WO2008025732A1 - Verfahren zur bekämpfung von schadpilzen - Google Patents
Verfahren zur bekämpfung von schadpilzen Download PDFInfo
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- WO2008025732A1 WO2008025732A1 PCT/EP2007/058807 EP2007058807W WO2008025732A1 WO 2008025732 A1 WO2008025732 A1 WO 2008025732A1 EP 2007058807 W EP2007058807 W EP 2007058807W WO 2008025732 A1 WO2008025732 A1 WO 2008025732A1
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- compound
- general formula
- harmful fungi
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Classifications
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Definitions
- the present invention relates to a method of controlling harmful fungi having a resistance to carboxylic acid amide fungicides.
- carboxylic acid amide fungicides include, but are not limited to, various cinnamic acid amide derivatives (see, for example, U.S. 5,952,496), valinamide carbamates (see, for example, DE 4026966), mandelic acid amides, and other carboxylic acid amide derivatives.
- Important constituents of commercial products include the carboxylic acid amide fungicides dimethomorph, benthiavalicarb, flumorph, iprovalicarb and mandipropamide.
- cinnamic acid derivatives described in US Pat. No. 5,952,496 have also proven to be of particular importance for the control of harmful fungi. These can be formulated, for example, in solution, as an aqueous emulsion or as a powder preparation and applied in this form to useful plants.
- An object of the present invention is to provide a novel method of controlling harmful fungi that may already have resistance to certain fungicides.
- the process should be technically easy to use, lead to an efficient prevention or elimination of harmful fungi and can be applied gently to various types of crops.
- the object is achieved by a method for controlling harmful fungi which are resistant to individual carboxylic acid amide fungicides, which comprises applying a fungicidally effective amount of a compound of general formula (I) to the plants, the seeds and / or the soils before or after Sowing of the plants or before or after the expiry of the plants applies, which happens in particular preventive.
- a method for controlling harmful fungi which are resistant to individual carboxylic acid amide fungicides, which comprises applying a fungicidally effective amount of a compound of general formula (I) to the plants, the seeds and / or the soils before or after Sowing of the plants or before or after the expiry of the plants applies, which happens in particular preventive.
- the process according to the invention uses a fungicidally effective amount of a compound of the general formula (I)
- the method is particularly suitable for controlling harmful fungi of the Plasmopara type, in particular Plasmopara viticola.
- -R means: -OCH 3 ,
- -X means: -Cl or -F
- -X means: -Cl
- the compound of the general formula (I) or a salt of this compound is usually applied in an amount of 1 to 1000 g / ha or in quantities of 1 to 1000 g / 100 kg of seed.
- the compound of the general formula (I) is preferably applied to the underside of the leaves of the plants to be treated.
- the treated plants may in particular also be grapevines.
- Another object of the invention is the use of a compound of general formula (I) for the preparation of a fungicidal preparation for preventive PiIz- control in crops, especially in already occurred resistances.
- a compound of general formula (I) for the prevention of cross-resistance in fungal control of crops is the subject of this invention.
- the abovementioned active compounds of the general formula (I) can be used in particular for controlling Plasmopara viticola, e.g. be used on grapevines.
- the compounds of general formula (I) are also suitable for controlling harmful fungi from the class of Peronosporomyctes (Oomycetes), such as:
- the method according to the invention is preferably suitable for the preventive control of Plasmopara harmful fungi, in particular of Plasmopara viticola strains.
- Plas- mopara viticola the downy mildew of the vine, is also known as vine peronospora. On the vine leaves, it first forms roundish, yellowish, oily, translucent spots on the upper side of the leaves, later in humid weather, dense white mushroom grass on the underside.
- Berries can also affect all green vine parts, shoot tips, tendrils and inflorescences. Berries, for example, turn brown and shrink.
- the fungus Plasmo- para viticola penetrates through the stomata into the tissue of the green Reborgane. The infection then takes place via zoospores floating in a water film. In the vicinity of stomata they settle and form a germ tube. With the help of nutritional organs, the fungus takes valuable food from the host plant.
- the disease is of particular economic importance, as an epidemic-like occurrence is possible, and the grape infestation can cause severe loss of yield up to the total loss of the harvest. Furthermore, infestation with Plasmopara increases the frost sensitivity of the vine.
- the o. G. The method is applied by treating the fungi or the plants, seeds, materials and / or the soil to be protected against fungal attack with a fungicidally effective amount of the compound of the formula (I).
- the application can take place before as well as promptly with the infection, but preferably before the infection of the materials, plants or seeds by the fungi.
- the compounds of the formula (I) can be prepared by customary processes. They can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
- the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
- Suitable solvents / auxiliaries are essentially:
- solvent mixtures can also be used.
- aromatic solvents eg Solvesso products, xylene
- paraffins eg petroleum fractions
- alcohols eg methanol, butanol, pentanol, benzyl alcohol
- ketones eg cyclohexanone, gamma-butyrolactone
- pyrrolidones NMP, NOP
- Acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
- solvent mixtures can also be used
- ground natural minerals eg kaolins, clays, talc, chalk
- ground synthetic minerals eg fumed silica, silicates
- Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxygenated ethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants such as lignin-sulphite liquors and methylcellulose.
- mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
- mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or
- Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
- Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell meal, cellulose powder and other solid carriers.
- Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
- Seed treatment formulations may additionally contain binders and / or gelling agents and optionally dyes.
- Binders can be added to increase adhesion of the active ingredients to the seed after treatment.
- Suitable binders are, for example, EO / PO Block copolymer surfactants, but also polyvinyl alcohols, Ppolyvinylpyrrolidone, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrenes, polyethyleneamines, Polyethylenamide, polyethylenimines (Lupasol ®, Polymin ®), polyethers, polyurethanes, polyvinyl acetates, Tylose and copolymers of these polymers.
- carrageen (Satiagel ®).
- the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- the formulations in question give, after dilution of from two to ten times, active compound concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
- a compound I according to the invention 10 parts by weight of a compound I according to the invention are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with an active ingredient content of 10% by weight.
- a compound I according to the invention 15 parts by weight of a compound I according to the invention are dissolved in 75 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
- the formulation has an active substance content of 15% by weight.
- a compound I according to the invention 25 parts by weight of a compound I according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
- This mixture is added by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight of water and made into a homogeneous emulsion. Dilution in water results in an emulsion.
- the formulation has an active ingredient content of 25% by weight.
- a compound I according to the invention 20 parts by weight of a compound I according to the invention are comminuted with the addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to give a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
- the active ingredient content in the formulation is 20% by weight.
- Water-dispersible and water-soluble granules 50 parts by weight of a compound I according to the invention are finely ground with the addition of 50 parts by weight dispersing and wetting agents and by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble Granules produced. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the formulation has an active ingredient content of 50% by weight.
- a compound I according to the invention 75 parts by weight of a compound I according to the invention are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
- the active ingredient content of the formulation is 75% by weight.
- a compound I according to the invention are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with an active ingredient content of 0.5 wt .-%.
- the active compounds may be used as such, in the form of their formulations or the forms of use prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, misting, dusting, scattering or pouring.
- the forms of application depend entirely on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
- the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
- wetting agents To the active ingredients oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use (tank mix), are added. These agents can be added to the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1.
- organically modified polysiloxanes eg Break Thru S 240 ®
- Alcohol alkoxylates eg. As Atplus 245 ®, Atplus MBA 1303 ®, Plurafac LF 300 ® and Lutensol ON 30 ®
- EO-PO block polymers eg. B. Pluro- nic RPE 2035 ® and Genapol B ®
- Alcohol ethoxylates eg. As Lutensol XP 80 ®
- sodium dioctylsulfosuccinate e. B. Leophen RA ®.
- the application rates are depending on the application pressure and type of effect desired between 1 and 100Og, preferably 20 and 750g active ingredient per ha.
- the fungicidal compositions according to the invention generally contain between 0.1 and 95, preferably between 0.5 and 90 wt. -% of one or more active substances.
- amounts of active ingredient in the seed treatment, in general, amounts of active ingredient of from 1 to 1000 g, preferably from 1 to 200 g, in particular from 5 to 100 g, per kilogram of seed are required.
- the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates in the protection of the material are, for example, from 0.001 g to 2000 g, preferably from 0.005 g to 1000 g of active ingredient per cubic meter of material treated.
- the use of compounds of general formula (I) may also be carried out in combination with other active substances, e.g. with herbicides, insecticides, growth regulators, other fungicides or with fertilizers.
- other active substances e.g. with herbicides, insecticides, growth regulators, other fungicides or with fertilizers.
- Azoxystrobin dimoxystrobin, enestroburine, fluoxastrobin, kresoxim-methyl, metominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, (2-chloro-5- [1- (3-methyl-benzyloxyimino) -ethyl] -benzyl) -carbamic acid methyl ester, (2-Chloro-5- [1- (6-methylpyridin-2-ylmethoxyimino) ethyl] benzyl) -carbamic acid methyl ester, 2- (ortho- (2,5-dimethylphenyl-oxymethylene) -phenyl) -3- methoxy-methyl acrylate;
- bitertanol bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, fluquinconazole, flutriol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazo - Ie, triadimenol, triadimefon, triticonazole;
- - imidazoles cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
- Benzimidazoles benomyl, carbendazim, fuberidazole, thiabendazole; - Other: Ethaboxam, Etridiazole, Hymexazole;
- Pyridines fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-dimethylisoxazolidin-3-yl] pyridine; Pyrimidines: bupirimate, cyprodinil, ferimzone, fenarimol, mepanipyrim, nuarimol, pyrimethanil;
- Morpholines aldimorph, dodemorph, fenpropimorph, tridemorph;
- Dicarboximides iprodione, procymidone, vinclozolin;
- acibenzolar-S-methyl anilazine, captan, captafol, dazomet, diclomethine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilon, quinoxyfen, tricyclazole, 5-chloro-7- ( 4-methyl-piperidin-1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] pyrimidine, 2-butoxy-6- iodo-3-propyl-chromen-4-one, 3- (3-bromo-6-fluoro-2-methylindol-1-sulfonyl) - [1, 2,4] triazole-1-sulfonic acid dimethylamide;
- guanidines dodine, iminoctadine, guazatine
- Organometallic compounds fentin salts
- Sulfur-containing heterocyclyl compounds isoprothiolanes, dithianone
- Organophosphorus compounds edifenphos, fosetyl, fosetyl-aluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
- Organochlorine compounds thiophanates methyl, chlorothalonil, dichlofluanid, toiylfluanid, flusulphamides, phthalides, hexachlorobenzene, pencycuron, quintozene; Nitrophenyl derivatives: binapacryl, dinocap, dinobuton;
- alkyl also includes octyl, decyl, tetradecyl and
- Guazatine mixture of the reaction products obtained from the amidation of technical lminodi (octamethylene) diamine containing various guanidines and polyamines [CAS RN 108173-90-6];
- Spiroxamine (8-tert-butyl-1,4-dioxaspiro [4.5] dec-2-yl) diethylamine (EP-A 281 842); Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 1 164 152);
- Cycloheximide 4 - ⁇ (2R) -2 - [(1S, 3S, 5S) -3,5-dimethyl-2-oxocyclohexyl] -2-hydroxyethyl ⁇ piperidine-2,6-dione [CAS RN 66- 81-9]; Griseofulvin, 7-chloro-2 ', 4,6-trimethoxy-6'-methylspiro [benzofuran-2 (3H), 1'-cyclohex-2'-ene] -3,4'-dione [CAS RN 126-07 -8th];
- Enilconazole (imazalil), 1 - [2- (2,4-dichlorophenyl) -2- (2-propenyloxy) ethyl] -1H-imidazole (Fruits 28, p. 545, 1973);
- Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12.
- Prothioconazole 2- [2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl] -2,4-dihydro- [1,2,4] triazole-3-thione (WO 96/16048) ; Simeconazole, ⁇ - (4-fluorophenyl) - ⁇ - [(trimethylsilyl) methyl] -1H-1,2,4-triazole-1-ethanol
- Triticonazole (5 lbs) -5 - [(4-chlorophenyl) methylene] -2,2-dimethyl-1- (1 H -1, 2,4-triazol-1-ylmethyl) cyclopentanol (FR 26 41 277);
- Maneb manganese ethylene bis (dithiocarbamate) (US 2 504 404); Mancozeb, manganese ethylene bis (dithiocarbamate) polymer complex zinc salt
- Metiram zinc ammonium ethylenebis (dithiocarbamate) (U.S. 3,248,400);
- Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
- Zineb zinc ethylene bis (dithiocarbamate) (US 2 457 674);
- Oxycarboxine, 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide 4,4-dioxide (US 3,399,214);
- Cyazofamide 4-chloro-2-cyano- ⁇ /, ⁇ / -dimethyl-5- (4-methylphenyl) -1 / - / - imidazole-1-sulfonamide (CAS RN 120116-88-3];
- Famoxadone (/? S) -3-anilino-5-methyl-5- (4-phenoxyphenyl) -1,3-oxazolidine-2,4-dione [CAS RN 131807-57-3];
- Furametpyr 5-Chloro- ⁇ / - (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88- 3];
- Isoprothiolane, diisopropyl 1, 3-dithiolan-2-ylidenemalonate Proc. Insectic. Fungic. Conf.
- Copper oxychloride Cu 2 Cl (OH) 3 [CAS RN 1332-40-7]; Basic copper sulfate, CuSO 4 [CAS RN 1344-73-6];
- Propylpentyl is (US 2 526 660); Dinobutone, (RS) -2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21-7];
- Nitrothal isopropyl, diisopropyl 5-nitroisophthalate Proc. Br. Insectic. Fungic. Conf.
- Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
- Cymoxanil 1- (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (U.S. 3,957,847); Diclomezine, 6- (3,5-dichlorophenyl-p-tolyl) pyridazine-3 (2 / - /) -one (US 4 052 395)
- Fosetyl, Fosetyl aluminum, ethyl phosphonate (FR 22 54 276);
- Metrafenone 3'-bromo-2,3,4,6'-tetramethoxy-2 ', 6-dimethylbenzophenone (U.S. 5,945,567); Pencycuron, 1- (4-chlorobenzyl) -1-cyclopentyl-3-phenylurea (DE-A 27 32 257);
- Phthalide (DE-A 16 43 347); Toloclofos-methyl, O-2,6-dichloro-p-tolyl 0,0-dimethyl phosphorothioate (GB 14 67 561);
- Picoxystrobin 3-methoxy-2- [2- (6-trifluoromethyl-pyridin-2-yloxymethyl) -phenyl] -acrylic acid methyl ester (EP-A 278 595);
- Pyraclostrobin N- ⁇ 2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl ⁇ (N-methoxy) carbamic acid methyl ester (WO 96/01256); Trifloxystrobin, (E) -methoxyimino- ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl ⁇ -acetic acid methyl ester (EP-A 460 575);
- the compounds of general formula (I) may be used with said other fungicides together in generally conventional formulations, e.g. as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- formulations are prepared by known methods.
- the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of active ingredients.
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredient can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- Stock solution A was prepared from dimethomorph ((E, Z) -4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloy] morpholine) at 150 g / l as dispersible concentrate (d.c.).
- Stock B was prepared from mandipropamide ((RS) -2- (4-chlorophenyl) -N- [3-methoxy-4- (prop-2-ynyloxy) phenethyl] -2- (prop-2-ynyloxy) acetamide) 40g / l emulsifiable concentrate (ec) produced.
- Stock solution C was prepared from iprovalicarb
- the fungicidal active ingredients described in Example 1 are applied both one day before the treatment with the harmful fungi (preventive treatment) and in each case one day after the treatment with the harmful fungi (curative treatment). After treatment with the harmful fungi, the plants are allowed to stand at 95% humidity and a temperature of 18 ° C overnight. This is followed by an observation phase for 6 days and a final evaluation on the 6th day, the test plants are exposed to daylight for 12 hours each and left in the dark for 12 hours.
- the undersides of the vine leaves are sprayed with water for 24 hours before the end of the evaluation and allowed to stand.
- the evaluation of the experiments is carried out by a determination of the percentage of diseased leaf area of each plant.
- a high percentage value means a high degree of harmful fungus disease
- a low percentage value means a low level of harmful fungus disease.
- a curative treatment resulted in an attack of 65% of the leaf area for the resistant fungi and an infestation of 0% for the sensitive fungi.
- the preventive treatment resulted in an attack of 8% of the leaf area for the resistant fungi and an infestation of 0% of the leaf area for the sensitive fungi.
- curative treatment resulted in an attack of 75% of the resistant fungi and an infestation of 0% in the sensitive fungi.
- Preventive treatment resulted in an attack of 70% of the area for the resistant fungi and an attack of 0% of the surface for the sensitive fungi.
- curative treatment resulted in an attack of 70% of the area for the resistant fungi and an infestation of 0% for the sensitive fungi.
- Preventive treatment resulted in an attack of 55% of the surface area for the resistant fungi and an infestation of 0% of the surface area for the sensitive fungi.
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- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MX2009001086A MX2009001086A (es) | 2006-08-28 | 2007-08-24 | Metodo para controlar hongos dañinos. |
US12/438,963 US20100210652A1 (en) | 2006-08-28 | 2007-08-24 | Method For Controlling Fungal Pests |
CA002657361A CA2657361A1 (en) | 2006-08-28 | 2007-08-24 | Method for controlling fungal pests |
JP2009526058A JP2010501619A (ja) | 2006-08-28 | 2007-08-24 | 有害菌を防除する方法 |
BRPI0714658-2A BRPI0714658A2 (pt) | 2006-08-28 | 2007-08-24 | processo para combater fungos nocivos que sço resistentes aos fungicidas de carboxamida |
AU2007291351A AU2007291351A1 (en) | 2006-08-28 | 2007-08-24 | Method for controlling fungal pests |
EA200900271A EA200900271A1 (ru) | 2006-08-28 | 2007-08-24 | Способ борьбы с вредными грибами |
EP07802856A EP2066175A1 (de) | 2006-08-28 | 2007-08-24 | Verfahren zur bekämpfung von schadpilzen |
IL196504A IL196504A0 (en) | 2006-08-28 | 2009-01-14 | Method for controlling fungal pests |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06119625.9 | 2006-08-28 | ||
EP06119625 | 2006-08-28 |
Publications (1)
Publication Number | Publication Date |
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WO2008025732A1 true WO2008025732A1 (de) | 2008-03-06 |
Family
ID=38963095
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/058807 WO2008025732A1 (de) | 2006-08-28 | 2007-08-24 | Verfahren zur bekämpfung von schadpilzen |
Country Status (16)
Country | Link |
---|---|
US (1) | US20100210652A1 (de) |
EP (1) | EP2066175A1 (de) |
JP (1) | JP2010501619A (de) |
KR (1) | KR20090045401A (de) |
CN (1) | CN101511182A (de) |
AR (1) | AR062554A1 (de) |
AU (1) | AU2007291351A1 (de) |
BR (1) | BRPI0714658A2 (de) |
CA (1) | CA2657361A1 (de) |
CL (1) | CL2007002508A1 (de) |
CR (1) | CR10659A (de) |
EA (1) | EA200900271A1 (de) |
IL (1) | IL196504A0 (de) |
MX (1) | MX2009001086A (de) |
WO (1) | WO2008025732A1 (de) |
ZA (1) | ZA200902116B (de) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013169664A2 (en) * | 2012-05-07 | 2013-11-14 | Dow Agrosciences Llc | Macrocycle picolinamides as fungicides |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988005630A1 (en) * | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co. Kg | Fungicidal compositions |
EP0520585A1 (de) * | 1991-06-28 | 1992-12-30 | Shell Internationale Researchmaatschappij B.V. | Fungizide Zusammensetzungen |
EP0783836A1 (de) * | 1996-01-11 | 1997-07-16 | Agrogene, Ltd. | Synergistische fungizide Mischungen zur Bekämpfung von Pflanzenkrankheiten |
EP0860438A1 (de) * | 1997-02-21 | 1998-08-26 | Shenyang Research Institute of Chemical Industry | Fluorine enthaltende Diphenylacrylamid Microbizide |
WO2001087822A1 (en) * | 2000-05-17 | 2001-11-22 | Syngenta Participations Ag | Novel phenyl-propargylether derivatives |
-
2007
- 2007-08-24 EA EA200900271A patent/EA200900271A1/ru unknown
- 2007-08-24 JP JP2009526058A patent/JP2010501619A/ja not_active Withdrawn
- 2007-08-24 CN CNA200780032078XA patent/CN101511182A/zh active Pending
- 2007-08-24 KR KR1020097006269A patent/KR20090045401A/ko not_active Application Discontinuation
- 2007-08-24 US US12/438,963 patent/US20100210652A1/en not_active Abandoned
- 2007-08-24 AU AU2007291351A patent/AU2007291351A1/en not_active Abandoned
- 2007-08-24 BR BRPI0714658-2A patent/BRPI0714658A2/pt not_active IP Right Cessation
- 2007-08-24 EP EP07802856A patent/EP2066175A1/de not_active Withdrawn
- 2007-08-24 WO PCT/EP2007/058807 patent/WO2008025732A1/de active Application Filing
- 2007-08-24 CA CA002657361A patent/CA2657361A1/en not_active Abandoned
- 2007-08-24 MX MX2009001086A patent/MX2009001086A/es not_active Application Discontinuation
- 2007-08-27 AR ARP070103800A patent/AR062554A1/es not_active Application Discontinuation
- 2007-08-28 CL CL200702508A patent/CL2007002508A1/es unknown
-
2009
- 2009-01-14 IL IL196504A patent/IL196504A0/en unknown
- 2009-03-11 CR CR10659A patent/CR10659A/es not_active Application Discontinuation
- 2009-03-26 ZA ZA200902116A patent/ZA200902116B/xx unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988005630A1 (en) * | 1987-01-30 | 1988-08-11 | Shell Agrar Gmbh & Co. Kg | Fungicidal compositions |
EP0520585A1 (de) * | 1991-06-28 | 1992-12-30 | Shell Internationale Researchmaatschappij B.V. | Fungizide Zusammensetzungen |
EP0783836A1 (de) * | 1996-01-11 | 1997-07-16 | Agrogene, Ltd. | Synergistische fungizide Mischungen zur Bekämpfung von Pflanzenkrankheiten |
EP0860438A1 (de) * | 1997-02-21 | 1998-08-26 | Shenyang Research Institute of Chemical Industry | Fluorine enthaltende Diphenylacrylamid Microbizide |
WO2001087822A1 (en) * | 2000-05-17 | 2001-11-22 | Syngenta Participations Ag | Novel phenyl-propargylether derivatives |
Non-Patent Citations (6)
Title |
---|
A. SUTY & K. STENZEL: "Iprovalicarb - Sensitivity of Phytophthora infestans and Plasmopara viticola: determination of baseline sensitivity and assessment of the risk of reistance", PFLANZENSCHUTZ-NACHRICHTEN BAYER, vol. 52, no. 1, 1999, pages 71 - 82, XP002466890, Retrieved from the Internet <URL:http://www.bayercropscience.com/bayer/cropscience/cscms.nsf/ID/6thArticle011999_EN/$file/Suty_6.pdf> [retrieved on 20080129] * |
BASIL N ZIOGAS ET AL: "A High Multi-drug Resistance to Chemically Unrelated Oomycete Fungicides in Phytophthora infestans", EUROPEAN JOURNAL OF PLANT PATHOLOGY, KLUWER ACADEMIC PUBLISHERS, DO, vol. 115, no. 3, 16 May 2006 (2006-05-16), pages 283 - 292, XP019394875, ISSN: 1573-8469 * |
K. J. BRENT & D. W. HOLLOMON: "Fungicide resistance in crop pathogens: how can it be managed? (FRAC Monograph No. 1, 2nd, revised ed.)", 2007, CROPLIFE INTERNATIONAL/FRAC, BRUSSELS, ISBN: 90-72398-07-6, XP002466893 * |
N. A. MARTIN, R. M. BERESFORD & K. C. HARRINGTON (EDS.): "Pesticide resistance: Prevention and management strategies 2005", 2005, NEW ZEALAND PLANT PROTECTION SOCIETY INC., HASTINGS, NZ, ISBN: 0-473-10441-5, XP002466892 * |
S. K. YUAN ET AL.: "Sensitivity of Phytophthora infestans to flumorph: in vitro determination of baseline sensitivity and the risk of resistance", PLANT PATHOLOGY, vol. 55, no. 2, April 2006 (2006-04-01), pages 258 - 263, XP002466889 * |
U. GISI ET AL.: "Inheritance of resistance to carboxylic acid amide (CAA) fungicides in Plasmopara viticola", PLANT PATHOLOGY, vol. 56, no. 2, April 2007 (2007-04-01), pages 199 - 208, XP002466891 * |
Also Published As
Publication number | Publication date |
---|---|
AR062554A1 (es) | 2008-11-19 |
BRPI0714658A2 (pt) | 2013-05-07 |
EP2066175A1 (de) | 2009-06-10 |
IL196504A0 (en) | 2009-11-18 |
CL2007002508A1 (es) | 2008-04-11 |
US20100210652A1 (en) | 2010-08-19 |
JP2010501619A (ja) | 2010-01-21 |
ZA200902116B (en) | 2010-06-30 |
CN101511182A (zh) | 2009-08-19 |
CA2657361A1 (en) | 2008-03-06 |
MX2009001086A (es) | 2009-02-10 |
EA200900271A1 (ru) | 2009-08-28 |
KR20090045401A (ko) | 2009-05-07 |
CR10659A (es) | 2009-04-03 |
AU2007291351A1 (en) | 2008-03-06 |
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