EP3432717A1 - Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes - Google Patents
Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantesInfo
- Publication number
- EP3432717A1 EP3432717A1 EP17710583.0A EP17710583A EP3432717A1 EP 3432717 A1 EP3432717 A1 EP 3432717A1 EP 17710583 A EP17710583 A EP 17710583A EP 3432717 A1 EP3432717 A1 EP 3432717A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- fluoro
- cyclopropyl
- methyl
- difluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 241001360088 Zymoseptoria tritici Species 0.000 title claims abstract description 34
- 241001533598 Septoria Species 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 239000005825 Prothioconazole Substances 0.000 claims abstract description 94
- 239000005760 Difenoconazole Substances 0.000 claims abstract description 61
- 239000005839 Tebuconazole Substances 0.000 claims abstract description 59
- 239000000417 fungicide Substances 0.000 claims abstract description 46
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 43
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 claims abstract description 38
- 230000035772 mutation Effects 0.000 claims abstract description 35
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 34
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims abstract description 33
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims abstract description 31
- 235000013339 cereals Nutrition 0.000 claims abstract description 31
- 239000002689 soil Substances 0.000 claims abstract description 15
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract 14
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 12
- ACDCNNFPJPHJCQ-UHFFFAOYSA-N n-[(2-tert-butyl-5-methylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CC1=CC=C(C(C)(C)C)C(CN(C2CC2)C(=O)C=2C(=NN(C)C=2F)C(F)F)=C1 ACDCNNFPJPHJCQ-UHFFFAOYSA-N 0.000 claims description 12
- UTXLNSPIBIMGQJ-UHFFFAOYSA-N n-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=CC=2Cl)C(F)(F)F)C2CC2)=C1F UTXLNSPIBIMGQJ-UHFFFAOYSA-N 0.000 claims description 12
- POIXHZKAAMCWOT-UHFFFAOYSA-N n-[[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(Cl)C=2F)C(F)(F)F)C2CC2)=C1F POIXHZKAAMCWOT-UHFFFAOYSA-N 0.000 claims description 12
- HEMPTJWLSOMNER-UHFFFAOYSA-N n-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(Cl)C=2)C(F)(F)F)C2CC2)=C1F HEMPTJWLSOMNER-UHFFFAOYSA-N 0.000 claims description 12
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- MRCJJCNYJGXHAU-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-n-[(5-methyl-2-propan-2-ylphenyl)methyl]pyrazole-4-carboxamide Chemical compound CC(C)C1=CC=C(C)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 MRCJJCNYJGXHAU-UHFFFAOYSA-N 0.000 claims description 12
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- FLQNESNIAKFCNJ-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-n-[(2-ethyl-4,5-dimethylphenyl)methyl]-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CCC1=CC(C)=C(C)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 FLQNESNIAKFCNJ-UHFFFAOYSA-N 0.000 claims description 12
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 claims description 11
- DGOAXBPOVUPPEB-UHFFFAOYSA-N 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]pyrazole-4-carboxamide Chemical compound C=1N(C)N=C(C(F)F)C=1C(=O)N(OC)C(C)CC1=C(Cl)C=C(Cl)C=C1Cl DGOAXBPOVUPPEB-UHFFFAOYSA-N 0.000 claims description 11
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 claims description 11
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
- 239000004555 ultra-low volume (ULV) suspension Substances 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004564 water dispersible powder for slurry treatment Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Definitions
- the present invention relates to a method for controlling septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and/or 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III.
- the present invention also relates to the use of a composition
- a composition comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III for controlling septoria leaf blotch on cereal plants caused by the pathogen Zymoseptoria tritici containing the V136A and/or I381V mutation by treating cereal plants, their seed or the soil with the composition.
- Zymoseptoria tritici is a species of filamentous fungus, an ascomycete in the family Mycosphaerellaceae. It is a plant pathogen causing septoria leaf blotch, which is currently the most dominant cereal disease in Western Europe and is among the top two or three most economically damaging diseases of cereals in the United States. Control of septoria leaf blotch is becoming more and more difficult for farmers. Reason is the capability of the fungi to develop resistance to widely used powerful fungicidal agents.
- Fungicides containing azole mixtures have been widely and successfully used in recent years for Zymoseptoria tritici control. Due to particular mutations detected in the cytochrome b gene of some plant pathogenes, including Zymoseptoria tritici, a sensitivity shift against particular fungicides, including azole fungicides, has been observed during the last years but not all azole fungicides are affected to the same extent.
- a change from valine to alanin at position 136 in the cyp51 gene - the V136A mutation - or a change from isoleucine to valine at position 381 in the cyp51 gene - the 138 IV mutation - govern a sensitivity shift or resistance to some azoles but not all azoles are affected to the same extent. Additionally, cross-resistances of azoles have been observed. Such cross resistances even more increase the difficulties in controlling septoria leaf blotch caused by such resistant strains.
- Azoles are fungicides well known as sterol biosynthesis inhibitors, see FRAC classification (FRAC website http://www/frac.info/), in particular subgroup Gl. It is in particular known that azole fungicides are inhibitors of fungal sterol C14 demethylase cyp51 (demethylation inhibitor (DMI) fungicides), which is a cytochrome P450 monooxygenase. Therefore, occurrence of a cross resistance of two azole fungicides having the same mode of action is not a surprise.
- DMI demethylase cyp51
- the present invention comprises a method for controlling septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and/or 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising (a) prothioconazole as compound I; and
- the present invention comprises a method for controlling septoria leaf blotch on cereal plants caused by Zymoseptoria tritici containing the V136A and 138 IV mutation, comprising treating cereal plants, their seed or the soil with a composition comprising
- compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III excellently control septoria leaf blotch caused by those Zymoseptoria tritici mutants.
- compositions comprising (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III to control Zymoseptoria tritici containing the V136A and/or 138 IV mutation is important for appropriate resistance management, since Zymoseptoria tritici showing a sensitivity shift to azole applications can be successfully controlled without increasing the dosage rates. It has been found that presence of the V136A mutation increases the sensitivity of Septoria leaf blotch populations against difenoconazole or tebuconazole whereas prothioconazole shows stronger intrinsic activity on strains carrying the 138 IV mutation but not the V136A mutation.
- prothioconazole creates a selection pressure enriching the V136A mutation in the Zymoseptoria tritici population and on the other hand application of difenoconazole or tebuconazole creates a selection pressure enriching the 138 IV mutation in the Zymoseptoria tritici population.
- compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III can perfectly be used for controlling Zymoseptoria tritici containing the V136A and/or the 138 IV mutation, preferably for controlling Zymoseptoria tritici containing both, the V136A and the 138 IV mutation.
- Containing both, the V136A and the 138 IV mutation means that both mutations are present in the pathogen population, preferably that both mutations are present in the same genome, preferably that both mutations are present in the cyp51 gene.
- SDHI fungicides show excellent control of septoria leaf blotch on cereal plants caused by Zymoseptoria tritici
- the sensitivity against fungicides having this mode of action is also affected by resistant mutants.
- the presence of a SDHI (Succinate dehydrogenase inhibitor) fungicide in combinations with azole fungicides reduces the selection pressure and the efficacy of the additional SDHI fungicide is not affected by any of the V136A and 138 IV mutations at all.
- compositions according to the present invention comprising the particular combinations of (a) prothioconazole as compound I and (b) difenoconazole or tebuconazole as compound II and (c) at least one SDHI fungicide as compound III can perfectly be used for controlling Zymoseptoria tritici containing the V136A and/or the 138 IV mutation.
- the present invention also comprises the use of a composition comprising
- the present invention also comprises the use of a composition comprising
- the use according to the invention is an important use for resistance management by controlling Zymoseptoria tritici being less susceptible to azoles.
- the composition comprises prothioconazole as compound I and tebuconazole as compound II and at least one SDHI fungicide as compound III.
- the composition comprises prothioconazole as compound I and difenoconazole as compound II and at least one SDHI fungicide as compound III.
- SDHI fungicides are succinate dehydrogenase inhibitors, classified in group C (in particular C2: Inhibition of complex II: Succinate dehydrogenase) of the FRAC classification (FRAC website http://www/frac.info/).
- Preferred SDHI fungicides are selected from the group consisting of bixafen (compound III- 1), fluopyram (compound III-2), fluxapyroxad (compound III-3), isopyrazam (compound III-4), bezovindiflupyr (compound III-5), pydiflumetofen (compound III-6), penthiopyrad (compound III-7) and boscalid (compound III-8) or selected from the group consisting of
- composition comprises one of the combinations according to Table 1.
- compositions comprising
- compositions comprising
- N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-l -methyl- lH-pyrazole-4- carboxamide (compound III- 14); N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2- isopropylbenzyl)- 1 -methyl- lH-pyrazole-4-carboxamide (compound III- 15); N-cyclopropyl-N-(2- cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro- l -methyl- lH-pyrazole-4-carboxamide (compound III- 16); N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-l- methyl-lH-pyrazole-4
- the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
- the weight ratio of the compound I to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
- the weight ratio of the compound II to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
- the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3; and the weight ratio of the compound I to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3; and the weight ratio of the compound II to compound III in the composition is from 10: 1 to 1 : 10, preferably from 5: 1 to 1 :5, more preferably from 4: 1 to 1 :4, most preferably from 3: 1 to 1 :3.
- the weight ratio of the compound I to compound II in the composition is from 10: 1 to 1 : 10 and the weight ratio of the compound I to compound III in the composition is from 10: 1 to 1 : 10 and the weight ratio of the compound II to compound III in the composition is from 10: 1 to 1 : 10.
- the weight ratio of the compound I to compound II in the composition is from 5: 1 to 1 :5 and the weight ratio of the compound I to compound III in the composition is from 5: 1 to 1 :5 and the weight ratio of the compound II to compound III in the composition is from 5: 1 to 1 :5.
- the weight ratio of the compound I to compound II in the composition is from 4: 1 to 1 :4 and the weight ratio of the compound I to compound III in the composition is from 4: 1 to 1 :4 and the weight ratio of the compound II to compound III in the composition is from 4: 1 to 1 :4.
- the weight ratio of the compound I to compound II in the composition is from 3: 1 to 1 :3 and the weight ratio of the compound I to compound III in the composition is from 3: 1 to 1 :3 and the weight ratio of the compound II to compound III in the composition is from 3 : 1 to 1 :3.
- compositions according to the present invention can also be combined with known bactericides, acaricides, nematicides or insecticides, in order thus to broaden, for example, the activity spectrum or to further prevent development of resistance.
- the cereal plants, their seed or the soil in which the plant is growing or in which it is desired to grow can be treated.
- Treatment of plants according to the inventions also includes treatment of plant parts.
- the compositions used according to the invention can be used to curatively or preventively control the disease.
- the cereal plants or plant parts are treated with the compositions according to the present invention.
- Cereals according to the present invention include wheat and triticale. Where a compound I or a compound II or a compound III can be present in tautomeric form, such a compound is understood hereinabove and hereinbelow also to include, where applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case.
- Compounds I or compounds II or compounds III having at least one basic centre are capable of forming, for example, acid addition salts, e.g. with strong inorganic acids, such as mineral acids, e.g.
- perchloric acid sulfuric acid, nitric acid, nitrous acid, a phosphoric acid, a hydrohalic acid, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, or acidic salts, such as NaHSC ⁇ and KHSO4, with strong organic acids, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, maleic acid, fumaric acid, tartaric acid, sorbic acid oxalic acid, alkylsulphonic acids (sulphonic acids having straight- chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such as phenyl and naphthy
- Compounds I or compounds II or compounds III having at least one acid group are capable of forming, for example, salts with bases, e.g. metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine.
- bases e.g. metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a
- corresponding internal salts may optionally be formed.
- any reference to the free compounds I or free compounds II or free compounds III or to their salts should be understood as including also the corresponding salts or the free compounds I or free compounds II or free compounds III, respectively, where appropriate and expedient. The same also applies to tautomers of compounds I or compounds II or compounds III and to their salts.
- composition used according to the invention may also comprise an agriculturally acceptable support, carrier or filler.
- the term "support” denotes a natural or synthetic, organic or inorganic compound with which the active compound I and II and optionally III is combined or associated to make it easier to apply, notably to the parts of the plant.
- This support is thus generally inert and should be agriculturally acceptable.
- the support may be a solid or a liquid.
- suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports may also be used.
- the composition may also comprise additional components. In particular, the composition may further comprise a surfactant.
- the surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants.
- surfactant content may be comprised from 5% to 40% by weight of the composition.
- Colouring agents such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyanblue, and organic pigments such as alizarin, azo and metallophthalocyanine dyes, and trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts can be used.
- composition according to the invention may contain from 0.05 to 99% by weight of active compounds, preferably from 10 to 70%o by weight.
- the combination or composition according to the invention can be used as such, in form of their formulations or as the use forms prepared therefrom, such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.
- aerosol dispenser
- the treatment of plants and plant parts with the composition according to the invention is carried out directly or by action on their environment, habitat or storage area by means of the normal treatment methods, for example by watering (drenching), drip irrigation, spraying, atomizing, broadcasting, dusting, foaming, spreading-on, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
- compositions used according to the invention include not only compositions which are ready to be applied to the plant, seed or soil to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions which must be diluted before application to the plant, seed or soil.
- a suitable device such as a spraying or dusting device
- the application rates can be varied within a relatively wide range, depending on the kind of application.
- the application rate of the active ingredients used according to the invention is generally and advantageously
- leaves • in the case of treatment of plants or plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 10 to 800 g/ha, even more preferably from 25 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used);
- the application rate of the active ingredients used according to the invention is preferably
- compositions of the invention are particularly suitable for the treatment of seeds.
- the invention comprises a procedure in which the seed is treated at the same time with a compound I and a compound II and optionally a compound III. It further comprises a method in which the seed is treated with compound I and compound II and optionally compound III sequentially or separately, i.e. at different times. If the single active ingredients are applied in a sequential / separate manner, i.e. at different times, they are applied one after the other within a reasonably short period, such as a few hours or days. Preferably the order of applying the compounds I and II and optionally III is not essential for working the present invention.
- One of the advantages of the present invention is that the particular systemic properties of the active ingredients and compositions mean that treatment of the seed with these active ingredients and compositions not only protects the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
- the active ingredients or compositions can especially also be used with transgenic seed, in which case the plant growing from this seed is capable of expressing a protein which acts against pests.
- the active ingredients or compositions By virtue of the treatment of such seed with the active ingredients or compositions, merely the expression of the protein, for example an insecticidal protein, can control certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally increases the effectiveness for protection against attack by pests.
- transgenic seed As also described below, the treatment of transgenic seed with the active ingredients or compositions is of particular significance. This relates to the seed of plants containing at least one heterologous gene.
- the composition is applied to the seed alone or in a suitable formulation.
- the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
- the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15 % by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.
- compositions can be applied directly, i.e. without containing any other components and without having been diluted.
- suitable formulations and methods for seed treatment are known to those skilled in the art and are described, for example, in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 Al, WO 2002/080675, WO 2002/028186.
- the active ingredients usable in accordance with the invention can be converted to the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
- customary seed dressing formulations such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations.
- customary additives for example customary extenders and also solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water.
- Useful dyes which may be present in the seed dressing formulations usable in accordance with the invention are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.
- Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Preference is given to using alkyl naphthalenesulphonates, such as diisopropyl or diisobutyl naphthalenesulphonates.
- Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulphated derivatives thereof. Suitable anionic dispersants are especially lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates.
- Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference.
- Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.
- Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions.
- Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
- Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products.
- Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
- the gibberellins are known (cf. R. Wegler "Chemie der convinced für Schweizer- und Schadlingsbekampfungsstoff" [Chemistry of the Crop Protection Compositions and Pesticides], vol. 2, Springer Verlag, 1970, p. 401-412).
- the seed dressing formulations usable in accordance with the invention can be used, either directly or after previously having been diluted with water, for the treatment of a wide range of different seed, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.
- the procedure in the seed dressing is to place the seed into a mixer, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying process.
- the compound ratio I/II, I/III or I/II/III may be advantageously chosen so as to produce a synergistic effect.
- a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
- the expected activity for a given combination of two or three active compounds can be calculated as follows (cf. Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22). The latter article mentions the formula for combinations of 2 active compounds:
- X denotes the efficacy when using active compound A at an application rate of m ppm (or g/ha),
- Y denotes the efficacy when using active compound B (or C) at an application rate of n ppm (or g/ha),
- Z denotes the efficacy when using active compound C at an application rate of r ppm (or g/ha),
- Ei denotes the efficacy when using active compounds A and B at application rates of m and n ppm (or g/ha), and
- E2 denotes the efficacy when using active compounds A and B and C at application rates of m and n and r ppm (or g/ha),
- the efficacy is determined in %. 0 % means an efficacy which corresponds to that of the control, whereas an efficacy of 100 % means that no infection is observed.
- the action of the combination is superadditive, i.e. a synergistic effect is present.
- the actually observed efficacy must exceed the value calculated using the above formula for the expected efficacy (Ei or E2).
- Zymoseptoria tritici field strains carrying cyp51 mutation V136A Spore inoculum was produced by growing fungal isolates on Czapek-Dox agar medium, supplemented with 20 % (v/v) vegetable juice and 0.3 % (w/v) calcium carbonate, for one week at 20 °C. Spores were harvested by gentle scraping the agar surface and re-suspending the obtained spore material in glucose-peptone medium. The spore suspension was adjusted to lxlO 6 spores/mL. All fungal isolates were tested with the following final test compound concentrations: 0; 0.0064; 0.032; 0.16; 0.8; 4; 20 and 100 ⁇ g active ingredient per mL.
- Microtiter plates were prepared as follows: Ten ⁇ . of compound dilution (prepared in 80 % methanol), containing the amount of compound required for each concentration, was added to the cavities. After complete evaporation of the solvent, compounds were dissolved by adding 140 ⁇ , glucose-peptone medium per cavity, followed by overnight incubation on a rotatory shaker at 150 rpm. After adding 60 ⁇ , spore suspension into each cavity, plates were incubated at 20 °C and 90 % relative humidity for seven days on a rotatory shaker at 150 rpm. Fungal growth was determined photometrically at 620 nm.
- EC50 values concentration at which the pathogen growth is reduced by 50 % were calculated from the resulting dose- response for each strain and active ingredient, according to the extinction values. To determine the level of cross-resistance between pairs of the tested fungicides, the correlation of their EC50 values was evaluated by calculation of Pearson's correlation coefficient for each pair. A lower correlation coefficient between the active ingredients indicates a lower level of cross-resistance between them.
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Abstract
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16162284 | 2016-03-24 | ||
| PCT/EP2017/056524 WO2017162569A1 (fr) | 2016-03-24 | 2017-03-20 | Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP3432717A1 true EP3432717A1 (fr) | 2019-01-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP17710583.0A Withdrawn EP3432717A1 (fr) | 2016-03-24 | 2017-03-20 | Procédé de lutte contre la septoriose due à des souches de zymoseptoria tritici résistantes |
Country Status (2)
| Country | Link |
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| EP (1) | EP3432717A1 (fr) |
| WO (1) | WO2017162569A1 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3539384A1 (fr) * | 2018-03-15 | 2019-09-18 | Basf Se | Mélanges à 3 composantes comprenant du fluxapyroxad |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4272417A (en) | 1979-05-22 | 1981-06-09 | Cargill, Incorporated | Stable protective seed coating |
| US4245432A (en) | 1979-07-25 | 1981-01-20 | Eastman Kodak Company | Seed coatings |
| US4808430A (en) | 1987-02-27 | 1989-02-28 | Yazaki Corporation | Method of applying gel coating to plant seeds |
| US5876739A (en) | 1996-06-13 | 1999-03-02 | Novartis Ag | Insecticidal seed coating |
| DE19716257A1 (de) | 1997-04-18 | 1998-10-22 | Bayer Ag | Fungizide Wirkstoffkombination |
| US6503904B2 (en) | 1998-11-16 | 2003-01-07 | Syngenta Crop Protection, Inc. | Pesticidal composition for seed treatment |
| US6660690B2 (en) | 2000-10-06 | 2003-12-09 | Monsanto Technology, L.L.C. | Seed treatment with combinations of insecticides |
| US20020134012A1 (en) | 2001-03-21 | 2002-09-26 | Monsanto Technology, L.L.C. | Method of controlling the release of agricultural active ingredients from treated plant seeds |
| PL213968B1 (pl) | 2002-03-07 | 2013-05-31 | Basf Ag | Mieszanina grzybobójcza na bazie triazoli, sposób zwalczania szkodliwych grzybów i srodek grzybobójczy |
| DE102005035300A1 (de) * | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| PY1332818A (es) * | 2012-07-26 | 2017-01-02 | Syngenta Crop Protection Ag | Composiciones fungicidas |
| BR112015014753B8 (pt) * | 2012-12-20 | 2020-03-03 | Basf Agro Bv | composições, uso de uma composição, método para o combate de fungos fitopatogênicos e uso dos componentes |
| CN104936450A (zh) * | 2012-12-20 | 2015-09-23 | 巴斯夫欧洲公司 | 包含三唑化合物的组合物 |
| CN105120665B (zh) * | 2013-02-19 | 2017-06-09 | 拜耳作物科学股份公司 | 丙硫菌唑用于诱导宿主防御反应的用途 |
| CN104621126A (zh) * | 2013-11-15 | 2015-05-20 | 南京华洲药业有限公司 | 一种含丙硫菌唑和苯醚甲环唑的杀菌组合物及其应用 |
| CN104642331A (zh) * | 2013-11-15 | 2015-05-27 | 南京华洲药业有限公司 | 一种含丙硫菌唑和戊唑醇的杀菌组合物及其应用 |
-
2017
- 2017-03-20 EP EP17710583.0A patent/EP3432717A1/fr not_active Withdrawn
- 2017-03-20 WO PCT/EP2017/056524 patent/WO2017162569A1/fr not_active Ceased
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| Publication number | Publication date |
|---|---|
| WO2017162569A1 (fr) | 2017-09-28 |
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