  • (Ci-C4-alkoxy)carbonyl refers to a Ci-C4-alkoxy radical (as defined above) which is attached via a carbonyl group.
  • di(Ci-C4-alkyl)aminocarbonyl refers to a di(Ci-C4)alkylamino radical as defined above which is attached via a carbonyl group.
  • phenoxy and refers to a phenyl radical which is attached via an oxygen atom.
  • phenoxy-Ci-C4-alkyl and refers to a phenoxy radical which is attached via a Ci-C4-alkyl group (as defined above).
  • C2-C4-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 4 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-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
  • C2-C4-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 4 carbon atoms and containing at least one triple bond, such as ethynyl, 1 - propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl.
  • C2-C6-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and at least one triple bond.
  • 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.
  • C3-C8-cycloalkyl-Ci-C4-alkyl refers to an alkyl radical having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Cs-Cs- cycloalkyl group (as defined above).
  • Cs-Cs-cycloalkyloxy refers to a cycloalkyl radical having 3 to 8 carbon atoms (as defined above), which is bonded via an oxygen.
  • saturated or partially unsaturated 3-, 4- 5-, 6- or 7-membered carbocycle is to be understood as meaning both saturated or partially unsaturated carbocycles having 3, 4, 5, 6 or 7 ring members.
  • Examples include cyclopropyl, cyclopentyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptenyl, cycloheptadienyl, and the like.
  • saturated or partially unsaturated 3-, 4-, 5-, 6-, or 7-membered heterocycle, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, e.g.:
  • - 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; or
  • - 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- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,
  • a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-,
  • heteroaryl wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S
  • ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S
  • a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-
  • 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.
  • two radicals R c that are bound to adjacent ring member atoms form together with said ring member atoms a fused cycle refers to a condensed bicyclic ring system, wherein 5- or 6-membered heteroaryl carries a fused-on 5-, 6- or 7-membered carbocyclic or heterocyclic ring it being possible that these rings are saturated or partially saturated or aromatic.
  • CH3 shall also be understood as Me
  • CH2CH3 shall also be understood as Et
  • OCH3 shall also be understood as OMe
  • OCH2OCH3 shall also be understood as OMeOMe
  • CH2OCH3 shall also be understood as MeOMe
  • COOCH 3 shall also be understood as COOMe
  • COOC2H5 shall also be understood as COOEt.
  • fungicidal activity of the compounds I preference is given to those compounds I and where applicable also to compounds of all sub-formulae provided herein, for example formulae 1.1 , 1.2, 1.3, I .A, I.B, and I.A1 to I.E2 and to the intermediates such as compounds II and III, wherein the substituents and variables (e.g.
  • R a2 , R a5 , R a6 , R, X, R 1 , R 2 , R 3 , R 4 , R A , R B , Het, n, R a , R b , R c , R d , R e , R', R" and R') have independently of each other or more preferably in combination including the combination the following meanings including also each combination of meanings for any subset of substituents and variables:
  • R b is preferably selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and Ci-C4-alkoxy-Ci-C4-alkyl; more preferably R b is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl or Ci-C4-alkoxy ; most preferably R b is halogen, CN, CH3, CF3 or OCH3. According to a further embodiment R b is F or CI. According to a further embodiment R b is CH3 or OCH3. According to a further embodiment, R b is CN or CF3. According to a further embodiment R b is F or OCH3.
  • R b is F or OCH3 in ortho-position relative to the CR 1 R 2 - moiety. According to a further embodiment R b is F or OCH3 in meta-position relative to the CR 1 R 2 -moiety.
  • n is 1 , 2, 3 or 4 and R b is selected from the group of halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and C1-C4- alkoxy-Ci-C4-alkyl.
  • n is preferably 1 .
  • R b is preferably in ortho-position relative to the CR 1 R 2 -moiety.
  • n is preferably 1 .
  • R b is preferably in meta-position relative to the CR 1 R 2 -moiety.
  • n is preferably 2. According to a further embodiment, n is preferably 3.
  • R b on the phenyl ring is defined in Table I relative to the CR 1 R 2 -moiety bound to the phenyl ring as being in ortho (o-) or meta (m-) position.
  • R a2 is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C2-C4-alkenyl, C2-C4-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy or (Ci-C4-alkoxy)- carbonyl; preferably halogen, CN, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy or (Ci-C2-alkoxy)carbonyl; even more preferably F, CI, CH3, CH2CH3, CF 3 , CHFCHs, CN, OCH 3 , O
  • R a2 is selected from CN, CH3, CF3, OCH3, COOCH3, OCH2CH3 and CH2OCH3, more preferably from CN and CH 3 .
  • R a2 is F, CI, CH 3 , OCH 3 , COOCH3 or COOC2H5. According to a further embodiment, R a2 is F or CI. According to a further embodiment, R a2 is CH3 or OCH3. According to a further embodiment, R a2 is COOCH3 or COOC2H5.
  • R A , R B in radicals R a2 , R a5 and R a6 independently of one another preferably are hydrogen or Ci-C4-alkyl.
  • R' in radicals R a2 , R a5 and R a6 which may the same or different, are hydrogen, NH2, Ci-C4-alkyl or Ci-C4-alkoxy.
  • R" in radicals R a2 , R a5 and R a6 are hydrogen, Ci-C4-alkyl.
  • R'" in radicals R a2 , R a5 and R a6 are hydrogen or Ci-C4-alkyl.
  • R a5 and R a6 independently of each other are halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
  • R a5 or R a6 can in addition be hydrogen.
  • R a5 is F, CI, CH 3 , OCH 3 , COOCH3 or COOC2H5. According to a further embodiment, R a5 is F or CI. According to a further embodiment, R a5 is CH3 or OCH 3 . According to a further embodiment, R a5 is COOCH3 or COOC2H5.
  • R a6 is F, CI, CH 3 , OCH 3 , COOCH3 or COOC2H5. According to a further embodiment, R a6 is F or CI. According to a further embodiment, R a6 is CH3 or OCH3. According to a further embodiment, R a6 is COOCH3 or COOC2H5.
  • R a5 and R a6 independently of each other are halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alk- oxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy or (Ci-C4-alkoxy)carbonyl, and it being possible that one of both, R a5 or R a6 , can in addition be hydrogen.
  • R a2 , R a5 and R a6 independently of each other are in each case one of the following groups 11-1 to 11-13 in Table II, groups III-1 to 111-13 in Table III and groups IV-1 to IV-13 in Table IV, respectively: Table II:
  • R A , R B in radical R independently of one another preferably are hydrogen or Ci-C4-alkyl.
  • R' in radical R is hydrogen, OH, NH2, Ci-C4-alkyl or Ci-C4-alkoxy.
  • Another preferred embodiment relates to compounds I wherein R is CH3.
  • X is preferably -CR 3 R 4 -, -CHCH3-, -CH(CH 2 CHs)-; more preferably X is -CR 3 R 4 -.
  • R 3 and R 4 independently of each other are preferably hydrogen, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci- C4-haloalkoxy or Cs-Cs-cycloalkyl, more preferably hydrogen, halogen or Ci-C4-alkyl.
  • R' in radicals R 3 and/or R 4 is hydrogen, OH, NH2, Ci-C4-alkyl or Ci-C4-alkoxy.
  • X is selected from -CH2-, -CHCH3-, and -CH(CH2CHs)-, in particular X is -CH2- which
  • X is -C(CH3)H-, which compounds are of formula I .B:
  • the moiety O-Het is bound in para-position to the phenylring, which com
  • the moiety O-Het is bound in meta-position to the phenylring. According to a further embodiment, the moiety O-Het is bound in ortho position to the phenylring.
  • the moiety O-Het is bound in para-position to the phenylring and the substituents R, R 1 and R 2 are hydrogen, which compounds are of formula 1.2:
  • the moiety O-Het is bound in para-position to the phenylring, R is CH3 and the substituents R 1 and R 2 are hydrogen, which compounds are of formula 1.3:
  • X is -CH2-, R is hydrogen, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula
  • X is -CH2-, R is CH3, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula I.A2:
  • X is -CH(CH3)-
  • R is hydrogen
  • the moiety CD- I-let is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula
  • X is -CH(CH3)-, R is CH3, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula I.B2:
  • X is -C(CH3)2-, n is 0, R is hydrogen, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula I.C1 :
  • X is -C(CHs)2-, R is CH3, the moiety O-Het is bound in Para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula I.C2:
  • X is -CH(CH2CH3)-, R is hydrogen, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula I.D1 :
  • X is -CH(CH2CH3)-, R is CH3, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formul
  • X is -CH(CN)-
  • R is hydrogen
  • the moiety O-Het is bound in para-position to the phenylring
  • R 1 and R 2 are both hydrogen, which compounds are of formula
  • X is -CH(CN)-, R is CH3, the moiety O-Het is bound in para-position to the phenylring and R 1 and R 2 are both hydrogen, which compounds are of formula
  • R 1 and R 2 independently of each other are preferably hydrogen, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy or Cs-Cs-cycloalkyl.
  • R 1 and R 2 independently of each other are preferably hydrogen, CN, F, CH 3 , CH2CH3 or OCH 3 , more preferably R 1 and R 2 independently of each other are hydrogen or CH3, even more preferably, R 1 and R 2 are both hydrogen.
  • R A , R B in radicals R 1 , R 2 , R 3 , R 4 , R b and/or R c , independently of one another preferably are hydrogen or Ci-C4-alkyl.
  • R' in radicals R 1 , R 2 , R 3 , R 4 and/or R c which may the same or different, are hydrogen, Nhb, Ci-C4-alkyl or Ci-C4-alkoxy.
  • R" in radicals R 1 , R 2 , R 3 , R 4 , R b and/or R c are hydrogen, Ci-C4-alkyl.
  • R'" in radicals R 1 , R 2 , R 3 , R 4 , R b and/or R c are hydrogen or Ci-C4-alkyl.
  • R b is preferably selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, (Ci-C4-alkoxy)carbonyl; more preferably R b is halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or (Ci-C4-alkoxy)carbonyl; most preferably R b is halogen, CN, CH 3 , CF 3 or OCH 3 .
  • n is 1 , 2, 3 or 4 and R b is selected from the group of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-halo- alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl and (Ci-C4-alkoxy)carbonyl.
  • n is preferably 0. According to a further embodiment, n is preferably 1 According to a further embodiment, n is preferably 2. According to a further embodiment, n is preferably 3.
  • One embodiment of the invention relates to compounds I, in which Het is a 6-mem- bered heteroaryl, wherein the ring member atoms of the heteroaryl include besides carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherin the 6-membered heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 identical or different groups R c .
  • Het is a 6-membered heteroaryl
  • Het carries at least one nitrogen as ring member atom.
  • Het is a pyrimidinyl radical that is selected from pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl and pyrimidin-6-yl, and wherein the aformentioned pyrimidinyl radicals are unsubstituted or carry 1 , 2 or 3 identical or different substituents R c .
  • Het is a 5-membered heteroaryl
  • Het carries two heteroatoms as ring member atoms.
  • Het is a thiazolyl radical that is selected from thiazol-2-yl, thiazol-4-yl and thiazol-5-yl, and wherein the aforementioned thiazolyl radicals are unsubstituted or carry 1 or 2 identical or different substituents R c .
  • Preferred embodiments of the invention relate to compounds I, in which the group Het is one of the following radicals H-1 to H-38:
  • One embodiment of the invention relates to compounds I, wherein Het carries 1 , 2 or 3 radicals R c . Another embodiment relates to compounds I, wherein Het carries 1 or 2 radicals R c . A further embodiment relates to compounds I, wherein Het carries one radical R c . A further embodiment relates to compounds I, wherein Het carries two radicals R c . A further embodiment relates to compounds I, wherein Het is
  • two radicals R c that are bound to adjacent ring member atoms of the Het group do not form together with said ring member atoms any fused cycle.
  • R c is halogen and selected from fluorine, chlorine, bromine and iodine and selected from fluorine and chlorine and in particular, R c is chlorine.
  • R c is CN
  • R c is Ci-C4-alkyl and selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, 1 -methyl-propyl, 2-methyl-propyl and 1 ,1 -dimethylethyl, and selected from methyl, ethyl, n-propyl and i-propyl, and in particular, R c is methyl.
  • R c is Ci-C4-haloalkyl and selected from Ci-haloalkyl, C2-haloalkyl, C3-haloalkyl and C4-haloalkyl. More preferably, R c is Ci-haloalkyl and selected from fluormethyl, difluormethyl, trifluormethyl, chlormethyl, dichlormethyl and trichlormethyl, and in particular, R c is trifluormethyl.
  • R c is Ci-C4-alkoxy and selected from methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, 1 -methyl-propyloxy, 2-methyl-propyloxy and 1 ,1 -dimethylethyloxy and in particular from methoxy and ethoxy.
  • R c is Ci-C4-haloalkoxy and specifically halomethoxy, such as difluormethoxy, trifluormethoxy, dichlormethoxy and trichlormethoxy, and
  • haloethoxy such as 2,2-difluorethoxy, 2,2,2-trifluorethoxy, 2,2-dichlorethoxy and 2,2,2- trichlorethoxy, and halo-n-propoxy, halo-i-propoxy, halo-n-butoxy, halo-1 -methyl- propoxy, halo-2-methyl-propoxy or halo-1 ,1 -dimethylethoxy.
  • R c is Cs-Cs-cycloalkyl, and in particular, R c is cyclopropyl. In a further embodiment, R c is phenyl.
  • R c is phenoxy
  • R c is phenoxy-Ci-C4-alkyl and selected from
  • R c relates to compounds I, wherein R c carries 1 , 2, 3 or 4 radicals R d , preferably 1 , 2 or 3 radicals R d , and more preferably 1 or 2 radicals R d .
  • R c carries one radical R d .
  • R c carries two radicals R d .
  • the group R c carries 3 radicals R d .
  • R d is halogen and selected from fluorine, chlorine, bromine and iodine and specifically from fluorine and chlorine and in particular, R c is chlorine.
  • R d is CN
  • R d is Ci-C4-alkyl and selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, 1 -methyl-propyl, 2-methyl-propyl and 1 ,1 -dimethylethyl, and preferably selected from methyl, ethyl, n-propyl and i-propyl and in particular, R d is methyl.
  • R d is Ci-C4-haloalkyl and selected from Ci-haloalkyl, C2-haloalkyl, C3-haloalkyl and C4-haloalkyl. More preferably, R c is Ci-haloalkyl and selected from fluormethyl, difluormethyl, trifluormethyl, chlormethyl, dichlormethyl and trichlormethyl, and in particular, R d is trifluormethyl.
  • R d is Ci-C4-alkoxy and selected from methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, 1 -methyl-propyloxy, 2-methyl-propyloxy and 1 ,1 -dimethylethyloxy and in particular from methoxy and ethoxy.
  • the present invention relates to compounds of the formula I.A wherein:
  • R a2 is hydrogen, halogen, Nhb, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or C1-C4- haloalkoxy;
  • R a5 , R a6 are independently selected from the goup hydrogen, halogen, CN, OH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and
  • R is hydrogen or Ci-C4-alkyl
  • R 1 , R 2 are hydrogen
  • n indicates the number of substituents R b on the phenyl ring and n is 0, 1 or 2;
  • R b is halogen, Ci-C4-alkyl or Ci-C4-alkoxy;
  • Het is a pyridinyl or pyrimidinyl wherein the pyridinyl or pyrimidinyl is unsubstituted or carries 1 or 2 groups R c :
  • R c is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or (Ci-C4-alkoxy)carbonyl; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I.A.
  • the compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • compounds I and compositions thereof are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with compounds I and compo- sitions thereof, respectively is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A.
  • Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokiniana) on cereals and e.g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g.
  • strawberries strawberries
  • vegetables e. g. lettuce, carrots, celery and cabbages
  • rape flowers, vines, forestry plants and wheat
  • Bremia lactucae downy mildew
  • Ceratocystis syn. Ophiostoma
  • Cercospora spp. rot or wilt
  • corn e.g. Gray leaf spot: C. zeae-maydis
  • sugar beets e. g. C.
  • Helminthosporium of Bipolaris spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C.
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and
  • Dematophora teleomorph: Rosellinia necatrix (root and stem rot) on soybeans
  • Diaporthe spp. e. g. D. phaseolorum (damping off) on soybeans
  • Drechs- lera syn. Helminthosporium, teleomorph: Pyrenophora
  • spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf
  • Esca dieback, apoplexy
  • vines caused by Formitiporia (syn. Phellinus) punctata, F.
  • Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa;
  • verticillioides on corn Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grain- staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G.
  • sabinae rust on pears
  • Helmintho- sporium spp. syn. Drechslera, teleomorph: Cochliobolus
  • Hemileia spp. e. g. H. vastatrix (coffee leaf rust) on coffee
  • Isariopsis clavispora syn. Cladosporium vitis
  • Macrophomina phaseolina syn. phaseoli
  • root and stem rot on soybeans and cotton
  • Microdochium syn. Fusarium
  • nivale pink snow mold
  • Microsphaera diffusa (powdery mildew) on soybeans
  • Monilinia spp. e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants
  • Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas
  • Peronospora spp. downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples
  • Polymyxa spp. e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P.
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae
  • Pseudoperonospora downy mildew
  • Pseudopezicula tracheiphila red fire disease or .rotbrenner', anamorph: Phialophora
  • Puccinia spp. rusts on various plants, e. g. P. triticina (brown or leaf rust), P.
  • striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • P. graminis seed or black rust
  • P. recondita brown or leaf rust
  • cereals such as e. g. wheat, barley or rye
  • P. kuehnii range rust
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp.
  • R. solani root and stem rot
  • S. solani silk and stem rot
  • S. solani silk and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum sheath rot) on rice
  • Sclerotinia spp e. g.
  • R. solani root and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum sheath rot
  • Sclerotinia spp Sclerotinia spp.
  • seed rot or white mold on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals;
  • rape e. g. S. sclerotiorum
  • soybeans e. g. S. rolfsii or S. sclerotiorum
  • Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (s
  • Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits;
  • Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp.
  • S. nodorum Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum
  • Synchytrium endobioticum on potatoes potato wart disease
  • Taphrina spp. e. g.
  • Tilletia spp. common bunt or stinking smut
  • cereals such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U.
  • Ustilago spp. loose smut on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • the compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • the term "protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, colling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • harmful fungi Ascomycetes such as
  • Ophiostoma spp. Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichorma spp., Alternaria spp.,
  • Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the compounds I and compositions thereof, resepectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves ("greening effect")
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • the compounds of the formula (I) can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a fungicidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emul- sions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; dimethyl sulfoxide (DMSO); ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthal
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N- methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulf- onates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphtha- lenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellu- lose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyliso- thiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Water-soluble concentrates (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying or treating compound I and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • - Inhibitors of complex III at Qo site e.g. strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin,
  • fenaminstrobin fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3- methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl- allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
  • inhibitors of complex II e. g. carboxamides: benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluz- amide, N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyr- azole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-
  • complex II e. g. carboxamides: benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, flux
  • respiration inhibitors e.g. complex I, uncouplers: diflumetorim, (5,8- difluoroquinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]- ethyl ⁇ -amine; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;
  • complex I uncouplers
  • DMI fungicides triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol,
  • triticonazole uniconazole
  • imidazoles imazalil, pefurazoate, prochloraz, triflumizol
  • pyrimidines, pyridines and piperazines fenarimol, nuarimol, pyrifenox, triforine;
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
  • hymexazole hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine;
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;
  • triazolopyrimidines 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5-a]pyrimidine
  • cell division inhibitors diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
  • blasticidin-S blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
  • MAP / histidine kinase inhibitors fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
  • - Phospholipid biosynthesis inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane;
  • lipid peroxidation dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • phospholipid biosynthesis and cell wall deposition dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1 -(1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester;
  • H) lnhibitors with Multi Site Action - inorganic active substances Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles: anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
  • guanidine dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine- tris(albesilate), dithianon;
  • glucan synthesis validamycin, polyoxin B; melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
  • fenpyrazamine flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide,
  • BOTECTOR® from bio-ferm GmbH, Germany
  • Bacillus pumilus e.g. NRRL Accession No. B-30087 in SONATA® and BALLAD® Plus from AgraQuest Inc.
  • Bacillus subtilis e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®,
  • Candida oleophila I-82 e.g. ASPIRE® from Ecogen Inc., USA
  • Candida saitoana e.g. BIOCURE® (in mixture with lysozyme) and
  • BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta
  • Chitosan e.g. ARMOUR-ZEN from BotriZen Ltd., NZ
  • Clonostachys rosea f. catenulata also named Gliocladium catenulatum (e.g. isolate J1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM,
  • Cryptococcus albidus e.g. YIELD PLUS® from Anchor Bio- Technologies, South Africa
  • Fusarium oxysporum e.g. BIOFOX® from
  • Metschnikowia fructicola e.g. SHEMER® from Agrogreen, Israel
  • Microdochium dimerum e.g. ANTIBOT® from Agrauxine, France
  • Phlebiopsis gigantea e.g.
  • ROTSOP® from Verdera, Finland
  • Pseudozyma flocculosa e.g. SPORODEX® from Plant Products Co. Ltd., Canada
  • Pythium oligandrum DV74 e.g.
  • asperellum SKT-1 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan), T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T. harzianum T-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T. harzianum TH 35 (e.g. ROOT PRO® from Mycontrol Ltd., Israel), T. harzianum T-39 (e.g. TRICHODEX® and TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. viride (e.g.
  • T. harzianum ICC012 and T. viride ICC080 e.g. REMEDIER® WP from Isagro Ricerca, Italy
  • T. polysporum and T. harzianum e.g. BINAB® from BINAB Bio-Innovation AB, Sweden
  • T. stromaticum e.g. TRICOVAB® from C.E.P.L.A.C., Brazil
  • T. virens GL-21 e.g. SOILGARD® from Agrimm Technologies Ltd, NZ
  • T. harzianum ICC012 and T. viride ICC080 e.g. REMEDIER® WP from Isagro Ricerca, Italy
  • T. polysporum and T. harzianum e.g. BINAB® from BINAB Bio-Innovation AB, Sweden
  • T. stromaticum e.g. TRICOVAB® from C.E.P.L.A.C.
  • T. viride e.g. TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co. Ltd., Indien
  • T. viride TV1 e.g. T. viride TV1 from Agribiotec srl, Italy
  • Ulocladium oudemansii HRU3 e.g. BOTRY- ZEN® from Botry-Zen Ltd, NZ
  • BOTRY- ZEN® from Botry-Zen Ltd, NZ
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3- acetic acid , maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • - (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • - phenoxy acetic acids clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, Mecoprop;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • - sulfonyl ureas amidosulfuron, azimsulfuron, bensulfuron, chlorimuron- ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron,
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron,tebuthiuron; - other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam- methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho- sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • amicarbazone amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone,benfluresate, benzofenap, bentazone, benzobicyclon,
  • bicyclopyrone bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac- pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - pyrethroids allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • chitin synthesis inhibitors benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine;
  • ecdysone antagonists benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine;
  • lipid biosynthesis inhibitors pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors:
  • nicotinic receptor agonists/antagonists compounds clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 - (2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
  • GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, 5-amino-1 -(2,6-dichloro-4-methyl-phenyl)-4-sulfinamoyl- 1 H-pyrazole-3-carbothioic acid amide;
  • - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • - mitochondrial electron transport inhibitor I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • cryomazine cryomazine
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (com- ponent 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to L), as described above, and if desired one suitable solvent or solid carrier.
  • agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (com- ponent 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to L), as described above, and if desired one suitable solvent or solid carrier.
  • combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to L), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to L).
  • compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).
  • the order of application is not essential for working of the present invention.
  • the weight ratio of component 1 and component 2 generally depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :3 to 3:1.
  • the weight ratio of component 1 and component 2 depends from the properties of the active substances used, preferably it is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1
  • the weight ratio of component 1 and component 3 preferably is in the range of from 1 :50 to 50:1 and particularly in the range of from 1 :10 to 10:1.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group A) (component 2) and particularly selected from azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl,
  • orysastrobin picoxystrobin, pyraclostrobin, trifloxystrobin; famoxadone, fenamidone; bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad, sedaxane; ametoctradin, cyazofamid, fluazinam, fentin salts, such as fentin acetate.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group B) (component 2) and particularly selected from cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, fenarimol, triforine; dodemorph, fenpropimorph, tridemorph, fenpropidin, spiroxamine; fenhexamid.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group C) (component 2) and particularly selected from metalaxyl, (metalaxyl-M) mefenoxam, ofurace.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group D) (component 2) and particularly selected from benomyl, carbendazim, thiophanate-methyl, ethaboxam, fluopicolide, zoxamide, metrafenone, pyriofenone.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group E) (component 2) and particularly selected from cyprodinil, mepanipyrim, pyrimethanil.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group F) (component 2) and particularly selected from iprodione, fludioxonil, vinclozolin, quinoxyfen.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group G) (component 2) and particularly selected from dimethomorph, flumorph, iprovalicarb, benthiavalicarb, mandipropamid, propamocarb.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group H) (component 2) and particularly selected from copper acetate, copper hydroxide, copper oxychloride, copper sulfate, sulfur, mancozeb, metiram, propineb, thiram, captafol, folpet, chlorothalonil, dichlofluanid, dithianon.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group I) (component 2) and particularly selected from carpropamid and fenoxanil.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group J) (component 2) and particularly selected from acibenzolar-S-methyl, probenazole, tiadinil, fosetyl, fosetyl-aluminium, H3PO3 and salts thereof.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group K) (component 2) and particularly selected from cymoxanil, proquinazid and N-methyl-2- ⁇ 1 -[(5-methyl-3-trifluoromethyl- 1 H-pyrazol-1 -yl)-acetyl]-piperidin-4-yl ⁇ -N-[(1 R)-1 ,2,3,4-tetrahydronaphthalen-1 -yl]- 4-thiazolecarboxamide.
  • mixtures comprising a compound I (component 1 ) and at least one active substance selected from group L) (component 2) and particularly selected from Bacillus subtilis strain NRRL No. B-21661 , Bacillus pumilus strain NRRL No. B-30087 and Ulocladium oudemansii.
  • the present invention furthermore relates to compositions comprising one compound I (component 1 ) and one further active substance (component 2), which further active substance is selected from the column "Component 2" of the lines D-1 to D-370 of Table D.
  • a further embodiment relates to the compositions D-1 to D-370 listed in Table D, where a row of Table D corresponds in each case to a fungicidal composition comprising one of the in the present specification individualized compounds of formula I (component 1 ) and the respective further active substance from groups A) to O) (component 2) stated in the row in question.
  • the compositions described comprise the active substances in synergistically effective amounts.
  • Table D Composition comprising one indiviualized compound I and one further active substance from groups A) to O) Mixture Component 1 Component 2
  • component 2 The active substances referred to as component 2, their preparation and their activity against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J.
  • the mixtures of active substances can be prepared as compositions comprising besides the active ingridients at least one inert ingredient by usual means, e. g. by the means given for the compositions of compounds I.
  • the mixtures of active substances according to the present invention are suitable as fungicides, as are the compounds of formula I. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and
  • hydrochloride was prepared from 2-fluoro-4-methoxybenzaldehyde as described in US 201 10054173 A1.
  • 2-(3-Methoxy-4-hydroxyphenyl)ethylamine-fert-butylcarbamate was prepared according to literature precedents in Bioorganic & Medicinal Chemistry (201 1 ), 19(2), 783-788 and in European Journal of Medicinal Chemistry (2008), 43(6), 1 160-1 170.
  • 4,6-Dichloro-5-pyrimidinecarboxylic acid methyl ester was prepared from 4,6-dihydroxypyrimidine as described in Journal of Medicinal Chemistry (2010), 53(13), 5012-5024.
  • 4-Chloro-6-ethyl-5-pyrimidinecarboxylic acid ethyl ester was synthesized according to US 543991 1 A. 4-Chloro-6-ethyl-2-methyl-5-pyrimidinecarboxylic acid ethyl ester and 4-chloro-6-methyl-5-pyrimidinecarboxylic acid methyl ester were prepared as described in EP 60601 1 A1 .
  • Example 3 Preparation of 6-chloro-N-[2-[2-fluoro-4-[[4-(trifluoromethyl)-2-pyridyl] oxy]phenyl]ethyl]-5-methoxy-pyrimidin-4-amine (V-14) To a solution of 2-[2-fluoro-4-[[4-(trifluoromethyl)-2-pyridyl]oxy]phenyl]ethanamine hydrochloride (344 mg, 0.9 mmol) in NMP (5 ml.) was added diisopropylethylamine (0.36 mL, 2.1 mmol).
  • Table V Compounds V-1 to V-86 of formula 1.A as defined herein, whereas the group O-Het in each case is attached in ortho-position of the phenyl ring relative to the CR 1 R 2 -moiety and R 1 and R 2 are in each case both hydrogen.
  • m.p. melting point (°C).
  • HPLC HPLC-column Kinetex XB C18 1 ,7 ⁇ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (gradient from 5:95 to 100 : 0 in 1 .5 min at 60°C, flow gradient from 0.8 to
  • the spray solutions were prepared in several steps: The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting
  • agent/emulsifier Wettol which is based on ethoxylated alkylphenoles, in a relation (volume) solvent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml.
  • This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.
  • Use example 3 Preventative fungicidal control of Botrytis cinerea on leaves of green pepper
  • Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with a aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber and kept for 5 days at 22 to 24°C and a relative humidity close to 100 %.
  • Use example 1 Preventative control of brown rust on wheat caused by Puccinia recondita
  • the first two developed leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below.
  • the next day the plants were inoculated with spores of Puccinia recondita.
  • the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99 % and 20 to 24°C for 24 h.
  • the trial plants were cultivated for 6 days in a greenhouse chamber at 20 to 24°C and a relative humidity between 65 and 70%.
  • Leaves of pot-grown soybean seedlings were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture as described below.
  • the plants were allowed to air-dry.
  • the trial plants were cultivated for 1 day in a greenhouse chamber at 23 to 27 ° C and a relative humidity between 60 and 80%.
  • the plants were inoculated with spores of Phakopsora pachyrhizi.
  • the plants were transferred to a humid chamber with a relative humi- dity of about 95% and 20 - 24°C for 24 h.
  • the trial plants were cultivated for fourteen days in a greenhouse chamber at 23 to 27°C and a relative humidity between 60 and 80%.
  • Use example 3 Control of late blight on tomatoes caused by Phytophthora infestans Young seedlings of tomato plants were grown in pots. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day, the treated plants were inoculated with an aqueous suspension of sporangia of Phytophthora infestans. After inoculation, the trial plants were immediately transferred to a humid chamber and kept for 6 days at 18 to 20°C and a relative humidity close to 100%.
  • the plants which had been treated with 250 ppm of the active compound V-2, V-3, V-6, V-7, V-9, V-10, V-12, V-13, V-14, V-16, V-17, V-18, V-19, V-23, V-26, V-28, V-31 , V-32, V-33, V-42, V-45, V-47, V-49, V-50, V-55, V-56, V-57, V-67, V-69, V-71 , V-72, V-77, V-82, V-83, V-85 or V-86 showed a diseased leaf area of at most 20%, whereas the untreated plants showed 79% diseased leaf area.
  • Use example 4 Preventative control of leaf blotch on wheat caused by Septoria tritici Leaves of pot-grown wheat seedling were sprayed to run-off with an aqueous suspension of the active compound or their mixture, prepared as described. The plants were allowed to air-dry. At the following day the plants were inoculated with an aqueous spore suspension of Septoria tritici. Then the trial plants were immediately transferred to a humid chamber at 18 to 22°C and a relative humidity close to 100%. After 4 days the plants were transferred to a chamber with 18 to 22°C and a relative humidity close to 70% and kept there for 4 weeks.

Abstract

La présente invention concerne des composés de pyrimidine fongicides I, leur utilisation et des procédés permettant de lutter contre des champignons phytopathogènes. La présente invention concerne également des graines traitées par au moins un desdits composés. L'invention concerne en outre des procédés pour préparer les composés de formule (I).
PCT/EP2013/051725 2012-02-03 2013-01-30 Composés de pyrimidine fongicides WO2013113720A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP12153768.2 2012-02-03
EP12153768 2012-02-03
EP12154153.6 2012-02-07
EP12154153 2012-02-07

Publications (1)

Publication Number Publication Date
WO2013113720A1 true WO2013113720A1 (fr) 2013-08-08

Family

ID=47683707

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/051725 WO2013113720A1 (fr) 2012-02-03 2013-01-30 Composés de pyrimidine fongicides

Country Status (2)

Country Link
AR (1) AR089890A1 (fr)
WO (1) WO2013113720A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014063642A1 (fr) * 2012-10-25 2014-05-01 中国中化股份有限公司 Composé à pyrimidines substituées et ses applications
CN105753791A (zh) * 2014-12-19 2016-07-13 沈阳中化农药化工研发有限公司 取代嘧啶类化合物及其用途

Citations (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
GB2059955A (en) 1979-09-13 1981-04-29 Merck & Co Inc Process for preparing methylvanillyl ketone
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0264217A2 (fr) 1986-10-08 1988-04-20 Ube Industries, Ltd. Dérivés d'aralkylaminopyrimidine, procédé pour leur préparation et insecticides, acaricides et fongicides contenant ces composés comme ingredients actifs
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
EP0606011A1 (fr) 1992-12-28 1994-07-13 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivés d'aminopyriden, procédé pour leur préparation et leur utilisation
WO1995018795A1 (fr) 1994-01-07 1995-07-13 Dowelanco N-(4-pyrimidinyle)amide en tant que pesticides
EP0665225A1 (fr) 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phénylaminopyrimidines, procédé pour leur préparation et pesticides pour l'agriculture et l'horticulture les contenant
DE19518073A1 (de) 1995-05-17 1996-11-21 Hoechst Ag Substituierte Benzyloxycarbonylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
WO1997028133A1 (fr) 1996-02-01 1997-08-07 Bayer Aktiengesellschaft 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites
WO1998003272A1 (fr) 1996-07-19 1998-01-29 Ube Industries, Ltd. Procedes pour la preparation de composes de 4-amino-5-chloro-6-(1-fluoroethyle)pyrimidine
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
WO2004026305A1 (fr) 2002-09-19 2004-04-01 Eli Lilly And Company Diaryle ethers utilises en tant qu'antagonistes de recepteur opioides
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
WO2005000246A2 (fr) 2003-06-25 2005-01-06 Elan Pharmaceuticals, Inc. Methodes et compositions de traitement de polyarthrite rhumatoide
WO2005014534A1 (fr) 2003-08-08 2005-02-17 Transtech Pharma, Inc. Composes aryle et heteroaryle, compositions, et methodes d'utilisation
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005095357A2 (fr) 2004-03-30 2005-10-13 Taisho Pharmaceutical Co., Ltd. Derives de pyrimidine et procedes de traitement lies a l'utilisation de ceux-ci
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
AU2006201959A1 (en) 1997-12-22 2006-06-01 Bayer Healthcare Llc Inhibition of Raf Kinase using Substituted Heterocyclic Ureas
WO2006072831A1 (fr) 2005-01-10 2006-07-13 Pfizer Inc. Pyrrolopyrazoles, puissants inhibiteurs de kinases
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2006098961A2 (fr) 2005-03-09 2006-09-21 Schering Corporation Composes servant a inhiber l'activite de la kinesine ksp
WO2007006714A1 (fr) 2005-07-07 2007-01-18 Medivir Ab Inhibiteurs de cystéine protéase
WO2007020227A1 (fr) 2005-08-15 2007-02-22 Boehringer Ingelheim International Gmbh Procede de production de betamimetiques
WO2007020381A2 (fr) 2005-08-15 2007-02-22 Syngenta Participations Ag Procede
WO2007046809A1 (fr) 2005-10-21 2007-04-26 Dow Agrosciences Llc Composes de thieno-pyrimidine a activite fongicide
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
WO2007096647A2 (fr) 2006-02-27 2007-08-30 Sterix Limited Composé
WO2007099326A1 (fr) 2006-03-02 2007-09-07 Astrazeneca Ab Dérivés de la quinoline
WO2008034142A2 (fr) 2006-09-15 2008-03-20 Reviva Pharmaceuticals, Inc. Synthèse, procédés d'utilisation et compositions de cycloalkylméthylamines
WO2008039882A1 (fr) 2006-09-30 2008-04-03 Sanofi-Aventis U.S. Llc Combinaison de niacine et d'un antagoniste du récepteur de prostaglandine d2
WO2008046598A1 (fr) 2006-10-20 2008-04-24 Laboratorios Almirall, S.A. DÉRIVÉS DE 4-(2-AMINO-1-HYDROXYÉTHYL)PHÉNOL EN TANT QU'AGONISTES DU RÉCEPTEUR ADRÉNERGIQUE β2
WO2008065393A1 (fr) 2006-11-29 2008-06-05 Astrazeneca Ab Dérivés d'hydantoine utilisés comme inhibiteurs de mmp
US20080171761A1 (en) 2007-01-12 2008-07-17 Tomoharu Iino Substituted spirochromanone derivatives
WO2008124757A1 (fr) 2007-04-10 2008-10-16 Bristol-Myers Squibb Company Composés de thiazolyle en tant qu'inhibiteurs de kinase
WO2008156726A1 (fr) 2007-06-20 2008-12-24 Merck & Co., Inc. Inhibiteurs des janus kinases
WO2009156100A1 (fr) 2008-06-24 2009-12-30 Sanofi-Aventis Isoquinolines et isoquinolinones substituées utilisées comme inhibiteurs de rho-kinase
WO2010025451A2 (fr) 2008-08-29 2010-03-04 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(hétéroaryloxy)-phényle) éthylamino) quinazolines et leur utilisation en tant que produits agrochimiques
US20100068197A1 (en) 2008-07-11 2010-03-18 Myriad Pharmaceuticals, Inc. Pharmaceutical compounds as inhibitors of cell proliferation and the use thereof
WO2010081692A1 (fr) 2009-01-19 2010-07-22 Almirall, S.A. Dérivés d'oxadiazole comme agonistes du récepteur s1p1
WO2010136493A1 (fr) 2009-05-28 2010-12-02 Novartis Ag Dérivés aminopropioniques substitués comme inhibiteurs de néprilysine
US20110054173A1 (en) 2009-08-31 2011-03-03 Dow Agrosciences Llc Pteridines and their use as agrochemicals
WO2011025505A1 (fr) 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
WO2011032277A1 (fr) 2009-09-18 2011-03-24 Boehringer Ingelheim International Gmbh Dérivés de quinazolinone comme inhibiteurs de polymérase virale
WO2011053835A1 (fr) 2009-10-30 2011-05-05 Aton Pharma, Inc. Synthèse stéréosélective de métyrosine
WO2011088181A1 (fr) 2010-01-13 2011-07-21 Tempero Pharmaceuticals, Inc. Composés et procédés
WO2011100285A1 (fr) 2010-02-10 2011-08-18 Lexicon Pharmaceuticals, Inc. Inhibiteurs de la tryptophane hydroxylase pour le traitement de la maladie osseuse métastatique

Patent Citations (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
GB2059955A (en) 1979-09-13 1981-04-29 Merck & Co Inc Process for preparing methylvanillyl ketone
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0264217A2 (fr) 1986-10-08 1988-04-20 Ube Industries, Ltd. Dérivés d'aralkylaminopyrimidine, procédé pour leur préparation et insecticides, acaricides et fongicides contenant ces composés comme ingredients actifs
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
EP0606011A1 (fr) 1992-12-28 1994-07-13 SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. Dérivés d'aminopyriden, procédé pour leur préparation et leur utilisation
US5439911A (en) 1992-12-28 1995-08-08 Shionogi & Co., Ltd. Aminopyrimidine derivatives and their production and use
WO1995018795A1 (fr) 1994-01-07 1995-07-13 Dowelanco N-(4-pyrimidinyle)amide en tant que pesticides
EP0665225A1 (fr) 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phénylaminopyrimidines, procédé pour leur préparation et pesticides pour l'agriculture et l'horticulture les contenant
DE19518073A1 (de) 1995-05-17 1996-11-21 Hoechst Ag Substituierte Benzyloxycarbonylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
WO1997028133A1 (fr) 1996-02-01 1997-08-07 Bayer Aktiengesellschaft 4-amino- et 4-hydrazinopyrimidines acylees et leur utilisation comme agents pour lutter contre les parasites
WO1998003272A1 (fr) 1996-07-19 1998-01-29 Ube Industries, Ltd. Procedes pour la preparation de composes de 4-amino-5-chloro-6-(1-fluoroethyle)pyrimidine
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
AU2006201959A1 (en) 1997-12-22 2006-06-01 Bayer Healthcare Llc Inhibition of Raf Kinase using Substituted Heterocyclic Ureas
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
WO2004026305A1 (fr) 2002-09-19 2004-04-01 Eli Lilly And Company Diaryle ethers utilises en tant qu'antagonistes de recepteur opioides
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
WO2005000246A2 (fr) 2003-06-25 2005-01-06 Elan Pharmaceuticals, Inc. Methodes et compositions de traitement de polyarthrite rhumatoide
WO2005014534A1 (fr) 2003-08-08 2005-02-17 Transtech Pharma, Inc. Composes aryle et heteroaryle, compositions, et methodes d'utilisation
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005095357A2 (fr) 2004-03-30 2005-10-13 Taisho Pharmaceutical Co., Ltd. Derives de pyrimidine et procedes de traitement lies a l'utilisation de ceux-ci
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
WO2006072831A1 (fr) 2005-01-10 2006-07-13 Pfizer Inc. Pyrrolopyrazoles, puissants inhibiteurs de kinases
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2006098961A2 (fr) 2005-03-09 2006-09-21 Schering Corporation Composes servant a inhiber l'activite de la kinesine ksp
WO2007006714A1 (fr) 2005-07-07 2007-01-18 Medivir Ab Inhibiteurs de cystéine protéase
WO2007020227A1 (fr) 2005-08-15 2007-02-22 Boehringer Ingelheim International Gmbh Procede de production de betamimetiques
WO2007020381A2 (fr) 2005-08-15 2007-02-22 Syngenta Participations Ag Procede
WO2007046809A1 (fr) 2005-10-21 2007-04-26 Dow Agrosciences Llc Composes de thieno-pyrimidine a activite fongicide
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
WO2007096647A2 (fr) 2006-02-27 2007-08-30 Sterix Limited Composé
WO2007099326A1 (fr) 2006-03-02 2007-09-07 Astrazeneca Ab Dérivés de la quinoline
WO2008034142A2 (fr) 2006-09-15 2008-03-20 Reviva Pharmaceuticals, Inc. Synthèse, procédés d'utilisation et compositions de cycloalkylméthylamines
WO2008039882A1 (fr) 2006-09-30 2008-04-03 Sanofi-Aventis U.S. Llc Combinaison de niacine et d'un antagoniste du récepteur de prostaglandine d2
WO2008046598A1 (fr) 2006-10-20 2008-04-24 Laboratorios Almirall, S.A. DÉRIVÉS DE 4-(2-AMINO-1-HYDROXYÉTHYL)PHÉNOL EN TANT QU'AGONISTES DU RÉCEPTEUR ADRÉNERGIQUE β2
WO2008065393A1 (fr) 2006-11-29 2008-06-05 Astrazeneca Ab Dérivés d'hydantoine utilisés comme inhibiteurs de mmp
US20080171761A1 (en) 2007-01-12 2008-07-17 Tomoharu Iino Substituted spirochromanone derivatives
WO2008124757A1 (fr) 2007-04-10 2008-10-16 Bristol-Myers Squibb Company Composés de thiazolyle en tant qu'inhibiteurs de kinase
WO2008156726A1 (fr) 2007-06-20 2008-12-24 Merck & Co., Inc. Inhibiteurs des janus kinases
WO2009156100A1 (fr) 2008-06-24 2009-12-30 Sanofi-Aventis Isoquinolines et isoquinolinones substituées utilisées comme inhibiteurs de rho-kinase
US20100068197A1 (en) 2008-07-11 2010-03-18 Myriad Pharmaceuticals, Inc. Pharmaceutical compounds as inhibitors of cell proliferation and the use thereof
WO2010025451A2 (fr) 2008-08-29 2010-03-04 Dow Agrosciences Llc 5,8-difluoro-4-(2-(4-(hétéroaryloxy)-phényle) éthylamino) quinazolines et leur utilisation en tant que produits agrochimiques
WO2010081692A1 (fr) 2009-01-19 2010-07-22 Almirall, S.A. Dérivés d'oxadiazole comme agonistes du récepteur s1p1
WO2010136493A1 (fr) 2009-05-28 2010-12-02 Novartis Ag Dérivés aminopropioniques substitués comme inhibiteurs de néprilysine
US20110054173A1 (en) 2009-08-31 2011-03-03 Dow Agrosciences Llc Pteridines and their use as agrochemicals
WO2011025505A1 (fr) 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
WO2011032277A1 (fr) 2009-09-18 2011-03-24 Boehringer Ingelheim International Gmbh Dérivés de quinazolinone comme inhibiteurs de polymérase virale
WO2011053835A1 (fr) 2009-10-30 2011-05-05 Aton Pharma, Inc. Synthèse stéréosélective de métyrosine
WO2011088181A1 (fr) 2010-01-13 2011-07-21 Tempero Pharmaceuticals, Inc. Composés et procédés
WO2011100285A1 (fr) 2010-02-10 2011-08-18 Lexicon Pharmaceuticals, Inc. Inhibiteurs de la tryptophane hydroxylase pour le traitement de la maladie osseuse métastatique

Non-Patent Citations (72)

* Cited by examiner, † Cited by third party
Title
ACTA PHARMACEUTICA SUECICA, vol. 13, no. 1, 1976, pages 65 - 74
ADV. SYNTH. CATAL., vol. 353, no. 2, 3, 2011, pages 501 - 507
ARCHIV DER PHARMAZIE, vol. 344, no. 6, 2011, pages 372 - 385
BIOORG. MED. CHEM. LETT., vol. 17, no. 4, 2007, pages 974 - 977
BIOORG. MED. CHEM. LETT., vol. 21, no. 5, 2011, pages 1434 - 1437
BIOORG. MED. CHEM. LETT., vol. 21, no. 6, 2011, pages 1741 - 1743
BIOORG. MED. CHEM., vol. 12, no. 15, 2004, pages 4055 - 4066
BIOORGANIC & MEDICINAL CHEMISTRY, vol. 19, no. 2, 2011, pages 783 - 788
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
CHEM. BIODIVERSITY, vol. 2, no. 9, 2005, pages 1217 - 1231
CHEM. PHARM. BULL., vol. 51, no. 6, 2003, pages 702 - 709
CHEMISTRY A EUR. J., vol. 17, no. 44, 2011, pages 12276 - 12279
CHIRALITY, vol. 21, no. 9, 2009, pages 836 - 842
EUR. J. INORG. CHEM., vol. 2011, no. 22, 2011, pages 3381 - 3386
EUR. J. MED. CHEM., vol. 44, no. 5, 2009, pages 2246 - 2251
EUR. J. MED. CHEM., vol. 45, no. 1, 2010, pages 11 - 18
EUR. J. MED. CHEM., vol. 46, no. 9, 2011, pages 3986 - 3995
EUR. J. ORG. CHEM., 2002, pages 3243 - 3249
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 43, no. 6, 2008, pages 1160 - 1170
HETEROCYCLES, vol. 78, no. 7, 2009, pages 1627 - 1665
J. AM CHEM. SOC., vol. 127, no. 29, 2005, pages 10186 - 10187
J. AM. CHEM. SOC., vol. 107, no. 12, 1985, pages 3601 - 6
J. AM. CHEM. SOC., vol. 121, no. 18, 1999, pages 4369 - 4378
J. AM. CHEM. SOC., vol. 123, no. 25, 2001, pages 5962 - 5973
J. AM. CHEM. SOC., vol. 133, no. 31, 2011, pages 12197 - 12219
J. AM. CHEM. SOC., vol. 133, no. 33, 2011, pages 12914 - 12917
J. AM. CHEM. SOC., vol. 55, 1933, pages 2593 - 7
J. AM. CHEM. SOC., vol. 70, 1948, pages 3738 - 40
J. AM. CHEM. SOC., vol. 74, 1952, pages 4611 - 15
J. CHEM. SOC., 1959, pages 1780 - 2
J. HETEROCYC. CHEM., vol. 18, no. 7, 1981, pages 1305 - 1308
J. MASS SPECTROMETRY, vol. 43, no. 4, 2008, pages 528 - 534
J. MED. CHEM., vol. 19, no. 6, 1976, pages 763 - 6
J. MED. CHEM., vol. 38, no. 11, 1995, pages 1892 - 1903
J. MED. CHEM., vol. 42, no. 19, 1999, pages 3965 - 3970
J. MED. CHEM., vol. 50, no. 20, 2007, pages 5003 - 5011
J. MED. CHEM., vol. 54, no. 15, 2011, pages 5335 - 5348
J. ORG. CHEM, vol. 67, no. 14, 2002, pages 4875 - 4881
J. ORG. CHEM., vol. 46, no. 4, 1981, pages 783 - 8
J. ORG. CHEM., vol. 50, no. 20, 1985, pages 3878 - 81
J. ORG. CHEM., vol. 60, no. 13, 1995, pages 4204 - 12
J. ORG. CHEM., vol. 70, no. 14, 2005, pages 5519 - 5527
J. ORG. CHEM., vol. 72, no. 22, 2007, pages 8422 - 8426
J. ORG. CHEM., vol. 73, no. 18, 2008, pages 7373 - 7375
JINGXI HUAGONG ZHONGJIANTI, vol. 40, no. 3, 2010, pages 26 - 28
JOURNAL OF MEDICINAL CHEMISTRY, vol. 53, no. 13, 2010, pages 5012 - 5024
JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 564, 1949, pages 49 - 54
JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 605, 1957, pages 200 - 11
KNOWLES: "Adjuvants and additives, Agrow Reports DS256", 2006, T&F INFORMA UK, article "chapter 5"
MCCUTCHEON'S: "Emulsifiers & Detergents, McCutcheon's Directories", vol. 1, 2008, INTERNATIONAL ED. OR NORTH AMERICAN ED
NEW J. CHEM., vol. 18, no. 6, 1994, pages 701 - 8
ORG. BIOMOL. CHEM., vol. 9, no. 23, 2011, pages 8171 - 8177
ORG. LETT., vol. 3, no. 26, 2001, pages 4315 - 4317
ORG. LETT., vol. 8, no. 20, 2006, pages 4481 - 4484
ORG. LETT., vol. 9, no. 2, 2007, pages 203 - 206
ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 15, no. 4, 2011, pages 871 - 875
ORGANIC REACTIONS, 2000, pages 56
PESTIC. SCI., vol. 44, no. 4, 1995, pages 341 - 355
SCIENCE OF SYNTHESIS, vol. 16, 2004, pages 379 - 572
SYNLETT, 2003, pages 353 - 356
SYNLETT, 2008, pages 1857 - 1861
SYNTHESIS, 1986, pages 301 - 3
TARGETS IN HETEROCYCLIC SYSTEMS, vol. 12, 2008, pages 59 - 84
TETRAHEDRON LETT., vol. 26, no. 36, 1985, pages 4299 - 300
TETRAHEDRON LETT., vol. 44, no. 12, 2003, pages 2557 - 2560
TETRAHEDRON LETT., vol. 48, no. 38, 2007, pages 6779 - 6784
TETRAHEDRON LETTERS, vol. 35, no. 31, 1994, pages 5649 - 52
TETRAHEDRON, vol. 44, no. 15, 1988, pages 4737 - 46
TETRAHEDRON, vol. 55, no. 43, 1999, pages 12493 - 12514
TETRAHEDRON, vol. 57, no. 40, 2001, pages 8573 - 8580
TETRAHEDRON, vol. 58, no. 8, 2002, pages 1513 - 1518
TETRAHEDRON, vol. 67, no. 42, 2011, pages 8183 - 8186

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014063642A1 (fr) * 2012-10-25 2014-05-01 中国中化股份有限公司 Composé à pyrimidines substituées et ses applications
CN104684900A (zh) * 2012-10-25 2015-06-03 中国中化股份有限公司 取代嘧啶类化合物及其用途
US20150257385A1 (en) * 2012-10-25 2015-09-17 Sinochem Corporation Substituted Pyrimidine Compound and Uses Thereof
US9770026B2 (en) * 2012-10-25 2017-09-26 Shenyang Sinochem Agrochemicals R&D Co., Ltd. Substituted pyrimidine compound and uses thereof
CN105753791A (zh) * 2014-12-19 2016-07-13 沈阳中化农药化工研发有限公司 取代嘧啶类化合物及其用途
CN105753791B (zh) * 2014-12-19 2019-09-13 沈阳中化农药化工研发有限公司 取代嘧啶类化合物及其用途

Also Published As

Publication number Publication date
AR089890A1 (es) 2014-09-24

Similar Documents

Publication Publication Date Title
US9072301B2 (en) Fungicidal pyrimidine compounds
AU2016299729B2 (en) Pyridine compounds useful for combating phytopathogenic fungi
EP3277680B1 (fr) Composés de quinoléine
EP2809658B1 (fr) Composés de pyrimidine fongicides
EP3359530A1 (fr) Dérivés de pyridine pour lutter contre des champignons phytopathogènes
WO2014095548A1 (fr) Composés triazoles substitués en [1,2,4] et leur utilisation comme fongicides
WO2015036058A1 (fr) Composés pyrimidines fongicides
WO2014095655A1 (fr) Composés imidazole et triazole substitués en [1,2,4]
WO2013113776A1 (fr) Composés de pyrimidine fongicides
WO2014095381A1 (fr) Composés imidazolyl et triazolyl fongicides
WO2015036059A1 (fr) Composés fongicides de pyrimidine
WO2013113781A1 (fr) Composés de pyrimidine fongicides i
WO2013113788A1 (fr) Composés de pyrimidine fongicides
WO2013113716A1 (fr) Composés de pyrimidine fongicides
WO2013113773A1 (fr) Composés fongicides de pyrimidine
WO2013113778A1 (fr) Composés de pyrimidine fongicides
WO2014095637A1 (fr) Composés imidazole et triazole substitués en [1,2,4]
WO2013135671A1 (fr) Composés de pyrimidine fongicides
WO2013113720A1 (fr) Composés de pyrimidine fongicides
WO2013135672A1 (fr) Composés de pyrimidine fongicides
WO2013113719A1 (fr) Composés de pyrimidine fongicides ii
WO2013113782A1 (fr) Composés de pyrimidine fongicides
EP2746264A1 (fr) [1,2,4]triazole substitué et composés d'imidazole
EP2746279A1 (fr) Composés triazolyles et imidazolyles fongicides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13703550

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13703550

Country of ref document: EP

Kind code of ref document: A1