WO2008155416A2 - Gibbérellines comme phytoprotecteurs de sécurité pour des fongicides présentant une activité phytotoxique - Google Patents

Gibbérellines comme phytoprotecteurs de sécurité pour des fongicides présentant une activité phytotoxique Download PDF

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Publication number
WO2008155416A2
WO2008155416A2 PCT/EP2008/057892 EP2008057892W WO2008155416A2 WO 2008155416 A2 WO2008155416 A2 WO 2008155416A2 EP 2008057892 W EP2008057892 W EP 2008057892W WO 2008155416 A2 WO2008155416 A2 WO 2008155416A2
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WIPO (PCT)
Prior art keywords
gibberellin
fungicide
azole
fungicides
seeds
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PCT/EP2008/057892
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English (en)
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WO2008155416A3 (fr
Inventor
Thomas J. Holt
Hendrik Leonard Ypema
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Basf Se
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Publication of WO2008155416A3 publication Critical patent/WO2008155416A3/fr

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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • 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
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring

Definitions

  • the present invention relates to the use of at least one gibberellin for reducing or preventing the phytotoxic effect of azole fungicides or of azole fungicides used in combination with anilide fungicides on plants the seeds or the growing medium of which have been treated with these fungicides.
  • the invention also relates to a method for reducing or preventing the phytotoxic effect of azole fungicides or of azole fungicides used in combination with anilide fungicides on plants the seeds or the growing medium of which have been treated with these fungicides by treating the seeds or the growing medium of the seeds also with at least one gibberellin.
  • a further aspect of the invention is a method for controlling phytopathogenic fungi which comprises treating the seeds of a plant or the growing medium of the seeds with at least one azole fungicide in combi- nation with at least one gibberellin and optionally at least one anilide fungicide.
  • the invention relates to a composition comprising at least one azole fungicide, at least one gibberellin and optionally at least one anilide fungicide.
  • WO 2007/065843 describes the use of a gibberellin as safener for azole fungicides. Explicitely, only the use of gibberellic acid and only for the purpose of reversing the stunting effect and the delayed or impeded germination of azole fungicides is disclosed.
  • the safening effect should not be limited to reversing the phytotoxic effects of azole fungicides used alone, but also of azole fungicides used in combination with anilide fungicides. Additionally or alternatively the safeners should show less side effects than the safeners of the prior art.
  • gibberellins prevent, or at least reduce, the phyto- toxic effects of such fungicides.
  • the invention relates to a method for controlling phytopathogenic fungi which comprises treating the seeds of a plant or the growing medium of the seeds with at least one azole fungicide in combination with at least one gibberellin and optionally at least one anilide fungicide.
  • the invention in a second aspect, relates to a method for reducing or preventing the phytotoxic effect of azole fungicides or of azole fungicides used in combination with anilide fungicides on plants the seeds or the growing medium of which have been treated with at least one azole fungicide and optionally with at least one anilide fungicide, which method comprises treating the seeds or the growing medium of the seeds with at least one azole fungicide and optionally at least one anilide fungicide in combination with at least one gibberellin.
  • the invention relates to the use of at least one gibberellin for reducing or preventing the phytotoxic effect of azole fungicides or of azole fungicides used in combination with anilide fungicides on plants the seeds or the growing medium of which have been treated with at least one azole fungicide and optionally at least one anilide fungicide.
  • the invention in a fourth aspect, relates to a composition
  • a composition comprising at least one azole fungicide, at least one gibberellin and optionally at least one anilide fungicide.
  • safener is used for substances which reduce or prevent the damage to crop plants as the result of herbicides which are employed for destroying weeds.
  • this term is defined in more gen- eral terms and refers to substances which reduce or prevent the phytotoxic effect of crop protectants, in the present context specifically fungicides, on plants whose seeds or growth medium have been treated or are treated therewith.
  • the subject matter of the present invention relates to the use of at least one gibberellin for reducing or preventing the phytotoxic effect of the above-named fungicides on plants whose seeds or whose growth substrates have been treated, or are treated, with these fungicides.
  • seed represents all types of plant propagation material. It comprises seeds in the actual sense, grains, fruits, tubers, the rhizome, spores, cuttings, slips, meristem tissue, individual plant cells and any form of plant tissue from which a complete plant can be grown. Preferably, it takes the form of seed in the actual sense.
  • “Growing medium”, “growth medium” or “growth substrate” refers to any type of substrate in which the seed is sown and the plant grows or will grow, such as soil (for example in a pot, in borders or in the field) or artificial media. As a rule, it takes the form of the soil.
  • the gibberellins are preferably selected among those of the formula I
  • R represents a hydrogen atom or a hydroxyl group; and " "" means that a single bond or a C-C double bond is present at this position.
  • the gibberellin is in particular selected from gibberellic acid (gibberellin A3) of the for- mula (I-2), gibberellin A 4 of the formula (I-3), gibberellin A7 of the formula (I-4) and a mixture thereof. More preferably the gibberellin is selected from gibberellin A 4 of the formula (I-3), gibberellin A 7 of the formula (I-4) and a mixture thereof. Even more preferably, the gibberellin is selected from a mixture of gibberellin A 4 of the formula (I-3) and gibberellin A 7 of the formula (I-4).
  • the gibberellin is more preferably selected from gibberellin A 4 of the formula (I-3), gibberellin A 7 of the formula (I-4) and from a mixture thereof, and specifically from a mixture thereof.
  • the combined use of azole fungicides, anilide fungicides and gibberellins different from gibberellin A 4 and gibberellin A 7 , in particular gibberellin A3, on the one side effectively reduces the phytotoxic activity of the fungicides, but, on the other side, in some cases may lead to secondary undesired effects caused by this specific combination, specifically to an enhanced stand loss.
  • gibberellin A 4 gibberellin A 7 or more preferably a mixture thereof in these specific combinations. If a mixture of gibberellin A 4 and gibberellin A 7 is used, the two gibberellins are preferably present in a weight ratio of 20:1 to 1 :20, more preferably 10:1 to 1 :10, even more preferably 5:1 to 1 :5, in particular 2:1 to 1 :2 and specifically about 1 :1.
  • Azole fungicides also referred to as conazole fungicides, are fungicidally active compounds which comprise an aromatic 5-membered heterocycle containing at least one nitrogen atom as ring member.
  • they comprise an imidazole ring ("imidazole conazoles”) or a triazole ring (“triazole conazoles”).
  • Azole fungicides and processes for their preparation are, in principle, known to the skilled worker and described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which are herewith incorporated by reference.
  • Preferred azole fungicides are those which are known by the common names biter- tanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, metcona- zole, myclobutanil, paclobutrazole, penconazole, prochloraz, propiconazole, prothio- conazole, tebuconazole, triadimefon, triadimenol, triflumizole and triticonazole.
  • azole fungicides are selected among difenoconazole, epoxiconazole, fluquinconazole, flutriafol, imazalil, metconazole, paclobutrazole, prochloraz, propiconazole, prothioconazole, tebuconazole, triadimenol and triticonazole. More preferred are the azole fungicides selected among epoxiconazole, fluquinconazole, flutria- fol, prothioconazole, tebuconazole and triticonazole and even more preferred among epoxiconazole, fluquinconazole and triticonazole. In particular, they are selected among fluquinconazole and triticonazole. Specifically, the azole fungicide is triticonazole.
  • Anilide fungicides and processes for their preparation are, in principle, known to the skilled worker and described, for example, in Farm Chemicals Handbook, Meister Pub- lishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which are herewith incorporated by reference.
  • Preferred anilide fungicides are those which are known by the common names benal- axyl, benalaxyl-M, boscalid, carboxin, fenhexamid, isotianil, metalaxyl, metalaxyl-M, metsulfovax, ofurace, oxadixyl, oxycarboxin, pyracarbolid, thifluzamide and tiadinil, benzanilide fungicides, such as benodanil, flutolanil, mebenil, mepronil, salicylanilide and tecloftalam, furanilides, such as fenfuram, furalaxyl, furcarbanil and methfuroxam, and sulfanilides, such as flusulfamide.
  • anilide fungicides are selected from benalaxyl, benalaxyl-M, boscalid, carboxin, fenhexamid, isotianil, metalaxyl, metalaxyl-M, metsulfovax, ofurace, oxadixyl, oxycarboxin, pyracarbolid, thifluzamide and tiadinil.
  • metalaxyl and metalaxyl-M metalaxyl being the unresolved isomeric mixture of the R and S enantiomers and metalaxyl-M, which is also known as mefenoxam, being the R enantiomer.
  • metalaxyl- M (mefenoxam) is used as anilide fungicide.
  • fungicides and gibberellins can also be employed in the form of their agriculturally tolerated salts.
  • all compounds which comprise basic nitrogen atoms in the molecule can be employed in the form of their acid addition salts.
  • Compounds with abstractable protons can be employed in the form of their salts with metal cations, ammonium ions, phosphonium ions, sulfonium ions or sulfoxonium ions.
  • the acid addition salts can be prepared for example by reaction of the free bases with a suitable Bronsted acid.
  • Suitable acids have agriculturally tolerated acid anions and are selected for example among hydrohalic acids such as hydrofluoric acid, hydrochlo- ric acid, hydrobromic acid, and hydriodic acid, sulfuric acid, phosphoric acid, nitric acid, benzoic acid and Ci-C4-alkanoic acids such as formic acid, acetic acid, propionic acid and butyric acid.
  • suitable cations are, in particular, the cations of the alkali metals, prefera- bly lithium, sodium or potassium, of the alkaline earth metals, preferably calcium, magnesium or barium, and of the transition metals, preferably manganese, copper, zinc or iron.
  • Suitable ammonium cations are the ammonium cation itself (NH 4 + ) and also substituted ammonium ions in which 1 to 4 of the hydrogen atoms are replaced by C1-C4- alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4- alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • ammonium ions comprise methylammonium, ethylammonium, propylammonium, isopropylammonium, butylam- monium, dimethylammonium, diethylammonium, dipropylammonium, diisopropylam- monium, dibutylammonium, trimethylammonium, triethylammonium, tripropylammo- nium, tributylammonium, tetramethylammonium, tetraethylammonium, tetrapropylam- monium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl- ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl- triethylammonium.
  • phosphonium ions such as tri(Ci- C4-alkyl)sulfonium
  • sulfonium ions such as tri(Ci- C4-alkyl)sulfonium
  • sulfoxonium ions such as tri(Ci-C4.alkyl)sulfoxonium.
  • Ci-C4-Alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
  • Ci-C4-Hydroxyalkyl represents a Ci-C4-alkyl radical in which at least one hydrogen atom is replaced by a hydroxyl group.
  • Examples are hydroxym ethyl, 1- and 2- hydroxyethyl, 1 ,2-dihydroxyethyl, 1-, 2- and 3-hydroxypropyl, 1 ,2-dihydroxypropyl, 1 ,3- dihydroxypropyl, 2,3-dihydroxypropyl, 1 ,2,3-trihydroxypropyl, 1-, 2-, 3- and 4-hydroxybutyl and the like.
  • Ci-C 4 -AIkOXy represents a Ci-C4-alkyl radical which is bonded via an oxygen atom. Examples are methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and tert-butoxy.
  • Ci-C4-Alkoxy-Ci-C4-alkyl represents a Ci-C4-alkyl radical in which at least one hydrogen atom is replaced by an alkoxy group.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, methoxyethyl, 1- and 2-ethoxyethyl, 1- and 2-propoxyethyl, 1- and 2- isopropoxyethyl, 1- and 2-butoxyethyl, 1- and 2-sec-butoxyethyl, 1- and 2- isobutoxyethyl, 1- and 2-tert-butoxyethyl, 1-, 2- and 3-methoxypropyl, 1-, 2- and 3- ethoxypropyl, 1-, 2- and 3-propoxypropyl, 1-, 2- and 3-isopropoxypropyl, 1-, 2- and 3- butoxypropyl, 1-, 2- and 3-sec-butoxy
  • Hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl represents a Ci-C4-alkyl radical, in which at least one hydrogen atom is replaced by at least one alkoxy group.
  • at least one hydrogen atom in the alkyl radical or in the alkoxy radical or in both is replaced by a hydroxyl group. Examples are (2-hydroxyethoxy)methyl, (2- und 3-hydroxypropoxy)- methyl, (2-hydroxyethoxy)ethyl, (2- and 3-hydroxypropoxy)-1 -ethyl, (2- and 3-hydroxy- propoxy)-2-ethyl, 2-ethoxy-1-hydroxyethyl and the like.
  • Gibberellins which comprise a carboxyl group in the molecule may be employed not only in the form of their salts, but also in ester form. Suitable esters are in particular those with Ci-C4-alkanols such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol and tert- butanol.
  • gibberellins as safeners reduces or prevents the phytotoxic effect which certain azole fungicides or combinations of azole fungicides and anilide fungicides exert on the seeds treated therewith or on plants which are grown from seeds treated therewith or which grow in a growth substrate treated therewith.
  • the phytotoxic effect which these fungicides have can manifest itself in various ways and can be recognized by comparing plants whose seeds and/or whose growth substrate have been treated with a phytotoxically active fungicide and plants whose seeds and/or whose growth substrate have not been treated with this fungicide. Naturally, the comparison must be carried out under pathogen-free conditions since otherwise the untreated plants might, as the result of infection, display symptoms which correspond to the phytotoxic effects or are similar thereto.
  • the phytotoxic effect manifests itself for example in that seeds which have been treated with the fungicide in question and/or which are sown in a fungicide-treated growth substrate germinate more poorly. Poorer germination means that the same number of seeds gives rise to fewer seedlings in comparison with seeds which have not been treated with the fungicide in question and which grow in a correspondingly untreated growth substrate.
  • the phytotoxic effect may manifest itself in reduced emergence.
  • "Emergence” is understood as meaning that the seedling appears from the soil (or, in other words, that the coleoptil or the cotyledons or the shoot or the leaf break through the soil surface).
  • Reduced emergence means that fewer seedlings appear from the soil from the same number of seeds in comparison with seeds which have not been treated with the fungicide in question and which germinate and grow in a growth substrate which has not been treated correspondingly.
  • germination and emergence may coincide, i.e. the first cotyledon already appears from the soil. However, since this is not the case with all plants, germination and emergence are described separately.
  • the phytotoxic effect can manifest itself in reduced growth of the hypocotyl, i.e. the stalk does not grow as long as expected, and, possibly, leaves and apex lie on the ground. In terms of the present invention, this effect is also called "stunting effect". In some plants, such as cereals, this characteristic is not necessarily disadvantageous since it reduces or prevents lodging; in some plant species, however, such as legumes, it is entirely undesirable.
  • the vitality of a plant manifests itself in a variety of factors. Examples of factors which are manifestations of the plant's vitality are:
  • the phytotoxic effect can manifest itself in a worsening of at least one of the abovementioned factors, for example in
  • Biotic stress is caused by organisms, for example by pests (such as insects, arachnids, nematodes and the like), competing plants (for example weeds), phytopathogenic fungi and other microorganisms such as bacteria and viruses.
  • Abiotic stress is triggered for example by extreme temperatures such as heat, chill, great variations in temperature, or unseasonal temperatures, drought, extreme wetness, high salinity, radiation (for example increased UV radiation as the result of the diminishing ozone layer), increased amount of ozone in the vicinity of the soil and/or organic and inorganic pollution (for example as the result of phytotoxic amounts of pesticides or contamination with heavy metals).
  • Biotic and abiotic stress leads to a reduced quantity and/or quality of the stressed plant and its fruits.
  • the synthesis and accumulation of proteins is mainly adversely affected by temperature stress, while growth and polysaccharide synthesis are reduced by virtually all stress factors. This leads to biomass losses and to a reduced nutrient content of the plant product.
  • the invention relates to the use of the above-described gib- berellins for improving the vitality of plants whose seeds and/or whose growth medium have been treated, or are treated, with at least one azole fungicide and optionally also with at least one anilide fungicide as defined hereinabove.
  • the improved plant vigor manifests itself in an improved germination.
  • the invention relates to the use of the above-described gibberellins for improving the germination of plants whose seeds and/or growth medium have been treated, or are treated, with at least one azole fungicide and optionally also with at least one anilide fungicide as defined hereinabove.
  • Improved germination means that the same number of seeds gives rise to more seedlings in comparison with seeds which have been treated with the fungicide in question and/or which grow in a correspondingly treated growth substrate, but which have not been treated with a gibberellin or the growing medium of which has not been treated with a gibberellin.
  • the improved plant vigor additionally or alternatively
  • the invention relates to the use of the above-described gibberellins for improving the emergence of plants whose seeds and/or whose growth medium have been treated, or are treated, with at least one azole fungicide and optionally also with at least one anilide fungicide as defined hereinabove.
  • Improved emergence means that more seedlings appear from the soil from the same number of seeds in comparison with seeds which have been treated with the fungicide in question and/or which germinate and grow in a growth substrate which has been treated correspondingly, but which have not been treated with a gibberellin or the growing medium of which has not been treated with a gibberellin.
  • the improved plant vigor additionally or alternatively
  • the invention relates to the use of the above-described gibberellins for reducing or preventing the stunting effect of azole fungicides or of combinations of azole fungicides with anilide fungicides on plants whose seeds and/or whose growth medium have been treated, or are treated, with at least one azole fungicide and optionally also with at least one anilide fungicide as defined hereinabove, and thus for increasing the plant height of these plants.
  • Reduced/pre- vented stunting or increased plant height means that the hypocotyl, i.e.
  • the stalk is at the same point of time higher than the stalk of plants whose seeds or whose growth medium have been treated with the fungicide in question, but which have not been treated with a gibberellin or the growing medium of which has not been treated with a gibberellin.
  • the invention relates to the use of at least one of the above-mentioned gibberellins for improving the plant vigor, in particular for improving the germination and/or the emergence and/or for reducing/preventing the stunting, of plants whose seeds have been treated with a fungicide as defined hereinabove.
  • the plants can take the form of all plant species and plant varieties which are usually treated with the above-described fungicides and where a phytotoxic effect is observed as the result of this treatment.
  • these plants are agriculturally use- ful plants or else ornamentals.
  • Agriculturally useful plants are crop plants where parts or the entire plant act as a raw material for foodstuffs, feeding stuffs, fibers (for example cotton, linen), fuels (for example timber, bioethanol, biodiesel, biomass) or other chemical compounds.
  • Examples are cereals such as wheat (inclusive spelt, einkorn, emmer, kamut, durum and triticale), rye, barley, oats, rice, wild rice, maize (corn), mil- let, sorghum and teff, pseudocereals such as amaranth, quinoa and buckwheat, legumes of agricultural use such as bean, vegetable pea, fodder pea, chickpea, lentil, soybean and peanut, oilseed rape, sunflower, cotton, sugar beet, stone fruit, pome fruit, citrus fruit, banana, strawberry, blueberry, almond, grape, mango, pawpaw, potato, tomato, capsicum (pepper), cucumber, pumpkin/squash, melon, watermelon, gar- lie, onion, carrot, cabbage, lucerne, clover, flax, elephant grass (Miscanthus), grass, lettuce, sugar cane, tea, tobacco and coffee.
  • wheat inclusive spelt, einkorn, emmer, ka
  • Preferred agriculturally useful plants are selected from the above cereals, legumes, sunflower and sugar cane, more preferably from soybean, maize, wheat, triticale, oats, rye, barley, oilseed rape, millet, sorghum, rice, sunflower and sugar cane, and even more preferably from soybean, wheat, maize and oilseed rape.
  • the plant is soybean.
  • preferred agriculturally useful plants are selected among potato, tomato, capsicum (pepper), cucumber, pumpkin/squash, melon, watermelon, garlic, onion, carrot, cabbage, bean, vegetable pea, fodder pea and lettuce, more preferably among tomato, onion, lettuce and pea.
  • ornamentals are turf, geranium, pelargonium, petunia, begonia and fuch- sia, to mention only a few examples of a large number of ornamentals.
  • the plants can be non-transgenic or transgenic in nature.
  • the recombinant modification of the transgenic plant is such in nature that the plant has resistance to a certain pesticide.
  • the transgenic plant can have a resis- tance to the herbicide glyphosate.
  • transgenic plants are those with a resistance to herbicides from the group of the sulfonylurea (see, for example, EP-A- 0257993, US 5,013,659), the imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), of the glyfosinate type (see, for example, EP-A-0242236, EP-A-242246) or of the glyphosate type (see, for example, WO 92/00377) or plants with resistance to herbicides from the group of the cyclohexadienones/aryloxyphenoxypropionic acid herbicides (see, for example, US 5,162,602, US
  • a preferred transgenic plant is a transgenic soybean plant, preferably having a transgenic event that confers resistance to a pesticide, preferably for the herbicide glyphosate. Accordingly, it is preferred that the transgenic soybean plant be one having a transgenic event that provides glyphosate resistance. More preferably, the transgenic soybean plant has the characteristics of "Roundup-Ready" transgenic soybeans (available from Monsanto Company, St. Louis, Mo.).
  • trans- genie events that are present in the plant are by no means limited to those that provide pesticide resistance, but can include any transgenic event.
  • transgenic event any transgenic event.
  • the use of "stacked" transgenic events in a plant is also contemplated.
  • the present invention furthermore relates to a method of reducing or preventing the phytotoxic effect of azole fungicides or of azole fuingicides used in combination with anilide fungicides on plants whose seeds and/or whose growth substrates have been or are treated with these fungicides, where the plant' seed and/or its growth substrate is treated with at least one azole fungicide or with at least one azole fungicide and at least one anilide fungicide in combination with at least one of the above-described gibberellins.
  • the method is preferably used for reducing or preventing the phytotoxic effect of azole fungicides or of azole fuingicides used in combination with anilide fungicides on plants, whose seeds have been treated with at least one azole fungicide or with at least one azole fungicide and at least one anilide fungicide, where the seeds of the plant are treated with at least one azole fungicide or with at least one azole fungicide and at least one anilide fungicide in combination with at least one of the above-described gibberel- lins.
  • the method is preferably used for improving the germination and/or the emergence and/or the vitality, more preferably for improving the germination and/or the emergence and/or reducing/preventing the stunting of the plant treated thus.
  • the treatment of the plants' seed and/or its growth substrate can be accomplished for example in such a way that the seed and/or the growth substrate is treated with a mixture of the at least one azole fungicide, the at least one gibberellin and optionally the at least one anilide fungicide.
  • the seed and/or the growth substrate can be treated with the at least one azole fungicide, the at least one gibberellin and optionally the at least one anilide fungicide in separate form, it being possible for the treatment with the individual active substances to be accomplished simultaneously or in succession.
  • the time interval may be from a few seconds up to several months, for example up to 6, 8 or even 10 months. However, the time interval must be such that the desired effect can take place.
  • the interval between the treatments is relatively short, i.e. fungicide(s) and gibberellin are applied within a time interval of from a few seconds up to at most one month, especially preferably up to not more than one week and in particular up to not more than one day.
  • the different active substances to different subjects (subjects being, in the present context, seed and growth substrate), that is, for example, to treat the seed with one of the active substances, for example with the fungi- cide(s), and to apply the other active substance(s), for example the gibberellin, to the growth substrate therewith.
  • the sequence in which the individual active substances are applied is, as a rule, not critical.
  • this treatment preferably takes place before emergence of the plant.
  • the seed may be treated before sowing or else via the growth substrate into which it is sown, for example during sowing in the form of what is known as the in-furrow application.
  • the plant protectant is placed into the furrow essentially at the same time as the seed.
  • the seed is treated before sowing.
  • all customary methods of treating and in particular dressing such as coating (e.g. pelleting) and imbibing (e.g. soaking) seeds can be employed.
  • the preparation may be a formulation that is applied as such or after previously diluting it, e.g. with water; for instance, it may be expedient to dilute seed treatment formulations 2-10 fold leading to concentrations in the ready-to-use compositions of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.
  • a device which is suitable for this purpose for example a mixer for solid or solid/liquid components, is employed until the preparation is distributed uniformly on the seed.
  • the preparation can be applied to seeds by any standard seed treat- ment methodology, including but not limited to mixing in a container (e.g., a bottle, bag or tumbler), mechanical application, tumbling, spraying, and immersion. If appropriate, this is followed by drying.
  • Particular embodiments of the present invention comprise seed coating and imbibition (e.g. soaking).
  • Coating denotes any process that endows the outer surfaces of the seeds partially or completely with a layer or layers of non-plant material
  • imbibition any process that results in penetration of the active ingredient(s) into the ger- minable parts of the seed and/or its natural sheath, (inner) husk, hull, shell, pod and/or integument.
  • the invention therefore also relates to a treatment of seeds which com- prises providing seeds with a coating that comprises the active compounds used according to the invention, and to a treatment of seeds which comprises imbibition of seeds with the active compounds used according to the invention.
  • Coating is particularly effective in accommodating high loads of the active compounds, as may be required to treat typically refractory fungal pathogens, while at the same time excessive phytotoxicity is avoided.
  • Coating may be applied to the seeds using conventional coating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treat- ers, and drum coaters. Other methods such as the spouted beds technique may also be useful.
  • the seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing.
  • seed coating methods and apparatus for their application are disclosed in, for example, US 5,918,413, US 5,891 ,246, US 5,554,445, US 5,389,399, US 5,107,787, US 5,080,925, US 4,759,945 and US 4,465,017.
  • the active compounds used according to the invention can be mixed directly with seeds, for instance as a solid fine particulate formulation, e.g. a powder or dust.
  • a sticking agent can be used to support the adhesion of the solid, e.g. the powder, to the seed surface.
  • a quantity of seed can be mixed with a sticking agent (which increases adhesion of the particles on the surface of the seed) and optionally agitated to encourage uniform coating of the seed with the sticking agent.
  • the seed can be mixed with a sufficient amount of sticking agent, which leads to a partial or complete coating of the seed with sticking agent.
  • the seed pretreated in this way is then mixed with a solid formulation containing the active compounds used according to the invention to achieve adhesion of the solid formulation on the surface of the seed material.
  • the mixture can be agitated, for example by tumbling, to encourage contact of the sticking agent with the solid formulation of active compounds used according to the invention, thereby causing the active compounds used according to the invention to stick to the seed.
  • seed can be combined for a period of time with an aqueous solution comprising from about 1 % by weight to about 75% by weight of the active compounds in a solvent such as water.
  • concentration of the solution is from about 5% by weight to about 50% by weight, more preferably from about 10% by weight to about 25% by weight.
  • the seed takes up (imbibes) at least a portion of the active compounds.
  • the mixture of seed and solution can be agitated, for example by shaking, rolling, tumbling, or other means.
  • the seed can be separated from the solution and optionally dried in a suitable manner, for example by patting or air-drying.
  • the active compounds used according to the invention can be introduced onto or into a seed by use of solid matrix priming.
  • a quantity of the active compounds can be mixed with a solid matrix material, and then the seed can be placed into contact with the solid matrix material for a period to allow the active compounds to be introduced to the seed.
  • the seed can then optionally be separated from the solid matrix material and stored or used, or, preferably, the mixture of solid matrix material plus seed can be stored or planted/sown directly.
  • the ratio of the total weight of fungicide(s) employed according to the invention to the total weight of gibberellin(s) employed in accordance with the invention is preferably 200:1 to 1 :1 , e.g. 200:1 to 2:1 or 200:1 to 4:1 , more preferably 100:1 to 1 :1 , e.g. 100:1 to 2:1 or 100:1 to 4:1 , even more preferably 50:1 to 1 :1 , e.g. 50:1 to 2:1 or 50:1 to 4:1 , and specifically 30:1 to 1 :1 , e.g. 30:1 to 2:1 or 30:1 to 4:1.
  • the ratio of the total weight of azole fungicide ⁇ ) employed in accordance with the invention to the total weight of anilide fungicide ⁇ ) employed in accordance with the invention is preferably 100:1 to 1 :1 , e.g. 100:1 to 2:1 , more preferably 50:1 to 1 :1 , e.g. 50:1 to 2:1 , and even more preferably 30:1 to 1 :1 , e.g. 30:1 to 2:1.
  • weight ratio is preferably 20:1 to 1 :20, more preferably 10:1 to 1 :10, even more preferably 5:1 to 1 :5, in particular 2:1 to 1 :2 and specifically about 1 :1.
  • the active substances i.e. the at least one azole fungicide, the at least one gibberellin and the at least one optionally employed anilide fungicide
  • the use forms depend entirely on the intended purposes.
  • the active substances can be employed as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, tracking powders or granules.
  • the application is usually accomplished by spraying, misting, atomizing, scattering or pouring.
  • the use forms and use methods depend on the intended purposes; in any case, they should ensure the finest possible distribution of the active substances.
  • the ready-to-use preparations of the active substances comprise one or more liquid or solid carriers, optionally surface-active substances and optionally further adjuvants which are conventionally used for the formulation of plant protectants.
  • the compositions for such formulations are well known to the skilled worker.
  • Aqueous use forms can be prepared for example starting from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the active substances as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, adhesive, dispersant or emulsifier.
  • concentrates consisting of active substance, wetter, adhesive, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
  • the concentrations of the active substances in the ready-to-use preparations can be varied within substantial ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1 % (% by weight total active substance content based on the total weight of the ready-to-use preparation).
  • the active substances can also be employed successfully in the ultra-low-volume method (ULV), it being possible to apply formulations with more than 95% by weight of active substance, or indeed the active substances without additives.
  • insects such as bactericides, algi- cides, molluscicides, rodenticides, and bird/mammal repellents, safeners, fertilizers and/or growth regulators which are other than the gibberellins employed in accordance with the invention, if appropriate only just before use (tank mix).
  • Adjuvants within this meaning are, in particular, organic modified polysiloxanes, for example Break Thru S 240 ® ; alcohol alkoxylates, for example Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ® ; EO/PO block polymers, for example Pluronic RPE 2035 ® and Genapol B ® ; alcohol ethoxylates, for example Lutensol XP 80 ® ; and sodium dioctyl sulfosuccinate, for example Leophen RA ® .
  • organic modified polysiloxanes for example Break Thru S 240 ®
  • alcohol alkoxylates for example Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ®
  • EO/PO block polymers for example Pluronic RPE 2035 ® and Genapol B ®
  • the active ingredients can also be employed together with other active ingredients which are useful in seed treatment, for example together with fungicides, insecticides, molluscicides, nematicides, herbicides, algicides, bactericides, rodenticides, bird/mammal repellents, growth regulators, safeners or also fertiliz- ers.
  • anilinopyrimidines such as pyrimethanil, mepanipyrim and cyprodinil
  • dicarboximides such as iprodione, procymidone, vinclozolin
  • dithiocarbamates such as mancozeb, metiram and thiram
  • heterocylic compounds such as benomyl, carbendazim, fuberidazole, picobenzamid, penthiopyrad, proquinazid, thiabendazole and thiophanate- methyl;
  • phenylpyrroles such as fenpiclonil and fludioxonil
  • other fungicides for example benthiavalicarb, cyflufenamid, fosetyl, fosetyl- aluminium, phosphorous acid and its salts, iprovalicarb and metafenone
  • strobilurins such as azoxystrobin, dimoxystrobin, enestrobin, enestroburin, fluox- astrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclo- strobin, trifloxystrobin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)- ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methylpyridin-2-ylmethoxy- imino)eth
  • organo(thio)phosphates selected from acephate, azamethiphos, azinphos- methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosa- lone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos and trichlorfon;
  • pyrethroids selected from allethrin, bifenthrin, cycloprothrin, cyfluthrin, cy- halothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fen- valerate, flucythrinate, imiprothrin, lambda-cyhalothrin, gamma-cyhalothrin, per- methrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, te- fluthrin, tetramethrin, tralomethrin, transfluthrin and proflu
  • growth regulators selected from a) chitin synthesis inhibitors that are selected from the benzoylureas bistrifluron, chlorfluazuron, cyramazin, diflubenzuron, flu- cycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole and clofentazine; b) ecdysone antagonists that are selceted from halofenozide, methoxyfenozide, te- bufenozide and azadirachtin; c) juvenoids that are selected from pyriproxyfen, methoprene and fenoxycarb and d) lipid biosynthesis inhibitors that are selected from spirodiclofen, spiromesifen and
  • GABA antagonist compounds selected from acetoprole, endosulfan, ethiprole, fipronil, vaniliprole,
  • macrocyclic lactone insecticides selected from abamectin, emamectin, milbe- mectin, lepimectin and spirosad;
  • METI I compounds selected from fenazaquin, pyridaben, tebufenpyrad, tolfen- pyrad and flufenerim;
  • METI Il and III compounds selected from acequinocyl, fluacyprim and hydrame- thylnon; (2.10) uncoupler compounds: chlorfenapyr;
  • (2.11 ) oxidative phosphorylation inhibitor compounds selected from cyhexatin, diafen- thiuron, fenbutatin oxide and propargite;
  • R 1 is -CH 2 OCH 2 CH 3 or H and R" is CF 2 CF 2 CF 3 or CH 2 C(CHs) 3 ; anthranilamide compounds of formula F 2
  • B 1 is hydrogen, CN or Cl
  • B 2 is Br or CF 3
  • R B is hydrogen, CH 3 or
  • Herbicides for example imidazolinone herbicides such as imazethapyr, imazamox, imazapyr and imazapic, or dimethenamid-p;
  • Molluscicides nematicides, herbicides, algicides, bactericides, biologicals, bird / mammal repellents, fertilizers, fumigants, growth regulators and rodenticides are well known to a person skilled in the art.
  • Preferred insecticides are selected from acetamiprid, alpha-cypermethrin, beta- cypermethrin, bifenthrin, carbofuran, carbosulfan, clothianidin, cycloprothrin, cyfluthrin, cypermethrin, deltamethrin, diflubenzuron, dinotefuran, etofenprox, fenbutatin-oxide, fenpropathrin, fipronil, flucythrinate, imidacloprid, lambda-cyhalothrin, nitenpyram, pheromones, spinosad, teflubenzuron, tefluthrin, terbufos, thiacloprid, thiamethoxam, thiodicarb, tralomethrin, triazamate, zeta-cypermethrin, spirotetramat
  • More preferred insecticides are GABA antagonist compounds, herein preferred being fipronil, and nicotinic receptor agonist/antagonist compounds, herein preferred being clothianidin, imidacloprid and thiamethoxam.
  • a particularly preferred insecticide is fipronil.
  • no further fungicides are employed in addition to the fungicides employed in accordance with the invention.
  • no further active compounds except the at least one azole fungicide, the at least one gibberellin and the at least one optionally used anilide fungicide are employed in the method and the composition of the invention.
  • formulations containing the active ingredients according to the invention are prepared in a known manner, e.g. by extending the active substances with solvents and/or carriers, if desired using surface-active substances, i.e. emulsifiers and dispersants.
  • solvents and/or carriers if desired using surface-active substances, i.e. emulsifiers and dispersants.
  • Solvents/auxiliaries which are suitable are essentially:
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example mineral fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, methyl hydroxybutyl ketone, diacetone alcohol, mesityl oxide, isophorone
  • lactones for example gamma-butyrolacton
  • pyrrolidones pyrrolidone, N-methylpyrrolidone, N- ethylpyrrolidone, n-octylpyrrolidone
  • acetates glycols, fatty acid dimethylamides, fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • ground natural minerals e.g. kaolins, clays, talc, chalk
  • ground synthetic minerals e.g. highly disperse silica, silicates
  • emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
  • Surface active compounds are all those surfactants which are suitable for formulating agrochemical actives, in particular for the active ingredients used according to the present invention, and which may be nonionic, cationic, anionic or amphoteric. According to their action, surfactants - sometimes referred to as "additives” - may be divided into wetters, dispersants, emulsifiers or protective colloids; however, these particular groups may overlap and cannot be divided strictly.
  • Suitable wetters are all those substances which promote wetting and which are conventionally used for formulating agrochemical active ingredients.
  • Alkylnaphthalenesul- fonates such as diisopropyl- or diisobutylnaphthalenesulfonat.es can be used preferably.
  • Dispersants and/or emulsifiers which are suitable are all nonionic, anionic and cationic dispersants or emulsifiers conventionally used for formulating agrochemical active in- gredients.
  • the following can preferably be used: nonionic or anionic dispersants and/or emulsifiers or mixtures of nonionic or anionic dispersants and/or emulsifiers.
  • Suitable nonionic dispersants and/or emulsifiers which may be employed are, in particular, ethylene oxide/alkylene oxide block copolymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, for example polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, tristearyl phenyl polyglycol ether, alkylarylpolyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters and methyl cellulose.
  • ethylene oxide/alkylene oxide block copolymers alkylphenol polyglycol
  • Suitable anionic dispersants which and/or emulsifiers which may be employed are, in particular, alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alky- larylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore arylsulfonate/formaldehyde condensates, for example condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, ligninsulfonates, lignin-sulfite waste liquors,
  • Protective colloids are typically water soluble, amphiphilic polymers.
  • proteins und denatured proteins such as casein, polysaccharides such as water soluble starch derivatives and cellulose derivatives, in particular hydrophobic modified starch and celluloses, furthermore polycarboxylates such as polyacrylic acid and acrylic acid copolymers, polyvinylalcohol, polyvinylpyrrolidone, vinylpyrrolidone copolymers, polyvi- nyl amines, polyethylene imines and polyalkylene ethers.
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, etha- nol, propanol, butanol, cyclohexanol, cyclohexanone, mesityl oxide, isophorone, strongly polar solvents, for example dimethyl sulfoxide, 2-pyrrolidone, N- methylpyrrolidone, butyrolactone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic
  • Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth
  • Formulations for the treatment of seed may additionally comprise binders and/or gelling agents and, if appropriate, colorants.
  • the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, in particular from 5 to 50% by weight, of the active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the relevant formulations will, after having been diluted by a factor of two to ten, give active substance concentrations of from 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in the ready-to-use preparations.
  • Water-soluble concentrates (SL, LS) 10 parts by weight of active substance are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active substance dissolves upon dilution with water. This gives a formulation with an active substance content of 10% by weight.
  • Emulsions (EW, EO, ES)
  • active substance 25 parts by weight of active substance 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 introduced into 30 parts by weight of water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion.
  • the formulation has an active substance content of 25% by weight.
  • Water-dispersible granules and water-soluble granules 50 parts by weight of active substance are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluid- ized bed).
  • the formulation has an active substance content of 50% by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • active substance 75 parts by weight of active substance are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel.
  • the active substance content of the formulation is 75% by weight. Dilution with water gives a stable dispersion or solution of the active substance.
  • active substance 0.5 parts by weight are ground finely and associated with 95.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active substance content of 0.5% by weight.
  • Suitable formulations for the treatment of seeds are, for example:
  • powders such as water-dispersible, water-soluble and dustable powders, dusts and suspensions are preferred.
  • gel formulations are preferred.
  • water-soluble concentrates and emulsions may be expediently used.
  • formulations are particularly preferred for seed treatment: flowable con- centrates (especially FS); solutions (especially LS); powders for dry treatment (especially DS); water dispersible powders for slurry treatment (especially WS); water- soluble powders (especially SS) and emulsions (especially ES). Also preferred are gel formulations (especially GF). These formulations can be applied to the seed diluted or undiluted.
  • FS formulations comprise from 1 to 800 g/l active substances, 1 to 200 g/l surfactants, 0 to 200 g/l antifreeze agent, 0 to 400 g/l binder, 0 to 200 g/l colorants and solvents, preferably water.
  • Preferred FS formulations of the active substances for the treatment of seed usually comprise 0.5 to 80% active substance, 0.05 to 5% wetter, 0.5 to 15% dispersant, 0.1 to 5% thickener, 5 to 20% antifreeze agent, 0.1 to 2% antifoam, 1 to 20% pigment and/or colorants, 0 to 15% adhesive or sticker, 0 to 75% filler/vehicle and 0.01 to 1 % preservative.
  • a seed treatment formulation preferably comprises at least one auxiliary agent that is specifically suited for the seed treatment, i.e. an auxiliary agent which in particular promotes adhesion of the active ingredients to and/or penetration into the seeds and/or otherwise improves stability and/or manageability of the composition or the seeds treated therewith.
  • seed treatment auxiliary agents are selected from the group consisting of agents suitable for seed coating materials, agents suitable for solid matrix priming materials, penetration enhancers suitable for promoting seed imbibition, colorants, anti- freezes, and gelling agents.
  • the seed coating material comprises a binder (or sticker).
  • the coating material also comprises one or more additional seed treatment auxiliary agents selected from the group consisting of fillers and plasticizers.
  • Binders (or stickers) are all customary binders (or stickers) which can be employed in seed treatment formulations. Binders (or stickers) that are useful in the present invention preferably comprise an adhesive polymer that may be natural or partly or wholly synthetic and is without phytotoxic effect on the seed to be coated.
  • the binder (or sticker) is biodegradable.
  • the binder or sticker is chosen to act as a matrix for the a tricarboxylic acid biphenylamide of formula I.
  • the binder may be selected from polyesters, polyether esters, polyanhy- drides, polyester urethanes, polyester amides; polyvinyl acetates; polyvinyl acetate copolymers; polyvinyl alcohols and tylose; polyvinyl alcohol copolymers; polyvinylpy- rolidones; polysaccharides, including starches, modified starches and starch derivatives, dextrins, maltodextrins, alginates, chitosanes and celluloses, cellulose esters, cellulose ethers and cellulose ether esters including ethylcelluloses, methylcelluloses, hydroxymethylcelluloses, hydroxypropylcelluloses and carboxymethylcellulose; fats; oils; proteins, including casein, gelatin and zeins; gum arabics; shellacs; vinylidene chloride and vinylidene chloride copolymers; lignosulfonates, in particular calcium N
  • the seed treatment formulation contains at least one polyester, which, in particular, is selected from polylactides, partially aromatic polyesters (copolymers of terephthalic acid, adipic acid and aliphatic diols), polygly- colides, polyhydroxyalkanoates and polytartrates.
  • the amount of binder (or sticker) in the formulation can vary, but will be in the range of about 0.01 to about 25% of the total weight, more preferably from about 1 to about 15%, and even more preferably from about 5% to about 10%.
  • the coating material can optionally also comprise a filler.
  • the filler can be an absorbent or an inert filler, such as are known in the art, and may include wood flours, cereal flours, tree bark mill, wood meal and nut shell meal, sugars, in par- ticular polysaccharides, activated carbon, fine-grain inorganic solids, silica gels, silicates, clays, chalk, diatomaceous earth, calcium carbonate, magnesium carbonate, dolomite, magnesium oxide, calcium sulfate and the like.
  • Clays and inorganic solids which may be used include calcium bentonite, kaolin, china clay, talc, perlite, mica, vermiculite, silicates, quartz powder, montmorillonite, attapulgite, bole, loess, lime- stone, lime and mixtures thereof.
  • Sugars which may be useful include dextrin and mal- todextrin.
  • Cereal flours include wheat flour, oat flour and barley flour.
  • the filler may also comprise fertilizer substances such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and mixtures thereof.
  • the filler is selected so that it will provide a proper microclimate for the seed, for exam- pie the filler is used to increase the loading rate of the active ingredients and to adjust the control-release of the active ingredients.
  • the filler can aid in the production or process of coating the seed.
  • the amount of filler can vary, but generally the weight of the filler components will be in the range of about 0.05 to about 75% of the total weight, more preferably about 0.1 to about 50%, and even more preferably about 0.5% to 15%.
  • the binder or sticker
  • matrix is to be understood to include what may be viewed as a matrix system, a reservoir system or a microencapsulated system.
  • a matrix system consists of the active ingredients and a filler uniformly dispersed within a polymer, while a reservoir system consists of a separate phase comprising the active ingredients or salts thereof that are physically dispersed within a surrounding, rate-limiting, polymeric phase.
  • Microencapsulation includes the coating of small particles or droplets of liquid, but also to dispersions in a solid matrix.
  • the active ingredients used in the coating may have an oily type composition and little or no inert filler is present, it may be useful to hasten the drying process by drying the composition.
  • This optional step may be accomplished by means well known in the art and can include the addition of calcium carbonate, kaolin or bentonite clay, perlite, diatomaceous earth, or any absorbent material that is added preferably concurrently with the active ingredients coating layer to absorb the oil or excess moisture.
  • the amount of absorbent necessary to effectively provide a dry coating will be in the range of about 0.5 to about 10% of the weight of the seed.
  • the coating material comprises a plasticizer.
  • Plasticizers are typically used to make the film that is formed by the coating layer more flexible, to improve adhesion and spreadability, and to improve the speed of processing. Improved film flexibility is important to minimize chipping, breakage or flaking during storage, handling or sowing processes.
  • Many plasticizers may be used; however, useful plasticizers include polyethylene glycol, oligomeric polyalkylene glycols, glycerol, alkylbenzylphthalates, in particular butylbenzylphthalate, glycol benzoates and related compounds.
  • the amount of plasticizer in the coating layer will be in the range of from about 0.1 % by weight to about 20% by weight.
  • Agents suitable for solid matrix priming materials which are useful in the present invention include polyacrylamide, starch, clay, silica, alumina, soil, sand, polyurea, polyacry- late, or any other material capable of absorbing or adsorbing the active ingredients for a time and releasing them into or onto the seed. It is useful to make sure that the active ingredients and the solid matrix material are compatible with each other. For example, the solid matrix material should be chosen so that it can release the active ingredients at a reasonable rate, for example over a period of minutes, hours, or days.
  • Penetration enhancers suitable for promoting seed imbibition include agriculturally ac- ceptable surface active compounds.
  • the amount of penetration enhancers will usually not exceed 20% by weight, based on the total weight of the formulation.
  • the amount of penetration enhancers will be in the range from 2% to 20% by weight.
  • Colorants according to the invention are all dyes and pigments which are customary for such purposes.
  • both pigments, which are sparingly soluble in water, and dyes, which are soluble in water may be used.
  • Examples which may be mentioned are the colorants, dyes and pigments known under the names Rhodamin B, C. I. Pigment Red 112 and C. I. Solvent Red 1 , Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1 , Pigment Blue 80, Pigment Yellow 1 , Pigment Yellow 13, Pig- ment Red 48:2, Pigment Red 48:1 , Pigment Red 57:1 , Pigment Red 53:1 , Pigment
  • the amount of colorants will usually not exceed 20% by weight of the formulation and preferably ranges from 1 to 15% by weight, based on the total weight of the formulation. It is generally preferred if the colorants are also active as repellents for warmblooded animals, e. g. iron oxide, Ti ⁇ 2, Prussian blue, anthraquinone dyes, azo dyes and metal phtalocyanine dyes.
  • Antifreezes which can be employed especially for aqueous formulations are in principle all those substances which lead to a depression of the melting point of water. Suitable antifreezes comprise alcohols such as methanol, ethanol, isopropanol, butanols, glycol, glycerine, diethylenglycol and the like. Typically, the amount of antifreeze will not exceed 20% by weight and frequently ranges from 1 to 15% by weight, based on the total weight of the formulation.
  • Gelling agents which are suitable are all substances which can be employed for such purposes in agrochemical compositions, for example cellulose derivatives, polyacrylic acid derivatives, xanthan, modified clays, in particular organically modified phyllosili- cates and highly-dispersed silicates.
  • a particularly suitable gelling agent is carrageen (Satiagel ® ).
  • the amount of gelling agent will not exceed 5% by weight of the formulation and preferably ranges from 0.5 to 5% by weight, based on the total weight of the formulation.
  • auxiliary agents that may be present in the seed treatment formulation include solvents, wetters, dispersants, emulsifiers, surfactants, stabilizers, protective colloids, antifoams, and preservatives.
  • solvents examples include water or organic solvents such as aromatic solvents (for example Solvesso ® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • the formulations of the present invention contain less than 10% by weight and preferably less than 6% by weight of said organic solvents.
  • Suitable surface-active compounds wetters, dispersants, emulsifiers, surfactants, protective colloids
  • Antifoams which can be employed are all those substances which inhibit the development of foam and which are conventionally used for formulating agrochemical active ingredients. Silicone antifoams, i.e. aqueous silicon emulsions (e.g. Silikon® SRE by Wacker or Rhodorsil® by Rhodia), long chain alcohols, fatty acids and salts thereof, e.g. and magnesium stearate are particularly suitable. Usually, the amount of antifoam will not exceed 3% by weight of the formulation and preferably ranges from 0.1 to 2% by weight, based on the total weight of the formulation.
  • Silicone antifoams i.e. aqueous silicon emulsions (e.g. Silikon® SRE by Wacker or Rhodorsil® by Rhodia), long chain alcohols, fatty acids and salts thereof, e.g. and magnesium stearate are particularly suitable.
  • the amount of antifoam will not exceed 3% by weight of the formulation and preferably ranges
  • Preservatives which can be employed are all preservatives used for such purposes in agrochemical compositions. Examples which may be mentioned are dichlorophene, isothiazolenes and isothiazolones such as 1 ,2-benzisothiazol-3(2H)-one, 2-methyl-2H-isothiazol-3-one-hydrochloride, 5-chloro-2-(4-chlorobenzyl)-3(2H)- isothiazolone, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol- 3-one, 5-chloro-2-methyl-2H-isothiazol-3-one-hydrochloride, 4,5-dichloro-2-cyclohexyl- 4-isothiazolin-3-one, 4,5-dichloro-2-octyl-2H-isothiazol-3-one, 2-methyl-2H-isothiazol-3- one, 2-methyl-2H-
  • Suitable formulations for the treatment of the growth medium, in particular the soil are, for example, granules and spray applications.
  • the total application rates (i.e. the total amount of the active substances employed in accordance with the invention) for the treatment of seed are, for example, 0.1 to 1000 g, especially preferably 1 to 750 g, more preferably 5 to 200 g, even more preferably 10 to 150 g and in particular 20 to 150 g per 100 kg of seed.
  • the active substances employed in accordance with the invention can be formulated jointly or separately.
  • the invention furthermore relates to a composition comprising at least one azole fungicide, at least one gibberellin selected from gibberellin A 4 , gibberellin A 7 and - preferably - a mixture thereof and optionally at least one anilide fungicide and also to a composition comprising at least one azole fungicide, at least one gibberellin and at least one anilide fungicide.
  • a composition comprising at least one azole fungicide, at least one gibberellin selected from gibberellin A 4 , gibberellin A 7 and - - a mixture thereof and optionally at least one anilide fungicide
  • a composition comprising at least one azole fungicide, at least one gibberellin and at least one anilide fungicide.
  • gibberellin is preferably selected from gibberellin A 4 , gibberellin A 7 and a mixture thereof and more preferably is a mixture of gibberellin A 4 and gibberellin A 7 .
  • the composition according to the invention comprises difenoconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises epoxiconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises fluquinconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises flutriafol and gibberellin A4, gibberellin A 7 or preferably a mix- ture thereof.
  • the composition according to the invention comprises imazalil and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof. In an alternatively preferred embodiment of the invention, the composition according to the invention comprises metconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof. In an alternatively preferred embodiment of the invention, the composition according to the invention comprises prochloraz and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises propiconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises prothioconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof. In an alternatively preferred embodiment of the invention, the composition according to the invention comprises tebuconazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises triadimenol and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises triticonazole and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises difenoconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises epoxiconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises fluquinconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises flutriafol, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises imazalil, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises metconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises prochloraz, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises propiconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises prothioconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises tebuconazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises triadimenol, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition according to the invention comprises triticonazole, metalaxyl-M and gibberellin A 4 , gibberellin A 7 or preferably a mixture thereof.
  • the composition of the invention comprises triticonazole, a gibberellin selected from gibberellin A4, gibberellin A 7 , and preferably a mixture of gibberellin A 4 and gibberellin A 7 , and optionally also metalaxyl-M.
  • the composition of the invention comprises triticonazole, metalaxyl-M and a mixture of gibberellin A 4 and gibberellin A 7 .
  • compositions according to the invention may take the form of a physical mixture of at least one of the above-defined fungicides with at least one of the above-defined gib- berellins.
  • the composition may also be any combination of the active substances, where it is not necessary for the individual active substances to be present as a joint formulation.
  • compositions according to the invention in which the at least one fungi- cide and the at least one gibberellin are not present in a joint formulation is a 2- component kit or a 3-component kit.
  • the present invention also relates to a 2-component kit, comprising a first component which comprises the at least one azole fungicide, optionally the at least one anilide fungicide, further a liquid or solid carrier and, if appropriate, at least one surface- active substance and/or at least one customary adjuvant, and a second component which comprises at least one gibberellin, a liquid or solid carrier and, if appropriate, at least one surface-active substance and/or at least one customary adjuvant.
  • a 2-component kit comprising a first component which comprises the at least one azole fungicide, optionally the at least one anilide fungicide, further a liquid or solid carrier and, if appropriate, at least one surface- active substance and/or at least one customary adjuvant, and a second component which comprises at least one gibberellin, a liquid or solid carrier and, if appropriate, at least one surface-active substance and/or at least one customary adjuvant.
  • the present invention also relates to a 3-component kit, comprising a first component which comprises the at least one azole fungicide, a liquid or solid carrier and, if appropriate, at least one surface-active substance and/or at least one customary adjuvant, a second component which comprises at least one anilide fungicide, a liquid or solid carrier and, if appropriate, at least one surface-active substance and/or at least one customary adjuvant, and a third component which comprises at least one gibberellin, a liquid or solid carrier and, if appropriate, at least one surface-active substance and/or at least one customary adjuvant.
  • compositions according to the invention can be present in formulated form, as described above, and/or they can contain the abovementioned, additional components (for example other active substances (fungicides, insecticides, herbicides, bactericides, nematicides, fertilizers, growth regulators and the like), adjuvants, oils, wetters and the like).
  • additional components for example other active substances (fungicides, insecticides, herbicides, bactericides, nematicides, fertilizers, growth regulators and the like), adjuvants, oils, wetters and the like).
  • compositions according to the invention are distinguished by a markedly reduced phytotoxicity. At the same time, their fungicidal activity is essentially unaltered or even improved. Accordingly, the invention also relates to the use of the composition according to the invention for the control of phytopathogenic fungi.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, flowers and grape vines
  • Cochliobolus species on maize, cereals, rice for example Cochliobolus sativus on cereals, Cochliobolus miyabeanus on rice
  • Drechslera species and Pyrenophora species on cereals, rice, turf and maize for example D. teres on barley or D. tritici-repentis on wheat,
  • Puccinia species on a variety of plants such as, for example, P. triticina,
  • Rhizoctonia species on cotton, rice, potatoes, turf, maize, oilseed rape, potatoes, sugar beet, vegetables and other plants for example R. solani on beet and a variety of plants
  • composition according to the invention is suitable for controlling soybean rust (Phakopsora pachyrhizi and Phakopsora meibomiae).
  • the composition according to the invention is a seed treatment composition. Consequently, it comprises, apart the above-defined active ingredients at least one auxiliary substance suitable for seed treatment compositions. Suitable one auxiliary substance suitable for seed treatment compositions are described above.
  • the seed treatment formulation of the present invention is a seed coating formulation.
  • Such seed coating formulations comprise the above-listed active ingredients, at least one binder (or sticker) and optionally at least one further auxiliary agent that is selected from the group consisting of fillers and plasticizers.
  • Seed coating formulations comprising binders, fillers and/or plasticizers are well-known in the art. Seed coating formulations are disclosed, for example, in US 5,939,356, US 5,882,713, US 5,876,739, US 5,849,320, US 5,834,447, US 5,791 ,084, US 5,661 ,103, US 5,622,003, US 5,580,544, US 5,328,942, US 5,300,127, US 4,735,015, US 4,634,587, US 4,383,391 , US 4,372,080, US 4,339,456, US 4,272,417 and US 4,245,432, among others.
  • the coating formulations formed with the above-listed active ingredients are capable of effecting a slow rate of release of the active ingredients by diffusion or movement through the matrix into the seed or to the surrounding medium.
  • the present invention also provides a seed that has been treated by the method described above. It also provides a seed obtainable by the method described above.
  • the present invention also provides a seed that has been treated with a seed treatment formulation described above, and in particular that is coated with the formulation or contains it. It also provides a seed obtainable by using the formulation described above.
  • coated with and/or contains here signifies that the active ingredients are for the most part on the surface of the seed at the time of application, although a greater or lesser part of them may penetrate into the seed, depending on the method of application. When the said seed is (re)planted, it may absorb the active ingredients.
  • the present invention relates to a seed, especially an unsown seed, which comprises the above-defined active ingredients.
  • such a seed has a coating which comprises the above- defined active ingredients.
  • the ger- minable part and/or natural sheath, shell, pod and/or integument comprise(s) the above-defined active ingredients.
  • the active ingredients can be present in both the coating and the germinable part and/or natural sheath, shell, pod and/or integument of the seed.
  • the seeds treated according to the invention may also be enveloped with a film over- coating to protect the active ingredients coating.
  • a film over- coating to protect the active ingredients coating.
  • Such overcoatings are known in the art and may be applied using conventional fluidized bed and drum film coating techniques.
  • the seeds of the present invention can be used for the propagation of plants.
  • the seeds can be stored, handled, planted/sowed and tilled.
  • TTZ triticonazole
  • seeds of the variety AG 7601 were treated with the above-listed active compounds in the amounts given in the table below. Where more than one active substance was applied, the compounds were applied as a mixture. Triticonazole was employed as FS formulation in a concentration of 500 g/l; 25 g active substance per 100 kg seed. GA3 was applied in form of the commercial product Release from Valent BioSciences in a concentration of 33.8 g/l; 1.25 g active substance per 100 kg seed. The treatment was effected by means of a HEGE 11 seed treatment apparatus.
  • TTZ triticonazole
  • GA3 was applied in form of the commercial product Release from Valent BioSciences in a concentration of 33.8 g/l; 1.25 or 5 g active sub- stance per 100 kg seed.

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Abstract

La présente invention porte sur l'utilisation d'au moins une gibbérelline pour réduire ou prévenir l'effet phytotoxique de fongicides azoles, ou de fongicides azoles utilisés en combinaison avec des fongicides anilides, sur des plantes dont les semences ou les milieux de croissance ont été traités par ces fongicides. L'invention porte également sur un procédé pour réduire ou prévenir l'effet phytotoxique de fongicides azoles, ou de fongicides azoles utilisés en combinaison avec des fongicides anilides, sur des plantes dont les semences ou les milieux de croissance ont été traités par ces fongicides par traitement des semences ou du milieu de croissance des semences également par au moins une gibbérelline. Un autre aspect de l'invention est un procédé pour lutter contre les champignons phytopathogènes, qui comprend le traitement des semences d'une plante ou du milieu de croissance des semences par au moins un fongicide azole en combinaison avec au moins une gibbérelline et facultativement au moins un fongicide anilide. Finalement, l'invention porte sur une composition comprenant au moins un fongicide azole, au moins une gibbérelline et facultativement au moins un fongicide anilide.
PCT/EP2008/057892 2007-06-20 2008-06-20 Gibbérellines comme phytoprotecteurs de sécurité pour des fongicides présentant une activité phytotoxique WO2008155416A2 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010123849A1 (fr) 2009-04-20 2010-10-28 Valent Biosciences Corporation Composition fongicide
US20140011867A1 (en) * 2011-03-25 2014-01-09 Zhejiang Hisun Pharmaceutical Co., Ltd. Effect of borrelidin for controlling soybean phytophthora root rot
WO2017072013A1 (fr) * 2015-10-27 2017-05-04 Bayer Cropscience Aktiengesellschaft Composition contenant un phyto-protecteur, un fongicide et du metalaxyl

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2535332A1 (de) * 1975-08-07 1977-02-17 Bayer Ag Fungizide mittel
DE2734426A1 (de) * 1976-07-29 1978-02-16 Ici Ltd Zusammensetzung und verfahren zur bekaempfung von pilzen
WO2002069715A2 (fr) * 2001-03-06 2002-09-12 Bayer Cropscience Ag Agent desinfectant
WO2007065843A2 (fr) * 2005-12-09 2007-06-14 Basf Se Utilisation de gibberelline comme agent de protection pour azoles afin de lutter contre des champignons parasites

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2535332A1 (de) * 1975-08-07 1977-02-17 Bayer Ag Fungizide mittel
DE2734426A1 (de) * 1976-07-29 1978-02-16 Ici Ltd Zusammensetzung und verfahren zur bekaempfung von pilzen
WO2002069715A2 (fr) * 2001-03-06 2002-09-12 Bayer Cropscience Ag Agent desinfectant
WO2007065843A2 (fr) * 2005-12-09 2007-06-14 Basf Se Utilisation de gibberelline comme agent de protection pour azoles afin de lutter contre des champignons parasites

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010123849A1 (fr) 2009-04-20 2010-10-28 Valent Biosciences Corporation Composition fongicide
EP2421369A1 (fr) * 2009-04-20 2012-02-29 Valent Biosciences Corporation Composition fongicide
EP2421369A4 (fr) * 2009-04-20 2013-05-22 Valent Biosciences Corp Composition fongicide
US20140011867A1 (en) * 2011-03-25 2014-01-09 Zhejiang Hisun Pharmaceutical Co., Ltd. Effect of borrelidin for controlling soybean phytophthora root rot
WO2017072013A1 (fr) * 2015-10-27 2017-05-04 Bayer Cropscience Aktiengesellschaft Composition contenant un phyto-protecteur, un fongicide et du metalaxyl

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