WO2021094906A1 - Novel agrochemical composition comprising 4-substituted phenylamidine compounds - Google Patents

Novel agrochemical composition comprising 4-substituted phenylamidine compounds Download PDF

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Publication number
WO2021094906A1
WO2021094906A1 PCT/IB2020/060553 IB2020060553W WO2021094906A1 WO 2021094906 A1 WO2021094906 A1 WO 2021094906A1 IB 2020060553 W IB2020060553 W IB 2020060553W WO 2021094906 A1 WO2021094906 A1 WO 2021094906A1
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Prior art keywords
methyl
phenyl
trifluoromethyl
oxadiazol
ethyl
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PCT/IB2020/060553
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French (fr)
Inventor
Vishal A. MAHAJAN
Maruti Naik
Santosh Shridhar AUTKAR
Ruchi GARG
Vishwanath GADE
Alexander G. M. KLAUSENER
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Pi Industries Ltd.
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Publication of WO2021094906A1 publication Critical patent/WO2021094906A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines

Definitions

  • the present invention relates to a novel agrochemical composition. More particularly, the present invention relates to a novel agrochemical composition which comprises a mixture of one or more phenylamidine compounds of formula (I) as a component (1) and one or more fungicidally active compounds as component (2). Further, the present invention relates to a method for controlling phytopathogenic fungi of plants, to the use of a novel agrochemical composition according to the invention for the treatment of one or more seeds, to a method for protecting one or more seeds and to the corresponding treated seeds.
  • phenylamidine compounds as a fungicide was known from the following prior art documents: W02000046184, W02003093224, WO2017102635, WO2018069841, WO2018108998 and
  • W02018091430 disclose arylamidine derivatives as fungicides.
  • WO2018228896, W02015121802, W02007031507, W02005089547 and W02003024219 disclose the fungicide mixtures comprising at least one arylamidine derivative and a further selected known fungicide.
  • the combinations of fungicides are often used to facilitate disease control and to retard resistance development. It is desirable to enhance the activity spectrum and the efficacy of disease control by using mixtures of active ingredients that provide a combination of curative, systemic and preventative control of plant pathogens. Also desirable are combinations that provide greater residual efficvacy to allow for extended spray intervals. It is also very desirable to combine fungicidal agents that inhibit different biochemical pathways in the fungal pathogens to retard development of resistance to any one particular plant disease control agent.
  • Fungicides that effectively control plant pathogens with a reduced quantity of chemical agent released in the environment are always desirable. Also there is constant need to widen the spectrum of activity, reduce toxicity and lower application rates.
  • the present invention provides agrochemical compositions which in some aspects at least achieve the stated objective.
  • the novel agrochemical compositions according to the invention not only bring about the additive enhancement of the spectrum of action with respect to the phytopathogens to be controlled, that was in principle to be expected, but also achieves a synergistic effect.
  • the synergistic effect of the agrochemical compositions of the present invention helps to reduce the application rate of component (1) and component (2) by maintaining the level of efficacy even if the two individual compounds alone have become ineffective at such low application rates. Also it allows a substantial broadening of the spectrum of phytopathogens that can be controlled by, at the same time, increasing the safety in use.
  • the agrochemical compositions according to the invention have further surprising properties which, in a wider sense, may also be called synergistic, such as, for example: broadening of the activity spectrum to other insects, nematodes and/or phytopathogens, for example to resistant strains of plant diseases; lower application rates of the active compounds; sufficient control of pests with the aid of the agrochemical composition according to the invention even at application rates where the individual compounds show virtually no activity; advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage stability and light stability; advantageous residue formation; improved toxicological or eco-biological behavior; improved properties of the so called effects on plant physiology, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, lower phytotoxicity, mobilization of the defense system of the
  • novel agrochemical compositions according to the invention contribute considerably to keeping young cereal stands healthy, which increases, for example, the winter survival of the cereal seed treated, and also safeguards quality and yield.
  • novel agrochemical compositions according to the invention may contribute to enhanced systemic action. Even if the individual compounds of the combination do not have sufficient systemic properties, the novel agrochemical composition according to the invention may still have this property. In a similar manner, the novel agrochemical composition according to the invention may result in higher long lasting efficacy of the fungicidal and/or insecticidal and/or nematicidal action.
  • the present invention provides a novel agrochemical composition comprising:
  • R 1 is selected from the group consisting of G-G-alkyl, C 2 -Ce-alkenyl, C 3 -C 6 -cycloalkyl-Ci-C 3 - alkyl and C 3 -C 6 -cycloalkyl;
  • R 2 is independently selected from the group consisting of C 2 -Ce-alkyl, C 2 -Ce-alkenyl, C 3 G- cycloalkyl-Ci-C 3 -alkyl and C 3 -C 6 -cycloalkyl;
  • R 3 and R 4 are independently selected from the group consisting of halogen, cyano, G-G-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy and C 3 -C 6 -cycloalkyl;
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C 3 -alkyl, Ci-C 3 -haloalkyl and Ci-C 3 -alkoxy; or
  • R’ is selected from the group consisting of hydrogen, Ci-C 3 -alkyl, C 3 -C 6 -cycloalkylalkyl and Ci- C 3 -alkoxy;
  • R 7 is selected from the group consisting of hydrogen, halogen, cyano, G-G-alkyl, C 1 -G- haloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, C 3 -C 8 - cycloalkyl and C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl; m represent integers 0, 1, 2, 3 or 4; or salts, AG x ides, metal complexes or stereoisomers thereof; and
  • the present invention provides a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, comprising the step of applying at least one novel agrochemical composition according to the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
  • Hydrogen Preferably, the definition of hydrogen encompasses also isotopes of hydrogen, preferably deuterium and tritium, more preferably deuterium.
  • Halogen (also in combinations such as haloalkyl, haloalkoxy etc.) fluorine, chlorine, bromine and iodine, and preferably fluorine, chlorine, bromine and more preferably fluorine, chlorine;
  • Alkyl (including in combinations such as alkylthio, alkoxy etc.) saturated, straight-chain or branched hydrocarbyl radicals having 1 to 6 carbon atoms, for example Ci-Ce-alkyl, such as methyl, ethyl, propyl,
  • alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl.
  • Haloalkyl (including in combinations such as haloalkylthio, haloalkoxy etc.) straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above, for example Ci-C3-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1- bromoethyl, 1-lluoroethyl, 2-l uoroethyl, 2,2-dil uoroethyl, 2,2,2-trilluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2-difluoroethyl, 2,2-d
  • Halomethyl a methyl group, where some or all of the hydrogen atoms in these group may be replaced by halogen atoms as specified above, for example (but not limited to) chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, and preferably trifluoromethyl.
  • cycloalkyl means alkyl closed to form a ring. Non-limiting examples include but are not limited to cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • alkoxy used either alone or in compound words included Ci-Ce alkoxy.
  • alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1 ,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1-methylpropoxy and l-ethy
  • the compounds of formula (I) can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. If applicable, compounds of formula (I) comprise both the E and the Z isomers, and also the threo and erythro, and the optical isomers, any mixtures of these isomers, and the possible tautomeric forms.
  • stereoisomers such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers.
  • compounds of formula (I) comprise both the E and the Z isomers, and also the threo and erythro, and the optical isomers, any mixtures of these isomers, and the possible tautomeric forms.
  • any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound.
  • the invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic” denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions.
  • the diastereomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.
  • any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound.
  • the invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
  • the geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the art.
  • the compounds of formula (I) can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents of ring B.
  • the invention thus relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions.
  • the syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.
  • the compound of formula (I) carry amidine groups which induce basic properties. Thus, these compounds can be reacted with acids to give salts.
  • inorganic acids examples include hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as NaHSCb and KHSO4.
  • hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide
  • sulfuric acid phosphoric acid and nitric acid
  • acidic salts such as NaHSCb and KHSO4.
  • Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms), arylsulfonic acids or - disulfonic acids (aromatic groups, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic
  • radical definitions and explanations given above in general terms or stated within preferred ranges can, however, also be combined with one another as desired, i.e. including between the particular ranges and prefrred ranges. They apply both to the end products and correspondingly to precursors and intermediates. In addition, individual definitions may not apply.
  • the present invention provides a novel agrochemical composition
  • a novel agrochemical composition comprising mixture of component (1) and component (2), wherein component (1) is a at least one compound of formula (I) Formula (I) wherein,
  • R 1 is selected from the group consisting of Ci-CValkyk C 2 -Ce-alkenyl, C 3 -C 6 -cycloalkyl-Ci-C 3 -alkyl and C 3 -Cr, -cycloalkyl ;
  • R 2 is independently selected from the group consisting of C 2 -Ce-alkyl, C 2 -Ce-alkenyl, C 3 -C 6 -cycloalkyl- Ci-C 3 -alkyl and C 3 -C 6 -cycloalkyl;
  • R 3 and R 4 are independently selected from the group consisting of halogen, cyano, C CValkyk Ci-Ce- haloalkyl, Ci-Ce-alkoxy and C 3 -C 6 -cycloalkyl;
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C 3 -alkyl and Ci-C 3 -alkoxy; or
  • R’ is selected from the group consisting of hydrogen, Ci-C 3 -alkyl, C 3 -C 6 -cycloalkylalkyl and Ci- C 3 -alkoxy;
  • R 7 is selected from the group consisting of hydrogen, halogen, cyano, C CValkyk CVCVhaloalkyk Ci- Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, CVCVcycloalkyl and C 3 -C 6 - cycloalkyl-Ci-C 3 -alkyl; m represent integers 0, 1, 2, 3 or 4; or salts, N- oxides, metal complexes or stereoisomers thereof; and component (2) is a at least one further active compound selected from the following groups:
  • the component (1) is a at least one compound of formula (I) wherein,
  • R 1 is selected from the group consisting of methyl, ethyl, isopropyl and cyclopropyl;
  • R 2 is selected from the group consisting of ethyl, isopropyl, cyclopropyl and cyclopropylmethyl;
  • R 3 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl and cyclopropyl;
  • R 4 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy and cyclopropyl;
  • R 5 and R 6 are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, halomethyl and methoxy;
  • R 7 is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy and cyclopropyl; m represent integers 0, 1, 2, 3 or 4; or salts, N- oxides, metal complexes or stereoisomers thereof; and component (2) is a at least one further active compound selected from the following groups: (A) inhibitors of the ergosterol synthesis,
  • the compound of formula (I) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
  • the component (2) is a at least one further active compound selected from the following groups:
  • the component (2) is at least one further active compound selected from the following groups:
  • the component (2) is at least one further active compound selected from the following groups:
  • Preferred novel agrochemical composition according to the invention comprises at least one further active compound (2) selected from:
  • Inhibitors of the ergosterol biosynthesis for example, (A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A004) fenhexamid, (A005) fenpropidin, (A006) fenpropimorph, (A007) fenpyrazamine, (A008) fluquinconazole, (A009) flutriafol, (A010) imazalil, (A011) imazalil sulfate, (A012) ipconazole, (A013) metconazole, (A014) myclobutanil, (A015) paclobutrazol, (A016) prochloraz, (A017) propiconazole, (A018) prothioconazole, (A019) Pyrisoxazole, (A020) spiroxamine, (A021) tebuconazole, (A022)
  • (B) Inhibitors of the respiratory chain at complex I or II for example, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B004) carboxin, (B005) fluopyram, (B006) flutolanil, (B007) fluxapyroxad, (B008) furametpyr, (B009) Isofetamid, (B010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B014) isopyrazam (syn-e
  • (C) Inhibitors of the respiratory chain at complex III for example, (COOl) ametoctradin, (C002) amisulbrom, (C003) azoxystrobin, (C004) coumethoxystrobin, (C005) coumoxystrobin, (C006) cyazofamid, (C007) dimoxystrobin, (C008) enoxastrobin, (C009) famoxadone, (COIO) fenamidone, (C011) flufenoxystrobin, (C012) fluoxastrobin, (C013) kresoxim-methyl, (C014) metominostrobin, (C015) orysastrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C018) pyrametostrobin, (C019) pyraoxystrobin, (C020) trifloxystrobin, (C021) (2E)-2- ⁇ 2-[( ⁇ [(
  • (D) Inhibitors of the mitosis and cell division for example, (D001) carbendazim, (D002) diethofencarb, (D003) ethaboxam, (D004) fluopicolide, (D005) pencycuron, (D006) thiabendazole, (D007) thiophanate-methyl, (D008) zoxamide, (D009) 3-chloro-4-(2,6-difluorophenyl)-6- methyl-5- phenylpyridazine, (D010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6- methylpylidazine, (D011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl)pyridazine, (DO 12) 4-(2- bromo-4-fluorophenyl)
  • (E) Compounds capable to have a multisite action for example (E001) bordeaux mixture, (E002) captafol, (E003) captan, (E004) chlorothalonil, (E005) copper hydroxide, (E006) copper naphthenate, (E007) copper oxide, (E008) copper oxychloride, (E009) copper(2+) sulfate, (E010) dithianon, (E011) dodine, (E012) folpet, (E013) mancozeb, (E014) maneb, (E015) metiram, (E016) metiram zinc, (E017) oxine-copper, (E018) propineb, (E019) sulfur and sulfur preparations including calcium polysulfide, (E020) thiram, (E021) zineb, (E022) ziram, (E023) 6-ethyl-5,7-dioxo-6,7-dihydro-5
  • (F) Compounds capable to induce a host defence for example (F001) acibenzolar-S-methyl, (F002) isotianil, (F003) probenazole, (F004) tiadinil;
  • (G) Inhibitors of the amino acid and/or protein biosynthesis for example (G001) cyprodinil, (G002) kasugamycin, (G003) kasugamycin hydrochloride hydrate, (G004) oxytetracycline, (G005) pyrimethanil, (G006) 3 -(5 -fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline;
  • Inhibitors of the cell wall synthesis for example (1001) benthiavalicarb, (1002) dimethomorph, (1003) flumorph, (1004) iprovalicarb, (1005) mandipropamid, (1006) pyrimorph, (1007) valifenalate, (1008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en-l-one, (1009) (2Z)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one;
  • (J) Inhibitors of the lipid and membrane synthesis for example (J001) propamocarb, (J002) propamocarb hydrochloride, (J003) tolclofos-methyl;
  • K Inhibitors of the melanin biosynthesis, for example (K001) tricyclazole, (K002) 2,2,2- trifluoroethyl ⁇ 3-methyl- 1 -[(4-methylbenzoyl )amino]butan-2-yl [carbamate;
  • (L) Inhibitors of the nucleic acid synthesis for example (L001) benalaxyl, (L002) benalaxyl-M (kiralaxyl), (L003) metalaxyl, (L004) metalaxyl-M (mefenoxam);
  • (M) Inhibitors of the signal transduction for example (M001) fludioxonil, (M002) iprodione, (M003) procymidone, (M004) proquinazid, (M005) quinoxyfen, (M006) vinclozolin;
  • (O) Further compounds for example (O001) Abscisic acid, (0002) benthiazole, (0003) bethoxazin, (0004) capsimycin, (0005) carvone, (0006) chinomethionat, (0007) cufraneb, (0008) cyflufenamid, (0009) cymoxanil, (O010) cyprosulfamide, (O011) flutianil, (0012) fosetyl-aluminium, (0013) fosetyl- calcium, (0014) fosetyl-sodium, (0015) methyl isothiocyanate, (0016) metrafenone, (0017) mildiomycin, (0018) natamycin, (0019) nickel dimethyldithiocarbamate, (0020) nitrothal-isopropyl, (0021) oxamocarb, (0022) Oxathiapiprolin, (0023) oxyfenthiin, (0024) pentach
  • P Inhibitors of histone deacetylase for example (P001) N-(l-ethylcyclopropyl)-4-[5- (trifhioromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P002) N-(2-isopropylcyclopropyl)-4-[5- (triiluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P003) N-(2-methylcyclopropyl)-4-[5-
  • All named mixing partners of the classes (A) to (P) can, if their functional groups enable this, optionally form salts with suitable bases or acids.
  • Further compounds capable to act as a safener for example compounds of the group of heterocyclic carboxylic acid derivatives such as for example compounds of the type of dichlorophenylpyrazoline-3- carboxylic acid, preferably compounds such as (Q001) l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2-pyrazoline-3-carboxylic acid, (Q002) ethyl l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2-pyrazoline-3-carboxylate (“mefenpyr (-diethyl)”), and related compounds, as described in WO199107874.
  • compounds of the group of heterocyclic carboxylic acid derivatives such as for example compounds of the type of dichlorophenylpyrazoline-3- carboxylic acid, preferably compounds such as (Q001) l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5
  • composition of compound (I) according to the invention comprises at least one further active compound (2) selected from:
  • Inhibitors of the ergosterol biosynthesis for example, (A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A004) fenhexamid, (A005) fenpropidin, (A006) fenpropimorph, (A007) fenpyrazamine, (A008) fluquinconazole, (A009) flutriafol, (A010) imazalil, (A011) imazalil sulfate, (A012) ipconazole, (A013) metconazole, (A014) myclobutanil, (A015) paclobutrazol, (A016) prochloraz, (A017) propiconazole, (A018) prothioconazole, (A019) Pyrisoxazole, (A020) spiroxamine, (A021) tebuconazole, (A022)
  • (B) Inhibitors of the respiratory chain at complex I or II for example, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B004) carboxin, (B005) fluopyram, (B006) flutolanil, (B007) fluxapyroxad, (B008) furametpyr, (B009) Isofetamid, (B010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B014) isopyrazam (syn-e
  • (C) Inhibitors of the respiratory chain at complex III for example, (COOl) ametoctradin, (C002) amisulbrom, (C003) azoxystrobin, (C004) coumethoxystrobin, (C005) coumoxystrobin, (C006) cyazofamid, (C007) dimoxystrobin, (C008) enoxastrobin, (C009) famoxadone, (COIO) fenamidone, (C011) flufenoxystrobin, (C012) fluoxastrobin, (C013) kresoxim-methyl, (C014) metominostrobin, (C015) orysastrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C018) pyrametostrobin, (C019) pyraoxystrobin, (C020) trifloxystrobin, (C021) (2E)-2- ⁇ 2-[( ⁇ [(
  • (E) Compounds capable to have a multisite action for example (E001) bordeaux mixture, (E002) captafol, (E003) captan, (E004) chlorothalonil, (E005) copper hydroxide, (E006) copper naphthenate, (E007) copper oxide, (E008) copper oxychloride, (E009) copper(2+) sulfate, (E010) dithianon, (E011) dodine, (E012) folpet, (E013) mancozeb, (E014) maneb, (E015) metiram, (E016) metiram zinc, (E017) oxine-copper, (E018) propineb, (E019) sulfur and sulfur preparations including calcium polysulfide, (E020) thiram, (E021) zineb, (E022) ziram, (E023) 6-ethyl-5,7-dioxo-6,7-dihydro-5
  • P Inhibitors of histone deacetylase for example (P001) N-(l-ethylcyclopropyl)-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P002) N-(2-isopropylcyclopropyl)-4-[5-
  • compositions of compound (I) according to the invention comprise (2) at least one further active compound selected from:
  • compositions of compound (I) according to the invention comprise componenet (2) at least one further active compound selected from:
  • componenet (1) compound of formula (I), a group represented by the expression "(I)” comprising of compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, I- 11 , 1-12, 1-13, 1-14 and 1-15
  • component (2) selected from the groups A) to P) as defined herein (component 2, for example, (A001 or cyproconazole, in combination [(I)+(A001] )
  • the weight ratio of componenet (1) to component (2) is between 100:1 and 1:100 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • the weight ratio of componenet (1) to component (2) is between 50:1 and 1:50 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • the weight ratio of componenet (1) to component (2) is between 20:1 and 1:20 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • the weight ratio of componenet (1) to component (2) is between 5:1 and 1:5 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • the weight ratio of componenet (1) to component (2) is between 3:1 and 1:3 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • the weight ratio of componenet (1) to component (2) is 1:1 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
  • Combination [(1-2) + (A001] to [(1-2) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-2).
  • Combination [(1-3) + (A001] to [(1-3) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-3).
  • Combination [(1-4) + (A001] to [(1-4) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-4).
  • Combination [(1-5) + (A001] to [(1-5) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-5).
  • Combination [(1-6) + (A001] to [(1-6) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-6).
  • Combination [(1-7) + (A001] to [(1-7) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-7).
  • Combination [(1-9) + (A001] to [(1-9) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-9).
  • Combination [(TIO) + (A001] to [(1-10) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-10).
  • Combination [(Til) + (A001] to [(Til) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-11).
  • Combination [(1-12) + (A001] to [(T12) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T12).
  • Combination [(T13) + (A001] to [(T13) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T13).
  • Combination [(1-14) + (A001] to [(1-14) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-14).
  • Combination [(T15) + (A001] to [(T15) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T15).
  • the present invention provides use of the fungicidal composition for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi.
  • compositions disclosed in table- 1 to table- 16 and in particular when the weight ratios of componenet (1) to componenet (2) are as disclosed for these mixtures as herein mentioned before are used against crop phytopathogenic fungi like Alternaria species, for example Alternaria solanr, Erysiphe spp. (e.g. Erysiphe cichoracearum ); Pyricularia species, for example Pyricularia oryzae Septoria species, for example Septoria nodorum, Puccinia spp. (rusts) on various plants, in particular P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P.
  • Alternaria species for example Alternaria solanr, Erysiphe spp. (e.g. Erysiphe cichoracearum ); Pyricularia species, for example Pyricularia oryzae Septoria species, for example Septoria nodorum, Puccinia
  • hordei dwarf rust
  • P. graminis seed or black rust
  • P. recondita brown or leaf rust
  • wheat, barley or rye P. coronata (crown rust of grasses including oats) on cereals, such as e. g. wheat, barley or rye, and Puccinia sorghi (common rust) on maize, Puccinia polysora (southern rust) on maize, and P.
  • helianthi unsunflower rust
  • Puccinia melanocephala 'Brown rust' in sugarcane
  • Hemileia vastatrix and Hemileia cojfeicola leaf rust and grey rust of coffee
  • Hemileia vastatrix Coffee rust
  • Uromyces spp. on various crops
  • Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • novel agrochemical compositions according to the invention have a potent microbicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases). More specifically, the agrochemical composition according to the invention can be used to protect seeds, germinating plants, emerged seedlings, plants, plant parts, fruits and the soil in which the plants grow from unwanted microorganisms.
  • Control encompasses curative and protective treatment of unwanted microorganisms.
  • the unwanted microorganisms may be pathogenic bacteria or pathogenic fungi, more specifically phytopathogenic bacteria or phytopathogenic fungi. As detailed herein below, these phytopathogenic microorganims are the causal agents of a broad spectrum of plants diseases.
  • novel agrochemical composition according to the invention can be used as fungicides.
  • they can be useful in crop protection, for example for the control of unwanted fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • novel agrochemical composition according to the invention can also be used as bactericide.
  • they can be used in crop protection, for example for the control of unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae , Corynebacteriaceae and Streptomycetaceae .
  • the present invention provides a method for controlling or preventing infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein the fungicidal composition is applied to the plants, to parts thereof or to a locus thereof.
  • the present invention provides a method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with the fungicidal composition as described herein.
  • the present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, comprising the step of applying at least one novel agrochemical composition according to the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
  • novel agrochemical composition according to the invention when used in curative or protective methods for controlling phytopathogenic fungi, an effective and non-phytotoxic amount thereof is applied to the plants, plant parts, fruits, seeds or to the soil in which the plants grow.
  • Effective and non-phytotoxic amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the respective composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.
  • novel agrochemical composition according to the invention can be applied to any plants or plant parts.
  • the present invention provides a fungicidal composition for treating seed, seed of transgenic plants and transgenic plants.
  • Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders' rights.
  • GMO Genetically modified plants
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome. This gene gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression teclmology, RNA interference - RNAi - technology or microRNA - miRNA - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • Plant cultivars are understood to mean plants which have new properties ("traits”) and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • Plants which can be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Ivloraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Afusaceae sp.
  • Rosaceae sp. for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries
  • Rosaceae sp. for example pome fruits such as apples and
  • Rubiaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Alliaceae sp. for example leek, onion
  • peas for example peas
  • major crop plants such as Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and tiiticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
  • Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis ; Podosphaera species, for example Podosphaera leucotricha Sphaerotheca species, for example Sphaerotheca fuliginea Uncinula species, for example Uncinula necator Erysiphe species, for example Erysiphe cichoracearu diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae Hemileia species, for example Hemileia vastatrix Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae ; Puccinia species, for example Puccinia recondita, Puccinia graminis or Puccinia st
  • Cronartium ribicola White pine blister rust
  • Gymnosporangium juniperi-virginianae Cedar-apple rust
  • Hemileia vastatrix Coffee rust
  • Phakopsora meibomiae and P. pachyrhizi Soybean rust
  • Puccinia coronata Crown Rust of Oats and Ryegrass
  • Puccinia graminis Stetem rust of wheat and Kentucky bluegrass, or black rust of cereals
  • Puccinia hemerocallidis Daylily rust
  • Puccinia persistens subsp.
  • Puccinia sorghi rust in corn
  • Puccinia striiformis 'Yellow rust' in cereals
  • Puccinia melanocephala Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust); Puccinia melanocephala ('Brown rust' in sugarcane); Puccinia kuehnii ('Orange rust' in sugarcane).
  • diseases caused by pathogens from the group of the Oomycetes for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P.
  • brassicae Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium;
  • Aspergillus species for example Aspergillus flavus Cladosporium species, for example Cladosporium cladosporioides Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botry
  • Pseudomonas species for example Pseudomonas syringae pv. lachrymans
  • Erwinia species for example Erwinia amylovoran
  • Ralstonia species for example Ralstonia solanacearumn
  • Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp.
  • Rosaceae sp for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp.
  • Theaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Vitaceae sp. for example grapes
  • Solanaceae sp. for example tomatoes, peppers
  • Liliaceae sp. for example lettuce
  • Umbelliferae sp. for example Cruciferae sp., Chenopodiaceae sp.
  • Cucurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • peas for example peas
  • major crop plants such as Poaceae/Gramineae sp.
  • Poaceae/Gramineae sp. for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress
  • Fabacae sp. for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • the agrochemical compositions of the present invention can be used for curative or protective/preventive control of phytopathogenic fungi.
  • the present invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the novel agrochemical compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
  • novel agrochemical compositions according to the invention are well tolerated by plants at the concentrations required for controlling plant diseases allows the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • plants and plant parts can be treated.
  • plants are meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights).
  • Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods.
  • plant parts are meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, conns and rhizomes are listed.
  • Crops and vegetative and generative propagating material for example cuttings, conns, rhizomes, runners and seeds also belong to plant parts.
  • novel agrochemical compositions according to the invention when they are well tolerated by plants, have favorable homeotherm toxicity and are well tolerated by the environment, are suitable for protecting plants and plant organs, for enhancing harvest yields, for improving the quality of the harvested material. They can preferably be used as crop protection compositions. They are active against normally sensitive and resistant species and against all or some stages of development.
  • Plants which can be treated in accordance with the invention include the following main crop plants: maize, soya bean, alfalfa, cotton, sunflower, Brassica oil seeds such as Brassica napus (e.g. canola, rapeseed), Brassica rapa, B.juncea (e.g. (field) mustard) and Brassica carinata, Arecaceae sp. (e.g. oilpalm, coconut), rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, nuts, grapes and vine and vaiious fruit and vegetables from various botanic taxa, e.g. Rosaceae sp. (e.g.
  • pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds, plums and peaches, and berry fruits such as strawberries, raspberries, red and black currant and gooseberry), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Aforaceae sp., Oleaceae sp. (e.g. olive tree), Actinidaceae sp., Lauraceae sp. (e.g. avocado, cinnamon, camphor), Afusaceae sp. (e.g.
  • Rubiaceae sp. e.g. coffee
  • Theaceae sp. e.g. tea
  • Sterculiceae sp. e.g. lemons, oranges, mandarins and grapefruit
  • Solanaceae sp. e.g. tomatoes, potatoes, peppers, capsicum, aubergines, tobacco
  • Liliaceae sp. Compositae sp.
  • Umbelliferae sp. e.g. carrots, parsley, celery and celeriac
  • Alliaceae sp. e.g. leeks and onions
  • Cruciferae sp. e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage
  • Leguminosae sp. e.g. peanuts, peas, lentils and beans - e.g. common beans and broad beans
  • Chenopodiaceae sp. e.g. Swiss chard, fodder beet, spinach, beetroot
  • Linaceae sp. e.g.
  • novel agrochemical compositions according to the invention are suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamentals, vegetables (e. g. A Candida ) and sunflowers (e. g. A tragopogonis); Alternaria spp.(Alternaria leaf spot) on vegetables, rape (A brassicola or brassi cae), 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.
  • Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma ) spp. (rot or wilt) on broad leaved trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C.
  • Botrytis cinerea teleomorph: Botryotinia fuckeliana: grey mold
  • fruits and berries e.g. strawberries
  • vegetables e.g. lettuce, carrots, celery and cabbages
  • rape flowers, vines, forestry plants
  • zeaemaydis rice, sugar beets (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) 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: Helmin thosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g. C. sativus, anamorph: B.
  • tomatoes e.g. C. fulvum: leaf mold
  • cereals e.g. C. herbarum (black ear) on wheat
  • Claviceps purpurea ergot
  • Cochliobolus anamorph: Helmin
  • sorokiniana and rice (e.g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypit), corn (e.g. C. gramini cola: Anthracnose stalk rot), fruits, potatoes (e.g. C. coccodes: black dot), vegetables like beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum or C. gloeosporioides); Corticium spp., e.g. C. C.
  • sasakii sheath blight
  • 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.
  • liriodendri Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e.g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, net blotch) and wheat (e.g. D. D.
  • tritici-repentis tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyn), soft fruits (E.
  • Fusarium) nivale pink snow mold
  • cereals e. g. wheat or barley
  • Microsphaera diffusa powdery mildew
  • Monilinia spp. e.g. M. laxa, M. fructicola and M. fructigena(b ⁇ oom 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
  • M.fijiensis black Sigatoka disease
  • Peronospora spp. downy mildew
  • cabbage e.g. P. brassicae
  • rape e.g. P. parasitica
  • onions e.g. P. destructor
  • tobacco e.g. P. tabacina
  • soybeans e.g. P. manshurica
  • Phakopsora pachyrhizi and P. meibomiae sinoybean rust
  • Phialophora spp. e.g. on vines e.g. P. tracheiphila and P.
  • soybeans e.g. P. gregata: stem rot; Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e.g.
  • soybeans e. g. P. megasperma, syn. P. sojae
  • potatoes and tomatoes e. g. P. infestans: late blight
  • broad leaved trees e.g. P. ramorum: sudden oak death
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew) on rosa ceous plants, hop, pome and soft fruits, e.g. P.
  • Puccinia spp. rusts on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P.
  • Pyrenophora anamorph: Drechslera
  • tritici-repentis tan spot
  • P. teres net blotch
  • Pyricularia spp. e.g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals
  • Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum ); Ramu/aria spp., e. g. R.
  • collo- cygni Roso- cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R.
  • deformans leaf curl disease
  • T. pruni plum pocket
  • plums Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incamata (grey snow mold) on barley or wheat; Urocystis spp., e.g. U.
  • occulta stem smut
  • Uromyces spp. rust
  • vegetables such as beans (e.g. U. appendiculatus, syn. U. phaseoft) and sugar beets (e.g. U. betae);
  • Ustilago spp. loose smut) on cereals (e. g. U. nuda and U. avaenae), com (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • the present invention is also directed to the use of the novel agrochemical composition according to the invention for the treatment of soybean diseases.
  • Cercospora kikuchii Cercospora sojina
  • Colletotrichum gloeosporoides dematium var. truncatum Corynespora casiicola; Diaporthe phaseolorum; Microsphaera diffusa; Peronospora manshurica;
  • Phakopsora species for example Phakopsora pachyrhizi and Phakopsora meibomiae ( soybean rust); Phytophthora megasperma; Phialophora gregata; Rhizoctonia solani; Sclerotinia sclerotiorum; Septoria spp. e.g. Septoria glycines, Thielaviopsis basicola.
  • the novel agrochemical composition of the invention can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F.
  • Penicillium spec. such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotlys spec and others.
  • novel agrochemical composition of the invention can also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • novel agrochemical composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • novel agrochemical composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timberr
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the agrochemical composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the agrochemical composition of the invention preferably acts against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae.
  • microorganisms of the following genera Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria
  • novel agrochemical composition of the invention can, at particular concentrations or application rates, also be used to improve plant properties, or as microbicides, for example as bactericides, viricides (including compositions against viroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).
  • microbicides for example as bactericides, viricides (including compositions against viroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).
  • novel agrochemical composition of the invention may intervene in physiological processes of plants and can therefore also be used as plant growth regulators.
  • Growth regulating effects comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kernels/ear, number of ears/m2 , number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyllotaxy, earlier maturation / earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fmit/vegetable size, sprouting resistance and reduced lodging.
  • Increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight as well as to improved product quality, comprising: improved processability relating to size distribution (kernel, fruit, etc.), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaption to cooking and frying; improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage/ shelf-life, firmness/ softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.; increased desired ingredients such as e.g.
  • protein content protein content, fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste, etc.; decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content etc.
  • novel agrochemical composition of the invention also exhibits a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
  • Plant-strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.
  • plant physiology effects comprise the following:
  • Abiotic stress tolerance comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.
  • Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria.
  • biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.
  • the invention further comprises a method for treating seed.
  • the invention further provides seed which has been treated by one of the methods described in the previous paragraph.
  • the inventive seeds are employed in methods for the protection of seed from unwanted microorganisms. In these methods, seed treated with at least one inventive agrochemical composition is used.
  • the novel agrochemical composition of the present invention is also suitable for treating seed.
  • a large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seed during storage or after sowing, and also during and after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even minor damage may result in the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using appropriate compositions.
  • the present invention provides a seed comprising the fungicidal composition.
  • the present invention therefore also relates to a method for protection of seed and germinating plants from attack by phytopathogenic fungi, by treating the seed with an inventive composition.
  • the invention likewise relates to the use of the inventive compositions for treatment of seed to protect the seed and the germinating plant from phytopathogenic fungi.
  • the invention further relates to seed which has been treated with an inventive composition for protection from phytopathogenic fungi.
  • One of the advantages of the present invention is that the particular systemic properties of the novel agrochemical composition not only protect the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • novel agrochemical composition can especially also be used with transgenic seed, in which case the plant growing from this seed is capable of expressing a protein which acts against pests.
  • the novel agrochemical compositions By virtue of the treatment of such seed with the novel agrochemical compositions, merely the expression of the protein, for example an insecticidal protein, can control certain pests.
  • a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests.
  • the novel agrochemical compositions are suitable for protecting seeds of any plant variety which is used in agriculture, in greenhouses, in forests or in horticulture and viticulture.
  • seeds of cereals such as wheat, barley, rye, triticale, sorghm/millet and oats
  • maize cotton, soyabean, rice, potato, sunflower, bean, coffee, beet (for example sugar beet and fodder beet), peanut, oilseed rape, poppy, olive, coconut, cocoa, sugar cane, tobacco, vegetables (such as tomato, cucumbers, onions and lettuce), turf and ornamentals (see also below).
  • the treatment of seeds of cereals such as wheat, barley, rye, triticale and oats
  • maize and rice is of particular significance.
  • the treatment of transgenic seed with the novel agrochemical composition is of particular significance.
  • This relates to the seed of plants containing at least one heterologous gene which enables the expression of a polypeptide or protein having insecticidal properties.
  • the heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • This heterologous gene preferably originates from Bacillus sp., in which case the gene product is effective against the European maize borer and/or the western maize rootworm.
  • the heterologous gene more preferably originates from Bacillus thuringiensis.
  • the novel agrochemical composition is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15 % by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.
  • the amount of the novel agrochemical composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This has to be borne in mind in particular in the case of active ingredients which can have phytotoxic effects at certain application rates.
  • the present invention further relates to a novel agrochemical composition, for controlling unwanted microorganisms.
  • the agrochemical compositions may be applied to the microorganisms and/or in their habitat.
  • the agrochemical composition typically comprises at least one active compounds combination and at least one agriculturally suitable auxiliary, e.g. carrier(s) and/or surfactant(s).
  • auxiliary e.g. carrier(s) and/or surfactant(s).
  • control of harmful microorganisms means a reduction in infestation by harmful microorganisms, compared with the untreated plant measured as fungicidal efficacy, preferably a reduction by 25-50 %, compared with the untreated plant (100 %), more preferably a reduction by 40-79 %, compared with the untreated plant (100 %); even more preferably, the infection by harmful microorganisms is entirely suppressed (by 70-100 %).
  • the control may be curative, i.e. for treatment of already infected plants, or protective, for protection of plants which have not yet been infected.
  • an "effective but non-phytotoxic amount” means an amount of the novel agrochemical composition which is sufficient to control the fungal disease of the plant in a satisfactory manner or to eradicate the fungal disease completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity.
  • this application rate may vary within a relatively wide range. It depends on several factors, for example on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions.
  • a carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert.
  • the carrier generally improves the application of the compounds, for instance, to plants, plants parts or seeds.
  • suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates.
  • Examples of typically useful solid earners forpreparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.
  • suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N- alkylpynolidones) and lactones, sulf
  • the carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • a liquefied gaseous extender i.e. liquid which is gaseous at standard temperature and under standard pressure
  • aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • the surfactant can be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s) and any mixtures thereof.
  • surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylmyl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulphates, sulphonates, phosphates (for example, alkylsulphonates, alkyl sulphates, arylsulphonates) and protein hydrolysates, lignosulphit
  • auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g.
  • dyes or pigments such as inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g. silicone antifoams and magnesium stearate), preservatives (e.g.
  • dichlorophene and benzyl alcohol hemiformal secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica), stickers, gibberellins and processing auxiliaries, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.
  • secondary thickeners cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica
  • stickers gibberellins and processing auxiliaries
  • mineral and vegetable oils perfumes
  • waxes including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc
  • protective colloids including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molyb
  • auxiliaries are related to the intended mode of application of the compound of formula (I) and/or on the physical properties. Furthermore, the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the compositions or use forms prepared therefrom. The choice of auxiliaries may allow customizing the compositions to specific needs.
  • the novel agrochemical composition of the present invention may be in any customary form, such as solutions (e.g aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the agrochemical composition, fertilizers and also microencapsulations in polymeric substances.
  • the agrochemical composition according to the invention may be present in a suspended, emulsified or dissolved form.
  • the novel agrochemical composition of the invention may be provided to the end user as ready-for-use formulation, i.e. the compositions can be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device.
  • the compositions may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.
  • novel agrochemical composition of the invention can be prepared in conventional manners, for example by mixing the agrochemical composition according to the invention with one or more suitable auxiliaries, such as disclosed herein above.
  • the novel agrochemical composition according to the invention contains generally from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 10 to 70 % by weight of the active compounds according to the invention.
  • the rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • a general guideline compounds may be applied at a rate of from 1 to 2000 L/ha, especially from 10 to 1000 L/ha.
  • novel agrochemical composition can be applied directly, i.e. without containing any other components and without having been diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 Al, WO 2002/080675, WO 2002/028186.
  • novel agrochemical composition usable in accordance with the invention can be converted to the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
  • formulations are prepared in a known manner, by mixing the active compounds with customary additives, for example customary extenders and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • customary additives for example customary extenders and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.
  • Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Preference is given to using alkyl naphthalenesulphonates, such as diisopropyl or diisobutyl naphthalenesulphonates .
  • Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
  • Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
  • Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.
  • Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions.
  • Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products.
  • Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • the seed dressing formulations usable in accordance with the invention can be used, either directly or after previously having been diluted with water, for the treatment of a wide range of different seed, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.
  • the procedure in the seed dressing is to place the seed into a mixer, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying process.
  • the components (1) and components (2) are advantageously present in a synergistically effective weight ratio of components (l):components (2) in a range of 100:1 to 1:100, preferably in a weight ratio of 50:1 to 1:50, more preferably in a weight ratio of 20:1 to 1:20, even more preferably in a weight ratio of 10:1 to 1:10.
  • novel agrochemical composition is used for foliar application.
  • composition stands for the various mixtures or combinations of components (1) and (2), for example in a single “ready -mix” form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a "tank- mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • the order of applying the components (1) and (2) is not essential for working the present invention.
  • agrochemical composition means a combination or mixture of at least two active compounds with further agriculturally suitable additives, such as agriculturally suitable auxiliaries, e.g. solvents, carriers, surfactants, extenders or the like which are described above.
  • auxiliaries e.g. solvents, carriers, surfactants, extenders or the like which are described above.
  • agrochemical composition also comprises the terms "crop protection composition” and "formulation”.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the user may apply the novel agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable agrochemical composition, the kit comprising a) a composition comprising component (1) as defined herein and at least one auxiliary; and b) a composition comprising component (2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component (3) as defined herein.
  • the present invention furthermore relates to a agrochemical compositions comprising a mixture of at least one compound of formula (I) (component 1) and at least one further active compound useful for plant protection, e. g. selected from the groups A) to P) (component 2) as described above, and if desired one suitable solvent or solid carrier.
  • component 1 at least one compound of formula (I)
  • component 2 at least one further active compound useful for plant protection, e. g. selected from the groups A) to P) (component 2) as described above, and if desired one suitable solvent or solid carrier.
  • combating harmful fungi with a mixture of a compound of formula (I) and at least one fungicide from groups A) to P), as described above, is more efficient than combating those fungi with the individual compounds of formula (I) or individual fungicides from groups A) to P).
  • a synergistic effect can be obtained, i.e. more than simple addition of the individual effects is obtained (synergistic mixtures).
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the compound of formula (I) [component (1)] and the component (2) generally depends from the properties of the active components used, usually it is in the range of 1:10 000 to 10 000:1 , often it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1 , preferably in the range of 1:20 to 20:1 , more preferably in the range of 1 :5 to 5 : 1 and in particular in the range of 1 :2 to 2: 1.
  • the weight ratio of the compound of formula (I) [component (1)] and the component (2) usually is in the range of 1000:1 to 1:1, often in the range of 100:1 to 1:1, regularly in the range of 50:1 to 1:1, preferably in the range of 20:1 to 1:1, more preferably in the range of 5 : 1 to 1 : 1 and in particular in the range of 2:1 to 1:1.
  • the weight ratio of the compound of formula (I) [component (1)] and the component (2) usually is in the range of 1:1 to 1:1000, often in the range of 1:1 to 1:100, regularly in the range of 1:1 to 1:50, preferably in the range of 1:1 to 1:20, more preferably in the range of 1:1 to 1 :5 and in particular in the range of 1:1 to 1:2.
  • the ternary mixtures i.e.
  • compositions according to the invention comprising the compound of formula (I) [component (1)] and component (2) and a compound of formula (III) [component (3)],
  • the weight ratio of compound of formula (I) [component (1)] and component (2) is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:5 to 5:1 and in particular in the range of 1:2 to 2:1
  • the weight ratio of component (1) and component (3) is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:5 to 5:1 and in particular in the range of 1:2 to 2:1.
  • the ternary mixtures comprise as compounds III fungicidal compounds that are independently of each other selected from the groups A), B), C), D), E), F), G), H), I), J), K) L), M), N), O) and P); and wherein the at least one active compound III of component (3) is not identical with the at least one active compound II of component (2).
  • any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the compound of formula (I) [component (1)].
  • the method of treatment according to the invention also provides the use or application of component (1) and component (2) in a simultaneous, separate or sequential manner. If the single active ingredient is applied in a sequential manner, i.e. at different times, they are applied one after the other within a reasonable period, such as a few hours or days. Preferably the order of applying the component (1) and component (2) is not essential for working the present invention.
  • the component (1) and (2) are advantageously present in a synergistically effective weight ratio of (1):(2) in a range of 100:1 to 1:100, preferably in a weight ratio of 50:1 to 1:50, more preferably in a weight ratio of 20:1 to 1:20, even more preferably in a weight ratio of 10:1 to 1:10, 5:1 to 1:5 and 2:1 to 1:2.
  • Preferred formulations of agrochemical composition as disclosed in the present invention can have the following compositions (weight %): a. Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Dusts active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Suspension concentrates active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Wettable powders active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %
  • the combination is mixed and ground with the adjuvants and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1).
  • This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved.
  • a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added.
  • the mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • composition comprising the compound of formula (I) [component (1)] and the component (2) may show a synergistic effect.
  • An efficacy of 0 means that the infection level of the treated plants is corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
  • the expected efficacies of active compound combinations may be determined using Colby's formulas (COLBY, S.R. "Calculating synergistic and antagonistic responses of herbicide combination", Weeds, Vol. 15, pages 20-22; 1967).
  • E represents the expected percentage of inhibition of the disease for the combination of two fungicides at defined doses (for example equal to x and y respectively)
  • x is the percentage of inhibition observed for the disease by the compound (1) at a given dose (equal to x)
  • y is the percentage of inhibition observed for the disease by the compound (2) at a defined dose (equal to y).
  • X efficacy, expressed in % of the untreated control, when using the active compound (1) at the concentration a
  • Y efficacy, expressed in % of the untreated control, when using the active compound (2) at the concentration b
  • the compound of formula (I) can be synthesized by treating compound of formula 3 with trimethylortoformate and -tohienesiilfonic acid followed by the reaction with different secondary amines (HNR'R 2 ) as mentioned in US20110130282.
  • the compound 1 is an important intermediate for the synthesis of compound of formula (I). There are various methods described in the literature to synthesis compound formula 1 such as
  • Method 1 From corresponding benzoyl chloride using catalyst zinc chloride (ZnCl ⁇ ) or aluminum chloride (AICR) in the presence of dichloromethane as described in Helvitachimica Act XXIX (1946), page No 1413-1424, and Tetrahedron, 2000, 56, page no 7199-7203.
  • ZnCl ⁇ catalyst zinc chloride
  • AICR aluminum chloride
  • Method 2 From corresponding benzoic acid in the presence of acid catalyst such as (a) trifluoromethane sulphonic acid as described in Tetrahedron, 2000, 56, pages 7199-7203; (b) Graphite and methane sulphonic acid as described in Synthesis, 2004, 13, page no 2165-2168; (c) Graphite and -toluene sulphonic acid as described in Helvetiva Chimica act, 2005, 88, page no 2282-2287; (d) 1- perfluorobutanesulphonic acid as described in Synthesis, 2000, 10, page no 1427-1430.
  • acid catalyst such as (a) trifluoromethane sulphonic acid as described in Tetrahedron, 2000, 56, pages 7199-7203; (b) Graphite and methane sulphonic acid as described in Synthesis, 2004, 13, page no 2165-2168; (c) Graphite and -toluene sulphonic acid as described in Helvetiva Chimica act
  • Method 3 From corresponding derivative of benzoic acid in the presence of metal triflates such as copper triflate, gallium triflate or antimonium triflate or ytterbium triflate or scandium triflate or bismuth triflate as described in Green chemistry, 4 (2002), page no 129-133 or in Tetrahedron, 56 (2000), page no 6 63- 6465 or Bull chemical society of Jpn, 2000, 73, page no 2325-2333.
  • metal triflates such as copper triflate, gallium triflate or antimonium triflate or ytterbium triflate or scandium triflate or bismuth triflate as described in Green chemistry, 4 (2002), page no 129-133 or in Tetrahedron, 56 (2000), page no 6 63- 6465 or Bull chemical society of Jpn, 2000, 73, page no 2325-2333.
  • Method 4 From corresponding substituted benzoic acid in the presence of phosphorus pentoxide (P2O5) as such or adsorbed on silica gel as described in Tetrahedron letters, 2008, 49, page no 6715-6719.
  • P2O5 phosphorus pentoxide
  • the compound of formula (I) can be synthesized using suitably substituted compound of formula 2a and following the same methods as described in scheme 1.
  • the corresponding intermediate 2a can be synthesized from phenyl acetonitrile in the presence of bases like sodium hydroxide, or sodium tert- butoxide, or sodium hydride followed by oxidation with hydrogen peroxide/m-chloroperbenzoic acid (Fh0 2 /mCPBA) in the presence of aqueous potassium hydroxide (KOH) as described in (/. Org. Chem., 1983, 48, 4097-98, /. Org. Chem. 1983, 48, 4087-4096).
  • bases like sodium hydroxide, or sodium tert- butoxide, or sodium hydride followed by oxidation with hydrogen peroxide/m-chloroperbenzoic acid (Fh0 2 /mCPBA) in the presence of aqueous potassium hydroxide (KOH) as described in (/. Org. Chem.
  • the compound of formula (I) can also be synthesised using a suzuki reaction by treating compound of formula 6 with the corresponding substituted benzyl halide as mentioned in Bioorganic & Medicinal
  • the compounds of formula 6 can be synthesised by treating the bromo derivative 5 with bis(pincolato)diboran using palladium acetate and [1,1'- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride [PdChCdppf)] dichloromethane complex in dioxane with good yield.
  • reaction mixture was concentrated under reduced pressure to obtain the residue, which was then purified by column chromatography on silica gel using hexane: ethyl acetate as eluent to obtain the desired N'- (2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (7 g, 23.77 mmol, 77 % yield).
  • the compounds of formula (I) show fungicidal activities which are exerted with respect to numerous fungi which attack on important agricultural crops.
  • the compounds of the present invention were assessed for their activity as described in the following tests:
  • the compounds were further selected for in vivo (Greenhouse) preventive/curative testing.
  • the methods followed to check the preventive/curative efficacy of compounds on the pathogens were as following:
  • Example A Pyricularia oryzae test in Rice
  • the single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL.
  • the test solutions were poured into spray bottles for further applications.
  • a visual assessment of the performance of the compounds or compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compounds and mixtures were calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
  • Table-A The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly compound (1-2), compound (1-6) and compound (1-7) as component (1) and other components (2) against Pyricularia oryzae in Rice are shown in the table below:
  • the single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL.
  • the test solutions were poured into spray bottles for further applications.
  • a visual assessment of the performance of the compounds or compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compounds and mixtures was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
  • Table-B The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Alternaria solani in Tomato are shown in the table below:
  • Example C Erysiphe cichoracearum test in Cucumber
  • the single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL.
  • the test solutions were poured into spray bottles for further applications.
  • a visual assessment of the performance of the compounds and the respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
  • Table-C The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Erysiphe cichoracearum in Cucumber are shown in the table below:
  • the single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 50 ml.
  • the test solutions were poured into spray bottles for further applications.
  • a visual assessment of the performance of the compounds and respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
  • Table-D The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Phakopsora pachyrhizi in Soybean are shown in the table below.
  • Example E Pamstagonospora nodorum/ Septoria nodorum/ Stagnospora nodorum test in Wheat
  • the single compounds or compound combinations were dissolved in 2% DMSO/ Acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL.
  • the spray solutions were poured into spray bottles for further applications.
  • a visual assessment of the performance of the compounds and compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7 and 10 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis & stunting
  • Table-E The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Parastagonospora nodorum/ Septoria nodorum/ Stagnospora nodorum in Wheat are shown in the table below:

Abstract

The present invention discloses a novel agrochemical composition comprising (1) at lease one compound of formula (I) wherein, R1, R2, R3, R4, R5, R6, R7 and m are as defined in the detailed description and (2) at least one further active ingredient. The present invention further discloses a method for controlling the phytopathogenic fungi of plants using the agrochemical composition according to invention.

Description

TITLE OF THE INVENTION: NOVEL AGROCHEMICAL COMPOSITION COMPRISING 4- SUBSTITUTED PHENYLAMIDINE COMPOUNDS
FIELD OF THE INVENTION:
The present invention relates to a novel agrochemical composition. More particularly, the present invention relates to a novel agrochemical composition which comprises a mixture of one or more phenylamidine compounds of formula (I) as a component (1) and one or more fungicidally active compounds as component (2). Further, the present invention relates to a method for controlling phytopathogenic fungi of plants, to the use of a novel agrochemical composition according to the invention for the treatment of one or more seeds, to a method for protecting one or more seeds and to the corresponding treated seeds.
BACKGROUND OF THE INVENTION:
The use of phenylamidine compounds as a fungicide was known from the following prior art documents: W02000046184, W02003093224, WO2017102635, WO2018069841, WO2018108998 and
W02018091430 disclose arylamidine derivatives as fungicides.
WO2018228896, W02015121802, W02007031507, W02005089547 and W02003024219 disclose the fungicide mixtures comprising at least one arylamidine derivative and a further selected known fungicide.
The combinations of fungicides are often used to facilitate disease control and to retard resistance development. It is desirable to enhance the activity spectrum and the efficacy of disease control by using mixtures of active ingredients that provide a combination of curative, systemic and preventative control of plant pathogens. Also desirable are combinations that provide greater residual efficvacy to allow for extended spray intervals. It is also very desirable to combine fungicidal agents that inhibit different biochemical pathways in the fungal pathogens to retard development of resistance to any one particular plant disease control agent.
Fungicides that effectively control plant pathogens with a reduced quantity of chemical agent released in the environment are always desirable. Also there is constant need to widen the spectrum of activity, reduce toxicity and lower application rates. The present invention provides agrochemical compositions which in some aspects at least achieve the stated objective.
Surprisingly, it has been found that the novel agrochemical compositions according to the invention not only bring about the additive enhancement of the spectrum of action with respect to the phytopathogens to be controlled, that was in principle to be expected, but also achieves a synergistic effect. The synergistic effect of the agrochemical compositions of the present invention helps to reduce the application rate of component (1) and component (2) by maintaining the level of efficacy even if the two individual compounds alone have become ineffective at such low application rates. Also it allows a substantial broadening of the spectrum of phytopathogens that can be controlled by, at the same time, increasing the safety in use.
In addition to the fungicidal and/or nematicidal and/or insecticidal synergistic activity, the agrochemical compositions according to the invention have further surprising properties which, in a wider sense, may also be called synergistic, such as, for example: broadening of the activity spectrum to other insects, nematodes and/or phytopathogens, for example to resistant strains of plant diseases; lower application rates of the active compounds; sufficient control of pests with the aid of the agrochemical composition according to the invention even at application rates where the individual compounds show virtually no activity; advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage stability and light stability; advantageous residue formation; improved toxicological or eco-biological behavior; improved properties of the so called effects on plant physiology, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, lower phytotoxicity, mobilization of the defense system of the plant, good plant compatibility.
Thus, the use of the novel agrochemical compositions according to the invention contribute considerably to keeping young cereal stands healthy, which increases, for example, the winter survival of the cereal seed treated, and also safeguards quality and yield.
Moreover, the novel agrochemical compositions according to the invention may contribute to enhanced systemic action. Even if the individual compounds of the combination do not have sufficient systemic properties, the novel agrochemical composition according to the invention may still have this property. In a similar manner, the novel agrochemical composition according to the invention may result in higher long lasting efficacy of the fungicidal and/or insecticidal and/or nematicidal action.
SUMMARY OF THE INVENTION:
Accordingly, the present invention provides a novel agrochemical composition comprising:
(1) at least one compound of formula (I)
Figure imgf000003_0001
Formula (I) wherein, R1 is selected from the group consisting of G-G-alkyl, C2-Ce-alkenyl, C3-C6-cycloalkyl-Ci-C3- alkyl and C3-C6-cycloalkyl;
R2 is independently selected from the group consisting of C2-Ce-alkyl, C2-Ce-alkenyl, C3 G- cycloalkyl-Ci-C3-alkyl and C3-C6-cycloalkyl;
R3 and R4 are independently selected from the group consisting of halogen, cyano, G-G-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy and C3-C6-cycloalkyl;
R5 and R6 are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C3-alkyl, Ci-C3-haloalkyl and Ci-C3-alkoxy; or
R5 and R6 together with the carbon atom to which they are attached may form a C=CR’R’, C=NR’ or cyclopropyl ring;
R’ is selected from the group consisting of hydrogen, Ci-C3-alkyl, C3-C6-cycloalkylalkyl and Ci- C3-alkoxy;
R7 is selected from the group consisting of hydrogen, halogen, cyano, G-G-alkyl, C 1 -G- haloalkyl, Ci-Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, C3-C8- cycloalkyl and C3-C6-cycloalkyl-Ci-C3-alkyl; m represent integers 0, 1, 2, 3 or 4; or salts, AG x ides, metal complexes or stereoisomers thereof; and
(2) at least one further active compound selected from the following groups:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(D) inhibitors of the mitosis and cell division,
(E) compounds capable of having a multisite action,
(F) compounds capable of inducing a host defense,
(G) inhibitors of the amino acid and/or protein biosynthesis,
(H) inhibitors of the ATP production,
(I) inhibitors of the cell wall synthesis,
(J) inhibitors of the lipid and membrane synthesis,
(K) inhibitors of the melanine biosynthesis,
(L) inhibitors of the nucleic acid synthesis, (M) inhibitors of the signal transduction,
(N) compounds capable of acting as uncoupler,
(O) other fungicides,
(P) HDAC inhibitors
(Q) compounds capable to act as a safener.
In one embodiment, the present invention provides a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, comprising the step of applying at least one novel agrochemical composition according to the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
DETAILED DESCRIPTION OF THE INVENTION:
DEFINITIONS:
In the definitions of the symbols given in the above formulae, collective terms were used which are generally representative of the following substituents:
Hydrogen: Preferably, the definition of hydrogen encompasses also isotopes of hydrogen, preferably deuterium and tritium, more preferably deuterium.
Halogen: (also in combinations such as haloalkyl, haloalkoxy etc.) fluorine, chlorine, bromine and iodine, and preferably fluorine, chlorine, bromine and more preferably fluorine, chlorine;
Alkyl: (including in combinations such as alkylthio, alkoxy etc.) saturated, straight-chain or branched hydrocarbyl radicals having 1 to 6 carbon atoms, for example Ci-Ce-alkyl, such as methyl, ethyl, propyl,
1 -methyl ethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,
2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl- 1-methylpropyl, l-ethyl-2- methylpropyl, heptyl and octyl. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl.
Haloalkyl: (including in combinations such as haloalkylthio, haloalkoxy etc.) straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above, for example Ci-C3-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1- bromoethyl, 1-lluoroethyl, 2-l uoroethyl, 2,2-dil uoroethyl, 2,2,2-trilluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2-difluoroethyl, 2,2-dichloro-2-lluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1- trifluoroprop-2-yl.
Halomethyl: a methyl group, where some or all of the hydrogen atoms in these group may be replaced by halogen atoms as specified above, for example (but not limited to) chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, and preferably trifluoromethyl.
The term "cycloalkyl" means alkyl closed to form a ring. Non-limiting examples include but are not limited to cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
The term "alkoxy" used either alone or in compound words included Ci-Ce alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1- ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1 ,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2- dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2- trimethylpropoxy, 1,2,2-trimethylpropoxy, 1 -ethyl- 1-methylpropoxy and l-ethyl-2-methylpropoxy and the different isomers.
Depending on the nature of the substituents, the compounds of formula (I) can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. If applicable, compounds of formula (I) comprise both the E and the Z isomers, and also the threo and erythro, and the optical isomers, any mixtures of these isomers, and the possible tautomeric forms.
Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.
Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the art.
Depending on the nature of the substituents, the compounds of formula (I) can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents of ring B. The invention thus relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions. The syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.
The compound of formula (I) carry amidine groups which induce basic properties. Thus, these compounds can be reacted with acids to give salts.
Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as NaHSCb and KHSO4.
Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms), arylsulfonic acids or - disulfonic acids (aromatic groups, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl groups having 1 to 20 carbon atoms), arylphosphonic acids or -diphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic acid groups), where the alkyl and aryl groups may carry further substituents, for example p-toluenesulfonic acid, salicylic acid, p- aminosalicylic acid, 2- phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
The radical definitions and explanations given above in general terms or stated within preferred ranges can, however, also be combined with one another as desired, i.e. including between the particular ranges and prefrred ranges. They apply both to the end products and correspondingly to precursors and intermediates. In addition, individual definitions may not apply.
In an embodiment, the present invention provides a novel agrochemical composition comprising mixture of component (1) and component (2), wherein component (1) is a at least one compound of formula (I)
Figure imgf000007_0001
Formula (I) wherein,
R1 is selected from the group consisting of Ci-CValkyk C2-Ce-alkenyl, C3-C6-cycloalkyl-Ci-C3-alkyl and C3 -Cr, -cycloalkyl ;
R2 is independently selected from the group consisting of C2-Ce-alkyl, C2-Ce-alkenyl, C3-C6-cycloalkyl- Ci-C3-alkyl and C3-C6-cycloalkyl;
R3 and R4 are independently selected from the group consisting of halogen, cyano, C CValkyk Ci-Ce- haloalkyl, Ci-Ce-alkoxy and C3-C6-cycloalkyl;
R5 and R6 are independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl and Ci-C3-alkoxy; or
R5 and R6 together with the carbon atom to which they are bound form a C=CR’R’, C=NR’ or cyclopropyl ring;
R’ is selected from the group consisting of hydrogen, Ci-C3-alkyl, C3-C6-cycloalkylalkyl and Ci- C3-alkoxy;
R7 is selected from the group consisting of hydrogen, halogen, cyano, C CValkyk CVCVhaloalkyk Ci- Ce-alkoxy, Ci-Ce-alkylthio, Ci-Ce-alkylsulfinyl, Ci-Ce-alkylsulfonyl, CVCVcycloalkyl and C3-C6- cycloalkyl-Ci-C3-alkyl; m represent integers 0, 1, 2, 3 or 4; or salts, N- oxides, metal complexes or stereoisomers thereof; and component (2) is a at least one further active compound selected from the following groups:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(D) inhibitors of the mitosis and cell division,
(E) compounds capable of having a multisite action,
(F) compounds capable of inducing a host defense,
(G) inhibitors of the amino acid and/or protein biosynthesis,
(H) inhibitors of the ATP production,
(I) inhibitors of the cell wall synthesis,
(J) inhibitors of the lipid and membrane synthesis, (K) inhibitors of the melanine biosynthesis,
(L) inhibitors of the nucleic acid synthesis,
(M) inhibitors of the signal transduction,
(N) compounds capable of acting as uncoupler,
(O) other fungicides,
(P) HD AC inhibitors
(Q) compounds capable to act as a safener.
In a preferred embodiment, the component (1) is a at least one compound of formula (I)
Figure imgf000009_0001
wherein,
R1 is selected from the group consisting of methyl, ethyl, isopropyl and cyclopropyl;
R2 is selected from the group consisting of ethyl, isopropyl, cyclopropyl and cyclopropylmethyl;
R3 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl and cyclopropyl;
R4 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy and cyclopropyl;
R5 and R6 are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, halomethyl and methoxy;
R5 and R6 together with the carbon atom to which they are bound form a cyclopropyl ring or represents C=N-Ci-C3-alkyl;
R7 is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy and cyclopropyl; m represent integers 0, 1, 2, 3 or 4; or salts, N- oxides, metal complexes or stereoisomers thereof; and component (2) is a at least one further active compound selected from the following groups: (A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(D) inhibitors of the mitosis and cell division,
(E) compounds capable of having a multisite action,
(F) compounds capable of inducing a host defense,
(G) inhibitors of the amino acid and/or protein biosynthesis,
(H) inhibitors of the ATP production,
(I) inhibitors of the cell wall synthesis,
(J) inhibitors of the lipid and membrane synthesis,
(K) inhibitors of the melanine biosynthesis,
(L) inhibitors of the nucleic acid synthesis,
(M) inhibitors of the signal transduction,
(N) compounds capable of acting as uncoupler,
(O) other fungicides,
(P) HD AC inhibitors
(Q) compounds capable to act as a safener.
In preferred embodiment, the compound of formula (I) is
(1-1) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;
(1-2) N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;
(1-3) N-ethyl-N'-(5-methoxy -2 -methyl -4-(2-methylbenzyl)phenyl)-N-methylformimidamide;
(1-4) N'-(4-((2-bromophenyl)(methoxy)methyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
(1-5) N'-(5-chloro-4-((4-chloro-3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N- methy lformi midamide ;
(1-6) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
(1-7) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
(1-8) N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;
(T9) N'-(4-(3,5-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
(I- 10) N'-(2-chloro-4-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;
(I- 11) N'-(2-chloro-4-((2-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N- methylformi midamide.
(1-12) N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;
(1-13) N'-(5-chloro-4-(3-chloro-2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;
(1-14) N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide and
(1-15) N'-(2-chloro-4-(3-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide.
In one embodiment, the component (2) is a at least one further active compound selected from the following groups:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(E) compounds capable of having a multisite action,
(L) inhibitors of the nucleic acid synthesis,
(M)inhibitors of the signal transduction,
(N) compounds capable of acting as uncoupler,
(O) other fungicides,
(P) HDAC inhibitors
(Q) compounds capable to act as a safener.
In preferred embodiment, the component (2) is at least one further active compound selected from the following groups:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(E) compounds capable of having a multisite action,
(P) HDAC inhibitors
(Q) compounds capable to act as a safener.
Even more preferred, the component (2) is at least one further active compound selected from the following groups:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(E) compounds capable of having a multisite action (P) HD AC inhibitors.
Preferred novel agrochemical composition according to the invention comprises at least one further active compound (2) selected from:
(A) Inhibitors of the ergosterol biosynthesis, for example, (A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A004) fenhexamid, (A005) fenpropidin, (A006) fenpropimorph, (A007) fenpyrazamine, (A008) fluquinconazole, (A009) flutriafol, (A010) imazalil, (A011) imazalil sulfate, (A012) ipconazole, (A013) metconazole, (A014) myclobutanil, (A015) paclobutrazol, (A016) prochloraz, (A017) propiconazole, (A018) prothioconazole, (A019) Pyrisoxazole, (A020) spiroxamine, (A021) tebuconazole, (A022) tetraconazole, (A023) triadimenol, (A024) tridemorph, (A025) triticonazole, (A026) (lR,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol- l-ylmethyl)cyclopentanol, (A027) (lS,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-
1.2.4-triazol-l-ylmethyl)cyclopentanol, (A028) (2R)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2- dichlorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (A029) (2R)-2-(l-chlorocyclopropyl)-4-[(lS)-2,2- dichlorocyclopropyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A030) (2R)-2- [4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A031) (2S)-2-(l-chlorocyclopropyl)-4- [( lR)-2,2-dichlorocyclopropyl] - 1 -( lH-l,2,4-triazol- 1 -yl)butan-2-ol, (A032) (2S)-2-( 1 - chlorocyclopropyl)-4-[(l S)-2,2-dichlorocyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A033) (2S)-2- [4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A034) (R)-[3-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (A035) (S)-[3-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (A036) [3- (4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- 1 ,2-oxazol-4-yl](pyridin-3-yl)methanol, (A037) 1 -
( { (2R,4S)-2- [2-chloro-4-(4-chlorophenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2-yl } methyl)- 1H- 1 ,2,4- triazole, (A038) l-({ (2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2- yl}methyl)-lH- 1,2, 4-triazole, (A039) l-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A040) l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A041) l-{ [rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol-5-yl thiocyanate, (A042) 2-
[(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3-thione, (A043) 2-[(2R,4R,5S)- 1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-
2.4-dihydro-3H-l,2,4-triazole-3-thione, (A044) 2-[(2R,4S,5R)- l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A045) 2-[(2R,4S,5S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A046)
2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A047) 2- [(2S ,4R,5 S)- 1 -(2,4-dichlorophenyl)-5 -hydroxy-2, 6, 6-trimethylheptan-4-yl] - 2,4-dihydro-3H-l,2,4-triazole-3-thione, (A048) 2-[(2S,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3 -thione, (A049) 2- [(2S ,4S ,5 S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A050) 2- [l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A052) 2-[2- chloro-4-(4-chlorophenoxy)phenyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A053) 2- [4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A054) 2- [4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l -yl)pentan-2-ol, (A055) 2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A056) 2-{[3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A057) 2-{[rel(2R,3R)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l ,2,4- triazole-3 -thione, (A059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (A060) 5-(allylsulfanyl)-l-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yljmethyl } - 1 H- 1 ,2,4-triazole, (A061) 5 -(allylsulfanyl)- 1 - { [rel(2R,3R)-3-2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l, 2, 4-triazole, (A062) 5-(allylsulfanyl)-l-{[rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH- 1,2, 4-triazole, (A063) N'-(2,5-dimethyl-4- {[3-(l,l,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (A064) N'- (2, 5 -dimethyl-4- { [3-(2, 2, 2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (A065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamide,(A066) N'-(2,5-dimethyl-4-{[3-(pentalluoroethoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidofonnamide, (A067) N'-(2, 5-dimethyl-4-{ 3-[(l, 1,2,2- tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (A068) N'-(2,5-dimethyl- 4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (A069) N'-(2,5- dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidofonnamide, (A070) N'-(2,5- dimethyl-4-{3-[(pentalluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamide, (A071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoiormamide, (A072) N'-(4-{ [3-(dilluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N- methylimidoformamide, (A073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N- ethyl-N-methylimidofonnamide, (A074) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2-yloxy)-2- methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (A075) N'-{ 4-[(4,5-dichloro-l ,3-thiazol-2- yl)oxy] -2,5-dimethylphenyl } -N-ethyl-N-methylimidoformamide, (A076) N'- { 5-bromo-6- [(1 R)- 1 -(3 ,5 - difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofonnamide, (A077) N'-{5- bromo-6- [( lS)-l-(3,5 -difluorophenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamide, (A078) N'- { 5 -bromo-6- [(cis-4-isopropylcyclohexyl)oxy ] -2-methylpyridin-3 -yl } -N-ethyl-N- methylimidofornamide, (A079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3- yl } -N-ethyl-N-methylimidoformamide, (A080) N'- { 5 -bromo-6- [ 1 -(3 ,5-difluorophenyl)ethoxy ] -2- methy lpyri din-3 -yl} -N-ethyl-N-methylimidoformamide, (A081) Mefentrifhiconazole, (A082)
Ipfentrifluconazole, (A083) l-(2,4-difluorophenyl)-2-(lH-l,2,4-triazol-l-yl)-l-[l-(2,6-difhioro-4- chlorophenoxy)cyclopropyl] ethanol, (A084) l-[2-(l-chlorocyclopropyl)-3-(2-fluorophenyl)-2- hydroxypropyl] - 1 H-imidazole-5 -carbonitrile ;
(B) Inhibitors of the respiratory chain at complex I or II, for example, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B004) carboxin, (B005) fluopyram, (B006) flutolanil, (B007) fluxapyroxad, (B008) furametpyr, (B009) Isofetamid, (B010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (B015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (B016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (B017) penflufen, (B018) penthiopyrad, (B019) pydiflumetofen, (B020) Pyraziflumid, (B021) sedaxane, (B022) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-l H-pyrazole-4-carboxamide, (B023) 1,3- dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B024) 1,3- dimethyl-N-[(3S)-l,l,3-trimethyl-2, 3-dihydro- lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B025) 1- methyl-3-(trifhioromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B026) 2- fluoro-6-(trifluoromethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl)benzamide, (B027) 3-
(difluoromethyl)- 1 -methyl-N -(1,1 ,3 -trimethyl-2,3 -dihydro- lH-inden-4-yl)-lH- pyrazole-4-carboxamide, (B028) 3-(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl]-lH-pyrazole-4- carboxamide (inpyrfluxam), (B029) 3-(difluoromethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro- lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B030) 3-(diiluoromethyl)-N-(7-fluoro-l,l,3- trimethyl-2, 3- dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazole-4-carboxamide (Fluindapyr), (B031) 3- (difluoromethyl)- N-[(3R)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole-4-carboxamide, (B032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl]-l-methyl- 1 H- pyrazole-4-carboxamide, (B033) 5,8-difluoro-N-[2-(2-fluoro-4-{ [4-(trifluoromethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazolin-4-amine, (B034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3- (difluoromethyl) -5 -fluoro-1 -methyl -l-H-pyrazole-4-carboxamide, (B035) N-(2-tert-butyl-5- methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide (isoflucpyram), (B039) N-[(lR,4S)-9-(dichloromethylene)-l,2,3,4- tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3-(difluoromethyl)- 1 -methyl- 1 H-pyrazole-4-carboxamide, (B040) N-[(lS,4R)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3-
(difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide, (B041) N-[l-(2,4-dichlorophenyl)- 1- methoxypropan-2-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (B042) N-[2-chloro-6- (trifluoromethyl)benzyl] -N -cyclopropyl-3 -(difluoromethyl)-5 -fluoro- 1 -methyl- lH-pyrazole-4- carboxamide, (B043) N-[3-chloro-2-fluoro-6-(triiluoromethyl)benzyl]-N-cyclopropyl-3-(diiluoromethyl)- 5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N- cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B045) N- cyclopropyl-3-(difhioromethyl)-5-fluoro-l-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-lH-pyrazole-
4-carboxamide, (B046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l- methyl-lH-pyrazole-4-carboxamide, (B047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-
5-methylbenzyl)-l -methyl- lH-pyrazole-4-carboxamide, (B048) N-cyclopropyl-3-(difluoromethyl)-5- fluoro-N-(2-isopropylbenzyl)-l -methyl -IH-pyrazole-4-carbothioamide, (B049) N-cyclopropyl-3-
(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (B050) N- cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l-methyl-lH-pyrazole-4- carboxamide, (B051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide, (B052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5- fluorobenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B053) N-cyclopropyl-3-(difluoromethyl)- N-(2-ethyl-5-methylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B054) N-cyclopropyl-N-(2- cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B056) N -cyclopropyl-N-(2-cy clopropylbenzyl) -3 -(difluoromethyl) -5 -fluoro- 1 -methyl- 1 H- pyrazole-4-carboxamide, (B057) 2-(difluoromethyl)-N-(l,l-dimethyl-3-propyl-2,3-dihydro-lH-inden-4- yl)nicotinamide, (B058) pyrapropoyne;
(C) Inhibitors of the respiratory chain at complex III, for example, (COOl) ametoctradin, (C002) amisulbrom, (C003) azoxystrobin, (C004) coumethoxystrobin, (C005) coumoxystrobin, (C006) cyazofamid, (C007) dimoxystrobin, (C008) enoxastrobin, (C009) famoxadone, (COIO) fenamidone, (C011) flufenoxystrobin, (C012) fluoxastrobin, (C013) kresoxim-methyl, (C014) metominostrobin, (C015) orysastrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C018) pyrametostrobin, (C019) pyraoxystrobin, (C020) trifloxystrobin, (C021) (2E)-2-{2-[({ [(lE)-l-(3-{ [(E)-l-fluoro-2- phenylvinyl]oxy} phenyl)ethylidene] amino} oxy)methyl]phenyl } -2-(methoxyimino )-N- methylacetamide, (C022) (2E,3Z)-5-{ [l-(4-chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3- dimethylpent-3- enamide, (C023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N- methylacetamide, (C024) (2S)-2- { 2-[(2,5-dimethylphenoxy)methyl]phenyl } -2-methoxy-N- methylacetamide, (C025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-yl-2-methylpropanoate (Fenpicoxamid), (C026) 2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (Mandestrobin), (C027) N- (3-ethyl- 3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (C028) (2E,3Z)-5-{ [l-(4- chloro-2-fluorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (C029) methyl {5-[3-(2,4-dimethylphenyl)-lH-pyrazol-l-yl]-2-methylbenzyl}carbamate, (C030) l-(2-{ [l-(4- chlorophenyl)pyrazol-3-yl]oxymethyl}-3-methylphenyl)-l,4-dihydro-4-methyl-5H-tetrazol-5-one (Metyltetraprole), (C031) florylpicoxamid;
(D) Inhibitors of the mitosis and cell division, for example, (D001) carbendazim, (D002) diethofencarb, (D003) ethaboxam, (D004) fluopicolide, (D005) pencycuron, (D006) thiabendazole, (D007) thiophanate-methyl, (D008) zoxamide, (D009) 3-chloro-4-(2,6-difluorophenyl)-6- methyl-5- phenylpyridazine, (D010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6- methylpylidazine, (D011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl)pyridazine, (DO 12) 4-(2- bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-l ,3-dimethyl- lH-pyrazol-5-amine, (DO 13) 4-(2-bromo- 4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)- 1,3-dimethyl- 1H- pyrazol-5-amine, (DO 14) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-l,3-dimethyl-lH-pyrazol-5- amine, (D015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-l, 3-dimethyl- lH-pyrazol-5- amine, (D016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (DO 17) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)- 1 ,3-dimethyl- 1 H-pyrazol-5 -amine, (DO 18) 4-(2- chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (D019) 4-(2-chloro-4- fluorophenyl)-N-(2-chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (D020) 4-(2-chloro-4- fluorophenyl)-N-(2-chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (D021) 4-(2-chloro-4- fluorophenyl)-N-(2-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (D022) 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3 ,6-dimethylpyridazine, (D023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4- fluorophenyl)-l, 3-dimethyl- lH-pyrazol-5-amine, (D024) N-(2-bromophenyl)-4-(2-chloro-4- fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (D025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4- fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine;
(E) Compounds capable to have a multisite action, for example (E001) bordeaux mixture, (E002) captafol, (E003) captan, (E004) chlorothalonil, (E005) copper hydroxide, (E006) copper naphthenate, (E007) copper oxide, (E008) copper oxychloride, (E009) copper(2+) sulfate, (E010) dithianon, (E011) dodine, (E012) folpet, (E013) mancozeb, (E014) maneb, (E015) metiram, (E016) metiram zinc, (E017) oxine-copper, (E018) propineb, (E019) sulfur and sulfur preparations including calcium polysulfide, (E020) thiram, (E021) zineb, (E022) ziram, (E023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H- pynolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile;
(F) Compounds capable to induce a host defence, for example (F001) acibenzolar-S-methyl, (F002) isotianil, (F003) probenazole, (F004) tiadinil;
(G) Inhibitors of the amino acid and/or protein biosynthesis, for example (G001) cyprodinil, (G002) kasugamycin, (G003) kasugamycin hydrochloride hydrate, (G004) oxytetracycline, (G005) pyrimethanil, (G006) 3 -(5 -fluoro-3 ,3 ,4,4-tetramethyl-3 ,4-dihydroisoquinolin- 1 -yl)quinoline;
(H) Inhibitors of the ATP production, for example (H001) silthiofam;
(I) Inhibitors of the cell wall synthesis, for example (1001) benthiavalicarb, (1002) dimethomorph, (1003) flumorph, (1004) iprovalicarb, (1005) mandipropamid, (1006) pyrimorph, (1007) valifenalate, (1008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en-l-one, (1009) (2Z)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one;
(J) Inhibitors of the lipid and membrane synthesis, for example (J001) propamocarb, (J002) propamocarb hydrochloride, (J003) tolclofos-methyl;
(K) Inhibitors of the melanin biosynthesis, for example (K001) tricyclazole, (K002) 2,2,2- trifluoroethyl { 3-methyl- 1 -[(4-methylbenzoyl )amino]butan-2-yl [carbamate;
(L) Inhibitors of the nucleic acid synthesis, for example (L001) benalaxyl, (L002) benalaxyl-M (kiralaxyl), (L003) metalaxyl, (L004) metalaxyl-M (mefenoxam);
(M) Inhibitors of the signal transduction, for example (M001) fludioxonil, (M002) iprodione, (M003) procymidone, (M004) proquinazid, (M005) quinoxyfen, (M006) vinclozolin;
(N) Compounds capable to act as an uncoupler, for example (N001) fluazinam, (N002) meptyldinocap;
(O) Further compounds, for example (O001) Abscisic acid, (0002) benthiazole, (0003) bethoxazin, (0004) capsimycin, (0005) carvone, (0006) chinomethionat, (0007) cufraneb, (0008) cyflufenamid, (0009) cymoxanil, (O010) cyprosulfamide, (O011) flutianil, (0012) fosetyl-aluminium, (0013) fosetyl- calcium, (0014) fosetyl-sodium, (0015) methyl isothiocyanate, (0016) metrafenone, (0017) mildiomycin, (0018) natamycin, (0019) nickel dimethyldithiocarbamate, (0020) nitrothal-isopropyl, (0021) oxamocarb, (0022) Oxathiapiprolin, (0023) oxyfenthiin, (0024) pentachlorophenol and salts, (0025) phosphorous acid and its salts, (0026) propamocarb -fosetylate, (0027) pyriofenone (chlazafenone), (0028) tebufloquin, (0029) tecloftalam, (0030) tolnifanide, (0031) l-(4-{4-[(5R)-5-(2,6- difhiorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (0032) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-l ,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifhioromethyl)-lH-pyrazol-l-yl]ethanone, (0033) 2-(6-benzylpyridin-2-yl)quinazoline, (0034) 2,6-dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6- c'] dipyrrole- 1 ,3 ,5 ,7(2H,6H)-tetrone, (0035) 2- [3 ,5 -bis(difluoromethyl)-lH-pyrazol- 1 -yl] - 1 - [4 (4- { 5- [2- (prop-2-yn- 1-yloxy )phenyl]-4, 5 -dihydro-1, 2-oxazol-3-yl}-l,3-thiazol -2 -yl)piperidin-l-yl]ethanone,
(0036) 2- [3 ,5 -bis(difluoromethyl)- lH-pyrazol- 1 -yl] - 1 - [4-(4- { 5 -[2-chloro-6-(prop-2-yn- 1 -yloxy)phenyl] - 4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0037) 2-[3,5- bis(difluoromethyl)-lH-pyrazol- 1 -yl] - 1 - [4-(4- { 5 - [2-fluoro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5 -dihydro- 1,2- oxazol-3-yl]-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0038) 2-[6-(3-fluoro-4-methoxyphenyl)-5- methylpyridin-2-yl]quinazoline, (0039) 2-{(5R)-3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (0040) 2- { (5 S)-3- [2-( 1 - { [3 ,5 -bis(difluoromethyl)- 1 H-pyrazol- 1 -yl] acetyl }piperidin-4- yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl]-3-chlorophenyl methanesulfonate, (0041) 2-{2-[(7,8- difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (0042) 2-{2-fluoro-6-[(8-fluoro-2- methylquinolin-3-yl)oxy]phenyl]propan-2-ol, (0043) 2-{3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (fluoxapiprolin), (0044) 2-{3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl {phenyl methanesulfonate, (0045) 2-phenylphenol and salts, (0046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (0047) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline (Quinofumelin), (0048) 4- amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5- fluoropyrimidin-2(lH)-one), (0049) 4-oxo- 4-[(2-phenylethyl)amino]butanoic acid, (0050) 5-amino- l,3,4-thiadiazole-2-thiol, (0051) 5-chloro-N'- phenyl-N'-(prop-2-yn-l-yl)thiophene-2-sulfonohydrazide, (0052) 5-fluoro-2-[(4- fluorobenzyl)oxy]pyrimidin-4-amine, (0053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4- amine,(O054) 9-fluoro-2, 2-dimethyl -5-(quinolin-3-yl)-2,3-dihydro-l,4-benzoxazepine, (0055) but-3- yn- 1-yl { 6-[({ [(Z)-(l -methyl- lH-tetrazol-5-yl)(phenyl)methylene]amino } oxy)methyl]pyridin-2- yl [carbamate, (0056) ethyl (2Z)-3-amino-2- cyano-3-phenylacrylate, (0057) phenazine-1 -carboxylic acid, (0058) propyl 3,4,5-trihydroxybenzoate, (0059) quinolin-8-ol, (0060) quinolin-8-ol sulfate (2:1), (0061) tert-butyl { 6-[({ [(1 -methyl- lH-tetrazol-5-yl)(phenyl)methylene]amino }oxy)methyl]pyridin-2- yl {carbamate, (0062) 5-fluoro-4-imino-3-methyl-l-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin- 2(lH)-one, (0063) pyridachlometyl, (0064) ipflufenoquin, (0065) aminopyrifen.
(P) Inhibitors of histone deacetylase for example (P001) N-(l-ethylcyclopropyl)-4-[5- (trifhioromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P002) N-(2-isopropylcyclopropyl)-4-[5- (triiluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P003) N-(2-methylcyclopropyl)-4-[5-
(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]benzamide; (P004) N-(l -methylcyclopropyl)-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P005) N-(2-ethylcyclopropyl)-4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]benzamide; (P006) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]benzamide; (P007) 5-(trifluoromethyl)-3-[4-[[3-(trifbioromethyl)-l,2,4triazol-l-yl]methyl]phenyl]-
1.2.4-oxadiazole; (P008) 2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazole-3- carbonitrile; (P009) ethyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate; (P010) N-cyclopropyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxamide; (P011) N,N-dimethyl-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P012) N-methyl-l-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P013) N,N, -dimethyl -H[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazol-3-amine; (P014) 3-[4-[(5- ethylsulfanyl-l,2,4-triazol-l-yl)methyl]phenyl]-5-(trifluoromethyl)-l,2,4-oxadiazole; (P015) 3-[4-
(triazolo[4,5-b]pyridin-l-ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole; (P016) 3-[4-
(triazolo[4,5-b]pyridin-2-ylmethyl)phenyl]-5-(trifLuoromethyl)-l,2,4-oxadiazole; (P017) 3-[4-
(triazolo[4,5-b]pyridin-3-ylmethyl)phenyl]-5-(trifluoromethyl)- 1,2,4-oxadiazole; (P018) methyl l-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (P019) ethyl l-[[3-fluoro- 4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (P020) A/ZV-diethyl- l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P021) N- methoxy-/V-methyl - 1 -[[4-[5-(trilbioromethyl )- 1 , 2, 4-oxadiazo l-3-yl] phenyl ]methy l]pyrazole-4- carboxamide; (P022) propyl l-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate; (P023) /V-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide; (P024) /V-ethyl-l-[[4-[5-(triiluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide; (P025) l-[[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxamide; (P026) /V-methoxy-l-[l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazol-4-yl]methanimine; (P027) ethyl l-[l-[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]ethyl]pyrazole-4-carboxylate; (P028) l-[[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrobdin-2-one; (P029) l-[[4-[5-(triiluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P030) 4-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]morphobn-3-one; (P031) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazolidin-3-one; (P032) 2-[[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazobdin-3-one; (P033) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazobdin-3-one; (P034) 3,3-dimethyl-l [4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P035) l-[[2-fluoro-4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one; (P036) l-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- y 1 ] phenyl ] methyl] piperidin-2-one ; (P037) 2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- y 1 ] phenyl ] methyl] oxazinan- 3 -one ; (P038) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P039) 3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]oxazolidin-2-one; (P040) 1 -methyl-3- [ [4-[5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3- yl]phenyl]methyl]imidazolidin-2-one; (P041) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-3,3-dimethyl-piperidin-2-one; (P042) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one; (P043) 2-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]-4,4-dimethyl-isoxazolidin-3-one; (P044) 2-[[2,3-difluoro-4-[5-
( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one; (P045) 2-[[3-fluoro-4-[5- ( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one; (P046) l-[[3-fluoro-4-[5- ( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one; (P047) N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P048) 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]but-3-ynamide; (P049) N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P050) 3-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P051) 2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]prop-2-enamide; (P052) 2-methyl-N-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P053) 2-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] ; (P054) 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P055) 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide; (P056) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]butanamide; (P057) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide; (P058) 2-(difluoromethoxy)-N-[[4-[5- ( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]acetamide; (P059) 2-methoxy-2-methyl-N-[[4-[5- ( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P060) l-methyl-3-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P061) l-ethyl-l-methyl-3-[[4-[5- ( trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]urea; (P062) l-ethoxy-3-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]urea; (P063) l-methoxy-l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]; (P064) l,l-diethyl-3-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P065) N-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide; (P066) N-methoxy-N-[[4-[5-(trifhioromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]pent-4-ynamide; (P067) N-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide; (P068) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P069) N-cyclopropyl-3,3,3-trifluoro-N-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P070) 2,2-difluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclo propanecarboxamide; (P071) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P072) N-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-N-methoxy -propanamide; (P073) 2-methoxy-N-(2,2,2-trifluoroethyl)-N-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl] acetamide; (P074) N-[[2,3-difluoro-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-cyclopropane carboxamide; (P075) 2- (difluoromethoxy)-N-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide; (P076) N-ethoxy-2-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P077) N-isopropyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]tetrahydrofuran-2 -carboxamide; (P078) l-methoxy-3-methyl-l-[[4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P079) 3-cyclopropyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]urea; (P080) 3-ethoxy-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P081) 3-allyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol- 3-yl]phenyl]methyl]urea; (P082) l-cyclopropyl-3-methoxy-3-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P083) 3-isopropyl- l-methoxy-l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P084) l-methoxy-3-prop-2-ynyl-l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P085) l-[[3-fhioro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] - 1 -methoxy-3-methyl-urea; (P086) 3 -(cyclopropylmethyl)- 1 -methyl- 1 -[ [4- [5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P087) l-ethyl-3-(2,2,2-trifluoroethyl)-l-[[4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P088) l,3-dimethoxy-l-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P089) 3-ethyl-l-methoxy-l-[[4-[5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P090) N-methyl-4-[5-(trilluoromethyl)-
1.2.4-oxadiazol-3-yl]benzamide; (P091) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]benzamide; (P092) N-[(Z)-methoxyiminomethyl]-4-[5-(triiluoromethyl)-l,2,4-oxadiazol- 3-yl]benzamide; (P093) N-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]cyclopropanecarboxamide; (P094) N-(2-lluorophenyl)-4-[5-(triiluoromethyl)-l,2,4-oxadiazol- 3-yl]benzamide; (P095) 2,2-difluoro-N-methyl-2-[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]acetamide; (P096) N-allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] acetamide; (P097) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trilluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide; (P098) N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P100) N-allyl-N-[[4-[5-(trilluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide; (P101) 4, 4-dimethyl- l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one; (P102) N-methyl-4-[5-(trilluoromethyl)-l ,2,4-oxadiazol- 3-yl]benzenecarbothioamide; (P103) 5-methyl- l-[[4-[5-(trifluoromethyl)-l, 2, 4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one, (P104) N-methyl-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]benzenecarboxamide; (P105) Nl-methyl-N2-(4-(5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl)benzyl)oxal amide.
All named mixing partners of the classes (A) to (P) can, if their functional groups enable this, optionally form salts with suitable bases or acids.
Further compounds capable to act as a safener, for example compounds of the group of heterocyclic carboxylic acid derivatives such as for example compounds of the type of dichlorophenylpyrazoline-3- carboxylic acid, preferably compounds such as (Q001) l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2-pyrazoline-3-carboxylic acid, (Q002) ethyl l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2-pyrazoline-3-carboxylate ("mefenpyr (-diethyl)"), and related compounds, as described in WO199107874.
Where a compound (1) or a compound (2) can be present in tautomeric form, such a compound is understood hereinabove and hereinbelow also to include, where applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case.
The active ingredients specified herein by their common name are known and described, for example, in the pesticide manual (16th Ed. British Crop Protection Council) or can be searched in the internet (e.g. www.alanwood.net/pesticides).
A particularly preferred composition of compound (I) according to the invention comprises at least one further active compound (2) selected from:
(A) Inhibitors of the ergosterol biosynthesis, for example, (A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A004) fenhexamid, (A005) fenpropidin, (A006) fenpropimorph, (A007) fenpyrazamine, (A008) fluquinconazole, (A009) flutriafol, (A010) imazalil, (A011) imazalil sulfate, (A012) ipconazole, (A013) metconazole, (A014) myclobutanil, (A015) paclobutrazol, (A016) prochloraz, (A017) propiconazole, (A018) prothioconazole, (A019) Pyrisoxazole, (A020) spiroxamine, (A021) tebuconazole, (A022) tetraconazole, (A023) triadimenol, (A024) tridemorph, (A025) triticonazole, (A026) (lR,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol- l-ylmethyl)cyclopentanol, (A027) (lS,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH- l,2,4-triazol-l-ylmethyl)cyclopentanol, (A028) (2R)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2- dichlorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (A029) (2R)-2-(l-chlorocyclopropyl)-4-[(lS)-2,2- dichlorocyclopropyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A030) (2R)-2- [4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A031) (2S)-2-(l-chlorocyclopropyl)-4- [( lR)-2,2-dichlorocyclopropyl] - 1 -( lH-l,2,4-triazol- 1 -yl)butan-2-ol, (A032) (2S)-2-( 1 - chlorocyclopropyl)-4-[(l S)-2,2-dichlorocyclopropyl] - 1 -( 1 H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A033) (2S)-2- [4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A034) (R)-[3-(4- chloro-2-fhiorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (A035) (S)-[3-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridiii-3-yl)methanol, (A036) [3- (4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- 1 ,2-oxazol-4-yl](pyridin-3-yl)methanol, (A037) 1 -
( { (2R,4S)-2- [2-chloro-4-(4-chlorophenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2-yl } methyl)- 1H- 1 ,2,4- triazole, (A038) l-({ (2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2- yl}methyl)-lH- 1,2, 4-triazole, (A039) l-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A040) l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A041) l-{ [rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4-triazol-5-yl thiocyanate, (A042) 2- [(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3-thione, (A043) 2-[(2R,4R,5S)- 1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-l,2,4-triazole-3-thione, (A044) 2-[(2R,4S,5R)- l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A045) 2-[(2R,4S,5S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A046) 2-[(2S,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A047) 2- [(2S ,4R,5 S)- 1 -(2,4-dichlorophenyl)-5 -hydroxy-2, 6, 6-trimethylheptan-4-yl] - 2,4-dihydro-3H-l,2,4-triazole-3-thione, (A048) 2-[(2S,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3 -thione, (A049) 2- [(2S ,4S ,5 S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A050) 2- [l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A052) 2-[2- chloro-4-(4-chlorophenoxy)phenyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A053) 2- [4-(4-chlorophenoxy)- 2-(trifluoromethyl)phenyl] - 1 -(1H- 1 ,2,4-triazol- 1 -yl)butan-2-ol, (A054) 2- [4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l -yl)pentan-2-ol, (A055) 2-[4-(4-chlorophenoxy)-2-
(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A056) 2-{[3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A057) 2-{[rel(2R,3R)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-dilluorophenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l ,2,4- triazole-3 -thione, (A059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-l-(lH-l,2,4-triazol-l- ylmethyl)cyclopentanol, (A060) 5-(allylsulfanyl)-l-{[3-(2-chlorophenyl)-2-(2,4-dilluorophenyl)oxiran-2- yljmethyl } - 1 H- 1 ,2,4-triazole, (A061) 5 -(allylsulfanyl)- 1 - { [rel(2R,3R)-3-2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l, 2 4-triazole, (A062) 5-(allylsulfanyl)-l-{[rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH- 1,2, 4-triazole, (A063) N'-(2,5-dimethyl-4- {[3-(l,l,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (A064) N'- (2, 5 -dimethyl-4- { [3-(2, 2, 2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidofonnamide, (A065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methylimidoformamide,(A066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N- ethyl-N-methylimidoformamide, (A067) N'-(2,5-dimethyl-4-{3-[(l,l,2,2- tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (A068) N'-(2,5-dimethyl- 4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (A069) N'-(2,5- dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidofonnamide, (A070) N'-(2,5- dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methylimidoformamide, (A071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (A072) N'-(4-{ [3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N- methylimidoformamide, (A073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N- ethyl-N-methylimidoformamide, (A074) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2-yloxy)-2- methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (A075) N'-{ 4-[(4,5-dichloro-l ,3-thiazol-2- yl)oxy] -2,5-dimethylphenyl } -N-ethyl-N-methylimidoformamide, (A076) N'- { 5-bromo-6- [(1 R)-l-(3,5- difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofonnamide, (A077) N'-{5- bromo-6- [( lS)-l-(3,5 -dilluorophenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidoformamide, (A078) N'- { 5 -bromo-6- [(cis-4-isopropylcyclohexyl)oxy ] -2-methylpyridin-3 -yl } -N-ethyl-N- methylimidofornamide, (A079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3- yl } -N-ethyl-N-methylimidoformamide, (A080) N'- { 5 -bromo-6- [ 1 -(3 ,5-difluorophenyl)ethoxy ] -2- methy lpyri din-3 -yl} -N-ethyl-N-methylimidoformamide, (A081) Mefentrifluconazole, (A082)
Ipfentrifluconazole, (A083) l-(2,4-difluorophenyl)-2-(lH-l,2,4-triazol-l-yl)-l-[l-(2,6-difluoro-4- chlorophenoxy)cyclopropyl] ethanol, (A084) l-[2-(l-chlorocyclopropyl)-3-(2-fluorophenyl)-2- hydroxypropyl] - 1 H-imidazole-5 -carbonitrile ;
(B) Inhibitors of the respiratory chain at complex I or II, for example, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B004) carboxin, (B005) fluopyram, (B006) flutolanil, (B007) fluxapyroxad, (B008) furametpyr, (B009) Isofetamid, (B010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (B015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (B016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (B017) penflufen, (B018) penthiopyrad, (B019) pydiflumetofen, (B020) Pyraziflumid, (B021) sedaxane, (B022) l,3-dimethyl-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)-l H-pyrazole-4-carboxamide, (B023) 1,3- dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B024) 1,3- dimethyl-N-[(3S)-l,l,3-trimethyl-2, 3-dihydro- lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B025) 1- methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B026) 2- fluoro-6-(trifluoromethyl)-N-(l,l,3-trimethyl-2, 3-dihydro- lH-inden-4- yl)benzamide, (B027) 3-
(difluoromethyl)- 1 -methyl-N -(1,1 ,3 -trimethyl-2,3 -dihydro- lH-inden-4-yl)-lH- pyrazole-4-carboxamide, (B028) 3-(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH- inden-4-yl]-lH-pyrazole-4- carboxamide (inpyrfhixam), (B029) 3-(difluoromethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-2,3-dihydro- lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B030) 3-(difluoromethyl)-N-(7-fluoro-l,l,3- trimethyl-2, 3- dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazole-4-carboxamide (Fluindapyr), (B031) 3- (difluoromethyl)- N-[(3R)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole-4-carboxamide, (B032) 3-(difluoromethyl)-N-[(3S)-7-lluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4- yl]-l-methyl- 1 H- pyrazole-4-carboxamide, (B033) 5,8-difluoro-N-[2-(2-fluoro-4-{ [4-(trifluoromethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazolin-4-amine, (B034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3- (difluoromethyl) -5 -fluoro-1 -methyl -l-H-pyrazole-4-carboxamide, (B035) N-(2-tert-butyl-5- methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide, (B039) N-[(lR,4S)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4- methanonaphthalen-5-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (B040) N-[(1S,4R)- 9-(dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3 -(difluoro methyl)- 1 -methyl- 1H- pyrazole-4-carboxamide, (B041) N-[l-(2,4-dichlorophenyl)- l-methoxypropan-2-yl]-3-(dilluoromethyl)- l-methyl-lH-pyrazole-4-carboxamide, (B042) N-[2-chloro-6-(trilluoromethyl)benzyl]-N-cyclopropyl-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B043) N-[3-chloro-2-fluoro-6- (trifluoromethyl)benzyl] -N -cyclopropyl-3 -(dilluoromethyl)-5 -fluoro-1 -methyl- lH-pyrazole-4- carboxamide, (B044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5- fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l- methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-lH-pyrazole-4-carboxamide, (B046) N-cyclopropyl-3- (difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-l -methyl- lH-pyrazole-4-carboxamide, (B047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-l -methyl- lH-pyrazole-4- carboxamide, (B048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l -methyl -IH- pyrazole-4-carbothioamide, (B049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l- methyl-lH-pyrazole-4-carboxamide, (B050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2- isopropylbenzyl)-l -methyl -lH-pyrazole-4-carboxamide, (B051) N-cyclopropyl-3-(difluoromethyl)-N-(2- ethyl-4,5-dimethylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B052) N-cyclopropyl-3- (difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B053) N- cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l- methyl-lH-pyrazole-4-carboxamide, (B055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3- (difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B056) N-cyclopropyl-N-(2- cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B057) 2-
(difluoromethyl)-N-(l, 1 -dimethyl-3-propyl -2, 3-dihydro- lH-inden-4- yl)nicotinamide, (B058) pyrapropoyne;
(C) Inhibitors of the respiratory chain at complex III, for example, (COOl) ametoctradin, (C002) amisulbrom, (C003) azoxystrobin, (C004) coumethoxystrobin, (C005) coumoxystrobin, (C006) cyazofamid, (C007) dimoxystrobin, (C008) enoxastrobin, (C009) famoxadone, (COIO) fenamidone, (C011) flufenoxystrobin, (C012) fluoxastrobin, (C013) kresoxim-methyl, (C014) metominostrobin, (C015) orysastrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C018) pyrametostrobin, (C019) pyraoxystrobin, (C020) trifloxystrobin, (C021) (2E)-2-{2-[({ [(lE)-l-(3-{ [(E)-l-fluoro-2- phenylvinyl]oxy} phenyl)ethylidene] amino} oxy)methyl]phenyl } -2-(methoxyimino )-N- methylacetamide, (C022) (2E,3Z)-5-{ [l-(4-chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3- dimethylpent-3- enamide, (C023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N- methylacetamide, (C024) (2S)-2- { 2-[(2,5-dimethylphenoxy)methyl]phenyl } -2-methoxy-N- methylacetamide, (C025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-yl-2-methylpropanoate (Fenpicoxamid), (C026) 2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (Mandestrobin), (C027) N- (3-ethyl- 3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (C028) (2E,3Z)-5-{ [l-(4- chloro-2-fluorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (C029) methyl {5-[3-(2,4-dimethylphenyl)-lH-pyrazol-l-yl]-2-methylbenzyl}carbamate, (C030) l-(2-{ [l-(4- chlorophenyl)pyrazol-3-yl]oxymethyl}-3-methylphenyl)-l,4-dihydro-4-methyl-5H-tetrazol-5-one (Metyltetraprole), (C031) florylpicoxamid;
(E) Compounds capable to have a multisite action, for example (E001) bordeaux mixture, (E002) captafol, (E003) captan, (E004) chlorothalonil, (E005) copper hydroxide, (E006) copper naphthenate, (E007) copper oxide, (E008) copper oxychloride, (E009) copper(2+) sulfate, (E010) dithianon, (E011) dodine, (E012) folpet, (E013) mancozeb, (E014) maneb, (E015) metiram, (E016) metiram zinc, (E017) oxine-copper, (E018) propineb, (E019) sulfur and sulfur preparations including calcium polysulfide, (E020) thiram, (E021) zineb, (E022) ziram, (E023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H- pynolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile;
(L) (L003) metalaxyl, (L004) metalaxyl-M (mefenoxam),
(M) (M001) fludioxonil, (M002) iprodione, (M004) proquinazid, (M005) quinoxyfen,
(N) (N001) fluazinam, (N002) meptyldinocap,
(O) Further compounds, for example (O001) Abscisic acid, (0002) benthiazole, (0003) bethoxazin,
(0004) capsimycin, (0005) carvone, (0006) chinomethionat, (0007) cufraneb, (0008) cyflufenamid, (0009) cymoxanil, (OOIO) cyprosulfamide, (OOll) llutianil, (0012) fosetyl-aluminium, (0013) fosetyl- calcium, (0014) fosetyl-sodium, (0015) methyl isothiocyanate, (0016) metrafenone, (0017) mildiomycin, (0018) natamycin, (0019) nickel dimethyldithiocarbamate, (0020) nitrothal-isopropyl, (0021) oxamocarb, (0022) Oxathiapiprolin, (0023) oxyfenthiin, (0024) pentachlorophenol and salts, (0025) phosphorous acid and its salts, (0026) propamocarb-fosetylate, (0027) pyriofenone (chlazafenone), (0028) tebufloquin, (0029) tecloftalam, (0030) tolnifanide, (0031) l-(4-{4-[(5R)-5-(2,6- difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (0032) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-l ,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (0033) 2-(6-benzylpyridin-2-yl)quinazoline, (0034) 2,6-dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6- c'] dipyrrole- 1 ,3 ,5 ,7(2H,6H)-tetrone, (0035) 2- [3 ,5 -bis(difluoromethyl)-lH-pyrazol- 1 -yl] - 1 - [4 (4- { 5- [2- (prop-2-yn- 1-yloxy )phenyl]-4, 5 -dihydro-1, 2-oxazol-3-yl}-l,3-thiazol -2 -yl)piperidin-l-yl]ethanone,
(0036) 2- [3 ,5 -bis(difluoromethyl)- lH-pyrazol- 1 -yl] - 1 - [4-(4- { 5 -[2-chloro-6-(prop-2-yn- 1 -yloxy)phenyl] - 4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0037) 2-[3,5- bis(difluoromethyl)-lH-pyrazol- 1 -yl] - 1 - [4-(4- { 5 - [2-fluoro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5 -dihydro- 1,2- oxazol-3-yl]-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0038) 2-[6-(3-fluoro-4-methoxyphenyl)-5- methylpyridin-2-yl]quinazoline, (0039) 2-{(5R)-3-[2-(l-{ [3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl]-3-chlorophenyl methanesulfonate, (0040) 2- { (5 S)-3- [2-( 1 - { [3 ,5 -bis(difluoromethyl)- 1 H-pyrazol- 1 -yl] acetyl }piperidin-4- yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl]-3-chlorophenyl methanesulfonate, (0041) 2-{2-[(7,8- difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (0042) 2-{2-fluoro-6-[(8-fluoro-2- methylquinolin-3-yl)oxy]phenyl]propan-2-ol, (0043) 2-{3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl]-3-chlorophenyl methanesulfonate (fluoxapiprolin), (0045) 2-phenylphenol and salts, (0046) 3-(4,4,5-trifluoro-3,3- dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (0047) 3-(4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinolin-l-yl)quinoline (Quinofumelin), (0048) 4-amino-5-fluoropyrimi din-2 -ol (tautomeric form: 4-amino-5- fluoropyrimidin-2(lH)-one), (0049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (0050) 5-amino- l,3,4-thiadiazole-2-thiol, (0051) 5-chloro-N'-phenyl-N'-(prop-2-yn-l-yl)thiophene-2- sulfonohydrazide, (0052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (0053) 5-fluoro-2-[(4- methylbenzyl)oxy]pyrimidin-4-amine, (0054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2, 3-dihydro- 1,4- benzoxazepine, (0055) but-3-yn-l-yl{ 6-[({ [(Z)-(l-methyl-lH-tetrazol-5-yl)(phenyl)methylene]amino} oxy)methyl]pyridin-2-yl } carbamate, (0056) ethyl (2Z) -3 -amino-2- cyano-3-phenylacrylate, (0057) phenazine-1 -carboxylic acid, (0058) propyl 3,4,5-trihydroxybenzoate, (0059) quinolin-8-ol, (0060) quinolin-8-ol sulfate (2:1), (0061) tert-butyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamate, (0062) 5 -fluoro-4-imino-3 -methyl- 1 - [(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(lH)-one, (0063) pyridachlometyl, (0064) ipflufenoquin, (0065) aminopyrifen.
(P) Inhibitors of histone deacetylase for example (P001) N-(l-ethylcyclopropyl)-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P002) N-(2-isopropylcyclopropyl)-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P003) N-(2-methylcyclopropyl)-4-[5-
(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]benzamide; (P004) N-(l -methylcyclopropyl)-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P005) N-(2-ethylcyclopropyl)-4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]benzamide; (P006) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yljbenzamide; (P007) 5-(trifluoromethyl)-3-[4-[[3-(trifluoromethyl)-l,2,4triazol-l-yl]methyl]phenyl]-
1.2.4-oxadiazole; (P008) 2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazole-3- carbonitrile; (P009) ethyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate; (P010) N-cyclopropyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxamide; (P011) N,N-dimethyl-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P012) N-methyl-l-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P013) N,N, -dimethyl -H[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazol-3-amine; (P014) 3-[4-[(5- ethylsulfanyl-l,2,4-triazol-l-yl)methyl]phenyl]-5-(trifluoromethyl)-l,2,4-oxadiazole; (P015) 3-[4-
(triazolo[4,5-b]pyridin-l-ylmethyl)phenyl]-5-(trifluoromethyl)-l,2,4-oxadiazole; (P016) 3-[4-
(triazolo[4,5-b]pyridin-2-ylmethyl)phenyl]-5-(trifluoromethyl)-l,2,4-oxadiazole; (P017) 3-[4-
(triazolo[4,5-b]pyridin-3-ylmethyl)phenyl]-5-(trifluoromethyl)-l,2,4-oxadiazole; (P018) methyl l-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (P019) ethyl l-[[3-fluoro- 4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (P020) A(/V-diethyl- l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P021) N- methoxy-AZ-methyl- 1 -[[4-[5-(trilhioromethyl )- 1 , 2, 4-oxadiazo l-3-yl] phenyl Jmethy l]pyrazole-4- carboxamide; (P022) propyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate; (P023) lV-methoxy-l-[[4-[5-(trifluaromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxamide; (P024) /V-ethyl- 1 -[[4-[5-(trifluoromethyl 1 , 2, 4-oxadiazol -3-yl] phenyl ]methyl]pyrazole- 4-carboxamide; (P025) l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxamide; (P026) /V-methoxy-l-[l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazol-4-yl]methanimine; (P027) ethyl l-[l-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]ethyl]pyrazole-4-carboxylate; (P028) l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one; (P029) l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P030) 4-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]morpholin-3-one; (P031) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazolidin-3-one; (P032) 2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazolidin-3-one; (P033) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]isoxazolidin-3-one; (P034) 3,3-dimethyl-l-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P035) l-[[2-fhioro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one; (P036) l-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P037) 2-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- y 1 ] phenyl ] methyl] oxazinan- 3 -one ; (P038) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P039) 3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]oxazolidin-2-one; (P040) l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]imidazolidin-2-one; (P041) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-3,3-dimethyl-piperidin-2-one; (P042) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one; (P043) 2-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]-4,4-dimethyl-isoxazolidin-3-one; (P044) 2-[[2,3-difluoro-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one; (P045) 2-[[3-fluoro-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one; (P046) l-[[3-fluoro-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one; (P047) N-[[4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P048) 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]but-3-ynamide; (P049) N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P050) 3-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P051) 2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]prop-2-enamide; (P052) 2-methyl-N-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide; (P053) 2-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] ; (P054) 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P055) 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide; (P056) N-[[2,3-difhioro-4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]butanamide; (P057) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide; (P058) 2-(difluoromethoxy)-N-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide; (P059) 2-methoxy-2-methyl-N-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P060) l-methyl-3-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P061) l-ethyl-l-methyl-3-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P062) l-ethoxy-3-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]urea; (P063) l-methoxy-l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P064) l,l-diethyl-3-[[4-[5-(trilluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P065) N-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide; (P066) N-methoxy-N-[[4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]pent-4-ynamide; (P067) N-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide; (P068) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P069) N-cyclopropyl-3,3,3-trifluoro-N-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P070) 2,2-difluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclo propanecarboxamide; (P071) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P072) N-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-N-methoxy -propanamide; (P073) 2-methoxy-N-(2,2,2-trifluoroethyl)-N-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl] acetamide; (P074) N-[[2,3-difluoro-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-cyclopropane carboxamide; (P075) 2- (difbioromethoxy)-N-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide; (P076) N-ethoxy-2-methoxy-N-[[4-[5-(trilluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P077) N-isopropyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]tetrahydrofuran-2 -carboxamide; (P078) 1 -methoxy-3 -methyl- 1 - [ [4- [5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]urea; (P079) 3-cyclopropyl-l-methoxy-l-[[4-[5-(trifhioromethyl)- l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P080) 3-ethoxy-l-methoxy-l-[[4-[5-(trilluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P081) 3-allyl- 1 -methoxy- 1 - [ [4- [5 -(trifluoromethyl)- 1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]urea; (P082) l-cyclopropyl-3-methoxy-3-methyl-l-[[4-[5-(trilluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P083) 3-isopropyl- l-methoxy-l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P084) l-methoxy-3-prop-2-ynyl-l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]urea; (P085) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] - 1 -methoxy-3 -methyl -urea; (P086) 3 -(cyclopropylmethyl)- 1 -methyl- 1 -[ [4- [5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P087) l-ethyl-3-(2,2,2-trifluoroethyl)-l-[[4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P088) l,3-dimethoxy-l-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P089) 3-ethyl-l-methoxy-l-[[4-[5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P090) N-methyl-4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide; (P091) N-[(E)-methoxyiminomethyl]-4-[5-(trifhioromethyl)-l,2,4- oxadiazol-3-yl]benzamide; (P092) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol- 3-yl]benzamide; (P093) N-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]cyclopropanecarboxamide; (P094) N-(2-fluorophenyl)-4-[5-(triiluoromethyl)-l,2,4-oxadiazol- 3-yl]benzamide; (P095) 2,2-difhioro-N-methyl-2-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]acetamide; (P096) N-allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl] acetamide; (P097) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide; (P098) N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P100) N-allyl-N-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide; (P101) 4, 4-dimethyl- l-[[4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one; (P102) N-methyl-4-[5-(trilluoromethyl)-l ,2,4-oxadiazol- 3-yl]benzenecarbothioamide; (P104) N-methyl-4-[5-(trilluoromethyl)-l ,2,4-oxadiazol-3- yl]benzenecarboxamide; (P105) Nl-methyl-N2-(4-(5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl)benzyl)oxal amide.
(Q) Q001) l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2 -pyrazoline-3-carboxylic acid,
(Q002) ethyl l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate ("mefenpyr (-diethyl)"),
Further particularly more preferred compositions of compound (I) according to the invention comprise (2) at least one further active compound selected from:
(A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A006) fenpropimorph, (A009) flutriafol, (A012) ipconazole, (A013) metconazole, (A017) propiconazole, (A018) prothioconazole, (A021) tebuconazole, (A022) tetraconazol, (A081) Mefentrifluconazole, (A082) Ipfentrifluconazole, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B005) fluopyram, (B007) fluxapyroxad, (B009) Isofetamid, (B010) isopyrazam (B017) penflufen, (B018) penthiopyrad, (B019) pydiflumetofen, (B.021) sedaxane, (B028) inpyrfluxam, (B030) 3-(difhioromethyl)-N-(7-fluoro-l,l,3-trimethyl-2,3- dihydro-lH-inden-4-yl)-l-methyl-lH-pyrazole-4-carboxamide (Fluindapyr), (C003) azoxystrobin, (C007) dimoxystrobin, (C012) fluoxastrobm, (C013) kresoxim-methyl, (C014) metominostrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C020) trifloxystrobin, (C025) (3S,6S,7R,8R)-8-benzyl-3-[({3- [(isobutyryloxy)methoxy] -4-methoxypyridin-2-yl } carbonyl)amino] -6-methyl-4,9-dioxo- 1 l,5-dioxonan-7 - yl-2-methylpropanoate (Fenpicoxamid), (C031) florylpicoxamid,
(D001) carbendazim, (D007) thiophanate -methyl (D012) 4-(2-bromo-4-fhiorophenyl)-N-(2,6- difluorophenyl)-l,3-dimethyl-l H-pyrazol-5-amine, ( D015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6- fluorophenyl)- 1,3 -dimethyl- 1 H-pyrazol-5-amine, ( D025) N-( 4-chloro-2,6-difluorophenyl)-4-(2-chloro- 4-fluorophenyl)- 1,3 -dimethyl- lH-pyrazol-5 -amine,
(E003) captan, (E004) chlorothalonil, (E010) dithianon, (E012) folpet, (E013) mancozeb, (E015) metiram, (E018) propineb, (E020) thiram,
(L003) metalaxyl, (L004) metalaxyl-M (mefenoxam),
(M001) fludioxonil, (M002) iprodione, (M004) proquinazid, (M005) quinoxyfen,
(N001) fluazinam, (N002) meptyldinocap,
(0008) cyflufenamid, (15.010) cyprosulfamide, (O011) flutianil, (0012) fosetyl-aluminium, (15.016) metrafenone, (0022) Oxathiapiprolin, (0027) pyriofenone (chlazafenone), (0043) 2-{3-[2-(l-{[3,5- bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5- yl}-3-chlorophenyl methanesulfonate (fluoxapiprolin), (0047) 3-(4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinolin-l-yl)quinoline (Quinofumelin), (0048) 4-amino-5-fluoropyrimi din-2 -ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), (0052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4- amine, (0053) 5-fluoro-2-[ ( 4-methylbenzyl)oxy ]pyrimidin-4-amine, ( O 062) 5-fluoro-4-imino-3- methyl-l-[ ( 4-methylphenyl)sulfonyl]-3 ,4-dihydropyrimidin-2( 1 H)-one, (0063) pyridachlometyl, (0064) ipflufenoquin, (0065) aminopyrifen,
(P006) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide, (P104) N-methyl- 4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzenecarboxamide.
Further particularly most preferred compositions of compound (I) according to the invention comprise componenet (2) at least one further active compound selected from:
(AOOl)cyproconazole, (A002) difenoconazole, (A004) tetraconazol (A006) fenpropimorph, (A009) flutriafol, (A013) metconazole, (A017) propiconazole, (A018) prothioconazole, (A021) tebuconazole, (A022) epoxiconazole, (A081) mefentrifluconazole, (B001) benzovindiflupyr, (B002) bixafen, (B005) fluopyram, (B007) fluxapyroxad, (B019) pydiflumetofen, (B028) inpyrfluxam, (B30) fluindapyr, (B038) isoflucpyram, (C003) azoxystrobin, (C012) fluoxastrobin (C014) metominostrobin, (C017) pyraclostrobin, (C016) picoxystrobin, (C020) trifloxystrobin, (C025) (3S,6S,7R,8R)-8-benzyl-3-[({3- [(isobutyryloxy)methoxy] -4-methoxypyridin-2-yl } carbonyl)amino] -6-methyl-4,9-dioxo- 1 ,5-dioxonan-7 - yl-2-methylpropanoate (Fenpicoxamid), (C030) I -( 2- { [ I -(4-chlorophenyl )pyrazol-3-yl]oxymethyl }-3- methylphenyl)-l,4-dihydro-4-methyl-5H-tetrazol-5-one (Metyltetraprole), (D001) carbendazim, (D007) thiophanate-methyl, (E004) chlorothalonil, (E010) dithianon , (E013) mancozeb, (E020) thiram, (L003) metalaxyl, (M001) fludioxonil, (N001) fluazinam, (0022) Oxathiapiprolin, (0043) 2-{3-[2-(l-{ [3,5- bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5- yl}-3-chlorophenyl methanesulfonate (fluoxapiprolin), (0046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4- dihydroisoquinobn-l-yl)quinobne, (0047) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l- yl)quinoline (Quinofumelin), (0065) ipflufenoquin, (P006) N-(2,4-difluorophenyl)-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide and (P103) 5-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one.
The following combinations exemplify specific embodiments of the agrochemical composition according to the present invention.
Following combinations listed in Table-1, wherein componenet (1) (compound of formula (I), a group represented by the expression "(I)" comprising of compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, I- 11 , 1-12, 1-13, 1-14 and 1-15) and another component (2) selected from the groups A) to P) as defined herein (component 2, for example, (A001 or cyproconazole, in combination [(I)+(A001] )
Table-1:
(I)+(A001), (I)+(A002), (I)+(A003), (I)+(A004), (I)+(A005), (I)+(A006), (I)+(A007), (I)+(A008),
(I)+(A009), (I)+(A010), (I)+(A011), (I)+(A012), (I)+(A013), (I)+(A014), (I)+(A015), (I)+(A016),
(I)+(A017), (I)+(A018), (I)+(A019), (I)+(A020), (I)+(A021), (I)+(A022), (I)+(A023), (I)+(A024),
(I)+(A025), (I)+(A026), (I)+(A027), (I)+(A028), (I)+(A029), (I)+(A030), (I)+(A031), (I)+(A032),
(I)+(A033), (I)+(A034), (I)+(A035), (I)+(A036), (I)+(A037), (I)+(A038), (I)+(A039), (I)+(A040),
(I)+(A041), (I)+(A042), (I)+(A043), (I)+(A044), (I)+(A045), (I)+(A046), (I)+(A047), (I)+(A048),
(I)+(A049), (I)+(A050), (I)+(A051), (I)+(A052), (I)+(A053), (I)+(A054), (I)+(A055), (I)+(A056),
(I)+(A057), (I)+(A058), (I)+(A059), (I)+(A060), (I)+(A061), (I)+(A062), (I)+(A063), (I)+(A064),
(I)+(A065), (I)+(A066), (I)+(A067), (I)+(A068), (I)+(A069), (I)+(A070), (I)+(A071), (I)+(A072),
(I)+(A073), (I)+(A074), (I)+(A075), (I)+(A076), (I)+(A077), (I)+(A078), (I)+(A079), (I)+(A080),
(I)+(A081), (I)+(A082), (I)+(A083), (I)+(A084), (I)+(B001), (I)+(B002), (I)+(B003), (I)+(B004),
(I)+(B005), (I)+(B006), (I)+(B007), (I)+(B008), (I)+(B009), (I)+(B010), (I)+(B011), (I)+(B012),
(I)+(B013), (I)+(B014), (I)+(B015), (I)+(B016), (I)+(B017), (I)+(B018), (I)+(B019), (I)+(B020),
(I)+(B021), (I)+(B022), (I)+(B023), (I)+(B024), (I)+(B025), (I)+(B026), (I)+(B027), (I)+(B028),
(I)+(B029), (I)+(B030), (I)+(B031), (I)+(B032), (I)+(B033), (I)+(B034), (I)+(B035), (I)+(B036),
(I)+(B037), (I)+(B038), (I)+(B039), (I)+(B040), (I)+(B041), (I)+(B042), (I)+(B043), (I)+(B044),
(I)+(B045), (I)+(B046), (I)+(B047), (I)+(B048), (I)+(B049), (I)+(B050), (I)+(B051), (I)+(B052),
(I)+(B053), (I)+(B054), (I)+(B055), (I)+(B056), (I)+(B057), (I)+(B058), (I)+(B059), (I)+(B060),
(I)+(C001), (I)+(C002), (I)+(C003), (I)+(C004), (I)+(C005), (I)+(C006), (I)+(C007), (I)+(C008),
(I)+(C009), (I)+(C010), (I)+(C011), (I)+(C012), (I)+(C013), (I)+(C014), (I)+(C015), (I)+(C016),
(I)+(C017), (I)+(C018), (I)+(C019), (I)+(C020), (I)+(C021), (I)+(C022), (I)+(C023), (I)+(C024),
(I)+(C025), (I)+(C026), (I)+(C027), (I)+(C028), (I)+(C029), (I)+(C030), (I)+(D001), (I)+(D002),
(I)+(D003), (I)+(D004), (I)+(D005), (I)+(D006), (I)+(D007), (I)+(D008), (I)+(D009), (I)+(D010),
(I)+(D011), (I)+(D012), (I)+(D013), (I)+(D014), (I)+(D015), (I)+(D016), (I)+(D017), (I)+(D018),
(I)+(D019), (I)+(D020), (I)+(D021), (I)+(D022), (I)+(D023), (I)+(D024), (I)+(D025), (I)+(E001),
(I)+(E002), (I)+(E003), (I)+(E004), (I)+(E005), (I)+(E006), (I)+(E007), (I)+(E008), (I)+(E009),
(I)+(E010), (I)+(E011), (I)+(E012), (I)+(E013), (I)+(E014), (I)+(E015), (I)+(E016), (I)+(E017),
(I)+(E018), (I)+(E019), (I)+(E020), (I)+(E021), (I)+(E022), (I)+(E023), (I)+(F001), (I)+(F002),
(I)+(F003), (I)+(F004), (I)+(G001), (I)+(G002), (I)+(G003), (I)+(G004), (I)+(G005), (I)+(G006),
(I)+(H001), (I)+(I001), (I)+(I002), (I)+(I003), (I)+(I004), (I)+(I005), (I)+(I006), (I)+(I007), (I)+(I008),
(I)+(I009), (I)+(J001), (I)+(J002), (I)+(J003), (I)+(K001), (I)+(K002), (I)+(L001), (I)+(L002), (I)+(L003), (I)+(L004), (I)+(M001), (I)+(M002), (I)+(M003), (I)+(M004), (I)+(M005), (I)+(M006),
(I)+(N001), (I)+(N002), (I)+(O001), (I)+(O002), (I)+(O003), (I)+(O004), (I)+(O005), (I)+(O006),
(I)+(O007), (I)+(O008), (I)+(O009), (I)+(O010), (I)+(O011), (I)+(O012), (I)+(O013), (I)+(O014),
(I)+(O015), (I)+(O016), (I)+(O017), (I)+(O018), (I)+(O019), (I)+(O020), (I)+(O021), (I)+(O022),
(I)+(O023), (I)+(O024), (I)+(O025), (I)+(O026), (I)+(O027), (I)+(O028), (I)+(O029), (I)+(O030),
(I)+(O031), (I)+(O032), (I)+(O033), (I)+(O034), (I)+(O035), (I)+(O036), (I)+(O037), (I)+(O038),
(I)+(O039), (I)+(O040), (I)+(O041), (I)+(O042), (I)+(O043), (I)+(O044), (I)+(O045), (I)+(O046),
(I)+(O047), (I)+(O048), (I)+(O049), (I)+(O050), (I)+(O051), (I)+(O052), (I)+(O053), (I)+(O054),
(I)+(O055), (I)+(O056), (I)+(O057), (I)+(O058), (I)+(O059), (I)+(O060), (I)+(O061), (I)+(O062),
(I)+(O063), (I)+(O064), (I)+(O065), (I)+(P001), (I)+(P002), (I)+(P003), (I)+(P004), (I)+(P005), (I)+(P006), (I)+(P007), (I)+(P008), (I)+(P009), (I)+(P010), (I)+(P011), (I)+(P012), (I)+(P013),
(I)+(P014), (I)+(P015), (I)+(P016), (I)+(P017), (I)+(P018), (I)+(P019), (I)+(P020), (I)+(P021),
(I)+(P022), (I)+(P023), (I)+(P024), (I)+(P025), (I)+(P026), (I)+(P027), (I)+(P028), (I)+(P029),
(I)+(P030), (I)+(P031), (I)+(P032), (I)+(P033), (I)+(P034), (I)+(P035), (I)+(P036), (I)+(P037),
(I)+(P038), (I)+(P039), (I)+(P040), (I)+(P041), (I)+(P042), (I)+(P043), (I)+(P044), (I)+(P045),
(I)+(P046), (I)+(P047), (I)+(P048), (I)+(P049), (I)+(P050), (I)+(P051), (I)+(P052), (I)+(P053),
(I)+(P054), (I)+(P055), (I)+(P056), (I)+(P057), (I)+(P058), (I)+(P059), (I)+(P060), (I)+(P061),
(I)+(P062), (I)+(P063), (I)+(P064), (I)+(P065), (I)+(P066), (I)+(P067), (I)+(P068), (I)+(P069),
(I)+(P070), (I)+(P071), (I)+(P072), (I)+(P073), (I)+(P074), (I)+(P075), (I)+(P076), (I)+(P077),
(I)+(P078), (I)+(P079), (I)+(P080), (I)+(P081), (I)+(P082), (I)+(P083), (I)+(P084), (I)+(P085),
(I)+(P086), (I)+(P087), (I)+(P088), (I)+(P089), (I)+(P090), (I)+(P091), (I)+(P092), (I)+(P093),
(I)+(P094), (I)+(P095), (I)+(P096), (I)+(P097), (I)+(P098), (I)+(P099), (I)+(P100), (I)+(P101),
(I)+(P102), (I)+(P103), (I)+(P104), (I)+(Q001), (I)+(Q002).
In one embodiment the weight ratio of componenet (1) to component (2) is between 100:1 and 1:100 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
In one embodiment the weight ratio of componenet (1) to component (2) is between 50:1 and 1:50 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
In one embodiment the weight ratio of componenet (1) to component (2) is between 20:1 and 1:20 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
In one embodiment the weight ratio of componenet (1) to component (2) is between 5:1 and 1:5 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
In one embodiment the weight ratio of componenet (1) to component (2) is between 3:1 and 1:3 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
In one embodiment the weight ratio of componenet (1) to component (2) is 1:1 in combinations [(I) + (A001] to [(I) + (Q002)] of Table: 1.
Particularly, following combinations listed in Table-2, wherein component (1) as compound (1-1) and component (2) selected from the groups A) to P) as defined
Table-2 (I-1)+(A001), (I-1)+(A002), (I-1)+(A003), (I-1)+(A004), (I-1)+(A005), (I-1)+(A006), (I-1)+(A007), (I- 1)+(A008), (I-1)+(A009), (I-1)+(A010), (I-1)+(A011), (I-1)+(A012), (I-1)+(A013), (I-1)+(A014), (I-
1)+(A015), (I-1)+(A016), (I-1)+(A017), (I-1)+(A018), (I-1)+(A019), (I-1)+(A020), (I-1)+(A021), (I-
1)+(A022), (I-1)+(A023), (I-1)+(A024), (I-1)+(A025), (I-1)+(A026), (I-1)+(A027), (I-1)+(A028), (I-
1)+(A029), (I-1)+(A030), (I-1)+(A031), (I-1)+(A032), (I-1)+(A033), (I-1)+(A034), (I-1)+(A035), (I-
1)+(A036), (I-1)+(A037), (I-1)+(A038), (I-1)+(A039), (I-1)+(A040), (I-1)+(A041), (I-1)+(A042), (I-
1)+(A043), (I-1)+(A044), (I-1)+(A045), (I-1)+(A046), (I-1)+(A047), (I-1)+(A048), (I-1)+(A049), (I-
1)+(A050), (I-1)+(A051), (I-1)+(A052), (I-1)+(A053), (I-1)+(A054), (I-1)+(A055), (I-1)+(A056), (I-
1)+(A057), (I-1)+(A058), (I-1)+(A059), (I-1)+(A060), (I-1)+(A061), (I-1)+(A062), (I-1)+(A063), (I-
1)+(A064), (I-1)+(A065), (I-1)+(A066), (I-1)+(A067), (I-1)+(A068), (I-1)+(A069), (I-1)+(A070), (I-
1)+(A071), (I-1)+(A072), (I-1)+(A073), (I-1)+(A074), (I-1)+(A075), (I-1)+(A076), (I-1)+(A077), (I-
1)+(A078), (I-1)+(A079), (I-1)+(A080), (I-1)+(A081), (I-1)+(A082), (I-1)+(A083), (I-1)+(A084), (I-
1)+(B001), (I-1)+(B002), (I-1)+(B003), (I-1)+(B004), (I-1)+(B005), (I-1)+(B006), (I-1)+(B007), (I-
1)+(B008), (I-1)+(B009), (I-1)+(B010), (I-1)+(B011), (I-1)+(B012), (I-1)+(B013), (I-1)+(B014), (I-
1)+(B015), (I-1)+(B016), (I-1)+(B017), (I-1)+(B018), (I-1)+(B019), (I-1)+(B020), (I-1)+(B021), (I-
1)+(B022), (I-1)+(B023), (I-1)+(B024), (I-1)+(B025), (I-1)+(B026), (I-1)+(B027), (I-1)+(B028), (I-
1)+(B029), (I-1)+(B030), (I-1)+(B031), (I-1)+(B032), (I-1)+(B033), (I-1)+(B034), (I-1)+(B035), (I-
1)+(B036), (I-1)+(B037), (I-1)+(B038), (I-1)+(B039), (I-1)+(B040), (I-1)+(B041), (I-1)+(B042), (I-
1)+(B043), (I-1)+(B044), (I-1)+(B045), (I-1)+(B046), (I-1)+(B047), (I-1)+(B048), (I-1)+(B049), (I-
1)+(B050), (I-1)+(B051), (I-1)+(B052), (I-1)+(B053), (I-1)+(B054), (I-1)+(B055), (I-1)+(B056), (I-
1)+(B057), (I-1)+(C001), (I-1)+(C002), (I-1)+(C003), (I-1)+(C004), (I-1)+(C005), (I-1)+(C006), (I-
1)+(C007), (I-1)+(C008), (I-1)+(C009), (I-1)+(C010), (I-1)+(C011), (I-1)+(C012), (I-1)+(C013), (I-
1)+(C014), (I-1)+(C015), (I-1)+(C016), (I-1)+(C017), (I-1)+(C018), (I-1)+(C019), (I-1)+(C020), (I-
1)+(C021), (I-1)+(C022), (I-1)+(C023), (I-1)+(C024), (I-1)+(C025), (I-1)+(C026), (I-1)+(C027), (I-
1)+(C028), (I-1)+(C029), (I-1)+(C030), (I-1)+(D001), (I-1)+(D002), (I-1)+(D003), (I-1)+(D004), (I-
1)+(D005), (I-1)+(D006), (I-1)+(D007), (I-1)+(D008), (I-1)+(D009), (I-1)+(D010), (I-1)+(D011), (I-
1)+(D012), (I-1)+(D013), (I-1)+(D014), (I-1)+(D015), (I-1)+(D016), (I-1)+(D017), (I-1)+(D018), (I-
1)+(D019), (I-1)+(D020), (I-1)+(D021), (I-1)+(D022), (I-1)+(D023), (I-1)+(D024), (I-1)+(D025), (I-
1)+(E001), (I-1)+(E002), (I-1)+(E003), (I-1)+(E004), (I-1)+(E005), (I-1)+(E006), (I-1)+(E007), (I-
1)+(E008), (I-1)+(E009), (I-1)+(E010), (I-1)+(E011), (I-1)+(E012), (I-1)+(E013), (I-1)+(E014), (I-
1)+(E015), (I-1)+(E016), (I-1)+(E017), (I-1)+(E018), (I-1)+(E019), (I-1)+(E020), (I-1)+(E021), (I-
1)+(E022), (I-1)+(E023), (I-1)+(F001), (I-1)+(F002), (I-1)+(F003), (I-1)+(F004), (I-1)+(G001), (I-
1)+(G002), (I-1)+(G003), (I-1)+(G004), (I-1)+(G005), (I-1)+(G006), (I-1)+(H001), (I-1)+(I001), (I- 1)+(I002), (I-1)+(I003), (I-1)+(I004), (I-1)+(I005), (I-1)+(I006), (I-1)+(I007), (I-1)+(I008), (I-1)+(I009), (I-1)+(J001), (I-1)+(J002), (I-1)+(J003), (I-1)+(K001), (I-1)+(K002), (I-1)+(L001), (I-1)+(L002), (I- 1)+(L003), (I-1)+(L004), (I-1)+(M001), (I-1)+(M002), (I-1)+(M003), (I-1)+(M004), (I-1)+(M005), (I-
1)+(M006), (I-1)+(N001), (I-1)+(N002), (I-l)+(0001), (I-l)+(0002), (I-l)+(0003), (I-l)+(0004), (I- l)+(O005), (I-l)+(O006), (I-l)+(O007), (I-l)+(0008), (I-l)+(0009), (I-l)+(0010), (I-l)+(O011), (I- l)+(O012), (I-l)+(O013), (I-l)+(O014), (I-l)+(O015), (I-l)+(O016), (I-l)+(O017), (I-l)+(O018), (I- l)+(O019), (I-l)+(O020), (I-l)+(O021), (I-l)+(O022), (I-l)+(O023), (I-l)+(O024), (I-l)+(O025), (I- l)+(O026), (I-l)+(O027), (I-l)+(O028), (I-l)+(O029), (I-l)+(0030), (I-l)+(O031), (I-l)+(O032), (I- l)+(O033), (I-l)+(O034), (I-l)+(O035), (I-l)+(O036), (I-l)+(O037), (I-l)+(O038), (I-l)+(O039), (I- l)+(O040), (I-l)+(O041), (I-l)+(O042), (I-l)+(O043), (I-l)+(O044), (I-l)+(O045), (I-l)+(O046), (I- l)+(O047), (I-l)+(O048), (I-l)+(O049), (I-l)+(0050), (I-l)+(O051), (I-l)+(O052), (I-l)+(O053), (I- l)+(O054), (I-l)+(O055), (I-l)+(O056), (I-l)+(O057), (I-l)+(O058), (I-l)+(O059), (I-l)+(O060), (I- l)+(O061), (I-l)+(O062), (I-l)+(O063), (I-l)+(O064), (I-l)+(O065), (I-1)+(P001), (I-1)+(P002), (I- 1)+(P003), (I-1)+(P004), (I-1)+(P005), (I-1)+(P006), (I-1)+(P007), (I-1)+(P008), (I-1)+(P009), (I-
1)+(P010), (I-1)+(P011), (I-1)+(P012), (I-1)+(P013), (I-1)+(P014), (I-1)+(P015), (I-1)+(P016), (I-
1)+(P017), (I-1)+(P018), (I-1)+(P019), (I-1)+(P020), (I-1)+(P021), (I-1)+(P022), (I-1)+(P023), (I-
1)+(P024), (I-1)+(P025), (I-1)+(P026), (I-1)+(P027), (I-1)+(P028), (I-1)+(P029), (I-1)+(P030), (I-
1)+(P031), (I-1)+(P032), (I-1)+(P033), (I-1)+(P034), (I-1)+(P035), (I-1)+(P036), (I-1)+(P037), (I-
1)+(P038), (I-1)+(P039), (I-1)+(P040), (I-1)+(P041), (I-1)+(P042), (I-1)+(P043), (I-1)+(P044), (I-
1)+(P045), (I-1)+(P046), (I-1)+(P047), (I-1)+(P048), (I-1)+(P049), (I-1)+(P050), (I-1)+(P051), (I-
1)+(P052), (I-1)+(P053), (I-1)+(P054), (I-1)+(P055), (I-1)+(P056), (I-1)+(P057), (I-1)+(P058), (I-
1)+(P059), (I-1)+(P060), (I-1)+(P061), (I-1)+(P062), (I-1)+(P063), (I-1)+(P064), (I-1)+(P065), (I-
1)+(P066), (I-1)+(P067), (I-1)+(P068), (I-1)+(P069), (I-1)+(P070), (I-1)+(P071), (I-1)+(P072), (I-
1)+(P073), (I-1)+(P074), (I-1)+(P075), (I-1)+(P076), (I-1)+(P077), (I-1)+(P078), (I-1)+(P079), (I-
1)+(P080), (I-1)+(P081), (I-1)+(P082), (I-1)+(P083), (I-1)+(P084), (I-1)+(P085), (I-1)+(P086), (I-
1)+(P087), (I-1)+(P088), (I-1)+(P089), (I-1)+(P090), (I-1)+(P091), (I-1)+(P092), (I-1)+(P093), (I-
1)+(P094), (I-1)+(P095), (I-1)+(P096), (I-1)+(P097), (I-1)+(P098), (I-1)+(P099), (I-1)+(P100), (I-
1)+(P101), (I-1)+(P102), (I-1)+(P103), (I-1)+(P104), (I-1)+(Q001), (I-1)+(Q002).
Table 3:
Combination [(1-2) + (A001] to [(1-2) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-2).
Table 4:
Combination [(1-3) + (A001] to [(1-3) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-3).
Table 5:
Combination [(1-4) + (A001] to [(1-4) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-4).
Table 6:
Combination [(1-5) + (A001] to [(1-5) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-5).
Table 7:
Combination [(1-6) + (A001] to [(1-6) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-6).
Table 8:
Combination [(1-7) + (A001] to [(1-7) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-7).
Table 9: Combination [(1-8) + (A001] to [(1-7) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-8).
Table 10:
Combination [(1-9) + (A001] to [(1-9) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-9).
Table 11:
Combination [(TIO) + (A001] to [(1-10) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-10).
Table 12:
Combination [(Til) + (A001] to [(Til) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-11).
Table 13:
Combination [(1-12) + (A001] to [(T12) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T12).
Table 14:
Combination [(T13) + (A001] to [(T13) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T13).
Table 15:
Combination [(1-14) + (A001] to [(1-14) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (1-14).
Table 16:
Combination [(T15) + (A001] to [(T15) + (Q002)] are defined as combination [(1-1) + (A001] to [(1-1) + (Q002)] of Table 2, wherein compound (1-1) in each mixture is replaced with compound (T15).
In one embodiment, the present invention provides use of the fungicidal composition for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi.
In a preferred embodiment, the compositions disclosed in table- 1 to table- 16 and in particular when the weight ratios of componenet (1) to componenet (2) are as disclosed for these mixtures as herein mentioned before, are used against crop phytopathogenic fungi like Alternaria species, for example Alternaria solanr, Erysiphe spp. (e.g. Erysiphe cichoracearum ); Pyricularia species, for example Pyricularia oryzae Septoria species, for example Septoria nodorum, Puccinia spp. (rusts) on various plants, in particular P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust), on cereals selected from wheat, barley or rye, P. coronata (crown rust of grasses including oats) on cereals, such as e. g. wheat, barley or rye, and Puccinia sorghi (common rust) on maize, Puccinia polysora (southern rust) on maize, and P. helianthi (sunflower rust); Puccinia melanocephala ('Brown rust' in sugarcane); Hemileia vastatrix and Hemileia cojfeicola (leaf rust and grey rust of coffee) Hemileia vastatrix (Coffee rust); Uromyces spp. on various crops; and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
The novel agrochemical compositions according to the invention have a potent microbicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases). More specifically, the agrochemical composition according to the invention can be used to protect seeds, germinating plants, emerged seedlings, plants, plant parts, fruits and the soil in which the plants grow from unwanted microorganisms.
The term “Control” or “Controlling” as used herein encompasses curative and protective treatment of unwanted microorganisms. The unwanted microorganisms may be pathogenic bacteria or pathogenic fungi, more specifically phytopathogenic bacteria or phytopathogenic fungi. As detailed herein below, these phytopathogenic microorganims are the causal agents of a broad spectrum of plants diseases.
More specifically, novel agrochemical composition according to the invention can be used as fungicides. In particular, they can be useful in crop protection, for example for the control of unwanted fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
The novel agrochemical composition according to the invention can also be used as bactericide. In particular, they can be used in crop protection, for example for the control of unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae , Corynebacteriaceae and Streptomycetaceae .
In one embodiment, the present invention provides a method for controlling or preventing infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein the fungicidal composition is applied to the plants, to parts thereof or to a locus thereof.
In another embodiment, the present invention provides a method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with the fungicidal composition as described herein.
The present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, comprising the step of applying at least one novel agrochemical composition according to the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
Typically, when the novel agrochemical composition according to the invention are used in curative or protective methods for controlling phytopathogenic fungi, an effective and non-phytotoxic amount thereof is applied to the plants, plant parts, fruits, seeds or to the soil in which the plants grow.
Effective and non-phytotoxic amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the respective composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.
The novel agrochemical composition according to the invention can be applied to any plants or plant parts.
In one embodiment, the present invention provides a fungicidal composition for treating seed, seed of transgenic plants and transgenic plants.
Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders' rights.
Genetically modified plants (GMO or transgenic plants) are plants of which a heterologous gene has been stably integrated into the genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome. This gene gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression teclmology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
Plants which can be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Ivloraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Afusaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and tiiticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis ; Podosphaera species, for example Podosphaera leucotricha Sphaerotheca species, for example Sphaerotheca fuliginea Uncinula species, for example Uncinula necator Erysiphe species, for example Erysiphe cichoracearu diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae Hemileia species, for example Hemileia vastatrix Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae ; Puccinia species, for example Puccinia recondita, Puccinia graminis or Puccinia striiformis,and and Puccinia melanocephala Uromyces species, for example Uromyces appendiculatus
In particular, Cronartium ribicola (White pine blister rust); Gymnosporangium juniperi-virginianae (Cedar-apple rust); Hemileia vastatrix (Coffee rust); Phakopsora meibomiae and P. pachyrhizi (Soybean rust); Puccinia coronata (Crown Rust of Oats and Ryegrass); Puccinia graminis (Stem rust of wheat and Kentucky bluegrass, or black rust of cereals); Puccinia hemerocallidis (Daylily rust); Puccinia persistens subsp. triticina (wheat rust or 'brown or red rust'); Puccinia sorghi (rust in corn); Puccinia striiformis ('Yellow rust' in cereals); Puccinia melanocephala; Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust); Puccinia melanocephala ('Brown rust' in sugarcane); Puccinia kuehnii ('Orange rust' in sugarcane). diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Peronospora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochium nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum Fusarium species, for example Fusarium oxysporum Gaeumannomyces species, for example Gaeumannomyces graminis ; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae Sclerotium species, for example Sclerotium oryzae Tapesia species, for example Tapesia acuformis Thielaviopsis species, for example Thielaviopsis basicola; Ganoderma species, for example Ganoderma lucidum ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Alternaria spp. Aspergillus species, for example Aspergillus flavus Cladosporium species, for example Cladosporium cladosporioides Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum or Penicillium purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticilium species, for example Verticilium alboatrum; seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lends; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, for example Penicillium expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii Septoria species, for example Septoria nodorum Typhula species, for example Typhula incarnata Verticillium species, for example Verticillium dahliae cancers, galls and witches’ broom caused, for example, by Nectria species, for example Nectria galligena wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans Taphrina species, for example Taphrina deformans ; degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranean Ganoderma species, for example Ganoderma boninensen diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solanv, Helminthosporium species, for example Helminthosporium solanv, diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzaen Pseudomonas species, for example Pseudomonas syringae pv. lachrymans, Erwinia species, for example Erwinia amylovoran Ralstonia species, for example Ralstonia solanacearumn
Fungal diseases on roots and the stem base caused, for example, by black root rot ( Calonectria crotalariae), charcoal rot ( Macrophomina phaseolina ), fusarium blight or wilt, root rot, and pod and collar rot ( Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti ), mycoleptodiscus root rot ( Mycoleptodiscus terrestris ), neocosmospora ( Neocosmospora vasinfecta ), pod and stem blight ( Diaporthe phaseolorum), stem canker ( Diaporthe phaseolorum var. caulivora ), phytophthora rot ( Phytophthora megaspermci), brown stem rot ( Phialophora gregatd), pythium rot ( Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off ( Rhizoctonia solani ), sclerotinia stem decay ( Sclerotinia sclerotiorum), sclerotinia southern blight ( Sclerotinia rolfsii), thielaviopsis root rot ( Thielaviopsis basicold).
Plants which can be treated in accordance with the invention include the following: Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Poaceae/Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
More preference is given to controlling the following diseases of soya beans: Fungal diseases on leaves, stems, pods and seeds caused, for example, by Altemaria leaf spot ( Altemaria spec atrans tenuissima ), Anthracnose ( Colletotrichum gloeosporoides dematium var. truncatum), brown spot ( Septoria glycines ), cercospora leaf spot and blight ( Cercospora kikuchii ), choanephora leaf blight ( Choanephora infundibulifera trispora (Syn.J), dactuliophora leaf spot ( Dactuliophora glycines), downy mildew ( Peronospora manshurica ), drechslera blight ( Drechslera glycini), frogeye leaf spot ( Cercospora sojina), leptosphaerulina leaf spot ( Leptosphaerulina trifolu), phyllostica leaf spot ( Phyllosticta sojaecola), pod and stem blight ( Phomopsis sojae), powdery mildew ( Microsphaera diffusa), pyrenochaeta leaf spot ( Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight ( Rhizoctonia solani), rust ( Phakopsora pachyrhizi, Phakopsora meibomiae), scab ( Sphaceloma glycines), stemphylium leaf blight ( Stemphylium botryosum), target spot ( Corynespora cassiicola).
The agrochemical compositions of the present invention can be used for curative or protective/preventive control of phytopathogenic fungi. The present invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the novel agrochemical compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.
The fact that the novel agrochemical compositions according to the invention are well tolerated by plants at the concentrations required for controlling plant diseases allows the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
According to the invention all plants and plant parts can be treated. By plants is meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights). Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods. By plant parts is meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, conns and rhizomes are listed. Crops and vegetative and generative propagating material, for example cuttings, conns, rhizomes, runners and seeds also belong to plant parts.
The novel agrochemical compositions according to the invention, when they are well tolerated by plants, have favorable homeotherm toxicity and are well tolerated by the environment, are suitable for protecting plants and plant organs, for enhancing harvest yields, for improving the quality of the harvested material. They can preferably be used as crop protection compositions. They are active against normally sensitive and resistant species and against all or some stages of development.
Plants which can be treated in accordance with the invention include the following main crop plants: maize, soya bean, alfalfa, cotton, sunflower, Brassica oil seeds such as Brassica napus (e.g. canola, rapeseed), Brassica rapa, B.juncea (e.g. (field) mustard) and Brassica carinata, Arecaceae sp. (e.g. oilpalm, coconut), rice, wheat, sugar beet, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, nuts, grapes and vine and vaiious fruit and vegetables from various botanic taxa, e.g. Rosaceae sp. (e.g. pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds, plums and peaches, and berry fruits such as strawberries, raspberries, red and black currant and gooseberry), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Aforaceae sp., Oleaceae sp. (e.g. olive tree), Actinidaceae sp., Lauraceae sp. (e.g. avocado, cinnamon, camphor), Afusaceae sp. (e.g. banana trees and plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp. (e.g. tea), Sterculiceae sp., Rutaceae sp. (e.g. lemons, oranges, mandarins and grapefruit); Solanaceae sp. (e.g. tomatoes, potatoes, peppers, capsicum, aubergines, tobacco), Liliaceae sp., Compositae sp. (e.g. lettuce, artichokes and chicory - including root chicmy, endive or common chicory), Umbelliferae sp. (e.g. carrots, parsley, celery and celeriac), Cucurbitaceae sp. (e.g. cucumbers - including gherkins, pumpkins, watermelons, calabashes and melons), Alliaceae sp. (e.g. leeks and onions), Cruciferae sp. (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage), Leguminosae sp. (e.g. peanuts, peas, lentils and beans - e.g. common beans and broad beans), Chenopodiaceae sp. (e.g. Swiss chard, fodder beet, spinach, beetroot), Linaceae sp. (e.g. hemp), Cannabeacea sp. (e.g. cannabis), Malvaceae sp. (e.g. okra, cocoa), Papaveraceae (e.g. poppy), Asparagaceae (e.g. asparagus); useful plants and ornamental plants in the garden and woods including turf, lawn, grass and Stevia rebaudiana; and in each case genetically modified types of these plants. In particular, the novel agrochemical compositions according to the invention are suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A Candida ) and sunflowers (e. g. A tragopogonis); Alternaria spp.(Alternaria leaf spot) on vegetables, rape (A brassicola or brassi cae), 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. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma ) spp. (rot or wilt) on broad leaved trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeaemaydis), rice, sugar beets (e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) 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: Helmin thosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana) and rice (e.g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypit), corn (e.g. C. gramini cola: Anthracnose stalk rot), fruits, potatoes (e.g. C. coccodes: black dot), vegetables like beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum or C. gloeosporioides); Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e.g. C. oleaginum on olive trees; Cylindrocarpon spp. (e.g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e.g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, net blotch) and wheat (e.g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyn), soft fruits (E. veneta: anthracnose) and vines (E.ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pist), such as cucurbits (e.g. E. cichoracearum), cabbages, rape (e.g. E. crucifer arum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicu ) Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e.g. wheat or barley) and corn; Gib berella spp. on cereals (e. g. G. z.eae ) and rice (e.g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining com plex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoft) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M. laxa, M. fructicola and M. fructigena(b\oom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M.fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae), rape (e.g. P. parasitica), onions (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. on vines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e.g. P. capsid ), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad leaved trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root)on cabbage, rape, radish and other plants; Plasmopara spp., e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosa ceous plants, hop, pome and soft fruits, e.g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such as barley and wheat (P. graminis ) and sugar beets (P. betae ) and thereby trans mitted viral diseases ; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or, rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum ); Ramu/aria spp., e. g. R. collo- cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sa rocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soy beans (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) no dorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucken) on vines; Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum ) and turf; Sphacelotheca spp. (smut) on corn, (e.g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto sphaeria [syn. Phaeosphaeria] nodorum ) on wheat; Synchytrium endobioticum on potatoes (po tato 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. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incamata (grey snow mold) on barley or wheat; Urocystis spp., e.g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e.g. U. appendiculatus, syn. U. phaseoft) and sugar beets (e.g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), com (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.
The present invention is also directed to the use of the novel agrochemical composition according to the invention for the treatment of soybean diseases.
Most preference is given to the following soybean diseases:
Cercospora kikuchii, Cercospora sojina; Colletotrichum gloeosporoides dematium var. truncatum; Corynespora casiicola; Diaporthe phaseolorum; Microsphaera diffusa; Peronospora manshurica;
Phakopsora species, for example Phakopsora pachyrhizi and Phakopsora meibomiae ( soybean rust); Phytophthora megasperma; Phialophora gregata; Rhizoctonia solani; Sclerotinia sclerotiorum; Septoria spp. e.g. Septoria glycines, Thielaviopsis basicola.
In addition, the novel agrochemical composition of the invention can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom. Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F. acuminatum, F. asiaticum, F. avenaceum, F croobvellense, F culmorum, F graminearum ( Gibberella zeae), F equiseti, F fujikoroi, F musarum, F oxysporum, F proliferatum, F poae, F pseudograminearum, F. sambucinum, F. scirpi, F semitectum, F solani, F sporotrichoides, F langsethiae, F. subglutinans, F. tricinctum, F verticillioides etc., and also by Aspergillus spec., such as A. jlavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotlys spec and others.
The novel agrochemical composition of the invention can also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by phytopathogenic fungi.
The novel agrochemical composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
In the case of treatment of wood, the novel agrochemical composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
The novel agrochemical composition of the invention can also be employed for protecting storage goods. Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timberr
Storage goods of animal origin are, for example, hides, leather, furs and hairs. The agrochemical composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The agrochemical composition of the invention preferably acts against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Nfucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.
The novel agrochemical composition of the invention can, at particular concentrations or application rates, also be used to improve plant properties, or as microbicides, for example as bactericides, viricides (including compositions against viroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).
The novel agrochemical composition of the invention may intervene in physiological processes of plants and can therefore also be used as plant growth regulators.
Growth regulating effects, comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kernels/ear, number of ears/m2 , number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyllotaxy, earlier maturation / earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fmit/vegetable size, sprouting resistance and reduced lodging.
Increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight as well as to improved product quality, comprising: improved processability relating to size distribution (kernel, fruit, etc.), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaption to cooking and frying; improved marketability relating to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased storage/ shelf-life, firmness/ softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour, etc.; increased desired ingredients such as e.g. protein content, fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste, etc.; decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxines, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content etc.
The novel agrochemical composition of the invention also exhibits a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
Plant-strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.
Further, in context with the present invention plant physiology effects comprise the following:
Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.
Biotic stress tolerance, comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria. In context with the present invention, biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.
Increased plant vigor, comprising plant health / plant quality and seed vigor, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects, etc.) and improved photosynthetic efficiency. The invention further comprises a method for treating seed. The invention further provides seed which has been treated by one of the methods described in the previous paragraph. The inventive seeds are employed in methods for the protection of seed from unwanted microorganisms. In these methods, seed treated with at least one inventive agrochemical composition is used.
The novel agrochemical composition of the present invention is also suitable for treating seed. A large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seed during storage or after sowing, and also during and after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even minor damage may result in the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using appropriate compositions.
The control of phytopathogenic fungi by treating the seed of plants has been known for a long time and is the subject of constant improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. For instance, it is desirable to develop methods for protecting the seed and the germinating plant, which dispense with, or at least significantly reduce, the additional deployment of crop protection compositions after planting or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used so as to provide the best possible protection for the seed and the germinating plant from attack by phytopathogenic fungi, but without damaging the plant itself by the active ingredient employed. In particular, methods for the treatment of seed should also take account of the intrinsic fungicidal properties of transgenic plants in order to achieve optimal protection of the seed and the germinating plant with a minimum expenditure of crop protection compositions.
In one embodiment, the present invention provides a seed comprising the fungicidal composition.
The present invention therefore also relates to a method for protection of seed and germinating plants from attack by phytopathogenic fungi, by treating the seed with an inventive composition. The invention likewise relates to the use of the inventive compositions for treatment of seed to protect the seed and the germinating plant from phytopathogenic fungi. The invention further relates to seed which has been treated with an inventive composition for protection from phytopathogenic fungi.
The control of phytopathogenic fungi which damage plants post-emergence is affected primarily by treating the soil and the above-ground parts of plants with crop protection compositions. Owing to the concerns regarding a possible influence of the crop protection compositions on the environment and the health of humans and animals, there are efforts to reduce the amount of active ingredients deployed.
One of the advantages of the present invention is that the particular systemic properties of the novel agrochemical composition not only protect the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
It is likewise considered to be advantageous that the novel agrochemical composition can especially also be used with transgenic seed, in which case the plant growing from this seed is capable of expressing a protein which acts against pests. By virtue of the treatment of such seed with the novel agrochemical compositions, merely the expression of the protein, for example an insecticidal protein, can control certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests.
The novel agrochemical compositions are suitable for protecting seeds of any plant variety which is used in agriculture, in greenhouses, in forests or in horticulture and viticulture. In particular, seeds of cereals (such as wheat, barley, rye, triticale, sorghm/millet and oats), maize, cotton, soyabean, rice, potato, sunflower, bean, coffee, beet (for example sugar beet and fodder beet), peanut, oilseed rape, poppy, olive, coconut, cocoa, sugar cane, tobacco, vegetables (such as tomato, cucumbers, onions and lettuce), turf and ornamentals (see also below). The treatment of seeds of cereals (such as wheat, barley, rye, triticale and oats), maize and rice is of particular significance.
As also described herein, the treatment of transgenic seed with the novel agrochemical composition is of particular significance. This relates to the seed of plants containing at least one heterologous gene which enables the expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. This heterologous gene preferably originates from Bacillus sp., in which case the gene product is effective against the european maize borer and/or the western maize rootworm. The heterologous gene more preferably originates from Bacillus thuringiensis.
In the context of the present invention, the novel agrochemical composition is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15 % by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.
When treating the seed, care must generally be taken that the amount of the novel agrochemical composition applied to the seed and/or the amount of further additives is selected such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This has to be borne in mind in particular in the case of active ingredients which can have phytotoxic effects at certain application rates.
The present invention further relates to a novel agrochemical composition, for controlling unwanted microorganisms. The agrochemical compositions may be applied to the microorganisms and/or in their habitat.
The agrochemical composition typically comprises at least one active compounds combination and at least one agriculturally suitable auxiliary, e.g. carrier(s) and/or surfactant(s).
In the context of the present invention, "control of harmful microorganisms" means a reduction in infestation by harmful microorganisms, compared with the untreated plant measured as fungicidal efficacy, preferably a reduction by 25-50 %, compared with the untreated plant (100 %), more preferably a reduction by 40-79 %, compared with the untreated plant (100 %); even more preferably, the infection by harmful microorganisms is entirely suppressed (by 70-100 %). The control may be curative, i.e. for treatment of already infected plants, or protective, for protection of plants which have not yet been infected.
An "effective but non-phytotoxic amount" means an amount of the novel agrochemical composition which is sufficient to control the fungal disease of the plant in a satisfactory manner or to eradicate the fungal disease completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions.
A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the application of the compounds, for instance, to plants, plants parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates. Examples of typically useful solid earners forpreparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N- alkylpynolidones) and lactones, sulphones and sulphoxides (such as dimethyl sulphoxide). The carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
The surfactant can be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s) and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylmyl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulphates, sulphonates, phosphates (for example, alkylsulphonates, alkyl sulphates, arylsulphonates) and protein hydrolysates, lignosulphite waste liquors and methylcellulose. A surfactant is typically used when the compoundof the formula (I) and/or the carrier is insoluble in water and the application is made with water. Then, the amount of surfactants typically ranges from 5 to 40 % by weight of the composition.
Further examples of suitable auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g. cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability), dyes or pigments (such as inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g. silicone antifoams and magnesium stearate), preservatives (e.g. dichlorophene and benzyl alcohol hemiformal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica), stickers, gibberellins and processing auxiliaries, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.
The choice of the auxiliaries is related to the intended mode of application of the compound of formula (I) and/or on the physical properties. Furthermore, the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the compositions or use forms prepared therefrom. The choice of auxiliaries may allow customizing the compositions to specific needs.
The novel agrochemical composition of the present invention may be in any customary form, such as solutions (e.g aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the agrochemical composition, fertilizers and also microencapsulations in polymeric substances. The agrochemical composition according to the invention may be present in a suspended, emulsified or dissolved form.
The novel agrochemical composition of the invention may be provided to the end user as ready-for-use formulation, i.e. the compositions can be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device. Alternatively, the compositions may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.
The novel agrochemical composition of the invention can be prepared in conventional manners, for example by mixing the agrochemical composition according to the invention with one or more suitable auxiliaries, such as disclosed herein above.
The novel agrochemical composition according to the invention contains generally from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 10 to 70 % by weight of the active compounds according to the invention.
The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 L/ha, especially from 10 to 1000 L/ha.
The novel agrochemical composition can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the composition to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 Al, WO 2002/080675, WO 2002/028186.
The novel agrochemical composition usable in accordance with the invention can be converted to the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
These formulations are prepared in a known manner, by mixing the active compounds with customary additives, for example customary extenders and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1. Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Preference is given to using alkyl naphthalenesulphonates, such as diisopropyl or diisobutyl naphthalenesulphonates .
Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.
Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
The gibberellins which may be present in the seed dressing formulations usable in accordance with the invention may preferably be gibberellins Al, A3 (= gibberellic acid), A4 and A7; particular preference is given to using gibberellic acid.
The seed dressing formulations usable in accordance with the invention can be used, either directly or after previously having been diluted with water, for the treatment of a wide range of different seed, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.
For treatment of seed with the seed dressing formulations usable in accordance with the invention, or the preparations prepared therefrom by adding water, all mixing units usable customarily for the seed dressing are useful. Specifically, the procedure in the seed dressing is to place the seed into a mixer, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying process.
In the novel agrochemical composition according to the invention the components (1) and components (2) are advantageously present in a synergistically effective weight ratio of components (l):components (2) in a range of 100:1 to 1:100, preferably in a weight ratio of 50:1 to 1:50, more preferably in a weight ratio of 20:1 to 1:20, even more preferably in a weight ratio of 10:1 to 1:10.
Further ratios by weight of components (l):components (2) which are preferably used within the weight ratio of 10:1 to 1:10 are 5: 1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2 and 1:1.
In particular, the novel agrochemical composition is used for foliar application.
According to the invention, the expression "composition" stands for the various mixtures or combinations of components (1) and (2), for example in a single "ready -mix" form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a "tank- mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. Preferably the order of applying the components (1) and (2) is not essential for working the present invention.
According to the invention the term "agrochemical composition" means a combination or mixture of at least two active compounds with further agriculturally suitable additives, such as agriculturally suitable auxiliaries, e.g. solvents, carriers, surfactants, extenders or the like which are described above. The term "agrochemical composition" also comprises the terms "crop protection composition" and "formulation".
When using the novel agrochemical composition as a fungicide, the application rates can be varied within a relatively wide range, depending on the kind of application. The application rate in the case of treatment of plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used); in the case of seed treatment: from 2 to 200 g per 100 kg of seed, in the case of soil treatment: from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.
These application rates are merely by way of example and are not limiting for the purposes of the invention.
The user may apply the novel agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
Consequently, one embodiment of the invention is a kit for preparing a usable agrochemical composition, the kit comprising a) a composition comprising component (1) as defined herein and at least one auxiliary; and b) a composition comprising component (2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component (3) as defined herein.
The present invention furthermore relates to a agrochemical compositions comprising a mixture of at least one compound of formula (I) (component 1) and at least one further active compound useful for plant protection, e. g. selected from the groups A) to P) (component 2) as described above, and if desired one suitable solvent or solid carrier. These mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi.
Furthermore, combating harmful fungi with a mixture of a compound of formula (I) and at least one fungicide from groups A) to P), as described above, is more efficient than combating those fungi with the individual compounds of formula (I) or individual fungicides from groups A) to P). By applying a compound of formula (I) together with at least one active compound from groups A) to P) a synergistic effect can be obtained, i.e. more than simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compound of formula (I) and at least one further active compound simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active compound applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When sequentially applying a compound of formula (I) and at least one further active compound, the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
In the binary mixtures and compositions according to the invention the weight ratio of the compound of formula (I) [component (1)] and the component (2) generally depends from the properties of the active components used, usually it is in the range of 1:10 000 to 10 000:1 , often it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1 , preferably in the range of 1:20 to 20:1 , more preferably in the range of 1 :5 to 5 : 1 and in particular in the range of 1 :2 to 2: 1.
According to a further embodiment of the binary mixtures and compositions, the weight ratio of the compound of formula (I) [component (1)] and the component (2) usually is in the range of 1000:1 to 1:1, often in the range of 100:1 to 1:1, regularly in the range of 50:1 to 1:1, preferably in the range of 20:1 to 1:1, more preferably in the range of 5 : 1 to 1 : 1 and in particular in the range of 2:1 to 1:1.
According to a further embodiment of the binary mixtures and compositions, the weight ratio of the compound of formula (I) [component (1)] and the component (2) usually is in the range of 1:1 to 1:1000, often in the range of 1:1 to 1:100, regularly in the range of 1:1 to 1:50, preferably in the range of 1:1 to 1:20, more preferably in the range of 1:1 to 1 :5 and in particular in the range of 1:1 to 1:2. In the ternary mixtures, i.e. compositions according to the invention comprising the compound of formula (I) [component (1)] and component (2) and a compound of formula (III) [component (3)], the weight ratio of compound of formula (I) [component (1)] and component (2) is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:5 to 5:1 and in particular in the range of 1:2 to 2:1, and the weight ratio of component (1) and component (3) is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:5 to 5:1 and in particular in the range of 1:2 to 2:1.
It is preferred that the ternary mixtures comprise as compounds III fungicidal compounds that are independently of each other selected from the groups A), B), C), D), E), F), G), H), I), J), K) L), M), N), O) and P); and wherein the at least one active compound III of component (3) is not identical with the at least one active compound II of component (2).
Any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the compound of formula (I) [component (1)].
These ratios are also suitable for seed treatment.
The method of treatment according to the invention also provides the use or application of component (1) and component (2) in a simultaneous, separate or sequential manner. If the single active ingredient is applied in a sequential manner, i.e. at different times, they are applied one after the other within a reasonable period, such as a few hours or days. Preferably the order of applying the component (1) and component (2) is not essential for working the present invention.
In the novel agrochemical composition according to the invention the component (1) and (2) are advantageously present in a synergistically effective weight ratio of (1):(2) in a range of 100:1 to 1:100, preferably in a weight ratio of 50:1 to 1:50, more preferably in a weight ratio of 20:1 to 1:20, even more preferably in a weight ratio of 10:1 to 1:10, 5:1 to 1:5 and 2:1 to 1:2.
Preferred formulations of agrochemical composition as disclosed in the present invention can have the following compositions (weight %): a. Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %
The following examples further illustrate, but do not limit, the invention. Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
Figure imgf000062_0001
b. Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
The following examples further illustrate, but do not limit, the invention.
Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Figure imgf000062_0002
c. Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Figure imgf000062_0003
Figure imgf000063_0001
d. Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %
The following examples further illustrate, but do not limit, the invention.
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
Figure imgf000063_0002
e. Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 % The following examples further illustrate, but do not limit, the invention.
The combination is mixed and ground with the adjuvants and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
Figure imgf000064_0001
The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
Figure imgf000064_0002
f. Seed treatment compositions
The following examples further illustrate, but do not limit, the invention.
The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
Figure imgf000064_0003
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Figure imgf000064_0004
Figure imgf000065_0002
g. Slow Release Capsule Suspension
28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
The composition comprising the compound of formula (I) [component (1)] and the component (2) may show a synergistic effect.
According to the present invention, whenever the efficacy of an active ingredient combination is greater than the sum of the efficacies of the individual components. The activity to be expected E for a given active ingredient combination obeys the so-called COLBY formula.
An efficacy of 0 means that the infection level of the treated plants is corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficacies of active compound combinations may be determined using Colby's formulas (COLBY, S.R. "Calculating synergistic and antagonistic responses of herbicide combination", Weeds, Vol. 15, pages 20-22; 1967).
Colby's formulas:
The expected activity for a given combination of two active compounds (binary composition) can be calculated as follows:
Figure imgf000065_0001
In which E represents the expected percentage of inhibition of the disease for the combination of two fungicides at defined doses (for example equal to x and y respectively), x is the percentage of inhibition observed for the disease by the compound (1) at a given dose (equal to x), y is the percentage of inhibition observed for the disease by the compound (2) at a defined dose (equal to y). When the percentage of inhibition observed for the combination is greater than E, there is a synergistic effect. The expected activity for a given combination of three active compounds (ternary composition) can be calculated as follows:
Figure imgf000066_0001
X: efficacy, expressed in % of the untreated control, when using the active compound (1) at the concentration a, Y: efficacy, expressed in % of the untreated control, when using the active compound (2) at the concentration b
Z: efficacy, expressed in % of the untreated control, when using the active compound (3) at the concentration c.
E is the efficacy when the active compounds (1), (2) and (3) are applied at application rates of a, b and c. Preparation of compound of formula (I):
The preparation of compounds of formula (I) have been descibed by various routes in analogy to prior art documentWO2018069841 and references therein or by synthesis routes comprising at least one of the following schemes (1) to (3) as shown below:
Scheme 1
Figure imgf000066_0002
The compound of formula (I) can be synthesized by treating compound of formula 3 with trimethylortoformate and -tohienesiilfonic acid followed by the reaction with different secondary amines (HNR'R2) as mentioned in US20110130282.
The compound 1 is an important intermediate for the synthesis of compound of formula (I). There are various methods described in the literature to synthesis compound formula 1 such as
Method 1: From corresponding benzoyl chloride using catalyst zinc chloride (ZnCl·) or aluminum chloride (AICR) in the presence of dichloromethane as described in Helvitachimica Act XXIX (1946), page No 1413-1424, and Tetrahedron, 2000, 56, page no 7199-7203.
Method 2: From corresponding benzoic acid in the presence of acid catalyst such as (a) trifluoromethane sulphonic acid as described in Tetrahedron, 2000, 56, pages 7199-7203; (b) Graphite and methane sulphonic acid as described in Synthesis, 2004, 13, page no 2165-2168; (c) Graphite and -toluene sulphonic acid as described in Helvetiva Chimica act, 2005, 88, page no 2282-2287; (d) 1- perfluorobutanesulphonic acid as described in Synthesis, 2000, 10, page no 1427-1430.
Method 3: From corresponding derivative of benzoic acid in the presence of metal triflates such as copper triflate, gallium triflate or antimonium triflate or ytterbium triflate or scandium triflate or bismuth triflate as described in Green chemistry, 4 (2002), page no 129-133 or in Tetrahedron, 56 (2000), page no 6 63- 6465 or Bull chemical society of Jpn, 2000, 73, page no 2325-2333.
Method 4: From corresponding substituted benzoic acid in the presence of phosphorus pentoxide (P2O5) as such or adsorbed on silica gel as described in Tetrahedron letters, 2008, 49, page no 6715-6719.
Scheme 2
Figure imgf000067_0001
The compound of formula (I) can be synthesized using suitably substituted compound of formula 2a and following the same methods as described in scheme 1. The corresponding intermediate 2a can be synthesized from phenyl acetonitrile in the presence of bases like sodium hydroxide, or sodium tert- butoxide, or sodium hydride followed by oxidation with hydrogen peroxide/m-chloroperbenzoic acid (Fh02/mCPBA) in the presence of aqueous potassium hydroxide (KOH) as described in (/. Org. Chem., 1983, 48, 4097-98, /. Org. Chem. 1983, 48, 4087-4096). Scheme 3
Figure imgf000068_0001
The compound of formula (I) can also be synthesised using a suzuki reaction by treating compound of formula 6 with the corresponding substituted benzyl halide as mentioned in Bioorganic & Medicinal
Chemistry Letters , 2004, 14 (4), page no 1023-1026. The compounds of formula 6 can be synthesised by treating the bromo derivative 5 with bis(pincolato)diboran using palladium acetate and [1,1'- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride [PdChCdppf)] dichloromethane complex in dioxane with good yield.
CHEMISTRY EXAMPLES:
The following representative examples set forth the manner and process of making compounds of the present invention without being a limitation thereof and include the best mode contemplated by the inventors for carrying out the invention.
Example 1: Preparation of N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N- methy lformimidamide :
Step A-Preparation of N-(2,5-dimethylphenyl)acetamide:
To a stirred solution of 2,5-dimethylaniline (50 g, 413 mmol) in 1 ,2-dichlormethane (500 mL), triethylamine (144 mL, 1031 mmol) and acetyl chloride (35.2 mL, 495 mmol) were added at 0 °C. The resulting reaction mixture was stirred for 2 h at 0 °C. After completion of the reaction, the reaction mixture poured onto the ice water. The aqueous layer was extracted thrice with 1,2-dichloromethane (1000 mL). The dichlormethane layer was separated, washed twice with water (500 mL) and brine solution (250 mL). The organic layer was separated, dried over anhydrous sodium sulphate, filtered and evaporated under high vacuum to obtain the desired N-(2,5-dimethylphenyl)acetamide (60 g, 368 mmol, 89 % yield). LCMS (M+H): 165.50.
Step B-Preparation of N-(2,5-dimethyl-4-(2-methylbenzoyl)phenyl)acetamide
A mixture of N-(2,5-dimethylphenyl)acetamide (50g, 306 mmol), aluminium chloride (102 g, 766 mmol) and 2-methylbenzoyl chloride (100 ml, 766 mmol) was mixed together and heated to 100 °C and maintained till completion of reaction. After completion of the reaction, the reaction mixture was quenched by 1 N HC1 (Approx 250 mL till clear solution obtained) and then extracted twice with 1,2- dichloromethane (500 mL). The combined organic layers were washed two times with brine (250 mL), dried over anhydrous sodium sulphate, then it was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane: ethyl acetate as eluent to obtain the desired N N-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)acetamide (70 g, 249 mmol, 81 % yield) as a solid LCMS (M+H): 281.4.
Step C-Preparation of N-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)acetamide
To a suspension of N-(2,5-dimethyl-4-(2-methylbenzoyl)phenyl)acetamide (35 g, 124 mmol) in acetonitrile (15 mL), triethylsilane (79 mL, 498 mmol) and borontrifluoride etherate (63.1 mL, 498 mmol) were added over a period of 10 min at 0 °C. After the complete addition, the reaction mixture was stirred for 36 h at 25 °C. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted thrice with dichloromethane (200 mL). The combined organic layers were dried over anhydrous sodium sulphate. The mixture was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane: ethyl acetate as eluent to obtain the desired N-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)acetamide (12 g, 44.9 mmol, 36.1 % yield) as white solid LCMS (M+H) 268.3.
Step D-Preparation of 2,5-dimethyl-4-(2-methylbenzyl)aniline:
To a suspension of N-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)acetamide (24 g, 90 mmol) in ethanol (200 mL), sodium hydroxide (108 g, 2693 mmol) in water (200 mL) was added at 25 °C and the reaction mixture was heated to reflux (100 °C) for 36 h. After completion of the reaction, the reaction mixture was cooled to 25 °C and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulphate. The reaction mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane: ethyl acetate as a eluent to obtain the desired 2,5-dimethyl-4-(2-methylbenzyl)aniline (13.5 g, 59.9 mmol, 66.7 % yield) as a white solid; LCMS (M+H) 226.34.
Step E- Preparation of N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N- methylformimidamide
A solution of 2,5-dimethyl-4-(2-methylbenzyl)aniline (7 g, 31.1 mmol) in trimethyl orthoformate (130 ml) and p-toluenesulfonic acid monohydrate (0.591 g, 3.11 mmol) was stirred at 103 °C for 4 h. The reaction mixture was concentrated under reduced pressure to obtain an intermediate which was then taken in 1,4-dioxane (100 mL). To, the resulting mixture, N-ethylmethylamine (13.50 ml, 155 mmol) was added and the reaction mixture was heated at 103 °C for 2 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain the residue, which was then purified by column chromatography on silica gel using hexane: ethyl acetate as eluent to obtain the desired N'- (2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (7 g, 23.77 mmol, 77 % yield). ¾-NM (400 MHz, DMSO-d6) d 7.59 (s, 1H), 7.17-7.14 (m, 1H), 7.10-7.03 (m, 2H), 6.80-6.77 (m, 1H), 6.59 (d,2H), 3.78 (d,2H), 3.42-3.35 (m, 1H), 3.29 (s, 1H), 2.90 (s, 3H), 2.22 (s, 3H), 2.09 (s, 3H), 2.04 (s, 3H), 1.10 (t, 3H); (M+l):295.1.
BIOLOGY EXAMPLES:
As described herein, the compounds of formula (I) show fungicidal activities which are exerted with respect to numerous fungi which attack on important agricultural crops. The compounds of the present invention were assessed for their activity as described in the following tests:
Biological Test Examples in vivo on plants
The compounds were further selected for in vivo (Greenhouse) preventive/curative testing. The methods followed to check the preventive/curative efficacy of compounds on the pathogens were as following:
Example A: Pyricularia oryzae test in Rice
The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications.
To test the preventive activity of compounds, healthy young rice plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 1.4xl06 Pyricularia oryzae inoculum. The inoculated plants were then kept in a greenhouse chamber at 24 °C temperature and 95 % relative humidity for disease expression.
A visual assessment of the performance of the compounds or compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compounds and mixtures were calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
Table-A: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly compound (1-2), compound (1-6) and compound (1-7) as component (1) and other components (2) against Pyricularia oryzae in Rice are shown in the table below:
Figure imgf000071_0001
Figure imgf000072_0001
Example B: Alter naria solani test in Tomato
The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications.
To test the preventive activity of compounds, healthy young tomato plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 0.24x10® Alternaria solani inoculum and 2% Malt. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression.
A visual assessment of the performance of the compounds or compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compounds and mixtures was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
Table-B: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Alternaria solani in Tomato are shown in the table below:
Figure imgf000073_0001
Figure imgf000074_0001
Example C: Erysiphe cichoracearum test in Cucumber
The single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications.
To test the preventive activity of compounds, healthy young cucumber plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a conidial suspension containing 2xl05 Erysiphe cichoracearum inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 50-60 % relative humidity for disease expression.
A visual assessment of the performance of the compounds and the respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
Table-C: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Erysiphe cichoracearum in Cucumber are shown in the table below:
Figure imgf000075_0001
Figure imgf000076_0001
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
Example D: Phakopsora pachyrhizi test in Soybean
The single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 50 ml. The test solutions were poured into spray bottles for further applications.
To test the preventive activity of compounds, healthy young Soybean plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2 xlO5 Phakopsora pachyrhizi conidia. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 80-90 % relative humidity for disease expression.
A visual assessment of the performance of the compounds and respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.
Table-D: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Phakopsora pachyrhizi in Soybean are shown in the table below.
Figure imgf000080_0002
Figure imgf000081_0001
Example E: Pamstagonospora nodorum/ Septoria nodorum/ Stagnospora nodorum test in Wheat The single compounds or compound combinations were dissolved in 2% DMSO/ Acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL. The spray solutions were poured into spray bottles for further applications.
To test the preventive activity of compounds, healthy young wheat plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2.8xl06 Stagnospora nodorum inoculum. The inoculated plants then were kept in a greenhouse chamber at 22-25 °C temperature and 90-100 % relative humidity for disease expression.
A visual assessment of the performance of the compounds and compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7 and 10 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis & stunting
Table-E: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) are particularly Compound (1-2), Compound (1-6) and Compound (1-7) as component (1) and other components (2) against Parastagonospora nodorum/ Septoria nodorum/ Stagnospora nodorum in Wheat are shown in the table below:
Figure imgf000082_0001
Figure imgf000083_0001
Figure imgf000084_0001
Figure imgf000085_0001
Having described the invention with reference to certain preferred embodiments, other embodiments will become apparent to one skilled in the art from consideration of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, may be practiced without departing from the scope of the invention.

Claims

CLAIMS:
1. A fungicidal composition comprising a mixture of components (1) and (2), wherein component (1) is a compound of formula (I),
Figure imgf000086_0001
Formula (I) wherein,
R1 is selected from the group consisting of Ci-G, -alkyl, C2-Ce-alkenyl, C3-C6-cycloalkyl-Ci-C3- alkyl and C3-C6-cycloalkyl;
R2 is independently selected from the group consisting of C2-Ce-alkyl, C2-Ce-alkenyl, C3-C6- cycloalkyl-Ci-C3-alkyl and C3-C6-cycloalkyl;
R3 and R4 are independently selected from the group consisting of halogen, cyano, Ci-Cr, -alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy and C3-C6-cycloalkyl;
R5 and R6 are independently selected from the group consisting of hydrogen, halogen, cyano, Ci- C3-alkyl and Ci-C3-alkoxy; or
R5 and R6 together with the carbon atom to which they are bound form a C=CR’R’, C=NR’ or cyclopropyl ring;
R’ is selected from the group consisting of hydrogen, Ci-C3-alkyl, C3-C6-cycloalkylalkyl and Ci-C3-alkoxy;
R7 is selected from the group consisting of hydrogen, halogen, cyano, Ci-Cr, -alkyl, C 1 -CV haloalkyl, Ci-Ce-alkoxy, Ci -C ,-alky Ithio, Ci-CValkylsulfi nyl, Ci-Ce-alkylsulfonyl, C3-C8- cycloalkyl and C3-C6-cycloalkyl-Ci-C3-alkyl; m represent integers 0, 1, 2, 3 or 4; or salts, N- oxides, metal complexes or stereoisomers thereof; and component (2) is a compound selected from the group consisting of:
(A) Inhibitors of the ergosterol biosynthesis, for example, (A001) cyproconazole, (A002) difenoconazole, (A003) epoxiconazole, (A004) fenhexamid, (A005) fenpropidin, (A006) fenpropimorph, (A007) fenpyrazamine, (A008) fluquinconazole, (A009) flutriafol, (A010) imazalil, (A011) imazalil sulfate, (A012) ipconazole, (A013) metconazole, (A014) myclobutanil, (A015) paclobutrazol, (A016) prochloraz, (A017) propiconazole, (A018) prothioconazole, (A019) Pyrisoxazole, (A020) spiroxamine, (A021) tebuconazole, (A022) tetraconazole, (A023) triadimenol, (A024) tridemorph, (A025) triticonazole, (A026) (lR,2S,5S)-5-(4-chlorobenzyl)-2- (chloromethyl)-2-methyl-l-(lH-l,2,4-triazol-l-ylmethyl)cyclopentanol, (A027) (lS,2R,5R)-5-(4- chlorobenzyl)-2-(chloromethyl)-2 -methyl- 1 -( 1H- 1 ,2,4-triazol-l-ylmethyl)cyclopentanol, (A028)
(2R)-2-(l-chlorocyclopropyl)-4-[(lR)-2,2-dichlorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (A029) (2R)-2-(l-chlorocyclopropyl)-4- [(lS)-2,2-dichlorocyclopropyl] - 1 -(1H- 1 ,2,4-triazol- 1 - yl)butan-2-ol, (A030) (2R)-2-[4-(4-chlorophenoxy)-2-(trilluoromethyl)phenyl]-l-(lH-l,2,4-triazol- 1 -yl)propan-2-ol, (A031) (2S)-2-( 1 -chlorocyclopropyl)-4-[(lR)-2,2-dichlorocyclopropyl] -1 -(1H-
1.2.4-triazol-l-yl)butan-2-ol, (A032) (2S)-2-(l-chlorocyclopropyl)-4-[(lS)-2,2- dichlorocyclopropyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol, (A033) (2S)-2-[4-(4-chlorophenoxy)-2- (trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol, (A034) (R)-[3-(4-chloro-2- fluorophenyl)-5-(2,4-difhiorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (A035) (S)-[3-(4- chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridiii-3-yl)methanol, (A036) [3- (4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (A037) 1 -( { (2R,4S)-2- [2-chloro-4-(4-chlorophenoxy)phenyl] -4-methyl- 1 ,3-dioxolan-2-yl } methyl)- 1 H-
1.2.4-triazole, (A038) 1 -( { (2S ,4S)-2- [2-chloro-4-(4-chlorophenoxy)phenyl] -4-methyl-l,3 -dioxolan-
2-yl}methyl)-lH- 1,2, 4-triazole, (A039) l-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A040) l-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate, (A041) l-{ [rel(2R,3S)-3-(2- chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanate,
(A042) 2- [(2R,4R,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4- triazole-3-thione, (A043) 2-[(2R,4R,5S)- 1 -(2,4-dichlorophenyl)-5- hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-l,2,4-triazole-3-thione, (A044) 2-
[(2R,4S,5R)- l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3-thione, (A045) 2-[(2R,4S,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan- 4-yl] -2,4-dihydro-3H- 1 ,2,4-triazole-3-thione, (A046) 2-[(2S ,4R,5R)- 1 (2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A047) 2-[(2S,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro- 3H-l,2,4-triazole-3-thione, (A048) 2-[(2S,4S,5R)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A049) 2-[(2S,4S,5S)-l-(2,4- dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A050) 2-[l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l- yl)propan-2-ol, (A052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-l-(lH-l,2,4-triazol-l-yl)butan-2- ol, (A053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)butan-2-ol,
(A054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l -yl)pentan-2-ol,
(A055) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-l,2,4-triazol-l-yl)propan-2-ol,
(A056) 2-{ [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-l,2,4- triazole-3 -thione, (A057) 2-{ [rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l,2,4-triazole-3-thione, (A058) 2-{ [rel(2R,3S)-3-(2-chlorophenyl)-2- (2,4-difluorophenyl)oxiran-2- yl]methyl}-2,4-dihydro-3H-l ,2,4-triazole-3-thione, (A059) 5-(4- chlorobenzyl)-2-(chloromethyl)-2 -methyl- 1 -(1H- 1 ,2,4-triazol- 1 -ylmethyl)cyclopentanol, (A060) 5 - (allylsulfanyl)- 1- { [3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl } - 1H- 1 ,2,4- triazole, (A061) 5-(allylsulfanyl)-l-{[rel(2R,3R)-3-2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-
2-yl]methyl } - 1 H- 1 ,2,4-triazole, (A062) 5 -(allylsulfanyl)- 1 - { [rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4- difluorophenyl)oxiran-2-yl]methyl}-lH- 1,2, 4-triazole, (A063) N'-(2,5-dimethyl-4-{ [3-(l, 1,2,2- tetrafluoroethoxy)phenyl]sulfanyl }phenyl)-N-ethyl-N-methybmidoformamide, (A064) N'-(2,5- dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,
(A065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N- methyhmidoformamide, (A066) N'-(2,5-dimethyl-4-{ [3-
(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidofonnamide, (A067) N'-(2,5- dimethyl-4- { 3-[(l ,l,2,2-tetrafluoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl- N-methyhmidoformamide, (A068) N'-(2,5-dimethyl-4-{3-[(2,2,2- trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyhmidoformamide, (A069) N'-(2,5- dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N- methybmidoformamide, (A070) N'-(2,5- dimethyl-4-{3-
[(pentafluoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl-N-methylimidoformamide, (A071) N'-(2,5- dimethyl-4-phenoxyphenyl)-N-ethyl-N-methybmidoformamide, (A072) N'-(4-{ [3-
(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (A073) N'-(4-{ 3-[(difluoromethyl)sulfanyl]phenoxy } -2,5-dimethylphenyl)-N-ethyl-N- methybmidoformamide, (A074) N'-[5-bromo-6-(2,3-dihydro-lH-inden-2-yloxy)-2-methylpyridin-
3-yl]-N-ethyl-N-methybmidoformamide, (A075) N'-{4-[(4,5-dichloro-l,3-thiazol-2-yl)oxy]-2,5- dimethylphenyl } -N-ethyl-N-methylimidoformamide, (A076) N'- { 5 -bromo-6-[( 1R)- 1 -(3 ,5 - difluorophenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N-methylimidofonnamide, (A077) N'- { 5- bromo-6- [( lS)-l-(3,5 -difluorophenyl)ethoxy] -2-methylpyridin-3-yl } -N-ethyl-N- methylimidoformamide, (A078) N'- { 5-bromo-6- [(cis-4-isopropylcyclohexyl)oxy ] -2-methylpyridin- 3-yl}-N-ethyl-N-methylimidofomamide, (A079) N'-{5-bromo-6-[(trans-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (A080) N'- { 5 -bromo-6- [ 1 -(3 ,5 -difluorophenyl)ethoxy ] -2-methylpyri din-3 -y 1 } -N -ethyl -N - methylimidoformamide, (A081) Mefentrifluconazole, (A082) Ipfentrilluconazole, (A083) 1 -(2,4- difluorophenyl)-2-( 1 H- 1 ,2,4-triazol- 1 -yl)- 1 - [ 1 -(2,6-difluoro-4-chlorophenoxy)cyclopropyl]ethanol,
(A084) l-[2-(l-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-lH-imidazole-5- carbonitrile;
(B) Inhibitors of the respiratory chain at complex I or II, for example, (B001) benzovindiflupyr, (B002) bixafen, (B003) boscalid, (B004) carboxin, (B005) fluopyram, (B006) flutolanil, (B007) fluxapyroxad, (B008) furametpyr, (B009) Isofetamid, (B010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (B011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (B012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (B013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (B014) isopyrazam (syn- epimeric enantiomer 1R,4S,9R), (B015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (B016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (B017) penflufen, (B018) penthiopyrad, (B019) pydiflumetofen, (B020) Pyraziflumid, (B021) sedaxane, (B022) l,3-dimethyl-N-(l,l,3- trimethyl-2,3-dihydro-lH-inden-4-yl)-l H-pyrazole-4-carboxamide, (B023) l,3-dimethyl-N-[(3R)-
1.1.3-trimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B024) 1,3-dimethyl-N-
[(3S)- 1,1, 3-trimethyl -2, 3-dihydro- lH-inden-4-yl]-lH-pyrazole-4- carboxamide, (B025) l-methyl-3- (trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-lH-pyrazole-4-carboxamide, (B026) 2- fluoro-6-(trifluoromethyl)-N-(l,l,3-trimethyl-2, 3-dihydro- lH-inden-4- yl)benzamide, (B027) 3- (difluoromethyl)- l-methyl-N-( 1 , 1 , 3-trimethyl -2, 3-dihydro- lH-inden-4-yl)-lH- pyrazole-4- carboxamide, (B028) 3-(difluoromethyl)-l-methyl-N-[(3R)-l,l,3-trimethyl-2,3-dihydro-lH- inden-
4-yl]-lH-pyrazole -4-carboxamide, (B029) 3-(difhioromethyl)-l-methyl-N-[(3S)-l,l,3-trimethyl-
2.3-dihydro- lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (B030) 3-(difluoromethyl)-N-(7-fluoro-
1.1.3- trimethyl-2,3 -dihydro-lH-inden-4-yl)-l -methyl- lH-pyrazole-4-carboxamide (Fluindapyr),
(B031) 3- (difhioromethyl)-N-[(3R)-7-fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl- lH-pyrazole-4-carboxamide, (B032) 3-(difhioromethyl)-N-[(3S)-7-fluoro-l,l,3-trimethyl-2,3- dihydro-lH-inden-4- yl]-l-methyl- 1 H-pyrazole-4-carboxamide, (B033) 5,8-difluoro-N-[2-(2- fluoro-4-{ [4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (B034) N-(2- cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl) -5-fluoro-l-methyl-l-H-pyrazole-4- carboxamide, (B035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro- 1 -methyl- lH-pyrazole-4-carboxamide, (B036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3- (difluoromethyl)-5-fluoro- 1-methyl- lH-pyrazole-4-carboxamide, (B037) N-(5-chloro-2- ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-iluoro-l-methyl-lH-pyrazole-4-carboxamide, (B038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difbioromethyl)-5-fbioro-l-methyl-lH- pyrazole-4-carboxamide (isoflucpyram), (B039) N-[(lR,4S)-9-(dichloromethylene)-l,2,3,4- tetrahydro-l,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (B040) N-[( 1 S ,4R)-9-(dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3-
(difluoromethyl)-l -methyl- lH-pyrazole-4-carboxamide, (B041) N-[l-(2,4-dichlorophenyl)- 1- methoxypropan-2-yl]-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxamide, (B042) N-[2- chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH- pyrazole-4-carboxamide, (B043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl- 3-(difhioromethyl)-5-fhioro-l-methyl-lH-pyrazole-4- carboxamide, (B044) N-[5-chloro-2-
(trifhioromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B045) N-cyclopropyl-3-(difhioromethyl)-5-fluoro-l-methyl-N-[5-methyl-2- (trifluoromethyl)benzyl]-lH-pyrazole-4-carboxamide, (B046) N-cyclopropyl-3-(difluoromethyl)-5- fluoro-N-(2-fluoro-6-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (B047) N- cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-l -methyl- lH-pyrazole-4- carboxamide, (B048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-l-methyl- IH-pyrazole-4-carbothioamide, (B049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2- isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (B050) N-cyclopropyl-3-(difluoromethyl)- 5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-l-methyl-lH-pyrazole-4-carboxamide, (B051) N- cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4- carboxamide, (B052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-iluorobenzyl)-5-fluoro-l- methyl- lH-pyrazole-4-carboxamide, (B053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5- methylbenzyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B054) N-cyclopropyl-N-(2- cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl-lH-pyrazole-4-carboxamide, (B055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-l-methyl- lH-pyrazole-4-carboxamide, (B056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(dilluoromethyl)- 5 -f uoro-1 -methyl- lH-pyrazole-4-carboxamide, (B057) 2-(difluoromethyl)-N-(l,l-dimethyl-3- propyl-2,3-dihydro-lH-inden-4- yl)nicotinamide, (B058) pyrapropoyne, (B059) inpyrfluxam, (B060) isollucypram;
(C) Inhibitors of the respiratory chain at complex III, for example, (COOl) ametoctradin, (C002) amisulbrom, (C003) azoxystrobin, (C004) coumethoxystrobin, (C005) coumoxystrobin, (C006) cyazofamid, (C007) dimoxystrobin, (C008) enoxastrobin, (C009) famoxadone, (COIO) fenamidone, (C011) flufenoxystrobin, (C012) fluoxastrobin, (C013) kresoxim-methyl, (C014) metominostrobin, (C015) orysastrobin, (C016) picoxystrobin, (C017) pyraclostrobin, (C018) pyrametostrobin, (C019) pyraoxystrobin, (C020) trifloxystrobin, (C021) (2E)-2-{2-[({ [(lE)-l-(3-{ [(E)-l-fluoro-2- phenylvinyl]oxy} phenyl)ethylidene] amino} oxy)methyl]phenyl } -2-(methoxyimino )-N- methylacetamide, (C022) (2E,3Z)-5-{ [l-(4-chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-
(methoxyimino)-N,3-dimethylpent-3- enamide, (C023) (2R)-2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C024) (2S)-2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C025) (3S,6S,7R,8R)-8- benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9- dioxo-l,5-dioxonan-7-yl-2-methylpropanoate (Fenpicoxamid), (C026) 2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (Mandestrobin), (C027) N-(3- ethyl- 3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (C028) (2E,3Z)-5-{ [1-
(4-chloro-2-fluorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (C029) methyl {5-[3-(2,4-dimethylphenyl)-lH-pyrazol-l-yl]-2-methylbenzyl}carbamate, (C030) 1- (2-{ [l-(4-chlorophenyl)pyrazol-3-yl]oxymethyl}-3-methylphenyl)-l,4-dihydro-4-methyl-5H- tetrazol-5-one (Metyltetraprole), (C031) llorylpicoxamid;
(D) Inhibitors of the mitosis and cell division, for example, (D001) carbendazim, (D002) diethofencarb, (D003) ethaboxam, (D004) fhiopicolide, (D005) pencycuron, (D006) thiabendazole, (D007) thiophanate -methyl, (D008) zoxamide, (D009) 3-chloro-4-(2,6- difluorophenyl)-6-methyl-5- phenylpyridazine, (D010) 3-chloro-5-(4-chlorophenyl)-4-(2,6- difluorophenyl)-6-methylpylidazine, (D011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6- trifluorophenyl)pyridazine, (D012) 4-(2- bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-l ,3- dimethyl- lH-pyrazol-5-amine, (D013) 4-(2-bromo- 4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)- l,3-dimethyl-lH-pyrazol-5-amine, (DO 14) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-l,3- dimethyl-lH-pyrazol-5 -amine, (D015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6- fluorophenyl)-l, 3 -dimethyl- 1 H-pyrazol-5 -amine, (DO 16) 4-(2-bromo-4-fluorophenyl)-N-(2- chlorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (DO 17) 4-(2-bromo-4-fluorophenyl)-N-(2- fluorophenyl)- 1,3 -dimethyl- 1 H-pyrazol-5 -amine, (D018) 4-(2-chloro-4-fluorophenyl)-N-(2,6- difluorophenyl)-l, 3-dimethyl- lH-pyrazol-5-amine, (DO 19) 4-(2-chloro-4-fluorophenyl)-N-(2- chloro-6-fluorophenyl)-l ,3-dimethyl-lH-pyrazol-5-amine, (D020) 4-(2-chloro-4-fluorophenyl)-N- (2-chlorophenyl)-l, 3 -dimethyl- 1 H-pyrazol-5 -amine, (D021 ) 4-(2-chloro-4-fluorophenyl)-N-(2- fluorophenyl)- 1,3 -dimethyl- 1 H-pyrazol-5 -amine, (D022) 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3 ,6-dimethylpyridazine, (D023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4- fluorophenyl)-l,3 -dimethyl- 1 H-pyrazol-5 -amine, (D024) N-(2-bromophenyl)-4-(2-chloro-4- fluorophenyl)- 1,3 -dimethyl- 1 H-pyrazol-5 -amine, (D025) N-(4-chloro-2,6-difluorophenyl)-4-(2- chloro-4-fluorophenyl)-l, 3-dimethyl -lH-pyrazol-5-amine;
(E) Compounds capable to have a multisite action, for example (E001) bordeaux mixture, (E002) captafol, (E003) captan, (E004) chlorothalonil, (E005) copper hydroxide, (E006) copper naphthenate, (E007) copper oxide, (E008) copper oxychloride, (E009) copper(2+) sulfate, (E010) dithianon, (E011) dodine, (E012) folpet, (E013) mancozeb, (E014) maneb, (E015) metiram, (E016) metiram zinc, (E017) oxine-copper, (E018) propineb, (E019) sulfur and sulfur preparations including calcium polysulfide, (E020) thiram, (E021) zineb, (E022) ziram, (E023) 6- ethyl-5,7-dioxo-6,7-dihydro-5H- pynolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile;
(F) Compounds capable to induce a host defence, for example (F001) acibenzolar-S-methyl, (F002) isotianil, (F003) probenazole, (F004) tiadinil;
(G) Inhibitors of the amino acid and/or protein biosynthesis, for example (G001) cyprodinil, (G002) kasugamycin, (G003) kasugamycin hydrochloride hydrate, (G004) oxytetracycline, (G005) pyrimethanil, (G006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline;
(H) Inhibitors of the ATP production, for example (H001) silthiofam;
(I) Inhibitors of the cell wall synthesis, for example (1001) benthiavalicarb, (1002) dimethomorph, (1003) flumorph, (1004) iprovalicarb, (1005) mandipropamid, (1006) pyrimorph, (1007) valifenalate, (1008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en-l-one, (1009) (2Z)-3 -(4-tert-butylphenyl)-3 -(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -one;
(J) Inhibitors of the lipid and membrane synthesis, for example (J001) propamocarb, (J002) propamocarb hydrochloride, (J003) tolclofos-methyl;
(K) Inhibitors of the melanin biosynthesis, for example (K001) tricyclazole, (K002) 2,2,2- trifluoroethyl { 3 -methyl- 1 - [(4-methylbenzoyl)amino]butan-2-yl } carbamate;
(L) Inhibitors of the nucleic acid synthesis, for example (L001) benalaxyl, (L002) benalaxyl-M (kiralaxyl), (L003) metalaxyl, (L004) metalaxyl-M (mefenoxam);
(M) Inhibitors of the signal transduction, for example (M001) fludioxonil, (M002) iprodione, (M003) procymidone, (M004) proquinazid, (M005) quinoxyfen, (M006) vinclozolin;
(N) Compounds capable to act as an uncoupler, for example (N001) fluazinam, (N002) meptyldinocap;
(O) Further compounds, for example (O001) Abscisic acid, (0002) benthiazole, (0003) bethoxazin, (0004) capsimycin, (0005) carvone, (0006) chinomethionat, (0007) cufraneb, (0008) cyflufenamid, (0009) cymoxanil, (OOIO) cyprosulfamide, (O011) flutianil, (0012) fosetyl-aluminium, (0013) fosetyl-calcium, (0014) fosetyl-sodium, (0015) methyl isothiocyanate, (0016) metrafenone, (0017) mildiomycin, (0018) natamycin, (0019) nickel dimethyldithiocarbamate, (0020) nitrothal -isopropyl, (0021) oxamocarb, (0022) Oxathiapiprolin, (0023) oxyfenthiin, (0024) pentachlorophenol and salts, (0025) phosphorous acid and its salts, (0026) propamocarb-fosetylate, (0027) pyriofenone (chlazafenone), (0028) tebufloquin, (0029) tecloftalam, (0030) tolnifanide, (0031) l-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-l,2- oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l- yljethanone, (0032) l-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-l ,2-oxazol-3-yl]-l,3-thiazol- 2-yl}piperidin-l-yl)-2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]ethanone, (0033) 2-(6- benzylpyridin-2-yl)quinazoline, (0034) 2,6-dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole- l,3,5,7(2H,6H)-tetrone, (0035) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2- yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l -yljethanone, (0036) 2-[3 ,5-bis(difluoromethyl)- 1 H-pyrazol- 1 -yl] - 1 - [4-(4- { 5- [2-chloro-6-(prop-2-yn- 1 -yloxy)phenyl] - 4, 5-dihydro- l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l -yljethanone, (0037) 2-[3,5- bis(difluoromethyl)-lH-pyrazol- 1 -yl] - 1 - [4-(4- { 5 -[2-fluoro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5 - dihydro- l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (0038) 2-[6-(3-fluoro-4- methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (0039) 2-{(5R)-3-[2-(l-{ [3,5- bis(difluoromethyl)-lH-pyrazol- 1 -yl] acetyl } piped din-4-yl)- 1 ,3-thiazol-4-yl] -4,5 -dihydro-1, 2- oxazol-5-yl}-3-chlorophenyl methanesulfonate, (0040) 2-{(5S)-3-[2-(l-{[3,5-bis(difluoromethyl)- lH-pyrazol-l-yl]acetyl]piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-yl}-3- chlorophenyl methanesulfonate, (0041) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6- fluorophenylJpropan-2-ol, (0042) 2-{2-fhioro-6-[(8-fluoro-2-methylquinolin-3- yl)oxy]phenyl] propan-2 -ol, (0043) 2-{3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5-ylJ-3-chlorophenyl methanesulfonate (fluoxapiprolin), (0044) 2-{3-[2-(l-{ [3,5-bis(difluoromethyl)-lH- pyrazol- 1 -yl] acetyl } piperidin-4-yl)- 1 ,3 -thiazol-4-yl] -4,5-dihydro- 1 ,2-oxazol-5 -yl {phenyl methanesulfonate, (0045) 2-phenylphenol and salts, (0046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4- dihydroisoquinolin- 1 -yl)quinoline, (0047) 3 -(4,4-difluoro-3 ,3-dimethyl-3 ,4-dihydroisoquinolin- 1 - yl)quinoline (Quinofumelin), (0048) 4-amino-5-fluoropyrimi din-2 -ol (tautomeric form: 4-amino-5- fluoropyrimidin-2(lH)-one), (0049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (0050) 5- amino- l,3,4-thiadiazole-2-thiol, (0051) 5 -chloro-N' -phenyl -N'-(prop-2-yn-l -yl)thiophene-2- sulfonohydrazide, (0052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (0053) 5-fluoro-2- [(4-methylbenzyl)oxy]pyrimidin-4-amine, (0054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3- dihydro- 1,4-benzoxazepine, (0055) but-3-yn-l-yl{6-[({ [(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino} oxy)methyl]pyridin-2-yl} carbamate, (0056) ethyl (2Z)-3-amino-2- cyano-3-phenylacrylate, (0057) phenazine-1 -carboxylic acid, (0058) propyl 3,4,5- trihydroxybenzoate, (0059) quinobn-8-ol, (0060) quinolin-8-ol sulfate (2:1), (0061) tert-butyl {6- [( { [( 1 -methyl- lH-tetrazol-5-yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamate, (0062) 5-fhioro-4-imino-3-methyl-l-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(lH)-one, (0063) pyridachlometyl, (0064) ipflufenoquin, (0065) aminopyrifen;
(P) Inhibitors of histone deacetylase for example (P001) N-(l-ethylcyclopropyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P002) N-(2-isopropylcyclopropyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P003) N-(2-methylcyclopropyl)-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P004) N-(l-methylcyclopropyl)-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P005) N-(2-ethylcyclopropyl)-4-[5-
(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P006) N-(2,4-difluorophenyl)-4-[5-
(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P007) 5-(trifluoromethyl)-3-[4-[[3-
(trifluoromethyl)-l,2,4triazol-l-yl]methyl]phenyl]-l,2,4-oxadiazole; (P008) 2-[[4-[5-
(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]-l ,2,4-triazole-3-carbonitrile; (P009) ethyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (PO 10) N -cyclopropyl- 1 - [ [4-[5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole -4-carboxamide; (P011) N,N-dimethyl-l-[[4-[5-(trifluoromethyl)- 1, 2, 4-oxadiazol-3-yl]phenyl]methyl]pyrazole -4-carboxamide; (P012) N-methyl-l-[[4-[5-
(trifluoromethyl)-l, 2, 4-oxadiazol-3-yl]phenyl]methyl]pyrazole -4-carboxamide; (P013) N,N,- dimethyl-H[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazol-3-amine; (P014) 3-[4-[(5-ethylsulfanyl-l,2,4-triazol-l-yl)methyl]phenyl]-5-(trifluoromethyl)-l,2,4- oxadiazole; (PO 15) 3- [4-(triazolo[4,5 -bjpyridin- 1 -ylmethyl)phenyl] -5 -(trifluoromethyl)- 1 ,2,4- oxadiazole; (PO 16) 3- [4-(triazolo[4,5 -b]pyridin-2-ylmethyl)phenyl] -5 -(trifluoromethyl)- 1 ,2,4- oxadiazole; (P017) 3-[4-(triazolo[4,5-b]pyridin-3-ylmethyl)phenyl]-5-(trifluoromethyl)-l,2,4- oxadiazole; (P018) methyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate; (P019) ethyl l-[[3-fluoro-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate; (P020) A(/V-diethyl-l-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P021) N- methoxy-/V-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxamide; (P022) propyl l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrazole-4-carboxylate; (P023) /V-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrazole -4-carboxamide; (P024) /V-ethyl-l-[[4-[5- (trifluoromethyl)-l ,2, 4-oxadiazol-3-yl]phenyl]methyl]pyrazole -4-carboxamide; (P025) l-[[4- [5 -(triflu oromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide; (P026) N- methoxy-1 -[ 1 -[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazol-4- yl]methanimine; (P027) ethyl l-[l-[4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]phenyl]ethyl]pyrazole-4-carboxylate; (P028) l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one; (P029) l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]piperidin-2-one; (P030) 4-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]morphobn-3-one; (P031) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]isoxazobdin-3-one; (P032) 2-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3 -yl]phenyl]methyl]isoxazobdin-3-one; (P033) 5 ,5 -dimethyl-2- [ [4- [5-
(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazobdin-3-one; (P034) 3,3- dimethyl-1 [4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one; (P035) l-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidm-2- one; (P036) l-[[2-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin- 2-one; (P037) 2-[[4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one; (P038) 1 -[ [3-fluoro-4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2- one; (P039) 3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]oxazolidm-2-one; (P040) l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]imidazolidin- 2-one; (P041) l-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3- dimethyl-piperidin-2-one; (P042) l-[[3-fluoro-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrobdin-2-one; (P043) 2-[[3-fluoro-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]-4,4-dimethyl-isoxazobdin-3-one; (P044) 2-[[2,3-difluoro-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazobdin-3-one; (P045) 2-[[3-fluoro- 4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one; (P046) l-[[3- fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one; (P047) N-[[4- [5 -(triflu oromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P048) 2,2-dimethyl- N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]but-3-ynamide; (P049) N-[[4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide; (P050) 3-methyl-N-[[4- [5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide; (P051) 2-methyl-N-[[4- [5 -(triflu oromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide; (P052) 2-methyl-N- [[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide; (P053) 2-methoxy- N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]; (P054) 3,3,3-trifluoro-N-[[3- fluoro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P055) 3,3,3- trifluoro-N- [ [2-fluoro-4-[5 -(triflu oromethyl)- 1 ,2,4-oxadiazol-3 - yl]phenyl]methyl]propanamide; (P056) N-[[2,3-difluoro-4-[5-(triiluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]butanamide; (P057) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide; (P058) 2-
(difluoromethoxy)-N-[[4-[5-(tri fluoromethyl)-l, 2, 4-oxadiazol-3-yl]phenyl]methyl] acetamide; (P059) 2-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide; (P060) l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P061) l-ethyl-l-methyl-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P062) l-ethoxy-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P063) l-methoxy-l-methyl-3-[[4-[5-(trifbioromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]; (P064) l,l-diethyl-3-[[4-[5-(trifluoromethyl)-l ,2,4-oxadiazol- 3-yl]phenyl]methyl]urea; (P065) N-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide; (P066) N-methoxy-N-[[4-[5-(trifluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]pent-4-ynamide; (P067) N-methoxy-2-methyl-N-[[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide; (P068) N,2-dimethoxy- N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P069) N- cyclopropyl-3 ,3 ,3 -trifluoro-N- [ [4- [5-(trilluoromethyl)- 1 ,2,4-oxadiazol-3 - yl]phenyl]methyl]propanamide; (P070) 2,2-difluoro-N-(2-methoxyethyl)-N-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclo propanecarboxamide; (P071) N- ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P072) N-[[3-fbioro-4-[5-(triiluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy- propanamide; (P073) 2-methoxy-N-(2,2,2-trifluoroethyl)-N-[[4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl] acetamide; (P074) N-[[2,3-difluoro-4-[5-(trifbioromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-cyclopropane carboxamide; (P075) 2-
(difbioromethoxy)-N-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]acetamide; (P076) N-ethoxy-2-methoxy-N-[[4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide; (P077) N-isopropyl-N-[[4-[5-(trilluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]tetrahydrofuran-2-carboxamide; (P078) l-methoxy-3- methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P079) 3- cyclopropyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P080) 3-ethoxy-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P081) 3-allyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P082) l-cyclopropyl-3-methoxy-3-methyl-l-[[4-[5-(trilluoromethyl)-
1.2.4-oxadiazol-3-yl]phenyl]methyl]urea; (P083) 3-isopropyl-l-methoxy-l-[[4-[5-
(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P084) l-methoxy-3 -prop-2 -ynyl- l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P085) l-[[3-fluoro-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l-methoxy-3-methyl-urea; (P086) 3- (cyclopropylmethyl)-l-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]urea; (P087) l-ethyl-3-(2,2,2-trifluoroethyl)-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3- yl]phenyl]methyl]urea; (P088) l,3-dimethoxy-l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3 -yl]phenyl]methyl]urea; (P089) 3-ethyl- 1 -methoxy- 1 - [ [4- [5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]phenyl]methyl]urea; (P090) N-methyl-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]benzamide; (P091) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]benzamide; (P092) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]benzamide; (P093) N-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]cyclopropanecarboxamide; (P094) N-(2-fluorophenyl)-4-[5-(trifluoromethyl)- 1,2,4- oxadiazol-3-yl]benzamide; (P095) 2,2-difhroro-N-methyl-2-[4-[5-(trifluoromethyl)-l ,2,4- oxadiazol-3-yl]phenyl]acetamide; (P096) N-allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol- 3-yl]phenyl]methyl]acetamide; (P097) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzamide; (P098) N-[(Z)-N-methoxy-C-methyl- carbonimidoyl]-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (P100) N-allyl-N-[[4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide; (P101) 4,4-dimethyl-l- [[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrobdm-2-one; (P102) N- methyl-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzenecarbothioamide; (P103) 5-methyl- l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrohdin-2-one, (P104) N- methyl-4-[5-(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]benzenecarboxamide; (P105) Nl-methyl- N2-(4-(5 -(trifluoro methyl)- 1 ,2,4-oxadiazol-3 -yl)benzyl)oxalamide ;
(Q) Q001) l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5- methyl-2-pyrazoline-3-carboxylic acid, (Q002) ethyl l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate ("mefenpyr (-diethyl)").
2. The fungicidal composition as claimed in claim 1, wherein said component (1) is a compound of formula (I),
Figure imgf000097_0001
formula (I) wherein, R1 is selected from the group consisting of methyl, ethyl, isopropyl and cyclopropyl;
R2is selected from the group consisting of ethyl, isopropyl, cyclopropyl and cyclopropylmethyl;
R3 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl and cyclopropyl;
R4 is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy and cyclopropyl;
R5 and R6 are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, halo methyl and methoxy;
R5 and R6 together with the carbon atom to which they are bound form a cyclopropyl ring or represents C=N-Ci-C3-alkyl;
R7 is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy and cyclopropyl; m represent integers 0, 1, 2, 3 or 4; and salts, N-oxides, metal complexes or stereoisomers thereof;
3. The fungicidal composition as claimed in claim 1, wherein said component (1) is selected from: (I- 1) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide; (1-2) N'-(2,5- dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; (1-3) N-ethyl-N'-(5- methoxy-2-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide; (1-4) N'-(4-((2- bromophenyl)(methoxy)methyl) -2 ,5 -dimethylphenyl)-N -ethy 1-N -methylformimidamide ; (1-5 ) N'- (5-chloro-4-((4-chloro-3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N- methylformimidamide; (1-6) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N- methylformimidamide; (1-7) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N- methylformimidamide; (1-8) N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N- methylformimidamide; (1-9) N'-(4-(3,5-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N- methylformimidamide; (I- 10) N'-(2-chloro-4-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N- methylformimidamide; (1-11) N'-(2-chloro-4-((2-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N- ethyl -N-methylformimidamide; (1-12) N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimethylphenyl)-N- ethyl-N-methylformimidamide; (T13) N'-(5-chloro-4-(3-chloro-2-fluorobenzyl)-2-methylphenyl)- N-ethyl-N-methylformimidamide; (1-14) N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5- methylphenyl)-N-ethyl-N-methylformimidamide and (1-15) N'-(2-chloro-4-(3-chloro-5- fluorobenzyl) -5 -methylphenyl)-N -ethyl-N -methylformimidamide.
4. The fungicidal composition as claimed in claim 1, wherein said component (2) is selected from the group consisting of:
(A) inhibitors of the ergosterol synthesis,
(B) inhibitors of the respiratory chain at complex I or II,
(C) inhibitors of the respiratory chain at complex III,
(E) compounds capable of having a multisite action,
(L) inhibitors of the nucleic acid synthesis,
(M)inhibitors of the signal transduction,
(N) compounds capable of acting as uncoupler,
(O) other fungicides,
(P) HDAC inhibitors
(Q) compounds capable to act as a safener.
5. The fungicidal composition as claimed in claim 1, wherein said component (2) is selected from the group consisting of (AOOl)cyproconazole, (A002) difenoconazole, (A004) tetraconazol (A006) fenpropimorph, (A009) flutriafol, (A013) metconazole, (A017) propiconazole, (A018) prothioconazole, (A021) tebuconazole, (A022) epoxiconazole, (A081) mefentrifluconazole, (B001) benzovindiflupyr, (B002) bixafen, (B005) fluopyram, (B007) fluxapyroxad, (B019) pydiflumetofen, (B30) fluindapyr, (B038) isoflucpyram, (B059) inpyrfluxam, (C003) azoxystrobin, (C012) fluoxastrobin (C014) metominostrobin, (C017) pyraclostrobin, (C016) picoxystrobin, (C020) trifloxystrobin, (C025) (3S,6S,7R,8R)-8-benzyl-3-[({3-
[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5- dioxonan-7-yl-2-methylpropanoate (Fenpicoxamid), (C030) l-(2-{[l-(4-chlorophenyl)pyrazol-3- yl]oxymethyl}-3-methylphenyl)-l,4-dihydro-4-methyl-5H-tetrazol-5-one (Metyltetraprole),
(D001) carbendazim, (D007) thiophanate -methyl, (E004) chlorothalonil, (E010) dithianon, (E013) mancozeb, (E020) thiram, (L003) metalaxyl, (M001) fludioxonil, (N001) fluazinam, (0022) Oxathiapiprolin, (0043) 2- { 3 - [2-( 1 - { [3 ,5 -bis(difhioromethyl)- 1 H-pyrazol- 1 -yl] acetyl }piperidin-4- yl)- 1 ,3 -thiazol-4-yl] -4,5-dihydro- 1 ,2-oxazol-5 -yl } -3 -chlorophenyl methanesulfonate
(fluoxapiprolin), (0046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (0047) 3-(4,4-difluoro-3 ,3-dimethyl-3 ,4-dihydroisoquinolin- l-yl)quinoline (Quinofumelin),
(0065) ipflufenoquin, (P006) N-(2,4-difhiorophenyl)-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yljbenzamide, (P103) 5-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]pyrrolidin-2-one and (P105) Nl-methyl-N2-(4-(5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl)benzyl)oxalamide.
6. The fungicidal composition as claimed in claim 1, wherein said composition further comprises an agriculturally acceptable auxiliaries, solvents, carriers, surfactants or extenders.
7. The fungicidal composition as claimed in claim 1, wherein a component (1) and a component (2) in a weight ratio of from 100:1 to 1:100.
8. Use of the fungicidal composition as claimed in claim 1 or claim 6, for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi.
9. The use of the fungicidal composition as claimed in claim 8, wherein said diseases of crops/ phytopathogenic fungi are Alternaria species, for example Alternaria solanv, Erysiphe spp. (e.g. Erysiphe cichoracearum ); Pyricularia species, for example Pyricularia oryzae Septoria species, for example Septoria nodorum, Puccinia spp. (rusts) on various plants, in particular P. triticina (brown or leaf rust), . striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust), on cereals selected from wheat, barley or rye, P. coronata (crown rust of grasses including oats) on cereals, such as e. g. wheat, barley or rye, and Puccinia sorghi (common rust) on maize, Puccinia polysora (southern rust) on maize, and P. helianthi (sunflower rust); Puccinia melanocephala ('Brown rust' in sugarcane); Hemileia vastatrix and Hemileia coffeicola (leaf rust and grey rust of coffee) Hemileia vastatrix (Coffee rust); Uromyces spp. on various crops; and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
10. The use of the fungicidal composition as claimed in claim 1 or claim 6, for treating seed, seed of transgenic plants and transgenic plants.
11. A seed comprising the fungicidal composition as claimed in claim 1, or claim 6.
12. A method for controlling or preventing infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein said fungicidal composition as claimed in claim 1 or 6, is applied to the plants, to parts thereof or to a locus thereof.
13. A method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with said fungicidal composition as claimed in claim 1 or 6.
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