compositions, use of a composition, method for combating fungi and plant propagation material

专利摘要:
COMPOSITIONS, USE OF A COMPOSITION, METHOD FOR FIGHTING FUNGI AND MATERIAL FOR PROPAGATION OF VEGETABLES. The present invention relates to compositions comprising a specific triazole compound (from I- to I-13) as component I and one of oxatiapiproline, triadimenol, sulfoxaflor, methiocarb, cypermethrin, thiodicarb, triflumezopyrim (mesoionic) and flupyradifurone as component II . The present invention also refers to the use of the compositions for combating phytopathogenic fungi, a method for combating phytopathogenic fungi, as well as the plant propagation material coated with the compositions.
公开号:BR112016030116B1
申请号:R112016030116-1
申请日:2015-06-15
公开日:2021-07-06
发明作者:Frederik Menges；Martin Semar；Lutz Brahm；Annette Schuster；Florent MAZUIR
申请人:BASF Agro B.V.；
IPC主号:

专利说明:

FIELD OF THE INVENTION
[001] The present invention relates to compositions comprising: (1) as component I, a compound selected from: - compound I-1: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]- 1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol; - compound I-2: 1-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol; - compound I-3: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-4: 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol; - compound I-5: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol; - compound I-6: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pent-3-ynyl]-1,2,4-triazole; - compound I-7: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol; - compound I-8: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1,2,4-triazole; - compound I-9: 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-propyl]-1,2,4-triazole; - compound I-10: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol; - compound I-11: 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1,2,4-triazole; - compound I-12: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-3,3-dimethyl-butyl]-1,2,4-triazole; - compound I-13: 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-butyl]1,2,4-triazole; - compound I-14: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol; - compound I-15: 1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-pent-3-ynyl]-1,2,4-triazole; - compound I-16: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)but-3-yn-2-ol; - compound I-17: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-18: 2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-19: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol; - compound I-20: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxypropyl]-1,2,4-triazole; - compound I-21: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-butyl]-1,2,4-riazol; - compound I-22: 1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxypentyl]-1,2,4-triazole; - compound I-23: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,1,1-trifluoro-3-(1,2,4-triazol-1-yl)propan-2- ol; - compound I-24: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-fluoro-1-(1,2,4-triazol-1-yl)butan-2-ol hydrochloride; - compound I-25: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-4-yn-2-ol; - compound I-26: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-27: 2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-28: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol; - compound I-29: and 2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-30: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol; and - compound I-31: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol; - and (2) as component II, a compound selected from the group of: - oxatiapiproline (II-1); triadimenol (II-2); sulfoxaflor (II-3); methiocarb (II-4); cypermethrin (II-5); thiodicarb (II-6); triflumezopyrim (mesoionic) (II-7) and flupyradifurone (II-8).
[002] In particular, the present invention relates to compositions comprising: (1) as component I, a compound selected from: - compound I-1: 2-[2-chloro-4-(4-chlorophenoxy) phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol; - compound I-2: 1-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol; - compound I-3: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; - compound I-4: 1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol; - compound I-5: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol; - and (2) as component II, a compound selected from the group of: - oxatiapiproline (II-1); triadimenol (II-2); sulfoxaflor (II-3); methiocarb (II-4); cypermethrin (II-5); thiodicarb (II-6); triflumezopyrim (mesoionic) (II-7) and flupyradifurone (II-8).
[003] The present invention further refers to the use of the compositions of the present invention as pesticides, in particular, for the control of phytopathogenic fungi, as described herein in detail, and the preparations or compositions comprising them. The present invention further relates to seeds comprising the compositions. The present invention further relates to methods for controlling pests, in particular phytopathogenic fungi as described in detail, wherein the fungi or materials, plants, soil or seed to protect from fungal attack are treated with an effective amount of compositions according to the present invention. The present invention further relates to processes for preparing the compositions according to the present invention.
[004] With the object of reducing application rates and broadening the activity spectrum of known compounds, it was an object of the present invention to provide compositions that, at a reduced total amount of active compounds applied, show an improved activity against important pests , in particular, phytopathogenic fungi, in particular, for certain indications. It was further an object to provide compositions that are useful for the control of specific pathogens in important specific crops that are often susceptible to attack by pathogens.
[005] Consequently, the compositions and uses defined at the beginning and in the following description were discovered. BACKGROUND OF THE INVENTION
[006] Compounds I (component I) can be obtained by various routes in analogy to known prior art processes (see J.Agric. Food Chem. (2009) 57, 4,854-4,860; EP patents 0.275. 955 A1; DE 40 03 180 A1, EP 0.113.640 A2, EP 0.126.430 A2). Furthermore, compounds I (component I), their preparation and use in crop protection are described in the publications WO 2013/007767 (PCT / EP 2012/063626), WO 2013/024076 (PCT / EP 2012/065835), WO 2013/024075 (PCT / WO 2013/024077 (PCT / EP 2012/065847), WO 2013/024081 (PCT / EP 2012/065848), WO 2013/024081 (PCT / EP 2012/065848) WO 2013/010862 ( PCT / EP 2012/063,526), WO 2013/010894 (PCT / EP 2012/063,635), WO 2013/010885 (PCT / EP 2012/063620), WO 2013/024082 (PCT / EP 2012/065,850)), which also describe certain compositions with other active compounds. Due to the basic character of its nitrogen atoms, component I, that is, in particular, compound I-1, I-2, I-3, I-4, I-5, I-6, I-7, I-8, I-10, I-11, I12, I-13, I-14, I-15, I-16, I-17, I-18, I-19, I-21, I-22, I-23, I-24, I-25, I-26, I-27, I-28, I-29, I-30 and I-31 or any group of compounds I described in detail above is capable of forming salts or adducts with inorganic or organic acids or with metal ions, in particular salts with inorganic acids. BRIEF DESCRIPTION OF THE INVENTION
[007] I-1: 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-







[008] Examples of inorganic acids are hydrogenated acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
[009] Suitable organic acids, for example, are formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid and other arylcarboxylic acids, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids that have a straight chain or branched alkyl radicals with 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl). and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids that have straight chain or branched alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphoric acid radicals), where the alkyl or aryl radicals can carry another and the substituents, for example, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, and the like. Suitable metal ions, in particular, are the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminum, tin and lead, and also the elements of the groups of transition from 1 to 8, in particular, chromium, manganese, iron, cobalt, nickel, copper, zinc, and others. Special preference is given to the metallic ions of the elements of the fourth period transition groups. Metals can be present in the different valences they can assume.
[010] The components I comprise the chiral centers and that, in general, are obtained in the form of racemates. The R and S enantiomers of the compounds according to the present invention can be separated and isolated in pure form with methods known to the person skilled in the art, for example using chiral HPLC. Suitable for use as antimicrobial agents are enantiomers and their compositions. This correspondingly applies to compositions. Furthermore, components that may be present in different crystal modifications, which may differ in biological activity.
[011] In particular, in each case, a racemic composition is present. Furthermore, any other proportions of the (R)-enantiomer and (S)-enantiomer may be present in accordance with the present invention. This applies to all compositions described in detail in the present.
[012] According to an embodiment of the present invention, component I is compound I-1. Compound I-1 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-1.
[013] According to a specific embodiment, compound I-1 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[014] According to an even more specific embodiment, compound I-1 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99% .
[015] Compound (R)-I-1: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent- 3-in-2-ol; compound (S)-I-1: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-in -2-ol. According to another embodiment of the present invention, component I is compound I-2. Compound I-2 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-2.
[016] According to a specific embodiment, compound I-2 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[017] According to a further specific embodiment, compound I-2 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[018] Compound (R)-I-2: (R)-1-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1- yl)ethanol; compound (S)-I-2: (S)-1-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol .
[019] According to yet another embodiment of the present invention, component I is compound I-3. Compound I-3 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-3.
[020] According to a specific embodiment, compound I-3 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[021] According to another specific embodiment, compound I-3 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[022] Compound (R)-I-3: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) propan-2-ol; compound (S)-I-3: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2 -l.
[023] According to yet another embodiment of the present invention, component I is compound I-4. Compound I-4 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-4.
[024] According to a specific embodiment, compound I-4 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[025] According to another specific embodiment, compound I-4 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[026] Compound (R)-I-4: (R)-1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol- 1-yl)ethanol; compound (S)-I-4: (S)-1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl )ethanol.
[027] According to yet another embodiment of the present invention, component I is compound I-5. Compound I-5 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-5.
[028] According to a specific embodiment, compound I-5 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[029] According to another specific embodiment, compound I-5 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[030] Compound (R)-I-5: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol- 1-yl)butan-2-ol; compound (S)-I-5: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl )butan-2-ol.
[031] According to yet another embodiment of the present invention, component I is compound I-6. Compound I-6 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-6.
[032] According to a specific embodiment, compound I-6 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[033] According to a further specific embodiment, compound I-6 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[034] Compound (S)-I-6: (S)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pent-3-ynyl]-1,2 ,4-triazole; compound (R)-I-6: (R)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pent-3-ynyl]-1,2,4- triazole.
[035] According to yet another embodiment of the present invention, component I is compound I-7. Compound I-7 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-7.
[036] According to a specific embodiment, compound I-7 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[037] According to another specific embodiment, compound I-7 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[038] Compound (S)-I-7: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) butan-2-ol; compound (R)-I-7: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2 -l.
[039] According to yet another embodiment of the present invention, component I is compound I-8. Compound I-8 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-8.
[040] According to a specific embodiment, compound I-8 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[041] According to a further specific embodiment, compound I-8 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[042] Compound (S)-I-8: (S)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1,2 ,4-triazole; compound (R)-I-8: (R)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1,2,4- triazole.
[043] According to yet another embodiment of the present invention, component I is compound I-9. Compound I-9 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-9.
[044] According to a specific embodiment, compound I-9 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[045] According to another specific embodiment, compound I-9 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[046] Compound (S)-I-9: (S)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-propyl]-1,2,4 -triazole; compound (R)-I-9: (R)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-propyl]-1,2,4-triazole.
[047] According to yet another embodiment of the present invention, component I is compound I-10. Compound I-10 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-10.
[048] According to a specific embodiment, compound I-10 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[049] According to another specific embodiment, the compound I-10 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[050] Compound (S)-I-10: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3,3-dimethyl-1-(1,2,4-triazol- 1-yl)butan-2-ol; compound (R)-I-10: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3,3-dimethyl-1-(1,2,4-triazol-1-yl )butan-2-ol.
[051] According to yet another embodiment of the present invention, component I is compound I-11. Compound I-11 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-11.
[052] According to a specific embodiment, compound I-11 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[053] According to another specific embodiment, compound I-11 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[054] Compound (S)-I-11: (S)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1 ,2,4-triazole; compound (R)-I-11: (R)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-cyclopropyl-2-methoxy-ethyl]-1,2, 4- triazole.
[055] According to yet another embodiment of the present invention, component I is compound I-12. Compound I-12 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-12.
[056] According to a specific embodiment, compound I-12 is provided and used as (R)-enantiomer with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[057] According to another specific embodiment, compound I-12 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[058] Compound (S)-I-12: (S)-2-[2-trifluoromethyl-4-(4-chlorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1- il)propan-2-ol; compound (R)-I-12: (R)-2-[2-trifluoromethyl-4-(4-chlorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1-yl)propan - 2-ol.
[059] According to yet another embodiment of the present invention, component I is compound I-13. Compound I-13 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-13.
[060] According to a specific embodiment, compound I-13 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[061] According to another specific embodiment, compound I-13 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[062] Compound (S)-I-13: (S)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-butyl]1,2,4- triazole; compound (R)-I-13: (R)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-butyl]1,2,4-triazole.
[063] According to yet another embodiment of the present invention, component I is compound I-14. Compound I-14 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-14.
[064] According to a specific embodiment, compound I-14 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[065] According to a further specific embodiment, compound I-14 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[066] Compound (S)-I-14: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) pent-3-yn-2-ol; compound (R)-I-14: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pent-3 -in-2-ol.
[067] According to yet another embodiment of the present invention, component I is compound I-15. Compound I-15 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-15.
[068] According to a specific embodiment, compound I-15 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[069] According to another specific embodiment, compound I-15 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[070] Compound (S)-I-15: (S)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-pent-3-ynyl]-1 ,2,4-triazole; compound (R)-I-15: (R)-1-[2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-methoxy-pent-3-ynyl]-1,2, 4-triazole.
[071] According to yet another embodiment of the present invention, component I is compound I-16. Compound I-16 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-16.
[072] According to a specific embodiment, compound I-16 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[073] According to another specific embodiment, compound I-16 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[074] Compound (S)-I-16: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) but-3-yn-2-ol; compound (R)-I-16: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)but-3 -in-2-ol.
[075] According to an embodiment of the present invention, component I is compound I-17. Compound I-17 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-17.
[076] According to a specific embodiment, compound I-17 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[077] According to another specific embodiment, compound I-17 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[078] Compound (R)-I-17: (R)-12-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan- 2-ol; compound (S)-I-4: (S)-12-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol .
[079] According to another embodiment of the present invention, component I is compound I-18. Compound I-18 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-18.
[080] According to a specific embodiment, compound I-18 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[081] According to another specific embodiment, compound I-18 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[082] Compound (S)-I-18: (S)-2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan- 2-ol; compound (R)-I-18: (R)-2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol .
[083] According to yet another embodiment of the present invention, component I is compound I-19. Compound I-19 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-19.
[084] According to a specific embodiment, compound I-19 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[085] According to a further specific embodiment, compound I-19 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[086] Compounds (S)-I-19: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1- yl)butan-2-ol; compounds (R)-I-19: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan -2-ol.
[087] According to yet another embodiment of the present invention, component I is compound I-20. Compound I-20 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-20.
[088] According to a specific embodiment, compound I-20 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[089] According to another specific embodiment, compound I-20 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[090] Compound (S)-I-20: (S)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-propyl]-1,2,4-triazole ; compound (R)-I-20: (R)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-propyl]-1,2,4-triazole.
[091] According to yet another embodiment of the present invention, component I is compound I-21. The compound I-21 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-21.
[092] According to a specific embodiment, compound I-21 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[093] According to another specific embodiment, compound I-21 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[094] Compound (S)-I-21: (S)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-butyl]-1,2,4-triazole ; compound (R)-I-21: (R)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-butyl]-1,2,4-triazole.
[095] According to yet another embodiment of the present invention, component I is compound I-22. Compound I-22 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-22.
[096] According to a specific embodiment, compound I-22 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[097] According to another specific embodiment, compound I-22 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[098] Compound (S)-I-22: (S)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pentyl]-1,2,4-triazole ; compound (R)-I-22: (R)-1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-methoxy-pentyl]-1,2,4-triazole.
[099] According to yet another embodiment of the present invention, component I is compound I-23. Compound I-23 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-23.
[0100] According to a specific embodiment, compound I-23 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0101] According to a further specific embodiment, compound I-23 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0102] Compound (S)-I-23: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,1,1-trifluoro-3-(1,2,4- triazol-1-yl)propan-2-ol; compound (R)-I-23: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1,1,1-trifluoro-3-(1,2,4-triazol-1 -yl)propan-2-ol.
[0103] According to yet another embodiment of the present invention, component I is compound I-24. Compound I-24 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg, the enantiomer pure (R) or the pure (S) enantiomer of I-24.
[0104] According to a specific embodiment, compound I-24 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0105] According to another specific embodiment, compound I-24 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0106] Compound (S)-I-24: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-fluoro-1-(1,2,4-triazol-1) hydrochloride -yl)butan-2-ol; compound (R)-I-24: hydrochloride (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-fluoro-1-(1,2,4-triazol-1-yl) butan-2-ol.
[0107] According to yet another embodiment of the present invention, component I is compound I-25. Compound I-25 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of pure (S) of I-25.
[0108] According to a specific embodiment, compound I-25 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0109] According to a further specific embodiment, compound I-25 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0110] Compound (S)-I-25: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent- 4-in-2-ol; compound (R)-I-25: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-4-in -2-ol.
[0111] According to yet another embodiment of the present invention, component I is compound I-26. Compound I-26 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-26.
[0112] According to a specific embodiment, compound I-26 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0113] According to another specific embodiment, compound I-26 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0114] Compound (S)-I-26: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1- il)propan-2-ol; compound (R)-I-26: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1-yl)propan -2-ol.
[0115] According to yet another embodiment of the present invention, component I is compound I-27. Compound I-27 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-27.
[0116] According to a specific embodiment, compound I-27 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0117] According to another specific embodiment, compound I-27 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0118] Compound (S)-I-27: (S)-2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1- il)propan-2-ol; compound (R)-I-27: (R)-2-[2-chloro-4-(4-fluorophenoxy)phenyl]-1-methoxy-3-(1,2,4-triazol-1-yl)propan -2-ol.
[0119] According to yet another embodiment of the present invention, component I is compound I-28. Compound I-28 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-28.
[0120] According to a specific embodiment, compound I-28 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0121] According to another specific embodiment, the compound I-28 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0122] Compound (S)-I-28: (S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) pentan-2-ol; compound (R)-I-28: (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2 -l.
[0123] According to yet another embodiment of the present invention, component I is compound I-29. Compound I-29 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-29.
[0124] According to a specific embodiment, compound I-29 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0125] According to another specific embodiment, the compound I-29 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0126] Compound (S)-I-29: (S)-2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl) propan-2-ol; compound (R)-I-29: (R)-2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2 -l.
[0127] According to yet another embodiment of the present invention, component I is compound I-30. Compound I-30 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-30.
[0128] According to a specific embodiment, compound I-30 is provided and used as (R) enantiomer with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0129] According to a further specific embodiment, compound I-30 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0130] Compound (S)-I-30: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan- 2-ol; compound (R)-I-30: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol .
[0131] According to yet another embodiment of the present invention, component I is compound I-31. The compound I-31 may be present as the racemic composition of the (R) enantiomer and the (S) enantiomer, but the (R) enantiomer and the (S) enantiomer may also be present in any other proportion, eg the enantiomer pure (R) or the pure (S) enantiomer of I-31.
[0132] According to a specific embodiment, compound I-31 is provided and used as enantiomer (R) with an enantiomeric excess (ee) of at least 40%, e.g. at least 50%, 60% 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98% and even more preferably at least 99%.
[0133] According to a further specific embodiment, the compound I-31 is provided and used as enantiomer (S) with an enantiomeric excess (ee) of at least 40%, for example at least 50%, 60 %, 70% or 80%, preferably at least 90%, more preferably at least 95%, most preferably at least 98% and even more preferably at least 99%.
[0134] Compound (S)-I-31: (S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan- 2-ol; compound (R)-I-31: (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol .
[0135] According to another embodiment of the present invention, component I is selected from compounds I-1, I-2, I-3, I-4, I-5, I-6, I7, I- 8, I-9, I-11, I-13, I-14, I-15 and I-16. According to a more special embodiment of the present invention, component I is selected from compounds I-1, I-2, I-6 and I-8. According to another more special embodiment of the present invention, component I is selected from compounds I-3, I4, I-5, I-7, I-9, I-11, I-13, I-14, I-15 and I-16.
[0136] According to yet another embodiment of the present invention, component I is selected from compounds I-1, I-2, I-3, I-4 and I-5, more specifically selected from I -1, I-3, I-4 and I-5. According to yet another embodiment of the present invention, component I is selected from compounds I-3, I-4 and I-5.
[0137] The preparation of component II and its action against harmful fungi are known (cf.: http://www.alanwood.net/pesticides/) and are generally commercially available. Commercially available active compounds can be found, for example, in The Pesticide Manual, 14th Edition, British Crop Protection Council (2006) and other publications.
[0138] Oxatiapiproline (II-1): 1-(4-{4-[(5RS)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]- 1,3-thiazol-2-yl}-1-piperidyl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone.
[0139] Triadimenol (II-2): (1RS,2RS;1RS,2SR)-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl )butan-2-ol.
[0140] Sulfoxaflor (II-3): [methyl(oxo){1-[6-(trifluoromethyl)-3-pyridyl]ethyl}- À6-sulfanylidene]cyanamide.
[0141] Methiocarb (II-4): 4-methylthio-3,5-xylyl methylcarbamate.
[0142] Cypermethrin (II-5): (1S,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (RS)-α-cyano-3-phenoxybenzyl or (1RS) (RS)-α-cyano-3-phenoxybenzyl )-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate.
[0143] Thiodicarb (II-6): (3EZ,12EZ)-3,7,9,13-tetramethyl-5,11-dioxa-2,8,14-trithia-4,7,9,12-tetraazapentadeca- 3,12-dien-6,10-dione.
[0144] Triflumezopyrim (mesoionic) (II-7): 3,4-dihydro-2,4-dioxo-1-(pyrimidin-5-ylmethyl)-3-(α,α,α-trifluoro-m-tolyl) -2H-pyrido[1,2-a]pyrimidin-1-ium-3-ide.
[0145] Flupyradifurone (II-8): 4-[(6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino]furan-2(5H)-one.
[0146] In another embodiment, component II is selected from the group of oxatiapiproline (II-1); triadimenol (II-2); sulfoxaflor (II-3); methiocarb (II-4); thiodicarb (II-6); triflumezopyrim (mesoionic) (II-7) and flupyradifurone (II-8).
[0147] In one embodiment, component II is selected from the group of oxatiapiproline (II-1); triadimenol (II-2); sulfoxaflor (II-3); metiocarb (II-4) and triflumezopyrim (mesoionic) (II-7).
[0148] Next, the compositions of the present invention and their preferred uses are further described. In each case, according to the present invention, the use of the composition for the control of a special pest, in particular, the phytopathogenic fungus is also intended to encompass the respective method for the control of phytopathogenic fungi, in particular, in which the fungi or the materials, vegetables, soil or seed to be protected from fungal attack are treated with an effective amount of a composition as defined herein.
[0149] According to a specific embodiment of the present invention, only two active compounds as defined are present in the compositions of the present invention (hereinafter also called "binary compositions"). The composition of course may contain any type of additive or the like as described in detail below, in order to provide a formulation suitable for agricultural use.
[0150] The weight ratio of component I to component II depends on the properties of the active substances used and is usually in the range from 1:1000 to 1000:1, more especially from 1:500 to 500:1. The weight ratio of component I to component II in general depends on the properties of the active substances used and is usually in the range from 1:100 to 100:1, often in the range from 1:50 to 50 :1, preferably in the range from 1:20 to 20:1, especially more preferably in the range from 1:10 to 10:1, especially in the range from 1:3 to 3 :1. It may also be preferable that the weight ratio is in the range from 1:2 to 2:1.
[0151] According to still other embodiments of the two-component compositions according to the present invention, the weight ratio of component I to component II normally ranges from 1:1 to 1:100, regularly, in the range from 1:1 to 1:50, preferably in the range from 1:1 to 1:20, most preferably, in the range from 1:1 to 1:10, most further preferably in the range from 1:1 to 1:4 and especially in the range from 1:1 to 1:2.
[0152] According to one embodiment, the two-component compositions according to the present invention preferably can have weight ratios of compound I to compound II in the range from 1000:1 to 1:1, often in the range from 100:1 to 1:1, usually in the range from 50:1 to 1:1, preferably in the range from 20:1 to 1:1, most preferably in the range from 10:1 to 1:1, more preferably in the range from 4:1 to 1:1 and especially in the range from 2:1 to 1:1.
[0153] The specific compositions of the invention are compiled in Table B1, in which each line corresponds to a realization of the compositions, according to the present invention, that is, a specific individualized composition. According to a specific aspect, these are binary compositions that each only contain these two components as active compounds. Furthermore, each combination of the individual compositions in this Table also represents the embodiments of the present invention. TABLE B1
[0154] Two-component compositions from B1-1 to B1-248 comprising a component I and a component II, in particular binary compositions containing the respective components I and II as only active ingredients: - I = component I selected a from compounds I-1 to I-31; - II = oxatiapiproline (II-1); triadimenol (II-2); sulfoxaflor (II-3); methiocarb (II-4); cypermethrin (II-5); thiodicarb (II-6); triflumezopyrim (mesoionic) (II-7) and flupyradifurone (II-8).






[0155] The weight ratio of component I to component II in compositions B1-1 to B1-248 depends on the properties of the active substances used and is usually in the range from 1:1000 to 1000:1, more especially, from 1:500 to 500: 1. The weight ratio of component I to component II in compositions B1-1 to B1-248 may preferably be in the range from 1:100 to 100:1 often in the range from 1:50 to 50: 1, preferably in the range from 1:20 to 20: 1, especially preferably in the range from 1:10 to 10: 1, in especially, in the range from 1:3 to 3:1. It may also be preferable that the weight ratio is in the range from 1:2 to 2:1.
[0156] According to still other embodiments of compositions B1-1 to B1-248, according to the present invention, the weight ratio of component I to component II normally ranges from 1:1 to 1 :100 regularly in the range from 1:1 to 1:50, preferably in the range from 1:1 to 1:20, more preferably in the range from 1:1 to 1:10 even more preferably in the range from 1:1 to 1:4 and especially in the range from 1:1 to 1:2.
[0157] According to another embodiment, compositions B1-1 to B1-248, according to the present invention, preferably may have weight ratios of component I to compound II in the range from 1,000: 1 to 1:1, often in the range from 100:1 to 1:1, regularly in the range from 50:1 to 1:1, preferably in the range from 20:1 to 1: 1, more preferably in the range from 10:1 to 1:1, even more preferably in the range from 4:1 to 1:1 and especially in the range from 2:1 to 1:1.
[0158] An embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1000:1 to 1:1000.
[0159] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 500:1 to 1:500.
[0160] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 100:1 to 1:100.
[0161] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:100 to 100:1.
[0162] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:50 to 50:1.
[0163] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:20 to 20:1.
[0164] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:10 to 10:1.
[0165] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:3 to 3:1.
[0166] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:2 to 2:1.
[0167] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1000:1 to 1:1.
[0168] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 100:1 to 1:1.
[0169] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 50:1 to 1:1.
[0170] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 20:1 to 1:1.
[0171] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 10:1 to 1:1.
[0172] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 4:1 to 1:1.
[0173] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 2:1 to 1:1.
[0174] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1000.
[0175] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:100.
[0176] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:50.
[0177] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:20.
[0178] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:10.
[0179] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:4.
[0180] Another embodiment of the present invention relates to any of the compositions B1-1 to B1-248 wherein the weight ratio of component I to component II is from 1:1 to 1:2.
[0181] As described in detail above, components I contain the centers of chirality and therefore may be present as racemic mixtures, as pure enantiomers or in the two enantiomers of a component I which may be present in any ratio (S) :(R).
[0182] According to the special embodiments of the present invention, the respective component I is present as (S)-enantiomer. According to special embodiments of the present invention, the respective component I is present as (R)-enantiomer. According to a specific aspect, these are binary compositions that each only contain these two components as active compounds.
[0183] The compositions according to the present invention are suitable as fungicides. They are distinguished by excellent efficacy against a broad spectrum of phytopathogenic fungi, including soil fungi, which are mainly derived from the classes of Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes (Deuteromycetes) . Fungi imperfecti). Some are systemically effective and can be used in crop protection, such as foliar fungicides, seed coating fungicides and soil fungicides. Furthermore, they are suitable for combating harmful fungi, which occur, inter alia, in wood or in plant roots.
[0184] The compositions according to the present invention are especially important for the control of a variety of pathogenic fungi in various cultivated vegetables, such as cereals, for example, wheat, rye, barley, triticale, oats or rice ; sugar beet, for example sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or currants; legumes, such as lentils, peas, alfalfa or soybeans; oleaginous vegetables, such as rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor oil vegetables, oil palms, ground nuts or soy; cucurbits, such as pumpkins, cucumbers or melon; fiber vegetables such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruit and mandarins; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, pumpkins or paprika; lauraceous vegetables such as avocado, cinnamon or camphor; vegetables for raw materials and energy, such as corn, soy, rapeseed, sugar cane or palm oil; corn; tobacco; nuts; coffee; tea; the vines (table grapes and grape juice from vines); hop; lawn, sweet leaf (also called Stevia); natural rubber vegetables or ornamental and forestry vegetables, such as flowers, shrubs, broad-leaved or evergreen trees, for example, conifers, and in vegetable propagation material such as seeds, and culture material of these vegetables.
[0185] Preferably, the compositions of the present invention are used to control a multitude of fungi in crops, such as potato, sugar beet, tobacco, wheat, rye, barley, oat, rice, corn, cotton, soybean , rapeseed, vegetables, sunflower, coffee or sugar cane; fruits; vineyards; ornamental vegetables; or vegetables such as cucumbers, tomatoes, beans or pumpkins.
[0186] The term "vegetable propagation material" is to be understood as denoting all generative parts of the vegetable, such as seeds and vegetative plant material such as grafts and tubers (eg potatoes), which can be used for vegetable multiplication. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, stems, shoots and other parts of plants, including seedlings and young plants, which will be transplanted after germination or after emergence from the ground. These young vegetables can also be protected prior to transplanting from a full or partial treatment through dipping or dumping.
[0187] Preferably, the treatment of plant propagation materials with the compounds of the present invention and the compositions of the present invention, respectively, is used for the control of a multiplicity of fungi in cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
[0188] The term “cultivated vegetables” is to be understood to include plants that have been modified through reproduction, mutagenesis or genetic engineering, including but not limited to agricultural biotech products on the market or under development (cf. http://cera- gmc.org/, see GM crop database). Genetically modified plants are plants in which the genetic material has been modified in this way, through the use of recombinant DNA techniques that under natural circumstances cannot easily be obtained through cross-breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant to improve certain properties of the plant. Such genetic modifications also include, but are not limited to targeted post-transient modification of the protein(s), oligo- or polypeptides, for example, through glycosylation or polymer addition such as the prenylated, acetylated or farnesylated moieties or PEG portions.
[0189] Plants that have been modified through reproduction, mutagenesis, or genetic engineering, for example, have become tolerant to applications of specific classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) herbicides; acetolactate synthetase (ALS) inhibitors such as the sulfonyl ureas (see, for example, US publications 6,222,100, WO 2001/82685, WO 2000/26390, WO 1997/41218, WO 1998/02526, WO 1998/ 02527, WO 2004/106529, WO 2003/14357, WO 2003/13225, WO 2003/14356, WO 2004/16073) or the imidazolinones (see, for example, US publications 6,222,100, WO 2001/82685, WO 2000/ 026390, WO 1997/41218, WO 1998/002526, WO 1998/02527, WO 2004/106529, WO 2005/20673, WO 2003/014357, WO 2003/13225, WO 2003/14356, WO 2004/16073); 5-enolpyruvylshikimate-3-phosphate synthetase (EPSPS), such as glyphosate (see, for example, publication WO 1992/00377); glutamine synthetase (GS) inhibitors such as glufosinate (see for example EP-A 242 236, EP-A 242 246) or oxynyl herbicides (see for example US patent 5,559,024) as a result conventional methods of reproduction or genetic engineering. Several cultivated vegetables have been made tolerant to herbicides through conventional breeding methods (mutagenesis), eg Clearfield® summer rape (Canola, BASF SE, Germany), being tolerant to imidazolinones, eg imazamox. Genetic engineering methods are used to make cultivated vegetables such as soybeans, cotton, corn, beets and rapeseed tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade name RoundupReady® ( glyphosate tolerant, Monsanto, USA) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
[0190] In addition, the vegetables also covered are those that, through the use of recombinant DNA techniques, are capable of synthesizing one or more insecticidal proteins, especially those known from Bacillus genus bacteria, especially from Bacillus thuringiensis , such as the δ-endotoxins, for example, CryIA(b), CryIA(c), CrylF, CrylF(a2), CryllA(b), CryllA, CryllB(b1) or Cry9c; vegetative insecticidal proteins (VIP), for example, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematode colonizing bacteria, for example, Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other specific neurotoxins from other insects, toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins or barley; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patin, cystatin or papain inhibitors, ribosome inactivation proteins (RIP) such as ricin, maize RIP, abrin, luphine, saporin or briodine, steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone or HMG-CoA-reductase inhibitors, ion channel blockers, such as such as sodium or calcium channel blockers; juvenile hormonal esterase, diuretic hormone receptors (helicokinin receptors); stilbene synthetase, bibenzyl synthetase, chitinases or glucanases. In the context of the present invention, these insecticidal proteins or toxins are expressly understood also as pre-toxins, truncated or hybrid proteins, otherwise modified proteins. Hybrid proteins are characterized by a novel combination of protein domains, (see, for example, publication WO 2002/015701). Other examples of such genetically modified toxins or plants capable of synthesizing such toxins are described, for example, in publications EP-A 374753, WO 1993/007278, WO 1995/34656, EP-A 427.529, EP-A 451.878, WO 2003 /18810 and WO 2003/52073. Methods for the production of such genetically modified vegetables are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants provide the plants that produce these proteins, tolerance to pests of all taxonomic groups of arthropods, especially beetles (Coeloptera), bialated insects (Diptera) and moths (Lepidoptera) and nematodes (Nematoda) . Genetically modified vegetables capable of synthesizing one or more insecticidal proteins, for example, are described in the publications mentioned above, and some are commercially available, such as YieldGard® (maize cultivars that produce the toxin Cry1Ab), YieldGard® Plus ( corn cultivars that produce the toxins Cry1Ab and Cry3Bb1), Starlink® (corn cultivars that produce the toxin Cry9c), Herculex® RW (maize cultivars that produce Cry34Ab1, Cry35Ab1 and the enzyme Phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars that produce the toxin Cry1Ac), Bollgard® I (cotton cultivars that produce the toxin Cry1Ac), Bollgard® II (cotton cultivars that produce the toxins Cry1Ac and Cry2Ab2); VipCot® (cotton cultivars that produce the VIP toxin); NewLeaf® (potato cultivars that produce Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (eg Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (maize cultivars producing Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize cultivars producing a modified version of the Cry3A toxin, cf publication WO 2003/018810), MON 863 from Monsanto Europe SA, Belgium (maize cultivars which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton cultivars that produce a modified version of the Cry1Ac toxin) and 1,507 from Pioneer Overseas Corporation, Belgium (maize cultivars that produce the Cry1F toxin and PAT enzyme).
[0191] In addition, the plants also covered, are those that through the use of recombinant DNA techniques, are able to synthesize one or more proteins to increase the resistance or tolerance of said plants to bacterial, viral and fungal pathogens. Examples of such proteins are so-called “pathogenesis-related proteins” (PR proteins, see for example EP-A 392.225), plant disease resistance genes (eg potato varieties, which express the Resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-Lysozyme (eg potato cultivars capable of synthesizing these proteins, with increased resistance against bacteria such as Erwinia amylvora). Methods for the production of such genetically modified vegetables are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
[0192] In addition, the vegetables also covered are those that, through the use of recombinant DNA techniques, are capable of synthesizing one or more proteins to increase productivity (for example, biomass production, grain production, content of starch, oil content or protein content), tolerance to aridity, salinity or other environmental factors limiting the growth or tolerance to pests and fungal, viral or bacterial pathogens of these plants.
[0193] In addition, the plants also covered are those that, through the use of recombinant DNA techniques, contain a modified amount of substances of the content or of new substances of the content, specifically to improve human or animal nutrition, for example, oil crops that produce long-chain omega-3 fatty acids or health-promoting omega-9 unsaturated fatty acids (eg Nexera® rapeseed, DOW Agro Sciences, Canada).
[0194] In addition, the plants also covered are those that, through the use of recombinant DNA techniques, contain a modified amount of content substances or new content substances, specifically to improve the production of raw materials, for example, potatoes that produce increased amounts of amylopectin (eg Amflora® potato, BASF SE, Germany).
[0195] The compositions are especially suitable for the control of the following plant diseases: - Albugo spp. (white rust) on ornamental vegetables, legumes (eg A. Candida) and sunflowers (eg A. tragopogonis); Alternaria spec. (Alternaria leaf spot) on vegetables, rapeseed (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (eg A. solani or A. alternata), tomatoes (eg , A. solani or A. alternata) and wheat; Aphanomyces spp. in sugar beets and vegetables; Ascochyta spp. in cereals and vegetables, for example, A. tritici (anthracnose) in wheat and A. hordei in barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp), in maize (e.g., D. maydis) cereals, (e.g. brown spot, B. sorokiniana) in cereals, rice, (e.g., B. oryzae) and lawns; Blumeria (formerly Erysiphe) graminis (powdery mildew) in cereals (eg wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mould) on fruits and berries (eg strawberries), vegetables (eg lettuce, carrots, celery and cabbage), rapeseed, flowers, vines, forest vegetables and wheat; Bremia lactucae (mildew) on lettuce; - Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved and evergreen trees, eg C. ulmi (Dutch elm disease) on elm trees; Cercospora spp. (Cercospora leaf spots) on maize, rice, sugar beets (eg C. beticola), sugar cane, vegetables, coffee, soybeans (eg C. sojina or C. kikuchii) and rice; Cladosporium spp. in tomatoes (eg C. fulvum: leaf mold) and cereals, eg C. herbarum (black dot) in wheat; Claviceps purpurea (ergot) in cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (eg C. sativus, anamorph: B. sorokiniana) and rice (eg C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) in cotton (eg C. gossypii), corn (eg C. graminicola), soft fruits, potatoes (eg C. coccodes: black dots), beans (eg C. Iindemuthianum) and soybeans (for example, C. truncatum or C. gloeosporioides); Corticium spp., for example, C. sasakii (sheath pest) on rice; Corynespora cassiicola (leaf spots) on soybean and ornamental vegetables; Cycloconium spp., for example, C. oleaginum on olive trees; Cylindrocarpon spp. (For example, stone fruit trees or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vineyards (eg C. liriodendri, teleomorph: Neonectria liriodendri: Black foot disease) and ornamental vegetables ; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) in soybean; Diaporthe spp., for example, D. phaseolorum (fall) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. in corn, cereals such as barley (eg D. teres, reticular spot) and wheat (eg D. tritici-repentis: brown spot), rice and peat; Esca (perishing, apoplexy) in vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. in pome fruits (E. Piri.), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entiloma oryzae (leaf charcoal) in rice; Epicoccum spp. (black mold) in wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae.), vegetables (eg E. Pisi), such as cucurbits (eg E. cichoracearum), cabbage, rapeseed (eg E. cruciferarum); Eutypa lata (perishing or Eutypa stone, anamorph: Cytosporina lata, syn Libertella blepharis) in fruit trees, vines and ornamental groves; Exserohilum (syn. Helminthosporium) spp. in corn (eg E. turcicum); Fusarium (teleomorph: Gibberella) spp. (deterioration, root or stem rot) on various vegetables, such as F. graminearum or F. culmorum (root, scab or crown rot) on cereals (eg wheat or barley), F. oxisporum on tomatoes, F. solani (f. sp. Glicinas now F. virguliforme) and F. tucumaniae and F. brasiliense each causing sudden death syndrome in soybean, and F. verticillioides in corn; Gaeumannomyces graminis (all) in cereals (eg wheat or barley) and maize; Gibberella spp. in cereals (eg G. zeae) and rice (eg G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruit and other vegetables and G. gossypii on cotton; grain color complex in rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on pink and juniper vegetables, for example, G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) in corn, cereals and rice; Hemileia spp., for example, H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli), (root and stem rot) in soybean and cotton; Microdochium (syn. Fusarium) nivale (snow pink mold) in cereals (eg wheat or barley); Microsphaera diffusa (powdery mildew) in soybean; Monilinia spp., for example M. laxa, M. fructicola and M. fructigena (flower and branch rust, brown rot) on stone fruits and other pink vegetables; Mycosphaerella spp. in cereals, bananas, soft fruits and ground nuts, such as M. graminicola (anamorph: Septoria tritici, Septoria spot) in wheat or M. fijiensis (Black Sigatoka) in bananas; Peronospora spp. (mildew) in cabbage (eg P. brassicae), rapeseed (eg P. parasitica), onions (eg P. destructor), tobacco (P. tabacina) and soybeans (eg P. manshurica) ; Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean; Phialophora spp., for example, on vines (eg P. tracheiphila and P. tetraspora) and soybeans (eg P. gregata: rot); Phoma lingam (root and stem rot) on rapeseed and cabbage and P. betae (root rot, leaf spot and falling) on sugar beet; Phomopsis spp. in sunflowers, vines (eg, P. viticola: leaf spot) and soybeans (eg, stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (deterioration, rotting of roots, leaves, fruits and stem) in various vegetables such as paprika and cucurbits (eg P. capsici), soybeans (eg P. megasperma, syn. P. soybeane), potatoes and tomatoes (eg P. infestans: late blight) and broad-leaved trees (eg P. ramorum: sudden death of the oak); Plasmodiophora brassicae (trunk root) in cabbage, rape, radish and other vegetables; Plasmopara spp., eg P. viticola (vine mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) in pink vegetables, hops, pome and soft fruits, for example, P. leucotricha on apples, Polymyxa spp., for example, in cereals such as barley and wheat (P. graminis) and sugar beets (P. betae) and, therefore, communicable viral diseases; Pseudocercosporella herpotrichoides (ocele, teleomorph: Tapesia yallundae) on cereals, eg wheat or barley; Pseudoperonospora (mildew) on various vegetables, for example, P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or brenner rot, anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various vegetables, eg P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (black or stem rust) or P. recondita (brown or leaf rust) on cereals such as wheat, barley or rye, P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (brown spot) on wheat or P. teres (reticular spot) on barley; Piricularia spp., for example, P. oryzae (teleomorph: Magnaporthe grisea, blast) on rice and P. grisea on turfgrass and cereals; Pythium spp. (bump) in lawn, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, legumes and other vegetables (eg, P. ultimum or P. aphanidermatum); Ramularia spp., for example, R. collocygni (Ramularia leaf spots, physiological leaf spots) on barley and R. beticola on sugar beet; Rhizoctonia spp. in cotton, rice, potato, grass, corn, rapeseed, potato, sugar beet, vegetables and various other vegetables, for example, R. solani (root and stem rot) in soybean, R. solani (sheath pest) in rice or R. cerealis (spring pest Rhizoctonia) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, kale, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (white rot or mold) in vegetables and crops such as rapeseed, sunflowers (for example S. sclerotiorum) and soybeans (for example S. rolfsii or S. sclerotiorum); Septoria spp. in several vegetables, for example, S. glycines (brown spot) on soybean, S. tritici (Septoria spot) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora spot) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf pest) on maize (eg, S. turcicum, syn Helminthosporium turcicum.) and turfgrass; Sphacelotheca spp. (soot) on corn, (eg, S. reiliana: crown soot), sorghum and sugar cane; Sphaerotheca fuliginea (powdery mildew) in cucurbits; Spongospora subterranea (scabies powder) on potatoes and communicable viral diseases; Stagonospora spp. in cereals, for example, S. nodorum (stain Stagonospora, teleomorph: Leptosphaeria [syn Phaeosphaeria.] nodorum) in wheat; Synchytrium endobioticum in potatoes (potato wart disease); Taphrina spp., for example, T. deformans (leaf wrinkle disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) in tobacco, pome fruit, vegetables, soybeans and cotton, eg T. basicola (syn. chalara elegans); Tilletia spp. (common bulge or smelly soot) on cereals, such as, for example, T. tritici (syn. T. caries, wheat bulge) and T. controversa (dwarf bulge) on wheat; Typhula incarnata (snow gray mold) on barley or wheat; Urocystis. spp., for example, U. occulta (stem soot) on rye; Uromyces spp. (rust) on vegetables such as beans (eg U. appendiculatus, syn U. phaseoli.) on sugar beet (eg U. betae); Ustilago spp. (loose soot) on cereals (eg, U. nuda and U. avaenae), on corn (eg, U. maydis: corn soot) and sugarcane; Venturia spp. (scabies) on apples (eg V. inaequalis) on pears, and Verticillium spp. (wilt) in various vegetables such as ornamental fruits and vegetables, vines, soft fruits, vegetables and crops, for example V. dahliae in strawberries, rapeseed, potatoes and tomatoes.
[0196] In particular, the compositions of the present invention are effective against plant pathogens in special crops such as vines, fruits, hops, vegetables and tobacco - see list above.
[0197] The compositions of the present invention are also suitable for the control of harmful fungi in the protection of stored products or crops and in the protection of materials. The term "materials protection" should be understood to indicate the protection of technical and non-living materials, such as adhesives, glues, wood, paper and cardboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or tissues, against infestation and destruction by harmful microorganisms such as fungi and bacteria. Regarding the protection of wood and other materials, special attention is given to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans., Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp. ., Trichurus spp., Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophillum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., and in addition, in protecting stored products and cultures, the following yeast fungi are of note: Candida spp. and Saccharomyces cerevisiae.
[0198] The method of treatment, according to the present invention, can also be used in the field of protection of crop products or stored against attack by fungi and microorganisms. According to the present invention, the term "stored products" is intended to indicate natural substances of plant or animal origin and their processed forms, which have been removed from the natural life cycle and for which long-term protection is desired. Stored products of vegetable origin, such as vegetables or their parts, for example, stems, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried , moistened, comminuted, ground, pressed or roasted, this process is also known as post-harvest treatment. It also falls under the definition of wood-stored products, in the form of raw wood, such as construction timber, electricity poles and barriers, or in the form of finished articles, such as furniture or objects produced from wood. Stored products of animal origin are skins, hides, hair, hair and the like. The combinations according to the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
[0199] Preferably, the term "stored products" is intended to indicate natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
[0200] Plant propagation materials can be treated with the compositions of the present invention prophylactically, before or during planting or transplanting.
[0201] The present invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I and at least one pesticide II, according to the present invention.
[0202] An agrochemical composition comprises a fungicidal effective amount of a compound I and a pesticide II. The term "effective amount" means an amount of the composition or compounds I, which is sufficient to control harmful fungi on cultivated plants or to protect the materials and which does not result in significant damage to the treated plants. This amount can vary over a wide range and depends on a number of factors, such as the species of fungus to be controlled, the treated plant or material cultivated, climatic conditions, and the specific compound used.
[0203] Compounds I and pesticides II, their N-oxides and salts can be converted into usual types of agrochemical compositions, for example, solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, capsules, and its mixtures. Examples of composition types are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg CS, ZC), pastes, tablets, dusts or wettable powders (eg WP, SP, WS, DP, DS), pressed (eg BR, TB, DT), granules (eg WG, SG, GR, FG , GG, MG), insecticidal articles (eg LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (GF). These and other types of compositions are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph n° 2, 6th ed. May 2008, CropLife International.
[0204] The compositions are prepared in a known manner, as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
[0205] Suitable auxiliaries are solvents, liquid vehicles, solid vehicles or excipients, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, stimulants food, compatibilizers, bactericides, antifreeze agents, antifoam agents, dyes, adhesives and binders.
[0206] Suitable solvents and liquid vehicles are water and organic solvents such as medium to high boiling mineral oil fractions, eg kerosene or diesel oil; oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example, N-methylpyrrolidone, fatty acid dimethylamides, and mixtures thereof.
[0207] Suitable solid carriers or excipients are earth minerals such as silicates, silica gels, talc, kaolin, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate and magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, for example, cereal flour, tree bark flour, wood flour, nutshell flour, and mixtures thereof.
[0208] Suitable surfactants are surfactant compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and their mixtures. These surfactants can be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).
[0209] Suitable anionic surfactants are the alkaline, alkaline earth or the ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkyl phenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalene sulfonates, decyl sulfonates, docyl sulfonates naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are fatty acid sulfates and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates of carboxylated alcohol or ethoxylates of alkylphenol.
[0210] Suitable nonionic surfactants are alkoxylated, N-substituted fatty acid amides, amine oxides, esters or sugar-based surfactants, polymeric surfactants and their mixtures. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated to from 1 to 50 equivalents. Ethylene oxide and/or propylene oxide can be used for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid starches are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar based surfactants are sorbitans, ethoxylated sorbitans, sucrose esters and glucose or alkylpolyglucosides. Examples of polymeric surfactants are vinyl pyrrolidone homo- or copolymers, vinyl alcohols or vinyl acetate.
[0211] Examples of suitable cationic surfactants are quaternary surfactants, eg quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are the alkaline salts of polyacrylic acid. Examples of polybases are polyvinylamines or polyethyleneamines.
[0212] Suitable adjuvants are compounds, which have negligible pesticidal activity or even no pesticidal activity, and that enhance the biological performance of compound I with the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Other examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
[0213] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates, and silicates.
[0214] Suitable bactericides are those derived from bronopol and isothiazolinone, such as the alkylisothiazolinones and benzisothiazolinones.
[0215] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.
[0216] Suitable defoamers are silicones, long-chain alcohols and fatty acid salts.
[0217] Suitable colorants are pigments (eg red, blue or green) with low water solubility content and water-soluble dyes. Examples are inorganic colorants (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (eg alizarin-, azo- and phthalocyanine colorants).
[0218] Examples of suitable adhesives or binders are vinyl polypyrrolidone, polyvinyl acetate, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
[0219] Examples of types of composition and their preparation are: (I) HYDROSOLUBLES CONCENTRATES (SL, LS) - From 10 to 60% by weight of active substances and from 5 to 15% by weight of wetting agent (for example , alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (eg alcohols) to 100% by weight. The active substance dissolves after dilution in water. (II) DISPERSIBLE CONCENTRATES (DC) - From 5 to 25% by weight of active substances and from 1 to 10% by weight of dispersant (eg polypyrrolidone vinyl) are dissolved in up to 100% by weight of organic solvent ( for example, cyclohexanone). Dilution in water provides a dispersion. (III) EMULSIABLE CONCENTRATES (EC) - From 15 to 70% by weight of active substances and from 5 to 10% by weight of emulsifiers (eg calcium dodecylbenzene sulfonate and castor oil ethoxylate) are dissolved in non-organic solvent water soluble (eg aromatic hydrocarbons) at 100% by weight. Dilution in water provides an emulsion. (IV) EMULSIONS (EW, EQ, ES) - From 5 to 40% by weight of active substances and from 1 to 10% by weight of emulsifiers (eg calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 to 40% by weight of non-water-soluble organic solvent (eg aromatic hydrocarbons). This mixture is introduced in up to 100% by weight of water by means of an emulsifying machine and into a homogeneous emulsion. Dilution in water provides an emulsion. (V) SUSPENSIONS (SC, OD, FS) - In an agitated ball mill, 20 to 60% by weight of active substances are ground with the addition of 2 to 10% by weight of dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), from 0.1 to 2% by weight of thickener (eg xanthan gum) and up to 100% by weight of water to provide a fine suspension of active substance. Dilution in water provides a stable suspension of the active substance. For the FS-type composition, up to 40% by weight of the binder (eg polyvinyl alcohol) are added. (VI) WATER DISPERSIBLE GRANULES AND WATER-SOLUBLE GRANULES (WG, SG) - From 50 to 80% by weight of active substances are finely ground with the addition of up to 100% by weight of dispersants and wetting agents (eg lignosulfonate). sodium and ethoxylated alcohols) and prepared in the form of water-dispersible or water-soluble granules by means of technical apparatus (eg extrusion, spray tower, fluidized bed). Dilution in water provides a stable dispersion or solution of the active substance. (VII) WATER-DISPERSIBLE POWDER AND WATER-SOLUBLE POWDERS (WP, SP, WS) - From 50 to 80% by weight of active substances are milled in a stator rotor mill with the addition of 1 to 5% by weight of dispersants (per example sodium lignosulfonate), from 1 to 3% by weight of wetting agents (for example alcohol ethoxylate) and up to 100% by weight of solid carrier, for example silica gel. Dilution in water provides a stable dispersion or solution of the active substance. (VIII) GEL (GW, GF) - In an agitated ball mill, 5 to 25% by weight of active substances are ground with the addition of 3 to 10% by weight of dispersants (eg sodium lignosulfonate) , from 1 to 5% by weight of thickener (eg carboxymethylcellulose) and water up to 100% by weight to provide a fine suspension of the active substance. Dilution with water provides a stable suspension of the active substance. (IX) MICROEMULSION (ME) - From 5 to 20% by weight of active substances are added to from 5 to 30% by weight of the organic solvent mixture (for example, the fatty acid dimethylamide and cyclohexanone), from 10 to 25 % by weight of the surfactant mixture (eg ethoxylated alcohol and ethoxylated arylphenol), and water up to 100%. This mixture is stirred for 1 hour to spontaneously produce a thermodynamically stable microemulsion. (X) MICROCAPSULAS (CS) - An oil phase comprising from 5 to 50% by weight of active substances, from 0 to 40% by weight of non-water-soluble organic solvent (for example, aromatic hydrocarbons), from 2 to 15 % by weight of acrylic monomers (eg methylmethacrylate, methacrylic acid and a dior triacrylate) are dispersed in an aqueous solution of a protective colloid (eg polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising from 5 to 50% by weight of a compound I, according to the present invention, from 0 to 40% by weight of non-water-soluble organic solvent (for example aromatic hydrocarbons), and an isocyanate monomer (eg, diphenylmeten-4,4'-diisocyanatae) are dispersed in an aqueous solution of a protective colloid (eg, polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is 1 to 10% by weight. The percentage (%) by weight refers to the total CS composition. (XI) DUSTABLE POWDERS (DP, DS) - From 1 to 10% by weight of active substances are finely ground and intimately mixed with the solid carrier (eg finely divided kaolin) at 100% by weight. (xii) GRANULES (GR, FG) - From 0.5 to 30% by weight of active substances are finely ground and associated with the solid carrier (eg silicate) at 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed. (XIII) ULTRA LOW VOLUME LIQUIDS (UL) - From 1 to 50% by weight of active substances are dissolved in organic solvent (eg aromatic hydrocarbons) at 100% by weight.
[0220] The types of compositions (i) to (xiii) optionally may comprise other auxiliaries, such as from 0.1 to 1% by weight of bactericides, from 5 to 15% by weight of antifreeze agents, from 0, 1 to 1% by weight of defoamers, and from 0.1 to 1% by weight of colorants.
[0221] Agrochemical compositions, in general, comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75% by weight of the active substances. The active substances are used in a purity of 90% to 100%, preferably from 95% to 100% (according to the NMR spectrum).
[0222] Seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dust treatment (DS), water-dispersible powders for sludge treatment (WS), water-soluble powders (SS), emulsions (ES) emulsifiable concentrates (EC) and gels (GF) are generally used for the purposes of treating plant propagation materials, especially seeds.
[0223] The compositions in question, after being diluted by a factor of two to ten, provide concentrations of active substance from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in ready-to-use preparations. The application can be carried out before or during sowing. Methods for applying compound I, compound II and their compositions, respectively, to plant propagation materials, especially seeds, include methods of covering, coating, pelletizing, dusting, dipping and furrowing the seed material. propagation. Preferably, compound I and pesticide II or their compositions, respectively, are applied to the plant propagation material by a method in such a way that germination is not induced, for example, through the segment by covering, pelletizing, coating and sprinkling the seeds.
[0224] When used in plant protection, the amounts of active substances used, depending on the type of effect desired, are from 0.001 to 2 kg per hectare, preferably from 0.005 2 kg per hectare, most preferably , from 0.05 to 0.9 kg per hectare, and in particular from 0.1 to 0.75 kg per ha.
[0225] In the treatment of plant propagation material, such as seeds, for example, by sprinkling, coating or soaking the seeds, the amounts of the active substance from 0.1 to 10 kg, in particular from 0.1 to 1000 g, more preferably from 1 to 1000 g, even more preferably from 1 to 100 g and even more preferably from 5 to 100 g, per 100 kg of material of propagation of vegetables (preferably the seeds) in general are necessary.
[0226] When used in the protection of stored materials or products, the amount of active substance applied depends on the type of application area and the desired effect. The amounts normally applied in the protection of materials, for example, are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of active substance per cubic meter of treated material.
[0227] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients and other pesticides (for example, herbicides, insecticides, fungicides, growth regulators, protective agents, biopesticides) can be added to active substances, or to compositions which comprise them as a premix or, if appropriate, not until just before use (tank mix). These agents can be mixed with the compositions according to the present invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.
[0228] The user applies the composition, according to the present invention, usually from a pre-dosing device, a backpack sprayer, a spray tank or an irrigation system. Usually, the agrochemical composition is carried out with water, buffer and/or other auxiliaries to the desired application concentration and the ready-to-use spray solution or the agrochemical composition according to the present invention is therefore obtained. Typically 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray solution is applied per hectare of useful agricultural area.
[0229] In compositions, the proportions of the compound, advantageously, are selected to produce a synergistic effect.
[0230] The term “synergistic effect, in particular, should refer to the Formula defined by Colby (Colby, S.R., “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds, 15, pages 20-22, 1967).
[0231] The term “synergistic effect” should also refer to that defined by applying the Tammes method, (Tammes, PML, “Isoboles, a graphic representation of synergism in pesticides”, Netherlands. J. Plant Pathol. 70, 1964) .
[0232] The active compounds, alone or combined, are prepared as a stock solution comprising 25 mg of active compound consisting of up to 10 mL using a composition of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent that it has an emulsifying and dispersing action based on ethoxylated alkylphenols) in a solvent/emulsifier volume ratio of 99:1. The mixture is then made up to 100 ml with water. This stock solution is diluted with the described composition of emulsifier / solvent / water to provide the concentration of active compound indicated below.
[0233] The visually determined percentages of infected leaf area are converted to percentage efficiencies (%) of the untreated control.
[0234] Efficacy (E) using Abbot's Formula is calculated as follows: - E = (1 - α / β) 100 - α corresponds to the fungal infection of treated plants in percentage (%); and - β corresponds to the fungal infection of untreated (control) vegetables in percentage (%).
[0235] An effectiveness of 0 means that the infection level of the treated vegetables matches that of the untreated control vegetables, an effectiveness of 100 means that the treated vegetables were not infected.
[0236] The expected efficiencies of the combinations of active compounds were determined using Colby's Formula [R.S. Colby, ''Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, 20-22 (1967) and compared with observed efficacies; Colby's formula: E = x + y - x • y/100 - E means the expected efficacy, expressed as a percentage (%) of the untreated control, when using the mixture of active compounds (A) and (B) in the concentrations a and b; - x means the efficacy, expressed as a percentage (%) of the untreated control, when using an active compound (A) at concentration a; and - y means the efficacy, expressed as a percentage (%) of the untreated control, when using an active compound (B) at concentration b.
[0237] The fungicidal action of the compositions, according to the present invention, can be demonstrated by the tests described below. MICROTEST
[0238] The active compounds were formulated separately as a stock solution that has a concentration of 10,000 ppm in dimethyl sulfoxide. The sulfoxaflor product was used as a finished commercial formulation and diluted with water to the indicated concentration of active compound. M1: ACTIVITY AGAINST THE PATHOGENIC BLENDING AGENT PHYTOPHTHORA INFESTANS IN THE MICRO TITRATION TEST (PHYTIN)
[0239] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A spore suspension of Phytophtora infestans containing an aqueous nutrient medium based on pea juice or DDC medium was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTPs were measured at 405 nm 7 days after inoculation. M2: ACTIVITY AGAINST THE GRAY MOLD BOTRYTIS CINEREA IN THE MICRO TITRATION TEST (BOTRCI)
[0240] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Botrci cinerea spores in an aqueous biomalt or yeast-bactopeptone-sodium acetate solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTPs were measured at 405 nm 7 days after inoculation. M3: ACTIVITY AGAINST PYRICULARIA ORYZAE RICE BRUSONE IN THE MICRO TITRATION TEST (PYRIOR)
[0241] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. Stock solutions were mixed according to ratio, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Pyricularia oryzae spores in an aqueous biomalt or yeast-bactopeptone-glycerin solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTPs were measured at 405 nm 7 days after inoculation. M4: ACTIVITY AGAINST WHEAT LEAF STAINING CAUSED BY SEPTORIA TRITICI (SEPTTR)
[0242] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Septoria tritici spores in an aqueous biomalt or yeast-bactopeptone-glycerin solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after inoculation. M5: ACTIVITY AGAINST THE FILM CAUSED BY ALTERNARIA SOLANI (ALTESO)
[0243] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Alternaria solani spores in an aqueous biomalt or yeast-bactopeptone-glycerin solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after inoculation. M6: ACTIVITY AGAINST WHEAT LEAF STAINING CAUSED BY LEPTOSPHAERIA NODORUM (LEPTNO)
[0244] Stock solutions were mixed according to proportion, pipetted into a microtiter plate (MTP) and diluted with water to the indicated concentrations. A suspension of Leptosphaeria nodorum spores in an aqueous biomalt or yeast-bactopeptone-glycerin solution was then added. The plates were placed in a chamber saturated with water vapor at a temperature of 18°C. Using an absorption photometer, MTPs were measured at 405 nm 7 days after inoculation.
[0245] The measured parameters were compared with the growth of the free active compound control variant (100%) and the white value of free compound and active free of fungus to determine the relative growth in percentage (%) of pathogens in the respective active compounds.
[0246] These percentages have been converted to efficiencies.
[0247] An effectiveness of 0 means that the infection level of the treated vegetables matches that of the untreated control vegetables, an effectiveness of 100 means that the treated vegetables were not infected.
[0248] The expected efficiencies of active compound combinations were determined using Colby's Formula [RS Colby, ''Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, 20-22 (1967)] and compared with the observed efficacies . RESULTS

权利要求:
Claims (7)
[0001]
1. COMPOSITIONS, characterized in that they comprise: (1) as component I, a compound I-3: 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazole -1-yl)propan-2-ol; and (2) as component II, a triflumezopyrim (mesoionic) compound (II-7).
[0002]
COMPOSITIONS according to claim 1, characterized in that compound I and component II are present in a synergistically effective amount.
[0003]
3. COMPOSITIONS, according to any one of claims 1 to 2, characterized in that component I and component II are present in a total weight ratio of 100:1 to 1:100.
[0004]
4. COMPOSITIONS, according to any one of claims 1 to 3, characterized in that they further comprise an agrochemical auxiliary.
[0005]
5. USE OF A COMPOSITION, as defined in any one of claims 1 to 4, characterized in that it is for combating phytopathogenic fungi.
[0006]
6. METHOD FOR FIGHTING phytopathogenic FUNGI, characterized in that it comprises the treatment of fungi or materials, plants, soil or seeds to protect against fungal attack with an effective amount of a composition, as defined in any of the claims from 1 to 4.
[0007]
7. MATERIAL FOR PROPAGATION OF VEGETABLES, characterized in that it is coated with components I and II of the compositions, as defined in any one of claims 1 to 4, in an amount from 0.1 to 10 kg of active substances per 100 kg of seed.

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同族专利:

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公开号 | 公开日

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AU2015281187B2|2018-10-04|

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CN106793776A|2017-05-31|

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EP3269245A1|2018-01-17|

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EA201892678A1|2019-04-30|

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CA2951177A1|2015-12-30|

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EA032078B1|2019-04-30|

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EP3272217A1|2018-01-24|

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法律状态:
2019-08-27| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|

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2021-06-08| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2021-07-06| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 15/06/2015, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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EP14173980|2014-06-25|

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EP14173980.5|2014-06-25|

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PCT/EP2015/063269|WO2015197393A1|2014-06-25|2015-06-15|Pesticidal compositions|

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