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WO2022130188A1 - Agrochemical composition comprising piperidine thiazole compounds - Google Patents

Agrochemical composition comprising piperidine thiazole compounds Download PDF

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Publication number
WO2022130188A1
WO2022130188A1 PCT/IB2021/061678 IB2021061678W WO2022130188A1 WO 2022130188 A1 WO2022130188 A1 WO 2022130188A1 IB 2021061678 W IB2021061678 W IB 2021061678W WO 2022130188 A1 WO2022130188 A1 WO 2022130188A1
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WO
WIPO (PCT)
Prior art keywords
iii
methyl
phenyl
trifluoromethyl
oxadiazol
Prior art date
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PCT/IB2021/061678
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English (en)
French (fr)
Inventor
Santosh Shridhar AUTKAR
Gajanan SHANBAUG
Ravikumar Suryanarayana SARAGUR
Hagalavadi M VENKATESHA
Original Assignee
Pi Industries Ltd.
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Publication of WO2022130188A1 publication Critical patent/WO2022130188A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides

Definitions

  • the present invention relates to a novel agrochemical composition. More particularly, the present invention relates to a novel agrochemical composition which comprises one or more piperidin thiazole compounds of formula (I) as a component (1) and one or more fungicidally active compounds (II) and/or one or more insecticidally or nematicidally active compounds (III) as a component (2).
  • the present invention relates to a method for controlling microorganisms such as phytopathogenic fungi and bacteria, and/or insect pests and mites, 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 seed.
  • microorganisms such as phytopathogenic fungi and bacteria, and/or insect pests and mites
  • WO2008013622, WO2008013925, WO2009094407, WO2009094445, WO2011076699, WO2013037768, WO2018/193387, WO2019048988, WO2019048989 and WO2021094905 disclose derivatives as fungicides.
  • WO2017138069, WO2013127704, WO200955514 disclose the fungicide mixtures comprising at least one piperidine thiazole derivative and a further selected known fungicide. Combinations of fungicides are often used to facilitate disease control and to retard resistance development.
  • the novel agrochemical compositions according to the invention not only bring about the additive enhancement of the spectrum of action with respect to phytopathogens to be controlled, that was in principle to be expected, but also achieve 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 less or 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 low or virtually no activity; advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage and light stability; advantageous residue formation; improved toxicological or eco-toxicological behavior; improved properties of so called plant physiological effects, for example better growth, increased yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, better plant compatibility as well as mobilization of the defense system of the plant
  • the use of the novel agrochemical compositions according to the invention contributes 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.
  • 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.
  • 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.
  • R 1 is selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 - alkoxy, C 1 -C 6 -alkylthio and C 3 -C 6 -cycloalkyl;
  • A represents C or N; provided that not more than two A represent nitrogen simultaneously;
  • G represents C(R ′ )2 or O; wherein R ′ is selected from the group consisting of hydrogen, halogen, and C 1 -C 3 -alkyl;
  • R 2 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 - haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl and C 1 -C 6 alkylsulfonyloxy;
  • n represents integers of 0-3 and
  • the present invention provides a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, and/or insect pests and mites, 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).
  • unwanted microorganisms such as unwanted fungi and bacteria, and/or insect pests and mites
  • 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 C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, 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-methylp
  • 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
  • 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 C 1 -C 3 -haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1- bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2- dichloro
  • 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.
  • alkoxy used either alone or in compound words included C 1 -C 6 alkoxy.
  • alkoxy examples 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.
  • 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.
  • 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.
  • 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 NaHSO 4 and KHSO 4 .
  • 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 phospho
  • 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 preferred 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 component (1) as at least one compound of formula (I), wherein R 1 is selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and C 3 -C 6 -cycloalkyl; A represents C or N; provided that not more than two A represent nitrogen simultaneously; G represents C(R ′ ) 2 or O; wherein R ′ is selected from the group consisting of hydrogen, halogen, and C 1 -C 3 -alkyl; R 2 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C1- C6-haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl and C 1 -C
  • the novel agrochemical composition according to the present invention comprises at least one fungicidally active compound (II) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, (II-B) Inhibitors of the respiratory chain at complex I or II, (II-C) Inhibitors of the respiratory chain at complex III, (II-D) Inhibitors of the mitosis and cell division, (II-E) Compounds capable of having a multisite action, (II-I) Inhibitors of the cell wall synthesis, (II-J) Inhibitors of the lipid and membrane synthesis, (II-L) Inhibitors of the nucleic acid synthesis,(II-N) Compounds capable of acting as uncoupler, (II-O) Other fungicides, (II-P) HDAC inhibitors (II-Q) Compounds capable to act as a safener, or (II-R) Biological fungicides.
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, (II-B) Inhibitors of the respiratory chain at complex I or II, (II-C) Inhibitors of the respiratory chain at complex III, (II-D) Inhibitors of the mitosis and cell division, (II-E) Compounds capable of having a multisite action, (II-I) Inhibitors of the cell wall synthesis, (II-J) Inhibitors of the lipid and membrane synthesis, (II-L) Inhibitors of the nucleic acid synthesis, (II-N) Compounds capable of acting as uncoupler, (II-O) Other fungicides, (II-P) HDAC inhibitors, or (II-R) Biological fungicides.
  • fungicidally active compound II
  • component (2) selected from the following groups:
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, (II-B) Inhibitors of the respiratory chain at complex I or II, (II-C) Inhibitors of the respiratory chain at complex III, (II-D) Inhibitors of the mitosis and cell division, (II-E) Compounds capable of having a multisite action, (II-I) Inhibitors of the cell wall synthesis, (II-J) Inhibitors of the lipid and membrane synthesis, (II-L) Inhibitors of the nucleic acid synthesis, (II-N) Compounds capable of acting as uncoupler, or (II-O) Other fungicides.
  • fungicidally active compound (II) as component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, (II-B) Inhibi
  • the novel agrochemical composition according to the invention comprises at least one insecticidally or nematicidally active compound (III) as a component (2) selected from the following groups: (III-B) GABA-gated chloride channel blockers, (III-C) Sodium channel modulators, (III-D) Nicotinic acetylcholine receptor (nAChR) competitive modulators, (III-E) Nicotinic acetylcholine receptor (nAChR) allosteric modulators – Site I, (III-F) Glutamate-gated chloride channel (GluCl) allosteric modulators, (III-G) Juvenile hormone mimics, (III-I) Chordotonal organ TRPV channel modulators, (III-K) Microbial disruptors of insect midgut membranes, (III-M) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, (III-V) Voltage-dependent sodium channel blockers, (III-Z) Ryan
  • the novel agrochemical composition according to the invention comprises at least one insecticidally or nematicidally active compound (III) as a component (2) selected from the following groups: (III-B) GABA-gated chloride channel blockers, (III-D) Nicotinic acetylcholine receptor (nAChR) competitive modulators, and (III-Z) Ryanodine receptor-modulators.
  • III-B GABA-gated chloride channel blockers
  • nAChR Nicotinic acetylcholine receptor
  • R-Z Ryanodine receptor-modulators
  • the novel agrochemical composition according to the invention comprises the compound of formula (I), comprising as component (1), wherein R 1 is selected from the group consisting of halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 - alkoxy, C 1 -C 6 -alkylthio and C 3 -C 6 -cycloalkyl; A represents C or N; provided that not more than two A represnt nitrogen simultaneously; G represents C(R ′ ) 2 or O; wherein R ′ is selected from the group consisting of hydrogen, halogen, and C 1 -C 3 -alkyl; R 2 is selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 - haloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl and C 1
  • the compound of formula (I) is selected from the group consisting of (I-1) 1-(4-(4-(5-(2, 6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3- (trifluoromethyl) pyrazin-2-yl) oxy)ethan-1-one; (I-2) 1-(4-(4-(4-(5-(2-chloro-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3- (trifluoromethyl) pyridin-2-yl) oxy)ethan-1-one; (I-3) tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-y
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, for example, (II-A001) cyproconazole, (II-A002) difenoconazole, (II-A003) epoxiconazole, (II-A004) fenhexamid, (II-A005) fenpropidin, (II-A006) fenpropimorph, (II-A007) fenpyrazamine, (II-A008) fluquinconazole, (II-A009) flutriafol, (II-A010) imazalil, (II-A011) imazalil sulfate, (II-A012) ipconazole, (II-A013) metconazole, (II-A014) my
  • amyloliquefaciens strain FZB24 (II-R005) Bacillus amyloliquefaciens strain MBI600, (II-R006) Bacillus amyloliquefaciens strain D747, (II-R007) Bacillus amyloliquefaciens strain D727, (II-R008) Bacillus amyloliquefaciens strain ENV503, (II-R009) Tricoderma atroviride strain SC1, (II-R010) Bacillus mycoides isolate, (II-R011) Pseudomonas chlororaphis strain AFS009, (II-R012) Streptomyces lydicus strain WYEC108, (II-R013) Aureobasidium pullulans strain DSM 14940 + Pullulans strain DSM 14941, (II-R014) extract from Melameuca alternifolia, (II-R015) Swinglea glut
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, for example, (II-A001) cyproconazole, (II-A002) difenoconazole, (II-A003) epoxiconazole, (II-A004) fenhexamid, (II-A005) fenpropidin, (II-A006) fenpropimorph, (II-A007) fenpyrazamine, (II-A008) fluquinconazole, (II-A009) flutriafol, (II-A010) imazalil, (II-A011) imazalil sulfate, (II-A012) ipconazole, (II-A013) metconazole, (II-A01), (II-
  • amyloliquefaciens strain FZB24 (II-R005) Bacillus amyloliquefaciens strain MBI600, (II-R006) Bacillus amyloliquefaciens strain D747, (II-R007) Bacillus amyloliquefaciens strain D727, (II-R008) Bacillus amyloliquefaciens strain ENV503, (II-R009) Tricoderma atroviride strain SC1, (II-R010) Bacillus mycoides isolate, (II-R011) Pseudomonas chlororaphis strain AFS009, (II-R012) Streptomyces lydicus strain WYEC108, (II-R013) Aureobasidium pullulans strain DSM 14940 + Pullulans strain DSM 14941, (II-R014) extract from Melameuca alternifolia, (II-R015) Swinglea glut
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, for example, (II-A002) difenoconazole, (II-A021) tebuconazole, (II-A081) mefentrifluconazole; (II-B) Inhibitors of the respiratory chain at complex I or II, for example, (II-B001) benzovindiflupyr, (II-B003) boscalid, (II-B005) fluopyram, (II-B007) fluxapyroxad; (II-C) Inhibitors of the respiratory chain at complex III, for example, (II-C001) ametoctradin, (II- C002) amisulbrom, (II-C003) azoxystrobin, (II-C006) c
  • II-A
  • III-FF1003 Bacillus thuringiensis subsp. kurstaki, (III-FF1004) Beauveria bassiana, (III-FF1005) Burkholderia sp., (III-FF1006) Chromobacterium subtsugae, (III- FF1007) Chromobacterium subtsugae sp. nov., (III-FF1008) Isaria fumosorosea, (III-FF1009) Lecanicillium longisporum, (III-FF1010) Lecanicillium muscarium (formerly Verticillium lecanii), (III- FF1011) Metarhizium anisopliae, (III-FF1012) Metarhizium anisopliae var.
  • the novel agrochemical composition according to the invention comprises at least one insecticidally or nematicidally active compound (III) as a component (2) selected from the following groups: (III-B) GABA-gated chloride channel blockers, selected from the class of (III-B1) Cyclodiene organochlorines, for example, (III-B1001) chlordane , (III-B1002) endosulfan; (III-B2) Phenylpyrazoles (fiproles), for example, (III-B2001) ethiprole, (III-B2002) fipronil, (III-B2003) flufiprole, (III-B2004) pyrafluprole, (III-B2005) pyriprole; (III-C) Sodium channel modulators, selected from the class of (III-C1) Pyrethroids/Pyrethrins , for example, (III-C1001) acrinathrin, (III-C1002) allethrin
  • the novel agrochemical composition according to the invention comprises at least one insecticidally or nematicidally active compound (III) as a component (2) selected from the following groups: (III-B) GABA-gated chloride channel blockers, selected from the class of (III-B2) Phenylpyrazoles (fiproles), for example, (III-B2002) fipronil; (III-D) Nicotinic acetylcholine receptor (nAChR) competitive modulators, selected from the class of (III-D1) Neonicotinoids, for example, (III-D1002) clothianidin, (III-D1004) imidacloprid, (III-D1007) thiamethoxam, and (III-Z) Ryanodine receptor-modulators, selected from the class of (III-Z1) Diamides, for example, (III-Z1002) chlorantraniliprole, (III-Z1003) cyantraniliprole, (III-Z1005)
  • III-B G
  • the novel agrochemical composition according to the invention comprises at least one fungicidally active compound (II) and/or at least one insecticidally or nematicidally active compounds (III) as a component (2) selected from the following groups: (II-A) Inhibitors of the sterol biosynthesis, for example, (II-A002) difenoconazole, (II-A021) tebuconazole, (II-A081) mefentrifluconazole; (II-B) Inhibitors of the respiratory chain at complex I or II, for example, (II-B001) benzovindiflupyr, (II- B003) boscalid, (II-B005) fluopyram, (II-B007) fluxapyroxad; (II-C) Inhibitors of the respiratory chain at complex III, for example, (II-C001) ametoctradin, (II-C002) amisulbrom, (II-A)
  • All named mixing partners of the classes (II-A) to (II-R) and/or (III-A) to (III-GG) can, if their functional groups enable this, optionally form salts with suitable bases or acids.
  • a component (1) or a component (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).
  • the agrochemical composition according to the invention comprises at least one fungicidally active compound (II) as a component (2) selected from mancozeb, folpet, fosetyl- aluminium, metiram, dithianon, mefenoxam, cyazofamid, amisulbrom, cymoxanil, fluazinam, propamocarb, zoxamide, ethaboxam, fluopicolide, ametoctradin, famoxadone, dimethomorph, valifenalate, difenoconazole, mefentrifluconazole, azoxystrobin, pyraclostrobin, trifoxystrobin, fenamidone, fluopyram, boscalid, chlorothalonil, propineb, copper sulfate, copper hydroxide, copper oxychloride, oxathiapiprolin, fluoxapiprolin, benthia
  • the agrochemical composition according to the invention comprises at least one insecticidally or nematicidally active compound (III) as a component (2) selected from imidacloprid, clothianidin, thiamethoxam, fipronil, chlorantraniliprole, cyantraniliprole, and tetraniliprole.
  • insecticidally or nematicidally active compound (III) as a component (2) selected from imidacloprid, clothianidin, thiamethoxam, fipronil, chlorantraniliprole, cyantraniliprole, and tetraniliprole.
  • component (1) is compound of formula (I) and component (2) selected from the groups (III-A1001) to (III- FF1023) as defined herein:
  • component (1) is a compound of formula (I) and component (2) is selected from the compounds (II-A001) to (II-R047) as defined herein (component 2, for example, (II-A001) or cyproconazole, in combination [(I)+(II-A001)]).
  • component (1) is a compound of formula (I) and component (2) is selected from the compounds (III-A1001) to (III- FF1023) as defined herein (component 2, for example, (III-A1001) or alanycarb, in combination [(I)+(III-A1001)]).
  • the weight ratio of component (1) to component (2) is between 5000:1 and 1:5000 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2. In one embodiment, the weight ratio of component (1) to component (2) is between 1000:1 and 1:1000 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2.
  • the weight ratio of component (1) to component (2) is between 500:1 and 1:500 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2. In one embodiment, the weight ratio of component (1) to component (2) is between 100:1 and 1:100 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2.
  • the weight ratio of component (1) to component (2) is between 50:1 and 1:50 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2. In one embodiment, the weight ratio of component (1) to component (2) is between 20:1 and 1:20 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2.
  • the weight ratio of component (1) to component (2) is between 5:1 and 1:5 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2. In one embodiment, the weight ratio of component (1) to component (2) is between 3:1 and 1:3 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2.
  • the weight ratio of component (1) to component (2) is between 2:1 and 1:2 in combinations [(I)+(II-A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2. In one embodiment, the weight ratio of component (1) to component (2) is 1:1 in combinations [(I)+(II- A001)] to (I)+(II-R047)] or [(I)+(III-A1001) to (I)+(III- FF1023)] of Table 1 and Table 2.
  • component (1) is a compound (I-1) and component (2) is selected from the groups (III-A1001) to (III- FF1023) as defined herein:
  • component (1) is a compound (I-1) and component (2) is selected from the compounds (II-A001) to (II-R047) as defined herein (component 2, for example, (II-A001) or cyproconazole, in combination [(I-1)+(II-A001)]).
  • component (1) is a compound (I-1) and component (2) is selected from the compounds (III-A1001) to (III-FF1023) as defined herein (component 2, for example, (III-A1001) or alanycarb, in combination [(I-1)+(III-A1001)]).
  • the weight ratio of component (1) to component (2) is between 1000:1 and 1:1000 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4. In one embodiment, the weight ratio of component (1) to component (2) is between 500:1 and 1:500 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4.
  • the weight ratio of component (1) to component (2) is between 100:1 and 1:100 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4. In one embodiment, the weight ratio of component (1) to component (2) is between 50:1 and 1:50 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4.
  • the weight ratio of component (1) to component (2) is between 20:1 and 1:20 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4. In one embodiment, the weight ratio of component (1) to component (2) is between 5:1 and 1:5 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4.
  • the weight ratio of component (1) to component (2) is between 3:1 and 1:3 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4. In one embodiment, the weight ratio of component (1) to component (2) is between 2:1 and 1:2 in combinations [(I-1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4.
  • the weight ratio of component (1) to component (2) is 1:1 in combinations [(I- 1)+(II-A001)] to (I-1)+(II-R047)] or [(I-1)+(III-A1001) to (I-1)+(III-FF1023)] of Table 3 and Table 4.
  • component (1) is a compound of formula (I) and component (2) is selected from compounds (II-A001)] to )+(II-R047) as defined herein.
  • component (1) is compound (I-1) and component (2) selected from compounds (II-A001)] to )+(II-R047) as defined herein.
  • component (1) is compound (I-1) and component (2) selected from compounds (II-A001)] to )+(II-R047) as defined herein.
  • component (1) is a compound of formula (I) and component (2) selected from compounds (I-1)+(III-A1001) to (I-1)+(III-FF1023) as defined herein. (I)+(III-B2002), (I)+(III-D1002), (I)+(III-D1004), (I)+(III-D1007), (I)+(III-Z1002), (I)+(III-Z1003), (I)+(III-Z1005). More preferably, following combinations listed in Table 8, wherein, component (1) is compound (I-1) and component (2) selected from compounds (I-1)+(III-A1001) to (I-1)+(III-FF1023) as defined herein.
  • the agrochemical compositions according to the present invention are a mixture of one active compound of formula (I) as component (1) with at least one active component (2).
  • the agrochemical compositions according to the invention are a mixture of one active compound of formula (I) as component (1) with two fungicidally active compounds (II) as a components (2) or with two insecticidally or nematicidally active compounds (III) as components (2) or with one fungicidally active compound (II) and one insecticidally or nematicidally active compound (III) as a components (2).
  • the agrochemical compositions according to the invention is a mixture of one active compound of formula (I) as component (1) with one fungicidally active compound (II) as a component (2) and a further active component (3) or with one insecticidally or nematicidally active compound (III) as a component (2) and a further active component (3), for example, a) one or more compounds having acaricidal, algicidal, avicidal, bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal, rodenticidal, or virucidal properties; or (b) one or more compounds that are antifeedants, bird repellents, chemosterilants, herbicide safeners, insect attractants, insect repellents, mammal repellents, mating disrupters, plant activators, plant growth regulators, or synergists; The compounds (II) and/or compounds (III) of component (2)
  • the agrochemical compositions according to the invention are a mixture of one active compound of formula (I) as component (1) with three fungicidally active compounds (II) as components (2) or with three insecticidally or nematicidally active compounds (III) as components (2).
  • the mixture according to the invention is a mixture of one active compound of formula (I) as component (1) with two fungicidally active compounds (II) as a component (2) and a further active component (3) or with two insecticidally or nematicidally active compounds (III) as a component (2) and a further active component (3), for example, compound of formula (I) as component (1) + two active components (2) as selected from two fungicidally active compounds (II)/ two insecticidally or nematicidally active compounds (III) + a further active component (3) as described herein (4-way mixture).
  • the agrochemical compositions according to the present invention are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes, insects and nematodes.
  • the novel agrochemical compositions according to the invention have a potent microbicidal activity and/or insecticidal or nematicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria and/or insect pests and mites. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases and/or for controlling insect pests and mites) or for protecting materials (e.g. industrial materials, timber, storage goods).
  • 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 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.
  • all plants and plant parts can be treated.
  • 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.
  • 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.
  • the novel agrochemical compositions according to the invention which 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 and improving the quality of the harvested material. They can preferably be used as crop protection compositions.
  • locus thereof includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • Control or “Controlling” as used herein encompasses curative and protective treatment of unwanted microorganisms and/or controlling insect pests and mites.
  • the unwanted microorganisms may be pathogenic bacteria or pathogenic fungi, more specifically phytopathogenic bacteria or phytopathogenic fungi.
  • 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.
  • the present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi, 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).
  • 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 symptoms 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.
  • 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 technology, 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.
  • Ribesioidae 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., lvloraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Afusaceae sp. (for example banana trees and plantations), Rubiaceae sp.
  • Theaceae 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
  • Umbelliferae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Cicurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion, shallots
  • Papilionaceae sp. for example peas
  • major crop plants such as Gramineae sp.
  • 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
  • Vitaceae sp. Fabacae sp.
  • bean for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • Solanaceae sp. for example potatoes), Chenopodiaceae sp.
  • Cannabaceae sp. (hops); 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 Puccini
  • P. parasitica P. arborescens or P. brassicae
  • Phytophthora species for example Phytophthora infestans, P. palmivora, P. nicotianae, P. capsici
  • Plasmopara species for example Plasmopara viticola
  • Pseudoperonospora species for example Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species for example Pythium ultimum
  • others such as Aphanomyces cochlioides, Labyrinthvia zosterae, Peronosclerospora sorghi and Seierospara graminicola.
  • 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 bid
  • phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), 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 basicola).
  • the novel agrochemical composition according to the invention comprises proportions of component (1) and component (2) that are especially useful for controlling particular fungal diseases. These compositions are considered especially useful for controlling Oomycetes diseases cuased by the pathogens such as Phytophthora infestans, Phytophthora megasperma, Phytophthora parasitica, Phytophthora cinnamomi, Phytophthora capsici, Phytophthora nicotianae, Phythothora palmivora, Pythium aphanidermatum, Plasmopara viticola, Peronospora tabacina, Peronospora parasitica, Peronospora destructor, Peronospora arborescens, Pseudoperonospora cubensis, Pseudoperonospora humuli and Bremia lactucae.
  • pathogens such as Phytophthora infestans, Phytophthora megasper
  • the pesticidal compositions according to the present invention are especially suitable for efficiently combating the following pests: Insects from the order of the lepidopterans (Lepidoptera), for example Acronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp.
  • Chilo suppressalis such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp.
  • Feltia subterranean such as Feltia subterranean; Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp.
  • Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimna separata, Orgyia pseudotsugata, Oria spp., Ostrinia spp.
  • Pseudoplusia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absolutea, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera spp.
  • Atomaria linearis such as Atomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp.
  • Leptinotarsa decemlineata such as Leptinotarsa decemlineata; Limonius californicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani, Melolontha melolontha, Migdolus spp., Monochamus spp.
  • Phyllotreta chrysocephala such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis; Stemechus spp.
  • Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp.
  • Anopheles albimanus such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp.
  • Chrysomya bezziana such as Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysops atlanticus, Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia anthropophaga, Culex spp.
  • Lucilia caprina such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscinella spp. such as Oscinella frit; Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp.
  • Phorbia antiqua Phorbia brassicae, Phorbia coarctata
  • Prosimulium mixtum Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletis pomonella
  • Sarcophaga spp. such as Sarcophaga haemorrhoidalis
  • Simulium vittatum Stomoxys spp. such as Stomoxys calcitrans
  • thrips such as Tabanus atratus, Tabanus bovinus, Tabanus lineola, Tabanus similis; Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp., thrips (Thysanoptera), e.g. Basothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp.
  • Thisanoptera e.g. Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp.
  • Calotermes flavicollis Coptotermes formosanus, Heterotermes aureus, Heterotermes Iongiceps, Heterotermes tenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp. such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalensis, cockroaches (Blattaria-Blattodea), e.g.
  • Aphis fabae such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossulariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecola; Arboridia apicalis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp.
  • Dysaphis plantaginea such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as Dysdercus cingulatus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as Empoasca fabae, Empoasca solana; Eriosoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integriceps; Euscelis bilobatus, Euschistus spp.
  • Euschistuos heros such as Euschistuos heros, Euschistus impictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyomorpha halys; Heliopeltis spp., Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp.
  • Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum avenae, Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiella spp., Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp.
  • Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.
  • Pseudococcus comstocki such as Pseudococcus comstocki; Psylla spp. such as Psylla mali, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp.
  • Rhopalosiphum pseudobrassicas such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis, Stephanitis nashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp.
  • Thyanta perditor such as Thyanta perditor; Tibraca spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii,ants, bees, wasps, sawflies (Hymenoptera), e.g.
  • Atta capiguara Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp.
  • Amblyomma spp. e.g. Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum
  • Argas spp. e.g. Argas persicus
  • Boophilus spp. e.g. Boophilus annulatus, Boophilus decoloratus, Boophilus microplus
  • Dermacentor silvarum, Dermacentor andersoni Dermacentor variabilis
  • Hyalomma spp. e.g. Hyalomma truncatum
  • Ixodes spp. e.g.
  • Sarcoptes spp. e.g. Sarcoptes scabiei
  • Eriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus
  • Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.
  • Eotetranychus spp. Eutetranychus spp.
  • Oligonychus spp. Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae
  • Bryobia praetiosa Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasates lycopersici
  • Araneida e.g.
  • Geophilus spp. Scutigera spp. such as Scutigera coleoptrata; millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp., Earwigs (Dermaptera), e.g. forficula auricularia,lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis; Linognathus spp.
  • Linognathus vituli such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., springtails (Collembola), e.g. Onychiurus ssp. such as Onychiurus armatus.
  • the mixtures according to the present invention are also suitable for efficiently controlling nematodes: Plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelenchoides besseyi; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus lignicolus M
  • Examples of further pests which may be controlled by the pesticidal mixture of the present invention include: from the class of the Bivalva, for example, Dreissena spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncom elania spp., Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lumbricoides, Ascaris spp., Brugia malayi, Brugia timori, unostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp
  • Haemonchus contortus such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichiura, Wuchereria bancrofti; from the order of the Isopoda, for example
  • Diloboderus abderus such as Diloboderus abderus; Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta, Leptocorsia oratorius, Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocis latipes, Murgantia spp., Mythemina separata, Neoca
  • Orseolia oryzae such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp., Procornitermes triacifer, Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas, Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.
  • Sesamia inferens such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta derogata, Telehin licus, and Trichostrongylus spp.
  • insects preferably sucking or piercing insects such as insects from the genera Thysanoptera, Diptera and Hemiptera
  • chewing- biting pests such as insects from the genera of Lepidoptera and Coleoptera, in particular the following species: Thysanoptera: Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, Diptera, e.g.
  • Lepidoptera in particular: Agrotis ipsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis
  • the mixtures of the present invention are particularly useful for controlling insects from the order of Coleoptera, in particular Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp
  • the agrochemical compositions of the present invention are particularly useful for controlling insects/mites of the orders Acarina, Coleoptera, Diptera, Hymenoptera, Isoptera, Lepidoptera, Hemiptera, Orthoptera, and Thysanoptera.
  • the agrochemical compositions of the present invention are especially suitable for efficiently combating pests like insects from the order of the lepidopterans (Lepidoptera), beetles (Coleoptera), flies and mosquitoes (Diptera), thrips (Thysanoptera), termites (Isoptera), bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), ants, bees, wasps, sawflies (Hymenoptera), crickets, grasshoppers, locusts (Orthoptera), and also Arachnoidea, such as arachnids (Acarina).
  • the term “mixture” as used herein includes combinations.
  • the present invention also provides methods for controlling insects, acarids, nematodes or phytopathogenic fungi comprising contacting the insect, acarid, nematode or phytopathogenic fungi or their food supply, habitat, breeding grounds or their locus with a pesticidally effective amount of the mixture of the present invention.
  • the present invention also relates to a method of protecting plants from the attack or infestation by insects, acarids, nematodes or phytopathogenic fungi comprising contacting the plant, or the soil or water in which the plant is growing, with a pesticidally effective amount of a mixture of the present invention.
  • the invention also provides a method for the protection of plant propagation material, preferably seeds, from soil insects and seedlings, roots and shoots from soil and foliar insects or fungi, which comprises contacting the plant progagation material as e.g. the seeds before sowing and/or after pregermination with a pesticidally effective amount of a mixture of the present invention.
  • the invention also provides seeds comprising the mixture of the present invention.
  • the invention also provides pesticidal compositions, comprising a liquid or solid carrier and the pesticidal active mixture of the present invention.
  • the invention also relates to the use of the pesticidal compositions for combating insects, acarids, nematodes or phytopathogenic fungi.
  • 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 to control crop diseases which includes grape downy mildew (Plasmopara viticola), late Blight on potato & tomato (Phytophthora infestans), durian/citrus stem canker (Phytophthora palmivora), tobacco black shank (Phytophthora nicotianae), peppers foot rot (Phytophthora capsici), cucurbits downy mildew (Pseudoperonospora cubensis), hops downy mildew (Pseudoperonospora humuli), onion/Leek/shallots (peronospora destructor) cabbage downy mildew (Peronospora parasitica), poppy downy mildew (Peronospora arborescens) lettuce downy mildew (bremia lactucae).
  • grape downy mildew Pullasmopara viticola
  • late Blight on potato & tomato Physical
  • 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, grapevine and various fruits 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 brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp.
  • teleomorph Cochliobolus spp.
  • Southern leaf blight D. maydis
  • Northern leaf blight B. zeicola
  • spot blotch B. sorokiniana
  • Blumeria originally Erysiphe
  • graminis prowdery mildew
  • Cladosporium spp. on tomatoes e.g. C. fulvum: leaf mold
  • cereals e.g. C. herbarum (black ear) on wheat
  • Claviceps purpurea ergot
  • Cochliobolus anamorph: Helmin thosporium of Bipolaris
  • spp. leaf spots
  • corn C. carbonum
  • cereals e.g. C. sativus, anamorph: B. sorokiniana
  • rice e.g. C. miyabeanus, anamorph: H. oryzae
  • Colletotrichum teleomorph: Glomerella
  • Cylindrocarpon spp. e.g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.
  • vines e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease
  • Dematophora teleomorph: Rosellinia necatrix (root and stem rot) on soybeans
  • Diaporthe spp. e.g. D. phaseolorum (damping off) on soybeans
  • Drechslera syn.
  • sabinae rust on pears
  • Helminthosporium spp. syn. Drechslera, teleomorph: Cochliobolus
  • Hemileia spp. e.g. H. vastatrix (coffee leaf rust) on coffee
  • lsariopsis clavispora syn. Cladosporium vitis
  • Macrophomina phaseolina syn. phaseoft
  • root and stem rot on soybeans and cotton
  • Microdochium syn. Fusarium
  • nivale pink snow mold
  • Microsphaera diffusa (powdery mildew) on soybeans
  • Monilinia spp. e.g. M. laxa, M. fructicola and M. fructigena(bloom and twig blight, brown rot) on stone fruits and other rosaceous plants
  • Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas
  • Peronospora spp. downy mildew) on cabbage (e.g. P.
  • brassicae rape
  • rape e.g. P. parasitica
  • onions e.g. P. destructor
  • tobacco P. tabacina
  • soybeans e.g. P. manshurica
  • Phakopsora pachyrhizi and P. meibomiae soybean rust
  • 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. capsic1), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P.
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • 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.
  • P. betae sugar beets
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae
  • Pseudoperonospora downy mildew
  • P. cubensis on cucurbits or P. humili on hop
  • Pseudopezicula tracheiphila red fire disease or, rotbrenner', anamorph: Phialophora) on vines
  • Puccinia spp. rusts
  • 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.
  • R. solani root and stem rot
  • S. solani silk and stem rot
  • S. solani silk blight
  • R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • Rhynchosporium secalis scald
  • 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 prowdery mildew, anamorph: Oidium tucken
  • 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.
  • 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.
  • U. nuda and U. avaenae corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • the novel agrochemical composition of the invention can reduce the mycotoxin content in the harvested material and the food and feed prepared thereof.
  • 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.
  • 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.
  • novel agrochemical composition of the invention can be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the novel agrochemical composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the novel agrochemical composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
  • Timber means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the agrochemical composition of the invention can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • 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 timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • 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, fungi.
  • the agrochemical composition of the invention preferably acts against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes).
  • novel agrochemical composition of the invention may intervene in physiological processes of plants and can therefore also be used as plant growth regulators.
  • Plant growth regulators may exert various effects on plants. The effect of the substances depends essentially on the time of application in relation to the developmental stage of the plant, and also on the amount of active ingredient applied to the plants or their environment and on the type of application.
  • growth regulators should have a particular desired effect on the crop plants like: increased or improved yield is referring to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectoliter 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
  • 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.
  • 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 comprises increased fungal resistance and increased resistance against nematodes, viruses and bacteria.
  • 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 seeds.
  • the invention further provides seeds which have been treated by one of the methods described in the previous paragraph.
  • the inventive seeds are employed in methods for the protection of seeds from unwanted microorganisms. In these methods, seeds treated with at least one inventive agrochemical composition are used.
  • the novel agrochemical composition of the present invention is also suitable for treating seed.
  • the present invention therefore also relates to a method for the protection of seed and germinating plants from the attack by phytopathogenic fungi, by treating the seed with an inventive composition.
  • the invention likewise relates to the use of the inventive compositions for the 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 the 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.
  • 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.
  • the novel agrochemical compositions are suitable for protecting seed 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, sorghum/millet and oats
  • maize cotton, soybean, 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.
  • 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 their habitat.
  • the agrochemical composition typically comprises at least one active compound combination and at least one agriculturally suitable 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.
  • 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. 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.
  • 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, suspo-emulsion concentrates, natural or synthetic products impregnated with the agrochemical composition, fertilizers and also micro-encapsulations 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.
  • 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.
  • compounds may be applied at a rate of 1 to 2000 L/ha, especially from 10 to 1000 L/ha.
  • the novel agrochemical composition can be applied directly, i.e.
  • compositions 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: US4272417, US4245432, US4808430, US5876739, US20030176428, WO2002080675, WO2002028186.
  • the novel agrochemical composition usable in accordance with the invention can be converted to the formulations such as, dusts, solutions, suspensions, powders, pastes, a suspension concentrate (SC), a water dispersible granule (WDG)/(WG), a tablet (TB), a wettable powder (WP), a water dispersible tablet (WT), an ultra-low volume (ULV), a liquid (UL), an ultra-low volume (ULV), a suspension (SU), a water soluble powder (SP), a suspo-emulsion (SE), a granule (GR), an emulsifiable granule (EG), an oil-in- water emulsion (EW), an emulsifiable granule (EG), an emulsion oil in water (EO), an emulsifiable powder (EP), an emulsion for seed treatment (ES), a solution for seed treatment (LS), a flowable concentrate for seed treatment (FS), an emulsif
  • 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 agriculturally acceptable additives, for example, customary extenders and also solvent(s) or diluent(s), dye(s), wetting agent(s), dispersant(s), emulsifier(s), antifoam(s), preservative(s), filler(s), thickener(s), adhesive(s), gibberellins, solid carrier(s), liquid carrier(s), gaseous carrier(s), surfactant(s), binder(s), disintegrating agent(s), pH adjuster(s), anti-caking agent(s), penetrant(s), anti- freezing agent(s), defoaming agent(s), extender(s), stabilizer(s) and/or
  • Dyes is selected from the group comprising of, but not limited to, 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.
  • Carrier is is selected from the group comprising of, but not limited to, 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 kaolin’s, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates.
  • typically useful solid carriers for preparing 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.
  • Surfactant is selected from the group comprising of, but not limited to, 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
  • a surfactant is typically used when the compound of 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.
  • Auxiliarie(s) is selected from the group comprising of, but not limited to, 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.
  • Dispersant(s) and/or emulsifier(s) is selected from the group comprising of, but not limited to, 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 is selected from the group comprising of, but not limited to, silicone antifoams and magnesium stearatePreservative(s) is selected from the group comprising of, but not limited to, are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.
  • Thickeners s selected from the group comprising of, but not limited to, cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Adhesive(s) is selected from the group comprising of, but not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Liquid carrier(s) is selected from the group comprising of, but not limited to, water; alcohols such as ethanol, propanol, butanol, n-octanol, isopropanol ethylene glycol, diethylene glycol, propylene glycol, polyethylene glycol, benzyl alcohol, glycerin; polyol ethers such as ethylene glycol monopropyl ether, diethylene glycol monomethyl ether, dipropylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; ethers such as dipropyl ether, dioxane, tetrahydrofuran, aliphatic hydrocarbons such as normal paraffin, isoparaffin, kerosene, mineral oil; aromatic hydrocarbons such as xylene, toluene, naphthene, solvent naphtha, solvent C9, solvent
  • Gaseous carrier(s) is selected from the group comprising of, but not limited to, liquefied petroleum gas, air, nitrogen, carbon dioxide or dimethyl ether. These gaseous carriers may be used alone or in combination thereof.
  • Surfactant(s) are nonionic or anionic surfactants or a combination of these surfactants. It is preferred to use one or more than one kind of surfactant.
  • Surfactant(s) is selected from the group comprising of, but not limited to, sugar esters such as sorbitan monolaurate, polyoxyethylene sorbitan monolaurate; C1-C30 alkylcarboxylate, C1-C20 hydroxyalkylcarboxylate, polymer containing carboxylate, arylcarboxylate, alkylx (e.g., sugar esters such as sorbitan monolaurate, polyoxyethylene sorbitan monolaurate; C1-C30 alkylcarboxylate, C1-C20 hydroxyalkylcarboxylate, polymer containing carboxylate, arylcarboxylate, alkylx (e.g.
  • aliphatic di- and tricarboxylates having 2 to 32 carbon atoms, such as aconitic acid, adipic acid, aspartic acid, citric acid, fumaric acid, galactaric acid, glutamic acid, glutaric acid, oxoglutaric acid, maleic acid, malic acid, malonic acid, oxalate, sebacic acid, succinic acid, tartaric acid; alkyl polyglucoside such as decyl glucoside; polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, or polyoxyethylene coconut fatty alcohol ether; polyoxyethylene alkynyl ether such as polyoxyethylene 2,4,7,9-tetramethyl-5-decyn-4,7-diol ether; polyoxyethylene aryl ethers such as polyoxyethylene nonylphenyl ether or polyoxyethylene tristyrylphenyl ether; polyoxyethylene vegetable oil ethers such as polyoxyethylene castor oil
  • surfactants may be used alone or in combination thereof.
  • surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, dispersants, spreader, adjuvant for penetration enhancement, rain fastness, or soil leaching control etc.
  • Penetrant(s) is selected from the group comprising of, but not limited to, one or more of alcohol, glycol, glycol ether, ester, amine, alkanolamine, amine oxide, quaternary ammonium compound, triglyceride, fatty acid ester, fatty acid ether, N-methyl pyrrolidone, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide, polyoxyethylenetrimethylolpropanemonooleate, polyoxyethylenetrimeth ylolpropanedioleate, polyoxyethylenetrimethylolpropanetrioleate, polyoxyethylenesorbitanmonooleate, polyoxyethylene sorbitol hexaoleate and methylated soybean oil.
  • Solvent(s) is selected from the group comprising of, but not limited to, one or more of C2-C4-alkyl lactates, in particular from glycerin triacetate, ethyl lactate, n-propyl lactate and isopropyl lactate.
  • solvent is selected from C6-C10-alkyl lactates, such as n-hexyl lactate, 1-ethylhexyl lactate, 1-methylhepytyl lactate, 1,3-dimethylhexyl lactate, 2-methylheptyl lactate, 2,4-dimethylhexyllactate, 2,2,4-trimethylpentyl lactate, n-octyl lactate, 2-ethylhexyl lactate, n-nonyl lactate, 1-methyloctyl lactate, 2-methyloctyl lactate, 1-methylnonyl lactate, 2-propylheptyl lactate and n-decyl lactate, 2,2,4- trimethylpentyl lactate, butyl lactate, isopropyl myristate, hexylene glycol, dioxane, d-limonene, a C 1 -C 14 saturated straight-chain alcohol, isopropyl lac
  • Oil(s) is selected from the group comprising of, but not limited to, a light paraffin oil, plant oil, mineral oil, petroleum oil, vegetable oil or animal oil or derivatives or mixtures thereof.
  • a light paraffin oil such as, but not limited to, a light paraffin oil, plant oil, mineral oil, petroleum oil, vegetable oil or animal oil or derivatives or mixtures thereof.
  • Stabilizer(s) is selected from the group comprising of, but not limited to, drying agent such as zeolite, quick lime or magnesium oxide; antioxidant agent such as phenol type, amine type, sulfur type or phosphorus type; or ultraviolet absorber such as salicylic acid type or a benzophenone type; or methylated soybean oil; or peroxide compounds such as hydrogen peroxide and organic peroxides, alkyl nitrites such as ethyl nitrite and alkyl glyoxylates such as ethyl glyoxylate, zeolite, antioxidants such as phenol compounds, phosphoric acid compounds and the like; ultraviolet absorbers such as benzophenone compounds or derivatives thereof.
  • drying agent such as zeolite, quick lime or magnesium oxide
  • antioxidant agent such as phenol type, amine type, sulfur type or phosphorus type
  • ultraviolet absorber such as salicylic acid type or a benzophenone type
  • methylated soybean oil or peroxide compounds such as hydrogen peroxide
  • the novel agrochemical compositions of the present invention can be applied in an amount of from 0.1 g to 100 kg per 100 kg of the seed.
  • the components (1) and components (2) are advantageously present in a synergistically effective weight ratio of components (1): components (2) in a range of 10000:1 to 1:10000, preferably in a weight ratio of 2000:1 to 1:2000 and more preferably in a weight ratio of 1000:1 to 1:1000.
  • the novel agrochemical composition according to the invention the components (1), one or more piperidin thiazole compounds of formula (I) and (2), one or more fungicidally active compounds, are advantageously present in a synergistically effective weight ratio of (1):(2) in a range of 500:1 to 1:5000, preferably in a weight ratio of 200:1 to 1:2000, more preferably in a weight ratio of 100:1 to 1:1000, most preferably in weight ratios of 10:1 to 1:100, 5:1 to 1:50, 2,5:1 to 1:25, 2:1 to 1:20, 1,5:1 to 1:15, 1:1 to 1:10, 1:1 to 1:5, 1:1 to 1:3, 1:1 to 1:2.
  • 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.
  • 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.
  • novel agrochemical compositions of the present invention can be used for treating seed, seed of transgenic plants and seed of genetically modified plants. Further, the novel agrochemical compositions of the present invention can comprise a transgenic trait and a non-transgenic trait. In particular, the novel agrochemical composition is used for foliar application.
  • the expression “combination” stands for the various 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.
  • agrochemical composition means a combination of at least two active compounds and/or with further agriculturally suitable additives, such as agriculturally suitable auxiliaries, e.g. solvents, carriers, surfactants, extenders or the like
  • auxiliaries e.g. solvents, carriers, surfactants, extenders or the like
  • 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 application rate in the case of treatment of plant parts, for example leaves from 0.1 to 10000 g/ha, preferably from 10 to about 3000 g/ha, more preferably from 50 to 1000 g/ha, even more preferably from 80 to 400 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, preferably from 10 to 150 g per 100 kg of seed, more preferably from 12 to 30 g per kg of seeds in the case of soil treatment: from 0.1 to 10000 g/ha, preferably from 1 to 5000 g/ha.
  • 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.
  • component (3) means one or more insecticidal or fungicidal or acaricidal or nematicidal or herbicidal or growth regulator or biostimulant or fertilizer or amino acid compound or combinations thereof.
  • the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound of formula (I) as component (1) and at least one fungicidally active compound (II) selected from the groups (II-A) to (II-R) and/or at least one insecticidally or nematicidally active compound (III) selected from the groups (III-A) to (III-GG) as component (2) as described above, useful for plant protection, and optionally one suitable solvent or solid carrier.
  • fungicidally active compound (II) selected from the groups (II-A) to (II-R)
  • III insecticidally or nematicidally active compound selected from the groups (III-A) to (III-GG) as component (2) as described above, useful for plant protection, and optionally one suitable solvent or solid carrier.
  • combating harmful fungi with a mixture of a compound of formula (I) as component (1) and at least one fungicidally active compound (II) selected from the groups (II- A) to (II-R) and/or at least one insecticidally or nematicidally active compounds (III) selected from the groups (III-A) to (III-GG) as component (2), as described above, is more efficient than combating those fungi and/or insect pests and mites with the individual compounds of formula (I) or individual fungicidally active compound (II) selected from the groups (II-A) to (II-R) or at least one insecticidally or nematicidally active compounds (III) selected from the groups (III-A) to (III-GG).
  • 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) as component (1) and at least one active compound (II) and/or active compound (III) as component (2) and optionally a further active compound as component (3) simultaneously, either jointly (e.g.
  • 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.
  • 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) as component (1) and the component (2) generally depends of the properties of the active components used, usually it is in the range of 1:10000 to 10000:1 , often it is in the range of 1:1000 to 1000:1 and 1:500 to 500:1 and 1:100 to 100:1, regularly in the range of 1:50 to 50:1 , preferably in the range of 1:25 to 25:1 and 1:20 to 20:1 , more preferably in the range of 1:15 to 15:1 and 1:10 to 10:1 and in particular in the range of 1:6 to 6:1, 1:4 to 4:1, 1:2 to 2:1 and 1:1 to 2:1.
  • the weight ratio of the compound of formula (I) as component (1) and the component (2) usually is in the range of 1:1000 to 1:1, often in the range of 1:100 to 1:1, regularly in the range of 1:50 to 1:1, preferably in the range of 1:20 to 1:1 and 1:15 to 1:1 and in particular in the range of 1:10 and 1:8 to 1:2.
  • the weight ratio of the compound of formula (I) as component (1) and the component (2) usually is in the range of 1:1 to 1:1000, often in the range of from 1:1 to 1:100, regularly in the range of 1:1 to 1:50, preferably in the range of 1:1 to 1:25, 1:1 to 1:20, 1:1 to 1:15, more preferably in the range of 1:1 to 1 :10 and in particular in the range of 1:1 to 1:8 and 1:1 to 1:5 .
  • the ternary mixtures i.e.
  • compositions according to the invention comprising the compound of formula (I) as component (1) and a compound of formula (II) and/or a compound of formula (III) as component (2), the weight ratio of component (1) to compound of formula (II) is in the range of 1:100 to 1:1, regularly in the range of 1:50 to 1:1, preferably in the range of 1:25 to 1:1, more preferably in the range of from 1:15 to 1:1 and in particular in the range of 1:5 to 1:1, and the weight ratio of component (1) to compound of formula (III) is in the range of 1:100 to 1:1, regularly in the range of 1:50 to 1:1, preferably in the range of 1:25 to 1:1, more preferably in the range of 1:10 to 1:1 and in particular in the range of 1:5 to 1:1.
  • the ternary mixtures i.e. compositions according to the invention, comprising the compound of formula (I) as component (1) and compound of formula (II)/ compound of formula (III) as component (2) and a further active compound as component (3)
  • the weight ratio of component (1) to compound of formula (II)/ compound of formula (III) as component (2) is in the range of 1:100 to 1:1, regularly in the range of 1:50 to 1:1, preferably in the range of 1:25 to 1:1, more preferably in the range of from 1:15 to 1:1 and in particular in the range of 1:5 to 1:1
  • the weight ratio of component (1) to component (3) is in the range of 1:100 to 1:1, regularly in the range of 1:50 to 1:1, preferably in the range of 1:25 to 1:1, more preferably in the range of 1:10 to 1:1 and in particular in the range of 1:5 to 1:1.
  • the ternary mixtures comprise as compounds (II) fungicidal compounds that are independently of each other selected from the groups (II-A), (II-B), (II-C), (II-D), (II-E), (II- F), (II-G), (II-H), (II-I), (II-J), (II-K), (II-L), (II-M), (II-N), (II-O), (II-P), (II-Q), and (II-R),; and wherein the further active component (3) is not identical with the at least one fungicidally active compound (II)/ the at least one insecticidally or nematicidally active compound (III) as component (2).
  • any further active components are, if desired, added in a ratio of 100:1 to 1:5 to the compound of formula (I) as 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.
  • Preferred formulations of agrochemical composition as disclosed in the present invention can have the following compositions (weight %): a) Emulsifiable concentrates: active ingredients: 1 to 75 %, preferably 5 to 25 % surface-active agent(s): 1 to 30 %, preferably 5 to 20 % liquid carrier(s): 1 to 80 %, preferably 1 to 60%
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Dusts active ingredients: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier(s): 99.9 to 90 %, preferably 99.9 to 99 %
  • active ingredients 0.1 to 10 %, preferably 0.1 to 5 % solid carrier(s): 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 ingredients: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent(s): 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.
  • 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 ingredients: 0.5 to 90 %, preferably 1 to 80 % surface-active agent(s): 0.5 to 20 %, preferably 1 to 15 % solid carrier(s): 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.
  • Granules active ingredients: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier(s): 99.5 to 70 %, preferably 97 to 85 %
  • the following examples further illustrate, but do not limit, the invention.
  • seed treatment composition 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.
  • 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.
  • 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) as a component (1) and the component (2) may show a synergistic effect.
  • a synergistic effect of e.g. fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two active compounds can be calculated by using the Colby formulas (COLBY, S.R. "Calculating synergistic and antagonistic responses of herbicide combination", Weeds, Vol.15, pages 20-22; 1967).
  • Colby's formula The expected activity for a given combination of two active compounds (binary composition) can be calculated as follows: 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).
  • the expected activity for a given combination of three active compounds can be calculated as follows: 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.
  • the compounds of formula (I) can be obtained by various routes in analogy to processes and examples disclosed in WO2019048989 and WO2021094905.
  • CHEMISTRY EXAMPLES The following 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 1-(4-(4-(5-(2-chloro-6-fluorophenyl)-4, 5-dihydroisoxazol-3-yl) thiazol-2- yl) piperidin-1-yl)-2-((3-(trifluoromethyl) pyridin-2-yl) oxy) ethan-1-one
  • Step 1 Preparation of 5-(2-chloro-6-fluorophenyl)-3-(2-(piperidin-4-yl) thiazol-4-yl)-4, 5- dihydroisoxazole 2, 2, 2-trifluoroacetate
  • Step 2 Preparation of 1-(4-(4-(5-(2-chloro-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl) piperidin-1-yl)-2-((3-(trifluoromethyl) pyridin-2-yl)oxy)ethan-1-one
  • 5-(2-chloro-6-fluorophenyl)-3-(2-(piperidin-4-yl)thiazol-4-yl)-4,5- dihydroisoxazole (4 g, 10.93 mmol) in dimethylformamide (100 mL), N,N-diisopropylethylamine (13.37 mL, 77 mmol) was added.
  • Example 2 Preparation of 1-(4-(4-(5-(2, 6-dichlorophenyl)-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin-1-yl)-2-((3-(trifluoromethyl) pyrazin-2-yl) oxy) ethan-1-one
  • Step 1 Preparation of 5-(2, 6-dichlorophenyl)-3-(2-(piperidin-4-yl) thiazol-4-yl)-4, 5-dihydroisoxazole
  • tert-butyl 4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl) piperidine- 1-carboxylate 9 g, 18.66 mmol) in dichloromethane (65.9 mL), trifluoroacetic acid (28.7 mL, 373 mmol
  • reaction mixture was stirred at 25 °C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain product 5-(2, 6-dichlorophenyl)-3-(2- (piperidin-4-yl) thiazol-4-yl)-4, 5-dihydroisoxazole (7.13 g, 18.65 mmol, 100 % yield).
  • Step 2 Preparation of 1-(4-(4-(5-(2, 6-dichlorophenyl)-4, 5-dihydroisoxazol-3-yl) thiazol-2-yl) piperidin- 1-yl)-2-((3-(trifluoromethyl) pyrazin-2-yl) oxy) ethan-1-one
  • 2-((3-(trifluoromethyl)pyrazin-2-yl)oxy)acetic acid (2.79 g, 12.56 mmol)
  • N,N-diisopropylethylamine (10.96 mL, 62.8 mmol) was added.
  • reaction mixture was stirred for 5 min.
  • N,N-diisopropylethylamine (10.96 mL, 62.8 mmol) was added and the resulting mixture was stirred at 25 °C for 15 min.
  • the reaction mixture was quenched with cold water; reaction mixture was diluted with cold water (200 mL) and extracted with ethyl acetate (500 mL X 2). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.
  • the temperature of the reaction was raised to 25 °C and the reaction mixture was stirred for 2 h. After completion of the reaction, the reaction mixture was quenched with ice and extracted with ethyl acetate (1 L). The ethyl acetate layer was washed with brine solution. The ethyl acetate layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain 1-bromo-3-fluoro-2-vinylbenzene.
  • Step 2 Preparation of tert-butyl 4-(4-((hydroxyimino) methyl) thiazol-2-yl) piperidine-1-carboxylate
  • hydroxylamine hydrochloride 23.43 g, 337 mmol
  • ethanol 500 mL
  • triethylamine 94 mL, 674 mmol
  • Step 3 Preparation of tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2- yl)piperidine-1-carboxylate
  • tert-butyl (E)-4-(4-((hydroxyimino)methyl)thiazol-2-yl)piperidine-1-carboxylate 4.0 g, 12.85 mmol
  • 1-bromo-3-fluoro-2-vinylbenzene (2.58 g, 12.85 mmol) in ethyl acetate (50 mL) was added at 25 °C.
  • N-Chlorosuccinimide (2.57 g, 19.27 mmol), sodium bicarbonate (3.24 g, 38.5 mmol) and water (10 mL) were added.
  • the resulting mixture was stirred at 60 °C for 2 h.
  • the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL X 3). The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtaine a crude product.
  • Example 1 Alternaria solani test on tomato plants
  • the single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 mL.
  • the test solutions were poured into spray bottles for further applications.
  • 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.
  • the plants were inoculated with a spore suspension containing 0.24x10 6 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 single 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. The results are shown for the compound of formula (I-1) in Table A.
  • Table A The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Alternaria solani in tomato are shown in the table below:
  • Example 2 Phytophthora infestans test on tomato plants The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in 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 sporangial suspension (cold sterile water containing 0.24x10 6 Phytophthora infestans inoculum).
  • a sporangial suspension cold sterile water containing 0.24x10 6 Phytophthora infestans inoculum.
  • Table B The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Phytophthora infestans in tomato are shown in the table below: Ob d E t d/ d ( ) ( )
  • Example 3 Erysiphe cichoracearum on cucumber plants The single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 mL.
  • test solutions were poured into spray bottles for further applications.
  • 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.
  • the plants were inoculated with a conidial suspension containing 2x10 5 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 single 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. The results are shown for the compound of formula (I-1) in Table C.
  • Table C The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Erysiphe cichoracearum in cucumber are shown in the table below:
  • Example 4 Pseudoperonospora cubensis on cucumber plants The single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50ml.
  • test solutions were poured into the spray bottles for further applications.
  • 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 hallow cone nozzles.
  • the plants were inoculated with a conidial spore suspension containing 2x10 4 Pseudoperonospora cubensis inoculum.
  • the inoculated plants were then kept in a greenhouse chamber at 23°C temperature & 80-90 % relative humidity for disease expression.
  • a visual assessment of the performance of the single 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. The results are shown for the compound of formula (I-1) in Table D1 and Table D2.
  • Table D-1 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Pseudoperonospora cubensis in cucumber are shown in the table below:
  • Table D-2 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Pseudoperonospora cubensis in cucumber are shown in the table below:
  • Example 5 Phakopsora pachyrhizi test on soybean plants
  • the single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to the desired test concentration in a calibrated spray volume of 50 ml.
  • the test solutions were poured into spray bottles for further applications.
  • 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.
  • the plants were inoculated with a suspension containing 2 x10 5 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 single 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. The results are shown for the compound of formula (I-1) in Table E1 and Table E2.
  • Table E-1 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Phakopsora pachyrhizi in soybean are shown in the table below: b 12
  • Table E-2 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Phakopsora pachyrhizi test in Soybean are shown in the table below:
  • Example 6 Rhizoctonia solani test on rice plants The single compounds or compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration
  • test solutions were poured into spray bottles for further applications.
  • healthy young rice seedling/ 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.
  • the plants were inoculated with an equal quantity of infected rice bran containing Rhizoctonia solani.
  • the inoculated plants were then kept in a greenhouse chamber at 24-25 °C temperature and 90-95 % relative humidity for disease expression.
  • a visual assessment of the performance of the single compounds and 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 controls. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting. The results are shown for the compound of formula (I-1) in Table F1 and Table F2.
  • Table F-1 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Rhizoctonia solani in rice are shown in the table below:
  • Table F-2 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Rhizoctonia solani in rice are shown in the table below: 0
  • Example 7 Pyricularia oryzae test on rice plants The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 m
  • test solutions were poured into spray bottles for further applications.
  • 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.
  • the plants were inoculated with a spore suspension containing 1.4x10 6 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 single 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 combinations were calculated by comparing the disease rating in the treatment with the one of the untreated controls. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting. The results are shown for the compound of formula (I-1) in Table G.
  • Table G The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Pyricularia oryzae in rice are shown in the table below:
  • Example 8 Botrytis cinerea test on tomato plants The single compounds or compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications.
  • Table H The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups ((II-A) to (II-R) against Botrytis cinerea in tomato are shown in the table below:
  • Example 9 Parastagonospora nodorum/ Septoria nodorum/ Stagnospora nodorum on wheat plants
  • the single compounds or compound combinations were dissolved in 2% DMSO/ Acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 mL.
  • the spray solutions were poured into spray bottles for further applications.
  • 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.
  • the plants were inoculated with a suspension containing 2.8x10 6 Stagnospora nodorum inoculum.
  • the inoculated plants were then 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 single compounds and respective 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. The results are shown for the compound of formula (I-1) in Table I1 and Table I2.
  • Table I-1 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (II-A) to (II-R) against Septoria nodorum in wheat are shown in the table below:
  • Table I-2 The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Septoria nodorum in wheat are shown in the table below: Insecticidal activity: As described herein, the compounds of formula (I) show insecticidal activities which are exerted with respect to numerous insect pests and mites, which attacks on important agricultural crops.
  • Example A Helicoverpa armigera on tomato
  • the leaf dip method was used for testing, wherein the required quantity of the compound or respective compound combinations was weighed and dissolved in a tube containing solvent solution. The tube was put on a vortex at 2000 rpm for 90 min for proper mixing, and then diluted with 0.01% Triton-X solution to get the desired test concentration. Tomato leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then transferred into the cells of bioassay trays. A single second instar larva was released into each cell and the tray was covered with a lid.
  • Table J The synergistic insecticidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Helicoverpa armigera on tomato are shown in the table below:
  • Example B Plutella xylostella on cabbage The leaf dip method was used for testing, wherein the required quantity of the compound or respective compound combinations was weighed and dissolved in a tube containing solvent solution.
  • the tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then diluted with 0.01% Triton-X solution to the desired test concentration.
  • Cabbage leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then transferred into the cells of bioassay trays.
  • a single second instar larva was released into each cell and the tray was covered with a lid.
  • the bio-assay trays were then kept under laboratory conditions at a temperature of 25 °C and a relative humidity of 70%. Observations on dead, moribund and alive larvae were recorded 72 h after the release. Percent mortality was calculated by combining dead and moribund larvae and comparing the result to the one of the untreated control.
  • Table K The synergistic insecticidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Plutella xylostella are shown in the table below:
  • Example C Myzus persicae on capsicum The leaf dip method was used for testing, wherein the required quantity of the single compounds or respective compound combinations was weighed and dissolved in a tube containing solvent solution.
  • the tube was put on a vortex at 2000 rpm for 90 min for proper mixing, then, diluted with 0.01% Triton-X solution to the desired test concentration.
  • Capsicum leaves were dipped in the compound solution for 10 seconds, shade dried for 20 min and then placed, with the abaxial side of the leaf up, in single cells of a bio-assay tray containing 4 ml of a solidified 1 % agar-agar solution.
  • Known numbers of third instar nymphs, collected in petri plates, were released into each cell with a treated leaf and the cell was covered with a perforated lid for better aeration.
  • the trays were kept in a plant growth chamber at a temperature of 25 °C and a relative humidity of 70%.
  • Table L The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compound of formula (I) is particularly compound (I-1) as component (1) and other components (2) selected from the groups (III-A) to (III-GG) against Myzus persicae on capsicum are shown in the table below:

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