WO2013113791A1 - Composés de pyrimidine fongicides - Google Patents

Composés de pyrimidine fongicides Download PDF

Info

Publication number
WO2013113791A1
WO2013113791A1 PCT/EP2013/051859 EP2013051859W WO2013113791A1 WO 2013113791 A1 WO2013113791 A1 WO 2013113791A1 EP 2013051859 W EP2013051859 W EP 2013051859W WO 2013113791 A1 WO2013113791 A1 WO 2013113791A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
individualized compound
compounds
compound
Prior art date
Application number
PCT/EP2013/051859
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 WO2013113791A1 publication Critical patent/WO2013113791A1/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

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 1995/18795 relates to N-(4-pyrimidinyl)amide pesticides and EP 665225 A1 relates to 4-phenethylamino pyrimidine derivatives useful for chemical control of noxious organisms.
  • the compounds according to the present invention differ from those described in the abovementioned publications by the specific substituent R a5 of the pyrimidine group in position 5 as defined herein and in that the phenyl ring is substituted with a heteroaryloxy group.
  • EP 264217 A2 relates to N-(4-pyrimidinyl)arylalkylamine pesticides, inter alia disclosing N- (4-pyrimidinyl)phenylethylamines.
  • EP 264217 A2 does not mention the specific combination of the specific substituent R a5 on the pyrimidine ring together with a heteroaryloxy substitution of the phenyl ring.
  • 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 is (Ci-C4-alkoxy)carbonyl
  • R a2 , R a6 independently of each other are hydrogen, halogen, CN, NO2, OH, SH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-
  • Ci-C4-haloalkylsulfonyl Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy,
  • R A , R B independently of one another are hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4- alkynyl, phenyl, benzyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkenyl or
  • R' is hydrogen, OH , N H 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylamino or di(Ci-C 4 -alkyl)amino;
  • R" is hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C2-C 4 -alkenyl, C2-C 4 -alkynyl or
  • R'" is hydrogen or Ci-C 4 -alkyl; is hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy,
  • Ci-C 4 -alkoxy-Ci-C 4 -alkyl Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, C2-C 4 -alkenyl,
  • R 2 independently of each other are hydrogen, halogen, OH, CN , Ci-C 4 -alkyl,
  • Ci-C 4 -haloalkyl Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -halo- alkoxy-Ci-C 4 -alkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -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-C 4 -alkyl,
  • Ci-C 4 -haloalkyl Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, (Ci-C 4 -alkoxy)carbonyl and di(Ci-C 4 - 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
  • abovementioned heterocycle include beside carbon atoms 1 , 2, 3 or 4 heteroatoms selected from the group of N, O and S, and wherein the abovementioned cycle is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, CN, OH, SH, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-C4-alkylthio; and
  • 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, N0 2 , d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy,
  • 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, O
  • 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 (see e.g. Chemistry A Eur. J. (201 1 ), 17(44), 12276-12279; Eur. J. Org. Chem. (2002), (19), 3243-3249; Synlett (2003), (3), 353-356; Chirality (2009), 21 (9), 836-842; or J. Org. Chem. (2008), 73(18), 7373-7375). Reduction of the nitrile group provides compounds AD-3.
  • 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. Justus Liebigs Annalen der Chemie (1949), 564, 49-54, Justus Liebigs Annalen der Chemie (1957), 605, 200-1 1 , J. Chem. Soc. (1959), 1780-2; or WO 2007/020381 ).
  • 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 LiAII-U 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 III, 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. UAIH4, 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. UAIH4, PhSiHs or H 2 and a catalyst
  • compounds AD-9 can be used to obtain compounds III, 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 III, 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
  • Tert-butyloxycarbonyl (BOC) protected tyrosine methyl ester AD-12 can be transformed to the corresponding biaryl ether AD-13 with suitable heteroaromatic groups Het-LG in analogy to WO 2005014534 A1 , WO 201 1 100285 A1 , Tetrahedron Letters (1994), 35(31 ), 5649-52.
  • the coupling of AD-13 with a 4-halopyrimidine II can be performed in analogy to J. Med. Chem. (201 1 ), 54(15), 5335-5348; Bioorg. Med. Chem. Lett. (201 1 ), 21 (6), 1741 -1743; US
  • 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.
  • Suitable catalysts are e.g. haldies such as NaF, KF, LiF, NaBr, KBr, LiBr, Nal, Kl, Lil; ionic liquids, such as imidazolium catalysts; transition metal catalysts like palladium, rhodium, ruthenium, iron, copper in the form of halides, pseudohalides, alkoxides, carboxylates (preferred acetate), complexes with dibenzylidene acetone and ligands like phosphine, phosphites, phosphoramidate ligands.
  • Preferred ligands are bidentate and sterically demanding
  • the catalysts are selected from 2,2'-bis(diphenyl- phosphanyl)-1 ,1 '-binaphthyl, 2,2'-Bis(diphenylphosphino)-1 ,1 '-biphenyl, 2,4',6'-diisopropyl-1 ,1 '- biphenyl-2-yldicyclohexylphosphine, 2-(dicyclohexylphosphino)-2',6'-dimethoxy-1 ,1 '-biphenyl, 1 ,1 -bis(diphenylphosphino)ferrocene, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 1 ,2- bis(diphenylphosphino)ethane (dppe), 1 ,3-propanediylbis[diphenylphosphine],
  • Suitable solvents are aromatic hydrocarbons such as toluene, 0-, m- and p-xylene;
  • halogenated hydro-carbons chlorobenzene, dichlorobenzene; ethers such as dioxane, anisole and THF; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert.
  • Suitable bases and their amounts are as described for the reaction with a phenethyl amine compound III, wherein X is -CR 3 R 4 -, as described above.
  • 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 eqivalents, preferred 1 .1 to 1 .5 equivalents of compounds II.
  • the phenyl acetic acid amide compounds III are known from the literature or are
  • 4-amino-pyrimidine compounds I la which are available by reaction of a chloro-pyrimidine II with excess of ammonia in analogy to methods described in WO 201 1/147066; WO 2006/135719; US 2005/0245530 A1 ; J. Chem. Soc. (1951 ), 3439-44; Helv. Chim. Act.
  • 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, OCHCI 2 , OCCI 3 , chlorofluoromethoxy,
  • dichlorofluoromethoxy chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3- fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3- dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3- trichloropropoxy, OCH 2 -C 2 F 5 , OCF 2 -C 2 F 5 , 1 -
  • 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, diethylamino, di-n-propylamino, diisopropylamino, N-ethyl-N-methylamino, N-(n-propyl)-N- methylamino, N-(isopropyl)-N methylamino, N-(n-butyl)-N-methylamino, N-(n-pentyl)-N- methylamino, N-(2-butyl)-N methylamino, N-(isobutyl)-N-methylamino, and the like.
  • di(Ci-C6-alkyl)amino refers to an amino radical carrying two identical or different Ci- C6-alkyl groups (as defined above
  • (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 C3-C8- 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-iso
  • a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-,
  • 6- or -7-yl hexahydroazepin-1 -, -2-, -3- or -4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-
  • 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.F2 and to the intermediates such as compounds II, III, lla and Ilia, wherein the substituents and variables (e.g.
  • R a2 , R a5 , R a6 , R, X, R 1 , R2, R 3 , R 4 , R A , R B , R D , 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 a5 is (Ci-C4-alkoxy)carbonyl; preferably R a5 is COOCH3, COOC 2 H 5 , COOCH 2 CH 2 CH 3 or COOCH(CH 3 ) 2 , particularly COOCH3 or COOC 2 H 5 .
  • R A , R B in radicals R a2 and R a6 independently of one another preferably are hydrogen or Ci-C4-alkyl.
  • R' in radicals R a2 and R a6 which may the same or different, are hydrogen, N H2, Ci-C4-alkyl or Ci-C4-alkoxy.
  • R" in radicals R a2 and R a6 are hydrogen, Ci-C 4 -alkyl.
  • R'" in radicals R a2 and R a6 are hydrogen or Ci- C 4 -alkyl.
  • R a2 and R a6 independently of each other are hydrogen, 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,
  • C3-C8-cycloalkyloxy or (Ci-C4-alkoxy)carbonyl more preferably hydrogen, halogen, CN , C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-alkoxy-Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2-alkoxy or (C1-C2- alkoxy)carbonyl; even more preferably hydrogen, F, CI, CH3, CH2CH3, CF3, CHFCH3, CN, OCH3, OCH2OCH3, CH2OCH3, COOCH3 and COOC 2 H 5 .
  • R a2 and R a6 independently of each other are 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,
  • R a2 and R a6 independently of each other are halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy or (Ci-C4-alkoxy)carbonyl, and it being possible that one of both, R a2 or R a6 , can in addition be hydrogen.
  • R a6 is halogen, CN, methy, ethyl or CH(CH3)2 and R a5 is as defined or preferably defined above.
  • R a6 is chlorine, CN, methy, ethyl or CH(CH3)2 and R a5 is as defined or preferably defined above.
  • R a6 is ethyl or CH(CH3)2 and R a5 is as defined or preferably defined above.
  • R a6 is ethyl or CH(CH3)2 and R a5 is COOMe or COOEt.
  • R a6 is CH(CH 3 )2 and R a5 is as defined or preferably defined above.
  • R a6 is ethyl and R a5 is as defined or preferably defined above.
  • R a6 is methyl and R a5 is as defined or preferably defined above.
  • R a6 is chlorine and R a5 is as defined or preferably defined above.
  • R A , R B in radical R independently of one another preferably are hydrogen or Ci- C 4 -alkyl.
  • R' in radical R is hydrogen, OH, NH 2 , Ci-C 4 -alkyl or Ci-C 4 -alkoxy.
  • Another preferred embodiment relates to compounds I wherein R is CH3.
  • X is preferably -CR 3 R 4 -, -CHCH3-,
  • R 3 and R 4 independently of each other are preferably hydrogen, halogen, CN, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy or Cs-Cs-cycloalkyl, more preferably hydrogen, halogen or Ci-C 4 -alkyl.
  • R' in radicals R 3 and/or R 4 is hydrogen, OH, NH 2 , Ci-C 4 -alkyl or Ci-C 4 -alkoxy.
  • X is selected from -CH 2 -, -CHCH3-, and -CH(CH 2 CH3)-, in particular X is -CH 2 - which compounds are of formula I.
  • X is -C(CHs)H-, which compounds are of formula I.B:
  • the moiety O-Het is bound in para-position to the phenylring, which compounds are of formula 1.1 :
  • 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 I.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-, 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.A1 :
  • X is -CH2-, n is 0, 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(CHs)-, 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.B1 :
  • X is -CH(CH3)-, n is 0, 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(CH3)2-, n is 0, 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)-, 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.D1 : a6 R H
  • X is -CH(CH2CH3)-, n is 0, 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.
  • X is -CH(CN)-, 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.E1 :
  • X is -CH(CN)-, n is 0, 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.E2:
  • 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, CH3, CH2CH3 or OCH3, 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, NH2, Ci-C4-alkyl or Ci-C4-alkoxy.
  • R" in radicals R 1 , R 2 , R 3 , R 4 , R b and/or R c which may the same or different, are hydrogen, Ci-C4-alkyl.
  • R'" in radicals R 1 , R 2 , R 3 , R 4 , R b and/or R c which may the same or different, 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 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.
  • 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-haloalkoxy and C1-C4- alkoxy-Ci-C4-alkyl.
  • 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.
  • Het is a 6-membered heteroaryl
  • 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 pyridyl radical that is selected from pyridin-2-yl, pyridin-3-yl and pyridin-4-yl, and wherein the aforementioned pyridyl radicals are unsubstituted or carry 1 , 2, 3 or 4 identical or different substituents R c .
  • Het is pyridin-2-yl, which is unsubstituted or carries one or two radicals R c .
  • Het is pyridin-4-yl, which is unsubstituted or carries one or two radicals R c .
  • 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.
  • 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 unsubstituted.
  • 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 d-C 4 -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 d-C 4 -haloalkyl and selected from d-haloalkyl, d-haloalkyl, d-haloalkyl and d-haloalkyl. More preferably, R c is d-haloalkyl and selected from fluormethyl, difluormethyl, trifluormethyl, chlormethyl, dichlormethyl and trichlormethyl, and in particular, R c is trifluormethyl.
  • R c is d-C 4 -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.
  • halomethoxy such as difluormethoxy, trifluormethoxy, dichlormethoxy and trichlormethoxy
  • haloethoxy such as 2,2-difluorethoxy, 2,2,2-trifluorethoxy, 2,2-dichlorethoxy and 2,2,2-trichlorethoxy
  • R c is Cs-Cs-cycloalkyl, and in particular, R c is cyclopropyl.
  • R c is phenyl
  • R c is phenoxy
  • R c is phenoxy-Ci-C4-alkyl and selected from phenoxymethyl, 1 - phenoxy-ethyl and 2-phenoxyethyl.
  • 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 1.2 wherein:
  • R a5 is COOCHs or COOC 2 H 5 ;
  • R a2 , R a6 independently of each other are hydrogen, halogen, CN or Ci-C4-alkyl;
  • n indicates the number of substituents R b on the phenyl ring and n is 0 or 1 ;
  • R b is halogen or Ci-C4-haloalkyl
  • Het is a pyridinyl, wherein the pyridinyl is unsubstituted or carries 1 or 2 groups R c :
  • R c is halogen, Ci-C4-haloalkyl or Ci-C4-haloalkoxy
  • Table 1 Compounds of formula I.A1 , wherein Het is H-1 , and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 2 Compounds of formula I.A1 , wherein Het is H-2, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 3 Compounds of formula I.A1 , wherein Het is H-3, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 4 Compounds of formula I.A1 , wherein Het is H-4, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 5 Compounds of formula I.A1 , wherein Het is H-5, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 6 Compounds of formula I.A1 , wherein Het is H-6, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 7 Compounds of formula I.A1 , wherein Het is H-7, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 8 Compounds of formula I.A1 , wherein Het is H-8, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 9 Compounds of formula I.A1 , wherein Het is H-9, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 10 Compounds of formula I.A1 , wherein Het is H-10, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 1 1 Compounds of formula I .A1 , wherein Het is H-1 1 , and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 12 Compounds of formula I.A1 , wherein Het is H-12, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 13 Compounds of formula I.A1 , wherein Het is H-13, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 14 Compounds of formula I.A1 , wherein Het is H-14, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 15 Compounds of formula I.A1 , wherein Het is H-15, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 16 Compounds of formula I.A1 , wherein Het is H-16, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 17 Compounds of formula I.A1 , wherein Het is H-17, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 18 Compounds of formula I.A1 , wherein Het is H-18, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 19 Compounds of formula I.A1 , wherein Het is H-19, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 20 Compounds of formula I.A1 , wherein Het is H-20, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 21 Compounds of formula I.A1 , wherein Het is H-21 , and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 22 Compounds of formula I.A1 , wherein Het is H-22, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 23 Compounds of formula I.A1 , wherein Het is H-23, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 24 Compounds of formula I.A1 , wherein Het is H-24, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 25 Compounds of formula I.A1 , wherein Het is H-25, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 26 Compounds of formula I.A1 , wherein Het is H-26, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 27 Compounds of formula I.A1 , wherein Het is H-27, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 28 Compounds of formula I.A1 , wherein Het is H-28, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 29 Compounds of formula I.A1 , wherein Het is H-29, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 30 Compounds of formula I.A1 , wherein Het is H-30, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 31 Compounds of formula I.A1 , wherein Het is H-31 , and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 32 Compounds of formula I.A1 , wherein Het is H-32, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 33 Compounds of formula I.A1 , wherein Het is H-33, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 34 Compounds of formula I.A1 , wherein Het is H-34, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 35 Compounds of formula I.A1 , wherein Het is H-35, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 36 Compounds of formula I.A1 , wherein Het is H-36, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 37 Compounds of formula I.A1 , wherein Het is H-37, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Table 38 Compounds of formula I.A1 , wherein Het is H-38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 39 to 76 Compounds of formula I.A2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 77 to 1 14 Compounds of formula I.B1 , wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 1 15 to 152 Compounds of formula I.B2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 153 to 190 Compounds of formula I.C1 , wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 191 to 228 Compounds of formula I.C2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 229 to 266 Compounds of formula I.D1 , wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 267 to 304 Compounds of formula I.D2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 305 to 342 Compounds of formula I.E1 , wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 343 to 380 Compounds of formula I.E2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 381 to 418 Compounds of formula I.F1 , wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table A.
  • Tables 419 to 456 Compounds of formula I.F2, wherein Het is defined as in Tables 1 to 38, and the meaning of R a2 , R a5 and R a6 for each compound corresponds to one line of Table 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 compositions thereof, respectively is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
  • 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.
  • auxin herbicides such as
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ALS inhibitors e.g. described in Pest Managem. Sci.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • RoundupReady® glyphosate-tolerant
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3- hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultiv
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA
  • plants are also covered that contain by the use of recombinant DNA
  • the compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. white rust
  • vegetables e. g. A. Candida
  • sunflowers e. g. A. tragopogonis
  • Alternaria spp. Alternaria leaf spot) on vegetables, rape (A. 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. hordei on barley; 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.
  • Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus
  • anamorph Helminthosporium of Bipolaris
  • spp. leaf spots
  • corn C. carbonum
  • cereals e. g. C. sativus, anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus, anamorph: H.
  • gossypii corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C.
  • coccodes black dot
  • beans e. g. C. lindemuthianum
  • soybeans e. g. C. truncatum or C. gloeosporioides
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice
  • Corynespora cassiicola leaf spots
  • Cycloconium spp. e. g. C. oleaginum on olive trees
  • Cylindrocarpon spp. e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.
  • Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum),
  • fujikuroi Bakanae disease
  • G. gossypii Gossypii on cotton
  • Grainstaining complex on rice Guignardia bidwellii (black rot) on vines
  • Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H.
  • Monilinia spp. e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P.
  • soybeans e. g. P. gregata: stem rot
  • Phoma lingam root and stem rot
  • P. betae root rot, leaf spot and damping-off
  • sugar beets e. g. P. viticola: can and leaf spot
  • soybeans e. g. stem rot: P.
  • phaseoli, teleomorph Diaporthe phaseolorum
  • Physoderma maydis brown spots
  • Phytophthora spp. wilt, root, leaf, fruit and stem root
  • various plants such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death);
  • Plasmodiophora brassicae club root
  • cabbage rape, radish and other plants
  • Plasmopara spp. e.
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae
  • cereals e. g. wheat or barley
  • Pseudoperonospora downy mildew
  • Pseudopezicula tracheiphila red fire disease or .rotbrenner', anamorph: Phialophora
  • Puccinia spp. rusts
  • 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, soy- beans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphani- dermatum); 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
  • 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. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp.
  • 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.
  • 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 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), emulsions (e.g. EW, EO,
  • ES ES
  • ME capsules
  • pastes e.g. CS, ZC
  • pastes pastilles
  • wettable powders or dusts e.g. WP, SP
  • compositions types are defined in the following abbreviations: WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • compositions are prepared in a known manner, such as described by Mollet and
  • 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. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids;
  • phosphonates 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.
  • 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.
  • sulfonates 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 alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • 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
  • 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 polyethyleneamines.
  • 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, carboxymethylcellulose), 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
  • 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.
  • composition types and their preparation are:
  • Water-soluble concentrates (SL, LS) 10-60 wt% of a compound I and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%.
  • the active substance dissolves upon dilution with water.
  • a compound I and 1 -10 wt% dispersant e. g. polyvinylpyrrolidone
  • a compound I and 1 -10 wt% dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylben- zenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • a compound I In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1 -2 wt% thickener e.g. xanthan gum
  • 50-80 wt% of a compound I are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water- dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • a compound I 5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4'-diisocyanatae are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS
  • Dustable powders (DP, DS)
  • 1 -10 wt% of a compound I are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • a compound I is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • a compound I 1 -50 wt% of a compound I are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • auxiliaries such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, 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.
  • 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 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.
  • strobilurins e.g. strobilurins: azoxystrobin, coumethoxy- strobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxy- strobin/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-di- chlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide, pyribencarb, triclopyricarb/ch
  • - inhibitors of complex II e. g. carboxamides: benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N- (2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, N-[9- (dichloromethylene)-l ,2,3,4-tetrahydro-1 ,4-methanonaphthalen-5-yl]-3-(
  • respiration inhibitors e.g. complex I, uncouplers: diflumetorim, (5,8-difluoro- quinazolin-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;
  • 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;
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-
  • 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;
  • - 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;
  • 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;
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles
  • guanidine dodine, dodine free base, guazatine, guazatine- acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon;
  • 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;
  • phosphonates fosetyl, fosetyl-aluminum, phosphorous acid and its salts;
  • 4-thiazolecarboxamide 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3- [5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole), N-(6-methoxy- pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2- yl)-2-methyl-1 H-benzoimidazole,
  • Antifungal biocontrol agents plant bioactivators: Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany), Aspergillus flavus (e.g.
  • AFLAGUARD® from Syngenta, CH
  • Aureobasidium pullulans e.g. BOTECTOR® from bio-ferm GmbH, Germany
  • Bacillus pumilus e.g. NRRL Accession No. B-30087 in
  • Bacillus subtilis e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest Inc., USA
  • Bacillus subtilis var. amyloliquefaciens FZB24 e.g. TAEGRO® from Novozyme Biologicals, Inc., USA
  • 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.
  • 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, France), Cryptococcus albidus (e.g.
  • Fusarium oxysporum e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France
  • 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.
  • Pythium oligandrum DV74 e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.
  • Reynoutria sachlinensis e.g. REGALIA® from Marrone Biolnnovations, USA
  • Talaromyces flavus V1 17b e.g. PROTUS® from Prophyta, Germany
  • Trichoderma asperellum SKT-1 e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd., Japan
  • T. atroviride LC52 e.g. SENTINEL® from Agrimm
  • 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-22 e.g. PLANTSHIELD® der Firma BioWorks Inc., USA
  • T. harzianum TH 35 e.g. ROOT PRO® from Mycontrol Ltd., Israel
  • T-39 e.g. TRICHODEX® and TRICHODERMA 2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel
  • T. harzianum and T. viride e.g. TRICHOPEL 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., Brazil), T. virens GL-21 (e.g. SOILGARD® from Certis LLC, USA), 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);
  • T. viride TV1 e.g. T. viride TV
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • - (thio)carbamates asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb,
  • 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,
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid,
  • amicarbazone amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,
  • fenoxasulfone fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon,
  • oxaziclomefone pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3- methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1 -yl)-phenoxy]-pyridin-2- yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methyl-
  • 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, OZ.
  • 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,
  • - 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) (component 2), in particular one further fungicide, e. g.
  • Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.
  • 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 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;
  • 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.
  • Preference is also given to 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
  • Table D Composition comprising one indiviualized compound I and one further active substance from groups A) to O)

Abstract

La présente invention a trait à des composés de pyrimidine fongicides (I), à leur utilisation et à des méthodes permettant de combattre des champignons phytopathogènes. La présente invention a également trait à des semences traitées avec au moins un tel composé. De plus, l'invention a trait à des procédés de préparation des composés de formule (I).
PCT/EP2013/051859 2012-02-03 2013-01-31 Composés de pyrimidine fongicides WO2013113791A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP12153758 2012-02-03
EP12153758.3 2012-02-03
EP12154196.5 2012-02-07
EP12154196 2012-02-07

Publications (1)

Publication Number Publication Date
WO2013113791A1 true WO2013113791A1 (fr) 2013-08-08

Family

ID=47624098

Family Applications (3)

Application Number Title Priority Date Filing Date
PCT/EP2013/051855 WO2013113788A1 (fr) 2012-02-03 2013-01-31 Composés de pyrimidine fongicides
PCT/EP2013/051859 WO2013113791A1 (fr) 2012-02-03 2013-01-31 Composés de pyrimidine fongicides
PCT/EP2013/051854 WO2013113787A1 (fr) 2012-02-03 2013-01-31 Composés de pyrimidine fongicides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/051855 WO2013113788A1 (fr) 2012-02-03 2013-01-31 Composés de pyrimidine fongicides

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/051854 WO2013113787A1 (fr) 2012-02-03 2013-01-31 Composés de pyrimidine fongicides

Country Status (2)

Country Link
AR (3) AR089883A1 (fr)
WO (3) WO2013113788A1 (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
CN111789120A (zh) * 2020-07-29 2020-10-20 湖南省植物保护研究所 杀菌剂抑霉唑离子液、及其制备方法和应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105722833A (zh) * 2013-09-16 2016-06-29 巴斯夫欧洲公司 杀真菌的嘧啶化合物
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

Citations (111)

* 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
GB2016466A (en) 1978-03-01 1979-09-26 Nippon Chemiphar Co Acetic acid derivatives and processes for producing the same
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
EP0276406A1 (fr) * 1986-12-12 1988-08-03 Bayer Ag 4-Amino-pyrimidines substitués
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0519211A1 (fr) * 1991-05-17 1992-12-23 Hoechst Schering AgrEvo GmbH 4-Aminopyrimidines substituées, procédé pour leur préparation et leur utilisation comme parasiticide
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
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
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
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
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
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
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
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
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
WO2005011601A2 (fr) 2003-08-01 2005-02-10 Pfizer Products, Inc. Composes heteroaryle a 6 elements pour traiter des troubles neurodegeneratifs
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
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
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
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
US20050245530A1 (en) 2004-04-23 2005-11-03 Borzilleri Robert M Monocyclic heterocycles as kinase inhibitors
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
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
WO2006074884A1 (fr) 2005-01-14 2006-07-20 F.Hoffmann-La Roche Ag Derives de thiazole-4-carboxamide en tant qu'antagonistes du mglur5
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
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
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
WO2006135719A1 (fr) 2005-06-10 2006-12-21 Janssen Pharmaceutica N.V. Aminopyrimidines comme modulateurs de kinase
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
WO2007075598A2 (fr) 2005-12-20 2007-07-05 Incyte Corporation N-hydroxyamidinoheterocycles en tant que modulateurs d'indoleamine 2,3-dioxygenase
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
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
WO2008039520A2 (fr) 2006-09-26 2008-04-03 Synta Pharmaceuticals Corp. Composés cycliques condensés pour utilisations associées à l'inflammation et aux troubles immunitaires
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
WO2010000527A1 (fr) 2008-07-04 2010-01-07 Robert Bosch Gmbh Vanne magnétique pour un injecteur de carburant et injecteur de carburant
US20100022538A1 (en) 2008-01-22 2010-01-28 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
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
US20100063063A1 (en) 2008-09-11 2010-03-11 Pfizer Inc Substituted Heteroaryls
US20100068197A1 (en) 2008-07-11 2010-03-18 Myriad Pharmaceuticals, Inc. Pharmaceutical compounds as inhibitors of cell proliferation and the use thereof
WO2010058030A1 (fr) 2008-11-24 2010-05-27 Boehringer Ingelheim International Gmbh Nouveaux composés
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
WO2011025505A1 (fr) 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
US20110054173A1 (en) 2009-08-31 2011-03-03 Dow Agrosciences Llc Pteridines and their use as agrochemicals
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
WO2011147066A1 (fr) 2010-05-26 2011-12-01 四川大学 Dérivés arylaminés de purine, leur procédé de préparation et leur utilisation pharmaceutique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA80437C2 (en) 2002-09-19 2007-09-25 Lilly Co Eli Diaryl ethers as opioid receptor antagonist

Patent Citations (112)

* 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
GB2016466A (en) 1978-03-01 1979-09-26 Nippon Chemiphar Co Acetic acid derivatives and processes for producing the same
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
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
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
EP0276406A1 (fr) * 1986-12-12 1988-08-03 Bayer Ag 4-Amino-pyrimidines substitués
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0519211A1 (fr) * 1991-05-17 1992-12-23 Hoechst Schering AgrEvo GmbH 4-Aminopyrimidines substituées, procédé pour leur préparation et leur utilisation comme parasiticide
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
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
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
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
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
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
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
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
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
WO2005011601A2 (fr) 2003-08-01 2005-02-10 Pfizer Products, Inc. Composes heteroaryle a 6 elements pour traiter des troubles neurodegeneratifs
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
US20050245530A1 (en) 2004-04-23 2005-11-03 Borzilleri Robert M Monocyclic heterocycles as kinase inhibitors
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
WO2006074884A1 (fr) 2005-01-14 2006-07-20 F.Hoffmann-La Roche Ag Derives de thiazole-4-carboxamide en tant qu'antagonistes du mglur5
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
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
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
WO2006135719A1 (fr) 2005-06-10 2006-12-21 Janssen Pharmaceutica N.V. Aminopyrimidines comme modulateurs de kinase
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
WO2007075598A2 (fr) 2005-12-20 2007-07-05 Incyte Corporation N-hydroxyamidinoheterocycles en tant que modulateurs d'indoleamine 2,3-dioxygenase
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
WO2008034142A2 (fr) 2006-09-15 2008-03-20 Reviva Pharmaceuticals, Inc. Synthèse, procédés d'utilisation et compositions de cycloalkylméthylamines
WO2008039520A2 (fr) 2006-09-26 2008-04-03 Synta Pharmaceuticals Corp. Composés cycliques condensés pour utilisations associées à l'inflammation et aux troubles immunitaires
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
US20100022538A1 (en) 2008-01-22 2010-01-28 Dow Agrosciences Llc 5-fluoro pyrimidine derivatives
WO2009156100A1 (fr) 2008-06-24 2009-12-30 Sanofi-Aventis Isoquinolines et isoquinolinones substituées utilisées comme inhibiteurs de rho-kinase
WO2010000527A1 (fr) 2008-07-04 2010-01-07 Robert Bosch Gmbh Vanne magnétique pour un injecteur de carburant et injecteur de carburant
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
US20100063063A1 (en) 2008-09-11 2010-03-11 Pfizer Inc Substituted Heteroaryls
WO2010058030A1 (fr) 2008-11-24 2010-05-27 Boehringer Ingelheim International Gmbh Nouveaux composés
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
WO2011025505A1 (fr) 2009-08-31 2011-03-03 Dow Agrosciences Llc Ptéridines et leur utilisation comme produits agrochimiques
US20110054173A1 (en) 2009-08-31 2011-03-03 Dow Agrosciences Llc Pteridines and their use as agrochemicals
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
WO2011147066A1 (fr) 2010-05-26 2011-12-01 四川大学 Dérivés arylaminés de purine, leur procédé de préparation et leur utilisation pharmaceutique

Non-Patent Citations (94)

* Cited by examiner, † Cited by third party
Title
"McCutcheon's, Vol.1: Emulsifiers & Detergents", 2008, MCCUTCHEON'S DIRECTORIES
"Technical Monograph No. 2, 6th Ed.", May 2008, CROPLIFE INTERNATIONAL, article "Catalogue of pesticide formulation types and international coding system"
61, PEST MANAGEM. SCI., 2005, pages 269
61, PEST MANAGEM. SCI., 2005, pages 286
64, PEST MANAGEM. SCI., 2008, pages 326
64, PEST MANAGEM. SCI., 2008, pages 332
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
AUSTRAL. J. AGRICULT. RES, vol. 58, 2007, pages 708
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
BIOORG. MED. CHEM., vol. 16, no. 8, 2008, pages 4600 - 4616
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., 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., no. 19, 2002, pages 3243 - 3249
EUR. J. ORG. CHEM., vol. 5, 2004, pages 1025 - 1032
HELV. CHIM. ACT., vol. 34, 1951, pages 835 - 40
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., 1951, pages 3439 - 44
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. 30, no. 4, 1987, pages 720 - 1
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. 47, no. 3, 2004, pages 663 - 672
J. MED. CHEM., vol. 50, no. 20, 2007, pages 5003 - 5011
J. MED. CHEM., vol. 54, no. 15, 2011, pages 5335 - 5348
J. MED. CHEM., vol. 54, no. 9, 2011, pages 3241 - 3250
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
J. ORG. CHEM., vol. 76, no. 6, 2011, pages 1546 - 1553
JINGXI HUAGONG ZHONGJIANTI, vol. 40, no. 3, 2010, pages 26 - 28
JOURNAL OF MEDICINAL CHEMISTRY, vol. 53, no. 13, 2010, pages 5012 - 5024
JOURNAL OF ORGANIC CHEMISTRY, vol. 52, no. 21, 1987, pages 4689 - 93
JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 564, 1949, pages 49 - 54
JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 605, 1957, pages 200 - 11
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
MOLLET; GRUBEMANN: "Formulation technology", 2001, WILEY VCH
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. 12, no. 23, 2010, pages 5570 - 5572
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
ORGANOMETALLICS, vol. 30, no. 20, pages 5442 - 5451
O'ZBEKISTON KIMYO JURNALI, vol. 4, 2004, pages 3 - 6
PEST MANAGEM. SCI., vol. 61, 2005, pages 246
PEST MANAGEM. SCI., vol. 61, 2005, pages 258
PEST MANAGEM. SCI., vol. 61, 2005, pages 277
PESTIC. SCI., vol. 44, no. 4, 1995, pages 341 - 355
SCIENCE OF SYNTHESIS, vol. 16, 2004, pages 379 - 572
SCIENCE, vol. 316, 2007, pages 1185
SYNLETT, 2008, pages 1857 - 1861
SYNLETT, no. 3, 2003, pages 353 - 356
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
WEED SCI., vol. 57, 2009, pages 108

Cited By (4)

* 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
CN111789120A (zh) * 2020-07-29 2020-10-20 湖南省植物保护研究所 杀菌剂抑霉唑离子液、及其制备方法和应用
CN111789120B (zh) * 2020-07-29 2022-04-01 湖南省植物保护研究所 杀菌剂抑霉唑离子液、及其制备方法和应用

Also Published As

Publication number Publication date
AR089882A1 (es) 2014-09-24
WO2013113788A1 (fr) 2013-08-08
WO2013113787A1 (fr) 2013-08-08
AR089883A1 (es) 2014-09-24
AR089881A1 (es) 2014-09-24

Similar Documents

Publication Publication Date Title
US9072301B2 (en) Fungicidal pyrimidine compounds
AU2016299729B2 (en) Pyridine compounds useful for combating phytopathogenic fungi
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
EP2935225A1 (fr) Composés imidazole et triazole substitués en [1,2,4]
WO2014095381A1 (fr) Composés imidazolyl et triazolyl fongicides
WO2013113776A1 (fr) Composés de pyrimidine fongicides
WO2015036059A1 (fr) Composés fongicides de pyrimidine
WO2013113791A1 (fr) Composés de pyrimidine fongicides
WO2013113781A1 (fr) Composés de pyrimidine fongicides i
JP2015512891A (ja) 殺菌性ピリミジン化合物
WO2014095637A1 (fr) Composés imidazole et triazole substitués en [1,2,4]
WO2013113773A1 (fr) Composés fongicides de pyrimidine
WO2013113716A1 (fr) Composés de pyrimidine fongicides
WO2013113778A1 (fr) Composés de pyrimidine fongicides
WO2013135672A1 (fr) Composés de pyrimidine fongicides
WO2013113719A1 (fr) Composés de pyrimidine fongicides ii
WO2013113720A1 (fr) Composés de pyrimidine fongicides
WO2013113782A1 (fr) Composés de pyrimidine fongicides
EP2746264A1 (fr) [1,2,4]triazole substitué et composés d'imidazole
EP2746274A1 (fr) Composés de [1,2,4] triazole substitué
EP2745691A1 (fr) Composés d'imidazole substitués et leur utilisation comme 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: 13701658

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: 13701658

Country of ref document: EP

Kind code of ref document: A1